Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934

1. 0:00 – 3:25

   Kevin’s Background

   1. HSHarry Stebbings0:00

      (beeping) Three, two, one, zero. You have now arrived at your destination. Kevin, this is such a joy to do. I've wanted to do this one for a while. I've heard so many good things, largely from a slightly biased person, being your wonderful wife, Elizabeth.

   2. KWKevin Weil0:16

      (laughs)

   3. HSHarry Stebbings0:16

      But thank you so much for joining me today, Kevin.

   4. KWKevin Weil0:19

      Thank you so much for having me.

   5. HSHarry Stebbings0:21

      Not at all. I'm excited for this. But I wanna start, when we see this kind of incredible, illustrious career. We've got Instagram, we've got Twitter, we've got Planet most recently. So, how did you make your way into the world of startups and to lead some of the most powerful product talks as you have done?

   6. KWKevin Weil0:37

      So, completely unintentionally is the answer. Um, I- I was... It's funny, I was actually... I was at Harvard when Zuck was at Harvard, so, uh, I'm a year older than him. And I went through school planning to do... I wanted to be a math professor or a physics professor. I was just like, you know, total tunnel vision on math and physics and science. Zuck, after I think a year or two or something, dropped out and went, uh, went to Palo Alto to do Facebook full time. And I remember thinking, you know, after- after Facebook had just taken over the campus, right? You remember back then, it was taking over every college campus one by one.

   7. HSHarry Stebbings1:12

      Yeah.

   8. KWKevin Weil1:12

      And I remember thinking, "He's gonna drop out of a Harvard education to go do some company? What an idiot." You know, and like... (laughs)

   9. HSHarry Stebbings1:22

      (laughs)

   10. KWKevin Weil1:22

       So I just had no conception, right? And then, uh, and I- I... So I came out to the Bay Area to continue a physics degree, and ended up meeting, uh, my now wife, Elizabeth. And she opened my eyes to the fact that you-ou j... We were just surrounded by all these startups doing amazing things. And at some point in there, I finally was like, "Wait a minute. I'm doing, you know, theoretical physics. If I'm lucky, I'll make an impact on physics in like 40 years, if I'm lucky. And I could go write code and like ship something at one of these companies, you know, tomorrow, to a million people. I wanna go do that." And so, uh, really, thanks to her and, you know, as w- if we talk about my career, we'll- we'll realize that almost all of my opportunities came from Elizabeth. I really just ride her coattails. Um, but that's how I got started. I hopped out of my PhD, I dropped out and, um, started working at startups as an engineer. Um, ended up at Twitter in the early days when it was about 40 people. Got really lucky, people took some bets on me that they really had no business taking. And, uh, I worked hard, tried to make those bets real. Ended up leading product at Twitter after about seven years. You know, then went to Instagram to lead product. Um, now at Planet. So, it's- it's been a wild ride. It has absolutely not been premeditated. (laughs)

   11. HSHarry Stebbings2:38

       Well, I mean, there's many things I love there. One, "Zuck, he dropped out, what an idiot." And two, I did actually hear, um, that, you know, your jobs are all thanks to Elizabeth. So, uh, don't worry, it was someone else who told me that as well.

   12. KWKevin Weil2:50

       (laughs)

   13. HSHarry Stebbings2:50

       Um, it was validated by a third party. Uh-

   14. KWKevin Weil2:51

       Well, it couldn't possibly be Elizabeth, could it? (laughs)

   15. HSHarry Stebbings2:54

       It- Well, it couldn't possibly, no idea what you're talking about. But I did speak to another third party. We mentioned, uh, Instagram there as part of the journey. Uh, I was intrigued, I spoke to James Everingham, and he told me that Instagram is one of the best product thinking organizations he's ever seen. And I thought, "Huh, that's interesting." What do you think, Kevin, makes Instagram this way specifically? And I guess what are one or two of your biggest takeaways from leading product at Instagram?

   16. KWKevin Weil3:21

       So when I was leaving Twitter after about seven years there, it wasn't the

2. 3:25 – 6:19

   What makes Instagram’s product so good?

