In short
Justin Kan’s origin story from Yale/Y Combinator (2005) through building JustinTV, pivoting to Twitch, and later starting other companies; includes lessons about launching early, product-market focus, and why services often don’t scale.
Guest backgrounds
Justin Kan is Twitch’s cofounder (originally JustinTV), a YC founder from the first 2005 batch. Interviewers are Carolyn and another host (longtime YC/tech peers; Carolyn references Justin’s early YC era and later content like Snapchat/YouTube).
Key claims
YC’s weekly progress + demo-day format shaped how he built; early streaming proved people want to follow others; Google Calendar’s launch showed incumbents could out-execute; Twitch emerged when gaming became the dominant category; services (e.g., Exec, house cleaning) struggle with scaling, margins, and edge cases.
Notable examples
2005 YC calendar demo (drag/drop appointments); Yahoo’s acquisition offer for the calendar company that later ghosted; selling the calendar startup on eBay for $258,100; JustinTV’s 2006 swatting incident at Crystal Towers; JustinTV’s pivot to a creator streaming platform (Oct 2007) and then gaming → Twitch; Twitch sold to Amazon in 2014 (Justin left before acquisition).
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOJustin's Journey to Y Combinator
0:45 to 2:58
Justin shares his early experiences with startup ideas and applying to Y Combinator.
“other for 20 years because i remember coming into this industry and like hearing people be like oh I've known that guy for 15, 20 years.”
The Interview Experience
2:58 to 5:15
Justin recounts his interview with Y Combinator and the challenges they faced.
“That's why he was excited to apply, you know, because he'd heard of Paul and I hadn't really been into CS before.”
Living Conditions and Development
5:15 to 7:20
Discussing their living conditions during the Y Combinator summer and their early development days.
“The interviews were 40 minutes at the time.”
Memories from the Y Combinator Batch
7:20 to 10:04
Reflecting on the startup culture and experiences during the early days of Y Combinator.
“But we were just basically in this apartment all summer, you know, hacking on the, like, there's no air conditioning.”
Demo Day and Initial Funding
10:04 to 12:22
Justin shares his experience at the first demo day and their initial funding journey.
“Do you remember there were like 12 people in the audience?”
Life After Y Combinator
12:22 to 14:00
Discussing the impact of Y Combinator on Justin's career and working out of the office.
“If we were smarter, we probably could have made that company work better.”
A Shocking Door Incident
14:00 to 15:56
Justin shares a humorous story about an unlocked door incident at a friend's house.
“Just to be clear, unlocked open or hanging open?”
Lessons from Y Combinator
15:56 to 21:00
Justin reflects on his time at Y Combinator, discussing the highs and lows of startup life.
“But I first want to ask you, do you remember when Google Calendar launched?”
The Decision to Sell on eBay
21:00 to 24:16
Justin recounts the decision-making process that led to selling their startup on eBay.
“We built like a family social network that was kind of like a genie or something like that.”
The Birth of Justin TV
24:16 to 28:05
Justin describes the inception of Justin TV, including the challenges and inspirations behind the idea.
“Cause he was actually, Paul was also super encouraging.”
Show all 24 chapters
Startup Adventures and Security Incidents
28:05 to 32:48
Justin Kan shares intense experiences from the early days of Justin TV, including security threats and swatting incidents.
“And Michael Seibel and I were like, no, please, please trust us when we say this is a prank.”
The Evolution of Streaming
32:48 to 34:04
The transition from Justin TV to Twitch and the insights gained about streaming content.
“Like there was, I didn't even know what a swatting was until like, you know, this was like early internet, right?”
Starting Exec and Lessons Learned
34:04 to 40:14
Justin discusses his venture Exec, its challenges, and the lessons in service scalability.
“And were there like, there were like early influencers before influencer was a word.”
Reflections on Entrepreneurship
40:14 to 42:07
Justin reflects on his numerous startups, emphasizing the key lessons learned throughout his journey.
“We ended up pivoting to house cleaning of all things, but like, it turns out people wanted certain categories of things.”
The Evolution of Silicon Valley Startups
42:07 to 43:16
Discussing the shift in startup focus from technology to services in Silicon Valley.
“There was first a bunch of like Web 2.0 things.”
Justin Kan's Snapchat Journey
43:16 to 45:05
Justin shares his experiences and insights while using Snapchat to engage with followers.
“You had this era, and I remember this distinctly because my kids were so into watching you, where you would like, and we couldn't remember what platform this was.”
Transitioning to YouTube and Content Creation
45:05 to 46:46
Exploring Justin's move from Snapchat to YouTube and his content journey.
“I remember when my kids showed me you were like on your exercise bike.”
The Journey to Ayahuasca: Seeking Self-Discovery
46:46 to 48:36
Justin reflects on his journey to find purpose and the invitation that led him to try ayahuasca.
“It was on one of your like important life moments, right?”
The Ayahuasca Experience: A Transformative Journey
48:36 to 55:19
Detailed account of Justin's ayahuasca ceremony, including his challenges and insights.
“and I'd heard about it, didn't really know much.”
Post-Ceremony Reflections and Insights
55:19 to 56:03
Justin shares the aftermath of his ayahuasca experience and its impact on his life.
“At a certain point, they're like we're going to close this ceremony.”
Experiences During the Retreat
56:03 to 57:20
Justin shares a transformative experience during a spiritual retreat.
“I'm just like lying there like, yo, that was crazy.”
Realizations from Ayahuasca
57:20 to 59:38
He discusses insights gained from ayahuasca about self-approval and happiness.
“Like physically, I felt like there was like, I'd gone through this deep catharsis.”
Shifting Motivations in Entrepreneurship
59:38 to 1:01:52
Justin reflects on how his motivations for entrepreneurship have evolved.
“not for my successes or whatever, but if I just show up as a good friend, as somebody who's like genuinely interested in curious and on the people around me, people love me for who I am, number one.”
Life Lessons and Future Outlook
1:01:52 to 1:03:00
He shares thoughts on how therapy and various self-discovery methods have shaped him.
“It was more like I learned this insight and then I had to change things in my life to show up in a way that where I was like really happy with how I was showing up in the world.”
Transcript
Automatic transcript. May contain errors.0:00Carolyn, I'm so excited. Today we have Justin Kan on the show. Hi, Justin. Welcome, Justin.
0:10Justin Kan:Hey, what's up, guys? So happy to be here. Nice to see you. We're so excited. So for any listener who doesn't happen to know who Justin is, he's the founder of, well, originally it was JustinTV, but that turned into Twitch. So he's going to talk a lot about twitch but even more than that because we have known justin for i've known him for 20 years now because he and emmett sheer were in the very first y combinator batch in 2005 can you believe it that's amazing that is that is crazy it's crazy that we've known each other for 20 years because i remember coming into this industry and like hearing people be like oh I've known that guy for 15, 20 years.
0:54Justin Kan:And I was like, wow, that's a long time. It is a long time. Like I've had kids in that time. You've had kids in that time. Like it's just been just a lot of changes. How old were you when you did YC? I was 22. Yeah, 22. I think I went through my 22nd birthday actually during YC in 2005. Yeah, that was crazy. I knew nothing about anything at the time. So you applied to YC during your senior year at Yale. Is that right? Yeah, that's right. So Emmett and I had a company with our other friend, Matt. We had this calendar company. And maybe you remember it's like called Kiko. Maybe I remember. Give me an eye break.
1:40Kiko, come on.
