YFP 333: Small Business Owner Tax Savings Checklist


On this episode, sponsored by First Horizon, YFP Director of Tax, Sean Richards CPA, EA, summarizes a tax checklist for pharmacy entrepreneurs and other small business owners.

Episode Summary

Too many of us are caught in the trap of only looking at taxes during tax season. As a small business owner, missing the tax mark can have significant consequences in the form of surprise payments due, missed deductions and credits, and constantly wondering if there is something else you should be doing. So whether you are a seasoned business owner or just starting, on this week’s episode, sponsored by First Horizon, YFP Director of Tax, Sean Richards, CPA, EA walks us through a small business owner tax checklist including eight key areas that demand your attention. He touches on the fundamentals of bookkeeping, qualified deductible expenses, the benefits of financial projections to make estimated payments, the significance of S Corp status, insights on determining your owner’s compensation, and much more.

Key Points From the Episode

  • A warm welcome back to the show to YFP’s Director of Tax and CPA, Sean Richards. 
  • Why record keeping is vital for a smooth tax season. 
  • The separation of church and state when it comes to personal business. 
  • Why you shouldn’t fear registering your business as an LLC. 
  • When to consider working with a professional and what to expect from the relationship. 
  • Understanding the basics of bookkeeping. 
  • Defining deductible expenses and why it’s important to understand this term. 
  • The difference between tax planning and tax preparation.
  • Projections and estimated payments: making sure that you’re setting the right money aside. 
  • How to determine if the S-Corp is the right fit for you.
  • Discussing payroll and how to establish your salary as a business owner. 
  • Diving deeper into Section 179 deductibles.

Episode Highlights

“Working with a professional will not solve any challenges or problems you have with disorganization.” — Tim Ulbrich [0:16:01]

“Having a strong understanding of how your business is doing financially is one of the best things that you can do as a business owner.” — Sean Richards [0:17:44]

“Paying yourself an equitable salary is not only the right thing to do by the eyes of the IRS, but it also really helps you think about where the business going and growing.” — Tim Ulbrich [0:45:48]

Links Mentioned in Today’s Episode

Episode Transcript

[INTRODUCTION]

[0:00:00.8] TU: Hey everyone, I’m Tim Ulbrick, and I want to express my gratitude for you tuning in this week to the YFP Podcast. Each and every week, we’re dedicated to providing inspiration and support on your journey towards achieving financial freedom. 

On this week’s episode, we have a special guest joining us, that’s YFP’s director of tax and CPA, Sean Richards, here to dive into a crucial topic, a tax checklist for small business owners. Whether you’re a seasoned business owner or just starting out, we’ll explore eight key areas that demand your attention. We’ll touch on the fundamentals of bookkeeping, qualified deductible expenses, the benefits of financial projections for estimated payments, the significance of S-Corp status, insights on determining your owner’s compensation, and much more.

Before we dive into this insightful conversation, let’s take a moment to thank today’s sponsor, First Horizon. Afterward, we’re jumping to my conversation with Sean Richards.

[SPONSOR MESSAGE]

[0:00:53.6] TU: Does saving 20% for a down payment on a home feel like an uphill battle? It’s no secret that pharmacists have a lot of competing financial priorities, including high student loan debt, meeting that saving 20% for a down payment on a home may take years. 

We’ve been on a hunt for a solution for pharmacists that are ready to purchase a home loan with a lower down payment and are happy to have found that option with First Horizon. First Horizon offers a professional home loan option, AKA, doctor or pharmacist home loan, that requires a 3% down payment for a single-family home or townhome for first-time home buyers, has no PMI, and offers a 30-year fixed rate mortgage on home loans up to USD 726,200.

The pharmacist home loan is available in all states except Alaska and Hawaii and can be used to purchase condos as well. However, rates may be higher and a condo review has to be completed. To check out the requirements for First Horizon’s Pharmacist Home Loan, and to start the pre-approval process, visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[INTERVIEW]

[0:02:04.9] TU: Sean, welcome back to the show.

[0:02:06.5] SR: Thanks. Thanks for having me, yeah. Feels good, we’re through all the extension deadlines, business and individual and now we can hundred percent focus on next year. 

[0:02:14.2] TU: Hard to believe, right? We’re already talking about next tax season. You just had a webinar this week kicking off the beginnings of at least thinking about tax season. I know, many of our listeners, really, this comes to life in January, February, we’re trying to get people to think a little bit earlier, more year-round, and today, we’re focusing on really small business owner tax considerations and what are some things that people will be thinking about, planning about. 

Essentially, a checklist of sorts, and whether people are just getting started with a business or maybe they’ve been at it for a while and they can go back and see, “All right, maybe there’s some holes in the crack in the foundation that they need to go back and fill in.” We really hope that this can be an episode that people will come back and reference into the future as well of something they need to be thinking about as a small business owner as it relates to their taxes.

And Sean, we’re going to talk here and weave in some of our own personal experiences of how these things became obvious that we need to be doing as we’re growing the business but also, Sean, in the work that you’re doing and advising and working with other small business owners as well.

[0:03:15.2] SR: Yeah, there will be anecdotes from real life, with our own accounting of our own businesses and some of the people that we worked with and everything, yeah. There’s a lot in this one, I think it will be a good one to reference back to, I agree.

[0:03:25.9] TU: I know pharmacists like checklists and I know they like to know where we’re going. So, we’re going to cover eight different areas, we’ll go through these one by one and they’re really going to flow into one another, and so I think we’re going to start, maybe a little bit broader, Sean, and then we’ll get more narrow of considerations that folks should be thinking about.

Sean, number one on our list is record keeping. I think that anyone who has been in a business for any time or even if they’ve been thinking about starting, they’re being advised, maybe that’s – some advice have been given is, “Hey, you have to keep records,” But that can get lost, right? You’ve got an idea, you’re running things, it can be busy, tell us about record keeping, why it’s so important, and what people should be thinking about here.

[0:04:02.5] SR: Yeah, like you said, these will kind of flow into each other, and honestly, it’s – you kind of can’t have one of these items without what’s before it, and it all comes back to record keeping, really, at the end of the day. And that makes sense if you’re thinking about taxes and accounting just the way that they are. It’s generally, it’s the nature or say, looking back at something, it’s a historical look. 

So, you’re going to need to have references of the things that you did to be able to do something like that, but there’s just so many things that go into just being able to make decisions about your business when you’re filing taxes at the end of the year, when you’re doing tax planning, which I’ll get into a little bit later about the differences between tax planning and tax preparation. 

It all comes down to having good data, and having good data goes back to having good sourced data and inputs and everything. So just saving down everything that you can, related to the business, and I don’t mean that in the sense of just holding receipts and throwing it in the shoe box and just keeping all of the junk, but just making sure that if you’re doing financial transactions, you’re keeping them in a bank related to your business, you’re running down reports at the end of the month. 

Hopefully, you’re using some kind of ledger system like a QuickBooks or even Excel or something like that but even if not, just being able to say, “Hey, this is the money that I made this year, this is the money I paid this year.” And then even some of the ins and outs that you might not think or something that will directly relate to your taxes or business but might, if you ask your accountant about it, right? 

So, things like loan agreements and any type of employment agreements you have with folks. So, things like that. Just really, anything that you think at any point in time, “Hey, would my accountant ever possibly ask me about this?” or “May this possibly come into play when I’m doing my taxes in the future?” Bear to error on the set of caution, just keep everything. 

That being said, there’s actually some rules in some areas. So, generally speaking, I’d hold on to everything for at least three years. Some states have even longer record retention requirements but generally speaking, hold on to things for at least three years. Just get some cloud storage or a hard drive or something like that so you don’t have to take a physical space and just keep an eye on everything.

[0:06:08.1] TU: Yeah. And we use, at YFP, we use Google Drive for everything. So that becomes our system of – as you mentioned Sean, it’s not just receipts, right? It’s going to be the financial statements, whether someone’s producing those for you or you’re working on that yourself, and it might be a very basic Excel template that you’re starting with and then that will evolve over time. 

But it’s not just the receipts or the financials, it’s also the contracts, right? Things that you’re – you know, W9. I mean, just the – a lot of things that you’re going to be building over time.

[0:06:37.0] SR: Right, and even things that you might not think about. So, like, say you or you have an office space at home that you’re working out of. You can take a deduction for that and there’s a simplified way to do that with a square footage. But there’s also a way you can take actual expenses and generally, you’re going to want to do whatever is the most beneficial.

So, now we’re talking about, okay, mortgage interest and utilities and stuff but even on top of that, depreciations. So now we’re saying, “Hey, how much did you pay for your house 10 years ago?” or something. That might not be something that’s top of mind for folks but if it’s, again, even if it’s tangentially related to the business, there’s a chance you’re going to be able to possibly get a tax savings for it. 

Better to just hold onto it and ask somebody about it, “Hey, can I get a deduction for this? Is it worth me keeping this data, these records here?” And then just have someone tell you, “No, you don’t need that anymore.” And then you can get rid of it.

[0:07:26.2] TU: Yeah, perhaps I should have said this at the beginning, Sean, but I know we’re going to have some people that are listening that maybe have been at this for a while and they’re kind of realizing as we’re going through these eight things like, “Oh, my gosh, like, this is a hot mess” right?

[0:07:35.9] SR: Right.

[0:07:36.6] TU: And that’s normal. You joked about the receipts in the shoe box but there’s a fine line here between, “You can’t predict everything you don’t know yet.” And the system’s going to evolve over time. You don’t want to become paralyzed by all these things but also, you want to be thinking ahead as much as you possibly can, or working with someone that can help you anticipate, that has experience working with others as well.

[0:07:56.6] SR: Exactly.

[0:07:57.4] TU: And I think an important part of that record-keeping, Sean, has been moved to number two on our checklist is this concept of comingling personal and business and really wanting to separate these out and ideally, we’re doing this from jump street, right? So we can have clean records and again, this isn’t always done, whether someone’s anticipating where they’re going to go or maybe they’re confused about how to incorporate or do they need to set up an LLC.

Lots of things to consider here, but talk to us about the importance of separation of church and state when it comes to personal business.

[0:08:29.5] SR: I was going to say the separation of church and state but I wasn’t sure if that was alright. So, I’ve used it before but I held off for a minute. Yeah, I mean, that again, it’s going back to the record-keeping thing, and being able to produce data and produce useful information about your business. So, if you need to say to yourself, “All right, how much money did I make this year or how much did I make, how much did I spend in expenses to my vendors?”

If you have to then go and start pouring through and combing through bank accounts and picking out, “All right, well, this was related to my kid’s school stuff but this was related to the business trip that I went on” and everything, just the notion of even having to do that from the beginning is – it’s just stressful to even think about. There were legal sides to it too. I mean, if you have an LLC and you set up a separate business, it’s always kind of there to keep things separate.

[0:09:15.8] TU: Yeah.

[0:09:16.0] SR: Then it begins to become something where, like you said, you might not know at first, “Hey, I’m starting something out, it’s just a little side project, I’ll use my regular account for now and kind of keep track of things on paper.” Then all of a sudden, things expand and get bigger and hey, maybe you’re incorporating or bringing on partners and stuff, and then you start getting into things, which I won’t really go too deep into because I’ll put the audience to sleep.

But you start talking about your basis in a partnership interest or something like that or your basis as a shareholder in a corporation, and if you’re sharing funds or borrowing things from here and putting it in this pocket and using your personal home equity line of credit to fund the line of business that you’re doing, it just, it muddies the waters too much from the beginning.

So, to any extent, you can keep that stuff separate. That’s the recommendation. That being said, number one is, if you’ve already done some things where, “Hey, I’ve put a couple of expenses on this card” it’s not the end of the world, it’s just being able to identify those things. So, if you can go back now and start to be able to put a report together where you’re chipping away the personal stuff and you have the business stuff ready now or towards the end of the year and not in April or March actually, if we’re talking about business returns.

But the other thing is that you don’t have to necessarily hold yourself to that a million percent. And I know this is offering up not a best practice but there will be times when I have people come to me and say, “Hey, if I go put this big credit card or this big flight on my personal card that I just opened up, I’m going to get myself a huge refund back from my credit or big reward, then I’ll be able to put back in the business” or something like that.

Those things will happen and it makes sense, you have to do it. It just goes back to the record-keeping thing. Let your accountant know or keep track yourself. “Hey, this was a loan from me as a business owner to the business and now, I’m going to actually pay myself back that amount from my business account.” Just keep track of it that way. Don’t completely handcuff yourself but make sure you try to keep things as separate as you possibly can.

[0:11:19.3] TU: Yeah, that’s great stuff. I think too, there’s – you mentioned some of the legal piece, which again, we’re not lawyers but that’s an important consideration of keeping things separate and where the liability protection ends. I think the other thing I see here, Sean, often, is the idea of starting, setting up a business, registering with the state, getting your employer identification number, opening a bank account. 

That seems big and scary, which I think can be intimidating to people that are on the front of it but it’s really not that difficult nor is it that expensive. And so I think, as early as you possibly can, once you’ve got that bank account and the business’s name that’s really going to help you with the record-keeping being separate. The other thing I would just say is from a visibility and a cleanliness as an owner to understanding where your business is at. 

Like, we don’t want to muddy those waters as you talked about, right? So, I want to be able to quickly see, how’s the revenue, how’s the expenses, where are we at? And obviously as you grow, you’re going to look at this period versus another period and what’s the growth or not the growth. What do we need to change?

So, I think really having good insight into what’s the health of the business, the separation helps. And then the other thing I would add, which is a little bit more in the mindset side of things is sometimes when we are just starting, we have some of that resistance and devastation of like, “Well, this is just kind of small and I’m not sure where it’s going to go and so, I’m just going to do it with my personal.” 

Like, believe in yourself, right? Where are we going? And worst-case scenario as we dissolve the business, we shut down the banking account and we move on, but I think really establishing the goals that you have for the business as well.

[0:12:49.4] SR: Right, and we’ll talk about it in a little bit more later but the LLC thing, again, neither of us are lawyers but a lot of people get scared by that because they think, “Oh, it’s a new entity, it’s going to open up this whole separate tax thing.” But most of the time, if you’re a sole proprietorship and you open an LLC, it’s just going to land on your personal tax return like kind of a regular side business anyways. So don’t let that notion of things scare you too much.

[0:13:12.1] TU: All right, number three on our list, Sean. Number three is working with a professional. You’ve alluded to this a couple of different times. Some people, as it gets started, they may work with a professional right away, they may wait, and that could either be an accountant, bookkeeper, both, we’ll talk about bookkeeping basics here in a little bit. 

This was one of the first areas, Sean, that we actually outsourced at YFP, as we were looking at growing the business. We had times where that perspective was very helpful and times where we’re like, maybe not. So, I think this is a challenge where, “You know what? I’m going to hire someone that can really understand my business and advise me.” And I often had this feeling of, “I don’t know what I don’t know”, right? 

So, I’m looking for someone to kind of guide me, rather than just being there when I have questions. So, talk to us about the working with the professional. Maybe the “When”, as well as, what are we looking for in that relationship?

[0:14:01.8] SR: Yeah, and like you mentioned, we’re going to go into bookkeeping basics, but I think having this n your checklist of where you’re in the end of the year, and really any point in the business year is trying to make that determination, “Hey, am I going to do this or not?” You don’t even necessarily have to go down the path of understanding all of the ins and outs of the bookkeeping if you’re going to decide off the bat, “Hey, I’m going to pay somebody to do that for me.” 

Not that you shouldn’t get the basics and stuff, but if you’re going to say, “Hey, I want to outsource this now and have somebody run that whole show”, you don’t necessarily even have to get yourself in the weeds from the beginning. But I think it’s just one of those things that you have to decide, like you were saying, where do you want to be spending your time and your energy and where are your strengths and your weaknesses, right? 

So, if maybe you have a finance background and you say, “I can put a couple of hours towards this and it’s not a big deal, I got a pretty good handle on things and I can run it myself.” That’s perfectly fine but you might be saying to yourself, “Hey, I know a lot of people who just absolutely hate everything to do with numbers” and that’s okay too. If number scare you and you hate numbers, that’s fine but they’re not going to go away. 

So, ignoring them or trying to just say, “Hey, we’ll get there at the end of the year and figure it out then.” I mean, that is one way to do it but it’s certainly not the best way to do it. So, I think it’s just something where you have to really think about where you’re at, what your strengths and weaknesses are, and also what do you want to do when it comes to tax season, right? 

If you’re talking about a sole proprietorship then that’s going to land on your personal return, that’s probably something that you can handle. But if you’re getting into partnerships and corporations, now you’re filing different returns and they’re a little bit more than a regular person’s probably used to with HNR block or whatever. So, that’ might begin to necessitate having a tax professional just sheerly out of expertise. 

So, there’s a lot of different things. I always use the accountant cop-out answer that Tim Baker uses of, “It depends.” But it really does depend. But I think having that decision early on in your process will help plan out the rest of everything else that we’re going to talk about in a minute.

[0:15:57.6] TU: And this is worth saying, and maybe saying again and saying again, which is working with a professional will not solve any challenges or problems you have with disorganization, right?

[0:16:07.7] SR: Correct.

[0:16:08.6] TU: They can advise, they can help, they can – we talked about things like record keeping, but they’re not there from an organization standpoint. I think this is something, again, no judgment, right? People that are just getting started in the business, you’re focusing on the business, you’re growing things, you may not be thinking about organization and records and all that, but at some point, that’s got to become a priority. And if they’re working with someone the first time, that may not be something that is top of mind, so.

[0:16:32.7] SR: Yeah, but a professional though also can, on the flip side and again, it’s not going to be – it’s not going to solve disorganization problems but can definitely help advise with, “Hey, you’ve been struggling keeping track of all these things. Why don’t you get a QuickBooks subscription, we’ll connect all your bank accounts and then I can handle things from there and keep track of things as they come in.” 

And now, all of a sudden, you’re not panicking every month or every year with the thousand transactions. You have a bookkeeper who is going in every week or every month and categorizing things and sending you reports, so. 

[0:17:01.9] TU: Yeah.

[0:17:02.1] SR: Again, it might not solve your problems with a wave of a magic wand but they can definitely get you there.