   1. KWKevin Weil3:25

      first company I'd ever been at, but it was the first company I'd ever been at where it was at all successful and I had any degree of responsibility. And, uh, somebody I c- considered a mentor told me, "You know, you've been at Twitter for seven years now. You don't know the difference between the way Twitter does something and the right way to do something. And they're not always different, but they're not always the same. And, like, the important thing is being able to tell them apart versus just knowing one way to do something." Um, and so this person was like, "You need to go somewhere else. You need to learn different ways of doing things so that you get an appreciation for- for all that." And it was so right. So, I give- I give Kevin Systrom and- and Mike Krieger, the two Instagram founders, just a ton of credit for, um, for the way Instagram works and- and how product focused it was. I'd say a couple things stand out from working with Kevin. Um, number one, he's the best editor I've ever seen. He spent a ton of time just like distilling things down, taking an idea, sanding off all of the rough edges, thinking about how something new should integrate into Instagram's product, and not stopping until it was so beautifully integrated it felt like it was always a part of Instagram. You can just like... I- if you think back to the Instagram of 2018, you could feel that. Every single detail was designed, even when, you know, new formats that made big changes to the product, like stories, came in. And then, uh, the other big thing that, uh, that I learned from Kevin is that conviction and decision making really matters. So, like, we were- we were very hypothesis driven at Instagram. We were always focused on the problem we were solving and like the why behind it. The- the worst thing you could possibly do is go to Kevin Systrom and say, "Hey, I had an idea. Wouldn't it be cool if..." And he would come back and he would say, "No, it would not be cool if... What problem are you solving? Who are you solving it for?" Um, so there's this whole like fascinating backstory to the development of IG stories which, you know, is probably for a different podcast. Um, but, uh, as- as we were developing it and going through, Kevin said to the entire team, "Whatever we build here, this is gonna go at the top of Instagram's main tab. That's final. That's a decision. I know it's a risk, but- but making the move to Instagram stories, making the move from an Instagram where people only put their most perfect, you know, curated stuff to a world where they feel comfortable sharing their like funny, silly, daily moments, that's existential for us. We know it's solving a main problem for users. And if we don't get it right on this first iteration, we're gonna roll forward. We're not rolling it back."... so it's gonna go front and center on the main tab. This is the bet we're making. Now, let's go build the best product we can. And-

   2. HSHarry Stebbings6:11

      Kevin, the joy-

   3. KWKevin Weil6:12

      ... i- it-

   4. HSHarry Stebbings6:12

      D- I'm sorry, I have to dive in here. Sorry. You mentioned conviction, and decision-making, and then Stories, and the backdrop of Stories.

3. 6:19 – 8:09

   Was IG stories a reactive move to Snapchat?

   1. HSHarry Stebbings6:19

      From the outside, and maybe this is naive, it looked like a reactive move from, like, towards Snapchat's, obviously, Stories, which was phenomenally successful, like, t- is that true? If so, is that kind of conviction in decision-making 'cause it's a reactive move based on a competitor? Like, and what's the backstory there? I'm, I'm intrigued you mentioned it.

   2. KWKevin Weil6:40

      Yeah. When we launched Stories, the number one thing we made sure to say was, like, "Kudos to Snapchat. You invented this format. Like, you found, uh, you, you highlighted a new way that people want to share, and they clearly wanna share this way." And it just showed that Instagram didn't have that way of sharing. I- Instagram had become really pressurized, right? Like, if you met a new person, you'd go to their Instagram profile to see what they were like and who they were, and that meant that, like, anything you posted to Instagram, you were like, "Is this how I wanna represent myself forever?"

   3. HSHarry Stebbings7:12

      Yeah.

   4. KWKevin Weil7:12

      And, you know, you get more followers and, and all of a sudden, like, you're, you're like, "Well, my last post got a hundred likes. Is this one gonna get a hundred likes? Ah, maybe it's not. Maybe I, maybe this isn't good enough to post on Instagram." You know? It, it was just slowly becoming more pressurized, and Snapchat helped us realize it. And so, for sure, in that sense, it was, it was a reaction to seeing that, like, people really wanted to share this way. But I think if you had just taken Stories and, like, plopped it in the middle of Instagram, it wouldn't have worked. Uh, and, you know, you've seen this as lots of other things, uh, lots of other, um, products have launched Stories, and they haven't worked. So, there was a real dissection of what made Stories work, uh, that... a- a- and then how exactly they should fit into Instagram and play with other parts of Instagram that I think was actually what made it successful.

   5. HSHarry Stebbings8:03

      What were they? What did Instagram do with Stories to make it successful in a way that others weren't able

4. 8:09 – 10:39

   Three Things IG did to Make Stories Successful

   1. HSHarry Stebbings8:09

      to?

