This Is What Startup Burnout Looks Like

Watch out. The emptiness will sneak right up on you.

Joe Procopio
5 min readSep 8, 2022


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A few weeks ago, I was at a startup investor event — my first time getting back out into the local scene in ages — when I was introduced to a founder I’ll call “Brian,” by an investor friend of mine who had invested in the seed round of Brian’s company.

That investment was eight years ago. The company was doing well, better than well actually, and the investor was all smiles, but Brian was visibly uncomfortable. See, the two of them had been having a discussion about the future, and Brian wasn’t happy.

The investor, an older guy who has seen it all before, was nodding in knowing empathy. And since I had just strolled up, the investor decided I was the perfect person for Brian to talk to about powering through the inevitable entrepreneur burnout.

In retrospect, I probably shouldn’t have said what I said. But at least it was the truth.

The Reckoning

My own personal startup burnout reckoning moment happened as I began my initial descent into Austin, where I’d be giving a talk at SXSW in less than 24 hours about the technology our startup had pioneered on its way to being acquired by a private equity firm two years prior.

The CEO of our startup, my partner over the seven-year journey, had left the company three months earlier. Now, the minor “differences in strategy” between us and the acquirers — the kind that accompany any acquisition — were about to erupt into a schism, leaving me alone against the multi-billion-dollar PE firm.

It had stopped being fun a while ago, and now it was about the future, and how much of a role I wanted to play in it. I had been perfectly content to continue fighting the good fight when my flight to Austin had taken off some four hours earlier. By the time we touched down, I knew I was done.

And I still had a talk to give.

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Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at

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