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

More About This Podcast

The a16z Podcast discusses the most important ideas within technology with the people building it. Each episode aims to put listeners ahead of the curve, covering topics like AI, energy, genomics, space, and more.

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