2380 - Smart Tax Strategies for Business Owners Using Trusts with Sally Gimon

9 Mar 2026 · 17 min · 6 chapters

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In short

Smart tax strategies for business owners using trusts, focused on reducing federal/state taxes and avoiding overpaying; includes discussion of filing status changes and how CPAs may miss trust-based options.

Guest

Sally Gimon. Runs/teaches tax strategies for online businesses; says she personally avoided a large short-term capital gains tax bill after a 2019 real estate win by researching and setting up trusts. Claims background in real estate and running a mastermind; promotes affiliate partnerships with CPAs.

Key claims

Many CPAs focus on tax code, not trust/contract law; IRS guidance allegedly disfavors spendthrift trusts but Congress controls tax code. Trust structures can shift taxation so investors/beneficiaries pay less or no taxes. Filing married separately vs jointly can change tax cost.

Notable examples

Her 2020 story of owing $94,000 after bracket change; real estate apartment owners using depreciation; a digital marketer saving $5,000+ by switching filing status; references to Rockefeller spendthrift trust and Robin Williams’ beneficial trust.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Introduction of Sally Gimon

0:45 to 1:39

Host introduces guest Sally Gimon and discusses her interests.

“Visit podverified.com if you'd like to be featured as a future guest.”

Sally's Tax Journey

1:39 to 4:23

Sally shares her personal tax experiences and the importance of trusts.

“And before we kind of get going into your superpowers and sharing some great tips, you always love finding what high-level leaders do for fun or kind of geeking out on outside of work.”

Understanding Tax Strategies

4:23 to 11:01

Discussion on why businesses overpay taxes and common strategies to save.

“My superpowers, my personal story, I did very well in real estate in 2019, paid off all my debt, had$50 ,000 in my bank account.”

Tax Breakthrough Resources

11:01 to 13:57

Sally explains her resources for tax savings and how to access them.

“And it's the middle class that gets squished.”

Sally Gibbon's Course and Affiliate Program

14:01 to 15:10

Learn about Sally Gibbon's course and how her affiliate program works.

“Use the link saladgibbon.com because that'll put it directly onto your course.”

Thank You and Closing Remarks

15:10 to 15:22

The hosts express gratitude to Sally Gibbon and wrap up the episode.

“Well, Sally Gibbon, thank you so much for joining us.”
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Transcript

Automatic transcript. May contain errors.

0:03Welcome to the Thoughtful Entrepreneur. If you're committed to growing your business by serving audiences with generosity and real expertise, you're in the right place. This is a daily 15-minute show featuring leaders who believe real impact comes from generosity, not hype, which means as a listener, you're going to get the good stuff. In fact, we created podverified.com to give thoughtful leaders like you free tools to show up better on podcast stages like this one. That includes your free podverified score, free podverified guest training, a free media kit builder, and so much more. It's the first ecosystem of its kind built by podcasters who genuinely want to help guests thrive and grow in podcasting.

0:46Visit podverified.com if you'd like to be featured as a future guest. I'm Josh Elledge. Let's get into it.

1:21how much we pay in taxes as business owners. We got operations going on. More importantly, how much we're overpaying likely. But that's just a tease. Sally, before we get into that, first off, thank you for being here. Well, thank you for having me, Josh. I really appreciate it. Yeah. And before we kind of get going into your superpowers and sharing some great tips, you always love finding what high-level leaders do for fun or kind of geeking out on outside of work. What have you been into lately? I am a humongous hockey fan. I love the Washington Capitals. And last night, they had a fantastic game.

1:58I listened to my computer, and I went to bed happy. So what is it now? Do they always have the kind of season that they're having this year? actually they're not having the best of seasons this year but when they won the stanley cup back in 2018 i was on the nile river with my dad getting up at two o 'clock in the morning on a ship and all the egyptians because the world cup was happy at the same time they became hockey fans that's very cool so what do you what do you like tell me about the hockey cry so i've gotten you know i've gone to hockey games so here in orlando we have the solar bears uh which is uh you know minor league team.