1:42Justin Kan:One of the classics. But we had this idea. We saw Gmail come out. And we had this idea for making a calendar version of Gmail. and we didn't know anything about like internet startups or how you would make money from it or anything. We just thought, Hey, that'd be cool product. And so we started learning to build a web app at the time. And then a senior year, we were kind of working on this while we were going to classes and our friend, the stroke of luck or fate or whatever that changed our lives forever sent us, he got an email from Paul advertising Y Combinator's summer founders program. And he was like, hey, you guys have a company.
2:23Justin Kan:Maybe you should check this out. And I - Who was the friend? Was it a guy at Yale? Yeah. And he was a friend of Emmett's. He was in the computer science department at Yale. And we got the email like the day before the application process was due. That was maybe March or April of 2005 or something like that. And then I was like, we should do it. Let's apply right now. And so Emmett and I spent like all night writing the application, you know, deciding what kind of animal we were or whatever, and then like submitted it the next day. That was the, that would change it forever for us. Had you ever heard of Paul?
2:57Had you ever read an essay?
2:58Justin Kan:Yeah. Emmett had been a fan of Paul. That's why he was excited to apply, you know, because he'd heard of Paul and I hadn't really been into CS before. So I, you know, I hadn't heard of Paul before, but Emmett was super excited. So we were like, we were like, Hey, someone might give us money for our company. That would be crazy. Like we should definitely try to do that. I definitely remember your interview in, and it would have been in like March, 2005 for the summer, We were going to have the first dinner in June. And you guys were totally legit. Like you had started working on the product. And to be fair, the idea was amazing.
3:40I mean, too bad Google launched Google Calendar. But like your idea was really solid. You could build it. You were from Yale. We were like, yes. Do you remember that interview?
3:51Justin Kan:Yeah, I remember the interview. What happened was we came in, we took the train into Boston and stayed at the Somerville La Quinta Inn. I mean, I think Somerville was gentrified a lot at the time, but that was like really sketch. And then we were trying to get a taxi in the morning. There was no Uber or anything. And it took us, it was so hard to get a cab that we were a little late. I think we were like five or 10 minutes late and I was like dying inside, you know. But we got there, you were super nice. You were like, oh, it's not a problem. So we go in and then we're opening. We had been up until like 3 or 4 a.m.
4:26Justin Kan:trying to make a demo, our demo work really well. And so we get in, you know, show the demo. It's a calendar app. It's basically like Google Calendar, except, you know, shittier in every way. But the same idea of like you can make appointments, drag and drop them around, stuff we take for granted now, but that didn't exist in 2005. And then Emmett basically spent the entire time arguing with mostly Trevor, but also, you know, RTM and Paul about whether fat client apps like JavaScript heavy apps would be a thing or not. Because most of the apps at the time, 20 years ago, were built where they were all done on the server.
5:06Justin Kan:And then the server would send you a small page to render. And our app was like Gmail, which was more intense on the client side, on the end user computer. The interviews were 40 minutes at the time. And it was like seven minutes of us demoing our thing and like 33 minutes about arguing about CS. And I'll tell you, I'm sure the reason why was because we had already decided, yes, we're funding them. So let's just, you know, get into some cool conversation. Because arguing means you're doing well. Yes, for sure. It's like you're engaged, right? Yeah. But when things are silent and like Trevor does all the talking, that was the bad sign.
5:46Justin Kan:That was the death knell. But that was the death knell when Trevor was like spearheading the interview at that point. Because Paul had like checked out. I'm making Carolyn giggle. Paul had totally checked out. RTM never spoke anyway. So that just meant we liked you guys and knew we were going to fund you. Yeah, we went. After that, we walked over to Harvard Square, and we're walking around for the afternoon. And then at the end of the afternoon, you guys called us and were like, hey, we want to fund your company. And we were jumping for joy in the street. Now, I remember you both had offers that you'd accepted from, like, he was going to Microsoft, and you were going to a consulting firm.
6:25And you had gotten, like, a$10 ,000 signing bonus or something, right?
6:29Justin Kan:Yeah. And so I sent the signing bonus back to this company, which was like, that's like the most money I've ever seen in my life, you know, so that was crazy. But, you know, me, I like, I want to do my own thing and like Emmett too. So we just were like, this is our shot to do something. Let's just see what happens, you know. so you moved to god where did you move to boston oh we moved to roxbury which was awful but um we moved to roxbury into this like why did you move because it was cheapest it was the cheapest place of course it was cheapest dude we never saw it get shot there yeah we never saw it we just someone a friend of mine who lived in boston like a family friend was like we were like hey can you look check out this place on craigslist the guy looked and he was like, this is totally fine.
7:18Justin Kan:We got there. We were like, great. But we were just basically in this apartment all summer, you know, hacking on the, like, there's no air conditioning. It was Boston summer. So like the window shades were all drawn. It was like, we tried to keep it as blacked out in there as possible. We were just sitting in the dark working on this application all summer. And afterwards, we had moved to, we moved to Somerville after that, which was also not that great, but like it was better. Yeah. Yeah. So tell me what tell me some of your best memories from that that summer batch. Yeah, it was just, you know, startups.
7:51Justin Kan:It's so funny because like, I feel like YC hit so many core things that make YC YC in the early days, either because you and Paul and we're like so spot on of like what was needed or by accident or some combination of the two. It's like the batch thing. So like I remember going through with other companies and being like, oh, I got to like we got to crank some code out because these other people are like legit. And we I don't want to look stupid. It's like Steve, Steve Huffman and like Aaron and like other people. People are so smart. I felt like we're like remedial. We need to like crank something out.
8:31Justin Kan:And so that was really motivating. And then just the speakers, like the speakers weren't that good back then. But there were some really great ones like Stephen Wolfram was the speaker. And then Langley from TripAdvisor, who had worked with Paul before. And he had sold TripAdvisor for like 300 mil or something. So that was, you know, it's still a lot, right? But back then, that was like a lot, a lot. And we were like, whoa, you can do this. Like someone could start a company, just set up a website, and it could be worth$300 million in some number of years. That is crazy. And so it was very inspiring to like, hey, we should just, we can, you know, it's possible to do something.
9:11Justin Kan:And now 20 years later, there's a lot more infrastructure and knowledge about startups and, you know, YouTube videos and everything. But at the time, there's like, you know, it was very opaque that anyone could even start a company, you know. There was so little information out there. And actually, if I remember, like we had limited access to speakers because we didn't have that many connections. And also there weren't that many startup founders in Boston. but also we were trying to bring in sort of the business side of things so we would bring in like a patent attorney to talk to the startups when the truth is like it took us like a year or two to learn like they don't care about hearing from a patent you know they just want to hear from the founders you know but i'm glad to hear that you enjoyed the speakers i think paul and i this is before we were married and had kids like we used to take you guys to dinner every once in a while right yeah that was so paul was cooking dinner for us every tuesday which was awesome and you know it felt like a very like family feel you know it wasn't like which was really nice like having dinner with people trying to like be like hey we need to like present something or like show other people like paul was like hey you know every every week you should be demoing to your peers you know batch mates and like showing some progress and then we're like we really were like oh yeah we need to do that um and then his encouragement to just launch like early and often or like you know it took us i think we launched at the end of summer or something but you know that was that was really powerful advice i mean i think we made tons of mistakes and ultimately at this company but like it was you know i think the that original format you know those things persisted today you know which is uh yeah it hasn't changed that much really exactly the the whole flow of it which is like come in work on your idea try to show progress every week kind of reporting to your peers and like it's more of like uh feels like there's a you have a peer set in something that would otherwise be lonely and then working up towards a demo day that all existed you know it's just gotten bigger and better in and more you know streamlined in like every axis one of my favorite subjects is talking about the very first demo day because it was It's so embarrassing.
