20VC: Instagram Founders Kevin Systrom and Mike Krieger on Why Social Networks Should Be Less Social & The Next Wave of Social | Why San Francisco Will Return with a Vengeance and The Future For Remote Work | Let's Get Personal: Relationships to Money, Be

Kevin Systrom and Mike Krieger are the co-founders of Instagram. Since its release in 2010, Instagram has become of the most significant products in modern society shaping the way millions of people engage with the world around them. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized news feed driven by artificial intelligence. In Today's Show with Kevin Systrom and Mike Krieger We Discuss: 1.) The Perfect Partnership: Question from Josh Kushner @ Thrive: What makes Kevin and Mike such a great partnership? What was the last disagreement they had? How was it resolved? They built Instagram in person, in an office. They are building Artifact remotely, what has changed in the way they operate when comparing remote to in-person? 2.) Why Social Networks are Broken & The Next Frontier: Why does Kevin believe social networks today are broken and should be less social? What fundamental premise are social networks built on that Kevin believes is wrong? How will AI and machine learning be central in the next wave of social? How do Kevin and Mike evaluate TikTok and the next wave of content discovery? 3.) Welcome Artifact: The Comeback: Why does Kevin believe they chose the worst idea for their new company? Why is it? Were they nervous about founding Artifact and expectations being so high given Instagram? Why does Kevin argue that Artifact is not actually a "news app"? What does Kevin believe is the biggest lesson Apple taught us about messaging? 4.) Family, Money, San Francisco: Why does Kevin believe that SF will return as the centre of tech once again? Why does Kevin believe that many millennials in the workforce today are entitled and soft? How has becoming a father changed the way Kevin and Mike operate and execute? How do Kevin and Mike assess their relationship with money today? How has it changed? 5.) Hiring, Investing, Managing: What are some of Kevin and Mike's biggest lessons when it comes to hiring? What are the single biggest hiring mistakes they have made? Is it wrong to not hire someone because they are really really boring? What are the biggest lessons for Kevin and Mike from their angel investing?

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  I think that social networks need to become less social. That fundamental thesis is that your friends are into the stuff that you're into. And I would argue it is the greatest mistake of social networks in the last 20 years is to believe that is true.

• 0:13Harry Stebbings?

  This is 20 VC with me, Harry Stebbings. Now today we are joined by two co-founders who've changed the way we live in so many ways. Shows like this episode today are the reason why I love what I do so much. And so with that, I'm very, very excited to hand over to Kevin Sishtman, Mike Krieger, co-founders of Instagram. In January this year, Kevin and Mike announced their return to the founding arena with the launch of Artifact, a personalized newsfeed driven by artificial intelligence. I'd also want to say a huge thank you to a dear friend, Dave Clark, for the intro to Kevin's day, without which this episode wouldn't have been possible. Dave, I so appreciate that, my friend. But before we dive into the show today, SecureFrame is the leading all-in-one platform for automated security and privacy compliance. SecureFrame simplifies and streamlines the process of getting and staying compliant

• 0:58Harry Stebbings?

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• 1:42Harry Stebbings?

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• 2:24Harry Stebbings?

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• 3:08Harry Stebbings?

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• 3:30Speaker 02

  You have now arrived at your destination.

• 3:34Harry Stebbings?

  Kevin, Mike, I've wanted to do this one for such a long time. As I said, I referenced the shit out of you. Huge thanks to Dave Clark for the intro. Now, I spoke to Josh Krishnan before the show and he said that he has two truly amazing world-class partnerships in the founders that he's backed and that you are one of them. And so I wanted to start with the very simple, why do you think you work so well together? And I'm leaving this open to whoever wants to take it first.

• 3:59Speaker 02

  Pressure's on you, Mike. Go for it. Yeah, I think it is a rarity. We are second time founders. We've worked together for 13 years now with basically like a year break. And that was mostly us having left Instagram, us both having new kids. And pretty much even in COVID, we were working on projects together. I used to say it was because neither of us wanted each other's jobs, but I think that's a A little bit like a reductive answer. The foundation is like a tremendous degree of trust and integrity. And I think that's the unquestioned part that has, when things get crazy and you're fundraising or things aren't going well, or just all bumps that are inevitable in building a company, to know that you're not also questioning whether your founder has your back is huge. And I've never once had to question that.

• 4:42Speaker 02

  That's an enormous kind of foundational piece. I think we both also have the trait, and this is maybe one that we've acquired over the years, which is even if we disagree initially, it's often the case that after a few hours, we'll see each other's viewpoint and come back. Like, I can't tell you many times, Kev's told me something and he says, I see the Mike face where he's like, he disagrees with me. But then a couple of hours later, I'll come back and be like, yeah, you know what? I see how that works and this is different and vice versa, too. It's useful to have strong opinions, but it's also great to be able to, with some digestion, see the other person's perspective and maybe still disagree, but not feel like you're just digging in and retrenching, which is, I feel like where a lot of partnerships go south.

• 5:20Harry Stebbings?

  You mentioned partnerships going south there. Can I ask, do you agree that when you have a problem, you should discuss it straight away? Or do you think actually sometimes it's good to let it mallow and let it sit? I'm never sure which one's the right answer.

• 5:31Speaker 02

  I like discussing it straight away, but not feeling like you are going to resolve everything in that moment. We've done some angel investing and I've seen partnerships go south where there was some initial disagreement that either got lightly talked about, never fully resolved or never talked about, and then it inevitably blows up a couple of months later.

• 5:47Harry Stebbings?

  Kevin, what do you think makes you so special, other than trust, respect? Is there anything that you point to?

• 5:52Speaker 00

  I'm often just in awe of Mike's ability to get stuff done. I feel like I'm relatively smart, like I work hard. I went to a good school, same one Mike went to. We both went to Stanford, both did the same programs. I feel like I'm pretty good at a bunch of stuff, but man, there's a lot of stuff that I'm just not good at and Mike's really good at it. And I respect the hell out of that. Whenever I meet people who are just very good at their craft, Mike's craft is an interesting one because it's not like he's an artisan at code. It's not like that. His ability to pick up very difficult technical problems, very quickly diagnose them and make them right is unparalleled. And Mike, I'm not just trying to blow a smoke up your butt. I really do mean this. I like forming partnerships with people where I deeply respect their abilities in that

• 6:35Speaker 00

  way. I think that's what makes it really special. And then on the integrity bit, Mike likes to say I have a bit, the flips of my head on people, like whether I can trust them or not. And it's pretty true, probably if I reflect on it. But when I'm in on the people and I deeply invest and people don't realize this, but I care so much about my close relationships. I'm so deeply invested in them that when people do things that challenge those, I think it can be very hurtful in ways. And that's happened a bunch of times in my professional career. I even said this to him the other day. I was like, this matters so much to me that even if something questionable were to happen, we push through it and we try hard because it's not worth losing those 13 years. I also don't want to take it for granted because Mike and I haven't done a remote company before. We've

• 7:19Speaker 00

  seen each other how many times in person in the last year? Five? Maybe half a dozen, yeah. So my point is, I don't want to take that for granted because I think in new situations, it's like how you think, oh, if I just hire really technical people out of big companies, they'll work at a startup. It just works because they worked in this other context. I don't want to take for granted that a relationship in one context works in another context and will just work in the future. It's kind of like what people say about marriage, you have to work on it. And I think that's true in any relationship. But I feel like you want to ask about why we haven't seen each other more in person. I can see the face.

• 7:51Harry Stebbings?

  You got to marriage and I'm very single, so I have very little to add on that element. But my question to you was, you built Instagram in person and together very much, and now seeing each other five times or so in the year. How does the way that you act as a partnership change now remote versus in person?

