In short
How ultra-high-net-worth people reduce taxes by avoiding taxable events on stock gains, sometimes borrowing against appreciated assets, and using asset-specific strategies; plus common tax mistakes for individuals and business owners (not maximizing employer retirement plans, missing deductions, overpaying out of fear, and failing to self-audit bookkeeping).
Notable examples
Elon Musk selling about $10B of stock after criticism; “G-Wagon deduction” luxury vehicle write-offs that get flagged; real estate cost segregation to front-load depreciation; 401(k) borrowing; defined benefit pensions; SEP IRA/solo 401k contributions; 83(b) elections; Roth funding and later tax-free sale (as described).
Guest
George Dimov, CPA and President of Dimov Tax; built a nationwide, 50-state-licensed CPA firm after the 2008 crash; 20 years inside the tax code.
Key claims
Billionaires’ net worth is tied to stocks, so appreciation isn’t taxed until sale; borrowing can defer taxes; IRS audits often flag “silly” mismatches with industry norms; smart people miss employer deductions and overpay due to audit anxiety.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOUnderstanding Wealth and Taxation
0:24 to 1:52
Explore how ultra wealthy individuals manage to avoid taxes through stock valuation.
“People that tend to overthink or be very nervous tend to overfed.”
Borrowing Against Wealth
1:52 to 4:28
Discover strategies for borrowing against stock without incurring taxes.
“OK, there are some ways around that and there are some different types of structures that could be implemented for those people.”
Real Estate and Tax Reduction
4:28 to 5:56
Learn how real estate investments can be structured to minimize tax obligations.
“And now, of course, you have to find the lender that will allow that, et cetera, et cetera.”
Common Mistakes in Tax Strategies
7:05 to 7:41
Identify common tax deductions missed by smart individuals and business owners.
“And even the deduction itself is the single biggest thing that we see employees simply not max out.”
Retirement Plans for Business Owners
7:41 to 8:59
Explore retirement plan options that can significantly reduce taxable income.
“can you give me two or three things that you think are some of the biggest ones for business owners that they're missing?”
Self-Auditing Financial Health
8:59 to 10:00
Understand the importance of self-auditing in identifying unnecessary expenses.
“Every few months, I just review my bookkeeping.”
Navigating the Gig Economy and Tax Fears
10:00 to 14:00
Discuss the unique tax challenges freelancers and gig workers face in today's economy.
“Common places you see it is obviously HOAs and condo associations, somebody on the board, you know, maybe cutting invoices to a related party for work that needs to be done in the neighborhood.”
Navigating Tax Strategies for Businesses
14:00 to 15:11
Learn about effective tax planning and considerations for new businesses.
“So essentially, as long as you're not doing anything like that, you're fine.”
The Challenges of the Accounting Industry
15:11 to 19:18
Explore the current state of the accounting industry and workforce shortages.
“Really, when you started saying this one person business, it reminded me of the founder of OpenAI or the CEO of OpenAI said that we're going to soon have a one person billion dollar company.”
Wealth Transfer and Tax Implications
19:18 to 21:00
Understand the tax implications of wealth transfer among baby boomers.
“So there's just a massive shortage of accounts.”
Show all 15 chapters
Success Through Flexibility in Business
21:00 to 24:48
Discover how flexibility can be key to scaling and sustaining a business.
“But the kind of the larger scope of your question is if somebody truly is a very high net worth individual, they need to start planning now.”
Embracing Technology and Customer Experience
24:48 to 27:37
Learn how technology impacts customer service and professional fields.
“Many companies treat clients as a disposable unit rather than as an individual.”
Building a Supportive Entrepreneurial Network
27:37 to 28:00
Find out how to connect with other entrepreneurs for support and growth.
“And it's almost as if we own the same company.”
Building Entrepreneurial Connections
28:00 to 29:07
Learn the importance of networking for entrepreneurs and the right types of networks to join.
“If we do an amazing job on somebody's business setup, we'll become their accountant.”
Key Takeaways and Conclusion
29:07 to 29:37
Reflect on the insights gained from the discussion and the value of expert advice.
Transcript
Automatic transcript. May contain errors.0:00That's really how the ultra high net worth really don't pay taxes because the value of their net worth is tied to the stock. Someone's going to borrow against it effectively never actually pay tax. George Dimov built a nationwide CPA firm out of the 2008 crash, licensed in all 50 states, 20 years inside the tax code. And he's about to show you the playbook. What do you think is the single most expensive mistake that smart people make around taxes? People that tend to overthink or be very nervous tend to overfed. The IRS has a profile on every industry. Somebody that owns real estate can effectively pay very little to no tax depending on how they...
