This Week in Startups · Sep 30, 2026 · 1h 18m · 60m saved
With Justin Kan, Co-founder of Justin.tv and Twitch · Brian Chesky, Co-founder and CEO of Airbnb
In 2008 Airbnb's founders tried to raise $150,000 at a $1.5 million valuation from 10 to 20 angel investors. Most of them did not reply. The hosts worked out that the same 10% stake would be worth $9.25 billion today.
One of the hosts said startups in the AI era are going from nothing to $100 million of revenue in record time. Justin.tv, the company that became Twitch, was five years old with about 25 people and was not growing fast when Google told it the team was not good enough to buy.
"Your team's not good enough. Goodbye."
Justin Kan, co-founder of Justin.tv and Twitch, and Brian Chesky, co-founder and chief executive of Airbnb, appear in archive clips from their This Week in Startups interviews of 2019 and 2023. The show's hosts replay the clips and argue about what has changed for founders since.
The full episode is covered here so you can skip it. 78 minutes of audio, 18 minutes of reading.
Here are the 12 moments that matter.
Key Takeaways
Google interviewed Justin.tv's entire team around 2010, then declined to buy the company because it judged the team not good enough
Twitch came from a bet on 3% of Justin.tv's content, made while the company had stopped growing
Seven investors passed on 10% of Airbnb for $150,000, a stake the hosts put at $9.25 billion today
One told the founders they loved everything "but you and your idea"
Airbnb got into Y Combinator by selling $4 cereal boxes for $40
Chesky said in 2023 that AI would turn search into matching and make proof of identity more valuable
The hosts said AI startups must charge sooner than Web 2.0 companies did, because every user now costs compute
AI has made their own jobs busier, not smaller, the hosts said, though a show task now takes about 20% less work
Chesky's prediction of "millions of startups" has come true mostly for people who already start companies, one host said
1. A Flashback to Episode 900
The episode replays This Week in Startups episode 900, from February 2019, in which Justin Kan was Jason Calacanis's guest.
A host recounted the history. In 2007 Kan strapped a camera to his head and streamed his life around the clock. The site, Justin.tv, soon opened to anyone who wanted to broadcast, and its gaming section was spun off as Twitch, which Amazon bought in 2014 for 970 million.
By the time of the 2019 interview Kan had moved on to Atrium, a legal technology startup that had just raised a $65 million Series B. Atrium shut down barely a year later. Kan went back to gaming, first with the NFT marketplace Fractal and now with Stash, a web shop and payments platform for mobile game developers.