[0:17:08.7] TU: So, let’s go to number four on our small business owner tax checklist, and Sean, that’s bookkeeping. We’ve danced around this here a couple of times so far but whether or not someone is working with a bookkeeper, there are things they have to be ready for and make sure that they’re tracking. So, talk to us about those items that they have to be ready to report on, whether they’re doing it themselves or whether they’re working with someone that they hire.

[0:17:30.5] SR: Yup, like you said, and like I was just saying before too, even if you have somebody who is doing this for you, reporting on it, and kind of explaining it all to you, you still have to generally be able to understand what they’re talking about, right? I mean, you can only break things down in layman’s terms so much, and having a strong understanding of how your business is doing financially is obviously, one of the best things that you can do as a business owner, I think.

So, if you take a look at – and I’ll talk about the entity types in a little bit – but if you look at the three main, or at least in my mind, tax returns that you’ll have for small businesses typically is a schedule C on your 1040. That’s just your regular kind of sole proprietorship. It can be an LLC, cannot, but just a regular person side gig kind of thing, and then you have a 1065 which is a partnership. 

So that’s the default if you have an LLC and you have more than one person, and then S-Corp, I’m sure a lot of people have heard of that say, 1120-s. Those are the three main forms that you typically see for filing business returns at the end of the year. If you look at the three of those, the main front of the forms, they’re all basically the same thing. You have your revenues, your, “Hey, what were my sales, what was my service income if I had any other kind of income, and what were my expenses?”

And you’ll see that all three of them have generally the same categories for expenses. Like advertising and travel and mortgage interest and things like that. So, it’s pretty similar across the board and you’re going to really have to be able to report on that stuff, no matter what kind of business you run, you’re going to have to know what your revenues are and you’re going to have to know what your expenses are.

Revenues, I’m not really going to spend a whole heck of a lot of time on. I mean, I think people generally kind of have a feel for that, it’s cash in the door. The one thing I would say there is if you’re doing service revenue, it might be a little bit harder to track when you’re actually performing a service and getting paid versus actually selling a good. So, a little bit more keep eye on there but honestly, again, people typically have a good feel for that.

It’s more the expense side that I think things can kind of trip people up on. You typically think, “Hey, whenever I’m spending cash out the door that’s going to be an expense for the business and I can probably deduct it.” And generally, that’s true, but there’s a lot of things that come in that can mix that up a little bit. I mean, property is one thing. I was mentioning before, depreciation, right? 

So, you probably think, “Hey, I’m paying for this office space and I have a mortgage on it. My mortgage, I should be able to write that off, right?” Mortgage interest you can but the mortgage principle, you don’t. You get that back via depreciation but again, that’s something you might not be thinking about or might not really have insight into, or vehicles for example. You can have a billion different ways to write off vehicle expenses. 

Whether you’re taking actual expenses or like a standard mileage rate. It all depends on how much you’re using the vehicle for business purposes, there’s all sorts of depreciation rules and stuff. There’s just a lot when it comes to expenses. So, that’s probably the biggest area on the PNL at least, the profit and loss statement to really have a good handle on when it comes to basic bookkeeping stuff.

[0:20:25.4] TU: Sean, as you’re talking, it’s reminding me of – sorry to interrupt you, it’s reminding me of Schitt’s Creek episode where Johnny Rose – 

[0:20:33.4] SR: Yeah. I already know where this is going.

[0:20:35.0] TU: You can’t just buy things for yourself and deduct them as an expense.

[0:20:39.8] SR: It’s a write-off, it’s just a write-off, exactly.

[0:20:42.1] TU: It’s a write-off, just a write-off.

[0:20:43.4] SR: And hey, a lot of times, and we’ll talk about what’s a deductible business expense. A lot of times, if you’re spending money on a business, it is but you’re correct, you can’t just be like David Rose and just go buy everything.

[0:20:54.3] TU: Oh my gosh.

[0:20:55.7] SR: From the blouse barn. So, that’s the PNL. The balance sheet is kind of – I don’t want to say, it’s the ugly stepchild of the financial statements but it’s the one that people generally have an actually have a pretty good understanding of it without even really knowing what a balance sheet is just because of the nature of two of the biggest components of it. So, your balance sheet is going to be your assets, it’s kind of one-half of the calculation and then the other half is liabilities and equity. 

So, assets are pretty much what you think. If you look up the book definition of an asset, it’s kind of what it is for a business. It’s kind of what it is for a business. It’s basically something that’s expected to generate money for you, it’s a positive sort of resource that you have so cash, receivables, things like that, property, equipment. Again, things that people probably have a pretty good handle on.

“Hey, I have this much cash in the bank, Johnny owes me this much money and I own all these cars” right? Liabilities is the other side, on the other side. So, that’s the opposite of the asset basically. It’s like, “Hey, loans, do I have debt, do I have credit cards, do I have a mortgage? Do I owe my vendors?” Things like that.

So again, people typically have a pretty good handle of that, whether they’re really thinking about it or not, you usually know, “Hey, what are my credit card balances, what’s my line of credit balance?” whatever. Equity is the piece that is sort of – it always just ends up being the plug piece but it’s really important when it comes to taxes. So, if you think about – I was alluding to before, you were in a partnership.

You have a basis in that partnership and again, if you’re not an accountant, you might be thinking like, “What in the world is that?” It’s something that, I don’t want to say it gets overlooked but if you’re not really thinking about it from the beginning and again, getting back to commingling funds and stuff, basis is something that really matters a lot in the tax calculation. But can get muddied very quickly if you don’t have a handle on things. 

And that really comes into play, equity is really where that kind of lands and I’ll caution that, if you look on the balance sheet, you look at equity, that doesn’t mean that that’s your basis or if you have multiple partners and stuff, it doesn’t necessarily equal that. But being able to have a handle on what your equity is, it really is a value of your company if you think about it. It’s your assets minus your liabilities. If everything right now came due and you had to pay off all of your vendors and everything, what do you have left? 

That’s the value for your business. So, like I said, it’s the one that’s overlooked a little bit and it’s not as easy to maintain. Typically you don’t have to report a balance sheet if you have a small business and you’re doing like sole proprietorship or something, but it’s something that if you can get somebody to keep those books for you and be able to have a handle on it.

[0:23:28.2] TU: So, as you mentioned, assets equals liabilities plus equity or we could change the equation around assets minus liabilities equals equity, right?

[0:23:35.6] SR: Again, exactly right.

[0:23:36.6] TU: So, is my high school math still good?

[0:23:38.4] SR: Yes, that would be algebra. Very, very good. 

[0:23:41.2] TU: So, let’s talk more within the bookkeeping basics here. Let’s talk more about the deductible expenses, right? This is probably one of the most common questions that we get you alluded to before that – especially early on the journey, people may have this perception of, “Hey, I can buy anything for the businesses and it’s a deductible expense.” So, define that term just a little bit further and why that’s important, and then some of the most common areas or deductible expenses that small business owners should be thinking about.

[0:24:06.8] SR: Yup. Sure. So, deductibility, it really comes down to the main things. So, is it ordinary and necessary? So, that basically means, if I have a business, is that expense something that actually makes sense in the course of a business? So, if you own a financial education company and you’re buying courses for your employees to take to learn about education and finance and stuff, that’s probably an ordinary expense.

If you’re buying tickets to – I was going to say, the Phillies in the World Series but they’re not really there, I guess. So, if you’re buying tickets to a baseball game or something, that’s probably not an ordinary expense, right? So, sorry for the low blow. I actually was rooting for the Phillies this year, that wasn’t meant to be, it just popped in my head first thing. So, ordinary necessaries, number one. Reasonable, which is in the same kind of vein but similar sort of thing.

So right, if we go back to that example I was just giving in, your employees are purchasing education, financial education courses, right? If those courses cost USD 500, a thousand dollars or something, it’s probably reasonable. If those courses cost USD 250,000 each, that’s starting to be, “Hey, you know, what’s going on there?” In fact, it’s probably not started to be, it’s definitely unreasonable but I think you get what I’m saying.

[0:25:19.3] TU: Yeah. 

[0:25:19.3] SR: And then the third piece is paid during the year or if you’re on the accrual basis incurred during the year. But generally speaking paid but as the case is with everything, there is a lot of exceptions to these rules and with expenses in particular, those exceptions come out quite a bit. So, when we think common deductible expenses, cost of goods sold is going to be the most common or easy to identify if you’re a retail business or you’re selling goods. 

And then the flip side of that, of the analogy I guess is if you have a service business, it’s not as easy to say, “What’s my cost of goods sold?” because you’re not selling a good but being able to determine, “Hey, what are my direct expenses directly related to the services that I’m providing?” So, it’s typically labor, contract labor, things like that. Compensation, so that’s one that is usually is a deductible expense. 

However, it very often is not something that’s a deductible expense if it’s for an owner-employee of whatever this is. So, and you know, I’ll get into a little bit of specifics in a bit with some of these different entity types but if you’re a sole proprietorship and you are paying yourself and it is a little bit contradictory to what I was saying before where you want to be able to kind of keep good books and keep records of everything. 

So, you’re probably saying, “All right, I’m working 40 hours a week on my business. I am paying myself 50 grand a year” whatever it is, that’s a salary expense to me, and then you write that off. But as an owner of a sole proprietorship, that’s not something that’s a deductible expense and that comes into play if you’re S-Corp. Some of those, some of the compensation that you’re getting. 

If it is a salary expense, that will be deductible but then if you’re taking profit distributions, it’s not. So, there is a lot when it comes into compensation. If you’re paying contractors, separate contractors that aren’t yours generally speaking, that will be deductible but more just trying to give the caution flag here of, “Hey, if you are paying anybody particularly yourself, keep an eye on that.” 

[0:27:15.7] TU: That’s really good, Sean. I think that can evolve, right? So, somebody may start as a sole proprietor, they may then have partners or not, they may or may not become an S-Corp. So, this topic of owner’s compensation and a deductible expense is one that may be ongoing. 

[0:27:30.3] SR: Oh, absolutely. It’s something – and we’ll talk about the S-Corp thing in a little bit – but exactly right. And that’s not something that is going to be set in stone and even something like not necessarily related to deductible expenses, but even something like setting aside money for taxes. I mean, you might have a rate in your head that, “Hey, I’m going to put aside 15, 20%” that can change drastically year to year depending on what things are happening with your business or your personal. 

[0:27:52.9] TU: Yeah. 

[0:27:53.3] SR: So just another thing that as with everything else, a lot of these rules and things to keep in mind aren’t necessarily set in stone for any particular point in time. On the subject of compensation, health insurance is another big one. So, that’s one that again, you got to really want to be careful about. I can’t get into all the rules now but the big thing there is really if your spouse is eligible for health insurance through whatever company they work for. 

If it’s unrelated to your small business that usually makes it nondeductible on your side, so just something to keep in mind in there. Again, I won’t go into everything but there is a lot of rules around health insurance. Travel, a lot of rules around that. So, if you’re going on business and you are spending time overnight and the primary purpose is for business, most of those expenses generally speaking will be deductible. 

But if it’s for leisure, probably not and the big one with transportation and travel is commuting to and from your office is never deductible. That’s the big one there that people will say, “Well, what if I work from home sometimes but then I have an office space that I go to?” If that’s a primary office location, probably not going to be a deductible expense, so that’s a big one to keep in mind.

And that’s huge too when you’re thinking about, if I am buying a vehicle and I’m taking these depreciation deductions and stuff, the mileage that you’re commuting to and from your office does not count towards business mileage, so very important to keep in mind. 

[0:29:14.6] TU: You’ve reminded me of that many times, which is good. 

[0:29:17.5] SR: Yeah, yeah, probably in a good way, right? 

[0:29:20.2] TU: Yes, yeah. 

[0:29:20.9] SR: And then you’re rolling your eyes at me kind of way. 

[0:29:22.5] TU: Yeah. 

[0:29:23.2] SR: So, one item I’ll mention as far as the exceptions to the rules I was talking about with being paid during the year is rent. So, I know a lot of people will say, “Oh, perfect. December, I’ll prepay next year’s rent and just be able to take a nice deduction this year for it.” IRS caught onto that one pretty quickly, so rent they actually specifically say, “Hey, if you prepay it, you can only take deductions for the time that it applies to.” 

And then a big one that I mentioned before is the business use of home. So, if you are using a home office space and you’re – it’s dedicated and you’re using that for your business, you usually can’t take a deduction for that and there’s two methods, a simplified, “Hey, what’s my square footage?” and you’re taking five bucks a square foot or you’re taking a percentage of your actual expenses for your home. 

The big thing there though is that I think that I kind of alluded to, it has to be strictly dedicated to that business. So, not like a half office half bedroom kind of situation. It needs to be fully for the business and really – 

[0:30:20.4] TU: Which is important with work-at-home transitions. I’m thinking about where people have bedroom office type of set up, so. 

[0:30:28.0] SR: Yeah and I mean, really, I mean I hit a couple of the big ones there as far as the expenses that are nondeductible that people often think might be. It’s really just; think of the opposite of what I just said, right? So, if you are you’re on and it’s for personal purposes, if you’re driving to and from your office, you’re going to baseball games, entertainment expenses aren’t deductible. 

Federal income tax too, that’s another big one that people think, “Hey, it’s a tax.” Alot of taxes are deductible, property taxes, estate taxes, but the Federal one itself it’s – that would be a circular reference. 

[0:31:00.3] TU: Yes, they were in. 

[0:31:00.8] SR: That they were able to, right? So, if you get that one, then your math’s definitely working nice.

[0:31:05.0] TU: Yeah. Well, I think this is an area and obviously, I’m biased, Sean, we’ve got a team that does this, and your expertise on our team knows how to do small business accounting and bookkeeping and fractional CFO and TAx 4. Obviously, I’m biased there but I think you have to ask yourself as a business owner like this is just a lot to have on your mind, right? 

So, could you learn all this, could you DIY this, could you record keep, could you bookkeep? Like technically the answer is yes. 

[0:31:31.8] SR: Right and it’s possible.

[0:31:33.2] TU: But as you think about your capacity of attention and where you need to be focusing your energy, there is a point where there’s just so many nuances and here we’re really talking more on the side of let’s make sure we’re not calling something deductible that’s nondeductible. I think really the next level is more of the, what can we be doing strategically to optimize our tax situation? And that’s a huge value of having someone in your corner. 

I do want to pause for a moment, I will be remised Sean, if I didn’t explain the Phillies reference to our listeners. 

[0:32:05.6] SR: Okay, all right, that’s fair. 

[0:32:06.8] TU: So, if our listeners don’t know, Sean’s in New Hampshire but he’s a huge Boston sports guy, and just in the past week, Tim Baker’s Phillies were eliminated from the NLCS and I assume as a Red Sox fan, that’s just beaming with joy, right? You’re a Red Sox fan. 

[0:32:23.6] SR: You know, I am a Red Sox fan but honestly, with the Phillies this year, I kind of thought it was a team of destiny sort of thing, I’ll root against a Philadelphia team if they’re going up against the Boston team because I mean it’s the in-law sort of thing. And you know if it’s the 76ers, I don’t like because they’re in conference and stuff but the Phillies, it’s NLAL, I actually was pulling for them. So, I was rooting for them by that one but at the same time, it’s a little bit of win-win. 

[0:32:50.4] TU: But the other thing why Sean is having a good week is I think the listeners know me, I’m a huge Buffalo Bill’s fan, and the New England Patriots miraculously beat the Buffalo Bills this week so.

[0:32:58.8] SR: Yes, which the term miraculous wouldn’t really have made sense for the last 20 or so years but now, it definitely does. So yeah, it’s been a good week but I think I’ll be crashing back down to reality this weekend, so we’ll see. 

[0:33:09.5] TU: Only the Buffalo Bills hand, Bill Belichick a milestone win, so I’m going to leave at that. All right, number five on our list is projections, estimated payments, making sure we’re setting money aside. I’m guessing if we have listeners that have been at this for a while, they’ll probably remember maybe an early part of their journey where it’s like, “Oh, I didn’t think about that” right? 

Didn’t know how to make estimate payments, didn’t think about how much I should set aside, and how I should project that. So, who needs to be making quarterly payments and talk to us about the process of determining that and then setting aside those dollars in planning? 

[0:33:43.8] SR: Yep, so I mean doing a projection, it all kind of comes back to what I was talking about way the beginning of this saying the difference between tax planning and tax preparation. So tax preparation, I actually always use the same analogy, I’ll use it again but I always think of tax planning as being like a film director who can sort of see things as they’re going with the actors and change course and say, “Hey, cut, re-film that, do this over.” 

And then tax preparation is the film editor who gets all the stuff and still plays an important role, works their magic, makes it all look nice. But it’s all stuff that’s already been done and you can’t turn back time and re-film any of those things, right? So, all of the kinds of theme of this entire conversation has been the idea of tax planning and actually being able to project what you think your liability is going to be at the end of the year.

And that’s where you start to get into what you’re just talking about, now we’re not talking about, “Hey, what is and what isn’t deductible” but now it can look at, “Hey, where do we have opportunities to take advantage of tax code and make a purchase and take advantage of accelerated depreciation or change our entity classification or something?” But in order to do that, you need to be able to do a projection. 

In order to be able to do a projection, you need to have books and in order to have books, you have records. So, you see how it all kind of works itself up, right? 

[0:35:00.9] TU: Yeah. 

[0:35:01.4] SR: But yeah, I mean, a projection, I think the biggest thing there, so it all comes down to what your tax classification is. So, if it’s Schedule C, you’re kind of looking at what you expect your profit and loss to be at the end of the year and you’re building that into your 1040 and then similarly, if you’re a chair holder of even an S-Corp or partnership or something, you’re going to get your distributed share of that income on a K1 at the end of the year. 

That’s going to come into your tax return, so it’s a little bit of – most of the time it’s thinking more about the tax on your personal side and less so on the business side. A lot of small businesses actually are passed through entities, where the business itself was not paying the tax, it’s actually the owners or the shareholders. So, when I say tax planning for your business, it actually is really a little bit more tax explaining on the personal side. 

But how does my business play into that and the biggest piece there is that usually small businesses will be subject to self-employment income, number one. And number two is that almost always business income won’t have any withholdings associated. 

[0:36:00.4] TU: Yeah. 