0:51There's something that I've always wanted to know about. And this is how do the ultra wealthy pay less taxes? What do rich people know that the rest of the people don't know? That's a great question. And it's something that gets, first of all, thank you for asking that. It's something that actually gets discussed quite a bit by politicians. And there's always these laws being kicked around exactly on this topic. How do rich people continue to increase their wealth without actually paying tax? and one of the main ways is and we're talking about people that are ultra high net worth i'm not talking about people making a few hundred thousand or even a few million or even a few tens of million those are called the working rich people that are working they may own a string of medical offices they may own a string of dentistry offices they may own a business that's generating income those are working rich okay those are people that are earning a lot of money and many of them do get taxed quite a bit.
1:54OK, there are some ways around that and there are some different types of structures that could be implemented for those people. But if we're talking about people that are billionaires, most of the time their income, pardon me, their net worth is tied to their stocks. OK, so what happens in situations like this is the reason why they're becoming richer and richer is because the underlying net worth that they have is tied to a security, a stock that they own. For instance, let's say somebody is the founder or co-founder of a large technology company. That stock may have gone from a par value of under one cent to worth hundreds of dollars.
2:36And now all of a sudden they own millions of the stock and they're billionaires. And what happened during this time, the stock appreciated the value, but no actual taxable transaction occurred. In other words, they're only taxed when they sell the stock. And there was an example of this, Elon Musk, a few years ago, there was one of these people from Congress that criticized Elon Musk for not paying tax. And he said, OK, I'll pay some tax. And he sold something like$10 billion worth of stock. Or I think his actual tax obligation was$10 billion. So he sold a lot more than that. I don't remember what the exact figure was.
3:12He said, okay, I don't pay enough tax. Here's 10 billion. And I bet you're going to misspend this 10 billion anyway. So he kind of made a joke out of it, but he actually did it. Right? So that's really how the ultra high net worth really don't pay taxes because the value of their net worth is tied to the stock. Now, if they actually want to use it, they have to sell it and they can pay some tax or some of them borrow against it effectively never actually paying tax, which is another strategy. Tell me about that. Well, there's this theory that if you have your net worth tied into this, this actually is a rich person strategy that anybody can take advantage of to some extent or another.
3:49Many 401k programs may allow you to borrow from them. So let's say that you've been contributing to your 401k for a 20 or 30 year career and you have called a few million dollars in there. OK, depending on how it was invested and how that performed. There are some 401k programs that I've seen in the past allow you to borrow against that. So what happens is you take out a loan. Of course, you have to pay interest. But since it's a loan, you've never actually cashed out of this money. You've never actually distributed this money. So you're not paying taxes on this money. And this is a kind of a not necessarily a loophole, but a strategy that some people use that have quite a bit of net worth tied to a particular security.
4:27They borrow against it. And now, of course, you have to find the lender that will allow that, et cetera, et cetera. But it is something that theoretically can be done that we've seen in some cases. What do you think is the single most expensive mistake that smart people make around taxes? So there's a it really this question really depends on what asset and income bracket people fall into. And when I say bracket, I don't necessarily mean how much they make or how much they own. It really matters on how they earn their income and also how they have their income invested or how they have their assets invested.
5:02So, for example, somebody that owns real estate can effectively pay very little to no tax depending on how they structure the real estate and depending on what they do in terms of tax strategy with it. For instance, cost segregation studies are a way that people can front load depreciation and take a deduction against other forms of income if done correctly, which could reduce or completely eliminate their tax bill. So that's somebody that's real estate heavy can actually eliminate in the short term their tax bill using cost segregation studies and using real estate as a strategy. Now, somebody that doesn't have real estate at all.
5:41OK, that might be a W-2 employee. The single most common thing that I see people miss are simply the things that are offered by their employer. You'd be surprised. Many people just simply don't take advantage of these things. And one of them is your 401k mash. this is something that people ask but finally pushed me to start my own thing honestly i just stopped waiting to feel ready because you never do you just start and when you're starting you don't want to get buried in technical stuff before your first sale that's where shopify came in for me everything i needed was there from day one here's what i wish someone had told me you don't have to know how to do it all yourself when we are gearing up for a product launch shopify is what made it actually happen.