2:41And we've actually, I've seen the race or not the race, but who's the Tampa Bay team? Lightning? The Tampa Bay Lightning. Yeah. I didn't think that's it. So it's a star. Clearly not a huge fan. I've just, you know, when friends have invited me, I'm like, yeah, sure. Hockey crowds are kind of cool. Tell me what your observation of hockey crowds is. True story. When I was in elementary school, we were living in Cherry Hill, New Jersey, right across the river from Philadelphia. Dave Schultz is still the number one penalty maker in all of the NHL. When you score a goal or have an assist, you got a case of Tasty Cakes.

3:20He and his wife had no children, so he would give us, my brothers and I, each a box of Tasty Cakes. My mom hated him because there was a picture. He gave her free tickets. My mom didn't drive, but this was the 70s. He had some guy's hair wrapped around his fist and slamming his head into the ice, and she's like, You'll never be a hockey fan. Well, you don't tell someone you'll never be because that changed it for me. You know, when growing up in Kalamazoo, Michigan for a year or so, or kind of West Michigan, we'd go to the Kalamazoo Wings games. And as a kid, you know, I was in fourth, fifth, sixth grade.

3:56And I really do have some great memories of going to see those games with my dad. And, you know, of course, yeah, when there's a fight, it's kind of like, oh, my gosh. You know, as a kid, he's like, I can't believe we're watching a fight. And so anyway, that looks like a tough sport to do. I never played. I can skate, but I can't go backwards. So yes, I could never be a hockey player. All right, Sally, let's talk about tax savings. Give me an overview of your superpowers, what you do. My superpowers, my personal story, I did very well in real estate in 2019, paid off all my debt, had$50 ,000 in my bank account.

4:35And on October 4th, 2020, started in March, my CPA calls me and says, congratulations, your tax bracket went from 22 % to 24%. You owe the federal government$94 ,000 in short-term capital gains. I only had$50 ,000 saved. Not congratulations. I had read an article about the Rockefeller Spendthrift Trust. I took five months to research it and I started both my business trust, the state, federal and state income taxes because I have three online businesses. And then also the beneficial trust. So investors no longer pay taxes and started teaching in my mastermind in my real estate group. Long involved story.

5:16Had a falling out with the gentleman who ran the real estate group. So my thinking of the results coach said, you need to start your own business. I thought she was crazy, but I get to help people nationwide save five figures, six figures in taxes, and they love me. I mean, I just had someone send me cookies for Christmas saying, thank you for saving us taxes. So let me take that to a party so I don't have to make my own cookies. Yeah. Well, Sally, what's going on? Why are businesses paying too much in taxes? We've got like, you know, we might have an accountant or CPA that's helping us. We might, you know, keep our books squeaky clean.

5:52why are we still paying too much in taxes? The reason why is no offense to CPAs, but they go to a tax school. This is contract law and trust attorneys. There are over a million attorneys in the United States and only 4 % are trust attorneys. They study a book in law school called Scott and Nasher on Trusts Fifth Edition. There's an entire chapter dedicated to the fendthrift trust. It comes from England, way back when King Henry VIII, that famous king who chopped off his wife's heads, he started the Church of England so he could divorce his wives. Hey, murder a few ladies, start a church. Why not?

6:29He went to go tax the lords and ladies of England. They went back to the 13th century to the Magna Carter and said, oh, no, no, no, it's contract law. He came to the colonies, well, we're still part of England, and when our tax structure started in February of 1913, the super rich families, the Rockefellers, the DuPonts, the Carnegie's, and the Kennedy's made sure they could save taxes. Well, if they can save taxes, we can save taxes. And my goal is to teach this to as many people as possible. All right. Do you mind maybe sharing a few kind of high level things that, what are some of the most common missed tax saving strategies that you recommend?

