a16z Podcast

a16z Podcast: 10+1 Lessons from a Serial Entrepreneur

Justin Kan and Andrew Chen

Posted June 10, 2019

Want actionable advice from a founder who has built multiple tech companies and has invested the time to be open, introspective, and transparent about lessons learned?

In this episode (which originally aired as a YouTube video), a16z General Partner Andrew Chen talks with Justin Kan. Justin is a repeat entrepreneur who co-founded Kiko Software (a Web 2.0 calendar that pre-dated Google Calendar by 4 years); Justin.tv (a lifecasting platform); Twitch.tv (a live streaming platform for esports, music, and other creatives now part of Amazon); Socialcam; and now Atrium, a software-powered law firm for startups.

In this conversation, Justin ruminates on:

  • The paradox of choice: choosing a focus
  • Tradeoffs between B2B versus B2C companies
  • Market risk vs execution risk
  • Fundraising strategy: go big or stay lean?
  • Managing the stress of being a startup CEO (again!)
  • Seeking out mentors, coaches, and peers for help
  • Intentionally designing a culture to avoid the pitfalls of “culture eating strategy”
  • Things he’s still doing in his latest startup — and things he’s doing very differently
  • Managing higher expectations
  • What he’s reading and listening to
  • Bonus: advice he’d give his 20-year old self