11:26Justin Kan:Do you remember there were like 12 people in the audience? Yeah, there was like 12 people. They were all like friends of Paul's who he'd like made money for or worked with him at via web. But we did get an investor from it. Alex Lewin, who worked for Paul, he's like a friend of Paul's who just clearly came by to check it out. And he ended up investing$12 ,000 in a round. And then he introduced us to someone else who had worked with Paul at Yahoo. I was like an early Yahoo employee, Linda. Yeah. Very early Yahoo employee, Carolyn. Yeah. Oh. Those were your like two investors, right? Those were our two investors where he's like$62 ,000 and Paul put in some more money because he felt bad for us.
12:08Justin Kan:And then like we were on our way to like starting this company. And yeah, the demo day was like, you know, I don't know. It just, I don't, it worked. Like we started, like we got our start. If we were smarter, we probably could have made that company work better. But, you know, you have to learn. And we got our learning from that year working on that company. Well, here's what I want to know, though. Yeah. So that was the same time, right after we finished that demo day, that's when Paul and I decided, gosh, we got to go to Silicon Valley because we don't want someone else to be the Y Combinator of Silicon Valley.
12:44So we said, okay, guys, we're going to move out and do our Y Combinator thing in the winter in Silicon Valley. You can stay working. We let you work out of the Garden Street office. Yeah. I want to know what went on while I was away and no one was watching.
13:04Justin Kan:So a bunch of us, you kind of like left us in Boston. And so like some people, like a lot of people stayed there. I'm not sure everyone did, but, like, a lot of people stayed in Boston because, like, that's where we all moved. Free office space, too. Yeah. So we were working at Garden Street. I was, like, cooking dinner a lot of times for everybody. And we'd just stay there working out of the office. I think Paul let me stay at his house for a week or two when I was, like, moving between apartments. Well, this came up, Justin, because this is another famous story that you probably don't remember.
13:39Did I leave this door open? Yes. Yes, I do remember.
13:43Justin Kan:I feel bad to this day. He literally, he was living in Paul's house, which was a nice house in Harvard Square. He left to leave, to move out or whatever, wherever you were going, and literally left the front door open. Just to be clear, unlocked open or hanging open? I think a jar. I don't know what happened exactly. That's not like me. That's totally not like me, but I did. How did, so what happened? I think Paul's friend, Kate, went by and was like, dude, the door's out. What is going on? Yeah, Kate was irate. Yeah. Because she was sort of in charge of like looking after his house, you know, just checking in on it.
14:24And she's like, the front door was unlocked. Yeah, so I apologize. That's okay. I just love giving you a hard time because it's so insane.
14:35Justin Kan:Yeah, it's a super rude house guest move for sure. But overall, was it a good year working out of Y Combinator's office? It was good. The positives were like, it was like school where we like learn how to actually build production web apps and things. So like before we had never had jobs, you know, we never, honestly, we probably could have been better at starting a company if we had worked at a real company for two years. just to like learn how to even do like normal build scale web apps and like, you know, write production code and work in an environment where you have managers and like see people get managed.
15:13Justin Kan:Like we were kind of like reinventing all of that because we didn't know anything. So it was good. It was like we got kind of taken to school. And then socially, it was really amazing because we spent so much time with Steve Huffman, particularly who were, you know, he's like one of our closest friends. We're all super close now, 20 years later. And we were spending time with like Alexis and Aaron. And it was, that was fun. The hard part was like, we were not successful at executing our startup very well. And so eventually, you know, kind of Paul gave us like every opportunity. We almost sold it to Yahoo, you know, and then that he can add that connection.
15:48Justin Kan:And then after they like kind of did dipped and ghosted us, we ended up kind of sputtering out and, and YOLO selling it on eBay, you know? Well, I want to hear the eBay story. But I first want to ask you, do you remember when Google Calendar launched? Because it was like after that. Yes. It was like February of 2006. Yeah. Okay. So what happened when that happened? What happened? We had, we basically, Paul had kind of hooked up like a tour of Silicon Valley. So he had, you know, used the Silicon Valley connections to like set up meetings with Yahoo for all the companies. And then it wasn't so much that he had set up the meetings with Google, but he had like brought in like Chris Saka, I think, or someone else from Google, maybe a couple of people from Google.
16:30Justin Kan:And then they had like seen some of the startups. And so they set up some meetings with people, including ourselves. And so we had like meetings with Yahoo and Google. And these were like the two big Silicon Valley companies at the time, right? And Yahoo flew us out. But so they were basically both obviously working on like improving their calendar stuff, right? Google didn't have a calendar, but they had Gmail. It's pretty obvious you want calendar with email. so google was like we're not telling you whether we're working on this or not but we'd love to like learn about what you're doing so we went out and like kind of told them all the like stuff about what we're doing it's kind of like that scene from silicon valley with like where they brain rape the the pipe piper team it's basically exactly like that they come in where they won't tell us anything they're not like oh we can't tell you if we're working on a calendar or whatever but we're like want to know everything about exactly how you're designing and deciding everything so and we were like pretty naive we're 22 so we're like here is it here it is to be honest i don't think any of our ideas were that novel or anything so they were probably already like working on everything and they were like these guys are whatever are mid you know then but then yahoo we went into and um they were so behind technically they were like oh this is actually better than whatever we're doing they were like hey we want to buy your company can you we want you to come work here on the calendar product like an acquire yeah acquire and so we were like uh i remember the guy who was in charge of the acquisitions the corp dev guy for the communications department which was like messenger email and calendar um at yahoo he called me and he said we're interested you know would you want to come work here and he's we were like okay maybe and he said, how much would you want?
18:20Justin Kan:And I remember I thought at the time, I was like, I want a million dollars for him and a million dollars for me, which was insane. I mean, remember I just turned out$12 ,000, which I thought was like the biggest amount of money I'd ever seen. So that was like an insane amount to me. So I immediately knowing nothing about negotiation, having no negotiation skills, I was like$2 million. Without a pause, like no second pause, he was like$1 million. And I was like, done, easy.
18:49Justin Kan:And so he's like, yes, okay, we'll give you one. I mean, he clearly, he probably could have given us$2 million. Like, I just was like, I crumpled like a tinfoil. Did you remember, though, that you had to pay your investors back? So that wasn't all going to go to you and Emmett. Yeah, yeah, I remember. I remember that, yeah. I was like, I remember the investors owned, you know, whatever percent of it. It was like 20%, 30 % or something like that, whatever. But, you know, still, like, these amounts were like, anything was, like, better than what I, you know, like, I have my expectations. So he was like, I'm going to get a contract or term sheet or whatever, and I'm going to email you in a couple days.
19:26Justin Kan:So I was like, great. And then I never heard from him again. Oh, no. Even after he lowballed you, they said what they want to buy you? Yeah. So what happened, I found out years later, his boss, the guy who ran communications had just hired someone to do a friend, like a person in Silicon Valley who had experience to rebuild the calendar. And then they were like, oh, do we need these guys? So they were into it. But he thought, oh, I can actually save this. We should buy these guys. So he didn't come back and tell me no. He was just trying to work internally on it. And then they like, eventually by the time he got clarity, that too much time had passed and he was just super embarrassed.