7:09If you just want to name one, two or three, it's completely up to you, but I'll let you have it. Well, the really sad thing about it is your CPA or your financial advisor will probably pull up the August 3rd, 2013 memo that the IRS literally wrote a memo saying they do not like tax code 643B and they do not like the irrevocable, complex, discretionary, non-grant or spendthrift trust. Well, it's their opinion. The IRS cannot change the tax code. Only Congress can. The Kennedys, our current president's father, started this trust in 1972 when Frank and Donald Trump got sued by the city of New York.

7:51There's an actual news article where Frank Trump says he'll never be sued again. You can be sued, but all lawsuits become frivolous and go away. Famous, unfortunately, Robin Williams, the actor, he had the beneficial trust. Yes, he committed suicide, but his children pay no royalties on any of his works. I just watched Mrs. Doubtfire. I mean, the super rich know about this. I think everybody should know about it. You'll have another arrow in your quill. Maybe it's not right for you today, but maybe in six months or six years, you're like, I just went to another tax bracket. Why am I paying so much?

8:31How can I save these taxes? Yeah. At what level, Sally, does it really make sense to say, listen, you're going to have to, at your taxable level, you can't afford to only just work with a CPA at this. You really need to start working with a strategist and someone who understands contract law and someone who can really develop some of these systems that by default, you're probably never going to do. Your CPA, it's just not a part of their repertoire. correct true story i do a mastermind every monday evening at five o 'clock i had an adult son who got on there his mom and dad have three um apartment buildings in brooklyn you'll walk up apartment buildings they've had them for 27 years they were trying to figure out if they were going to sell them or if they were going to keep them because depreciation on real estate is 27 and a half years you know answered his questions he set up a 30 minute tax breakthrough session with me send him the information.

9:30Two weeks later, he writes back to me and he says, my CPA says you're lying. I'm like, well, tell your CPA, here's a book that they study in law school. Three weeks after I sent that email, somebody gets on my calendar. It is the CPA that's their CPA. And he's just like all my clients, they're all immigrants from other countries who bought these apartments 27 years ago. He goes, how much can you save them? He and I work now hand in hand. He tells his clients, I have an affiliate program. He gets paid an affiliate for telling them. His clients are either selling the apartment buildings or they're going to keep them to continue to save rental income taxes on it.

10:06And he's just fantastic. Another horrible story, two years ago in Charlotte, it was multifamily meeting. I bought a ticket. I live two hours from Charlotte, went down there two days, went to lunch with five other people, tell them about the trust. One of the guys, he's also up in New York. He has a hedge fund and he, he, he sets up in the meeting with me, get on the meeting, go spicy pieces, you're lying, got off the meeting and all his clients don't know how they could be saving taxes and things like that. So some people are open to it. Some people are not open to it. I mean, it's in the IRS tax code.

10:49It's there for, you know, the rich know about it. Unfortunately, the working class or the middle class don't know about it. And that's where all the taxes come from. There's a safety net if you're poor. There's a safety net if you're rich. And it's the middle class that gets squished. Yeah. Yeah. Well, Sally, what does it look like working with you? um i do a lot of uh free videos on tiktok and youtube and other things like that that's where i get my clients and then when you make an appointment with me i take you out to a free website called nerdwallet.com to show you there's four ways to file your taxes most expensive way is single then there's head of household you're divorced but have kids who are 18 or under then there's married filing separately and then the cheapest way is married filing jointly quietly on January 1st of 2025, the IRS changed married filing separately to match filing as single.

11:49It's insane. When I tell people this, this is a true story. On July of last year, July of 2025, I had a woman contact me. She saw one of my videos. She's a digital marketer on TikTok. In the first five months of being a digital marketer, she made$100 ,000. She talked to her CPA and he said, your husband has a W-2 job. You're making 1099 income. You need to file separately. I'm like, Oh no, no, no. Let me just show you this one. They would save over$5 ,000 just making that change from filing, uh, filing married separately to filing married jointly. And she's just like, I'll be your client now. You know, cause I, you know, I just taught her that and she had no idea.

