Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/

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/

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.

Weird Side Bets That Made Founders Millions

Moneywise