• 8:08Speaker 00

  I think that there is a myth that like you can have the same friendship and our relationship ever again, because things change. Mike and I both have kids, we both have dogs, we both have wives, we both have homes. None of that existed when we met. We didn't get invited to fancy conferences. We didn't do any of that stuff. We were boring kids who liked to drink bourbon at a local place around the corner from our office. We had nothing to do other than work. And life couldn't be more different now. So I actually think what's more special about the partnership slash relationship. Is that it's been able to morph through all of this change? Because people lasting one company is one thing, but like it's one company and then beyond one company, it's a completely different life.

• 8:50Harry Stebbings?

  Do you think it's been able to morph because you've actually gone in the same direction? You both are now married, you both now have kids and it's scaled in a similar trajectory, respectfully to both of you.

• 9:00Speaker 02

  Yeah, I believe that. I think that there's a tremendous amount of empathy. I remember Kevin had kids first and I look at myself as a mid to late twenties person where my friends were starting to have kids and realized how naive I was a lot about things, that dumbest thing I ever said to somebody that was going out on leave was, do you have a bunch of books signed up that you're going to read during your like leave? And they're like, no, I'm good. This is the second kid. They're like, I'm just going to try to stay alive and if I can read the news of the day at the end of the day, I feel good. I'm not going to read a book. You learn a ton as a first time parent and Kevin got to do that first. But I think for sure, I think the fact that we looked at each other post Instagram and we both had that drive to still build. And I think if that were different, then I don't think we would be working together.

• 9:42Speaker 02

  I think that would have made a much harder partnership if one person was like, great, no judgment, but I want to coast or I don't want to do something or I want to do something a little bit less intense, but both of us love building. So when we looked at each other, we were still on that same page. But I would say, and this was a really interesting difference from Instagram. With Instagram, Kevin had some initial seed funding contingent on finding a technical co-founder.

• 10:04Harry Stebbings?

  I spoke to Steve Anderson beforehand. I told you I stored you.

• 10:09Speaker 02

  And Steve was like, great, you seem great and you're technical, but let's try to find a technical co-founder and that's where we partnered up. But the process from that to starting was not from us deciding to do it together to starting, wasn't contingent on us figuring out whether we were good partners. We did some of that, but most of that was actually me getting my work visa. So that was an artificial delay, whereas doing artifact this time around, I think we have just grown and seen things, spent a good couple of weeks just making sure that we were aligned on what we wanted out of this experience and that was really important. If we had skipped that, then there's always a risk of one person being like, oh, I was just excited to build this thing over and not have any real pace and keep it's whatever the different avenues might have been. So building that alignment was really different this time, whereas the first time

• 10:50Speaker 02

  With Instagram, building the alignment was, hey, let's get together at coffee shops and hack together and make sure that we could code with each other and build with each other. We took that as a given. Now it was more where we are in our lives.

• 10:59Harry Stebbings?

  Guys, I think the reason the show has been successful is because very quickly I just threw out the schedule that I sent you beforehand and I just asked you questions because I struggle generally in life. You mentioned there the multiple hats that you have from husband to father to running artifact now. I said to my mother literally half an hour ago, the thing I'm struggling with more, I'm always failing at something. I'm failing at being your son, a boyfriend, a founder of the media company, a fund manager. I'm always failing at something and it's really hard to get used to. How do you deal with the multiple hats and probably failing at something all the time?

• 11:31Speaker 00

  This is gonna be hard, Mike, because we don't fail at anything, do we?

• 11:36Speaker 00

  Are you kidding me? I feel like every day is a constant failure. It's even at Instagram, when Instagram was going well, it was a constant failure.

• 11:44Harry Stebbings?

  Why?

• 11:46Speaker 00

  That's the way that companies work. Everything's always broken and you're always unbreaking them constantly and they keep on breaking on you. Jeff Bezos likes to say that the greatest thing in the world is that customers are always unhappy because you can always build more stuff for them that makes their life better. It might sound a little cheesy, but it's true. Things are just always broken and you're always fixing something. And I think the myth that things are ever just in the stasis of good is totally BS. And what people need to realize is that like Ray Dalio likes to say, it's not about avoiding suffering. It's about learning to enjoy the suffering or choosing the right suffering because you're gonna suffer somehow. Choose the suffering that is most enjoyable, where you get the most reward when you work through that suffering. Again, I'm paraphrasing here.

• 12:31Speaker 00

  I like to say, choose what game you like to play in life. If I were a basketball player, I'm assuming I'd be practicing my three pointers and I'd be running a lot and I'd be like exhausted. To stretch this to the marathon, it's no one enjoys training for a marathon. No one enjoys running a marathon. You like winning a marathon. The idea that training is going to be easy or enjoyable, sure, I hope you get a runner's bike every now and then. But you just have to get comfortable with the fact that you're gonna be uncomfortable. Mike, what do you think?

• 12:58Speaker 02

  Yeah, I think that there's this drunk. Part of that, the thing I was gonna add on the failing bit is I think it actually goes back to partnerships. My wife, we've been together since before Instagram, so she's seen all of the insanity. And then I was like, I'm starting a new company or we're launching soon. It was not, oh, don't do it. It was, hey, let's make sure we talk about what that means for our schedules or how we think about our time with the kids and all of that, what commitments do we want to maintain? So failing in multiple areas while being alone in those areas is very difficult because you don't have any external signals to help you prioritize or to help you out, honestly. And Caitlin, I think, didn't even bat an eye. She just rolled over and was like, I remember these days, just go do this in a different room. But it comes back to you.

• 13:37Harry Stebbings?

  Speaking of that kind of muscle memory, you both spoke about this combined drive to build. Another thing that I ruminate struggle with is kind of relationship to money. I always watched Who Wants to be a Millionaire, this game show when I was younger. And when you won a million, you are happy, like life is done, you won the game. When I was like 21, 22, thanks to speaking to incredibly smart people like you and monetizing the shit out of you. When I was 21, I was able to do that and I was alone and I had no friends and I wasn't very happy. It was a really hard period. When you think about the drive to build, combined with bluntly not needing it like you did when you were young kids, having bourbon and figuring life out. Where do you think that comes from? And how do you think about the relationship to money today?

• 14:15Speaker 00

  It's a constant struggle, so I'm not sure I've figured it out. There's something called the hedonic treadmill where you have your first, I don't know, $40 bottle of wine when you're used to drinking crap vodka at the local dive bar. And you're like, oh my God, this Shiraz is so good or whatever. And then you have your first $80 bottle and you're like, oh my God, I could never drink a $40 bottle. And then you have your first $100 bottle, you're like, what the heck, $1,000 bottle? And then you go to some fancy party where someone serves you a $10,000 bottle of wine. And it just keeps going and you're like, this is ridiculous. This is grape juice. Now, to be fair, I enjoy wine, but this is grape juice and you can go that far on anything. TikTok likes to serve me watch, like I'm not into watches at all.

• 14:56Speaker 00

  But there are all these watch things where people walking around with $150,000 protect Philippe, whenever on their wrist. And it's just, it's absolutely ridiculous. And I'm like, why? Why do you care? And it's just because everyone feels like they have to. One up themselves and you're right, you get there and you're like, wait, I thought this was gonna be happiness. And happiness for me is when my little girl runs in and she says, Dad, I counted to a hundred for the first time. I'm like, what? We've been working on that for months. We get to 70 and all bets are off. You got it. That's happiness. It's cheesy, but the little things with family and friends and man, like money is such a siren song. But I think we're doing this not because of money. Of course, it would be great if we made this into like multi-billion dollar company.