[0:36:00.8] SR: So, that’s when you need to start thinking about, “Do I have to make estimated payments? Should I be setting money aside at the end of the year?” So, there’s ways to do that, I mean again, doing a projection and really kind of you know, projection is kind of what it sounds like, you’re basically building a tax return now just with what you think it’s going to end at the end of the year. 

So doing that is good and then that will get you, “Hey, this is what I think my tax bill is going to be and this is what I think my withholdings are going to be” and everything and if you think you’re going to owe more than a thousand dollars, you should be making estimated payments, that’s the general rule. There’s something called the safe harbor, so the easy calc there, the easiest way to do it and being ultra-conservative as accountants tend to is take last year’s tax liability and multiply it by 110%, 1.1. 

And as long as you pay that in by the end of the year through withholdings and/or estimated payments or some kind of combination, then you won’t have any penalties. You can also do that with this year’s 90% of this year’s tax. But if you can – what I’m getting out with that, that’s not a known number, your last year’s tax liability is on your – 

[0:37:04.6] TU: More conservative, yeah. 

[0:37:05.5] SR: This year’s tax liability, you probably have a good handle on it but it could change, right?

[0:37:09.8] TU: Especially if you’re growing or there – just thinking about variability and this is another example, just a peak behind the curtain, Sean, of, you advising us here at YFP, this is something we’re looking at you know evolving into the future. So, you know we’re big believers in the Profit First methodology. We’ve talked about that before on the show, great book, great resource. 

There is a recommendation there for X percent of all revenue should go into a tax account. But what we found for us is that wasn’t a perfect number, because of just our personal situation as well as some of the tax benefits of being in the great State of Ohio, you know? 

[0:37:09.8] SR: Right. 

[0:37:43.5] TU: And then, so there’s – that’s one example where things are unique, and then we kind of evolve to our own calculation, which I would say is probably closer to maybe the general rule of thumb that’s out there of, “Hey, take 25%, set it aside” and then we realize, “Hey, that’s got some holes because tax situations are different.” You know, how many kids you have, what’s the total household income, all of these variables, right?

So, I think the projection piece along with what you’re suggesting on the safe harbor is so important, right? As you’re planning for the business because you want to find yourself in that situation where you don’t want a bunch of money sitting in an account that as a growing business, if you didn’t have to make that much in tax payments you could have utilize to grow the business. 

There is an opportunity cost there but we also don’t want to be surprised and put a stress on the cash flow of our business that we go to file in April and we’ve got this big tax bill due. 

[0:38:33.9] SR: Exactly, it’s a push-and-pull kind of thing. 

[0:38:35.6] TU: Yeah. 

[0:38:35.9] SR: So, being able to – at any extent that you’re able to nail that down as close as you can, like you’re saying, it’s better that way, right? You don’t want to loan the government any more money than you have to but you also don’t want to end up owing a ton of money that you may or may not have or on top of that, have any penalties where I think is associated with it too, so yeah. 

[0:38:52.8] TU: Number six on our checklist, Sean, relate to the S-Corp status, I would pursue maybe outside of, “Hey Sean, can I deduct this expense?” maybe the second most common question or pretty close to the top is, “Should I be a S-Corp?” It’s one of those things that people just throw out there of, “Hey, there’s tax benefits of being an S-Corp status.” Tell us more about what that means and when people may be asking or should be asking that question. 

[0:39:14.8] SR: Yeah, and I mean again, the theme of the whole thing is that you’re kind of looking at these things and at least at one point in the year, hopefully around now, but actually more ongoing, but at least at one point in the year saying, “What is my tax classification now and is that what it’s going to be next year or does that make the most sense next year?” So, before I even do S-Corp I’ll give the three like I had mentioned earlier in the call. 

The three most common ones that I would think of small businesses as a sole proprietorship, one person that’s what you see on your schedule, see they call it, and if you – and the biggest thing with this is that for all of these different classifications, LLCs can be any one of these. That’s the thing, if people will say, “Oh, I’m an LLC” any one of these, an LLC is a legal entity distinction versus these are tax classifications. 

You can be an LLC and classify in any one of these, as long as you fit the right requirements. So, that’s one thing to keep in mind. Again, people hear that, they think it means something different or, “Hey, my taxes are going to be different.” It doesn’t necessarily mean the case. So, sole proprietorships are the most common. If you file an LLC for a single person, that’s the default. 

The biggest thing there is that, that is subject to self-employment tax, and then again, that does not have – there’s no withholding. So, you’d want to make sure that you’re keeping track of any estimated payments and stuff. Partnerships is the default for an LLC with two plus people. So, if you and your friend or you and your sibling or something go start a business and you start an LLC, the default for that one is a partnership and that actually is a different tax return and everything. 

So that’s where again, it begins to become a little bit more than just, “Hey, I’m starting this little business.” Your share of ownership income from a partnership is subject to self-employment taxes. So, when you get your K1 at the end of the year from your partnership, that is subject to self-employment tax, which basically is just the employer portion of FICA that you don’t have because you don’t have an employer, it’s you. 

S-Corps is the more kind of exciting piece. So that is, you can have any number of owners but that is where you’re actually incorporating your business and you’re basically – it’s being taxed like a corporation now. And the biggest thing with that is that you don’t have the self-employment tax portion for what you get on your K1. So, if you were in a partnership today and you and your partners each got a K1 and reported that income, there’s self-employment tax on it. 

And then you become an S-Corp tomorrow, effectively that same stuff that’s on that K1, that same income is not subject to self-employment tax. Now, you’re probably thinking to yourself, “Wow, that sounds too good to be true.” It’s not that it is, it’s just that there are catches associated with it and the biggest catch is that when you make that jump to S-Corp, you have to be able to pay yourself as an owner a reasonable W2 salary with the FICA withholdings and everything, AKA, self-employment tax on top of any profit distributions that you’re going to be making, and that right there is the deciding point. 

Well, what people will probably say is, “Okay, well, what’s a reasonable salary and when can I make that?” and there comes my cop-out accountant answer of, “It depends” and it really does depend because you can think about a million different things. “All right, hey, I am starting a small business and I am going to be the CEO and I’m a pharmacist who is going to be providing advisory on pharmacy things.” 

Okay, is your salary a CEO salary? Because I’m sure if I Google CEO salary, the average is probably 10 million dollars or something. Is it pharmacist’s salary? Is that, I mean, are you doing mostly pharmacy-related things? Well, you’re probably will also going to be doing some bookkeeping and administrative stuff too, right? So, is it kind of an admin salary? Figuring out what that is, there really is no science to it. 

It is more of an art than a science. You have to be able to say, “Hey, this is a job that I’m doing, you know, these are comparable salaries of people that are making” and you have to be able to pay yourself, “Hey, this is what I feel and I truly believe isn’t a reasonable wage per my industry per the work that I’m doing and everything”, and you need to be able to do that again before you make that jump to S-Corp. 

And in order, once again, to determine if you can do that, you need to be able to say, “Hey, where am I in the books? Where do I expect my profit to be this year? Do I think I’m going to have a ton of profit on my K1 or I’m going to have a lot of self-employment tax? I don’t want to pay that self-employment tax, so now can I switch to S-Corp?” Well, let’s see. Do I have enough room in my profits from last year to cut myself a salary that the IRS will think is reasonable compared to other entrepreneurs that are doing the same sort of thing? 

I don’t know. I mean, I really would have to look at your finances and we’d have to talk about a lot of things. It’s a very, very long conversation but it’s a very important one because it can save you a lot of money in taxes. But it all kind of comes down to – my questions back to you will be, “What’s your expected profit and loss look? What have you been taking as distributions so far?” 

And if you can’t answer those questions, then we can’t even have this conversation. So it’s a lot of it depends but it all once again comes back to being able to have the numbers to even start to have that conversation to begin with. So, if anybody is still awake, I hope that kind of explains that. 

[0:44:27.8] TU: It’s good. 

[0:44:28.1] SR: I’m sure that put quite a few folks to sleep. 

[0:44:30.6] TU: No, it was good because this comes up so much, right? We’ve talked about this internally a lot of what’s the right amount of paying ourselves and how do we determine that and it’s so subjective, right? And number seven on our list was going to be payroll and paying yourself enough. So, you did a nice job of covering on both of those in one. 

[0:44:45.2] SR: Yep, exactly. 

[0:44:46.0] TU: And you know, just for some insights and how we have handled this, not to say this is advice in any way, shape, or form, and I would reference people. There’s a book called, Simple Numbers, Straight Talk, Big Profits! that is written by Greg Crabtree that I think does a nice job of addressing this issue. 

[0:45:01.6] SR: Yes. 

[0:45:02.1] TU: Not just from a, “Hey, the IRS is going to be concerned” if you’re kind of applying like a stockless salary, but also I think what’s important about this is, are you thinking about your salary in the context of what the business is and potentially is worth? So, what I mean by that is let’s say Tim Baker and I decided that at some point we want to wake up and sell our business. 

Well, if somebody buys it, they may not want to operate it necessarily. Maybe they do but if they don’t, they’re going to be asking themselves, “Hey, what does it cost to replace Tim or what does it cost to replace Tim?” And so if that answer is X and we’re paying ourselves a lot less than that – because then you could argue, are we really giving ourselves a true look at the profitability, the actual profitability of the business? 

And I think paying yourself an equitable salary is not only is the right thing to do by the eyes of the IRS but it also really helps you think about where is the business going and growing. Now, there is a balance there, right? If you don’t have to pay yourself USD 200,000, you can save on taxes and argue you’re paying yourself a reasonable salary, then obviously you want to do that. 

So, good resource and reference I think about with that book I mentioned. Sean, number eight on our list, which is our last item on the small business owner checklist, is seeing about some of the big purchases. We talked about deductible expenses but specifically want to dig a little bit deeper around Section 179 deductible expenses. Tell us more there. 

[0:46:26.1] SR: Yeah, that’s so – that’s really when you think about deductible expenses, the IRS basically says, “Hey, nothing is deductible unless we tell you that it is pretty much.” And when they start to incentivize larger purchases it’s because that’s what they want people to invest in. So, Section 179 is effectively the government’s way of saying, “Hey, typically you have these big things like vehicles and other equipment type purchases that you’d have to pay for upfront now but then only be able to take a little bit into depreciation every year.” 

“That’s not fair to small businesses, we want to encourage folks to put money to the business. So, we’re going to let you if you buy things that fit these bills, take that money on the first year.” Which is awesome to be able to do, especially if you have to make these purchases and it makes sense for your business. But the biggest thing by far that I would say and once again, it rolls back into everything is you really want to make sure like, “Hey, do I have to make these purchases at some point now or in the near future or am I just doing this so I can get a deduction this year?” 

Because yeah, it’s great to get a tax deduction but that’s really only a percentage. It’s not a credit, it’s not a dollar-for-dollar savings, it’s really only a percentage of a savings. So, if it’s something that you have to spend, “Hey, I’m going to have to buy a car next year anyway and I have all this profit this year and I can take that depreciation and offset those profits,” cool, but you need to be able to figure that out and if you don’t have good numbers, you can’t do it. 

[0:47:43.5] TU: Yeah. 

[0:47:43.5] SR: And if you look at your numbers and saying, “Hey, I’m going to break even right now and I don’t need a car,” then you probably shouldn’t be going out there and trying to take advantage of the Section 179 file. 

[0:47:51.0] TU: Yeah, great stuff. We’ve covered a lot, Sean, on this and we’re going to come back to these topics in the future on the show but we want to have this one episode that we could point back to and say, “Hey, small business owner” again, whether you’ve been established and you want to go back and look at some of these things or you’re just getting started wanting to build a strong foundation, we wanted this episode to be that resource. 

So, looking forward to building upon this in the future as well. If folks want to learn more about the tax and accounting services that we offer, that Sean and his team offer at YFP Tax, you can go to yfptax.com. We’ll link to that in the show notes as well. You can book a free discovery call to learn more about those services, we’ll learn more about you to determine whether or not there’s a good fit there. 

For business owners, we offer everything from business tax filing, bookkeeping, all the way up to fractional CFO services, payroll, so depending on where you’re at in the journey, it might be, “Hey, we need all of that” or “We just need a portion of that” and we could grow together over time. So, Sean, thanks so much again for your time. 

[0:48:47.3] SR: Thank you, Tim, have a good one. 

[END OF INTERVIEW]

[0:48:48.9] TU: Before we wrap up today’s show, I want to again thank this week’s sponsor of the Your Financial Pharmacists Podcast, First Horizon. We’re glad to have found a solution for pharmacists that are unable to save 20% for a down payment on a home. A lot of pharmacists on the YFP community have taken advantage of First Horizon’s Pharmacist Home Loan, which requires a 3% down payment for a single-family home or townhome for first-time home buyers, has no PMI on a 30-year fixed rate mortgage. 

To learn more about the requirements for First Horizon’s Pharmacist Home Loan and to get started with the preapproval process, you can visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[DISCLAIMER]

[0:49:33.4] TU: As we conclude this week’s podcast, an important reminder that the content on this show is provided to you for informational purposes only and it is not intended to provide and should not be relied on for investment or any other advice. Information on the podcast and corresponding materials should not be construed as a solicitation or offer to buy or sell any investment or related financial products. We urge listeners to consult with a financial advisor with respect to any investment. 

Furthermore, the information contained in our archived newsletters, blog posts, and podcasts is not updated and may not be accurate at the time you listen to it on the podcast. Opinions and analyses expressed herein are solely those of Your Financial Pharmacist unless otherwise noted and constitute judgments as of the dates published. Such information may contain forward-looking statements, which are not intended to be guarantees of future events. Actual results could differ materially from those anticipated in the forward-looking statements. For more information, please visit yourfinancialpharmacist.com/disclaimer. 

Thank you again for your support of the Your Financial Pharmacist Podcast. Have a great rest of your week.

[END]

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YFP 309: Top 10 Tax Blunders Pharmacists Make


Sean Richards, CPA, EA, outlines the ten most common mistakes he saw pharmacists make throughout the most recent tax season. This episode is sponsored by First Horizon.

About Today’s Guest

Sean Richards, CPA, EA, received his undergraduate degree in Corporate Finance and Accounting, as well as his Master of Accountancy, from Bentley University in Waltham, MA. Sean has been a Certified Public Accountant (CPA) since 2015 and received his Enrolled Agent certification earlier this year. Prior to joining the YFP team, Sean was the Senior Treasury Manager at PRA Group, a global debt buyer based in Norfolk, VA. He began his career at American Tower Corporation where, over 10 years, he held several positions in audit, treasury, and accounting. As the Director of YFP Tax, Sean focuses on broadening the company’s existing tax planning and preparation operations, as well as developing and launching new accounting offerings, including bookkeeping, payroll, and fractional CFO services.

Episode Summary

The tax filing deadline is behind us so time to sit back and relax, right?! As YFP Director of Tax, Sean Richards, CPA, EA, tells us today, it’s important we are keeping tax front of mind year-round to avoid common blunders that show up during tax filing season. During this episode, Sean outlines ten of the most common mistakes he saw pharmacists make throughout the tax season including his thoughts on how year-round planning can help mitigate these mistakes.

Key Points From the Episode

  • Sean gives us his tax-season rundown.
  • The award for the most difficult state for tax returns! 
  • Sean takes us through ten of the most common tax mistakes made by pharmacists. 
  • The cause of the ‘unwelcome surprises’ and how to avoid them.
  • Not taking advantage of tax laws: energy credits.
  • Underestimating the power of the HSA; a grossly underutilized tool of the financial plan.
  • A good reminder about over-contribution.
  • Having someone in your court to help you avoid taking nonqualified IRA distributions.
  • Not saving for taxes when earning additional income.
  • Also for our side hustlers: not expecting the FICA tax on self-employment income.
  • Some of the mishaps and mistakes that have to do with employer-dependent care.
  • Not factoring in PSLF when choosing a filing status.
  • Reporting implications: overlooking considerations with cryptocurrency.
  • A bonus mishap: education around extensions.
  • How year-round strategy planning can help pharmacists optimize their tax situation.

Episode Highlights

“I know, taxes aren’t something that people love to think about and want to be excited about but it’s one of those things where if you sweep it under the rug, it’s not going anywhere, it’s only going to grow under there.” — Sean Richards [0:6:55]

“If you’re making money that’s outside of a W2, whether it’s investment income, capital gains, whether it’s a side hustle, really anything where you’re not seeing that federal income tax withheld line, you better be putting taxes aside or being ready to pay that at the end of the year.” — Sean Richards [0:21:45]

“Crypto is treated like an investment as far as the IRS is concerned. It’s like a stock.” — Sean Richards [0:31:39]

Links Mentioned in Today’s Episode

Episode Transcript

[INTRODUCTION]

[0:00:00.4] TU: Hey everybody, Tim Ulbrick here, and thank you for listening to The YFP Podcast, where each week, we strive to inspire and encourage you on your path towards achieving financial freedom.

On today’s episode, I welcome the director of tax, Sean Richards, back onto the show. Now that he has had a chance to take a breath from the last few months, working toward the tax filing deadline, I pick Sean’s brain about some of the most common blunders that he saw pharmacists make throughout the season and how year-round planning can help individuals not only avoid these mistakes but also optimize their tax situation.

If you’re looking to learn more about how YFP’s comprehensive tax planning service can help you and your tax situation, go to yfptax.com. Again, that’s yfptax.com Okay, let’s hear it from today’s sponsor, and then we’ll jump into the show.

[SPONSOR MESSAGE]

[0:00:48.3] TU: Does saving 20% for a downpayment on a home feel like an uphill battle? It’s no secret that pharmacists have a lot of competing financial priorities, including high student loan debt, meaning that saving 20% for a downpayment on a home may take years. We’ve been on a hunt for a solution for pharmacists that are ready to purchase a home loan with a lower downpayment and are happy to have found that option with First Horizon.

First Horizon offers a professional home loan option, AKA, a doctor or pharmacist home loan that requires a 3% downpayment for a single-family home or townhome for first-time home buyers, has no PMI, and offers a 30-year fixed-rate mortgage on home loans up to USD 726,200. The pharmacist home loan is available in all states except Alaska and Hawaii and can be used to purchase condos as well. However, rates may be higher and a condo review has to be completed. 

To check out the requirements for First Horizon’s pharmacist home loan, and to start the pre-approval process, visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[INTERVIEW]

[0:02:00.2] TU: Sean, welcome back to the show.

