What if there were a legal strategy that could dramatically reduce—or even offset—your capital gains tax liability while preserving more of your wealth for future investments? In this episode of Build It to Billions, Brett Swarts sits down with financial strategist Elliot Omanson to explore the concept he calls the “tax coupon” and how proactive tax planning can help entrepreneurs, investors, and business owners keep more of what they’ve worked so hard to build.
Elliot shares practical insights into advanced tax strategies, capital gains planning, and the importance of preparing well before a major liquidity event. Together, Brett and Elliot discuss how thoughtful planning can unlock greater financial flexibility, create more opportunities for reinvestment, and position families to build lasting wealth. Whether you’re selling a business, real estate, or another highly appreciated asset, this conversation offers valuable perspectives on making smarter tax decisions before it’s too late.
Episode Highlights Here:
Brett
Before we jump into this episode, I would invite you to join our community to help you become a better steward, scale to billions, and ultimately give more or all of it away. All I want you to do is to click the subscribe button right now. I love your support, it’s incredible to see your comments, and we’re just getting started. I can’t wait to go on this journey with you. Thank you so much for subscribing. It means the world to me. Welcome to the Build to Billions podcast, where we guide successful entrepreneurs and investors on their journey from millions to billions. We really, the key to scaling and compounding your wealth and life starts every single day with the mindset and practice of stewardship of ownership and applying billionaire biblical principles. Our ultimate goal is to have to scale and compound your wealth and life, so you can give moral all the way to help MVPs. My name is Brett Schwartz. Each and every episode, we’re joined by the world’s top entrepreneurs, millionaires, or billionaires, and they share their secrets, wisdom, and insights with us, so we can all level up and make a bigger impact. I’m excited about our next guest. He is focused on like a laser and helping us to keep more of what we’ve earned. He entered the financial advising business after serving the US Army, and during that time he watched his two younger brothers build their career as investment advisors, and being able to capitalize on their experiences allowed him to identify early on what kind of firm he wanted to be part of, and he is licensed in Series 766 Life and Health, and he is now helping people build wealth in a meaningful way with OFFI. We’ll talk a bit more about that, and his new book, Keep What You’ve Earned. Please welcome the show with me, Elliot Omanson. Make sure I pronounce that last name Elliot correctly again, because I know
Elliot
Omensen, but everybody says Omansen, so
Brett
Yeah, there it is. I gotta really, I gotta really pronounce that. Oh yeah, can you give us a little bit more about your story and your focus?
Elliot
Yeah, yeah, you know, obviously I haven’t always been here, right? And one of the things that Ilike to go a little bit further back than most people probably care about, but I was in a podcast, and somebody asked, well, how did both your brothers and you all end up in this as financial advisors? Right, clearly your parents did something wrong, but you know, I never really thought of it before, and, and at that time, like, the memory that came back to me was being 10 years old, coming over my first job, babysitting, and it’s the 80s, so you know, there was no bicycle helmets, airbags, you know, there’s a little bit different of a time, but my mom was waiting for me with a three by five spiral bound note card book and she had me make columns in it and one was who I worked for the data I worked for them how much they paid me and then I had to put 10% to tithing 50% to my savings account and 40% my favorite column right spending, and by the time I was 15, I think I had probably like $5,000 set up in my bank account. And then she sat me down with a family investment advisor in my kitchen, and you know, it was kind of funny. Took me like 20 minutes to get this guy to my mom, was she sat us down, then she went to teach piano, and it took me like 20 minutes to get him to stop talking about how hot he thought my mom was, so he can actually focus on business, and I made my first investments, right, and then at 17 I sold my first, the first time I ever sold out something to use for myself, and went to Europe for the summer with some friends, and so by the time I was 17 year sold, I’d already gone through this whole life cycle of working, earning, saving, investing, and realizing a gain on my investment, all at the hands of my mother. Right? How many? How many people get that right? So, you know it’s not surprising, all three of us, when you’re raised by a woman like that, all three of you end up in the money business, right? So,
Brett
love it, that’s really cool. What an awesome mom, what a crazy story to take advantage of for my kids to be really clear. We didn’t think we did the Rich Dad Poor Dad Cash Flow Quadrant game, yeah, we’re working, working through, and like, what does that mean to get out of the route race, and how did that look? So, but that’s great, like writing it down. That notebook, did you keep it for a long time, or where’s the notebook now?
Elliot
You know, I have no idea. You know, I wish I had, because I think that’d be a really neat artifact from my past to have hung on to. Now, what’s funny about it is, at the same time I had all that going for me, I was also a total screw up in school. I hated school. I was arrested and thrown out of high school, never went to college, and by the time I was 30, I was like really struggling, like I was married, I had two kids. I think I was in the middle of being evicted for the third time. I didn’t have a car, it was repoed, like you know. So, even though your parents did this really good job giving to this foundation, you’re, you can still screw it up. And, and, and I’d always wanted to join the military. I’d even tried earlier. Her, but I, my wife didn’t really want to be married to a guy in the army, but by the time I was 30, I was like, I didn’t know what else to do, and I felt like I had 90% of what I needed, I was just missing something, and I was driving down the road in a rental and looked over and saw an armed forces recruitment play.
Brett
So, if you like this little, short clip of the interview I just did, click over here to watch the full interview, and please don’t forget to subscribe. Thanks so much, everybody
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About Elliot Omanson
Elliot Omanson is a financial strategist, entrepreneur, and founder of OWLFI Strategic Advisors, where he helps business owners, investors, and high-net-worth families navigate complex financial decisions with an emphasis on tax efficiency, business optimization, and long-term wealth preservation. A U.S. Army veteran, Elliot transitioned from military service into the financial advisory industry and has built his career around helping entrepreneurs create intentional strategies before, during, and after major liquidity events.
Through his advisory work, speaking engagements, and the Backseat Ballers podcast, Elliot educates business owners on advanced tax planning, exit strategies, and legacy-focused wealth management. His practical, forward-thinking approach empowers entrepreneurs to minimize unnecessary taxes, protect their assets, and create lasting financial freedom for future generations.
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