• 15:38Speaker 00

  But the nice thing is we don't have to have that as the goal. So we can make building or doing the right thing, the goal.

• 15:44Harry Stebbings?

  Do you think it impacts speed of execution when you are up against it and have no money? And runway is running out and VCs are chasing your ass, getting you to get product out the door. You have real urgency.

• 15:56Speaker 00

  Potentially. I think it depends on your personality, though. So there's a difference between being pressured by others and being pressured by yourself. And I took all these like personality assessments, I want to say five, six years ago. And that thing that stood out was that I feel very little competition with other people. But I feel an enormous amount of, it's called challenge, which is competition with yourself. And it's possible we would have moved more quickly to launch or whatever if we had taken money and we had VCs being like, what the heck are you doing? And it's possible, or it's possible we'd be moving bigger on having a bigger team more quickly. But I'm not sure it's the right thing because we are definitely not lazy. Like we work our butts off. I'm in this chair, gosh, 16 hours a day at least.

• 16:39Speaker 00

  The only reason we work from home, by the way, is it's the only way to work this hard and see your family. At least that's my opinion. I don't actually particularly like working from home, but the fact that I get to work this hard and have a family life is incredible. And if I were working this hard elsewhere, first of all, I wouldn't work this hard in an office. It just wouldn't happen. But I feel like I'm way off the original answer, but what do you think, Mike?

• 17:00Speaker 02

  The question on like urgency, it's interesting because it gets to the heart of our partnership too. Because we both try to blend these elements of pragmatism and perfectionism. And if I had to score us like on the relative amounts, like I probably bias a bit more towards pragmatism. Kevin bias is a bit more towards perfectionism, but we both try to keep both in balance. Even with Instagram, I remember. We had already built Instagram and we were in the time you could have 100 testers on test flights. We had maybe 80 people using it and having conversations and we were always like, was it ready? This thing could be better. We had 16 filters. Are these the right ones? We had all these different conversations about whether it was time to launch. I know there's entrepreneurship cliches. If you're not embarrassed by the first thing you ship, you waited too long, which like is maybe a useful thing to put on a poster, but in the

• 17:44Speaker 02

  details, it's a little hard to say. It's like, do we have this feature ready? I look back at V1 of Instagram, I was really proud of the polish around the core features and there was stuff that was comically off. The second something got more than 30 likes on a post, it totally broke the UI when launched because we didn't summarize it. So you would just have everybody's names. It would be a wall of text this big. All sorts of stuff that this is in some ways table stakes, but on the hand, it was probably another week or two of dev. And I think timing can matter and getting out there and starting to react from actual customers really matters. And then with Artifact, the interesting thing is I feel like core UI, we probably could have shipped several months ago, but this is a product lives or dies by its recommendation. And so getting the recommendations into the spot where we were like ready to bring things on, bring more people on was the key. So I think you're always struggling with this question of,

• 18:29Speaker 02

  are you ready? Do you go? I think this time around, it was not a function of urgency or work ethic. I think it was a combination of more work just needed to be done to feel ready on the ML side, but also man, it's our second time around. And as much as I'd like to pretend that this thing will be judged purely on its own merits, there's both the pro and the con of it. It's Mike and Kev's second thing. It's great to have that attention, but it also gave us some pause around, yeah, we're like, we want to ship something that feels like it's thought through, it's ready and people can use it day one and not feel like, man, they really phoned it in or man, what have they been doing? And I think that was a helpful aspect of trying to calibrate, how ready do you want to be before going out?

• 19:06Harry Stebbings?

  Given the weight of both of your brands and the weight of Instagram, did you feel the weight of expectation, given the success of Instagram and your partnership before?

• 19:14Speaker 00

  Of course, of course. Every single day, I still feel it right now. First of all, we overbuilt the product. There's parts of this product that exist. You can DM people, you can post socially, like Facebook or Twitter. There's entire pieces Of this app that people can use, it's just locked away and not launched. Mike is being nice. We could have launched a year and a half ago. How do we not build that stuff?

• 19:38Harry Stebbings?

  Like, you are so patient. That's Kevin's perfectionism. He's as calm.

• 19:42Speaker 00

  In fact, I was the one who was like, we should not launch this. And the entire team's like, you're fucking crazy. We spent all this time building, like, are you insane? That was one of those moments, I think, I got Mike face for 30 seconds. And then when it dawned on all of us about how hard it was going to be to both launch this product and do moderation at the level we're going to need to with the amount of attention on this product, I think it made sense. But my point was more that if anything, I think we should have started with the kernel of the idea, launched that thing really quickly and then gotten feedback. And what we're seeing now, we chose the worst idea, by the way, for a second company, because the characteristic of this company is that you need lots of data to make the recommendations good, but you can only have lots of data if people like your product and come to it and use it.

• 20:25Speaker 00

  And there's all this pressure that the thing you put out definitionally is going to suck day one. Do you have to take this pain that a lot of people are going to sign up and be like, I don't get it. I see like a feed of news that I can get anywhere else. Why is this a thing? The good news is that a good portion of those people actually come back every day and a good portion of those people are producing data that makes the recommendations for the next set of people really good. But there's a big portion of people who, there's a big effing question mark over their head when they sign up day one. And that's painful for us because we want to build a product where people sign up and they go, ooh. Because they did it in Instagram. They signed up and they went, wow, filters. This is the best.

• 21:03Harry Stebbings?

  If you think about reducing the time to value, how do you make them get value on day one without that inherent data set? What's your Trojan horse insertion point to get the data?

• 21:12Speaker 00

  I think what people don't understand is we're not building a news service. Like, maybe I shouldn't be saying this as much as I say it. Well, no, I'm interested in core recommendations. I'm interested in the science of utilizing people's tastes and profiles to make sure that the world serves them. And I'm not talking just like Pandora and I'm not talking product recommendations. It's all of the above. The idea that you can take behavior or data and use it for a person's Benefit rather than for the company's benefit is fascinating to me. And it just so happens that news is a great place to start because there's a ton of information out on the web. Machine learning is very good at analyzing it and we can build portraits very quickly. By the way, this is the crazy part. People like to think they're really unique.

• 21:56Speaker 00

  They're like, oh, I'm like super unique. I have all these super unique interests. The core thesis behind recommendations is actually there are like groups of people that tend to think a lot alike. Not just ideologically, we're not talking like left, right, politically. I'm saying like, if you're in San Francisco, we can almost guarantee you're going to enjoy reading about startups from TechCrunch. It's not that hard to guess. You're generally not wrong. Or if you're super into the Atlantic and you're reading a bunch of mental health and wellness stuff. We know there are a bunch of associated categories with that and publishers with that. So your initial recommendations actually can be pretty spot on, which is pretty crazy. But to get to the level we want to get to, you do have to be much bigger. Where my interest in hi-fi audio systems is represented or Japanese architecture is represented.

• 22:41Speaker 00

  We're not quite there yet. Basically, we chose an idea where the ideal, we know what it needs to be. But bootstrapping it, that activation energy required is just like really hard. But because we are who we are, we can get some amount of press. We have hundreds of thousands of people sign up the first day. Enough people can get in that you can bootstrap it where if you're just some pair of, this is not a company we could have started at a Dogpatch Labs in 2010. We couldn't have done it. So it is an unfair advantage to get some eyeballs. The hope and the bet is that you can take that initial attention, parlay it into just good enough recommendations for a certain set of people. And then basically bootstrap and expand and then hopefully we can expand our purview over time.

• 23:21Harry Stebbings?