[0:02:01.8] SR: Thanks for having me. Yeah, it feels like it’s been a while but I think that’s just because tax season tends to you know, slow time down for some of us over here.

[0:02:09.7] TU: You look much more rested than I saw you just a few weeks ago. So here we are on the other side of the tax filing deadline. We’re going to talk all in this episode about some of what you saw this season with the hopes that pharmacists can prevent some of those mishaps as they work throughout the year on their taxes but looks like you’ve been – haven’t had a chance to maybe recharge and refresh on sleep. So how are you feeling post-tax of mine?

[0:02:34.3] SR: Yeah, I’m feeling great. I’ve been catching up on some of the things that have been put on side burners so to speak but definitely getting a little bit of sleep, catching up with the family and stuff. It feels good. I’m well rested, there are still some things to tie up from last year but ready to move forward and look ahead to next year and like you said, try to hopefully get some of these ideas in people’s minds so they can plan now and not have any of this kind of hiccups or roadblocks come up next year.

[0:02:59.5] TU: So give us the rundown. I know there’s still work to be done with some of the individual and business extensions and some of the more complicated returns but how many returns did you and the team do thus far?

[0:03:09.2] SR: We did over 200 federal returns and a similar number on the state side. So I mean, if you think some folks have multiple states, some people are in states that don’t have taxes so you know, you kind of, they work themselves out there but yeah, over 200 federal returns. We did a fair number of extensions, there are some business returns mixed in there, so it’s kind of all over the place but that’s the rough number between the few of us here.

So definitely, it feels like quite an accomplishment here but yup, I mean, definitely have some of those more complex returns that we want to give a little bit more TLC to, those are still hanging out there. So now that we’re past the big push, we can really focus and try to maximize savings for those folks. So excited.

[0:03:48.1] TU: Which state, Sean? Which state wins the award for the most difficult state when it comes to returns?

[0:03:53.3] SR: Boy, I don’t know if I’m going to be getting a misery love company or if I’m going to be jading people because I feel like a lot of our listeners kind of land in this territory where our headquarters are but I had to say, Ohio, probably gets the cake, Pennsylvania right up there, close second but yeah, those two are probably the worst I’d have to say. 

So again, hopefully, people aren’t sitting there saying, “I love those states” and if that’s the case, you know, all the power to you but not for me.

[0:04:20.8] TU: Yeah and one of the opportunities, challenges, depending on how you want to look with it, you know, we’ve got tax clients, financial planning clients all across the country, which is a unique opportunity and challenge when you think about all of the nuances that happen, especially in the tax side, right? On a state basis or even here in Ohio, we have the RITA, Regional Income Tax Authority, did I get that right Sean?

[0:04:43.1] SR: Yup, you got it right.

[0:04:43.9] TU: Which provides another wrinkle. So it’s fun to hear you and the team complain about Ohio and PA and you know, some of the other states perhaps are a little bit easier. So let’s jump into the most common mistakes Sean, that you and the tax team so far is just making and we’ve compiled these on our website, yfptax.com. If you want to download these and read a little bit more information on each one, please do that.

So we’re going to go through this one by one and again, the hope of this is that we really want to shift the perspective around taxes that the only time we think about taxes are April, when we’re filing, right? This really needs to be proactive year-round planning. We’ll talk more about that at the end of the show and that’s why we thought, “Hey, here we are in the month of May, tax season is over but this is not a, ‘Put it up on the shelf, worry about it ‘till next year.’”

This is the prime opportunity to really be learning from the season that just was and looking at the opportunities ahead of how can we best optimize the situation before we get back into the filing next year. Again, If you want to download a copy of the guide where we talk about some of these mistakes, you can go to yfptax.com and do that. So number one on our list Sean, perhaps the most common, I would presume, you can tell me if otherwise is folks that got a surprise bill or a surprise refund when they got to filing. 

So my question here is, tell us more but what is the usual cause of these unwelcomed surprises?

[0:06:14.7] SR: Yeah, I would say that’s the most common and it’s probably purely because if you take a lot of these other things that we’ll talk about, they all sort of work their way into that at the end of the day. You know, if you’re making a mistake, somewhere along the way, you’re probably going to end up with either a large bill or a large refund, so it kind of encapsulates everything.

Yeah, and just to kind of go back to your point before, this really is the best time to be looking at these things. I mean, any time of the year is good but when you’re coming off tax season, you might be disappointed or looking at things saying, “Oh, that didn’t go the way I hoped it would, I had a bill or I had the refund.” You don’t want to just kind of say, “Oh, finally, I’m done with it, we’re passed the 18th, I’m filed” and sort of shake your hands off and say because what’s going to happen is you’ll be in the same spot next year. 

I mean, I know, taxes aren’t something that people love to think about and want to be excited about but it’s one of those things where if you sweep it under the rug, it’s not going anywhere, it’s only going to grow under there. So yeah, the surprise bills and refunds, I mean, that can really be a litany of different things that can cause it. The biggest thing I would say probably by far is really just simply not withholding correctly at your job.

And this one frustrates a lot of folks and I don’t blame people because you know, people will say, “Hey, I’ve been at the same company for a while now” or “You know, my situation’s not that complex, how can they not be withholding properly?” and I have to say as a tax accountant, I don’t love the new W4 that the IRS rolled out a few years ago. If anyone working for the IRS is listening to this and they want to give me their opinion on it, feel free, my line is open because you know, I’m a tax accountant.

[0:07:43.0] TU: I don’t think we have many pharmacists that are IRS agents.

[0:07:44.7] SR: Oh hey, you never know, there’s a little bit of overlap here. You don’t have to be a pharmacist to listen to the pod but no, I mean, with that one, I just, I really wish there was a way as an accountant to be able to say “Hey, withhold 18% from this client, please. Just withhold 20% from this client” but it’s not that simple. I know what they’re trying to do, they want to make it more user-friendly where folks kind of can’t mess that stuff up, or if they don’t know how to come up with that number, it’s supposed to kind of guide you through it. 

So I think the biggest thing there is that the W4 is sort of designed to try to pick up everything else that’s going on in your financial life aside from just that one job that you’re working and typically, what will happen is folks will get married and they won’t update their filing status or they’ll get married or maybe not even get married but say, they already were married, their spouse gets another job. 

They have a side gig and these are all things that you know if your company – your system doesn’t really know that that’s happening, right? So if you’re making money off to the side, doing another job, you work multiple jobs, your spouse works multiple jobs, you know all those things factor into what your tax bill is going to be at the end of the day and if your company doesn’t know what’s going on then it can’t withhold properly and I say, your company, the payroll company was kind of doing all that stuff behind the scenes.

So that one is tough because there’s not a perfect answer. Really, the best way to do it is to take a look in the middle of the year and say, “Okay, where am I at, where was I at last year?” You know obviously if you had any kind of issues last year, you can submit a new W4 and how to change that but doing a projection midyear, take a look at what you’ve already withheld, what you withheld last year, and try to tweak that now, that’s definitely the best time to do it.

[0:09:19.1] TU: Yeah, and we’re going to come back to that topic Sean, of a mid-year projection, why it’s so important on the tax side as we get into the summer months. So stay tuned for more. Again, we’re going to be talking tax all throughout the year as we think it’s certainly an important part of the financial plan. So that’s number one, would be a surprise bill of refund at filing. 

Number two Sean, not taking advantage of tax laws. This makes me think of some of the recent changes that you’ve talked about before on the show surrounding the inflation reduction act, and the electric vehicle credits. I know this seemed to cause a fair amount of confusion and concern this year during tax season, and maybe some surprises as well. So what are you referring to here as it relates to not taking advantage of the tax laws?

[0:10:00.8] SR: Yeah, and with that in particular, I mean, we keep kind of harping on the energy credits but that’s where the tax law tends to be going now. I mean, all these things that are coming out, there are changes sort of across the board but the biggest piece and where the biggest dollar savings are tend to be these renewable energy credits, improvements to your home that are energy efficient, things like that.

And yeah, at the end of last year, the inflation reduction act went in and there was a lot of confusion as to which credits change when those credits change. So some of the electric vehicle stuff happened at the day that the law actually went into effect, whereas some of the other energy credits like home improvements like I mentioned, windows and things like that, didn’t really increase until this year, 2023 going forward. 

So there were folks who spent money last year and were expecting a larger credit for their taxes in 2022 and didn’t see that. So it’s really just, you know, it’s difficult to stay on top of the tax law, especially if you’re not a tax accountant or aren’t familiar with those types of things and especially if you want to stay out of politics too but it’s really challenging because it’s one of those things where if you’re not spending the money in the right timeframe, it’s not something you can go back and change after the fact. 

You know, if you put windows on your house now that’s a 2023 event. When we’re doing your taxes in 2024, we can’t say “Hey, I wish you had not done your windows because they’re already done.” So it’s something where it’s really important to make sure that if you’re spending money, thinking that you’re going to get a credit or you’re hoping you’re going to get a credit, really understanding when those things go into effect, what the dollar value is, and what the limits are. 

That’s another thing that some of these things, they’re increasing their limits but they do still exist. So you know, if you spend, USD 50,000 on an improvement, you’re not necessarily going to get a USD 50,000 credit.

[0:11:42.6] TU: Yeah, and we’ve got some info on this, yfptax.com, we’re going to be updating this throughout the year as well so make sure to check out the information there and Sean, this is just another testament to why the year-round planning is so important, right?

If we’re looking at this in the tax year, so here we are, now in 2023, obviously, next spring, spring 2024, we’ll be filing for 2023. At that point, right? Decisions have been made in terms of what happened during that year.

So are there adjustments that we can be making mid-year or are there tax laws and situations like this that we can make sure we’re up to speed or at least have the right understanding before we make some of these bigger purchases that may or may not have the impact that we’re hoping they’re going to have.

So that’s number two, not taking advantage of the tax laws. Number three, Sean. I have to say this one pained me a little bit because we’ve talked so much about this on the show.

[0:12:34.4] SR: So much.

[0:12:35.1] TU: Which is, underestimating the power of the HSA, the health savings account. You know, we’ve continued to emphasize how this – only has tax advantages but we still see this as an utter underutilized tool in terms of the financial plan. So tell us more about what you’re seeing here.

[0:12:51.8] SR: Yeah, I think with the HSA, it’s one of those things where people think, “Oh, I need to have a lot of medical expenses to take advantage of it. If I’m putting money there and I don’t use it, I’m not going to get the full advantage of it” but really, you need to not have that mindset and really think of it as a secondary retirement vehicle basically where if you do have expenses that you need to take advantage of it, it exists for you. 

But if you think of it almost as a second IRA or something like that, then it kind of shifts that mindset of, “Oh, I need to have these health expenses” but yeah, HSAs, I know, ad nauseum we talk about it but they have the triple tax benefit. You get the deduction for your contributions, you get tax-free growth and you get to take it out tax-free. So you rarely see that triple tax benefit. This is one of those ones where there is a little bit more flexibility. 

I just mentioned some of those credits and having to get the dollar spent during the year. You have a little bit of flexibility with the HSA where you usually have up until the filing deadline to actually make contributions or on the flip side and we saw a lot of this is people who work multiple jobs or got married in kind of weren’t talking to their spouse and over-contributed. So you want to make sure if you did that, you pull that money out so you avoid any penalties there.

And again, you have a little bit of flexibility after year-end to make those changes but to any extent you can avoid that, obviously, it makes sense but yeah, the limits are going up next year. I think 77.50 for a family plan, you have to be on a high deductible plan but if you are and you’re not taking advantage, you’re really just losing out on that benefit honestly.

[0:14:15.5] TU: Sean, I’m glad you mentioned the over-contribution mishap that might happen here and I think it’s a good reminder. Tim Baker was my ear, you know, anytime we talk about backdoor or Roth IRAs, he’s always beaten the drama of you know, really there’s a lot of nuances to consider and we see on the planning side, our planning team works with a lot of folks that you know, are trying to unwind some of the mistakes related to the backdoor Roth IRA contributions.

And I think it’s a good reminder that as there’s more and more information out there, right? We talk about HSAs, it’s readily available, something you can learn about that yeah, we still have to cross out Ts and dot our Is and I think having someone in your corner, right? Financial planners, tax professionals, perhaps both that can help make sure we’re executing this properly, really, really important. 

Number four on the list, Sean, taking nonqualified IRA distributions. We are talking before the show, perhaps maybe even a little bit broader than IRAs, tell us more about this one.

[0:15:09.0] SR: Yeah, IRAs are really just kind of retirement plans in general. I know we just mentioned HSA as they’re a sort of a secondary retirement vehicle but just not taking advantage or properly utilizing IRAs. So we’ll start with the IRA piece, there are a couple of different things there. You can get a deduction for traditional IRA contributions.

Folks typically phase out of that pretty quickly and then the next kind of phase-out level will be your Roth contributions and kind of what you were just alluding to is that folks also kind of pretty quickly phase out of that as well and that’s one of those things where you don’t want to end up at the end of the year saying, “Ah, you made too much money but you already contributed this to your Roth.” 

So now you’re going to go back and pull it out and then try to do the backdoor that Tim was talking about. So yeah, to any extent, again, you can have somebody in your corner where you can say, “Hey, this is what I’ve done so far this year, does this make sense? Am I going to over contribute, am I going to be in a good spot? Do I have room to contribute more?” Definitely make sense to do and again, you know the IRA limits are going up next year.

Again, the contribution limit. So taking advantage of that makes a lot of sense and the other piece that you didn’t really mention there but we kind of alluded to is just retirements in general. I mean, 401(k)s at people’s businesses, not taking advantage of those. You know, having extra cash on hand and not maxing out your 401(k) whether it’s a Roth to get the benefits in the future or a traditional to get that tax benefit now. 

I mean, either way, we saw a lot of situations where folks had a lot of cushion there and could have contributed more and that’s one where that at 1231, you can’t go back. So can’t turn back time, got to get those in before the year and again, having someone in your court to say, “Hey, you know, you’ve only contributed up to 30% of your 401(k) and we’re already in October, you might want to do some catch ups” is really important.

[0:16:47.8] TU: Sean, did you get a feel, I’m just curious, from folks that, if I heard you correctly, it looked like they’re wise margin there. They could have made those contributions or as cash on hand but didn’t. You know is that just a, “Hey, we overlooked it” or do you have a sense of you know, some of the volatility in the market, inflation, what’s going on in the broader economy, that there’s some hesitancy in the contributions into the retirement vehicles and people wanting to hold on to more of that cash.

[0:17:11.2] SR: It could be a lot of different things. I mean, it could also just be an education thing. I mean, I know, even when I first started out at a corporate job coming out of the school, you get all these different paperwork and everything and they say, “Here’s your 401(k), here’s this, here’s that” and you’re just saying, “Okay, I want to get the company match. Great, I’ll put this amount down and everything” and you don’t really realize that you have a limit that you can hit yourself and kind of capitalize on. 

So I think it’s really just a matter of maybe not looking at cash flow, like you were saying, potentially not taking a look at that in the middle of the year. I don’t think there’s a whole lot of hesitancy with the market or anything like that. I think it’s more just a matter of, you kind of set it and forget it and you know, you come to the end of the year and somebody says to you, “Hey, did you know that you could have knocked USD 5,000 off of your taxable income if you’d contributed more to your 401(k)?” and a lot of people just say, “I didn’t know that” so.

[0:17:59.3] TU: Yeah, yup. Seeing the numbers, right? I think in help and hindsight and you know, once you see the impact on the tax situation like, “All right, got it, point made, I’ll make that a correction for next year.” Number five, Sean, I think is one we have not yet talked enough about on this show, which is not employing a bunching strategy for charitable giving.

So here without talking obviously about donations and really looking at how to potentially alternate as you look at the standard deduction and then bunching these and those off year. So tell us more about this one.

[0:18:30.5] SR: Yup. So this one is more of a unique scenario. It’s one that we always take a look at but not everybody’s going to fall into this bucket but if you do, it’s something that if you’re able to take advantage of, it can be very, very powerful. So the idea of bunching is really trying to pull itemized deductions as much as you can into one year and then in the next year, not having as many and taking the standard deduction because it just getting higher and higher nowadays. 

I mean, just the number of folks that we see taking the standard deduction, even though they have things like mortgage interest and taxes that they’re paying for still taking advantage of the standard deduction because it’s so much higher. 

So yeah, if you’re looking at it and you say, “Hey, you know, I was USD 500 away from the standard reduction” or “I itemized USD 500 more than the standard deduction this year” and you had quite a bit of charitable contributions, if you’re able, again, sort of pull those in and say, “Hey, if I’m going to do a thousand dollars over the next two years, I’m going to do a thousand dollars this year and maybe not anything next year” and you can do it on 1231 so you kind of the same feel for giving to them that the charity.

But, if you’re able to do that and take advantage of it, it can be really powerful, and that way you’re not losing out. That was one thing we got a lot of is, “Hey, I have a house and I paid this mortgage interest but I am taking the standard deduction. So am I losing that benefit?” and it’s not the best way to look at it but you’re not really getting the full benefit if you’re doing it that way.

[0:19:50.1] TU: Yeah, as you mentioned, this really applies, not to say that everyone, depending on the amounts of folks are giving but especially for those individuals that are giving additional dollars to various organizations, churches, nonprofits, communities, et cetera, there could be some real benefits to the bunching strategy and I’m you know, one who is victim to this in terms of just behavior, right? 

Where you might have contributions on an automatic monthly payment or you’re planning for it throughout the year and you just don’t take the time to take a step back and say, “Okay, from a strategy standpoint, I’m going to do the standard deduction this year and then we’re going to do the bunching strategy next year.” So again, just some proactive planning to make this happen.

[0:20:31.6] SR: And it doesn’t always work for everybody because I mean, I talk to people who said, “Hey, that doesn’t match my giving strategy” and that’s perfectly fine.

[0:20:37.8] TU: Sure, yup.

[0:20:38.3] SR: It’s really just if you wanted to help out your financial strategy, there are options out there. I’m not saying you should change the way you give to your charities. It just exists, right?

[0:20:48.6] TU: Number six and number seven are specifically for folks out there that are earning some additional income, side hustling, business income. So number six, Sean, not saving for taxes when earning additional income.