6:25And when I'm traveling for the show, the business keeps running because the platform handles it. Two things I lean on, Sidekick, their AI, which helps me when I'd otherwise be stuck, and ShopPay, the easiest checkout I've used. Your customers feel the difference. If a friend asked me, I'd say stop overthinking it and launch. You can be up and selling in a few simple steps. If you're ready to hear of your first sale today, head over to shopify.com slash founder story to start your free child today. That's right. Start your free child today at shopify.com slash founders story. That's shopify.com slash founders story is offered by many employers.
7:06And even the deduction itself is the single biggest thing that we see employees simply not max out. And this is, you know, tens of thousands of dollars worth of a tax reduction. And so this is this is the single biggest thing that we see just kind of normal, smart people because your question was what do we see smart people miss out on? That's the most normal thing that we see smart people miss out on. Now, if there are business owners, there's a whole array of different things they can do. And that's a whole, we can do a whole podcast episode just on that. If everyone's a business owner, I'd just say contact us.
7:37We'll send you a list of the top 12 things because there are many. Since this show is really an entrepreneurship show, can you give me two or three things that you think are some of the biggest ones for business owners that they're missing? For people that are older, they should explore getting a defined benefit pension plan. Those can lead to a few hundred thousand dollars worth of taxable income reduction if they're done right. And it ends up being still your money. It just goes into a retirement plan. Same thing goes for people that are at any age, but especially, well, at most ages, especially if they're younger, they can contribute over$70 ,000 to their SEP IRA or solo 401k.
8:15That's if they have a business, if they're an entrepreneur. I highly suggest doing that. Many of these things, by the way, you don't need to hire anybody to set up there. You can set it up on, you know, any online brokerage platform often allows this, which is called a SEP IRA, SEP, S is in Sam, E is in Edward, P is in plan. I think it's a simplified employment plan or something is what it stands for. I don't recall, but this is something that you could set up yourself. A solo 401k takes a little bit longer and many of the brokerages charge some underlying fees to administer it, but that's also something that you can set up by yourself.
8:52We can ask your broker to do it for you if you have a stock broker. So these are two things that I'd say major. Another thing is it's crazy. And I'll speak for myself. Every few months, I just review my bookkeeping. I find thousands of dollars of just pure waste in there. Subscriptions that I didn't know I had, services that I didn't know that I'm still paying for, contractors that I didn't know I'm still paying for that are doing a lousy job or not working at all. We've, we see companies all the time where they have employees. They didn't even know we're still in their payroll. Okay. So I'd say another major thing, if you're a business owner, just simply self audit your own bookkeeping or have a trusted person.
9:38Now it is an extension of that. This is a very crazy, you know, I've attended lectures by Vern Harnish, who does these scaling up, you know, kind of seminars. And one thing he always says that we've also seen is that every year somebody approaches him that says, hey, my most trusted right hand person has actually been stealing from me for the last 25 years. And it's around 20 million total. And we're going out of business. And he says he sees it every year. And we see this all the time. Common places you see it is obviously HOAs and condo associations, somebody on the board, you know, maybe cutting invoices to a related party for work that needs to be done in the neighborhood.
10:15So we see that a lot, but we see it in small businesses and medium sized businesses as well. Vern's awesome, by the way, I always love Vern. I think in the future, we're going to see a big rise in freelancers, people that they don't want to work a 40 hour a week job, they want to be able to freelance and bounce from place to place. You say though, that they are overpaying out of fear. Why is that? so gig the gig economy has been front and center in the news probably since covet i think in 2020 is when it became kind of a news headline thing so this is this has been a reality for a while now people not really working a traditional job but maybe having um maybe having more than one gig OK, so this is something that we've been seeing for a long time.
11:06And I'd say. The smart people are the ones that are acting out of fear, and I'll qualify the statement. People that tend to overthink or be very nervous tend to overpay. And I even remember an in-person client or more than one that came in. And we had one that was an attorney came in and he made a few hundred thousand dollars. And I said, what was your deductions? He said nothing. And I said, well, don't you want to use business use of home? Or how much do you pay for your computer? Or how much do you pay for your Internet? How much do you pay for your vehicle when you're going to meet a client or an offsite place that's not your regular commute to your regular office?