   2. KWKevin Weil8:09

      So, there were three things, and let me see if I can remember them all 'cause it's been a few years. But there were three things that we, um, that were sort of key to Instagram that we just needed to flip on its head with Stories. So one was, um, one was that, the permanence, right? You, when you posted on Instagram, it was permanent. And, and that meant you really had to think about does this represent me and who I am? Uh, second was you got public feedback. So, uh, you got a hundred likes on your last post. Are you gonna get a hundred likes on this post? Like, if you don't, all of your friends are gonna see that it wasn't as popular. I- so, like, there's this public feedback that creates pressure. And then, uh, third, it's, it was a push model. So if you posted a bunch of times a day, you'd show up in your friends' feeds a bunch of times a day, whether or not they wanted to see all of your posts. And so, you know, you kinda... it felt a little thirsty for you to post a lot per day. So you, you wouldn't. You'd restrict yourself. You would only post, like, your best stuff.

   3. HSHarry Stebbings9:06

      Yeah.

   4. KWKevin Weil9:06

      And so Stories basically flipped that. It went from permanent to ephemeral. It went from public feedback to private feedback. And it went from a push model to a pull model, right? You click on my story. You decide you wanna see it, and then you, and then you see it. And so I can feel comfortable posting 19 things to my story because unless you care, you're not gonna look, right? And so Stories basically flipped all of those on their heads, and that was... as we understood that better, we were like, "Oh, that's how the pressure goes away." And, and then it was a matter of figuring out how to integrate it into Instagram in a way that felt great, so integrating it with DMs and all sorts of other, uh, aspects of the product.

   5. HSHarry Stebbings9:45

      I mean, I've never slid into anyone's DMs, so I wouldn't know what-

   6. KWKevin Weil9:48

      (laughs)

   7. HSHarry Stebbings9:48

      ... you're talking about. But (laughs) -

   8. KWKevin Weil9:49

      (laughs)

   9. HSHarry Stebbings9:51

      Um, but-

   10. KWKevin Weil9:51

       Yeah.

   11. HSHarry Stebbings9:52

       ... moving s- moving swiftly on.

   12. KWKevin Weil9:53

       But, but it was just such, it, it was such a lesson, just to, to wrap that up. It was such a lesson because Kevin was just like, "This is going at the top of the product, and it's gonna become central to Instagram, and we're gonna figure it out." And if, a- and because it did, it created network effects because everyone saw it. People started using it. And then when you saw your friends using it, then you would try it. If instead we'd done the timid thing and put it, like, in the back of a third tab, and like, "Well, if people find it, we'll do a 1% experiment, and maybe it'll work." Like, it never would've, it never would've taken off. And so it was, like, the boldness, the decisiveness. I, I learned a ton from that.

   13. HSHarry Stebbings10:30

       Can I ask i- does that, does that work when you're testing new products? And what I mean by that is, with the boldness and decisiveness, it goes against the gradual

5. 10:39 – 11:48

   Don’t be timid when testing new products

   1. HSHarry Stebbings10:39

      release, iteration, testing in Australia or in Sweden with new markets. It's a real clarity of conviction, here you are bold on my home screen, versus slowly getting enough data to know if it works.

   2. KWKevin Weil10:53

      Well, so this is one of my personal product beliefs. Testing doesn't mean, uh, timidity. You can always use the fact that you're testing something and you can run an AB test to test something 99% and have a 1% holdback. You don't have to test 1% in Australia, right? Testing gives you data. You can... if you believe in what you're doing, you can test by rolling it out to 99%. You can also test something aggressive, like putting Stories at the front of the, um, at, at the top of the user experience, and you can test that in Australia, but you don't have to test something on the third tab, you know, underneath a scroll. You can still test something really ambitious. So testing is a way to understand what you're building and how it's working for people, and that's orthogonal to whether what you're testing is bold or not.

   3. HSHarry Stebbings11:41

      Kevin, how do you know when to listen to users? You've worked on Twitter. You've worked on Instagram. You've worked on some of the most loved consumer products.

6. 11:48 – 14:13

   When to Listen to Users

   1. HSHarry Stebbings11:48

      When you make any changes, 99% of people say, "I hate it, I hate it," because they liked-

   2. KWKevin Weil11:52

      (laughs)

   3. HSHarry Stebbings11:52

      ... just what they knew before, and they're used to it. How do you know when to listen versus when to stick to the product strategy you have?

