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Founder Wealth Decisions

Bill Hammer 3 Episodes Oct 14, 2026

Founder Wealth Decisions is a podcast for founders with substantial wealth at stake. Each short episode presents a real-world case from the field, covering what a founder did with their business, taxes, and balance sheet, the choice they made, and what might have been done differently. Listeners hear anonymous stories about exit timing, defining "enough," liquidity, and family tradeoffs, with practical ways to apply each lesson before their own deal. It offers calm, evidence-based guidance for major financial decisions. New episodes are released weekly and run 5–15 minutes.

Episodes

You Might Have Solved Your Money Problem Years Ago Oct 14, 2026 397 A founder was selling his company and expected to walk away with roughly $10 million after taxes, but still worried about falling short of his family's $12 million goal. With a three-year earnout and a new contract that more than covered his lifestyle, the question wasn't necessarily how to earn another $2 million, but whether the money he'd already built could be enough. It's

Your Portfolio Has One Job After You Sell Oct 7, 2026 373 Thomas and Denise had built a life they loved, supported in part by a $3 million portfolio providing about $120,000 a year. As Thomas entered his sixties with markets near all-time highs, he wondered whether moving more of the portfolio into bonds would give them greater protection. Instead of focusing on percentages, we helped him look at what the portfolio was actually supposed to do—and whether

You Have a Financial Advisor. But Who Owns This Job? Sep 30, 2026 278 Scott built a $40 million business and had financial advisors he liked and trusted, but no one was responsible for making sure all the pieces of his financial life worked together. His investments didn’t reflect his life as a business owner, years of tax-planning opportunities had been missed, and $500,000 of life insurance replaced only about one year of his after-tax income. The issue wasn’t tha

The $40 Million Question We Almost Asked Too Late Sep 23, 2026 334 Jim thought a liquidity event was still three or four years away—until he learned a roughly $40 million payday could happen the following year, creating about $30 million in capital gains. Instead of assuming the tax bill was unavoidable, he spent $10,000–$15,000 to find out whether an out-of-state trust strategy could work while there was still time to put it in place. That planning ultimately sa

Why Successful Founders Say Yes to Too Many Deals Sep 16, 2026 311 A founder started the year expecting $50–70 million from three business exits. A few months later, two deals were dead, the third might return $5–7 million, and he could be facing another $5 million capital call—right as a great new opportunity showed up. Despite being worth tens of millions, he was suddenly asking whether he could write another check without putting himself in a cash crunch. The

The Founder Brain That Built Your Wealth Can Destroy It Sep 9, 2026 274 Adam sold his company in his early 30s and walked away with about $12 million after taxes. Ten years later, most of that freedom was gone—not from reckless spending, but from continuing to put his money into private deals, real estate, and other opportunities. The problem wasn’t taking risks; it was never separating the money meant to protect his family’s freedom from the money he could afford to

He Owned an $8M Business. And Had Less Than $100K in the Bank. Sep 3, 2026 216 Mike owned 70% of an $8 million business, but with less than $100,000 in the bank, a $15,000 monthly mortgage, and 90%+ of his net worth tied to the company, his family still felt financially exposed.Before an exit was even real, Mike and Lisa determined that $11 million after tax would make work optional. When the business sold for $36 million, the roughly $12 million first bite was enough—even i

A 26x Offer Came Years Early. He Was Ready. Sep 3, 2026 323 Tom owned a successful veterinary practice and thought he needed another 15 years to reach his $20 million goal. Then a 26x EBITDA offer put a $27 million exit in front of him—potentially giving him his freedom 13 years earlier than planned. The real decision wasn’t whether the offer was attractive. It was whether he already had enough to sell, spend more time with his family, and never regret wal

Founder Wealth Decisions

Episodes

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