11:53If you even have one, how much is how much you spend? in courses or things to continue to stay on top of your profession. Last week, I'm standing at the open fridge at 1245 late for a call, staring at a takeout I didn't trust anymore. And I realized I'd been thinking about lunch since 10 a.m., not eating it, just thinking about it. Where's it from? Is it worth the money? Do I have time? Every day that loop running in the background. I was easily dropping$100 a day on lunch I didn't even care about. That's when I made the swap to Huel. And this matters. It's not a shake on top of food. It's a complete meal instead of food.
12:30The black edition powder is 40 grams of protein, mixes with water or milk in about 30 seconds and it starts at less than$3 a meal, 27 essential vitamins and minerals, no artificial sweeteners, colors or flavors, keeps me full for hours. On the days I'm running out the door, there's the RTD bottle, the grab and go version, 30 grams of protein, 7 grams of fiber under$5 a meal. If you want to make healthy eating simple, that's H-U-E-L. Get Huel today with my exclusive offer at 15 % off online with my code founder at Huel.com slash founder. New customers only. Thank you to Huel for partnering and supporting the show.
13:09All these are things that smart people tend to miss because they're nervous that they're going to get audited or they're not going to find the appropriate backup. But what you have to remember is the IRS has a profile on every industry. In other words, they have decades of information on thousands or even millions of submitted tax returns, and they know each industry. What your typical expense line items are is a percentage of your P &L. So that's how people actually get audited is when they do really silly things like the common example that was all over social media a few years ago was this G-Wagon deduction that somebody invented.
13:45OK, that said that what ended up happening is people earning only a couple hundred thousand dollars a year would buy a very expensive luxury vehicle and write off the whole thing in their returns. And so the IRS would see that huge, you know, hundred thousand dollar write off and immediately that return would get flagged. So essentially, as long as you're not doing anything like that, you're fine. And this is something that you spot check. First of all, the common sense and common sense isn't so common. So first, you have to use common sense, but that might not apply to everybody. Some people just genuinely might not know, which is also OK.
14:19You got to be careful when you go on social media, right? You got to be careful who you listen to. Is there a benefit for, let's say, leasing a car, renting a house versus buying a house or buying a car? You just have to chop the numbers through the tax return to see which one plays out best. These questions are best answered when you have when when you book some time with your accounting professional and actually run the analysis. Now we have ChatGPT, you can ask them. Of course, half the time it's wrong, but it's something that you can run through ChatGPT, but then you can also book maybe an hour or two of an accountant's time to run some scenarios with your data in there.
14:57And clients have us view this all the time. I've read that there's more people starting businesses now than ever. There's all these one-person businesses. If somebody starts their business today, what is one thing that they should do to start to set themselves up for success? So that's a great question. Really, when you started saying this one person business, it reminded me of the founder of OpenAI or the CEO of OpenAI said that we're going to soon have a one person billion dollar company. I don't know if you saw that it was in the news. And I think maybe it might have already happened or will happen where somebody has literally themselves one employee and they have a billion dollar valued company.
15:36so um so that just reminded me of that um but to answer your question the most businesses i'd say you have to start off and make sure that you have the right structure i can tell you some things that i've seen done before and these are can be questionable depending on how they're structured but i've seen people start a company and put their entire investment in a roth which is not taxable regardless of how much it grows. And then five years later, when they sell their share and it's worth$25 million, all of a sudden they have a Roth 1099 distribution that says$25 million, taxable portion zero.
16:16So I've seen things like that. So that could be questioned by the IRS, but I've seen other things such as using an 83B election, meaning that they are receiving all of the shares at the par value at the time that it was granted. In other words, virtually nothing. Okay, so then later when they do sell the shares, it's all capital gains. So they're only paying 20 % rather than their full taxable income, which could be as high as, you know, in the 40s. So we see things like that. Let's go back to your story. You started in 2008, which could be the worst year to start an agency or a firm. Well, you'd be surprised.
16:58I mean, quality work is always in demand and having somebody that is available is always in the med. The biggest complaint that we hear in accounting and the biggest reason people approach us or even change accountants, period, is a lack of responsiveness. And this applies to anything. How hard is it to find somebody that you truly trust to work in your vehicle? How hard is it to find somebody that is truly the best dentist? How hard is it to find somebody that's the best therapist, that's the best fit for somebody if if they are using mental health services. So this kind of just all feeds into this idea that regardless of what the economy is doing, certain services need to get done, and accounting is one of them, and there are just very few people that may actually want to do that service.