It sounds obvious but we see more and more pharmacists that are dabbling in various side hustles, consulting businesses, so I think this is becoming a more prevalent mistake, probably one that maybe you make once and then you don’t make again but talk to us about what you’re saying here.

[0:21:16.4] SR: Yeah. So I mean, it does sound simple on the surface but again, if you’re not used to it or it’s not something that you’ve kind of done before, it’s not second nature, I guess. So right, if you, you know, you work a W2 job, that federal income tax is being taken out, hopefully correctly, although as I mentioned in the first thing here, sometimes it’s not correct but you know, hopefully, your income tax is being taken out at the end of the year.

You sort of do a true-up and maybe owe a little bit, maybe you get a little bit back but that’s that. If you’re making money that’s outside of a W2, whether it’s investment income, capital gains, whether it’s a side hustle, or really anything where you’re not seeing that federal income tax withheld line, you better be putting taxes aside or being ready to pay that at the end of the year and like you said, typically, that’s one where if you make the mistake, you don’t do it again in the future. 

But you know, I think some people are just really excited about making money and they want to pour the money back into their business, which is perfectly fine. You know, we want to encourage people to build their businesses and invest back in but just make sure you’re setting aside enough at the end of the year to kind of make sure you have at least a little bit of a cushion there and having somebody to do that calculation for you. 

Because you know, just because you’re going to – you think you’re going to net this much at the end of the year, doesn’t mean that that’s what your tax bill will be. I mean, there’s lots of ins and outs there, different things you can do. So having somebody to be able to take a look and say, “Hey, you know, as of right now, you’ve made 50k of non-withheld income so you’re going to want to put 20% of that aside, 25% of that aside, just be ready for it.”

[0:22:45.8] TU: Yeah, and I think there’s here, a couple of pieces you’re highlighting, right? Which are the mechanics of where do I save it, how much should I be saving based on how much I’m earning, and then at what point do I need to be making quarterly estimated payments and I do this, right? 

I reached out to you and say, “Hey Sean, we’re coming up on the Q1 estimated payment.” Like based on what we’re seeing in terms of the financial statements like, what’s the plan, and then we’re saving in a tax account along the way to be ready for those payments. So good thing, right? If you’re paying tax, you’re growing the business. 

[0:23:15.0] SR: Exactly and I will admit the IRS estimated payment process, it doesn’t really even feel that natural. I mean, you are kind of doing the math yourself, going onto the website and just saying, “All right, here it is” and they just take it and then at the end of the year, it does. It comes into your play, it’s one of the lines where you basically say, “Okay, what did you withhold? What did you pay in? What did you owe?” and we do the math on it. 

But it just feels like you’re sort of sending money out into the abyss when you make the payments. So I kind of understand that folks are a little apprehensive and would rather hold off but again, I mean, I’m conservative. I’m a tax accountant but at the end of the day, I’d rather get a little bit more money back than owe a lot of money. 

[0:23:55.0] TU: Yeah and Sean, a separate conversation for a separate day. This is a little bit more to the business strategy but one of the things that I like about withholding at least a quarter of it but at least on your own side even on a monthly basis is it forces you to look at the financials of the business a little bit more closely, right? 

So I think there can be a tendency if I am not paying tax and then I get either caught off by a surprise bill or I just wait until the end of the year and pay it, you know, you may fall into the trap of assuming your business is more profitable than it actually is and so really looking at what is the service, what’s the product you’re offering and what’s the true financials if you’re considering the tax. 

[0:24:31.1] SR: Not to go too far off but another big thing is that a lot of people kind of just assume that cash and profit are the same thing. 

[0:24:36.4] TU: Exactly. 

[0:24:37.1] SR: That’s not always the situation, right? So you could have a big profit at the end of the day but if you are pouring that cash back in, you might not have any cash on hand. So they don’t always go one for one and if you get away from that it can really end up causing some problems for sure. 

[0:24:51.7] TU: Preach it, Sean. We need to come back and do an episode on that, the difference between cash on hand and profit of a business, so that’s a good one. 

[0:24:58.3] SR: Yeah, that one, I’ll make a note because that could be like a double episode but yep, I’ll put that one on the back burner for sure. 

[0:25:04.7] TU: So that’s number six, not saving for taxes when you’re earning additional income. Number seven, also for our side hustlers and those that are running a business, not expecting the FICA tax on self-employment income. Tell us more about the FICA tax here. 

[0:25:17.7] SR: Yep, so that’s kind of similar varied, similar vein as to what we were just talking about really just having to kind of put that money aside but again, something that’s not second nature. It’s not something that you’d really be typically thinking about until you get into this and potentially make a mistake, hopefully not but right. When you have these W2 jobs and the money is being taken out, you’re withholding for yourself and you’re paying social security and Medicare, which we call FICA for yourself. 

Your employer is paying half of that for you whether you realize it or not and when you are self-employed, so you have a partnership or your own kind of business and you are getting that money in, you have to pay that portion of FICA yourself. Now, the benefit is that you get that employer portion that the employer typically would be paying for you on a W2. You do get that as a deduction, so it helps a little bit but yeah. 

I mean, that what was it? 15.7% or whatever for FICA is coming out of your bill at the end of the day. So on top of the regular income tax you have to set aside, you should really be saving for that as well. That’s where you’ve heard me say before, you know, 20, 25%, maybe up to 30% depending on what your bracket is, you start to add that FICA in on top of it and you could be looking at quite a bit to be setting aside. 

[0:26:27.6] TU: Yeah Sean, this was one I would add to this as well. You know, the surprise of the cost of health insurance. This is one as well, you put those together and you go from a W2 job to running your own business is like, “Oh, okay.” So again, right? You’re looking at the financials in a very different way. 

[0:26:44.5] SR: Yep, exactly. Things to keep in mind. 

[0:26:46.8] TU: Number eight, Sean, has to do with some of the mishaps and mistakes with employer-dependent care. Tell us more about this one. 

[0:26:53.3] SR: Yeah. So there is a lot of different things with dependent care benefits that you can add to dependent care FSA. So it’s a little bit different than the HSA but with that, that one really is a little bit more of the, you know, I was saying with the mindset within HSA, “Oh, if I don’t have medical expenses and I don’t use it, you know it’s not going to be worth it for me.” It turns into an investment vehicle if you don’t use it. 

Dependent care FSAs, flexible spending accounts, if you have cash in that, that is more of an “if you don’t use it, you lose it” kind of thing. So that is something where if you’re pushing cash aside, they are pre-taxed dollars. You want to make sure you are using that for dependent care expenses during the year and the other thing is that if you are getting benefits from your company, you want to make sure that you are also putting that and actually spending that on dependent care. 

When I say that, I mean a nanny or a daycare or even if it’s a family friend but somebody that you’re putting their social security down and saying, “Hey, I paid this person this much money to watch my children” otherwise, that can become a taxable event. So you want to make sure that if you have kids, you’re getting these benefits, that you are utilizing the cash during the year and not kind of ending up with excess in those accounts at the end of the year exactly. 

[0:27:58.9] TU: Number nine Sean, an oldie but a goodie, one that I think has lots of attention given the three-year loan pause and that is, not factoring in PSLF when choosing a filing status. Tell us more about this one. 

[0:28:11.3] SR: Yeah and this one, I mean, you just eluded to it. It’s been very, very challenging, especially with the client base that we work with having that ambiguity on what’s going on with the loan system and trying to give guidance on this front because it’s really tough when you’re saying, “Hey, we’re not exactly sure if they’re going to turn back on and how all that looks and when we’re going to have to recertify all these things.” 

But yeah, what we’re talking about here is that typically when folks get married, if filing joint tends to be the best approach there and we always do a comparison at least on our side to say, “Okay, you know all else equal from an objective tax standpoint, filing jointly will save you X number of dollars versus filing separately” but when you are talking about PSLF and you get into these income-based repayment plans and are looking at AGI, that can really swing very, very rapidly between what your AGI is as merely filing separate individual versus your combined AGI with your spouse when you’re filing joint. 

So this is one where it’s a classic like you just mentioned Tim Baker, the old “it depends” really depends on your individual circumstances here. You’re going to want to look and say, “Hey, what do I have on my side? What does my spouse have on their side? If you separate us, what does that look like? What is my income base repayment plan? What numbers are they looking at?” and really like we just said, “When do I have to recertify these things?”

“When am I going to have these payments?” because it’s a matter of you could save $200 by filing jointly this year but if you are saving $50 a month on your payment by filing separately, that adds up very quickly. So it’s something where there’s a lot of moving pieces but it is something where if you are not looking at those pieces, you can very, very quickly end up spending a lot more money than you think. 

[0:29:49.3] TU: Yeah and it is so important. You know, we’re talking about PSLF here but the intersection of student loans and the tax strategy is one of many examples where the financial plan and the tax plan need to be jiving, and this example specifically brings us back to the origins of FYP Tax, right? I remember Tim Baker talking about, “Hey, we would develop these beautiful student loan repayment strategies and plans.”

Then they’d be, “Hey, go talk to your accountant” and not all accountants are well-versed in student loans, which is fair, right? Based on how nuanced they are and right now, how rapidly this information is changing. So shoutout to you Sean, the YFP Tax team, you know working with a tax prepare, working with an accountant that understands student loans. Again, this is just one example but really, the intersection of the financial plan and the tax plan is so important that those are jiving in the same direction. 

[0:30:39.8] SR: Yeah and like you said, I mean, not all accountants know about it and I know enough to be dangerous with it but you have to have financial planners that know about that too. I mean, that is something where I could be working with you and say, “Hey, I think from a tax standpoint it looks like this” and you could go bring that to your planner, and if they’re not really thinking about these implications, they can really get away from you quickly, you’re right. 

[0:30:58.3] TU: Number 10 on our list of ten common mistakes, mishaps that pharmacists were making during the most recent tax season is overlooking considerations with cryptocurrency. I mean, what would be a tax episode if we didn’t talk about crypto in digital assets, so what do we see here? 

[0:31:12.4] SR: Well, this one probably is a little bit different than we’ve seen in the past with crypto. It wasn’t so much that we are seeing people with these big gains that they were necessarily expecting. In fact, if anything it might have been the opposite given what kind of happened with the market and everything last year but in that and what I would say with that is you know, if you kind of take the gain-loss implications aside, the biggest thing I would say here is just the reporting aspect of it.

So cryptocurrency again and I feel like I harp on this all the time is crypto is treated like an investment as far as the IRS is concerned. It’s like a stock, so if you go and you’re doing all these microtransactions all the time and you’re using your crypto wallet to buy coffee down the street, that is effectively saying, “Okay, I’m going to sell X number of shares at this price on this day” whatever I bought it for back in the day that same security. 

You need to look at what your basis was and do the math, so if you are doing hundreds and thousands of these transactions every year, the reporting implications are significant and that’s not something where you can say and I am not just saying this because I’m an accountant, I’m biased where you can’t just say to your accountant, “Hey, here is my list of a thousand transactions, you know, figure it out for me.” 

You need to make sure that whatever system you’re using can spit that out in a digestible manner whether it is actually getting a form from the IRS or kind of getting a summary and one thing that we have seen is in a lot of these companies and I don’t blame them necessarily but a lot of them will kind of rope you in and say, “Hey, you know it is going to cost you five dollars a month for the basic crypto wallet” and everything like that. 

Then you get to the end of the year and all the tax forms that you need will be kind of an extra charge and you are not thinking about it and folks will say, “Well, I have an accountant, they can kind of do that for me” but I mean, again, and I am not just saying that because I don’t want to do it. It really is a matter of an accountant simply can’t take thousands of transactions and stick them onto a form. 

It is not a practical thing that can happen. So you want to make sure that whatever you’re doing and again, if you want to do all those transactions, hey, power to you but keep in mind it’s like you’re selling shares. You need to make sure you are getting something out of your system that an accountant can then use and file your taxes with because it’s not like spending money. It’s like selling stocks. 

[0:33:19.6] TU: Yeah, I am hopeful Sean, this is another one you know, where you can make this mistake once and you maybe approach it differently in the future, right? I think this is an education where your explanation is spot on. If we look at this in the eyes of the IRS, which is that we’re making a transaction in terms of like we were selling stock and especially if we’re using it to purchase things on a daily basis, right? 

A store, a cup of coffee, groceries, whatever like we don’t think about our stocks like that typically and so I think that — not to say people may not transact crypto for purchases just like you would dollars out of a brokerage account but maybe not on the frequency that it’s happening if you are able to think of it in that way and understand the reporting and the tax implications there, so great explanation. 

[0:34:04.6] SR: Exactly. I think like I said, that the basis is really the biggest thing and I, you know, people, if you talk to me you’ll hear me say it all the time and you’re probably sick of it but it is really being able to trace back and say again, like it’s like a stock, right? So if I sell XYZ NFT today, I need to make sure I know what I purchase XYZ NFT for in the future, and when you are doing all these things and you’re day trading so to speak, and saying, “All right, I am going to flip this one here and I’m going to go buy crypto with this one” and kind of moving, each one of those things has to be kind of traced back to the origin. 

If you don’t have that information, you could end up paying more, honestly. You know, if you don’t have the basis information and you are just going to end up sell, reporting it on your sale price and not have the basis in there, you can end up either paying more or again, reporting incorrectly. Both of those are not what we’re hoping for in our side at least. 

[0:34:55.9] TU: So if anyone heard Sean correctly as I heard him, all of your handwritten crypto transactions, your reports, your chicken scratch, you can email those to [email protected]. He will gladly – just kidding. 

[0:35:07.8] SR: Yep, I will go through all of it in all of my free time now. Absolutely, I will break it all down for you, please. 

[0:35:14.0] TU: Awesome. So that’s our ten common mistakes that you saw pharmacists making throughout the tax season. Can I add one more? We’re going to do a bonus round here for a moment and – 

[0:35:22.5] SR: Yeah, go for it. 

[0:35:23.2] TU: I think we need to do some education around extensions, right? I think this is an area where I know firsthand the first time I extended several years ago and I have gotten used to that practice now. It can feel uncomfortable, am I doing something wrong, does that mean I’m delinquent? But as you eluded to at the beginning of the show, there are some extensions that are happening with the more complex returns. 

We want to make sure that we have the time that we need. The misperception I think, I could be wrong, that’s out there is extension means bad or extension means delinquent but that’s not the case, right? So tell us more about the use of extensions and why they may be appropriate. 

[0:36:01.9] SR: Yeah, glad you’re giving me the bonus round. I would have had this as 1-A on my list if I would have thought that you would have actually allowed me to record this podcast if I did that. I thought that I came over the top of that one, we might be deferring this recording out to a future date but no, extensions, yeah. So it is actually kind of twofold. I would say that from who I’ve talked to and this could be clients. 

I mean, even family members that I was talking to during the tax season, checking up on how things are kind of going, I would say with the negative connotation, it’s one of two camps. It’s either, “Hey, the extension means bad and delinquent” or extension means, “Hey, I’m this crazy tax guy who has offshore accounts and you know, I make five million dollars and I need to have my accountant spend the extra time to do all of this stuff.” 

Those are really the two mindsets that I got a lot of. I mean, like I said, I talk to people that I know, I’ve known for a long period of time who I consider to be financially sound individuals and they said, “Oh extensions, those must be for your big ticket clients, right?” and the answer is not really. I mean, extensions simply give us, your accountant, and you more time to get your things together to allow us to dedicate the time to find you tax savings, get your things right, and not rush them. 

I mean, I know Paul, my team who I’m sure you’ve heard talk on this pod before but he’ll always say, I mean, if you have a surgeon who needs to do a thousand surgeries in a year, would you rather him do them all in three months or her do them all in three months or have them do it throughout the course of the year, you know, with X number during each month. So you got me all fired up because you know, extensions are near and dear to me. 

But I mean, really what it comes down to is we’re trying to do a lot of different returns and a lot of people have very complex situations but we want to make sure we get it right. We talked about states and local, moving states, and making sure states don’t talk nice to each other even ones that border each other are not – don’t always agree with how things are picked up and everything, and just getting all that information together, making sure we can parse through it, maximize your tax savings and everything, extensions just give you the time to do it. 

Now, the one thing I will say is it does not extend your due date to pay. That’s the biggest thing. So what you want to do is get an estimate, and make your payment if you think you are going to owe or in April or even beforehand but after that’s done, it really is a one-click kind of thing. It’s an automatic extension, once you do it, it’s six months. You get until October and that’s that. It really is not for delinquents. 

It is not for folks who didn’t get their stuff in on time or like I said, are using offshore accounts to do X, Y, and Z. It’s just simply to give your accountant more time to get it right. 

[0:38:41.5] TU: Well, thanks for allowing me to throw some kindling on the fire, so I appreciate that. 

[0:38:45.3] SR: Thank you, I appreciate that. 

[0:38:45.8] TU: You know, I think it is a good reminder not only in the perception of it but also you know, some folks may hear this and say, “Well, you know there is an opportunity cost that if I am getting a refund” and we don’t file that for three months, four months, five months later, whatever that those dollars could have been used elsewhere. True but my counterpoint to that would have been, one, if we are planning correctly throughout the year, we shouldn’t be expecting a massive refund. 

Second to that would be is that most often, extension doesn’t mean we’re buttoned up against the October deadline. It means that maybe instead of April 18th, it’s May 1st or 15th or even the end of April or into later in May or early June, whatever. So you know, it allows kind of that stretching out of the season to make sure that we’re doing the job that needs to be done, be done well, we are optimizing the situation. 

I think that certainly for folks that have more complicated returns, I think what we’re seeing in the industry in my perception even with an accountant we used to work with before building our own practice internally was, “Hey, you’re a small business owner. Hey, you own a bunch of real estate” hey, whatever like you’re automatically extended. You know, that’s just kind of the process of what they do to make sure that they have the time to do those returns well. 

[0:39:55.5] SR: Right and like you said, the idea of year-round tax planning is you’re working with your accountant throughout the course of the year. You are getting the information, you have rentals, you’re getting them, “Hey, I sold this place in November” and you are giving them the information in November so your accountant can already have that stuff ready to go and it’s not a situation of you’re in March and you say, “Hey, I forgot” or “FYI, sold my house back in January of last year. Here’s the 5,000 documents for it. Can we get this filed next week?” 

