a16z Podcast: 10+1 Lessons from Serial Entrepreneur Justin Kan
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 (@@andrewchen) talks with Justin Kan (@justinkan). 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 lessons he’s learned:
- 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
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In this episode
- 01:04 - How did Justin Kan rise to fame?
- 06:01 - Why would you leave a cushy job as a partner at Y Combinator and start another company?
- 08:42 - What is the difference between Market Risk vs Execution Risk?
- 11:04 - Should I start a consumer startup or a business-to-business startup?
- 13:55 - Should you raise a lot of money or bootstrap to profitability?
- 19:29 - How do you deal with stress as a startup founder?
- 24:22 - What influences Justin Kan's social media stream?
- 24:45 - Why is Justin Kan removing attachments form his life?
- 27:16 - What is the best way to find a mentor for my startup?
- 31:05 - What is the meaning of Culture eat Strategy?
- 36:33 - What is the central ethos to how Justin Kan builds companies?
- 38:58 - How do you manage expectations once you've succeeded as entrepreneur?
- 43:12 - What is Justin Kan reading right now?
- 46:39 - What is one advice you would give to an entrepreneur who is just getting started?
Smash Notes summary for this episode
How did Justin Kan rise to fame?
Justin has been an Internet entrepreneur since 2005.
He first founded a company called Kiko, which was a version of Google Calendar but unfortunately came out a month before Google Calendar and got completely crushed.
After that he started a live TV show on the internet, called Justin.Tv. It was 2007, before the iPhone, so Justin had to carry a computer in the backpack, with multiple cellphone connections, live-streaming a hacky video feed to people at home. He admits to not had been very popular at the time, with only hundreds of viewers at first. Eventually however, other people caught wind and wanted to create their own shows, just like Justin's. Justin.tv raised a bunch of money, just in time to survive the "nuclear winter" when most video startups died.
While still working on Justin.tv, Justin and Co create an app called "Social Cam", which they were able to promptly sell to Autodesk for many millions.
Finally, after years of hard work in the video space, Justin's co-founder Emmet though up the idea for Twitch, which exploded and sold to almost $1 Billion dollars!
After the acquisition Justin played around with other startups, namely Exec, a home cleaning on-demand, and Whale, a social app for Q&A.
Finally, two years ago he decided to put all his eggs in one basket and stated Atrium, a technology enabled law company for entrepreneurs.
Why would you leave a cushy job as a partner at Y Combinator and start another company?
After a few years as an investor and advisor to Y Combinator companies, Justin realized he was not learning and growing anymore, and the best vehicle for growth that he knew was a startup. Given that Twitch.tv had a pretty big outcome, Justin needed to do something even bigger in order to attain the learning opportunity he desired. Atrium was the answer.
What is the difference between Market Risk vs Execution Risk?
When you are a young founder, fresh out of college, chances are you don't know a lot and you are not actually very good at many things. At his point, it makes a lot of sense to pick a consumer startup that has a lot of market risk (nobody wants your product) but low execution risk (you fail to deliver correctly). If you can find something that users love, your chances of winning big are quite high. Thinks Snapchat.
Once you mature and gain skills, it might make sense to work on a startup with less market risk and more execution risk, a startup that you know people already want, but it's very hard to deliver correctly.
Justin Kan had played with a few consumer startups post Twitch, and he'd found it really hard to find product-market fit. With Atrium however, he knew that legal market was already huge, and it was also ripe for innovation. With everything he learned from 15 years of startups, it seemed the best fit.
Should I start a consumer startup or a business-to-business startup?
Consumer startups are a lottery ticket. Take Twitch.tv vs Atrium for example.
In the case with Twitch, nobody believed there was a market in streaming video over the internet. Even as founders they were skeptical there was business. On the bright side, there was also no competition because nobody believed it was worth competing. Justin and Co got all the time to figure our their product market fit, even with all the mistakes they'd made along the way.
Atrium, on the other hand, is a business that requires a structured and a measured approach. Now that Justin knows how to raise capital and to put together a team ...etc, he's got an upper hand when compared to Justin at 22, winging it along the way. Consumer startups are like a lottery ticket, which is why most mature entrepreneurs prefer to play the b2b game.
Should you raise a lot of money or bootstrap to profitability?
When you have a ton of money, you spend a ton of money, so that's not always the right choice for your company. In the execution risk business it is however important to deliver value fast and to assure the clients that the company would be around for a long time. Given the nature of Atrium business, it was also beneficial to have a lot of venture capitalists on board, since all of them needed legal help for their companies, Atrium was set to become the company of choice.
How do you deal with stress as a startup founder?
Young Justin though of stress was something that you couldn't change, but a manure Justin learned that you can manage and improve stress, much like you learn to improve everything else about your life. He started writing a gratitude journal, switched to Ketogenic Diet to gain more energy in the day, and started to meditate.
What influences Justin Kan's social media stream?
Justin believes that if you want something to be part of your identity, you should talk about it, and if you want to learn something, you should teach it. That's why his latest tweeter feed is all about philosophy and startups.
Why is Justin Kan removing attachments form his life?
Founders tend to intertwine their identity and the success of their company. Yet, if you rely on the outside factors to make you happy, you are always going to be disappointed. Here's Justin explaining this concept on Below the Line.
What is the best way to find a mentor for my startup?
Best part about Silicon Valley is all the people who have done it before and are willing to help you. Whether you are a new entrepreneur or a seasoned one, there's always someone who has made it further than you, and despite their success they are willing to help you. The system works because once you've gotten help, and succeeded, you pay it forward by doing the same for new founders.
What is the meaning of Culture eat Strategy?
Very often companies in Silicon Valley tend to focus on the next milestone, and sometimes it's the only way because otherwise your company would go out of business. However, if you can build a company that runs on a common set of principles, where the team is enabled to make decisions on their own and everyone feels in control, the execution will follow. To succeed in the long run, it is imperative to build a company that can execute, and culture is the driving factor.
What is the central ethos to how Justin Kan builds companies?
(1) Iterate quickly. Justin has been doing this since Y Combinator and never stopped. Speed of iteration is very important. (2) Be helpful and build a community that helps each other.
How do you manage expectations once you've succeeded as entrepreneur?
Every entrepreneur has high expectations and it's always a battle against yourself. You win that battle by realizing that whatever happens you will be fine. Startups are not springs, but marathons; you have to figure out a way to be okay with that, or you will give up. Most people do not actually successfully internalize this.
What is Justin Kan reading right now?
The Untethered Soul - Very important book that helped Justin recognize why detaching happiness from the company success was so important.
Leadership and Self-Deception - There are two ways to treat other people: like people (with empathy), or like an objects (without empathy). If you treat people like objects who are there to achieve metrics, you will end up lying to yourself about your own role in their successes and failures and ignoring your own contributions, which is just poor management.