Weird Side Bets That Made Founders Millions

Moneywise

Hampton

Business, Investing, Entrepreneurship

4.7 • 701 Ratings

🗓️ 16 December 2025

⏱️ 19 minutes

🔗️ Recording | iTunes | RSS

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Summary

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/

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.

Transcript

Click on a timestamp to play from that location

0:00.0	The number one thing I hear from founders isn't AI, it's hiring. A players are rare and expensive.
0:07.3	That's why smart founders and CEOs are using NEA to hire top-tier offshore talent in Latin America.
0:13.3	Over 700 companies like Function Health, Expensify and Deal, use NEA to build their teams and save hundreds of thousands in overhead. From senior
0:22.1	engineers to heads of accounting, to growth marketers, if it can be done remotely, NIA can find
0:27.4	you the right person. You'll save up to 70% compared to US hires. But the real win is the quality.
0:34.2	These aren't freelancers, they're loyal, long-term team members who actually care about your business.
0:39.7	NIR moves fast. You'll get resumes in three days and fill most roles in under three weeks, and you don't pay a dime until you make a hire.
0:47.5	One of Nia's founders is a Hampton member, and plenty of others already use them. So if you're ready to hire, the best talent in Latin America, go to hire with nea.com slash moneywise. That's hire with n-e-a-r.com slash money-wise
1:01.2	to get 5% off your first hire.
1:09.6	Building a business and selling it for tens of millions of dollars is one way to make a lot of money.
1:13.8	But it's not the only way. And our founders have actually made some good money on the side as well,
1:18.6	which is what this list is about. Like somebody who wrote a $10,000 seemingly forget a check,
1:24.0	and it turned into $1.2 million, A guy who was currently worth about $100 million,
1:28.6	but actually made his first million from his basement before he'd actually even started his
1:32.2	business. And another guy who 3xed his wealth overnight without actually investing in anything.
1:38.1	And this list isn't going to be about the safe stuff like index funds and bonds, which I know
1:41.3	Sampartouts a lot because, I mean, it should be an important part of your investment strategy. This is the more fun stuff, the riskier stuff that have actually paid off for a lot of our founders with specific examples. This is Money Wise, a show for founders who have already seen some success and are in the stage of figuring out what to do with it. And I'm Jackie Lamport, the producer and
2:00.9	sometimes host, who happens to have stumped a lot of you in the comments when it comes to my
2:04.6	age and gender, which it's very funny to me, so keep guessing. Also, I'm a little bit sick,
2:10.1	but we'll go on. So let's do that. Let's go on.
2:19.2	We'll start with one of my favorites.
2:20.9	The best $10,000 Jacqueline Johnson has ever spent.
	...

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