Family Office Podcast: Billionaire & Centimillionaire Interviews & Investor Club Insights

Hard Lessons: Pay Your Lawyers, Align Incentives & Why a $90M Exit Paid the Founder Only $2M | FOC

Private Investment Banker, Family Office CFO ($2B Portfolio), Serial Entrepreneur / AI Investor, Deep Tech Founder

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0:00 | 10:11

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The most candid segment of the panel. A private investment banker says the most expensive mistake he made was not paying for expert legal counsel — and explains why a cheap lawyer costs more on the back end than a good one does upfront. A family office CFO cites his first private investment loss to make a principle: founders must have skin in the game and LP capital must come back first, always — the Richest Man in Babylon principle applied to modern private investing. A serial entrepreneur says his most painful lesson was firing himself too late from his own company. And the banker closes with a real deal: a company that sold for $90 million where the founder walked away with $2 million — because of how capital was raised and what the terms looked like. Final note: if you're raising seed capital, your first check almost never comes from a stranger — it comes from your own network.

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