12:30And she's like, why'd my CPA not know this? I'm like, I don't know. So she contacted me a week later because she made another point with her CPA. He's like, oh, I didn't know they did that. I'm like, oh, dude, you're a CPA. You should know how taxes have changed. Yeah. Wow. All right, Sally, let's talk about, to our friend that's listening, you mentioned some resources. I know that if they go to sallygimmon.com, it's going to take them to a website where you've built, it looks like a video course here, and it's on a website called The Great Discovery. but if they go to sallygimmon.com, they can access this.

13:03Do you mind sharing a little bit about what this is? It's the great discovery is, have you ever heard of Six Sigma? Yeah, yeah. My brother's a black belt in Six Sigma, so that's why I'm partial to this. It's their fourth way of doing things. The great discovery, you're going to sign up to be a free learner, and my class can be translated into 165 different languages. When you go out to the class, you can translate it into whatever your native language is. And then you're also going to get three articles from Forbes magazine I did not write. You're going to get two pages of case law to research this to your heart's content, and then examples of people saving thousands of dollars.

13:43I set this up because when I used to send this to somebody an email, it'd be too big to send in an email, and it would crash their email system. So I'm like, hey, here's where you can get the information. Yeah. So it's hosting this, and it's free. It's free. Exactly. When you do go to the Great Discovery, the class is called - Use the link saladgibbon.com because that'll put it directly onto your course. But what is the course? It's Save U.S. Taxes Legally. Correct. Correct. I have, I think, about 700 followers there right now. I don't advertise it that much. I just let people know about it. Well, very cool.

14:20Your other website is thetrustisyou.com. uh what do people what's that website that's my squeeze page you'll get the free uh free video you can set up a 30 minute tax breakthrough session with me um you can also sign up to be an affiliate uh with my affiliate program it's free you get your own link and but the system i use for my crm is go higher level so if you give someone so let's say i give that to you josh you give someone your affiliate link, they're tagged to you. I talk to them on January 30th. They don't buy the trust until May 1st. I know on May 1st, hey, Josh Eldridge is the affiliate.

15:01I contact you saying you want$1 ,000 by PayPal, by Zelle, or if you want me to wire it to you, what are your instructions? Got it. Got it. Well, Sally Gibbon, thank you so much for joining us. Again, your website, sallygibbon.com or thetrustisu.com. Thank you so much, Sally, for joining us. Thank you for the great tips. I appreciate you having me. I hope you have a wonderful 2026.

15:27Thanks for listening to the thoughtful entrepreneur. If your goal is to grow your business, increase revenue and build authority without gimmicks. This show is designed for you. Each episode gives you practical insight from leaders who have turned trust and credibility into real business results. If you value short, thoughtful conversations that respect your time, make sure you're subscribed. We publish daily 15 minute episodes focused on growth that actually compounds. And if you're interested in being a guest, or you want to turn podcast appearances into measurable business growth, visit podverified.com.

16:03You can start for free with your pod verified score, along with free podcast guest training and a free media kit builder. These tools are built to help you get booked on better shows, deliver stronger interviews, and convert audience trust into revenue. No more desperate sales. You truly can enjoy all the business you like by generously sharing your wisdom. Everything we offer is built by podcasters for guests with a focus on trust, organic growth, and long-term business success. Thanks again for spending your time with us. I'll see you next time. mouths for

From the publisher
Unlocking Advanced Tax Savings: How Strategic Trusts Empower Entrepreneurs with Sally Gimon

In a recent episode of The Thoughtful Entrepreneur Podcast, host Josh Elledge sat down with Sally Gimon, a dedicated Investor and tax strategist at The Trust is You, to dismantle the common frustrations business owners face during tax season. Despite having experienced CPAs, many entrepreneurs find themselves blindsided by massive tax bills—a pain point Sally knows intimately from her own early days in real estate. Their conversation dives into the specialized world of non-grantor irrevocable spendthrift trusts, a legal framework used by America’s wealthiest dynasties to protect assets and defer taxes. This episode serves as a vital resource for high-achieving founders looking to move beyond basic deductions and into the elite level of wealth preservation.