The answer is, I mean, we probably can but you know if we are thinking about these things ahead of time, we can spend the time that we think it deserves to get everything right, and if you are doing that planning throughout the course of the year, you can get 90, 95% of a tax return effectively done through the conversations that you’re having with your account throughout the year. So yep, absolutely. 

[0:40:40.4] TU: So Sean, let’s wrap up by talking through how the year-round planning can help pharmacists not only prevent these mistakes but again, better yet optimize your tax situation. That really is the focus of what you and the team are doing through the comprehensive tax planning, what we refer to as CTP. Again, not just that transactional return month of April, got to get it done but really that year-round strategy and planning. 

So you know, what is comprehensive tax planning? What do we offer? Why is it needed and who is it for and perhaps, not for as well? 

[0:41:11.3] SR: Yeah. So comprehensive tax planning is designed to really attack everything on this list, right? So it’s where you’re doing proactive planning and thinking about your tax situation now and not at the end or not in the beginning of next year looking back on this year and again saying, “I wish I could have done this” or “How could I have done this differently?” It’s getting ahead of those things now so you don’t have to worry about that. 

So things like mid-year projections, “Hey, let me grab your paystub, let me talk about some of those side gigs you’re doing, give me an updated PNL” or even if we’re doing your books for you, I’ll pull down the updated PNL and we’ll take a look. “Hey, you know you’ve withheld this much money so far, your side gig is going to make this much money we think so far. Have you put that money aside yet? Did you make an estimated payment?” 

“I think you should make a payment of this much” checking in on those things or being able to have the conversations of you know, “Hey, I just bought a rental property. Tell me about the short-term rental loophole” or “Tell me about what it’s going to take for me to be considered a real estate professional and be able to offset some of my active income with this passive income” or “Hey, I just bought the rental and hearing all about all these tax credits.” 

“How does that work? How do those tax credits affect my personal return and then how does it affect my rental property? Are those going to be different? Can I maximize them?” These are the conversations that we’ve been having with folks over the past few months looking back on last year but proactive tax planning is you’re having these conversations now. You are having them in May, June, and July and getting ahead of these things. 

So when we talk about March and April that big push, it is really a matter of, “Hey, did we do what we say we’re going to do? Excellent, great. Okay, what are your tax bills? Zero. As expected. Awesome, file? Done. Food to go.” Just really having that phone-a-friend CPA to ask questions for, “Hey, you mentioned bunching when we looked at my return last year. You said I was close to the itemizing. How can I actually employ that now?” 

Or “Hey, this is what I’ve contributed in my 401(k) so far this year, do I have room to add more?” things like that. Just getting ahead of it now while there’s room to make changes and not looking back and saying, “Ah, I really wish I did that.” 

[0:43:19.9] TU: Great stuff. So you know it’s again, not only that finally and it’s the mid-year projection, it is having an accountant in your corner to make sure you are executing throughout the year, answering those questions as they come up. So folks can learn more at ypftax.com. You can read more about that service, you can book a free discovery call to see whether or not it’s a good fit for your personal situation. 

And again, whether you came off the season and you’re like, “Hey, I did that myself and I never want to do that again” or you were surprised by a refund or a bill or perhaps you have a situation that’s changing, right? It could be moving, a new job, dependents, acquiring real estate, or building a small business, all are these I think there’s a few examples of things that we want to be thinking about in planning throughout the year. 

So again ypftax.com, you can learn more and book a free discovery call to see whether or not that’s a good fit. Sean, thanks so much for taking the time. I appreciate you coming on the post-tax season and looking forward to having you on throughout the year. 

[0:44:15.6] SR: Yeah, thanks, Tim. Glad to be back and hopefully next time, we’ll be able to talk more about some of these backburner items. So I am looking forward to it. 

[0:44:22.1] TU: Awesome. Thanks, Sean. 

[0:44:23.1] SR: Thanks. See you. 

[END OF INTERVIEW]

[0:44:25.3] TU: Before we wrap up today’s show, I want to again thank this week’s sponsor of the Your Financial Pharmacist Podcast, First Horizon. We’re glad to have found a solution for pharmacists that are unable to save 20% for a down payment on a home. A lot of pharmacists in the YFP community have taken advantage of First Horizon’s pharmacist home loan, which requires a 3% down payment for a single-family home or townhome for first-time home buyers and has no PMI on a 30-year fixed-rate mortgage. 

To learn more about the requirements for First Horizon’s pharmacist home loan and to get started with the preapproval process, you can visit yourfinancialpharmacist.com/home-loan. Again, that’s yourfinancialpharmacist.com/home-loan.

[DISCLAIMER]

[0:45:10.4] TU: As we conclude this week’s podcast, an important reminder that the content on this show is provided to you for informational purposes only and it is not intended to provide and should not be relied on for investment or any other advice. Information on the podcast and corresponding materials should not be construed as a solicitation or offer to buy or sell any investment or related financial products. We urge listeners to consult with a financial advisor with respect to any investment. 

Furthermore, the information contained in our archived newsletters, blog post, and podcast is not updated and may not be accurate at the time you listen to it on the podcast. Opinions and analyses expressed herein are solely those of Your Financial Pharmacist unless otherwise noted and constitute judgments as of the dates published. Such information may contain forward-looking statements, which are not intended to be guarantees of future events. Actual results could differ materially from those anticipated in the forward-looking statements. For more information, please visit yourfinancialpharmacist.com/disclaimer. 

Thank you again for your support of the Your Financial Pharmacist Podcast. Have a great rest of your week.

[END]

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YFP 290: Getting Ready for Tax Season


Sean Richards, CPA, EA returns to the podcast to discuss difference between tax planning and tax preparation, how effective tax planning can prevent costly mistakes, tax changes for 2023, and the basics of YFP’s Comprehensive Tax Planning. 

About Today’s Guest

Sean Richards, CPA, EA, received his undergraduate degree in Corporate Finance and Accounting, as well as his Master of Accountancy, from Bentley University in Waltham, MA. Sean has been a Certified Public Accountant (CPA) since 2015 and received his Enrolled Agent certification earlier this year. Prior to joining the YFP team, Sean was the Senior Treasury Manager at PRA Group, a global debt buyer based in Norfolk, VA. He began his career at American Tower Corporation where, over 10 years, he held several positions in audit, treasury, and accounting. As the Director of YFP Tax, Sean focuses on broadening the company’s existing tax planning and preparation operations, as well as developing and launching new accounting offerings, including bookkeeping, payroll, and fractional CFO services.

Episode Summary

This week on the YFP Podcast, YFP Co-Founder & CEO, Tim Ulbrich, PharmD, welcomes Sean Richards, CPA, EA, back to the podcast to discuss getting ready for tax season. In their conversation, Tim and Sean discuss the difference between tax planning and tax preparation, how effective tax planning can prevent costly mistakes, tax changes for 2023, and the basics of YFP Comprehensive Tax Planning. Listeners will hear ways to prevent costly mistakes during tax filing season, including building a strategy around PSLF, nuances of real estate investing, and the impact of a side hustle or additional business income. Sean explains that the best way to avoid these mistakes would be through proactive tax planning throughout the year, but in particular, before tax season. Tim leads the conversation to the differences between tax planning and tax preparation, plus various tax changes for the 2023 tax filing season and into the future. Sean shares resources and information on changes to charitable contributions, energy credits, and clean energy credits. Sean closes out the conversation with an introduction to YFP Tax, the new YFP Tax website, and the various services available to clients including YFP’s Comprehensive Tax Planning (CTP), what it is, and the type of client the service would be a good fit for. 

Links Mentioned in Today’s Episode

Episode Transcript

[INTRODUCTION]

[00:00:00] TU: Hey, everybody. Tim Ulbrich here, and welcome to this week’s episode of the YFP Podcast, where each week we strive to inspire and encourage you on your path towards achieving financial freedom. 

Now, aside from being pharmacists with a passion for personal finance, there’s something else that you and I have in common, and that’s that we have to file our taxes each year. Now, I know what you might be thinking. Tim, it’s only January, and the tax filing deadline is still a few months away. 95 days to be exact, in case you’re counting. Do I need to start thinking about taxes right now? 

I get it. But the truth is that now is an important time to shift gears and start thinking about the strategies that you can use to optimize your tax situation, and that’s why I’m excited to welcome back onto the show YFP Director of Tax, Sean Richards, to talk through getting ready for tax season. We discuss on this episode the difference between tax planning and tax preparation and how effective tax planning can prevent costly mistakes. To learn more about the services offered by YFP Tax, you can visit yfptax.com. 

Now, whether you’re looking for help with your individual taxes, business taxes, or both, YFP’s comprehensive tax planning combines traditional filing with our proactive year-round planning process. All right, let’s jump into my interview with YFP Director of Tax, Sean Richards. 

[INTERVIEW]

[00:01:22] TU: Sean, welcome back to the show.

[00:01:24] SR: Thanks for having me, and I’m excited to be here before we get into tax season, while I actually still have a chance to get on the pod and talk to you. 

[00:01:31] TU: Absolutely.

[00:01:32] SR: Catch me in a couple of weeks, and I’m probably going to ignore all of your calls and everything. So get me while you have me.

[00:01:37] TU: Tis the season indeed. We had you on episode 283 not too long ago. We talked about how to optimize your tax situation as a pharmacy professional. We’ll link to that in the show notes for folks that want to go back to that. But as you mentioned, here we are in the midst of tax season, this episode going live right around the middle of January. Sean, this is about the time where we start to see those tax forms coming in the mail. I don’t know. Folks maybe are like me, where I start to pile those up on my desk. Maybe clutter the –

[00:02:06] SR: [inaudible 00:02:06] or whatever. 

[00:02:09] TU: Clutter the countertop a little bit. It’s that visual reminder that we’re going to be filing our taxes. One of the things we’re going to talk about here today, not only what are some things that folks can do to, hopefully, have a smooth tax filing season, but also how can we be strategizing and planning, hopefully, year round and not necessarily just house on fire when we go to file our taxes each April. 

So we’re going to talk in really a few different parts. Number one, what are some of the ways that folks can prevent some of the costly mistakes during filing this season? What are some most common mistakes that you see? We’ll then talk about some of the differences between tax preparation and tax planning. Then we’ll talk about some of the changes that folks need to be aware of for both this tax filing season, some of those coming from the Inflation Reduction Act, and then also some of the things that folks can be looking out for into the future. So I’m ready if you’re ready. Should we do this?

[00:03:07] SR: I’m always ready. Like I said, this is the most ready I’ll be for a while. So here we go.

[00:03:12] TU: So let’s jump into some of the costly mistakes that folks may find themselves making during the filing season. Obviously, we want to avoid this if we can. You recently wrote a blog post on this topic. We’ll link to that in the show notes. But give us some of the examples, as you’ve been talking with many pharmacists that are interacting with YFP Tax, many pharmacy clients. What are some of these examples of mistakes that are being made that if we had some more proactive planning, perhaps we could prevent it?

[00:03:43] SR: Yeah, and thanks for bringing up that blog post because that really gets into the nature of how a lot of these kind of arise and can be prevented. Not to give everything away about that, but the idea of the whole thing is really just sort of being able to go back in time, if you could, right? In a lot of circumstances in life, it would be nice to be able to get a redo and be able to go back and kind of get a mulligan, if you will. But with a lot of things in life, you can’t do that, and taxes are one of those things. 

So I would say the biggest examples where I see pharmacists or anybody really making mistakes when it comes to taxes is not planning ahead and kind of looking back and saying, “Oh boy. I wish I had done that.” So that time that you had a great year, and you made a ton of money, and maybe you’ve had a side gig going, and you had so much cash that you didn’t know what to do with it. But then you come to the end of the year and you didn’t have that cash anymore when your actual tax bill comes due. So, “Oh, I wish I could have put some of that money aside, done a projection, see what I’m going to owe at the end of the year.” Maybe make estimated tax payments if you apply for something like that. 

Or something like, “Hey, real estate’s hot right now.” You bought up a place. You fixed it up. You finally sold it. You hit that peak before interest rates went up, and now you’re sitting there going, “Oh, my goodness. I have to pay taxes on all those capital gains.” What are some things you could have done to maybe make different improvements to the house or take advantage of those improvements against your bases when you’re calculating the taxes? Or, “Hey, maybe I could have invested in some solar property or something.” Take advantage of some of those credits that we’ll talk about with the Inflation Reduction Act. So things of that nature. 

A big one with pharmacists is loan forgiveness, right? PSLF. If you’re looking at this, and you’re saying you did your taxes, and you’re going to apply for forgiveness in the future and say, “Oh, maybe I could have filed separate for my spouse last year. If I had done this a little bit differently, then maybe I could have had some more of my loans forgiven.” So it tends to always be an – I’m not going to say always, but there tends to be a common recurring theme of if I just planned ahead, and I could go back in time and change these things, maybe that problem wouldn’t be there. 

But actually, now that I think about it, I had a personal situation. I like to bring this one up because it’s near and dear to me and if I can ever prevent folks from having the same thing. I know, early in my career, I was lucky enough to have RSUs given, granted to me, and I was a young budding accountant and went to do my taxes and paid the capital gains and said, “Okay, that’s fine. I understand. I cashed them in. I have my capital gains.”

It wasn’t until I was looking at it a little bit down the line and talking to some of my colleagues that I realized I didn’t actually account for that properly. I had already paid taxes on some of that, and then I went and basically double-counted and paid again. So RSUs are one of those things. I know a lot of pharmacists get them. They get excited about them. If you don’t really pay attention or you don’t talk to somebody who knows what they’re doing with these things, you can end up double paying, and the IRS certainly won’t reach out and let you know that you did that. You have to find that on your own.

[00:06:44] TU: Yeah. Sean, to that point, we’ve worked with a lot of the pharmaceutical industry fellowship programs, and as a result, have a handful of those that are in pharmaceutical industry as clients, whether it’s on the planning side or on the tax side. So this is something that we see come up a lot about trying to understand what are RSUs, and what are some of those tax implications. Certainly, student loans, you mentioned PSLF strategy. It’s a big one in our community, real estate. We’ve got a whole separate podcast dedicated to that topic. So of course, that can be something that’s top of mind.

Then the first one you mentioned is something, Sean, I know I’m seeing and hearing more and more of. We featured many pharmacists on the show that are beginning to monetize their clinical expertise in a variety of different ways, whether that’s a business, whether that’s a side hustle, or perhaps a side hustle that turned into a business. As you mentioned, often there’s that new income that’s coming in. By the time we get around to filing, we’re maybe putting that income back into use in the business or other expenses that come up. Then there’s that surprise tax bill. So, yes, we’re doing good. We’re growing the business. We’re achieving that goal of monetizing whatever we’d been working on. But are we proactively planning for, obviously, the tax bill that’s going to be due? How can we plan for that throughout the year? So great examples I know that will touch many people that are listening. 

The next question then is what is the antidote to these mistakes? You mentioned a couple times you were sharing that really that more proactive tax planning, not just necessarily looking at that point of filing, where we’re looking backwards, but really thinking strategically throughout the year can help us not only prevent these mistakes, but also optimize our overall tax strategy. So define for us the difference of tax planning versus tax preparation, and why it’s so important that we understand how these two are so different.

[00:08:36] SR: Sure. So tax preparation is the traditional what you think of with taxes. It’s, hey, you go to your account at the end of the year. You hand them a big box of receipts and say, “Here’s all the stuff.” All the things that you were just talking about you get in the mail, you put a little pile on the table, you bring it to your accountant and say, “These are what I have. This is what I did last year. Get my taxes done for me.” 

That also is the traditional area where people kind of are fearful about taxes or have that stress like, “Oh, my goodness. Am I going to owe something?” Or even getting a big refund can be a good thing. But at the same time, you just gave the government an interest free loan for however long, right? I mean, getting a big refund, there’s probably a pretty good chance you could have done something better with that cash. So that’s typically the surprise or the idea I was talking about like, “Oh, goodness. I wish I had done that in the middle of the year in July,” something like that. 

That’s tax preparation, and it’s not inherently a bad thing. It needs to get done. Again, it’s what most people are familiar with, whether it’s going to an accountant or going on to TurboTax yourself and getting it done. But that also, again, is where a lot of these stresses tend to come from. On the flip side of that is this idea of tax planning. So that is not just thinking about taxes at the end of the year, but making sure that you’re keeping them top of mind throughout the course of the year, and you’re synergizing your tax strategy with your overall financial strategy. 

One thing I want to be clear about is I don’t want people sitting there all day long thinking about tax because, I mean, maybe I want to do that. But a lot of people don’t, and that’s not what we’re getting at with tax planning. It’s not where you’re sitting there all day long and how is this going to impact my taxes? It’s just making sure that when you’re making decisions, that it’s not something that you’re thinking about in April or next filing season. But it’s something that is in your mind. So, hey, I’m thinking about buying a property at the end of the year. What will those implications be from a tax standpoint? Or I’ve been working this side gig. Should I be putting cash aside and trying to plan ahead and everything? 

One analogy, if you’ve ever heard me on the pod, I think I talked about this before. If you’ve ever talked to me in person, you’re probably sick of hearing this one. But I often compare it to tax preparation at the end of the year. It’s like a film editor versus tax planning. It’s like a film director who can kind of change things over the course of the year. A new analogy I’ll kind of introduce this time around, I’m really into cooking. So what I found it to be is tax planning is sort of like reading the recipe, prepping your ingredients, getting everything kind of ready to go. Like you watch these tasty videos. They all have everything measured out, and they’re just pouring it in at the time, and it’s all kind of ready. 

Versus tax preparation is the last step of getting everything plated and putting it all together. Would you want to do all that piece, without having done any of the prep work to begin with? Are you going to try to throw everything together when you haven’t even cut the potatoes or anything yet? No. I mean, ideally, if you’re preparing a meal, you want to also plan, cut the things, read the recipe, and just have a good idea throughout the course of the thing. So that’ll be my new analogy going forward maybe until I get sick of cooking, and then I can come up with something else.

[00:11:35] TU: I’m smiling because I can totally see you this past weekend cooking and thinking, “Oh, I’ve got another analogy for how I’m going to explain tax planning versus tax preparation.” 

[00:11:45] SR: Exactly. I was probably panicking and realize I didn’t cut something ahead of time that I needed to put in and was saying, “Oh, my goodness. If I had just done that ahead of time and made the connection there.” Most likely, this would happen.

