How To Stop Overpaying On Taxes W/Michael Uadiale
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Episode Description
In this episode of the On The Rise Podcast, host Jeremy Dyer sits down with Ben Reinberg, a prominent commercial real estate investor and founder of Alliance CGC, to talk about why hard assets remain the most reliable path to generational wealth — especially in a market cycle defined by trillions of dollars in maturing loans and ongoing economic uncertainty. Ben breaks down why hoarding cash is the wrong response to market volatility, what makes medical office one of the most recession-resilient asset classes available, and why the ability to hold is the single most important variable in any real estate investment. He also shares what separates capital raisers who consistently win, how to evaluate an operator beyond the pitch deck, and what investors sitting on the sidelines in 2026 should be doing right now.
Summary
1. The Painful Origin Story That Drove a Mission Michael arrived in the US from Nigeria, passed his CPA exam, landed a job in Silicon Valley with stock options, and was advised to find a tax professional. He paid a significant fee, trusted the process — and then sat across the desk from that advisor learning he owed the IRS $80,000. The advisor had done nothing. That experience became the foundation of Michael's entire practice and his conviction that too many people are being failed by the profession they trust most.
"Too many business people are every day overpaying their taxes — not because the government is asking them to. That's the tragedy of our profession."
2. Taxes Are Not a Punishment — They Are a Roadmap The tax code was not written by accountants. It was written by lawyers, and it functions as a set of incentives designed to direct capital and behavior toward outcomes the government wants to encourage. Real estate has powerful tax benefits because the government wants private capital to solve the housing problem. The COVID-era 100% meals deduction existed because the government wanted to save the restaurant industry. Understanding the why behind any tax law unlocks the how.
"The tax code is just a roadmap. It's a set of incentives for investors and entrepreneurs to behave in the way the government wants us to behave."
3. Every Dollar Not Paid in Taxes Is Cash Flow Michael reframes tax savings not as avoidance but as cash flow — money that stays in the business and can be reinvested, compounded, or deployed into the next opportunity. The question is never "can I deduct this?" The question is "how can I legally, ethically, and morally deduct this?" That small shift in framing changes everything about how a business owner engages with their tax strategy.
"Every time you are not writing a check to the government — as long as it's being done in a legal and ethical way — see that money as cash flow that you can reinvest in your business."
4. Red Flag — All You Hear Is No One of the clearest warning signs that you have the wrong tax advisor is a relationship defined by what you cannot do. A great tax advisor leads with how — finding the legal pathway to the outcome the client wants, not reflexively shutting down ideas. The uniform example Michael uses — putting a company logo on clothing to convert it from personal to business expense — illustrates how a small creative step can change everything.
"Never come ask me if you can deduct something. Your question should be — how can I deduct this legally, ethically, and morally?"
5. You Need a Specialist, Not a Generalist Just as no one wants a general practitioner performing brain surgery, no sophisticated investor should be relying on a generalist CPA. The tax code contains enormous depth in specific industries — real estate, professional practices, technology — and advisors who have invested years in those areas bring a fundamentally different level of value. Finding the right fit means finding someone whose expertise mirrors how you make money.
"There's a reason the surgeon earns more than the GP. He or she has elevated their game to a specialized area. It's no different in accounting."
6. Meeting Your CPA Once a Year Is Playing a Losing Game The most common and costly mistake investors and entrepreneurs make is treating tax preparation as an annual event. By the time you sit down in March or April, the year is already over and nothing can be changed. A proactive tax relationship — quarterly at minimum — is what converts tax planning from a rearview mirror exercise into a forward-looking wealth strategy.
"If you're meeting with your CPA less than once a quarter, I think you have a major problem there if you're an investor."
7. Not Planning Your Taxes Costs You 13 to 18 Years of Your Work Life Michael delivers one of the episode's most striking frameworks — for a business owner in a 37% federal tax bracket who does no proactive planning, 37% of every hour worked goes to the government. Over a 60 to 65 year work life, that translates to 13 to 18 years of productive effort effectively donated to the IRS. Tax planning is not a luxury. It is the difference between reaching financial freedom early and spending decades running in place.
"You are going to be anywhere from 24 to 37% tax bracket just on the federal side. Over 60 or 65 years of work life, you're putting yourself into a tax jail of 13 to 18 years."
8. Your Tax Return Should Be a Validation — Not a Surprise Michael's firm does not accept clients who only want a tax return prepared. Every engagement is a 12-month coaching and consulting relationship. The tax return at the end of the year is simply the validation of the planning work done throughout. And his firm's promise to every prospect is clear — if they cannot identify a pathway to reducing taxes by at least three times their fee, they will not take the client.
"Your tax return is just only a validation of the 12 months of coaching you. If we do not see a roadmap to reduce your taxes by a minimum of three times our fee, we don't want you as a client."
Resources
Email: taxes@smithcpa.com
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