  Can I ask a weird one? It's so hard when you have scaling time, but also the desire to have a simple and beautiful product. It's something that I loved with Instagram was the product simplicity and design. How do you think about preventing feature creep with time and keeping that product simplicity? Because news and artifact could be so many things and that, Kevin, you mentioned DMs, you mentioned the sharing and there are so many avenues. How do you retain simplicity in product?

• 23:46Speaker 00

  I believe a lot in this jobs to be done theory where basically. Products are hired by the consumer to do something for them in their lives. It's almost like having a digital assistant and you have to ask why your product's getting hired. And if your employee gets new skills that help you do that job or similar jobs better and then you're excited. But imagine having employees like, hey, I'm gonna serve you really entertaining photos, videos from your friends every single day. So then you can feel more connected to them and they're like, and now you can shop. You're like, hold on, that's, that's not why I hired you. Or if it feels unrelated, it might work if you're big enough, but at the same time, it might confuse people.

• 24:25Speaker 00

  And I think people can only hold a complex enough idea of your product in their head, but it has to be simple. And if you complexify it, complicate it, they just generally don't want to open you. It's almost like in music, I've been reading a lot about music and they talk a lot about if you use certain tones, people will just stop listening to your music. In lofi music, there's in chords, there's the 13th, the 13th is, oh gosh, I'm gonna, every music lover's gonna crucify me on this. I want to say it's 1370, no, not 1370s. Anyway, it's above the root chord by steps, basically. And it sounds dissonant and there's all this data that says if you include it in your song, because you're playing the certain chord, like it sounds dissonant and people stop listening.

• 25:10Speaker 00

  And I feel like products are that way too. They can just grate at you if they include things that are dissonant to the core job. So you need to be very careful about forming that core job and only adding things in when they support the core job. But right now, we're what, two weeks old? We're gonna be like that core job and that core only. We are vanilla ice cream, but we're gonna be the best vanilla ice cream you've ever had. And you can have toppings later, because toppings are great, but like, we're gonna get to the toppings.

• 25:36Harry Stebbings?

  I mean, saying getting to the toppings.

• 25:37Speaker 00

  I like an award, I worked so many metaphors in there. There was, there was the sprinkles, there was court.

• 25:45Harry Stebbings?

  Do you know, Mike, Kevin's a DJ. He's a DJ. We got the semitones, we got the scale, everything.

• 25:51Speaker 00

  I had to read up on this before I actually quoted, though.

• 25:54Harry Stebbings?

  Do you know, Kevin, you could be a VC with that knowledge.

• 25:57Speaker 00

  Gosh, OK, fair enough.

• 25:59Harry Stebbings?

  My question was, you were like, we're vanilla ice cream and this is what we're doing. Love that, get it. I think the biggest problem I find today is messaging with companies and clarity of messaging. Kevin, you were like, we're not a news app. Oh, I probably shouldn't be saying that. How do you think about the right messaging for Artifact today? And how did that decision-making process go for you as both discussing it?

• 26:19Speaker 00

  To be clear, I'm talking to you. If you visit our App Store page, what does it say, Mike? It's like personalized news for you.

• 26:25Speaker 02

  Yeah, exactly. Artifact personalized news.

• 26:27Speaker 00

  So we're very clear to people what we are today. But it's almost if you listen to music versus you're talking to someone who understands music theory. You just talk about it in two different ways. And you have to understand our ambition is not to make, is not just to have a fun news app forever. We think fundamentally, machine learning is changing the way people consume social products. And we want to ride that wave and build the best social product using machine learning we can. But it's just so happens that we think there's this enormous unmet need in news that we can start on. Every app that is successful in social starts off as a utility and it becomes a large social behemoth over time. Now, I'm not sure if that's our future. Maybe we'll take a different turn, maybe we'll go in a different direction.

• 27:08Speaker 00

  But when they started Apple, if they had just said, we make desktop computers, imagine how limiting that would be. But everything I've read is Steve was like, we make great products, which is like very broad. But you can't tell a consumer, we make great products. OK, what are you going to do for me? But you can have that ambition. And that's, I think, the contrast that I'm trying to highlight.

• 27:26Speaker 02

  I think that's also where launching helps. As I would describe the product to people over dinner in the months leading up to launch. I'm like, people are made up of a lot of different interests. We had a really fun World Cup thread going inside the beta. Or maybe you're really into a particular type of architecture, a particular trend in fashion. And that's a lot of sentences. And the App Store gives you 200 characters. So it was actually very clarifying to be able to say. And I would actually go out of my way not to call it news, because I think, I think people are made up of a plethora of interests beyond that. You also Need to be able to explain things very simply in the App Store and you have to pick a category. There's no category in the App Store for apps that are generally about your interests and content. There's a news and magazines one, and that is the thing that most closely describes the core of what we do.

• 28:07Speaker 02

  So I think that's always that sort of play around your full ambitions or even the texture of what you're doing. And then also, great, give me the five words that describe what you do quickly. And you kind of have to have both and what's like a video game, good video games. You start with the basic sword and you can't do very much. And then as you explore, you're like, oh, actually now I can do this other thing that you level up and you go through it. I think good products let you build into having more advanced functionality.

• 28:31Harry Stebbings?

  Guys, I'm too interested. It's the next wave of fundamentally the abandonment of the social graph, actually, and the complete movement towards machine learning directed content discovery. The movement from a Facebook news feed to a TikTok or a news feed to a Reels. If we stay in the Facebook family and I don't get killed by Halit Schultz. Is that the next wave of social? Have we seen the abandonment of the social graph?

• 28:54Speaker 00

  Abandonment, I feel is a very binary way to look at it. I don't think you're going to see a complete abandonment, but I will say like, why do we use social networks initially? Because social networks were great filters. When I say social networks, the people you follow on a social network. They're great filters, first filters for content that's relevant to you. And that fundamental thesis is that your friends are into the stuff that you're into. And I would argue it is the greatest mistake of social networks in the last 20 years is to believe that is true. Because it turns out Mike is into very different. Yes, I like electronic music, Harry. It's true. Mike, you like F1. And if you show electronic music stories to Mike and F1 stories to me, that's terrible just because we're friends.

• 29:38Speaker 00

  By the way, our social graph couldn't be stronger and more overlapping. But your content is terrible for me, Mike. Now, yes, of course, it's media and voter theory. It's the stuff in the middle that satisfies both you and me, Mike. It happens to be tech news and it's like middle of the road stuff on chat GPT. Great, but what about all that like amazing texture that makes us people? That's the thing that I think TikTok or ByteDance, I guess I would say unlocked with TikTok. They realized that there's so much more to people than just their social graph. Your social graph is of course a usable signal, but to say that is the core signal. And when I say core signal, I log on to Facebook circa, I don't know, 2006 or whenever News Feed came out. I can't remember. 2006 is fine. The seven was the iPhone.

• 30:22Speaker 00

  You log on and you're seeing posts from your friends. It's okay. I guess that's relevant if I'm in college because I wonder what my friends are up to this weekend. But over time, that doesn't scale. Over time, that becomes weird when your angry uncle is posting about Trump and you're just like, okay, this isn't for me. Long story short, I think that social networks need to become less social. And I think that something that will make up for it is this idea of learned association or learned affinity through your behavior. And I hope what we will be able to do is show that algorithms can be used to work for the user rather than for the company. And that will end up being a great experience long term. There are all sorts of things you have to watch out for in this direction.

