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

Ego Kills Deals — Plus 3 Secrets Nobody Talks About: PPLI, Board Seats & Cap Table Disasters | FOC

Second Gen Family Office (Security / Drone Tech), First Gen Family Office (Wellness / Health Tech), PE Managing Partner / Family Office, Audience Participants (Software Investor, M&A Executive)

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0:00 | 8:07

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Four insights in one episode, each from a different voice. A second-gen family office investor says ego is the single biggest destroyer of wealth — it makes you miss small details, over-rely on past success, and walk into deals you should have walked away from. An audience member introduces private placement life insurance — a custom IRS-compliant policy structure that lets your family office hold alternative assets in a tax-deferred environment. A software investor explains why poor board governance is the number one reason deals go sideways, and why preferred shareholders need a board seat to protect themselves. And a former IBM M&A executive warns on cap tables: a company he backed went from a $1.4M valuation to $350M — and investors were still only 4x up because of how the cap table was structured from day one.

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