   4. KWKevin Weil12:02

      I don't think there's a science to it, to be honest. Um, it's funny. When I, when I introduce myself now to people, like, when I'm, uh, trying to make sure that they feel comfortable giving me feedback, I tell people, "Look, I'm really hard to offend. I want feedback. Trust me. I was head of product at Twitter. I built a product that..."... was the world's best amplifier for people to tell us how bad we were at building product. I'm really tough to offend now. Um, but, uh, I- I actually, I think, I always, despite having a... It's really important to have lots of data, 'cause data tells you important things. Um, there's no excuse for not knowing data. But I actually really think anecdotal feedback is valuable, uh, because a lot of times the anecdotes can get lost in the, um, in the data itself, especially when you're talking about a service that has hundreds of millions of users. Um, I always find anecdotes, especially the ones where you're like, "Oh, yeah, I've been kind of feeling the same thing," um, those play an important role. They make you ask questions. And ultimately, it's asking questions and developing hypotheses that lead you to better products.

   5. HSHarry Stebbings13:06

      Can I ask you a weird one? And totally off schedule, but I love this.

   6. KWKevin Weil13:10

      (laughs)

   7. HSHarry Stebbings13:10

      What makes a good anecdote versus a bad anecdote? And when you're training product teams today, how do you advise them on what good customer discovery is? What are good questions versus not good questions to ask?

   8. KWKevin Weil13:23

      Well, you have to go in, you can't, you can't go in with a hypothesis that you are trying to valid- like, that you, that you just want to see true, and so you ask leading questions. This is obvious, but people do it. Um, so I think it's a lot of the, um, it's the old, uh, was it Henry Ford or somebody is like-

   9. HSHarry Stebbings13:41

      Yeah.

   10. KWKevin Weil13:41

       ... "If you ask customers what you want, what they want, they'll tell you they want faster horses."

   11. HSHarry Stebbings13:45

       Yeah.

   12. KWKevin Weil13:45

       What you need to do is get a good, is do a good job getting underneath that question. What they actually want to do is get to where they're going faster. So, you, you hear what they say, but you really focus on what's underneath what they're saying. Um, and that, that's the way you get, that's the way you get, you do good product discovery.

   13. HSHarry Stebbings14:02

       I totally get you. Can I ask, we mentioned Stories being a massive success. If we think about mistakes, and your time back at Instagram, what was the biggest product mistake that you made,

7. 14:13 – 16:14

   Biggest Product Mistakes at Instagram

   1. HSHarry Stebbings14:13

      and what were your lessons and learnings from that experience?

   2. KWKevin Weil14:17

      So, let me... Uh, the, the, the most immediate one actually, when I think about mistakes, um, maybe more of a leadership mistake. I mean, there have been a number of failed product launches that we could talk about. But one of the, um, the, the biggest leadership mistakes I think I've made is, is not being decisive enough. Um, when I stepped into the, the leadership role at Twitter... So I, I, you know, spent seven years at Twitter, um, kind of growing from IC engineer, to ICPM, to manager, to director, to VP, to SVP. And at some point, most of that was leading ads products and on the revenue side. Uh, and then my last, I don't know, year and a half or something, I was leading all of the product, including the consumer products. And it was new for me. And we had all these amazing people on the team that had been working on consumer products for a long time. Frankly, half these people, I was like, "Man, I should be working for you, you shouldn't be working for me." And I was kind of intimidated, and there were 10 different directions that people's opinions on where they thought Twitter should go, and I wasn't decisive enough. I came in, I listened to everybody, everyone had different thoughts. And when we didn't agree, we kind of, like, would agree to meet next week and talk more about it. And one of the things I learned, and it was such a stark contrast going to Instagram, to the earlier part of the conversation, was like, "You know what? It's actually better, make a decision, launch something, realize that you got it wrong, fix it, and launch the next, the, the better version." And you're gonna do that faster than if you just sat and, like, talked in a circle for, you know, three months about theoretical things. So, just make decisions, go, and then fix it. Uh, a- and you're gonna mer- you're gonna work faster and you're gonna end up with a better product.