• 30:59Speaker 00

  The same way there are things to watch out for in social networks around filter bubbles and around some user having way too much distribution and using that distribution to post things that aren't true. Or there are all sorts of issues you have to work through. It's not squeaky clean, but it is very exciting because every network is moving this way. But it feels like when networks were moving to mobile in 2007, 2008, they half stepped. Remember, Facebook had a mobile app that was like actually written in HTML and wasn't really native. And then all these native apps came out doing social networks. I was like, oh, that's what this should be. I feel like machine learning is exactly the same wave we're seeing right now. It's a parallel wave.

• 31:38Speaker 00

  I don't think it's a complete annihilation of the social network, but I do believe that unconnected content is incredibly important.

• 31:45Speaker 02

  Mike, I think what doesn't go away is the desire to talk about it with people you care about when there is a connection. I think inverting the discovery versus sort of conversation piece is really key. What determines what an artifact or other things that are recommendation driven is not who you're friends with or who you happen to follow or who you knew in college. It's what we think is relevant to you. But sure, I'm really interested in housing policy in California. Whenever I get a great housing policy article, like instantly I have a housing policy group in the DM chat. But even For the people that aren't in the social area of the product yet, we've seen people sharing it out to Twitter to start a conversation or sharing it to a WhatsApp group and have a conversation. It can build relationships and strengthen them once you have more things to talk about. And then I have a friend, we're both really into the Warriors.

• 32:29Speaker 02

  And pretty much once a day, something will come through my feed that's about some either Warriors rumor or story. And it's like another moment to have another conversation with him. The social component sells a very strong conversational piece. It just doesn't need to gate discovery as it has traditionally.

• 32:44Harry Stebbings?

  Kind of a slightly weird one, guys, but I just did a next generation kind of consumer social network in Europe, positive only, kind of gasp for Europe if we're just being blunt. And everyone was like, oh, anyone can just copy them. Anyone can just copy them. Where's the defensibility? When you think about social and feature richness, is there anything wrong with copying?

• 33:04Speaker 00

  I was gonna say, one of the questions you had sent over earlier was like, man, is it, do you just, and actually, no, you said social. You were even nicer. Isn't social like a bad place to invest right now? There hasn't been a new social thing, really. What did you say, in the last 10 years, maybe? Yeah, yeah. I said it was be real, but I don't know. I saw some headline this morning on Artifact about how like, be reals are down 95% or whatever. And I guess social gets a bad rap. This is gonna be heresy to a VC's ears. But I think investing in verticals and spaces is BS. Yes, in general, generative AI is gonna produce something pretty cool. Yes, these verticalized, like the sharing economy, it's like, okay, cool. That was a while ago, but I'm just naming these trends that have come and gone throughout the years.

• 33:48Speaker 00

  100% of this is team, 100%. You can take a team of people and say, hey, go build a new car company. And you're like, ugh, cars. But I don't know, with the right team, with Elon in charge, it could be worth a lot. Cars are inherently unsexy as a business, and I guess the last chapter hasn't been written on that valuation. My point is, I think almost everything here is about team plus the area. And what's cool about news and social is the general, let's talk social for a second, the general lack of the skills that it takes to grow social things. The one thing That I think Facebook should be remembered for as a professional development like incubator

• 34:30Speaker 00

  is its ability to teach young PMs the scientific method of growth. How do you grow things? Maybe to a fault, by the way, with some of the tactics. But using the scientific methods, run A B tests or multivariate tests, using statistical power, using p-values to understand whether or not you have significance in a test and whether you can loop your way towards better things in social. Man, that is so important and it is so hard to just get a group of people together and get lucky like we did with Instagram because we had no insight into any of that until we got to Facebook. My point here is that with the right team and the right skills and the right history, you can make pretty quote unquote unsexy areas become sexy again.

• 35:14Speaker 00

  I can't tell you how many people when we started Instagram were like, images, whoa. There's this famous graphic at the time that had money amount in exits in video versus versus photos. And it was, you had this huge YouTube one and then nothing in photos. It's like, okay, you can either read that as that is a pattern and that you can extrapolate that, or you can say there's the opportunity.

• 35:34Harry Stebbings?

  I'm sure you had Flickr in that bucket, which is like the one thing. But my question to you is, I always say the same. I'm a VC in every single LP. You say about questions, everyone wants to know about Instagram and you ask them all the time. Every single LP, where are you specialized? Where are you specialized? I always say the same as you, but then VCs who are specialized say, yes, but because I only do this, my ability to detect greatness in data, in founders, in founder mentality is so much superior that I have better detection skills. And you guys want me as your investor because I absolutely know about the movement from the social graph to content discovery. I know everyone in ML, in all of the incumbents. I'm a better partner to you because of that specialization.

• 36:19Harry Stebbings?

  Fuck, I'm really selling a specialization. That's the pushback. Is that fair or are you still, come on BS?

• 36:24Speaker 00

  If there was a VC that was simply focused on discovering amazing talent rather than special ideas or special verticals, I often think you should ask. Steve Anderson this was the test. Hey, I'll give you 50K for this company. If you can find a technical co-founder. Was that him being like, you need someone technical. So yeah, that derisks the idea. Or was it a test of can you attract the right person? Can you team build? And is this person good? Can you find a really good person as your first hire? And I got really lucky finding Mike in that coffee shop that day. And then the fact that Mike didn't go running for the hills when I told him about the company we were building and he was excited. I'm not putting it all on me because of course Mike helped build the company from the beginning as well.

• 37:08Speaker 00

  But I do think there's a, an important quality in early teams, which is can you form a great team? It's why you see so many ex Stripe people who are fantastic. Go off and start their own companies or ex PayPal people. Like I often say to Mike when we're hiring or firing, do you feel like this person? Three years from now can go start a great company or go be the CTO or COO somewhere? And if that's not true, why are they here? And that's just the common element with every great team from the beginning is they attract that group of people.

• 37:38Harry Stebbings?

  When you guys started, there wasn't a queue of the best engineers. Hey, we'll join your new startup. And now obviously literally everyone in tech will want to join Artifact. My question to you is, how do you deal with hiring and adding to the team with the sheer volume of applicants in Canvas? That would want to join and how does your candidate acceptance process change?

• 37:59Speaker 02

  I think pre-launch, it's funny because amazingly the beta was really quiet. People signed an NDA, but it's only as good as the person decides it to be. So it was really quiet, which actually meant that recruiting wise, we leaned on our current network. That is pros and cons. I think there are wonderful people that we worked with at Instagram. And it's really different in the startup. There's high variance of outcome and there's time that it takes to get there. I honestly just in full transparency, still learning to screen for is the people that will thrive in that environment. Or at least tolerated enough to get to the other side versus wanting the solution or wanting the fallback. We did a six month performance cycles at Facebook, at least they were when we were there. I think they've changed this a little bit. We're on six month increments. People would sometimes be like, I'm signing up for a six month project. If it doesn't work out, I can apply for a transfer.

• 38:44Speaker 02

  This is really different. We're in this together and we're in this for the long run. I think we're learning still about what it's like to have that conversation upfront and to have people join for that reason. And then the other piece too, and this is a skill that I learned the first time around at Instagram, is tailoring the solution to the problem space. There are ways in which building for an Instagram, not just from a community sized perspective, or from a team sized perspective, are so different from our team has seven people. We're just getting started. There's pieces of process or technology that are the right thing for your multi-office 2000 engineer team that would just not feel right here. So it's about right sizing and honestly, even for ourselves, taking what you know, which is all of the accumulated bits of knowledge,

• 39:26Speaker 02

  both on team growth and on the technology engineering side, and filtering it through, is it right for our stage? Is it right for where we are? And can we take the best of that without all of a sudden acting like we are a team that is either much further along on the journey than we are? And we tried running an A B test on our beta group and then two weeks later, we like let it run and we did all the math and we're like, to detect a statsig difference in this beta group, you would have had to basically make the feature twice as good effectively. There's very few things that you're going to ever test that are that good. When we launched Explore and made it personalized rather than just like most popular photos, like that was a 2X delta in usage. There's very few of them, stories equivalent. So it's actually been really fun to now be public and we ran our first test and actually got statsig results.

