How to know when to leave your startup
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Original post by Penelope Trunk via VB
My third startup is Brazen Careerist.
When I started building the brand of Brazen Careerist around the year 2000, I talked about ideas like job hopping as a way to build a solid career, and I warned that generation Y’s entry into the workforce would be a total shock to employers. I was labeled a heretic and a moron.
But pretty quickly, people started thinking I was right. And I started making $15,000 a speech to discuss these ideas.
The intoxication of being on a trend, and knowing how to monetize it and being excited about being right, that’s what makes someone do a startup. So I picked up two partners, I launched Brazen Careerist, and quickly, Mashable called us the number-one social networking site for Gen Y. We were on a roll.
We raised money. We launched products, we pivoted 20 times. We were due to raise more money right after the markets crashed. So of course we couldn’t raise money. And of course I did what all startup founders do when they run out of money: I had a shit fit. And then I had a nervous breakdown.
But the thing is, in a startup, everything moves at warp speed, even a nervous breakdown. So I recovered fast, convinced investors to put in more money. And we kept going.
That cycle happened twice. Which is normal. Because startups are hell, and a startup is the perfect convergence of a brilliant idea and a founder just crazy enough to stick with it through anything.
At that point, I was exhausted. And I had to figure out: When is it time for a founder to step down? So I went through a time of personal assessment, which taught me a lot about when you know it’s time for a founder to leave:
Financial exhaustion
I had funded the idea with my own money for a few years before I launched Brazen Careerist as a social recruiting platform. I ruined my credit, I cashed out my 401K (don’t ever do this!) and I lost a baby sitter because she was appalled that we didn’t have any food in the refrigerator.