20:10Justin Kan:So he just ghosted us. That's hysterical. Oh, gosh. You know, they didn't improve. I don't even know if they've improved the calendar to date, but they didn't for like 10 years it was the same. Like they basically didn't make any progress for like a long time. And so, but I told you, you know, I know ill will. Afterwards, I was like, yo, thank you. because if you did not buy us, then we would never have gone on to start our next company and Twitch. So who decided it was a bright idea to sell what you had, sell the assets on eBay? So we spent the rest of the year, we were like, is this calendar?
20:46Justin Kan:Google Calendar came out. It's like very crushing because their product was basically better than ours. Plus they had all the Gmail users. All our early adopter users started using their calendar. So we were like, okay, what do we now, what? So we were like thinking about pivoting. We built a bunch of different apps. We built like a to-do list. That's kind of like to-do list. We built like a family social network that was kind of like a genie or something like that. We built something that was kind of like an influencer scoring thing for MySpace, actually. A lot of these ideas actually became businesses.
21:19Justin Kan:But we were not good at like marketing or like launching them. So we kind of like would do the technical side. And then we like didn't like do any customer development. And so anyways, long story short, after about a year, we're like, this is, we don't know what we're doing. We need to like get out of this business. And I feel guilty about raising this, you know,$80 ,000 or whatever we've raised. So we need to like pay back our investors. So we ended up, I had seen a company sell itself on eBay. There's this company called Juxtool, which was like a, this search engine. It was basically a webpage that in two iframes searched Microsoft and Yahoo results, put them next to each other.
21:55Justin Kan:but anyways this guy sold this failing web page on ebay for like a hundred thousand dollars and i was like that's crazy we maybe we can do the same thing so decided to list our company on ebay this is like fall of 2006 and uh yeah we ended up fueling a bunch of offers for it people were like learning about they were like is this real then they're calling us up and doing diligence then they um you know kind of went viral on the internet because people are like why are these guys selling their startup on eBay. And then the morning of, we got a bid back. So it was like$80 ,000 was like the reserve.
22:32Justin Kan:I think the reserve price was like 50 ,000. And it went to like 80 ,000. And the morning of, I was visiting friends of mine in New York. And they're like 23 years old, so they lived in a really ratchet place in New York. No AC. So I'm like in my underwear at my friend's desktop computer refreshing our eBay page with like F5 like ref five that five that five like at the morning of let's like every minute pressing F I'd like to see what the auction was at and so it was at 80 and I was like oh that's crazy like we're gonna actually pay back all of our investors then it went to like a hundred thousand and I was like oh my god I make like a couple thousand dollars and then it was like 113 158 and it kept going up for the last 30 minutes until it reached like$258 ,100, which is a number that's like permanently burned into my brain now.
23:25Original meme stock. Amazing. That is amazing.
23:29Justin Kan:Yeah. So we were like, went from like failed founders to like, hey, we actually made money. That is insane. You know, like, like not a lot, but we made, it was like slightly more than, you know, it was more than zero. So after we paid taxes and kind of distributed to the investors and stuff, we basically made what we would have made if we just got an entry-level salary. But it was all in one lump sum at the end of the year. Yeah. So it was enough to keep going. You could keep doing something new. Yeah. So we were like – the most important thing was before we were like extremely discouraged about startups.
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24:04Justin Kan:We were like, we suck. After that, we were like, hey, we're okay. We don't suck. We're not great. but we're, we could keep doing this. And so then we went to pitch Paul for another company. Cause he was actually, Paul was also super encouraging. Cause he was like, Hey, do you have any other ideas for like another company to do next? And we were like, you would fund another company of ours based on this experience. Like that's an amazing, like, like, thank you for believing us. You know, we were like, that's crazy. So after we had sold the company, we went over to his back to, where was it? It was at Avon Street, his house.
24:44Yeah, I was at Avon Street, yeah. Because I walked in during the meeting.
24:48Justin Kan:Yeah, we were at his house. And I'll never forget this. Yeah, yeah, yeah. Why? Why will you never forget it? Because they were meeting in his kitchen, and I walked into the kitchen, and Paul's like, hey, Jessica, wait till you hear Justin and Emmett's new crazy idea. Justin's going to wear a camera on his head and broadcast his life in a reality TV show. And I remember, I think I said like, well, that's a dumb idea. Yeah, yeah. I mean, everyone, that was a consensus opinion. Yeah, but Paul liked it. Paul is like a savant at ideas. He's like so good at ideas. He was like, he tapped into, like I think something that I kind of understood, which is like people are interested in other people and they want to learn and follow other people.
25:35Justin Kan:And that was like the precursor to social media. Well, let's go into this for a minute because was this like leading up to the idea of Justin TV? Was it one of those things where everyone's like, oh, my gosh, Justin has such a crazy, interesting life? Or is it more like you guys sat down, had this idea, and you're like, I'm going to be crazy and interesting? Yeah, it was more of the latter because basically I was a shy extrovert. You know, I've like kind of grown into myself now and people are surprised to hear that. but like maybe you remember at Y Combinator I was pretty shy I wasn't like out there I was not there yeah but I was I was like intimidated by all these other people who I thought were way smarter than me and I always wanted to like be more out there but I didn't like really know how so that idea of Justin TV was kind of my own way of like forcing myself to like go do interesting stuff and be out there in the world how did you talk yourself into that you were just like this is this is like the next version of myself yeah I'm just like fuck it I'll try anything I'll try anything.
26:33Justin Kan:I don't know. I'm really good at forcing myself to do uncomfortable things for, you know, just because. Like I fast five days of no food every year in January, like for the last five years. Wow. And I was like, just I wanted to do that one year. And I was like, I've always wanted to do it. So I just YOLO. Let's try it. And then I've found it to be like a really interesting experience. You must feel amazing if you've done it five years in a row. afterwards yeah during really not great like dying my wife says it looks like the the the joy has spark has left my eyes i'm like starving to death but like afterwards i feel great anyways i'm sorry that's a total tangent but i'm just i just like to throw myself in the deep end on things you know yeah well this this idea was the deep end i mean you literally had a camera on your head and emmet and Kyle, who've both been on the show, talked a lot about how technically it was very difficult.
27:35This is back before there were reliable cellular connections and things. And broadcasting the video in real time was really hard. But you were sort of responsible for making sure the content was kind of interesting.
27:50Justin Kan:Yes, which I did not do a good job of, to be clear. You were the talent. That was the talent. I feel like I want to beg to differ. And I know you got a lot of early complaints like oh we're just watching you know justin's guy sleep or eat breakfast but i what i remember were many of the highlights that i sort of felt like i participated in my favorite with michael seibel um the startup school at stanford yeah where in bomb threat bomb threat and we were like two speakers before the event was over we had like hundreds of people and the head of security at Stanford was like, we got to evacuate. We got to evacuate.
28:29And Michael Seibel and I were like, no, please, please trust us when we say this is a prank. This is all a result of Justin TV. And this is a hoax. And the guy was like, I can't be taking these hoax. I'm like, please. And then we were on the last speaker and Carolyn, you'll appreciate this. It was our wonderful patent attorney in Boston. And he and I was like, Joel, man, you got to keep this quick because they don't really want to hear about patents. So just keep it succinct. He's like, no problem. This is going to be the shortest speech in all of startup school. It was like the longest talk in all of startup school.
29:06I literally was like crawling up onto the stage because I had the security guy breathing down my neck and I was like, Joel, be done. It was so stressful, Justin. But the one that I really want you to tell is when someone like swatted you and you were like the police came to your apartment and like, didn't they like kick down the door with a gun? Will you tell that story? Yeah, yeah.