17:45I mean, think about from anybody that you might know personally, how many people say, I want to fill out government tax forms for a living. Nobody actually says that. So it's a very difficult thing to find regardless of the economy. You said before about there's a lot of CPAs retiring, so they're either going to sell their business or close. There's also a lot of people going into being a CPA. What's going to happen to the industry? That's a great question. And this is something we talked about before the call. And it's something I actually even am interested to hear a little bit from you is how is an other end of it?
18:21Because I'm seeing what's happening with baby boomers leaving accounting right now. There's nobody to replace them because the last few generations have pursued passion careers, things that they like and things they're passionate about, rather than things that are necessity careers. And one of them is accounting. Right now, you just don't have people that want to do accounting. We've had people that work at my company that have a CPA license that on good terms resign because they want to start a completely different career, whether it's in the medical services, veterinary services, mental health services, just something completely unrelated to accounting.
19:00So we see people just leaving the industry. Matter of fact, there was an article that came out right during the COVID years that said that right around that time, people rethought what they want to do with their life and 300 ,000 people, which is 17 % of the accounting workforce left the industry. So there's just a massive shortage of accounts. But what have you seen with other interviews that for baby boomers leaving? What trends have you seen? We had an executive on that was telling us around they have thousands of financial advisors and the advisors are working on people that are baby boomer age to get them to be able to set up trusts around the estimated$80 to$100 trillion wealth transfer that's happening between now and the next 10 years as baby boomers pass away.
19:52So what I want to know is what happens to that wealth from a tax perspective? I think that I'm kind of, you know, this is kind of a little bit my opinion. I really do think that it's unfair that the government taxes somebody their whole life. And then afterwards, when they've passed away, somehow this money that was already taxed gets taxed yet again. I just think that that's really unfair. And I've seen even posts on social media that break down how we get taxed so many times over. For instance, our income gets taxed when we receive it, but then we get taxed again when we actually have to buy something.
20:25So this is money that essentially got double taxed. So people have done this analysis where we're being taxed on our home that we own, that we purchased with money that was already taxed. And we're also taxed on income that we earned, but then also taxed on products that we're buying with that income. And now you have this other that everything that you've ever earned ends up getting taxed again. Now, of course, there's thresholds in each state has different ones, which are estate thresholds on how much you get taxed, if any, depending on how much assets, how much value and assets is being transferred.
21:00But the kind of the larger scope of your question is if somebody truly is a very high net worth individual, they need to start planning now. Okay, so, and we have an attorney on the team that's an estate and trust attorney on my team here at my company that puts together these type of plans. So 2008, you start, the world's basically crumbling, all this stuff is happening. What did you find that helped you, maybe the secret sauce to scaling and growing your business? I'd say being flexible on everything, being flexible on the type of work I'm taking on, being flexible on the type of client. For years, I really stayed small.
21:43I really stayed kind of just a one person type of situation. But I'd say when I started to gain more and more clients, it was when I really focused on tax specifically and personal tax specifically. And that's just because people need personal tax. And it's extremely challenging, extremely difficult. and larger companies don't want to touch personal taxes. You can't charge much for them. A client will get shocked at a$700 invoice. Well, an attorney charges a$5 ,000,$10 ,000,$15 ,000 retainer just to get started in a case. And with us, our pricing expectation from society is extremely, extremely low for a professional service.
22:28When you think about hiring a professional service, Think about hiring an architect, that's$5 ,000,$10 ,000,$20 ,000. Think about hiring an attorney, that's$5 ,000,$10 ,000,$20 ,000. Any of these professional services, but then you hire an accountant, it's like$1 ,000. But then the client has an expectation that they'll get the same level of attention from that. And we have to kind of do our best to bend over backward to make sure that that happens. It's an extremely challenging profession. And when you add to it, the emotion that comes from personal tax return preparation, Many people do not understand tax.
23:01They don't want to understand tax. And it's the last thing that they're interested in. It's actually probably the most uninteresting thing for people. And then all of a sudden they're used to getting a refund, but now they have to pay. And, you know, obviously we made some kind of a mistake. Right. So then it's more, you know, it's an emotional conversation. So this is why and oftentimes it's simply a matter that they earned more and they withheld less because of some change in their payroll department at work. and that's the only reason why they owe money and but it's an emotion but we're the ones that we have to break the news so many accountants because of the and there's another issue with personal tax returns they only come up once a year so how do you build a workforce that essentially does nothing all year except for during the tax season how do you keep them paid while also completing what's essentially a low, low margin engagement.