[00:11:55] TU: Yeah. I think you’ve given some really good examples, Sean. I was thinking about this this morning. Even when I was working a W-2 job, a pretty simple tax return, pre-kids, there still was this kind of underlying feeling of like, “Am I really optimizing everything?” What I don’t know, I don’t know. Number one, yeah, I could do the TurboTax. I could do the H&R Block. I could figure that out. But how is this really interfacing with the rest of the financial plan? Then, obviously, over time, as things become more complicated, more than one income perhaps or rental properties or children enter the equation, changes of income throughout the year, all these different scenarios where there’s some real time adjustments that you want to make, as well as how can we look at all these things across the plan to make sure we’re optimizing this in the best way we can. 

Sean, you know this because you’re my phone a friend on the tax side. But probably once a week, once every other week, it’s a, “Hey, I’ve got this notice. I’ve got this question. What about this? What’s it looking as we’re thinking about the estimated payment, whether it’s on the business income or question related to the real estate piece?” So there’s just so many things going on, and I feel like I have a high level understanding. But there’s a whole another layer of depth that, obviously, you and others with this expertise have and can really advise people to be thinking across the entirety of what’s going on with the taxes and the financial plan. But also looking at how can we be more proactive than just simply doing the filing each year.

[00:13:24] SR: Yep, I agree. The thing is, is that taxes often become a stressor for folks because they don’t plan ahead. That’s the biggest thing is that you go to your mailbox, and you see a letter, and it says the IRS on the top, and you immediately get this fear in your head. It’s because you think, “Oh, what did I do wrong? Or what should I have done otherwise,” or something like that. 

I mean, it really just comes down to if you are thinking about these things proactively, if you have sort of that phone a friend that you can reach out to throughout the course of the year, you’re not going to be worried when the time comes because you’ll say, “I already talked to him about that. I already know what this is going to be. Oh, this letter from the IRS is just the refund check that I’m expecting to come back from them.” It’s not going to be that fear anymore.

[00:14:02] TU: So let’s shift gears and talk about some of the tax changes that individuals should be aware of. I think one of the main advantages in working with a professional is that you as the individual don’t have to sift through all the changes that are happening and understand the implications to your own plan. You can get the CliffsNotes version of that or someone that’s looking out for you and, obviously, has an understanding of your individual situation. 

Sean, my understanding is there are some changes that folks should be aware of that impact this filing season. Then there’s also some other changes on the horizon that will impact things in the future. Tell us more.

[00:14:36] SR: Yeah. I mean, at this stage of the game, I don’t want to say it’s too late. It’s almost never too late to do really anything. But given that we’re getting into January of 2023 now, not a whole lot to talk about for 2022, but just a couple things to keep top of mind for folks, especially because it’s questions that people may have when they’re talking to their accountant about, “Hey, this looks a little different than last year.” 

So one big thing that will probably be glaring to a lot of folks is there was a $300 above the line, we call it, credit for charitable deductions that has happened for the past couple of years. So that basically, even if you’re not itemizing your deductions, if you’ve made charitable contributions, you were able to take $300 of that as a credit, that is sort of a no more going forward. So in order to take those charitable contributions, you’re going to have to itemize your deductions. 

Again, I just want to point that one out because I know a lot of people, it was right there on the front of the – On the form. So a lot of people will probably think, “Hey, what happened to that?” But that also brings up a good point that you always want to – Another reason why working with a tax professional stay on top of these things is really helpful because different states, different jurisdictions all have different rules when it comes to these things. I know I was just talking about charitable contributions, for example. In the state of Arizona, that’s actually something where you’re able to make donations up until the filing date. Sort of like you can traditionally with IRA accounts when you think of on the federal side of things. 

That’s another reason why I say even though it might seem like it’s too late, it’s not always too late, and you really want to keep in mind that different states and different jurisdictions have different kind of rules with that. 

[00:16:05] TU: Which is why, Sean, you love the Ohio jurisdiction and the [inaudible 00:16:09], right? Isn’t that your favorite? 

[00:16:11] SR: Yeah. Love would be one word that I could use to describe it. I would definitely say that that’s one of them. It keeps me on top of my game. I could say that too. I’m running out of nice things to say. But, yep, sure, we’ll go with that. 

Sticking on the subject of sort of top of mind 2022, things to keep in mind, one of them – This is not so much of a, hey, it’s something that you can still do now, just something that you’re going to want to really be careful of, especially when you’re talking to your accountant and probably trying to argue. Hey, how come I’m not getting the credit for this or something? You alluded to the Inflation Reduction Act. So that was the act that President Biden signed back in August. So a lot of changes to a lot of things, specifically, energy credits, things of that nature. A good number of changes to keep an eye on there. 

A big one is the Residential Clean Energy Credit. So that is traditionally – Forgive me, I can’t think of the old name. They keep changing the names of these things. But keep in mind solar, geothermal, that type of thing, really the renewable energy sources. So that was supposed to drop down to a 26% credit in 2022. That bumped back up to 30% in 2022, and that’s going to go all the way out through 2032. So that’s a good one to keep in mind. 

Electric cars, that’s another one, very important. So as of – The date on this one is August 16th. So if you bought a car before August 16th of last year, electric car, sort of the old rules, I won’t get into those. You’re probably familiar with them. If you bought a car beginning August 16th and through the end of last year, an electric car, there’s a final assembly requirement where your vehicle must have been assembled in North America. Those rules apply as of August 16th of last year, so something definitely to keep in mind there. 

Then going forward into 2023, if you purchase a car in this year going forward, there’s not only final assembly rules, but there’s mineral sourcing rules. There’s sort of battery component rules. So a lot stricter requirements there. We can link to – The Department of Energy has a good list where you can kind of put in your VIN and see if your vehicle qualifies and what it is. But the long story short there is it’s $7,500 credit going forward. But again, you want to keep those dates in mind whenever you purchase the vehicle. So it’s kind of one of those things to keep in mind now. 

That’s a good segue into 2023. So again, closing the door in 2022, a lot of good things heading into 2023, specifically around those energy credits. We talked about new – Or electric vehicles. We talked about new electric vehicles. But starting this year might bring a lot of people into the used market here, so used electric vehicles. That will be a new credit, 30% up to 4k of those. So that’s something definitely to look forward to. 

Energy credits, again, not so much on the solar geothermal side, but more on the, hey, I got new doors, new windows, the typical sort of regular household improvements. You’re probably familiar with those being a $500 lifetime credit. That starting this year going forward is actually going to be a $1,200 annual credit, so that is quite the jump there. Definitely some new restrictions and everything to keep an eye on. Obviously, you want to talk to an accountant about all that kind of stuff. But that’s a very big jump from $500 a lifetime to $1,200 a year. So definitely want to take advantage of that going forward.

[00:19:34] TU: Is that one that if I invest, I don’t know, $10,000 in new windows, that you can disperse that credit over several years? Or is it within the year of purchase for 1,200, right? Because a lot of those examples you gave, windows, doors, roofs, etc. are, obviously, going to be fairly significant expenses.

[00:19:54] SR: Yeah. It’s in the year that you actually dole out the cash that you get the credit back. In a lot of cases, these credits are nonrefundable. So what that means is that if you, at the end of the day, don’t owe anything or don’t have any taxes to offset, you don’t get that credit back for you. So refundable credit basically means, hey, if I actually offset all of my taxes and still then get some, you’ll actually get that back as a refund. 

A lot of these energy credits, you just want to take a look at all of them. I won’t get into which of which. But some of those are nonrefundable, meaning they’ll offset your taxes that year but not going forward.

[00:20:30] TU: Which is another great example of planning, right? 

[00:20:31] SR: Of planning. Exactly, exactly right. You beat me to it, where if you’re making a big capital purchase, you say, “All right, I’m putting in these new windows or I’m getting this solar. I’m finally getting it done,” you want to make sure you have the taxes to offset. Maybe you sell some of those investments that you’ve had for a while. Take on some of those capital gains. Use the credits to offset it or – That’s where that tax planning definitely comes into play. Absolutely. You’re taking my job, man.

[00:20:56] TU: Sorry. It was a good example. I was just thinking about all – Obviously, a large percent of our community may be doing home improvement projects, other things. This is a common one, I think, will be coming up.

[00:21:05] SR: Absolutely. Yep. But, yeah, I mean, sticking to this year, I don’t want to say it was a boring year. Every year from a tax standpoint is exciting in my mind. But the biggest thing I would say outside of the energy stuff, the name of the game has been inflation. So obviously, inflation is top of mind for a lot of folks. So a lot of inflation-related changes going into next year, and what does that mean? Mostly means limits are going up for a lot of things. 

So 401(k), deferral limits. That was up $2,000. That’ll be 2,500 this year. Catch up deposits also up 1,000, so that’ll be $7,500 this year. IRA contributions went up $500, so that’s $6,500 this year. The catch up stayed the same on that, but similarly, inflation. So starting next year, 2024, that will be indexed to inflation. That’s another one there. Tax brackets, so all the tax brackets were bumped up a bit due to inflation. I’m not going to get into the specifics of which one. Each of those, each of the limits are there. The overall story is that you basically can make more money before you bump into that next bracket. 

But the one thing I really want to hone in on there is a lot of people don’t really – I don’t want to say don’t understand the concept of tax brackets. But a lot of people think, “Oh, I don’t want to make another $1,000 because that’s going to bump me into the next bracket. Or how’s that affect me? Is that going to put me the next tax bracket? Or how’s that look with everything?” I just want to make sure a lot of folks on here understand the idea of incremental dollars being taxed at that next bracket. So what does that mean? 

If you’re right on the edge, and you make an extra $100 that bumps you into that next tax bracket, that $100 will be at the new tax rate. The rest of your cash is all getting taxed at the rates that you were before. So I don’t want anybody here who’s got two job offers on the table and saying, “I don’t want to take this higher one because it’s going to put me in the next tax bracket.” That’s not how it works. It’s only going to be a couple extra dollars. I know that’s a big scary one. So that’s where you hear about effective rates and everything. There’s a lot we can get into there, but I just don’t want to scare folks any more than they already are.

[00:23:07] TU: Sean, it reminded me as you’re talking. I’m sure many folks listening are familiar with the Schitt’s Creek episode, where David is talking about the tax-write offs and the things that he’s buying because they’re tax-write off, right? This –

[00:23:20] SR: Write-off, yeah. 

[00:23:20] TU: It’s like we need an episode on the incremental approach. I mean, you hear that all the time of like, “Oh, I don’t want to go in the next tax bracket. Or if I earn additional money, I’m going to go into that.” I think a lot of that may come from the misunderstanding of how that works in terms of the incremental approach.

[00:23:37] SR: Exactly, right. You’d never want to turn down more cash. I think we had talked about before. But even though it might not seem like the best thing, a bigger tax bill at the end of the day generally means that you actually did better that year.

[00:23:49] TU: Yeah. Well, this is great stuff, Sean, and I want to transition. One of things we’re really excited about as we head into this tax filing season is that for new clients of YFP Tax, we’re really putting a stake in the ground that we’re not doing filing only. One of the reasons we got to that decision point was everything that we’re talking about right here, which is that we really feel like tax when done well is really proactive. It’s strategic, and we’re thinking about this year round so that we can optimize that situation. Yes, filing is a part of that, of course, but we really need to be thinking more strategically. 

So that’s one of the reasons that we are really excited, Sean, to be introducing YFP’s what we’re calling CTP, comprehensive tax planning. Tell us more about what it is, who is it for, and potentially who is it not for as well. 

[00:24:39] SR: Yeah. So comprehensive tax planning is – It’s a lot of what we had talked about before, right? So the idea of really synergizing your tax strategy with the rest of your financial strategy. It’s something where you’re touching base with us throughout the course of the year, and it really depends on what your individual needs are. It’s not something where we’re saying, “Hey. Every Friday at five o’clock, we’re all getting on the call. It’s the YFP Tax happy hour. We’re all going to talk about taxes and everything.” That’s not what this is all about. It’s really for everybody to look at their own situation and say, “Hey, I’m looking for more guidance on my withholdings.” Maybe it’s something where we’re meeting a couple times a year to talk about, “Hey, I have this new side job. I think I have to make estimated payments now. Can we talk about what that looks like?”

Or maybe it’s something where I have a real estate property that I’m thinking about purchasing at the end of the year, but I don’t even want to begin to go down that path until I can talk about what are the implications here. What if I rent it out a couple days a year? What if I rent it out 100 days a year? How’s that look? Can I live there? What are the tax implications? So it’s really for folks who want to not wait until the end of the year, like I said, and say, “Hey, here’s my box of receipts. I’ll see you next April. Get my stuff done,” and who really want to be able to sleep at night when it comes to taxes and don’t want to open up their mailbox and say, “Oh, no. It’s the IRS. What could this possibly be?”

[00:26:01] TU: Sean, if I’m interested in learning more about the comprehensive tax planning or perhaps even ready to get started, where’s the best place that I should go?

[00:26:09] SR: So the best place to go would be yfptax.com. So that’s our new and improved website we launched recently. It has a lot of different resources on there. It has the blog that you mentioned before, a lot of videos that we posted throughout the course of the year with some of these updates and some of these new tax laws that we’re talking about. It really has a breakdown of all the different services that we have. 

So whether it’s the comprehensive tax planning, CTP, that we’re talking about here, or maybe you have a side gig and you’re interested in doing some bookkeeping for that. We offer bookkeeping services, all the way from, “Hey, I just have a couple of contractors I need to do payroll for,” all the way up through what we call our fractional CFO service, which is more of the, “Hey, let’s sit down. Let’s talk strategy about my business. Let’s put some forecasts and budgeting together and everything.” That website will have a great starting point to get you started. 

But from there, you can get in touch with me. I’ll answer any questions you have. We can get on the phone. If you want to look at my face, we can get a Zoom call together. Or I’m happy to talk via email, answer any questions. So you can reach me personally at [email protected]. Again, you can also go to www.ypftax.com. You’ll get links to me. You’ll get links to all the things that we’re talking about here. That’s the best place to start. 

What I would say is, definitely, if you’re interested, don’t wait. We’re getting into tax season. I know that I’m biased to say that, but I think you’re going to lose a lot of us in a couple of weeks. So might be not a bad time to hop on there and take a look.

[00:27:34] TU: Don’t wait indeed. This is really the – Now, I’m not going to say quiet. You guys got a lot of stuff going on, but really the lull before the storm that is the tax season and then, obviously, some hibernation of rest and recovery thereafter. So make sure to head on over to yfptax.com. Lots more information there. As Sean mentioned, you can reach out to him directly to set up a call, get some more information. If you’re ready to get going, you can also click on a complete a quick form. You can get started. But all the information is there on the website. 

Sean, thanks so much, and we look forward to hearing from you after tax season.

[00:28:06] SR: Thank you. Yeah. It’s definitely the calm before the storm. But like I said, it’s sort of like if you watch the weather channel before a hurricane. Even though it’s the calm, everybody’s still prepping and getting ready and everything. Then once it’s all said and done, yeah, it’ll be nice to touch base in May once everything’s kind of a little bit calmer.

[00:28:23] TU: Great stuff. Thanks, Sean. 

[00:28:24] SR: Thank you.

[END OF INTERVIEW]

[00:28:25] TU: As we conclude this week’s podcast, an important reminder that the content on this show is provided to you for informational purposes only and is not intended to provide and should not be relied on for investment or any other advice. Information in the podcast and corresponding materials should not be construed as a solicitation or offer to buy or sell any investment or related financial products. We urge listeners to consult with a financial advisor with respect to any investment. 

Furthermore, the information contained in our archived newsletters, blog posts, and podcasts is not updated and may not be accurate at the time you listen to it on the podcast. Opinions and analyses expressed herein are solely those of Your Financial Pharmacist, unless otherwise noted, and constitute judgments as of the dates published. Such information may contain forward-looking statements that are not intended to be guarantees of future events. Actual results could differ materially from those anticipated in the forward-looking statements. For more information, please visit yourfinancialpharmacist.com/disclaimer. 

Thank you, again, for your support of the Your Financial Pharmacist Podcast. Have a great rest of your week. 

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YFP 070: Pre-Planning for Tax Season


 

Pre-Planning for Tax Season

On Episode 70 of the Your Financial Pharmacist Podcast, Tim Baker, YFP Team Member and owner of Script Financial, talks with special guest Paul Eikenberg. Paul works alongside Tim at Script Financial and handles all of the tax planning and preparation for Script clients. On this episode, they discuss the new changes to the tax code and tips you can use for pre-planning for tax season.

Summary

In this episode, Tim and Paul discuss changes to the tax code that will affect your tax preparation for this year. There are several changes that have been made. The 1040 form is 23 lines and has new schedules. Standard deduction amounts are changing from $12,700 (couple) and $6,350 (individual) to $24,000 and $12,000, respectively. Personal and dependent exemptions are going away, meaning that those who have itemized before will probably take the standard deduction. Other changes include the amount that’s able to be deducted for medical expenses (now 7.5%), limits for local and state income taxes, child tax credit (now $2,000/child), student loan discharge due to death or disability is not taxable in the future, and the 529 is now available for primary and secondary education in addition to college. Paul also discusses how tax brackets have changed. There are the same number of brackets, however, the rates have been lowered. Paul suggests that most people will get a tax reduction between higher standard deductions and lower tax rates.

Tim and Paul then talk about the differences between tax planning and tax preparation. Tax planning involves long term strategy matching with your personal goals. Tax preparation is more mechanical where you plug in what happened financially from last year.

Paul offers tax review services through Script Financial. In a tax review, Paul uses your tax return from last year, current paycheck stubs, and payroll statements to project what your tax bill will be, assess if you are withholding enough from your check, and walk you through different options. Paul is still offering tax review services.

About Today’s Guest

Paul Eikenberg has been involved in starting and selling 4 businesses, has worked in the IT field as a franchisee and executive, as VP of Franchise Operation for a 500 unit Franchise System and is currently is serving as Vice Chairman of the Board of APG Federal Credit $ 1.4 billion asset Federal Credit Union. He has a wealth business operations and financial experience. In addition to being a licensed Maryland Tax Preparer, he is scheduled to completed the IRS’ Enrolled Agent exams by year end.

