Hey y’all — what would you have done with $20M at 20 years old (after selling your first startup)?

If your answer wasn’t “immediately go start another company with a bigger goal” then you’re not quite like Emil Barr.

Emil is essentially following the Elon approach. After Elon sold Zip2 in 1999 and made $22M from the sale, he used over half of that to start PayPal.

When you win big early, you’re time-rich too and can afford to double down on what’s next.

I sat down with Emil when we were both out in SF a few months ago during his fundraise for Flashpass (which hit $4M ARR in its first year and is on track to quadruple in its second). They ended up with an oversubscribed $4.25M seed round that I participated in.

He was candid about how the level of commitment required basically left with him with a very non-traditional college experience, and what made his Wall Street Journal op-ed go viral:

When I say front-loading success, what do I mean?

The traditional path in life is not going to lead to happiness. Work a 9-5 at slightly higher salaries over the years, get your 401(k) match, and then retire one day to do… what you really want to do.

Fewer people are buying into that today than ever before, but it’s still a dominant narrative.

Emil takes the opposite approach to the extreme. His perspective was that it wasn’t enough to be successful, he wanted to ensure he’d achieve success as young as possible.

Success is leverage. Capital is freedom (of time, movement, you name it).

Many founders wait years before starting their first company. They want the big company logo for credibility. They want the skills they’ll acquire there too.

But instead of planning to spend years until being ready to build a big business, Emil asked himself what it would require to achieve that right out of the gate.

Emil’s success is an outlier but it wasn’t an accident.

Here’s the currency he spent to achieve it:

That’s not standard, and he admits it was a brutal cost, but it led to things that he says were worth it:

While intense, Emil doesn’t think his approach is outlandish. He cites Elon, Kobe Bryant, and J.K. Rowling as examples of how outlier success comes from outlier levels of commitment.

Last fall, he published this op-ed in The Wall Street Journal about why work-life balance will keep you mediocre.

The piece hit a nerve and became one of their most talked about pieces of the year with over 2,100 comments on their site alone (I didn’t even know that many people still went to legacy media websites, but I digress…).

Even months later when it gets reshared on X it draws thousands of engagements.

Young, successful founders are not abnormal in Silicon Valley, but they’re considerably more rare in Ohio (where Emil is from and still lives, though he told me he’s buying a plane to make traveling back and forth easier).

It puts Emil in an interesting position.

On one side of his life, he sees the excitement around AI in the tech world (though also some anxiety about white-collar layoffs). And on the other side, he sees the skepticism around how it will impact various industries and the availability of jobs that’s common in much of the rest of the country.

It’s clear to him that tackling AI-driven employment concerns is going to be a major issue over the next 5+ years.

Flashpass builds software to power trade schools, which are going through a massive influx of interest right now. If AI takes the white-collar jobs, trade schools will likely supply a good chunk of the next wave of employment.

And if Flashpass is successful as a venture bet, Emil will have the leverage to do whatever he wants next. It’ll almost certainly be something even bigger.

Advertise in my newsletter to get in front of 70,000+ founders.