23:56And so these are all the challenges that have many business owners that are accountants saying we're only going to focus on business returns because we can do their monthly bookkeeping. So we have something to keep all the team busy and actually pay our bills. And businesses oftentimes, especially if they're large ones, it's less of an emotional conversation. So, but we've, I'd say maybe we're brave. We just take on these clients. And I actually love working with personal tax return clients. I don't want to sound like I'm complaining. It's actually one of the most rewarding things when you're the only person that's available that actually cares and that wants to do a great job.
24:33And I'd say one differentiator about our firm, I genuinely really, really, really do care about the client experience. Like I want the clients to have a great experience. If something falls short, we will do anything possible to fix the issue. and many companies can't say that. Many companies treat clients as a disposable unit rather than as an individual. Do you think a lot of this also has to do with technology? And I think a lot of industries are going to go through this. People say, oh, I can get this technology that can do it for free. I could do my taxes online for free or whatever it is.
25:08And I think a lot of industries right now are going through the technology can do it for cheap, But I've had really bad experiences with those technologies before. And I think you want to do it until that happens. And then you realize you should have gone to paying the service is going to be better for some people. So, yes, I mean, when is the last time that you called a business of any kind and been happy that you got the AI chatbot? It never actually solves the problem. So companies now, because of their investors, feel pressure to be AI. And there's jokes about this on social media where a company, you know, the investors say, we need AI.
25:55So then the manager tells the operations team, we need AI. The operations team tells the client, you guys need AI. The client says, I don't want this. This doesn't work. And it sucks. So then it goes back to the chain all the way back to the CEO. And the CEO tells the investors and they say, well, I'm not going to invest in your company unless there's AI. So what do you do? The final user doesn't want it. I've never, you know, even if there's an issue with my Uber order, if I go to the AI chatbot, it rarely actually solves the problem unless it just gives a refund. That's probably the only time where it's like, OK, you gave me my dollar 22 cents back for the sauce.
26:34I never got cool. So I'd say we're very far away. You know, the example I gave is we had one financial statement that was internal, not a client one that was literally adding columns and perplexity botched it or cloud or whatever, whatever software my internal accountant was using. So I think we're very, very far away from having these actually working. And as far as your comment about people using TurboTax, TurboTax is a very good tool for people that have a simpler tax situation. When it gets more complicated, they just need professional help. When you think about the ability to scale, was there a certain marketing strategy that you use to acquire customers?
Read the full transcript
27:15I'd say the best thing is to provide an amazing customer experience. I'd say that's the number one most important thing for any service-based business, regardless of what the service is. Anywhere from, you know, a good friend of mine owns a construction company doing custom home renovations. And it comes down to the exact same thing. It's remarkable how similar our businesses are. And I talked to my friend, you know, a few times a week about business. And it's almost as if we own the same company. Because it really just comes down to, are you providing an amazing client experience? If they do an amazing job on this person's kitchen renovation, they'll get hired for the bathroom renovation.
27:54They'll get hired for the facade. They'll get hired for the screen and portrait deck. And it's the same thing with us. If we do an amazing job on somebody's business setup, we'll become their accountant. hopefully for many years for their small business or their personal returns. A lot of people say entrepreneurship is a really lonely place. How do you find other people that you can relate to, that you can bond with? I recommend to anybody to join a network such as, and I'm not talking about the lead referral networks because those are always a little bit pitchy and a little bit kind of, they just feel a little bit, for me, I've never enjoyed those.
28:31But I'm talking about ones that are, I guess, more intimate where you form relationships with other business owners, things such as entrepreneurs organization, Vistage, or for people that are higher income, YPO, Young Presidents Organization. So these are all ones that some of them have an income requirement. I believe for EO, it's 1 million. And I believe for YPO, it's 15 million per year revenue. But many don't or many have smaller ones or there might be entry programs into those. so I recommend joining one of those because you are absolutely correct it is extremely challenging being an entrepreneur where every decision you make you have skin in the game so yes that's a very relevant question you're correct about that George thank you so much for today I learned a lot I learned a lot like you said you can't just ask someone these questions if I ask AI it will probably give me the wrong information and you you need the experts to talk to so george d mob always great chatting with you and thanks for coming on the show amazing thank you so much
From the publisher
Daniel opens the episode with the question many people wonder but rarely ask directly: how do the ultra wealthy pay less taxes? George explains that there is a major difference between people earning high income through work and the ultra wealthy whose net worth is tied to appreciated stock or other assets. The “working rich” may earn a lot, but they often still pay significant taxes because their income is active and taxable. Billionaires, by contrast, may see their net worth grow without triggering taxes because appreciation is not taxed until the asset is sold.