   3. HSHarry Stebbings16:05

      Can I ask, the challenge that you have is you are a product leader and you need to make decisions. And there is the edit button, there is also Twitter Spaces,

8. 16:14 – 17:57

   How to Determine Product Prioritization

   1. HSHarry Stebbings16:14

      there is also, you name your many different directions you can go in. How do you determine product prioritization and the decisions to make and focus on, versus those to put on the back burner for next quarter?

   2. KWKevin Weil16:26

      I think the number one thing is you've got to have a strategy. Um, and, and I haven't been at Twitter for years now, so I'll leave Twitter's particular, uh, strategy to it and the people that are there. But, uh, but I think you have to have a plan. That can come in any form, it doesn't, you know... I- I'm not a big subscriber to, "It has to be this way," or, "It has to be that way." It can be, you know, a six-page doc that just lays out, "Here's the direction we're going and here's why." And that gives the team a litmus test. Uh, it, it gives you a way to understand for any particular thing, "Is this part of our strategy or is it not?" And if it is, you know, maybe it's not worth debating exactly, "Should we do this now or should we do it later? This person wants to..." Like, just, just go. If it's aligned with the strategy, just go. Um, and, and if it's not in line with the strategy, then that closes off that discussion. Um, whereas if you don't have a strategy, or if you think you do but people don't really understand it, then there's no quick way to understand whether the something you want to build is in the right direction or not. And it leads to lots of one-off, "Should we do this or should we not?" kind of decisions. So, having a good strategy in place, it, it not only helps you make decisions, it empowers the people on the teams to make decisions on their own, which makes the whole organization run faster.

   3. HSHarry Stebbings17:41

      This, this is so on fact, 'cause we had this scheduled and I'm just enjoying it so much that I'm just freewheeling entirely.

   4. KWKevin Weil17:46

      (laughs)

   5. HSHarry Stebbings17:47

      Um, but the sun, the sun's out and so I'm gonna take liberty in doing so. You work with many startups today with Scribble. When we think about product strategy, are there consistencies in the mistakes that you see startups

9. 17:57 – 19:17

   Mistakes Early Startups Often Make

   1. HSHarry Stebbings17:57

      make, with regards to how they approach product strategy in the first one to two years?

   2. KWKevin Weil18:04

      Yeah. I mean, the first one to two years are totally different, right? Like, uh, you invest in the early stages in companies, and they're gonna pivot three times before they find anything. So, laying out a strategy and sticking to something is very... It assumes that you have some degree of product market fit. Um, I think when you're a small company, you have a belief, you have... There's some reason, there's some...... deep-seated problem that you're trying to solve. Otherwise, you wouldn't have gone through all the pain that's involved in, like, starting a company and going through the early stages. So I think it, you, you stay true to what that, that core belief is, but be flexible on how you get there. Um, and that, uh, in the early stages, that may mean to, making much bigger pivots than a later-stage company will make. And that's okay. Uh, but there's something, there's some driving reason why you started the company, and I think it's important to keep that.

   3. HSHarry Stebbings18:55

      I, I totally agree with keeping that. I, I do wanna ask, and kind of going back to kind of leadership lessons, sorry, 'cause I took us in very vehement directions.

   4. KWKevin Weil19:03

      (laughs)

   5. HSHarry Stebbings19:03

      I spoke to many of your teams before, and again, I spoke to James, and he told me that specifically you excel at comms across scaling teams. We spoke a little bit about your time at Instagram and Twitter, obviously both sizable teams by the time you were leading them.

10. 19:17 – 21:10

    What does it take for a product leader to be great at communication?

    1. HSHarry Stebbings19:17

       Uh, what does it take to be great at communications as a product leader, for you?

    2. KWKevin Weil19:24

       One thing that I've been slow to, to realize, but, you know, as, as, I think as I've come into it, it's helped me, is y- you actually, it's really important to be clear about a small number of things. Extremely clear about a small number of things that really matter. Um, it's, it's tempting every ti- like, if you're out speaking to your company a lot, it's tempting every week to get up there and say new things. You know, you feel like you said the previous thing before, and so it's time to say something new this time, or else, you know, keep them engaged, and show that you're having original thoughts and all of that.

    3. HSHarry Stebbings19:56

       (laughs)

    4. KWKevin Weil19:56

       And, and, and, and in actuality, especially as your organization grows, it's really important to just say the same things over and over again. And so, you gotta make sure that those are the right things, that you're sticking to the points that really, fundamentally matter, that you wanna drive into everyone's heads-

    5. HSHarry Stebbings20:13

       Sure.