• 40:10Speaker 02

  We're like, okay, we have to remind ourselves like what tools and techniques from this toolkit that we built up are right for where we are now. And that's the question we'll always have to ask and it's about going on that journey with our team too.

• 40:19Harry Stebbings?

  Can I ask final one and then I promise we'll do a quick fire. The hardest thing for me in adding to team is trust. You have to trust people. It's like pre-seed investing as well. You both sound smart. You're both great people. I don't know if like you, you trust someone straight off the bat and you met them once. Am I ready to give you a job or 500K? No. So how do you accelerate the trust building process when adding to the team? When working with someone, it could be an investor, how do you advise me actually struggling to hire because of the lack of trust?

• 40:48Speaker 00

  I think your, your premise is wrong though. I think that of course, if you're going to get married to someone, if you're going Help start a co-founding relationship. You can't fly through co-founders. I guess maybe some people do. I think the premise or the constraint that you have to 100% trust every single person. It's just not right. I also think it's right, like in hiring, you just need to hire a bunch of people and realize your hit rate's not going to be 100%. That's okay. This isn't a forever thing. Who holds a job forever? No one, very few people. And instead, just optimize for minimizing the chance of getting it wrong, subject to moving quickly enough. And if it's wrong, move really fucking quickly about making the change.

• 41:30Speaker 00

  And I think actually that last part is the part people have the most problem with, not actually trusting people. It's when it's not working, moving quickly, because it's so hard to screen at a few interviews in a coffee or whatever, whether or not you can trust someone for life or whether they're the right person for this chapter of the company. It's just not possible. So you've just got to move on it with the best of intentions on both sides and move really quickly if it's not working. Did you move quickly when it wasn't working? I certainly tried a bunch of times, which I think there are probably like three examples in the last year and a half I can name where that happened, yes. And then there were times where we didn't, or I didn't, and I think we regretted that. It's just a lesson you're learning over and over again, running a company.

• 42:14Speaker 00

  You need to be a compassionate leader. You need the right person in the right spot and you need to help them be great. And if it's not the right fit, for whatever reason, you move on it. I think that's something a second time founder will do that a first time founder has a lot of trouble doing.

• 42:28Speaker 02

  You have to go against basic human psychology and empathy because you think like your first instinct maybe is a first time founder's, oh, the compassionate thing is even though it's not working, we'll try to make it work and have the fifth conversation. And then the second time you're like, maybe the empathetic thing is realize when it's not working and make that move.

• 42:43Speaker 00

  Can I talk about music for a second? Because I have to bring it in, I can't. I heard this thing on NPR this morning. It was so fascinating. I have to find this paper. But there were these researchers, this is one of these tough pieces that NPR throws in the middle of their morning show. But it was actually super interesting about how basically these researchers figured out how much of a clip of a song they have to play you before you can form a very strong Opinion of whether you hate it or love it. They found that the shortest they could do was five seconds, but I'm going to quote this wrong and I need to actually find this paper. But it seemed like to me the difference between five and 10 and 30 seconds was very small. All you need is five seconds and you're like, I got it. This is great or I got it. This is not great. In general, with talent, you can tell very quickly in a working scenario,

• 43:26Speaker 00

  whether someone generally is going to work or isn't going to work. There's that middle ground where you don't know, but in a small startup, I feel like it's fairly short. Just getting a better spidey sense for detecting that in the hiring process is what keeps you from having all this pain of churn throughout time. Isn't it like Kahneman and in general, your goal as a founder is to figure out how quickly you can detect whether or not someone's going to work in a role without having hired them yet to save them the pain and you the pain of having to make a hard change. But then being a founder, making the hard change, even though it's painful.

• 44:01Harry Stebbings?

  How important is fun? This is not between us, but I hope they don't listen. I'm hiring a videographer and I met someone recently to totally obfuscate it. They were just boring. They're capable of touring them. I've trialed them. They can do the work, but they are boring. They are not fun. They are so quiet. They're not bad.

• 44:22Speaker 00

  Harry, sometimes that's a feature, not a bug. Sometimes you want like someone who's not highly volatile, cracking jokes all the time. It just depends what you want. I don't know, like in your scenario, if you have to spend a bunch of time with them, travel with them in a small office, then I guess personal chemistry really matters. But Mike, we've worked with plenty of people where we didn't have personal chemistry, but they were great at what they did. And that's fine. And in fact, as a small company, one of our mistakes in Instagram is hiring too many mission hipsters that wore plaid and really liked drinking bourbon. That was stupid. We should have just been hiring the greatest people out there. I think it depends on the size of team and the dynamic. I don't think being a fun person should be a requirement for a job. I think it's okay to be boring. Mike, do you agree or I like?

• 45:05Speaker 02

  Yeah, I think it goes, it comes down. So you kind of want the team composition to have at least a sizable group of people where you draw energy from them. I think if your whole team is made up of people, you're like, Yeah, they're fine, but like they're good at their jobs, but they're not like sparking energy. I think your own day to day is not going to be exciting, but I don't think that has to be everybody. And I think, I think you can find that balance around. Some people are quietly executing and doing that, and they're probably not going to bring you an idea that's going to blow your mind, but they're executing really well in the things that they're doing. I would just be wary of an entire team of that would probably be not super fun to work with.

• 45:34Harry Stebbings?

  Would you ever hire a brilliant prick?

• 45:37Speaker 00

  No, in fact, we have throughout our careers, 100% and it's the worst.

• 45:42Speaker 02

  Yeah.

• 45:42Harry Stebbings?

  My, this is what Kevin was saying before you joined. It was a bit awkward, but. And then for us, okay, final one. Would you have incredibly ambitious and hungry or like super experienced IQ or hungry hustler ambitious?

• 45:55Speaker 02

  I think the different phases of the company require different kind of people. I've always been happy with people who have the sort of raw talent and desire to learn and don't see boundaries as a reason to stop working on something. That's a repeated theme. The people I love working with are the ones that don't come up if they're iOS engineers and they start having to do backend work. They don't throw up their hands and go, ah, that's not my problem. Please help me here. It's the people that you're like, you know what? And like one of our engineers was like, oh, I haven't really done marketing stuff before, but somebody needs to put together our Google Play Store page. I'm going to go learn what other companies are doing. I'm going to put together a proposal like that desire to not see your role as strictly defined by like the four bullet points that you think you do. That's to me, the kind of people I've repeated working with now.

• 46:37Speaker 02

  Once you scale, there's sometimes reasons why there are boundaries between teams. There's more process. You wouldn't want your excellent mobile engineer to be like, you know what? I rethought how we should do our scaling when you're like serving over a billion people. So you start creating more of that, but especially at our scale. And honestly, for the next few years, it's raw talent, ability to learn quickly, ability not to find themselves strictly by the role that they were brought in to do. And that leads you out. But if you have only that and you don't have any people who have expertise, it can also lead you down this other side of things where you're like, just being enthusiastic about an area isn't necessarily going to determine that you're going to be able to be good at it. So it's that community of expertise, interest and selflessness is the kind of core combination that I seek.

• 47:18Harry Stebbings?

  After hearing your comments on Brilliant Prick, I now know why you didn't offer me a job. But all good. Thank you. I could talk to you guys all day, but I want to do a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay? Sounds great. Okay, so this one's for both of you. How did having children change how you think and operate?