29:28Justin Kan:So we all moved. We moved to San Francisco for starting Justin TV. So after Paul funded Justin TV, which is the idea of like, let's do a 24 hour seven live stream. We moved to SF because we were like, our next startup should be in SF. So we moved to this building. We found this building that a bunch of YC companies eventually moved into called the Y Scraper. That wasn't the real name of the building. Wait, you were the first people. Yeah, we were the first people. Moved into Crystal Towers is what it was called. To Crystal Tower, yeah. And it was month-to-month furnished apartments in San Francisco.
29:59Justin Kan:So it was very convenient for startups where you might move somewhere else afterwards. And so we moved in there. The guys from Zobny, the email thing, like Matt Brazina and Adam Smith, Dropbox guys, Reddit, Weebly. So there were a bunch of companies there. And we'd, like, have dinner once in a while together, like, every week. People would hang out. So we launched our show, you know, six months later in 2007, March 2007. And, you know, obviously people were pranking us. They were, like, trying to interact with the stream. All these things that happened to live streams today on Twitch or whatever, you know, were happening to us.
30:32Justin Kan:And so one of the things that people like to do to mess with us is they would call in bomb threats or, like, call fire department on us. They were, like, always, like, reporting fires at Crystal Towers. and so they called like a stabbing into our apartment which was super not cool but um we would keep our door unlocked because it was like people you know friends would just come and walk in you know it's kind of like seinfeld or something and so we had our door unlocked and i heard we heard this someone like a bang on the door one like four days into our stream like we just launched the stream someone's banging on the door and they're like open up sf police and And we thought it sounded like Matt Brazina, who's another YC founder.
31:18And so we were like, fuck off, basically.
31:21Justin Kan:And they kick open the door because the door is actually unlocked. So legally, they can enter. So they just opened it. And then the guy had his gun drawn. Kyle's like sitting right here. The gun is like right here. And we're like, yo. It's like an apartment full of nerds working on their computers. right so we're like and you can see it on the camera i'm like put my hands up like this i remember you had your hands yeah and uh we were like after that you know obviously they were like oh there's no body in here there's just a bunch of nerds nerds working on a startup and so they left and we were like yo first of all we told the emergency dispatch or whatever eventually after they called like a fire in on our poker night they called like there was like five fire trucks outside, you know, there's like a four alarm fire or whatever.
32:11Justin Kan:They were, they were, we, we, the 911 dispatcher was like, Hey, next time we get a call to this address, we're going to call you, Michael Seibel, you know, my co-founder and see if it's real. We were like, the fact that EMS works like that, like you're just going to call him. And if he doesn't like say it's like actually an emergency, then you're not going to send anyone is crazy. But like, that's a good solution. And so then we were like, do we, should we cancel our show? This is like way too intense, you know? Like someone could have gotten him, people got killed in swatting. Like there was, I didn't even know what a swatting was until like, you know, this was like early internet, right?
32:52Justin Kan:2006. So anyways, they, we ended up being like, okay, we're going to keep going. And, you know, that was, that was a crazy moment, but kind of died down after that. How long did you do Justin TV where you're actually you are the entertainment? Well, we were streaming for six months. But basically what happened was like the first like four weeks was like crazy. Like it was like just viral and building on itself. And like we were on MTV and the Today Show and trying to make content. But like but the retention was really bad. People would come and be like, this is interesting. But this guy's actually not that interesting.
33:26Justin Kan:Also, the format of watching someone just walk around for all the time is like not actually that interesting. So, you know, we kind of hit this viral moment. but it wasn't retentative. And so we ended up being like, we need to pivot to something. Lots of people had asked, Hey, can I create my own stream? And so we ended up building a platform for anyone to stream kind of like YouTube for live video, but it took us six months to actually retool to build that. So we ended up honestly probably should have been faster, but like there wasn't, we had to like kind of build all this infrastructure. So we ended up streaming while we were building this new platform.
33:57Justin Kan:And then in October 2007, we pivoted to be the platform. Yeah. Okay. And were there like, there were like early influencers before influencer was a word. Weren't there like Justine? Yeah, I think. Yeah, exactly. This is kind of like the core insight I think of Justin TV was people want to follow other people and they're curious about other people's lives. And if you give them a window, they're interested. they're interested and i think it's most analogous to kind of like the stories feature of instagram or snapchat where people are like you know putting up brief video clips or photos of what they're doing and it turns out in someone's 24-hour day only like one minute is potentially interesting so like we were streaming and creating content for like 24 hours per 24 hours and it should have been like one minute per 24 hours but i do think there was like a core insight in there that people want to follow other people and if we were smarter we would create a different app or something but that's you know well it worked out i was gonna say it turns out you were smarter because you ultimately pivoted to twitch do you remember that yeah so so what happened was like you know i'll give you the bridge version but basically we had this site that anyone could stream anything and people would stream all sorts of different stuff and um after a couple years there was like one category that we're really into which was gaming it really wasn't a big internal debate but emmet was the one who's like loved gaming the most.
35:24Justin Kan:And he was like, really, he was like, this is the only content that I care about and think is good on our site. So we ended up kind of nurturing that part of it and growing it. And it kind of eventually became Twitch, you know. Which is huge. And then you got sold for like a billion dollars to Amazon, which for YC, like I was like, this is amazing. It was the biggest exit that had happened, I think. I think at the time, yeah. At the time. Yeah, at the time, yeah. Remind us what year that was? 2014. Had you left Twitch before the acquisition or are you still involved at the time? I left before the acquisition.
35:59Justin Kan:I was just on the board. We started this other company that YC Funded that was called Exec. It was kind of like TaskRabbit. I don't know if you remember that. I remember because I loved Exec. I was a busy working mom with toddlers. Well, you should tell the origin story because if I'm remembering correctly, it's very entertaining. Yeah, the origin story. So this idea, so I, I mean, I was always thinking of ideas and like Emmett was really the one who was like running, you know, kind of building Twitch and, um, I contributed some, but like at the end of the day, I was like, okay, it's his product genius.
36:30Justin Kan:So like, let's, I gotta do something else. So I was thinking about this new startup. I had this idea. Um, well, so I was going to Burning Man, um, with the guys from Dropbox. Drew brought me to Burning Man for the first time and, uh, with a bunch of other YC founders in 2011. 11. And then I think the next year is when I thought of it. Cause in 2012, we were going to burning man and one of the guys had left his ticket at his house and we were like already in Reno or something. And so he was like trying to figure out how to get his ticket. I'm like, Hey, you should, there's another friend of ours leaving, but you need to get a ticket from like what point, you know, your lobby of your house to like this other friend before that person leaves.
37:11Justin Kan:It was like call an Uber, send them to Uber had existed then. So I send them to, you know, your address, call the guy, tell him, pick up this thing and bring it to here. And then he did that and it worked. And so after that, I was like, you know, there should be an app where you can just hire someone in the real world to do something immediately, whatever it is. Like TaskRabbit, you know, they had a long lead time. Oftentimes it was like hours or days before you like hired someone. And I was just like someone, there should just be like a pool of people on call to do whatever people want to do.
37:44Justin Kan:What? Why does my memory of that story involve a pizza where there was no pizza, there was no message. There was another time when we were trying to, when Twitch was down. This was like in the early days of Twitch. We had like one engineer doing every system. So like Kyle did all the video system. And there was like no one else who knew how it worked. like Emmett did the website no one else knew how to work there was like another guy did chat no redundancies there was no redundancy there's no documentation nothing so if like that guy got hit by bus we were screwed so we were like hey um Kyle went on vacation he's like I'm gonna go to Tahoe and I'll see you guys like on Monday or whatever you know this is a time when we were working like every day so um we're like you're going on vacation dude what the fuck like so he was like, I'm okay, I'm going to go on vacation.