    6. KWKevin Weil20:13

       ... and then you say them over and over. And the 12th time you've said something, when you're like, "These people can't possibly wanna hear me say this again. They must be so bored," that's when it's starting to finally kind of, like, get into their heads. And they're not just hearing it from you, they're actually thinking of it as, as their own set of ideas. They're starting to be able to develop litmus tests on their own to decide... Uh, they're starting to repeat your words back to you in other conversations. Like, that's when it starts to stick, and that's when you start to get alignment, and alignment creates confidence in the organization. It creates speed. But I really, I still have to check myself from like, "I wanna say new things. I have other ideas." But like, no. Say the, say the things that really matter and say them over and over again.

    7. HSHarry Stebbings20:54

       Can I ask, what forums do you find the best and what worked well for you, and what work didn't? If you think, we have, you know, posts. We have messaging. We have in-person meeting, virtual meeting. There's so many different ways that we can imbue that single core message that we wanna imbue.

11. 21:10 – 23:19

    Which forums work best for communication?

    1. HSHarry Stebbings21:10

       What d- worked for you and what didn't, in terms of the forums?

    2. KWKevin Weil21:14

       So, I like finding... Well, I guess, uh, uh, in general, I f- I, I, I write to think. And so for me, I try and, uh, having a written version of what I'm, uh, what I'm speaking through, what I'm thinking, is really important. I find slides can, you know, you can, you can get away with not completing your thoughts when you're speaking in bullets. Whereas if you're gonna try and write something down on paper, it's gonna force you to think all the way through it, and, and like have a narrative all the way through. Uh, so, I always start there. I think the other key thing, though, um, is y- having some sort of regular forum. Um, so that can be a weekly all-hands. It can be, um... I, with Planet, I write a note to the company every Monday, just sort of my top three things that I'm thinking about, and it's an opportunity, again, to like reinforce the things that are most important. Um, but you want some consistent forum, because otherwise, you're gonna get busy and not do it, and then you're only gonna do it when something's actually going wrong or when you need to, like... And then it's gonna feel sudden, and people are gonna be like, "Wait, why is he writing all, why, why is he talking to the whole company now?" You know? So, you want this consistent forum where you can, you can reiterate what matters, and you can turn on the blinker for people to things that are, you know, coming down the line that you want them to begin thinking about. So you can introduce change sort of gradually and in a steady way. Uh, so anyways, I, I find having a regular forum is really important.

    3. HSHarry Stebbings22:41

       I will say finally, a cadence that you know you'll be able to stick to. I find some people go, "I'm gonna do it weekly." And then very quickly, they can't do it weekly 'cause they don't have the time or whatever.

    4. KWKevin Weil22:50

       Right.

    5. HSHarry Stebbings22:50

       And then suddenly, they're like, "Well, it didn't work. I'm stopping." And it's like, if you just start monthly and always do it, you can move to fortnightly, and that's great. But set a cadence you know you'll stick to. So I, I totally agree there. In terms of comms and messaging internally, uh, in terms of scaling teams with that, where are the first places where comms messaging and this process breaks down with scale?

    6. KWKevin Weil23:15

       I think, uh, uh, scaling's interesting 'cause it's, it's, it's sort

12. 23:19 – 25:03

    Where is the first place comms break down when scaling?

    1. KWKevin Weil23:19

       of, um, it's almost, it's fractal in some way. Like, you can, you can talk about scaling a whole company, or you can talk about scaling, uh, a small part of the team. I think one of the challenges, the biggest challenges that, that come i- when you, you have one team. Again, whether it's a single team at your whole company 'cause you're like eight people and you have a five-person engineering team, and suddenly you, you have a 10-person engineering team, and you're doing two things at once. Or whether you're a big company, and this is one org splitting into two business units or something. But it's when you've had one team, and suddenly, you have two, and you're trying to do two things at once. You have to coordinate with people who aren't on your direct team. And if you're not careful, you can develop tribalism. People can start using words like us and them. And as you do this, it's, it's really important to keep communication open, to keep everyone focused on the mission, right? Not, not like your local team, but the mission. Why are you there? It's bigger than either of the two teams alone. And, uh, and, and to keep using the word we, right? It's all we. Nobody cares about the divisions between your teams. What matters is, are you achieving your mission? And so, like, but that split is really important, and it happens at every level of a company.