Beyond Compliance: Why Your CPA Might Be Missing Millions in Savings

Most business owners rely solely on their CPAs for tax advice, but there is a fundamental gap between tax compliance and specialized trust law. CPAs are expertly trained in the tax code, yet only a tiny fraction of professionals are versed in the nuances of contract law and the specific IRS codes that govern complex trusts. This often leads to a "compliance trap" where entrepreneurs follow the rules perfectly but still overpay because they aren't utilizing the same legal structures as the Rockefellers or the Kennedys. By bridging this gap, business owners can move from a reactive state of paying what they're told to a proactive state of legally shielding their hard-earned capital.

The core of Sally’s strategy revolves around Tax Code 643(b), which allows certain types of trusts to defer capital gains and passive income legally. While the IRS may issue memos expressing disapproval of aggressive strategies, it is important to remember that only Congress has the power to change the tax code itself. For business owners with appreciating assets like real estate or intellectual property, these trusts offer a dual benefit: significant tax deferral and robust asset protection from creditors or lawsuits. Implementing these structures requires a shift in mindset, moving away from "income management" toward "asset orchestration" within a protected legal entity.

Ultimately, the goal of advanced tax planning is to provide the founder with more liquidity to reinvest in their mission and legacy. Sally emphasizes that these tools are not "loopholes" but are established parts of the American legal system designed to encourage long-term investment and wealth stability. By leveraging educational resources and weekly masterminds, entrepreneurs can demystify these complex structures and determine if they are ready to implement a spendthrift or beneficial trust. Taking control of one's tax destiny is about more than just numbers; it’s about ensuring that the value created by the business remains within the family or the organization for generations to come.

About Sally Gimon

Sally Gimon is an experienced Investor and a leading advocate for tax education through her platform, The Trust is You. After facing a nearly six-figure tax bill early in her real estate career, she dedicated herself to uncovering the wealth-preservation secrets of the ultra-wealthy. Today, she helps business owners across 165 countries understand trust law to protect their assets and slash their tax burdens.

About The Trust is You

The Trust is You is an educational and strategic resource center focused on democratizing advanced tax-saving tools. The company provides video courses, weekly mastermind sessions, and specialized consulting on non-grantor irrevocable spendthrift trusts. Their mission is to empower entrepreneurs with the knowledge to legally minimize taxes and protect their legacy using proven trust frameworks.

Links Mentioned in This Episode

  1. The Trust is You Official Website
  2. Sally Gimon on LinkedIn

Key Episode Highlights

  1. The CPA Limitation: Understanding why compliance-focused accounting often overlooks advanced wealth-preservation strategies.
  2. The Power of 643(b): How this specific tax code allows for the legal deferral of capital gains and passive income within a trust.
  3. Asset Protection: Why spendthrift trusts are the gold standard for shielding your business and personal assets from litigation.
  4. The "Rockefeller" Strategy: Lessons from America’s wealthiest families on using contract law to maintain multi-generational wealth.
  5. Democratizing Knowledge: How Sally’s free resources are making elite tax strategies accessible to small and medium-sized business owners.

Conclusion

This conversation with Sally Gimon highlights that while the tax code is complex, it contains powerful provisions for those willing to look beyond standard accounting. By integrating trust law into your financial strategy, you can transform your relationship with the IRS and keep more of your wealth working for you.

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2380 - Smart Tax Strategies for Business Owners Using Trusts with Sally GimonThe Thoughtful Entrepreneur · 17 min
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