From there, George breaks down how wealthy people can borrow against assets instead of selling them, why real estate owners can reduce taxes through strategies like cost segregation, and why everyday employees often miss basic employer benefits like retirement contributions. For entrepreneurs, George highlights defined benefit plans, SEP IRAs, solo 401(k)s, bookkeeping reviews, and fraud prevention as major areas where business owners can save money or protect themselves.
The episode also moves beyond tax tactics into the future of accounting. George discusses why the CPA industry is facing a major shortage, why many younger professionals are leaving the field, and why AI still struggles with real accounting complexity. He argues that while tools like TurboTax can work for simple situations, complicated tax planning still requires experienced professionals who understand the client, the details, and the consequences.
Key Discussion Points
- George explains that ultra wealthy people often build net worth through appreciated stock, which does not create a taxable event until they sell, while the “working rich” still tend to pay significant taxes on active income.
- He breaks down the idea of borrowing against assets, where people may access liquidity through loans instead of selling appreciated securities and triggering taxes.
- George says smart people often miss basic tax opportunities, including maxing out employer retirement benefits, using cost segregation for real estate, and setting up retirement plans like SEP IRAs, solo 401(k)s, or defined benefit plans.
- For entrepreneurs and freelancers, George warns that fear of being audited can cause people to overpay, but he also cautions against reckless social media tax advice, especially extreme deductions like luxury vehicle write offs.
- The conversation explores the massive shortage of accountants, with George explaining that many baby boomers are leaving the industry while younger generations are choosing other career paths.
- George argues that AI and tax software can help in simple cases, but complex tax situations still require professional judgment, responsiveness, and a strong client experience.
Takeaways
The ultra wealthy often pay less tax because much of their wealth grows inside assets, not through ordinary income. Taxes are usually triggered when assets are sold, not simply when they appreciate.
Business owners should regularly review their own bookkeeping. George says companies often find wasted subscriptions, unnecessary contractors, payroll issues, or even fraud when they actually audit their books.
Freelancers and gig workers may overpay because they are afraid to deduct legitimate business expenses. George’s point is not to be reckless, but to understand what is normal, documented, and defensible for your industry.
One person businesses need structure early. George discusses tools like entity setup, 83(b) elections, and tax advantaged planning that can dramatically affect outcomes if a company becomes valuable later.
The coming generational wealth transfer could create major tax and planning consequences, especially for families that do not set up trusts, estate plans, or clear structures in advance.
In professional services, customer experience is the real growth engine. George says the best marketing strategy is doing great work, being responsive, and creating the kind of experience that turns one engagement into a long term relationship.
Closing Thoughts
George Dimov’s Founder’s Story episode is a practical, revealing conversation about taxes, wealth, entrepreneurship, and the future of accounting. George makes clear that taxes are not just about what you earn, but how you earn it, how your assets are structured, what benefits you use, and whether you plan before the moment arrives. For founders, freelancers, investors, and families preparing for wealth transfer, the episode is a reminder that good tax strategy starts early, requires documentation, and depends on having the right experts around you. His biggest message is simple: do not rely on fear, social media advice, or AI alone when the stakes are high. Get the right structure, review the numbers, and build with strategy before the tax bill arrives.
Today's Sponsor:
Start with Upwork, the platform to find, hire, and pay expert freelancers across marketing, design, development, and operations. Visit https://www.upwork.com to post your job for free and get matched with top talent.
Support longevity in business and life with CocoaVia, a daily cocoa flavanol supplement designed to support healthy blood flow, heart health, and brain function. Go to https://www.cocoavia.com/ and use code FOUNDERS for an extra 20% off, or find it at your local Sprouts.
Limited Time Offer – Make healthy eating simple. Get Huel today with my exclusive offer of 15% OFF online with my code FOUNDER at https://www.huel.com/FOUNDER. New Customers Only. Thank you to Huel for partnering and supporting our show!
Stop overthinking your first sale and launch with Shopify, the platform that helps you build, sell, and keep your business running from day one. Start your free trial today at https://www.shopify.com/foundersstory.
Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.