38:36Justin Kan:And he was like, here's my, you know, you have my cell phone. So like, call me if you need something. So we like, of course, on Saturday, our busiest time was a weekend, because that's when like, more people were out of school or work or whatever. So we're watching. So the site goes down. And we're like, calling Kyle and call him like 10 times, no answer. So we knew where he was staying. So we called a pizza place. And we were like, hey, can you go to this address? We'll pay you for a pizza. We'll go to this address and tell the person the website is down. And the guy was like on the phone. He was like, what kind of pizza do you want?
39:15We're like, we don't want a pizza.
39:18Justin Kan:We'll pay you for any kind of pizza. We don't want a pizza. Don't wait until the pizza is made. Just go now. Send a delivery driver right now to read this message to whoever answers the door. So they did that. It was like after explaining it for another five minutes, we're like, okay, we got it. We, they, you know, and then Kyle, like it's a, there's a ring on the doorbell. He like wakes up, he's sleeping in the other, his phone's in the other room, he's taking a nap. And the guy's like, the website is down. And then he was like, calls us, you know, five minutes later, he's like, after he just logged in, pressed one button, restart, went back up, of course.
39:52Justin Kan:And then he calls us, he's like, why didn't you send the pizza? Damn it. I had a nap and now I want a snack. Yeah. So he, anyways, he'd like, that was, that was another instance where it was like, well, we want to hire someone, you know, immediately to do something. And so, so the, that's what kind of came up with the idea for exec. And, you know, I know that didn't work. We ended up pivoting to house cleaning of all things, but like, it turns out people wanted certain categories of things. We should have picked delivering food or groceries because that was an obvious one that turned into Instacart and DoorDash.
40:26Justin Kan:But instead, we picked house cleaning, which was dumb for a lot of reasons. Yeah. Anyway, so that was another attempt to build something. And you started that with Daniel, your brother, right? Started with my brother and our other friend Amir, childhood friend. And yeah, we worked on that for about two years. Clearly, the house cleaning side, the problem with house cleaning is I think what we learned, you know and I thought a lot of other Silicon Valley people learned this over the years is like services doesn't necessarily scale as well like especially when they're powered by humans as technology uh despite the fact that you wanted to and so there's just like a huge amount of like errors and edge cases when it came to having human cleaners in people's houses to make the margin you know the margins didn't really work very well and then the user acquisition costs were like too high for the to make the the business work really well and so at the end of two years we were like okay let's just we sold it actually we ended up making money like a little bit it was kind of like a kiko's like situation but we had raised like three million dollars or three and a half million dollars but we ended up selling it to a competitor that's ended up selling themselves to angie's list years later and oh wow we got some cash out of it oh nice but i mean justin i'm looking i like sort of scribbled down a list of all you've you've started a lot of companies because then I've probably started like 15 companies it's going through all of them would take forever which one is there one that we should ask you about is there one that there's some interesting stories or lessons about I've learned so many lessons I think you know I guess that services not scaling one is one so like definitely I think one what one thing that happened in the arc of Silicon Valley was like people made a bunch of money with mobile and building things, you know, different mobile things.
42:19Justin Kan:That was kind of like in the era. There was first a bunch of like Web 2.0 things. Maybe you could consider Twitch that. And then there were a bunch of mobile things like Uber and Instagram. And then people started being like, Uber, let's do like the Uberization of everything. And then a lot of things are more services than they are technologies to scale. And I think I made my mistake probably multiple times once with Exec and then with atrium our legal startup we're trying to scale kind of like systematize and productize the legal services you know as carolyn probably could have told me and saved me multiple years of my life like did you tell him carolyn probably probably probably like people want their lawyer to be like a consigliere like that knows everything about them and like is like super deep with them and they are more cost agnostic especially the people who are actually the customers you want yeah the clients you want.
43:07Yeah.
43:08Justin Kan:And so, you know, trying to scale that more as a technology play, but it, you know, that was not the answer at the time. Maybe it would have worked with LLMs now. This is a little bit of an aside from all your entrepreneurial ventures, but we were talking about this before the show started. You had this era, and I remember this distinctly because my kids were so into watching you, where you would like, and we couldn't remember what platform this was. Snapchat. Oh, Snapchat. How did we forget? Yes. You, you were big on Snapchat. Like, yeah, that was so fun. Yeah. So I was at YC at the time. I'm like, um, you know, so after exact and we sold Twitch, I, right when Twitch was selling, I joined YC, um, and I was a partner for a couple of years, which was like really fun.
43:52But, um, by the way, it was fun. I love doing interviews with you yeah unfun what i see was it like 2014 to 2017 2014 to 2016 end of 2016 so
44:03Justin Kan:like right okay two years batch started two years i think it was five batches in the house i know it's great it's great good very good justin brings great energy yeah and a great voice and a great thank you yes yeah i loved there were so many people who i love doing it with like i i loved it when michael and i got to because we it was like being co-founders but without the drama and stress of like actually our company failing actively, you know? And then Gary and I always worked really well together and it was so much fun. Well, go back to Snapchat though. I saw Snapchat had blown up with stories because DJ Khaled, who's this rapper, you know, music producer had like gotten lost on his jet ski and he had been like recording Snapchats of it, like him in Miami, like being like, oh my God, I don't know if I'm going to make it.
44:48Justin Kan:Like, where am I? And it's like, the sun is setting. He's like driving around a jet ski. And it was like kind of a viral internet moment where people like this is hilarious and i had i was like what is the stories feature and it turns out you know you're just like posting it's like in instagram stories you're just posting these video snippets or whatever and so i was trying to like figure it out and so i just started posting my own stories and i was like what's up it's justin i'm here like gonna tell you some startup knowledge or whatever and so i was telling people about like life advice or like how to start companies or, you know, stuff like we'd tell.
45:21I remember when my kids showed me you were like on your exercise bike.
45:24Justin Kan:Yeah. So then I started, I started like being like fitness is the first step to greatness. And I'd be like, you got to work out to like feel good. And so I'd be like, you know, on my exercise bike, like working out, it was kind of fun, you know, it was a creative side. And so I'd make these stories every day and it grew. I was kind of like big in Silicon Valley. It was like not big for like real celebrity Snapchat, but I was like locally in Silicon Valley, people were following it. I think no one had like really created any like tech influence, you know, business content or whatever. And so people like that.
45:56Justin Kan:They like the startup content. I had a lot of fun doing it, but the Snapchat as a platform kind of got killed by Instagram for the stories component. And so I didn't want to rebuild it on Instagram. And then I stopped. And years later, I started doing YouTube as a way to create content around tech and things I learned about living life. I watched one of those today. Yeah. I watched you talk about your biggest moments in your life. Yeah. I basically made a YouTube video about everything I have an opinion on. And then I ran out of – I was like, okay, I already made one on meditation. I already made one on fasting.
46:33Justin Kan:I made one on how to start a startup or how to pitch your startup or whatever. And then I ran out of topics and now I haven't really made them very often in a couple, couple years. Will you tell us about ayahuasca? Oh yeah. Yeah. It was on one of your like important life moments, right? Yeah. Yeah. I, um, so, you know, I learned a lot about myself through all these startups and I've considered myself like really blessed to have had this journey with like being able to kind to do all these amazing things and like really learn about my, like put myself in the, this uncomfortable moments, like startups are the ultimate, like uncomfortable moment to stretch yourself and learn.