• 47:34Speaker 02

  Definitely more breaks throughout the day and more thinking about what am I building for on a 20-year horizon and less sleep.

• 47:42Harry Stebbings?

  Kevin?

• 47:42Speaker 00

  Prioritization, only doing the shit that matters because you're probably going to get cut off in the middle of doing it anyway. So reporters in the old days, you'd like, you have to write the most important stuff in the first paragraph because it might get cut off. It's basically doing that in life because you might get cut off. So my son last week was running around, I was in the middle of something super important and he just fell and busted open his chin and needed to go to get stitches. And he's fine now, he got three stitches, but my entire day got just because I had to go do the stitches, deal with everything, prioritization.

• 48:14Harry Stebbings?

  Mike, what's the one word that will be on your tombstone?

• 48:17Speaker 02

  Ooh, hopefully curious.

• 48:18Harry Stebbings?

  Kevin, what will be on yours?

• 48:20Speaker 00

  Always learning.

• 48:21Harry Stebbings?

  Kevin, this one's from Clark. Do startups still do best when started in SF?

• 48:25Speaker 00

  Yes, and he and I have had lots of arguments about this. It's gotten to the point where it's not fun to have the argument with Dave anymore about Ben's son. But he doesn't live in SF, so of course he feels that way. And I live in SF, so of course I feel that way. I think San Francisco has been through so many downturns. And if you look at this one alone, you can draw the line down and say everything's going to just shrink. But it has been through so much and always rebounds and comes back way harder than it was before, in a good way.

• 48:58Harry Stebbings?

  Have you ever had this much excess in terms of tax revenue? Because that cash is king and there's so much cash that's left and it's not coming back, or it may not come back.

• 49:06Speaker 00

  That was true with every single downturn though. I think the best universities in the world generally for computer science are in this area. People passionate and making next generation AI algorithms and stuff are all from this area. They all mix together. Literally everything interesting is happening right here. I guess if you consider Bitcoin and crypto super interesting, I guess you can bet on Miami. But I'm going to bet on the next chapter of companies starting their core here. Though I will say the biggest difference going forward, you're going to see huge remote component, especially for your most talented people. They'll be able to work basically from anywhere. And I think that is a fundamental difference, but there's no way San Francisco is going away as a city. It's like the center of great startups.

• 49:48Speaker 00

  Basically, bottom line is that I think it's easy to be anti San Francisco right now. But mark my words, look back five years from now and you're even seeing the glimmers of it now, just all these companies getting started. If you look at history, what is it? It never repeats perfectly, but it rhymes. And it's just, there's not a single time where San Francisco hasn't come back with a vengeance. Boom and bust periods. There are cities in the US where fundamental changes have happened to their industries and the cities have gone away, Detroit being one of them. Prior exists for that being true. I cannot make the same parallels today for remote work or any of the shifts that have happened during the pandemic, that you're going to see that fundamental shift to the community here, which is nerds.

• 50:32Speaker 00

  It's foggy, it's cold, you get to work hard, there are no distractions. We only have three restaurants that stay open past 11. I think there's one club in the city. There's literally nothing fun to do past 9pm in the city. So people work their butts off. And I think it's a great center of that. It's the kingdom of nerds and I love it.

• 50:52Harry Stebbings?

  You literally have dinner at 6pm. It's bizarre. It's a fix.

• 50:55Speaker 00

  Yeah, it turns out it's a lot like what having kids is. You have dinner at 6pm.

• 51:01Harry Stebbings?

  You get up at 5am.

• 51:03Speaker 00

  Exactly.

• 51:04Harry Stebbings?

  You're better than nine. Anyway, Mike, what do you believe that many disagree with?

• 51:08Speaker 02

  The SF thing is one. He stayed here and doubled down on San Francisco. Goes back to the brilliant jerk thing, like that you can tolerate some amount of the wrong person, but right for the job and it will get you further along. I keep learning this lesson, it doesn't work. And you need to cut that off and you might move slowly in that first week or two and then you'll go forward and then you'll build from there. The other one is, and it's ironic as a second time founder, is that past success is a prediction of future. Like you have to work even harder. You have to be just as thoughtful about the team. You have to work to both. By your own bias, I've done this before. No, you earned yourself the right to be in the conversation. It doesn't predict anything about how well you'll succeed.

• 51:45Harry Stebbings?

  Kevin, if you could tell yourself, 20-year-old self this is, one thing, what would it be?

• 51:50Speaker 00

  Probably not to worry as much, but that's easy to say when that thing's worked out.

• 51:54Harry Stebbings?

  It's so funny. I've asked quite a few people this and they all say that. And I put it once on Twitter and they were like, Harry, you literally only interview people who make billion-dollar companies. I'm like, ah, good point. It's not me.

• 52:04Speaker 00

  Yeah, but I'll challenge that with, I'm saying that with the lens of seeing my friends who haven't had billion-dollar exits, who are perfectly happy with their families, growing them, maybe not in downtown San Francisco and a high-rise or whatever. But actually, the thing that matters most is that you meet a partner or a group of friends that carry you throughout life and then you grow a family or you choose to live the life you want to live. And I see people who are VCs for a little bit, they make $5 million and they retire at the Sierra Nevada and they buy a huge plot of land and they live like kings and they're super happy. I just don't actually see a meaningful difference in happiness between any of these people as long as you're just enjoying your life and doing what you love.

• 52:47Speaker 00

  So forget about the outcome. I don't think people should worry so much. That being said, there's a lot to worry about to get to the level of being okay. So I want to be clear, there are a lot of people in the world that like work three jobs to support a large family and I get why people worry. My point is, if you're 20 years old and you're working hard, you don't have to worry, are you going to become director by three years from now? Are you going to be on the cover of Forbes? None of that stuff matters. So I just, I think worrying a little bit less, there's this great article that I was served on Artifact yesterday about doing things that are a little bit more irrational, a little bit more often. And I agree with that. Just don't always do the thing that makes complete financial sense or complete career sense. Be a little bit random. And actually, machine learning would tell us that,

• 53:31Speaker 00

  which is that being a little random on the margin is actually optimal in the long run. So have fun, be a little random.

• 53:37Harry Stebbings?

  Do you find it hard to trust new friends? You're Kevin and Mike, founders of Instagram. I'm not being rude. You're financially very successful. There's reasons people want to be friends with you. There's reasons VCs want to be friends with me.

• 53:48Speaker 02

  Harry, Harry, what are new friends? I'm sorry, but if you're a parent, I feel like I get told this, the first five years of your kid's life, it's just literally everything else goes away. And you're just like changing diapers, going to the hospital, giving drugs, waking up at 4am. What are new friends, Harry? I like, I'm excited for the moment where I come up for air and you start hanging out with people again. Please tell me what that's like.

• 54:13Harry Stebbings?

  All right, an ultimate one that's open, but I'm interested. You guys have done the most incredible angel portfolio and investments. Any big lessons from doing that?

• 54:20Speaker 02

  If it feels hypey, if there's at all a glimmer of like, I don't love this area, but lots of people are excited about. Man, I looked back, I did a little reflection, it was like mid last year, I was like, there were like a few either LP positions I took or individual investments. I was like, man, I did this because it felt like this was a thing a lot of people were excited about. And I wasn't, I have to keep relearning that lesson. My life is relearning lessons, I think everybody's is, and hopefully you get better on margin, making fewer of the same mistakes over and over again. So that's a really big one. And two, it's such a cliche, but there's the founders where you're like, they were going to run through the wall of any problem that they hit. And then the ones that are like, oh, actually they're really polished and they came out of a Facebook or an Instagram and they've got like a decent first demo.

