Weird Side Bets That Made Founders Millions

Building and selling a company can mint millions, but our founders have also hit it big with unexpected side bets, like a ten thousand dollar check that later became more than a million or a first million made before the main business.

This is Moneywise for already‑successful founders; I’m Jackie Lamport, a little sick but still your sometimes host, and today we’re skipping the sleepy index funds to dig into the fun, riskier plays that actually paid off.

My first angel check went into Away’s friends‑and‑family round; I scraped together about ten thousand dollars even though I wasn’t accredited, my mom questioned it, and years later I was bought out for a huge return.

I know that was lucky, so now I treat angel investing like a small personal fund across roughly twenty‑five companies where I back founders first, diversify, and help them get to outcomes; three have returned money, two are zeros, and the rest are still in play.

Angel checks can take ages, can go to zero, and can feel dull if you only wire money, but it’s a blast if you care about the founders and want to help.

Around five percent of my net worth goes into active angel bets, and the fun is jumping on late‑night calls to actually help teams work through real problems.

If you want to play, cap the slice of your portfolio and keep it sacred, and treat it like fun money you can afford to lose.

Stick to sectors and founders you truly understand, and check our Oren Hoffman episode if you want to go deep.

I took nine million off a deal, bought a place in the Dominican Republic for about three point six million, rented it, and eighteen months later sold it to Albert Pujols for five point six million.

Beyond that I’ve built roughly twenty‑two million in real estate, including our Miami primary, a New York place, homes for family, and a presale Sunny Isles condo I plan to flip before the larger payment comes due.

Real estate can preserve wealth and throw off cash, though it’s illiquid and still needs attention when tenants churn or things break.

Another lever isn’t an investment at all: moving to a lower‑cost city to stretch runway, like Rob Hoffman leaving suburban Canada for Medellín so his dollar income went much further while he kept earning power.

He once stretched ten thousand Canadian for a full year in a rough apartment at about fifty dollars in rent, learned the language, rooted himself in the community, and used the gap to fund safer bets; for remote founders this can pull your lifestyle and finances forward by years.

Back in 2013 I was mining Bitcoin from libertarian forums, forgot about it, and later found the wallets by cataloging hundreds of old hard drives, which is how I made my first million.

You can’t rerun that exact play, and most founders we hear from keep crypto small or admit it’s a gamble; the ones who feel good about it usually took profits.

I put a few percent in crypto and it swelled to about thirty percent as prices spiked, so I’ve been trimming because that’s too much volatility.

Another winning move is buying businesses, which can become a whole strategy on its own.

I copied Buffett by acquiring simple, profitable tech companies and holding them; by 2021 we had tens of millions in profit and even took one public, and suddenly the value showed up in my brokerage.

We bought a three‑million‑revenue demolition company in Iowa, added environmental services and a real balance sheet, and it grew to twenty‑four million organically in three years.

If you buy, stick to what you know, look for simple profitable operations with clear customers and margins, have a plan before you wire the money, and treat it like an active bet, not a passive one.

Across all these plays, the common threads are right‑sized bets, leaning on your existing skills, and layering the spicy stuff on top of a safe core of index funds and ETFs.

Show notes have the deep dives on each portfolio; I’m Jackie Lamport, this is Moneywise, and I’ll see you next time.