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Five founders. Five exits. All around $30 million. So why did one walk away with $30M – and another with just $2M? From taxes and co-founders to deal structure and equity rollovers, the factors that shape a founder's final payout are rarely simple. This episode is your crash course in what really happens when a deal closes.

Here’s what we talk about:

• How Eran Galperin took home ~$30M while still keeping ~50% of his company
• Why Scott Galloway only netted $2–3M from a $33M sale
• How Alex Hormozi earned more from distributions than the $31M exit itself
• The ultra-simple, debt-free deal that netted two Canadian brothers $20M each
• Marshall Haas’ $18M cash payout – and why he held onto equity for peace of mind
• Why the "headline number" often masks the founder’s true financial outcome
• The impact of seller notes, taxes, state residency, and post-sale roles
• What to consider before you sell to avoid regret or burnout
• The myth of the $1B exit – and how one founder only took home $70M

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

• (0:42) Five Exits, Five Wildly Different Payouts
• (1:37) Eran Galperin: The Gym Desk Power Play
• (4:19) Tax Dodges & Seller Notes: Cash Isn’t Always King
• (5:22) Scott Galloway: $33M Headline, $3M Reality Check
• (7:39) Alex Hormozi: Gym Launch – Cash Out, Cash In
• (8:32) The Sinkinson Brothers: Double or Nothing in Canada
• (11:56) Marshall Haass: The Art of the Partial Exit
• (13:17) Why Smart Founders Never Sell It All
• (15:28) Scoreboard Envy: Don’t Get Played

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.