Noah is a third-generation CPA who has seen money from every angle. He testified in high-net-worth divorce cases, built and sold a family office for divorced women, syndicated close to a billion dollars of real estate, and now runs Wealthrive, a tax strategy firm for entrepreneurs doing seven figures of income or staring down an eight-figure exit.
Here are the parts worth your time.
The family that skipped the prenup on purpose
Noah's client married into a family whose name you would recognize. Hundreds of millions behind them. No prenup. She assumed that was good news.
It wasn't. The family had every asset wrapped in trusts before the marriage. The house she lived in was owned by a trust. The income funding her lifestyle came from a trust. When the divorce came, none of it counted. She expected tens of millions and walked with one or two.
And the missing prenup was the tell, not an oversight. A prenup requires financial disclosures. The family did not want to disclose. As Noah put it, the ultra wealthy own nothing and control everything.
Your accountant is not your strategist
This is the core of what Noah does now, and the frame is simple. Your tax preparer files history. A strategist plans the future. Most entrepreneurs find out what they owe when the draft return shows up in Q1, sometimes on income they never received in cash.
The gap gets expensive at exit. Noah says planning is worth at least 10% of the purchase price on most deals, often 15 to 30%. On the eight and nine-figure deals his firm works on, that's millions left on the table for skipping the conversation.
One example: a structure where a seller with a $20 million gain puts in $2 million and generates a $20 million paper loss in the same tax year. The money inside grows tax-free and comes out tax-free. In one recent deal, the seller kept equity and the ongoing dividends came out untaxed too.
What "risk" actually means
I pushed him on this, because aggressive structures make people nervous. His answer was more useful than the usual hand-waving.
About 15% of returns reporting $10 million or more of income get audited. Under half a million of reported income, it drops below 2%. Most of his clients report under a million because of the strategies themselves, so they sit in the 2% bucket.
Then he walked through the track record on that leveraged-loss structure. Twenty-five years in use, hundreds of returns, part of seven audits. Six closed with no change. The seventh lost in lower court, won on appeal, and the structure was amended so the contested issue no longer exists. That's the homework he wants everyone to do: how long has the strategy existed, how often has it been audited, and what does the case law say.
The decade that ended at zero
This is the part I respect Noah most for sharing. He spent 2011 to 2021 syndicating heavy value-add real estate with high leverage and variable-rate debt. Averaged a 27% IRR for a decade. Then rates doubled in a few months and the same model got crushed. Deals returning 40 cents on the dollar. Some at 20. Several at zero.
He lost tens of millions of dollars of money from people who trusted him, many of them friends. No spin on it. His takeaways were the ones that stick: he could have pulled back the throttle and didn't, because the model was all he knew and it still felt right. And the thing that saved his family was never betting the balance sheet on any single strategy.
His filter now is one question. Does this risk my family's financial security? New capital goes into his operating business and public markets. Nothing else. His reasoning echoes something I believe about hiring: a good hire in your own company produces a return almost nothing passive can match.
The advice for anyone still building
If you're earning half a million or more, Noah's take is you should have a tax strategist you talk to every year, separate from your preparer. Not a one-off trick like the Aspen short-term rental that works for exactly one season, but an actual multi-year plan that fits where your income and your exit are heading.
Give the full episode a listen. Noah is unusually candid for someone who has won and lost at this scale, and the divorce court stories alone are worth it.
— Sam Silverman
Silverman Capital
