Why You Should or Should Not Work at a Startup

Kan says startup management is often poor, and early employees may need to ask actively for mentorship and direction. Startup equity rarely makes employees rich, and startups usually cannot promise stability or a five-year career plan. He suggests people seeking those things consider a larger company.

Kan says startups can offer jobs people would not yet qualify for elsewhere. He recalls hiring Jim, a programmer from France, who soon ran the Rails back end for Justin.tv, then a top 100 site. Jim later co-founded Socialcam, which grew to 128 million users in two months, and became a co-founder of Triplebyte.

Kan describes startups as a way to meet people who share the work and ambitions you want to pursue. Finbarr joined Kan’s company Exec hoping to learn about startups and eventually start one. After an unsuccessful venture and a stint in YC, he founded Shogun, which Kan said was doing well.

Kan shares how Kyle Vogt learned to build scalable systems at Justin.tv, despite frequent outages at first. By Twitch’s 2014 sale to Amazon, the live video system transferred 90 petabytes monthly and was the fourth-largest bandwidth consumer in North America. Kan also describes how Daniel learned deal negotiation while selling the struggling Exec, then applied those lessons at Cruise, which sold to GM for over $1 billion.

Kan recommends choosing positions that maximize personal growth and learning, whether at a startup or elsewhere. He frames progress in terms of the rate of improvement rather than where someone starts.