    2. HSHarry Stebbings24:28

       Man, I'm fascinated. Speaking of like us, we, kind of the tribalism that can ensue, with, with Twitter, you have, you know, the Twitter monetization engine with ads and the need to monetize and be a, a successful kind of profitable company, with also the product purity that the product and engineering teams have. How do you think about, as a product leader, balancing the mindset of revenue generation today with also the awareness of beautiful user experience, beautiful product, and having both those mindsets held at the same time?

13. 25:03 – 27:05

    How to balance revenue generation and beautiful UI

    1. HSHarry Stebbings25:03

    2. KWKevin Weil25:03

       (smacks lips) Well, I don't think that they're... That they're different or they have to be different. Um, you know, w- we, uh, uh, one of the things that, that I'm proud of from Twitter is we pioneered the idea of having ads inside a feed. Uh, you know, if you remember back to 2009, 2010, all your ads on a desktop were over on the right-hand side, and they were all horrible, right? Uh, they're... It's just a terrible experience. And i- interestingly, at Twitter, we kind of had no choice because Twitter was almost entirely mobile. There was a desktop experience, but it was, you know, some small fraction of our usage. Twitter was all mobile and there's no d- there's no side on a mobile device. And so the only place, if we were gonna try and make money, and you gotta make money in some way, otherwise, there's no Twitter in the future, um, i- is... Was to put the ads in the feed. And, and if you're gonna put them in the feed, they should feel like tweets, and wait, if they feel like tweets, what if they just were tweets? And what if the advertising medium felt like a part of the user experience? You know, the- these are all things that make sense today because a lot of products have adopted them, but at the time, they were kind of crazy and we had no idea if they were gonna work. But it was certainly an attempt to build an advertising product, a way for the company to make money that felt natural to the way people use the product, and we hoped one that would actually get ads, you know, people to, uh, businesses to engage with their customers in their advertising versus these, this very sort of separated thing that you get if you're watching like a TV ad. So, um, anyways, I, I, I don't think they have to be separate, obviously done poorly they are, but you can, you can try and integrate the two in a natural way.

    3. HSHarry Stebbings26:44

       I totally see that in terms of the integration. In terms of the seven years at Twitter, I'm, I kind of jumped over it, but I, I do wanna touch on it. What were some of the biggest takeaways for you from leading the product there in the final 18 months, but also the kind of five and a half years before scaling the org? What were some of the biggest takeaways for you and how did it shape the mindset?

    4. KWKevin Weil27:02

       (smacks lips) Well, so, I, I think one was really...

14. 27:05 – 31:14

    Biggest Takeaways from Leading Product at Twitter

    1. KWKevin Weil27:06

       When I look back at my time at Twitter, i- it's a lesson in humility, um, because... And, and, and this is true in a lot of dimensions, but I'll gi- I'll pick one. Um, in the early days, we thought of Twitter, a- and like, this is kind of true of social media in general, as this unalloyed good, right? And in the winter of 2010, 2011, for example, you had the Arab Spring happening. You had people in Tahrir Square speaking truth to power and using Twitter to give a voice to protests, to engage in democracy. I mean, actually, there was this crazy story where, um, we were... This is back in the day when you had to take downtime to upgrade, upgrade services, right? You remember sites would be like, "We're gonna be down for three hours 'cause we're upgrading our database or whatever." Um, and so we had to do that, and we had posted in advance, "We're gonna take the service down for a few hours." We were doing it in the middle of the night because that was as far off peak as we could go. Um, and someone from the State Department reached out, and this is a public story, so I'm not saying anything that, uh, can't be said. Someone from the State Department reached out and said, "Wait, wait, wait, you can't go down at, you know, 2:00 AM Pacific. That's the middle of the day in Egypt, and this is a really important... Twitter's a really important tool that protesters are using on a daily basis. You... They need Twitter, you can't go down at this time." And we were like, "Holy cow." Like (laughs) that's... You know, it just gives you this sense of the impact that a service like this is having on the world that the State Department reaches out and tells you when you're allowed to take downtime. So we actually did. We changed it. We went down in the middle of the day, Pacific Time, middle of the night, uh, in, in the Middle East, and, uh, anyway... So we had this sense of Twitter, we used to speak of it as the free speech wing of the Free Speech Party. A- a- and we, you know, we thought of this as this unalloyed good. Now, 10 years later, we've learned a lot, right? Like, you've seen also the ways that people weaponize free speech. They, they take free speech ab- absolutism and turn it into misinformation and bullying and many worse things. And I say that not to get into a free speech discussion here, uh, but only to say that I learned humility from watching this and watching it play out. Like, Twitter and social in general is as complex and subtle as human social interactions are. And the only thing I know for sure is that anyone who says that like, "Oh, the answers are easy," hasn't thought about it hard enough or hasn't been close to it. So I, I think that's true in a lot of different things, and that's why I say I learned a lot of humility from, uh, growing up at Twitter.