Mentioned on the Show

Episode Transcript

Tim Baker: What’s up, everybody? Welcome to Episode 070 of the Your Financial Pharmacist podcast. Paul, thanks for joining me on today’s episode. How’s it going?

Paul Eikenberg: It’s great, Tim. Thanks for having me.

Tim Baker: Yeah, of course. So Paul, why don’t we take a step back before we kind of get into all of the exciting things that are tax. And we don’t spend enough time on taxes, which is a very important part of the financial plan. But before we kind of do a deep dive into discussing the different changes to the tax code and what our listeners can do to prep for the upcoming tax season, why don’t you tell us a little bit about yourself and how you came to be the tax guy at Script Financial?

Paul Eikenberg: Sure, I’ve had several careers now. I’ve owned two businesses. And most recently, I was working with a network service provider. When that job got eliminated, I decided that I’d go back to tax preparing and got my Maryland certification, and I’m working on the enrolled agent program with the IRS, which I’ll be completing in December. And was looking to work real hard for part of the year and not so hard the rest of year has been my life. So that’s when you and I sat down together and started talking about our financial plans, and I wasn’t ready to retire, but I wasn’t ready to go back to work full-tilt. So you and I came to an understanding that Script Financial needed a tax practice and that it was a good fit for me at the right time.

Tim Baker: Yeah, and I think for me, you know, I think tax is so important because it really permeates every part of the financial plan. And I think a good understanding of one’s own tax situation and how you can practically plan for your tax situation I think is super important. So like I said, I’ve really enjoyed working with you and Anne over the years, and I feel like when I think back on the first time we met, I think we talked a lot about finances, but especially with Anne, we talked a lot about just life and just experiences and things that you guys have experienced and my experience, and it was more about the human element, I think, that we connected. And it’s been a good ride so far, and I’m lucky to have you as part of the team. So yeah, thanks again for coming on the podcast today. So let’s hop right in. So Paul, last year, the new administration passed the new tax code. The Tax Cuts and Jobs Act was signed by President Trump on December 15, 2017. What has that done to the tax system from where you sit as you’re looking at preparing taxes for 2018? What are some of the big changes?

Paul Eikenberg: Oh, everybody’s still working on figuring it out. The forms, the 1040’s changing. And the IRS has released drafts of the 1040s and all their forms, but they’re still in draft form. None of it’s been finalized. But one of the big changes you’ll see is that form 1040, which was 79 lines last year, is going to be 23 lines this year, postcard-sized, which sounds great until you find out there are six new schedules to support the 1040.

Tim Baker: Right.

Paul Eikenberg: And those lines really haven’t been removed, they’ve been moved to other schedules. So from a complexity of doing your taxes, it is I expect to be every bit as complex as last year. We will have a lot more people this year will be itemizing than previous because of the changes in the standard deduction.

Tim Baker: Yeah, it’s funny because I think the rhetoric behind the tax changes were that we want people to be able to basically file their taxes on the back of a napkin. And obviously, the 1040 itself is smaller, but it looks like they just moved the information to these new schedules, which I understand are actually numeric. So if people are familiar with the tax forms, you know, you have Schedule A, which was typically for your itemized deductions, Schedule C for business income. And now we actually have Schedule 1-6, so it actually makes it a little bit more confusing, in my opinion. Obviously, we haven’t seen kind of the final product of what the forms will actually look like, but interesting that I think it’s still going to be as complex as it was before. So let’s talk about some of the meat of some of the changes that we’re seeing. So you mentioned the new standard deduction. So walk us through some of the big — what is the standard deduction compared to the itemized deduction? And how has that changed for this upcoming year?

Paul Eikenberg: Well, in 2017, the standard deduction for an individual was $6,350. For couples, you were looking at $12,700. This year, it’s going to be $12,000 for single and $24,000 for couples.

Tim Baker: So essentially, it’s doubled.

Paul Eikenberg: It would seem that way except that your personal and dependent exemptions are going away, which was $4,050 per individual.

Tim Baker: So it looks like a little bit of the same stuff with kind of just rearranging the numbers, similar to the lines in the 1040.

Paul Eikenberg: It is. You’ll have, you know, you’ll have a higher standard deduction. So a lot of people who were itemizing last year will be taking the standard deduction this year. There’s estimates all over the board as to how many people will be affected. But you know, we saw a lot of them in our practice that were maybe $2,000-3,000 over the standard deduction last year that it made sense to itemize. This year, they’ll be taking the standard deduction.

Tim Baker: So just to back up, typically, what you want to do as a taxpayer is you want to look at what the standard deduction is and then what you’re itemized deduction is and then you want to take the greater one of those. So last year, if you were single, and you had itemized deductions of $6,500, you would have took that over the standard deduction of $6,350 because it was a greater number. So Paul, quickly, what are some examples of what would constitute an itemized deduction?

Paul Eikenberg: Mortgage interest is one of the big ones. Property taxes, state taxes, charitable contributions, employee business expenses, medical expenses can be if you have a significant amount of medical expenses. In the past, it had to be the amount over 10% of your adjusted gross income. This year, it’s dropped to 7.5%. But for the most part, unless you had a major health factor, you’re not — most people aren’t getting to itemize the medical insurance, I mean medical deduction.

Tim Baker: OK.

Paul Eikenberg: Last year, one of the big changes, state and local income taxes were deductible. They’re still deductible, but there’s a $10,000 limit on the amount of state taxes that can be itemized, and that is withholding taxes and property taxes. So higher income earners, that’s going to be a reduction in what you can itemize.

Tim Baker: So that’s big for high income earners and if you live in a part of the country where your mortgage and state and local taxes are higher, so say in the San Francisco area, that’s going to obviously affect those areas more than, you know, if you live in more of a rural area. How about, Paul, how about with kind of the, you know, if you have kids — how does the tax code change if you have kids?

Paul Eikenberg: Well, the biggest change there is the child tax credit goes from $1,000 per child to $2,000 per child. And the amount that’s refundable goes from $1,100 to $1,400. So that is the biggest change. The other change is that credit was phased out at $110,000 last year for a married couple. The phase-out has been raised to $400,000 this year.

Tim Baker: Which is huge, especially for our listeners, you know, probably as a couple are making more than $110,000. Now if you make up to $400,000, you get that $2,000 tax credit. And really good point of emphasis here is a credit is actually a dollar-for-dollar reduction from your tax bill, whereas a deduction just kind of decreases the income that you’re taxed on, so it’s not necessarily a dollar-for-dollar. And I think for the child tax credit, I believe if you’re single, I think it’s you can make up to $200,000 and still get that $2,000 credit per child. So just like you were talking about, it’s changed but the personal exemptions have gone away, but you’ve increased the child tax credit. So it’s a little bit of a — I don’t want to say bait and switch, but not a huge change. OK, so what about the — in terms of like education? We’re talking like the 529, the student loans and forgiveness. Are there big changes for that? Because that would obviously be something with listeners who have kids that are trying to avoid maybe the student loan hell that they’re in, so they’re saving for 529 or, you know, if you are a borrower and you’re trying to navigate your student loans, are there any big changes to the tax code in those two areas?

Paul Eikenberg: One of the big changes is the student loan discharge due to death or disability is not going to be taxable in the future.

Tim Baker: OK.

Paul Eikenberg: The interest deduction, the phase-out earnings have been raised a little bit but not significantly. I guess the biggest change is the 529 is going to be available for use for primary and secondary education.

Tim Baker: Yeah, so from what I understand, Paul, the 529, you can actually use for kind of your grade school, middle school, high school, which was a change because the 529 was really — before, it was just locked into just college. They did, for you homeschoolers out there, there was supposed to be a benefit that was stripped out at the last minute, so unfortunately, the 529 is no longer good for homeschooling. And so you know, from what I’m hearing more about people that work with clients that use 529s, it could actually — you could use it as a pass-through. So if you’re paying for private school, make sure you’re funding a 529 because you get a state deduction in most states. But then you can also use a 529 almost like you would use a retirement account where you’re accumulating, you know, so if you have a child and they’re going to go to school in 18 years, you’re investing that money and you’re accumulating it over time so you have a bucket of money for your child in the future to apply towards college. And then to circle back, the student loan interest deduction, it remained intact. I think it goes up a little bit, but not enough to really affect a regular pharmacist. Maybe for residents out there, the 2017 phaseouts were I think $65,000-80,000, so anything above $80,000, you didn’t get a deduction. So obviously for residents, for those maybe your PGY1, PGY2 year, you’d probably get a deduction for those years. But you know, beyond that, not necessarily. But the fact that the loans are discharged due to death and disability and not taxable because of death and disability is a big win for those people that unfortunately have to deal with that situation. So I guess, Paul, before we kind of talk about what we can do to prepare for the 2018 tax season, just about I guess the brackets. You know, I think everyone would like simplicity, but with the new tax code, do the tax brackets, how did they change? Did they change? What does that look like?

Paul Eikenberg: It’s pretty much the same number of brackets, but the rates are a little lower. The base rate is still 10%, but the next bracket down from 15% to 12%. The bracket above that went from 25% to 22%. 28% to 24% and then the next bracket, 33% to 32%. The others are pretty much the same or higher. So you know, we’re looking at overall, most of us are going to get a tax reduction between the higher standard deduction and the lower tax rate should have a positive effect on most of us out there.

Tim Baker: Yeah, and I think, you know, the number of brackets, again, like it would be nice to pare those down. I think essentially, though, moving forward with this tax plan, I think it is going to be better from a taxpayer perspective. Most people’s taxes are going to be lower. So that’s something to consider as you plan, you know, for the future. And that’s a good segway into kind of our next discussion is, you know, the difference between tax planning and tax preparation. So Paul, for you, how would you separate those two things?

Paul Eikenberg: The preparation is just more mechanical. We’re taking what happened last year, plugging it in, selecting maybe a couple options, whether itemizing or standard deduction works best for you, should you make an IRA contribution up to April 15 that you didn’t make before the end of the year. But you know, that’s working in the past with a lot of things you can’t change. Tax planning is really taking a long-term strategy, kind of matching your personal goals with your tax strategy. So you know, if your goal is to pay off student loans now, you may not want to defer as much retirement income as somebody without that. It’s just kind of putting all those pieces together and, you know, when we look at planning, like a mid-year plan for somebody, we’re going to look at where you are now, have you had enough taxes withheld that you won’t have a surprise come April? And are you taking advantage of the HSAs? Are you definitely getting the matches in your IRA, in your retirement programs?

Tim Baker: Sure.

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Paul Eikenberg: You know. If you have a business, rental property, are you doing everything you can? Are you planning out your expenses for those to mitigate your taxes as much as possible?

Tim Baker: Right. Yeah, and the way I look at prep versus planning, tax prep versus tax planning is the prep I think is the very reactive in nature. You’re like, ope, this is what happened for 2018. Let’s plug in the numbers and see what pops out. And sometimes, it’s a surprise, you get a refund. And sometimes, it’s where you’re writing Uncle Sam a check. And that can’t be fun.

Paul Eikenberg: I know from preparing a lot of taxes that the most painful thing is to be doing your taxes, waiting and being surprised with a big tax bill instead of a small refund you were expecting.

Tim Baker: Yeah, so maybe the approach we take is maybe self-preservation too because it’s tough to sit across the table and say, ‘Hey, you owe a lot of taxes.’ So obviously, what we’re trying to do from a tax planning perspective is get out in front of it, be proactive, and actually, you know, don’t let really the tax situation control you. You’re controlling your — whether it’s, like you said, deferring the taxes or avoiding the taxes, whatever that looks like.

Paul Eikenberg: If you’re proactive, you have a lot more options.

Tim Baker: Yes. Yeah. And for some people, you know, we talk about having funds set aside, whether it’s for home maintenance, emergency fund, a vacation fund, a lot of people don’t have a tax bill fund that they can just write a check and say, ‘Here you go, Uncle Sam. I didn’t pay you enough over the year, so here’s a sum of money.’ So that definitely could be painful. So Paul, let’s break down. You kind of talked through it a little bit, but when you sit down and you do a tax review with a client, what does that look like? How does that play out?

Paul Eikenberg: Let’s say we’re doing one for you now. You know, what I’d want to see is the most recent paycheck stubs. You know, we’d want to look at your last year tax return, and we’d really take your payroll statement and look at where you’re earning are, what type of retirement program you’re in, what other type of health insurance — are you pre-tax, HSAs — and project all the contributions through the end of the year for earnings and withholding, withholding taxes, and pre-tax contributions. From there, kind of review the tax return from last year, look for other sorts of income, deductions, project those, and then we’d sit down for a half hour conference and kind of go over the assumptions that I make projecting your situation through the end of the year, be sure that if you had capital gains last year, rental income, any of those other type of items, that we’re working on the proper assumptions.

Tim Baker: Right.

Paul Eikenberg: You know, are there estimated taxes or anything we’re missing that you’ve already paid Uncle Sam. And from there, we kind of project what we expect your tax bill to be, what your withholding’s going to be, if nothing changes, are you going to have a refund or owe money? And then we kind of walk through your options. To me, the HSAs are a great tool. Everybody should be getting their matching retirement, whether that’s pre-tax or a Roth 401k. If your employer’s matching it, that’s something you want to be sure you’re taking advantage of. And we’d kind of walk through your options of is there anything you should be doing to mitigate the taxes? Have you had too much withheld? Should you lower it? Have you had not enough withheld? Do you need to increase it? You know, are you going to be subject to penalties if nothing changes? Maybe you need to make an estimated tax payment. So there are a lot of things we look at.

Tim Baker: Yeah, and it’s great stuff. What I really like about kind of your review is that, you know, you take the pay stub — and it’s funny because when I used to work for a company, I would get paid with a paper check, I’d rip the check off, I’d deposit it, and I’d throw the pay stub on a pile. And I’d never really look at it. But actually, there’s a lot of good information, a lot of good nuggets on the pay stub about what you’re actually paying into. And it could be your retirement fund or long-term disability or whatever that is. And what I really like about your system is, you know, you use that information to kind of set up where we’ve been throughout the year and then extrapolate that forward to where we expect you to be. And what I like is is that you generally say, ‘Hey, if nothing changes, you’re going to owe $2,000. Or you’re going to get back $2,000.’ You’re going to be basically equal. You won’t owe or get anything back.’ And then if there is an imbalance, then we kind of discuss some of the levers that we can pull. So you know, you mentioned the HSA, increasing a contribution into your 401k, whatever those things are. And I think another one that probably we could talk about is just, you know, changes to your payroll withholding, the W4 form. A lot of people, when you begin a new job, you fill out the W4, and you don’t really look at it. But that W4 form basically dictates to your employer how much tax should be withheld from your paycheck. And then if you owe more taxes than what is withheld, then that’s when you actually have to write a check to Uncle Sam. So it’s kind of important to really understand that form itself and what that does. And sometimes just changing that is one of the levers that we pull. So instead of paying at the end of the year, you just pay a little bit more throughout the course of the year. So these are I think levers that I think are important to look at and go through and be able to, again, be more proactive in your tax situation than just say, ‘Well, this is what happened last year. Cross my fingers, hopefully I don’t get any surprises,’ and go from there. So Paul, are you still doing the reviews for this year? I know we’re into October. What does that look like?

Paul Eikenberg: Yeah, we’ll probably continue doing them until the Thanksgiving holiday is the plan right now.

Tim Baker: OK. So I think, you know, for listeners out there, if you’re interested, some people, you know, really enjoy to do a great job of analyzing your own tax situation. But if you’re not one of them, and you can think of a million other things to do to spend your time, you know, we can definitely help. Paul can definitely help. I think he does a great job with my clients. So you know, if you’re interested, sign up for the Script Financial tax review, and it basically includes a lot of the things we talked about, you know, analyzing your current pay stubs, you know, doing an income projection, you know, for the rest of the year, reviewing last year’s returns to see if there’s any discrepancy. So you know, if there’s big changes like you got married, you bought a house, you had a baby, those are going to affect, you know, obviously your tax situation. And at the end of the review, really to project out kind of your year-end tax status. And with that, basically Paul delivers that in a 30-minute video conference where, again, you review all the assumptions and projections and kind of go over the steps that you need to take to kind of, you know, pull the levers and say, ‘If we want to get money, this is what we would do. If we want to not owe the government money, this is what you should do.’ And I think it’s of great value. So normally, a tax review like this, it would be priced at $99. Between now and Nov. 20, so this episode will be released on Oct. 18, so about a month, we’re running basically a promo for 20% off. So that just brings it down to $79. So if you go to YourFinancialPharmacist.com/tax and use the coupon code YFP, you’ll get that 20% off the $100 price. So it’s YourFinancialPharmacist.com/tax to get that — to sign up for the review and use the coupon code YFP for the discount. So Paul, you know, good stuff today. We kind of talked about changes to the 2018 upcoming tax year, changes to the 1040, it looks like we’ve added some numeric schedules, the standard deduction has increased, and we talked about some of the changes with, you know, with the new tax code with deductions and credits, and then really what you can do for your own tax situation to kind of get in front of the ball and make sure that you have really no surprises for, you know, this upcoming tax season. So Paul, anything else to add before we kind of sign off here for the day?

Paul Eikenberg: Yeah, one more thing to think about that we think we’re going to see a trend with this year with the standard deduction going up. In the past, people have tried to pay their property taxes on December 31, made charitable donations so that they got those in in time to be deductible in the current year. I think the trend’s going to be that a lot of the people will be doubling up on those. They’ll be looking at their tax situation and instead of making donations in 2018, they may make twice as many in 2019. And think about your property taxes as to whether it makes sense — like in Maryland, you’d pay your property taxes from July to July and you have an option of breaking it up. So it may make sense to pay more in one year and then take the standard — alternate your itemized deduction one year to the standard deduction the next year. So that is one of the things we anticipate being a good strategy for quite a few people out there.

Tim Baker: Yeah, and I think just a tip in kind of the direction of doing some proper planning and being as efficient with your tax situation as you can. Like I said, if the listeners are interested in working with Paul and doing a tax review, it’s YourFinancialPharmacist.com/tax and use the coupon code YFP for the 20% discount. So Paul, good stuff today. Thanks for coming on the podcast, really appreciate it. And to the listeners, thanks again for listening. And we’ll catch you next time.

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