Justin Kan & Brian Chesky: The Rejections That Built Twitch and Airbnb | E2344
This Week in Startups
September 30, 2026
This Week In Startups is made possible by: Today’s show: Seven investors passed on buying 10% of Airbnb for $150,000, a stake pegged at roughly $9.25 billion today.
Speakers Lon Harris, Alex Wilhelm, Jason Calacanis, Justin Kan, Steven Estes, Brian Chesky
TopicsTechnology
Lon Harris (0:00)
Hey, everybody, welcome back to This Week in Startups. I am Lon Harris, with me not as always, on a special occasion, former co-host Alex Wilhelm. Thanks for being here.
Alex Wilhelm (0:09)
Oh, it's so good to come back. Friendly faces, I'm sweating in a blazer again. You know, just like old, that's my friend.
SPEAKER_3 (0:15)
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Lon Harris (1:01)
And much like all times, you will notice I am wearing my plaud pin. It is right here, pinned to my jacket, recording everything that everyone says, and then it will conveniently download it, a summary, a transcript, meeting notes, whatever I want, all organized. I don't have to do a thing, I just have to use, hit the button, tell everybody that they're being recorded, so you don't do it surreptitiously, and then it's all going to just be done and waiting for me when I am done with the show or the call. If your work depends on conversations, interviews, meetings, anything like that, we urge you to get a note pin for yourself. You can check it out. Find out more at plaud.ai/twist, and be sure to use the code TWIST to get 10% off your order.
Thanks to our friends at Plaud, we applaud Plaud.
Alex Wilhelm (1:45)
We do indeed applaud Plaud. The first good AI wearable is how I think about Plaud, they cracked it. They actually got something together that people need to use and makes their life better, and the first couple of pendants just didn't hit the mark, so shout out to Plaud for being early.
Lon Harris (1:57)
Yeah, that AI pin, those people are like, why are we taking strays? Why do we have to take strays on the Plaud ad read?
Alex Wilhelm (2:04)
I had to watch their launch video, Lon, that's why they're taking strays. They took five minutes of my life and I'm mad about it.
Lon Harris (2:10)
Yeah, it's like, I don't know, it's just like that, a pin is a weird form function, I think we can all agree.
Alex Wilhelm (2:16)
Well, anyways.
Lon Harris (2:17)
The AI brooch.
SPEAKER_4 (2:17)
What are we here today to do?
Alex Wilhelm (2:18)
What are we doing?
Lon Harris (2:19)
We're not here today to just talk about AI brooches. We're here today, we're doing another of our patented flashback episodes. We're going to look back at an episode of Twist from February 2019 Folks, this is episode 900, a landmark show, and it features Justin Kan as Jason's guest of Justin TV, later to be known as Twitch, the guy who once strapped a camera to his head and live streamed his entire life around the clock. That 2007 stunt, Justin TV, soon opened up to anyone who wanted to broadcast and live stream their lives, and its gaming section later spun off as Twitch, which Amazon, of course, bought in 2014 for 970 million, and you could currently still use if you want to catch up on the hottest video games or get very, very angry about politics. By the time of this chat, Justin had moved on to Atrium, that's a legal tech startup that had just raised $65 million in their Series B.
Atrium would shut down barely a year later, and Justin has since gone back to gaming. He had the NFT Marketplace fractal, and now he's doing Stash, a web shop and payments platform for mobile game developers. So let's go back to 2019 Alex, take a little trip into history and check out some of these classic clips featuring Justin Kan.
Alex Wilhelm (3:36)
Absolutely. Now, I have a number of things that I want to get too long, but where are we going to start in this relatively long and I would say luxurious interview?
Lon Harris (3:43)
Yeah, I'd like to jump. My first clip is at about five and a half minutes in, and they are talking about Justin and Jason both when they first discovered that people on the internet wanted to watch other people on the internet play video games. Let's take a look at this startling revelation.
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