I joined his company as employee #8 in a (non-technical) role I wasn't qualified for, in an industry I didn't know existed, leveraging a technology I knew nothing about. I didn't have any accomplishments but a few failed startups, but he thought the hustle I demonstrated was all I needed to be successful in the role he was hiring for.
Fortunately he was right.
1. We scaled to 200 employees in 4 years bootstrapped.
2. I got to work on problems you only get access to 15 - 20 years into your career
3. Very cross functional role working on sales, biz dev, product, legal, support.
4. Raised a few rounds and got acquired for a lot of $.
5. The company was acquired 6 years after I left, but I had 10 year options that had less than 6 months left before the expiration date.
The company experienced a lot of growing pains around year 3/4 that caused me to leave (along with some mistakes I made along the way), but I only look back at the experience with fondness.
Absolutely incredible experience.