Shaan's Stripe Interview Fail

Shaan tells a story about bombing his interview at Stripe in 2012 when the company was still very early stage.

"I applied to Stripe in 2012 - it would have been my first real job after starting two companies. I had it made because the interviewer's mentor was one of my former advisors who had written a blog post about me, saying I had the highest bias for action of any entrepreneur he'd met. He made a warm intro and told them 'trust me, this guy's legit, you should hire this kid.'

During the interview, they wanted to do a sales role-play. The interviewer said 'pick any software you want to sell.' I picked Basecamp, which was a big mistake because I didn't know it very well. When he said 'hello, I just picked up the phone, go' - I completely froze.

By the end of the role-play, he was just straight up honest with me: 'I don't think this is for you.' They were probably at 50-100 people at the time. I definitely blew it - it wasn't their fault. I would have had to start in a lower position and work my way up to get equity, but given how successful Stripe became, that missed opportunity probably cost me millions."