Retire from just ONE investment? This is how he did it…

By Matthew Milner, on Wednesday, August 30, 2023

Last Friday, before I took off for the weekend, my friend Aitio dropped by the office.

He stops by a few times a year just to say hello.

He wasn’t exactly in our neighborhood, which is in downtown Manhattan on the water. But with his 2023 Tesla Model S Plaid (0-60 MPH in 2 seconds), he doesn’t mind traveling.

Aitio used to be a general contractor in Queens and he made a good living. So he started putting some money to work in bars and clubs. But in 2007, he decided to invest in tech startups instead.

He had some small wins over the years as an angel investor. A single here and a double there.

But a few years ago, he hit a homerun.

Now he’ll never have to work again.

A Simple But Brilliant Investment Philosophy

When we started Crowdability back in 2014, we asked Aitio to describe his investment philosophy — and we’ll never forget his reaction:

He paused to think, stroked his well-groomed goatee, then broke into a smile.

“All it takes is one,” he said.

And that’s where he got his nickname:

A.I.T.I.O: All It Takes Is One.

Average vs. Above Average

To decipher Aitio’s philosophy, let’s review the numbers behind startup investing.

According to Cambridge Analytics (an advisor to institutions like The Rockefeller Foundation and Harvard University), investing in startups has returned an average of 55% per year over 25 years.

That’s enough to double your money every couple of years or so.

But remember, that’s just the average. Plenty of folks — people we know and work with — have done far better than average.

For example, consider our business partner Howard Lindzon. Howard’s annual returns have been measured in the "hundreds of percent."

What’s the secret to earning triple-digit annual returns?

Let Aitio give you a hint:

All it takes is one.

You’ve Seen the Evidence

Long-time Crowdability readers will recognize our familiar stories about investors who’ve hit it big on a single investment.

Howard’s investment in Uber, for example…

For every $5,000 he invested, he got back $2 million a few years later. That’s 400 times his money.

Then there’s Paul Graham, another startup investor. On his investment in a web service called Heroku, he earned 491 times his money.

And when he invested in Twitch, a video-game company, he earned an estimated 573 times his money.

All It Takes Is One

And here’s the thing:

Even if you make dozens of startup investments and all of them go to zero — well, all of them except one

You could still make a fortune.

Because all it takes is one.

Enough to Retire

Let’s say you invest in 50 startups over the next few years.

You put $1,000 into each one, for a total investment of $50,000.

Based on the historical odds, it’s likely you’ll get a handful of “base hits” — enough hits to get you to the 55% annual returns we mentioned earlier.

But even if 49 of the companies go belly up — in other words, even if your first 49 investments literally go to zero…

As long as the 50th company turns out to be “an Uber” — the investment where Howard made 400 times in money — your $1,000 investment would be worth $400,000.

So your $50,000 startup portfolio would turn into $400,000.

That’s a 700% net return.

And what if you’d invested $5,000 into each startup instead?

Your stake would be worth $2 million.

For most folks, that’s enough money to retire.

And that is what’s so exciting about startup investing:

All it takes is one investment to change your life.

Happy Investing.

Best Regards,



If you enjoyed this article, subscribe to updates:

Sign-up today and you'll receive our daily insights on early-stage investing, as well as our FREE "Equity Crowdfunding Action Kit" – where you'll learn:

  • The Ins & Outs of Equity Crowdfunding
  • A step-by-step path to get started
  • Tips from dozens of Venture Capitalists
subscribe to updates

Thank you for subscribing!

Tags: All it-takes-is-one Average

Share This:
comments powered by Disqus