10+1 Lessons from Serial Entrepreneur Justin Kan

a16z General Partner Andrew Chen (@andrewchen) talks with serial entrepreneur and co-founder & CEO Justin Kan (@justinkan) about lessons he's learned as a founder. 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. Justin reflects on his journey and shares 10 + 1 lesson he’s learned along the way: - 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 now that he's not a first-time founder - What he’s reading and listening to - Bonus (+1): advice he’d give his 20-year old self just starting out in tech