47:15Justin Kan:And I remember after starting Twitch, I was like, it didn't feel like enough. You know, I'd always thought, Oh, if we just like, I think a lot of startup founders are like, if I just get to this milestone, then I'll finally be good. You know? And that's like, first it's like, if I just get my product launch, I'll be like able to take a breath. And it's like, if I get a series, a seed, you know, if I get into Y Combinator, if I get a series A, if I get a series B, if I get this customer deal, if I sell my company. And I had went through that whole journey for like seven, eight years. And then we sold the company and I was still like, I was like happy for like a month.
47:47And then I was like, well, now, now what, now what am I supposed
47:51Justin Kan:to do? So ended up going to Y Combinator, but that didn't feel like I like to be more hands-on, You know, ultimately I like need to do things myself. And then I was, then I went to, um, then I started another company at Atrium and this company, it was like a legal services company. It's like, I only started because I thought it was a good business idea, but it wasn't like my passion. Right. I just thought this could be a big company. You know, I was like looking at all my friends who were more successful, the Brian Armstrong's of the world or Brian Chesky or Drew or whatever, and being like, Oh, I should have done better.
48:22Justin Kan:I can like make more, build a bigger company or whatever. And I was like always dissatisfied. and so that was my motivator, and then randomly a friend invited me to ayahuasca, and I, you know, just as I've described, it's like, I'll try anything once, you know, just to see what happens, and I'd heard about it, didn't really know much. He described it as doing a thousand hours of therapy in one night, and a lot of people would hear that and be like, I'm good, but I heard that, And I was like, all right, like YOLO, let's, I'd love to try it. And so a month later, he invited me to, um, this ceremony, ayahuasca ceremony that we're doing at this house in Big Sur.
49:05Justin Kan:And I remember showing up. First of all, I brought my wife who, it was funny because she had no idea what this was. She was like, Hey, we haven't seen each other. We've been, I've been traveling the last couple of weekends. Like we haven't seen each other for a while. Like let's hang out this weekend. And I'm like, Oh, well, I want to go to this ayahuasca ceremony. Why don't you just come? and so without context she ended up coming and we show up there and walk in this house and um nothing no idea what to expect the first thing i saw i remember was this guy who's now a good friend a matthew um who's kind of like a white stanford educated kid and he was i had this like hipster mustache and i was like he was wearing a robin hood hoodie like the stock trading app because that was like friends of his and he was like one of the facilitators and i was like this is some Silicon Valley shit right here.
49:54Justin Kan:Still, this is Silicon Valley. And he, you know, so we're sitting there. We're all kind of gathered in this house. And they're like, you know, William, the shaman, comes out. And he was saying, like, we're going to do the ceremony in Spanish. He didn't speak any English from Peru. And we're like, okay, what does that mean? That's no context for any of this. And so we sit around and end up one by one. You go up and it looks at you, kind of eyeballs you, and then pours a couple of eyeballs and hands it to you and drink this thing. It's kind of like the worst jungle cough syrup I've ever had. I kind of choked it down, sit down, and then they turn out all the lights, and we're just sitting in the dark in a circle for 45 minutes.
50:43And I'm like, what's going to happen? nothing happens that's too much anticipation 45 yeah i know i know it was intense i'm like is
50:53Justin Kan:anything gonna happen in the dark we're sitting in the dark and then at a certain point they start doing icaros which are these traditional chants um and they're doing these chants it's supposed to bring out the medicine and i'm just sitting there nothing happens and then after about 40 minutes of that 45 minutes of that they say hey if anybody wants to come up and get a second cup of medicine, you're welcome to over opening the second cup and you can come up. And I remember someone had said earlier, like before it started, they were like, you know, there's going to be a ceremony and they can have multiple cups.
51:27Justin Kan:And like, if you could even conceive of standing up, walking to the front and getting a cup, then you can have, you should have another one. Because you're not, you're not, you haven't had enough of anything. Yeah. You haven't had enough. Okay. So I just like jump up. I'm like, and I'm the first one at the front of the room. And then through the Matthews translating it from Spanish, William is like, how does it feel? And I was like, I don't feel anything yet.
51:58Justin Kan:That's a rookie move. He looks at me and he pours a giant second cup. It's like, boom. And I drink it, sit down. And then five minutes later, I'm like, start coming up super hard. And I was like, oh, no, that was for sure the first one. Because like, there's no way it had gone into my system. Oh, no. Yeah, yeah, yeah, yeah. Oh, no. Basically, I went into this crazy second dimension or whatever, where I'm like, yeah, I felt like Tron. The room is completely blacked out, right? Dark. And I felt like everything was lit up. I'm flying through this alien space city where, like, everything's lit up.
52:42Christine's still there, right?
52:44Justin Kan:Yeah. She's in another dimension, though. She's standing next to me, like, five feet away. But, like, she could have been in Mexico, like, or on the other side of the planet. I was like, this is – I am only worried about myself right now. And so then I'm, you know, I'm having these visions of people in my life. And I remember my dad appearing in front of me. And I'm screaming at him. I'm like, why aren't you proud of me? I've done so much stuff. Like what is going, you know, for like an hour. And, um, and then there's this other moment where I remember I'm holding this bucket and, uh, ayahuasca is a purgative sometimes.
53:22Justin Kan:So I'm like, I felt like I'm, I'm pulling this bucket. I'm like throwing up in this bucket. And it's like my stomach, esophagus, mouth, and this bucket are one organism designed to just pump liquid this way. And I'm like, oh my God. I felt like I was so sick and I was going to die out of the chaos. It's a crazy story. I remember Matthew came over and he touched me. I'm like kind of yelling, rocking to myself, like vocalizing a lot. And people are mostly like sitting there quietly. And I'm like freaking out, having like a full-on meltdown. And so he comes over and he touches my arm and he's like, hey, Justin, we're worried about you making a lot of noise.
54:03Justin Kan:how are you doing? And I was like, I don't think I can do this. Like I can this, I don't know if I'm going to make it. I think I'm going to die. And he's like, Hey, you're a strong person. Take a deep breath and be calm. And I took this breath like, and I went, it was like the, it felt like the first breath that I'd taken in a thousand years. And I went from the worst I'd ever felt in my life to immediately calm and centered. And I'll always remember that moment because it taught me that no matter what's happening in the outside world, there's like inside your natural experience is calm. It's like nothing.
54:43Justin Kan:It's inert. There's nothing happening. You're just observing all of these different, you know, phenomenon in your mind. And it was relevant because a year later, I ended up breaking both my arms in a bicycle accident. Like I flipped I shattered my left elbow and I broke my right elbow. Oh, my God. As I was like lying there in the street and then in the ambulances or taking me to the hospital, I was like perfectly fine. I'm like calm. And I was grateful. I was like I'm just – I'm alive and like I can survive anything. Did you remember the ayahuasca experience? Yeah, and I went back to that experience.
55:16It was like just be calm.
55:18Justin Kan:You have the ability to be calm no matter what's happening in the world. So back to ayahuasca though. I wake up. At a certain point, they're like we're going to close this ceremony. Please sit up. And I'm like, there's no way I can sit up. I'm lying in a fetal position. Sweat has soaked through all my clothes. My arm's in the wrong hole of my jacket. I've been trying to put it on. So it was like, but I didn't have the like capability of figuring out like how to put on a jacket. So I just like had it wrapped on myself because ayahuasca can make you cold and hot, like have temperature regulation difficulties.
