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Episode Summary
You just got the call from your CPA. You owe a number that has commas in it and you have seven days to write the check. The income statement was a great year. The tax bill was a great year for the IRS. You know Mitt Romney and Elon Musk pay rounding errors on this stuff and you’re sitting at thirty or forty cents on the dollar wondering what the elite know that you don’t. The gap is not access. It’s a missing seat on your team. Your CPA prepares the return. Your banker manages the line. Your wealth manager runs the portfolio. Nobody is sitting between them architecting how to keep more of what you earn. I sat down with Roger Roundy, who I’ve come to call a tax architect, to get into how tax mitigation actually works, why most owners think their tax preparer is their tax planner (and why that’s a six-figure problem), the difference between accumulation, distribution, and legacy planning, and how the dollars you stop sending to the IRS become the funding source for the rest of your plan: the executive hire, the Module 8 — Executive Compensation, the operator transition.
Top 10 Takeaways
- Your tax preparer is not your tax planner. Most owners assume they are. That confusion costs six figures a year.
- Your CPA gets paid the same whether you owe a hundred grand or ten grand. The incentives don’t align.
- Tax mitigation is a missing seat on your team, not a replacement for the seats already filled.
- Tax planning happens in the year you have the income. March is too late to fix last year.
- Mitigation runs through three phases (accumulation, distribution, legacy). Most owners only get planned around one of them.
- The IRS has the best SEO in the country. Google any strategy and you’ll talk yourself out of it.
- Every tax incentive exists because Congress wanted a behavior. Stay inside the intent and you stay in the black.
- The elite don’t pay taxes because they have teams. Access isn’t the gap. Application is.
- Your tax savings aren’t a fancier boat. They’re the funding source for the rest of your ownership plan.
- Below a hundred grand of annual tax bill, the architecture isn’t worth the work. Above it, the math flips.
Sound Bites
“I think the disconnect in our country, realistically, is that most people think their tax preparer is their tax planner.” (@00:07:59) — Roger Roundy
“We live in a very capitalistic society. Once someone sees an opportunity to save money in taxes, those who want to be aggressive will abuse the code. That’s the IRS’s job, is to sniff out the abuses.” (@00:12:10) — Roger Roundy
“Tax planning happens in the year you have the tax problem. Don’t come to me in March and April and say, hey, what can I do for last year?” (@00:37:01) — Roger Roundy
“Your job is to make as much money as you possibly can. I can’t help you make any more money. My job is to help you keep as much money as you possibly can. Don’t be afraid and don’t let the tax tail wag the dog.” (@00:39:24) — Roger Roundy
About This Episode
Roger Roundy is the founder of Strategic Associates, a tax mitigation consulting firm based in Northern Utah. Coming out of the risk management and insurance world, Roger fell into tax planning when he saved a client too much on health insurance premiums and had to figure out where the savings went. Over the last 12+ years, his firm has built a vetted catalog of advanced tax mitigation strategies (831(b) captive insurance, leveraged charitable gifting, tax credits, and more) that bring the same playbook the Fortune 500 uses down to small and mid-sized owners. He’s not a CPA and he doesn’t replace one. He sits between the CPA, the wealth manager, and the estate planner as the missing team member focused on income tax mitigation.
Resources Mentioned
- Strategic Associates — Roger’s tax mitigation consulting firm.
- 831(b) Captive Insurance — The first strategy Roger built his practice around. Lets a business owner take a deduction for setting aside money to protect their own risk, with long-term capital gains treatment on the way out.
- Section 401(k) — Referenced as the most well-known example of a tax incentive Congress created to drive a behavior.
- Augusta Rule — Referenced as one of the smaller deductions most CPAs help with.
- Tax Planning Leadership Institute — A training arm Roger is building to teach more advisors what his firm does.
Connections
Phase + Module:
- Module 2 — Expand Knowledge — Tax mitigation is one of the biggest knowledge gaps most owners don’t know they have
- Module 8 — Executive Compensation — Tax savings as the funding source for the operator hire and the comp plan
Milestones:
- Milestone 6 — Transaction Value — Tax mitigation at the sale event, where the tax bill is biggest
- Milestone 2 — Cash Flow Targets & Sources — After-tax cash flow is the number that actually feeds the owner
Concepts referenced:
- Distributable Cash — What’s left after the IRS takes their cut
- Free Cash Flow — The pool tax mitigation actually grows
- Capital Allocator — The owner seat that decides where saved dollars go next
- Independence by Design™ — Roger named the throughline at the close: the design is missing a piece, and tax mitigation is often the piece