Perceived Reality

The $10,000 Mistake You’re Probably Making Every Tax Season

5 min
Jul 22, 20259 months ago
Listen to Episode
Summary

Tax professional George Dima discusses common tax planning mistakes business owners make, emphasizing the importance of proactive year-round tax strategy rather than last-minute DIY approaches. He highlights how incorrect business structure selection costs clients thousands to tens of thousands annually and advocates for early professional consultation to avoid surprise tax bills.

Insights
  • DIY tax software during tax season often results in unexpected large tax bills because taxpayers lack year-round strategic planning and miss optimization opportunities
  • Business structure selection is a critical lever—over 100 clients were in wrong structures, overpaying $1,000s to $10,000s annually on average
  • Tax professionals are unavailable during peak season (Feb-Apr), making 6-9 months advance planning essential for meaningful strategy development
  • Capital gains timing strategy and stock option planning require detailed analysis that DIY tools cannot replicate, especially for detail-oriented professionals
  • Proactive communication with accountants throughout the year prevents question accumulation and enables real-time guidance on major life/business events
Trends
Growing reliance on DIY tax software creating false confidence and downstream compliance/optimization gapsIncreased complexity in tax planning due to cryptocurrency, equity compensation, and capital gains requiring professional guidanceBusiness owners underestimating impact of business structure choice on tax liability and long-term wealthShift toward year-round tax advisory relationships rather than seasonal tax preparation engagementsAnticipated tax law changes creating demand surge for professional tax guidance and strategy consultationExpectation for accountants to provide always-on accessibility (evenings, weekends, holidays) to serve busy professionals
Topics
Business structure optimization (LLC, S-Corp, C-Corp, sole proprietorship selection)Capital gains tax strategy and holding period planningStock option exercise and equity compensation tax planningDIY tax software limitations and risksYear-round tax planning vs. seasonal tax preparationCryptocurrency and investment tax implicationsTax planning for major life events (marriage, home sale, child birth)Alternative minimum tax (AMT) reduction strategiesProactive tax advisory relationshipsTax law changes and legislative updates
Companies
TurboTax
DIY tax software mentioned as example of tools taxpayers use that result in unexpected tax bills
H&R Block
DIY tax software mentioned alongside TurboTax as common self-service tax preparation tool
People
George Dima
Tax professional and business owner providing expert guidance on tax strategy, business structure optimization, and y...
Quotes
"My clients are always looking to legally save taxes and the kind of clients I have want to follow the rules, they want to follow the law and they are looking for an advisor that's going to help them, but together a strategy that long term is going to ensure that they do not overpay."
George Dima
"Make sure to start planning with a professional far ahead of time, maybe six months before or nine months before."
George Dima
"One of the main things that I see, and we had over a hundred clients this last tax season, that were in the wrong business structure and on average, they overpaid anywhere between a few thousand to even tens of thousands of dollars in tax just because they did not have the right business structure for themselves."
George Dima
"Make sure to get into each one of the stocks that you're about to sell and make sure that you are using the proper capital gains strategy because the amount of time that you held onto the stock is really going to influence how much tax you pay."
George Dima
"Don't wait until the questions pile up. Get all your questions answered right away and make sure you have an account that knows you that you can pick up the phone or text them or call them or schedule an appointment over email."
George Dima
Full Transcript
If you find an extension and it's the text season for you, well in fact, text season really never ends. There are a lot of changes in the wings and that's why also we have the perfect expert here for that matter. Welcome to the show George Dima. Thank you. So George, a lot might change, but already as it is, it's complex and complicated enough with the text system. What are your clients concerned about? My clients are always looking to legally save taxes and the kind of clients I have want to follow the rules, they want to follow the law and they are looking for an advisor that's going to help them, but together a strategy that long term is going to ensure that they do not overpay. Hmm, but that's what's happening. I mean, it seems like a lot of people think, oh, I'm just doing it myself, they're smart apps right now. I'm going to save $2,000, $3,000. Is that something a due encounter? And then to later find out that they have to pay so much more on taxes or did over the years. Yeah, you know, that's a really good point. And we talked about this a little bit earlier in our conversation before the show, but we get this all the time where it's tax season, it's February, it's March, it's April and taxpayers approaches after doing their taxes and turbo tax or an HR block or a do it yourself app and they have a huge tax bill and they don't know why they have it. They don't know even how it came about. I mean, sometimes don't have the money for it and I always tell them make sure to start planning with a professional far ahead of time, maybe six months before or nine months before. Wow, that is really. Yeah, the people would think, okay, it's February, it's tax season, now I can get cracking, but you would say bad idea, like definitely six months. Well, we're going in tax professionals, we're going to be too busy in February or March. We're going to be filing people's taxes. So if you want to start planning, you want to meet your advisor far ahead of time, especially if you know something biggest happening that year, you just sold a home and you know you have capital gains, you just got married and you don't know what your taxes are going to look like with your spouse. You just had a child and you don't know how that's going to impact your taxes. You just made a big purchase, we made a big sale in cryptocurrency or equity of stock bonds. You don't know how that will affect your taxes plan early because if you don't, there might be a surprise. Any tips that you can share, for example, for people who are trying to make some good investments and get some good write-off any moves that you typically advise. So if we're going to talk about strategy and I'm going to say overall, if you're a business owner, make sure to meet with your accountant and discuss your business structure because one of the main things that I see, and we had over a hundred clients this last tax season, that were in the wrong business structure and on average, they overpaid anywhere between a few thousand to even tens of thousands of dollars in tax just because they did not have the right business structure for themselves. So make sure, review ahead of time with the tax attorney or CPA. What is your business structure? What's going to be the one that's most optimal for the type of income that you earn, the state that you're located in, and how much you earn? Is there a special approach that your company has to help busy professionals, the specific system, how you go about it? I would assume that most people just want to hand it over to you and then I want to just be in good hands. But they're also those business owners who would like to maybe understand all the detail. Right. You know, it's something interesting. We talked about it before. People that are in finance or engineering, a lot of times they're very detail oriented and we have many clients that are in those fields. They want to get into the detail and what I say, make sure, get into each one of the stocks that you're about to sell and make sure that you are using the proper capital gains strategy because the amount of time that you held onto the stock is really going to influence how much tax you pay. And especially if you're earning equity from your employer and you have stock options, you exercise also, make sure to plan how much I'll turn the minimum tax you're paying because there's ways to reduce that strategically. What do you expect now for the months to come with the new tax laws that are in the wing? I'm very excited because, you know, for me, as a business owner in the tax industry, we always get a lot of business when there are tax changes and if there are any tax changes, we're going to get a lot of questions and if there aren't, let's say the bill doesn't pass, we're still going to get many questions. So very excited for the clients. I tell the clients to reach out. Any questions that you have to make sure to reach out is, as soon as you have the question, don't wait until the questions pile up. Get all your questions answered right away and make sure you have an account that knows you that you can pick up the phone or text them or call them or schedule an appointment over email if they can jump in and provide you custom guidance that knows you well. Do you also take calls from your clients after five o'clock on the weekend? That's a great question actually and, you know, if you ask my wife, she'll be very upset to say that I do take calls from clients all day, all night on weekends, holidays, trips, vacations. I'm always on the phone with clients and I'm always on the phone with staff making sure that they are serving their clients properly too, which are working for me. No wonder you're on higher ring boat. It seems like it's clients on good hands with you. Thank you. Thank you so much, George. I hope you'll see us again with the matter after third of this year's reality. Join us again next.