55:52Justin Kan:Right. And so I'm like, kind of like freezing cold in this like fetal position. and they're, they close the ceremony, which means that like they stop, everybody's getting food and stuff. I'm just like lying there like, yo, that was crazy. And Christine also had a similar like crazy one. We get up hours later, everyone's like gone to bed. We're like, get up, grab some bread and coconut water. We'd been fasting for, you know, since the noon or whatever. So, and then we go to this tent, we're staying in like a glamp on this property, going to this tent and we're like why do people do this we need to go home right now like we should get in our car and drive back to san francisco now but it was 5 a.m so we're like that's crazy because you know three hours or whatever we should just sleep then tomorrow we're just gonna get in and we're gonna go and um they were we wake up we're like feeling better you know a little bit better they had prepared this like really beautiful spread uh food from big store bakery and we're like all right we'll stay for lunch it would be like messed up to like not stay for lunch so we're at lunch and then people are like hey you know everyone's different every ceremony is different you know you need to do a couple in a row because we had been planned to do two nights and so they do it one night and then you do it the next night like you know you should stay and so over the course of lunch we're like kind of talked into like staying again and so or like stay and i remember that feeling that next night we're like do the same thing sit drink it and this time it like starts to hit more quickly so like in 30 minutes or so i start to come up and the whole uh room is kind of like glowing green like night vision goggles like zero dark 30 like yeah and i was like why did i do this again like what did i why did i make this decision Why are you doing this again?
57:46Justin Kan:Yeah, this is insane. So that one was crazy too. Next day though, I feel incredible. I felt incredible. And I was like, wow, I feel amazing. Why? How did you feel amazing? Like why? Like physically, I felt like there was like, I'd gone through this deep catharsis. It felt like I had, yeah, like let go of something. And I remember that in the months after, weeks and months after I came to realize from that vision I saw with my dad, I'm screaming at my dad, why aren't you proud of me yet? I realized what that symbolizes. First of all, my dad is a great dad and he, you know, was, this is not, I didn't even know I had any of these feelings, but really he was representative of my like friends and peers and my parents.
58:30Justin Kan:When I was a kid, I didn't feel like I got the approval that I needed from the outside world. And every decision I'd ever made in my adult life to start a company, to try to be a famous founder, to make all these social media things to like try to care what people thought about me was all because I really wanted the approval of the external world. And that was like driving my, the driving force of my life subconsciously. I wouldn't have been able to articulate it before, but I realized that about myself. And that was a deep source of my own unhappiness in that I, you know, thought if I sell my company for a billion dollars or I have another unicorn or whatever, then I'll finally be happy.
59:06Justin Kan:And I went through that whole process and I realized two things. One is that I could love and accept that part of myself, even though it's not that attractive to admit that I just really care what other people think about me. It's like, I can accept that. And it helped me, you know, it helped me become successful, helped me have all these amazing experiences, even have the experience of doing ayahuasca, number one. And then number two is it helped. I didn't have to show up that way in the world if I didn't want to anymore. And so I could show up in a different way. And for me, the consequence has been realizing that like people will like me, not for my successes or whatever, but if I just show up as a good friend, as somebody who's like genuinely interested in curious and on the people around me, people love me for who I am, number one.
59:53Justin Kan:And number two is like, I can do things for my own intrinsic reasons, you know? And it's funny because a lot of people are like, hey, you were starting companies and investing before ayahuasca, and now you're starting companies and investing. So like, did anything change? But it's like the place that I'm doing it from, it's like, now when I'm starting companies, it's not because I want to get to some outcome. I'm like, oh, it has to be a billion dollars. It has to be$10 billion. Now it's like, I'm doing it because the remote things I liked about entrepreneurship, right, which is like learning about new things.
1:00:22Justin Kan:I love mentoring other people. I love coming up with ideas and like applying my creative mind in business. And so I just try to do things from the intrinsic reasons now. And I find myself much happier. You know, the test I always use, which is actually what I advise other people often on is what if after today, if like everything I did today, like all the companies are advising or whatever I did amounted to like no money, they're all unsuccessful and no one ever found out about them. What I feel like I wasted today. Or would I just like, was it a good, still good use of time? And if the answer is yes, then I know I'm doing things right.
1:01:01Justin Kan:If the answer is no, then I'm like, I shouldn't be doing those things. That's a very insightful metric. Yeah. Yeah. Well, we love you no matter what. But it sounds like a very like, you know, positive way to approach life, you know. Do you think a therapist could have gotten you to the same place? Or do you, I'm just curious. Yeah, I think for sure. I, I, um, therapy is like, I went to a therapist for years too, especially at times when my companies were failing and I was like, how do I motivate myself? Or I felt like burnout. I'm a proponent of all of the, um, self-discovery modalities, you know, whether it's, um, like therapy or, um, you know, ayahuasca or meditation or there's so many different things.
1:01:47Justin Kan:And it wasn't like so much that I just did ayahuasca and then like was healed or something. It was more like I learned this insight and then I had to change things in my life to show up in a way that where I was like really happy with how I was showing up in the world. I love it. Maybe this is a good place to end. I think so. I think this is a very positive note. Yeah. Well, thank you guys. You know, you changed my life for sure. I loved like just sort of catching up with you because I feel like I saw you really briefly at the retreat last summer. I saw you really briefly at the 20th reunion because I was on like planet Mars.
1:02:24There's like a million people there.
1:02:26Justin Kan:There's like thousands and thousands of people. So it's – I like miss seeing you. Me too. Like I said before, you were such a fun coworker. Interacting and doing interviews. I was like Justin is so much fun. It was – I have only fond memories of all that. That was fun. I loved being at YC. There were so many great moments of it. Definitely good times. Well, thank you for coming on the show and sharing all your stories. And hopefully I'll see you around San Francisco when I'm there next. Yeah. This is going to be a great episode. Love it. All right. Thanks, guys. Bye. Bye. Justin Kahn. I love his voice.
1:03:09His voice is the best. And he's such a great guy. I was saying this, you know, but he was such a fun coworker. I have really fond memories of working with Justin. Fascinating hearing about all the ayahuasca stuff. I know, like, I know zero about it, just so you know. Yeah, yeah, yeah. I love how he approaches talking about it. Like, he's not, he's just, he's an open book. He'll tell you anything. Like, it doesn't matter if it's, you know, I don't think he gets embarrassed. No. Or gets weird about anything. He's just like, this is what happened. This is, and he just like, he's, I just, it's so honest.
1:03:46It's like, I love it. And like, just as he mentioned, like there's 15 plus startups that he has on his, on his resume. It's just, that's like, it's amazing to just sort of embrace entrepreneurship like that and just keep like figuring out what, try to make something people want, figure out what you like to, you know, what you like to make, what you're interested in. like, I think he really has a good formula. He and Emmett were kind of like the purest data point of funding people who are young to sort of do what they were interested in. Because, you know, young people like that, kind of 23 year olds or whatever, embody future demand of things without knowing it, you know, sort of subconsciously.
1:04:34Well, and also, I think Justin, in particular, has the skill of knowing like how to hit on cultural moments. Yeah. So like start of social media, start of influencing the fact that he embraced, you know, he was telling the Snapchat story. Like he was always like someone who was, to me, felt like he was always there first, you know? Yeah. And that's a gift. I love it. It's going to be such a great episode. Yeah, he's great. All right, C. Levy, I will talk to you the next time. Okay, bye. Bye.
1:05:09to the AIDS
From the publisher
In this episode of The Social Radars, we talk to Justin Kan, who has spent his whole adult life in startups, much of it around YC in some way. We've funded him three times, the first time in the very first batch, and he's been a YC partner too. So Justin has seen it all, and because he's so candid, he tells it all too.
