Weird Side Bets That Made Founders Millions

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Not every smart investment starts with a pitch deck or a business plan. Some of the best returns come from personal bets founders make with their own money. We pulled together five that actually paid off – big. From a $10K angel check that became $1.2M, to flipping a beach house for a $2M profit, and mining Bitcoin before it was cool.

Here’s what we talk about:

• The overlooked angel check that quietly turned into a seven-figure exit
• Flipping a beachfront property for millions (plus cash flow along the way)
• Mining Bitcoin in a basement – and finding millions on an old hard drive
• Geo-arbitrage: the founder who 3x’d his wealth just by moving to Colombia
• Buying small businesses instead of starting new ones
• Mobile home parks, domain names, and other unexpected wins
• Common patterns behind the biggest personal money wins

Cool Links:

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

Sponsors:

• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise

Chapters:

• (0:00) The $10K Bet That Became $1.2 Million
• (4:49) Beach House Windfalls & Real Estate Flexes
• (8:01) Triple Your Net Worth – Just by Moving?
• (10:25) Oops, I Mined a Million in Bitcoin
• (12:48) Crypto: When 3% Becomes 30%
• (14:48) Why Founders Buy Businesses Instead of Building
• (16:59) Three Wealth Rules Every Founder Follows
• (18:15) The Boring Stuff That Actually Works

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.