• 55:03Speaker 02

  But you ask yourself, the second something goes wrong here, are they the kind of person that are going to be able to make the hard decisions and move quickly? Like, have they had that adversity in their careers? And/or can you imagine themselves in that adversarial situation? And again, I look back and again, so much of this is hindsight thinking, so you can learn the lessons you want to learn and then try to adapt them for the next round. And we've been investing way less now that we've been super busy with Artifact, but yeah.

• 55:25Harry Stebbings?

  I think this is millennials, I am a millennial, but they're just soft. And when it gets hard, they stop Facebook and earn half a million dollars. I've had three companies, right, it gets hard and they're like, I'm off Facebook, I'm as a PM and it's.

• 55:37Speaker 02

  Harry, I had someone leave Artifact a while ago and the reason was I feel like I'm being told to do my homework before I can play. And I was like, hold on here.

• 55:49Speaker 00

  Of all the things that have literally ever been said to me in my career, that was, that tops the charts of millennial.

• 55:55Harry Stebbings?

  To analyze that, what did you fuck up in that? I didn't mean like in the hiring process, did you not misread?

• 56:00Speaker 00

  I'm laughing about the statement only because to me, it seems so out there culturally. When you join a company that I literally spend my day working, I don't get to play. I wish I could play. I don't get to play. Who gets to play? But actually I realized in the hindsight, it's a totally fair comment because there actually are lots of companies that pay millions of dollars to play because on the off chance that one of those playful ideas becomes the next big thing, they're willing to spend that. But at a startup, you can't. There's no playing. You work hard every single day to get stuff out. But I will tell you, it's changed so much and, but I feel like every generation has complaints about next generation. So I think it's a bit trite to have a complaint like that, but you just, you gotta, you gotta screen for people.

• 56:44Harry Stebbings?

  It is tech, NPE, Helman Freeman, Apollo, these still fall asleep at their desks. I want them. Where are them? Tech, play with Lego before they work.

• 56:54Speaker 00

  And it can't be about what espresso machine you have in the office and what perks you have. And those things are all fun, but there's that famous wartime general, peacetime general thing. Man, this stuff's just hard and that's why the startup process just chews up and spits out people. No process I've seen before. It is just a grinder. It goes through people like crazy because it either screens you out because it's too hard work wise. The trade offs are too crazy or the volatility and the emotions are too much. The volatility and the like, we're going to succeed. Oh, we're going to fail. Oh, we're going to succeed. Oh, we're going to fail and not knowing what is true. That volatility can kill people. We can just chew them out and spit them out.

• 57:34Speaker 00

  You need to be okay with the fact that this stuff happens, but Mike and I have the like amazing advantage of literally having thought this way before and just knowing there's this thing in flying. I learned to fly after leaving Instagram, but just trust the instruments. If it says you're sinking, don't think about how you feel because you're going to feel you're like you're leaning left or you're rising or you're falling. Have you ever been in a plane with the window down and you feel something? Thing you're like, ew, that feels weird. Just trust the instruments. My God, we have instruments, dashboards, et cetera. Just trust the instruments. Forget about what people are saying. Forget about what issue you had yesterday with the server. Trust the instruments. It doesn't make it any easier. You're looking at it and you're like, Mike, let's trust the instruments. You're like, I don't want it. It doesn't feel good.

• 58:18Speaker 00

  But if you just learn to trust the instruments, you'll be okay.

• 58:20Harry Stebbings?

  Analyzing my love life, I don't trust my.

• 58:25Harry Stebbings?

  I am but for the bull market means that actually tech was get rich quick and man that people could survive in startups. They were cushy. They were shit.

• 58:33Speaker 00

  And so. Mike Maples has the best term for this. He calls them ZIFs, zero interest founders, and I love it. But zero interest founders, it's amazing. It's like you've only experienced life in the zero interest market environment. Everything's free, capital is flowing, everything's great. Man, there's a reason why people who have seen things in history do better than those who are seeing things for the first time. Cause you start to learn there are patterns and accesses. Mike, you were like, oh, if I've done investments that feel trendy or hip, and I was like, literally every VC's crypto portfolio, literally all of them. People were like, I don't know, but it's blockchain, so I'm going to throw money at it. And it turns out that some companies might actually succeed and do very well in that category.

• 59:12Speaker 00

  But you need to be careful about one, riding these trends and two, just extrapolating the present. Because zero interest doesn't last forever. And then all of a sudden, musical chairs, like music's over, take your seat. There's not one left for you. But that's why having this advantage of being through these cycles before it helps. But man, you make the same mistake over and over again, even though you've been through it before. But you just, you're quicker to fix it because you know you're making a mistake.

• 59:38Harry Stebbings?

  Mike, how do you know when Kevin's middle aged? When he goes espresso machines? That's all fun stuff.

• 59:45Speaker 00

  He's like, well, I did a espresso machine on our first Instagram office. That was the first big purchase I made. Remember, Mike?

• 59:52Speaker 02

  Absolutely. We had it in there. We had a copy. He taught us how to pull a good espresso shot.

• 59:56Speaker 00

  So important is in remote work.

• 59:57Harry Stebbings?

  I love that. Listen, guys, final one, because I've taken up so much of your time. Next five years for you with Artifact. If we do this in 2028, what do you want Artifact to be?

• 1:00:05Speaker 02

  I would love for it to be among a portfolio of products solving fundamental question of how do we help technology serve you and tailored to you and make sense of the craziness of the world and the complexity of the world in a way that makes things feel fun and simple and tailor made.

• 1:00:23Speaker 00

  I'm going to only talk about Artifact and forget about all the other stuff that I want to do because Mike just covered it. For Artifact specifically, I want a world where publishers trust technology companies, or at least this technology company, where there's a partnership where it's, I'm going to say win-win is a cheesy term, but where we build something great and we're able to support the publishing industry, but also maybe spawn an entire generation of independent publishers and give them access to a large audience and to publish to a world that they wouldn't have been able to publish to otherwise. And we create a system where people look at algorithms and portraits and all this stuff, not with a skeptical

• 1:01:03Speaker 00

  eye, but with excitement, and they see what it can do for them. But man, if there were two rivers to swim hard against, it would be trusting algorithms and the news industry, just like all the challenges. But you don't take on small challenges when you're a second time founder. So I'm excited to go after it. And I think it'll take at least five years to get even close to that point.

• 1:01:23Harry Stebbings?

  Guys, honestly, I'm sorry because you saw the schedule and you were like, what the fuck, Harry? That was nothing to do with it. That's why I love this. Thank you both for being so great. I honestly so appreciate it and thank you so much for joining me.

• 1:01:36Speaker 02

  That's the last thing was Faber.

• 1:01:40Harry Stebbings?

  I love the way that conversation evolved. That was completely unscripted, unplanned. I want to say a huge thank you to Kevin and Mike for being so flexible with the schedule there. If you want to see more from us, of course, you can on YouTube by searching for 20VC. But before we leave you today, Secureframe is the leading all-in-one platform for automated security and privacy compliance. Secureframe simplifies and streamlines the process. of getting and staying compliant to the most rigorous global privacy and security standards like SOC 2, ISO 2701, HIPAA, GDPR and others. Secureframe's industry-leading compliance automation platform, paired with their in-house compliance experts and former auditors, helps you get audit-ready in weeks, not months, so you can close more deals faster.

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• 1:04:31Harry Stebbings?

  As always, I so appreciate all your support and I can't wait to bring you an incredible episode this coming Friday with Joey Levin, CEO at IAC.