One of my weirdest angel investments (a fortune cookie company), made me $300k in 4 years w/ a $25k investment.
Here's what happened...
I was friends with the founders.
Kinda thought the idea was meh (ads inside fortune cookies).
But I liked the guys, they'd won before with this product (ha) and I said I'd do it so I invested.
Very few updates from them, no real big wins or revenue hit.
I actually (sorry guys) wrote the investment off as a $0.
Turns out instead of tweeting or updating me they just had their heads down building a "boring" business into a nice lil 12xer for investors.
Then crypto hit, cannabis hit and a bunch of sectors (gambling, lottery) that couldn't do traditional advertising needed a solution.
So where'd they go? MFing fortune cookies.
Before I know it the guys are building a factory, getting bigger investors and raising again.
And they're crushing it.
What I learned in investing again and again.
#1 If you're going to gamble in startups... bet on the founders.
#2 Winners win, if they've swung and hit big before, pretty good chance on round two.
#3 Don't underestimate tailwinds.
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11 ways I still live cheaply so $ is never a worry...
Airbnb Even When You Don't Need To:
- for as long as I can remember, I've rented out my house (for at least some portion) on Airbnb
- now I do it for all my properties
Yes even my main house. (weird to say "main house" outload - rich ppl sh*t).
Always Ask for Discount:
I used to think it was cheap to ask for discounts almost constantly. I thought it made me look poor. Then I traveled with my partner at my PE fund and he did it nonstop.
His reason - "No one does it, so more often than not, you'll get one."