    2. HSHarry Stebbings29:45

       I, I maybe have a rather naive view of this, but I've got rather a strong view, which is like, the world is what you make of it, and Twitter is the same. And so if you go on my Twitter feed, it's very fitness oriented, it's very cooking recipe oriented, and that's pretty much it. There's no tr- reality TV series. There's no, like, models that inspire anorexia. There's no... There's d- it's actually a very fulfilling and wholesome feed because that's what I've crafted. You craft your own feed.

    3. KWKevin Weil30:14

       Yeah.

    4. HSHarry Stebbings30:14

       And actually, the ads are then tailored to it. Most of my ads are for cooking knives.

    5. KWKevin Weil30:19

       (laughs)

    6. HSHarry Stebbings30:19

       (laughs) Great, fine. That's okay. So I just get a great experience. So I, I, I think the demonization of social is actually really quite unfair 'cause it's what you make of it. Um, but I... Yeah, I have strong views in that one.

    7. KWKevin Weil30:32

       I- I- If the whole world were as wholesome as Harry Steving's, uh... (laughs)

    8. HSHarry Stebbings30:36

       (laughs)

    9. KWKevin Weil30:36

       ... it would be a different place.

    10. HSHarry Stebbings30:38

        ... it would be a very different place. Maybe not a great place. But, uh, I, I, I want to talk about a couple of other elements, like Catherine Porter. Wonderful discussion with Catherine Porter. And she asked, in terms of your leadership, she was like, "You need to go broad. He's such a fantastic talent. You need to go broad, Harry." I said, "Okay, let's do this." Um, she asked, "What are your single biggest leadership lessons?" She obviously worked with you at Meta. Uh, what, what would you say yours are in response?

    11. KWKevin Weil31:03

        Yeah. Catherine is such an incredible leader. Uh, uh, uh, I, the number one thing is it's all about the team. Hire people better than you, set directions, support them, have

15. 31:14 – 31:46

    Single Biggest Leadership Lessons

    1. KWKevin Weil31:14

       their backs, give them room to run, but that's basically the entire game. If you surround yourself by people that are better than you, you give them clear direction, you empower them, then almost, i- i- in all cases good things are gonna happen. Um-

    2. HSHarry Stebbings31:26

       What are the biggest hirin- what are the biggest hiring mistakes you've made?

    3. KWKevin Weil31:31

       Oh. I mean, I don't know. I try not to dwell too much on hiring mistakes. I mean, A, I'm certainly not gonna name anybody here. But like-

    4. HSHarry Stebbings31:41

       (laughs)

    5. KWKevin Weil31:41

       ... generally, uh, uh, hiring mistakes, you,

16. 31:46 – 32:58

    Kevin’s Biggest Hiring Mistakes

    1. KWKevin Weil31:46

       you make them because people are complex and you get a limited amount of time to interview. Uh, and so you don't always get to know the full person in your interview, so you're gonna make mistakes that way. And also, one thing I've learned is it's, it's really sort of situation dependent. You can have a person who's an amazing leader in one place and it just doesn't work out in w- for whatever reason in the, in this particular environment. And when it doesn't work out, that doesn't mean that, that they're not good, it just means it wasn't a match. And they can go off and do amazing things somewhere else. So it's also why I've learned not to take too much of a, um ... and that's a, that's a build too strong of an opinion when you see somebody was let go or somebody was fired from somewhere. You know, sometimes it means that they weren't in the right, uh, they don't have the right skills. But just as often it means that they weren't in the right environment for them, and they'll go thrive in another location.

    2. HSHarry Stebbings32:39

       Do you agree that certain people are meant for certain stages of a company development? Often people will say, "Ah, they're a great zero-to-one, but they're not, you know, hyper growth," or whatever it is, that very oper- operator led, but they're not craftspeople. Do you agree that people are destined for stages?

    3. KWKevin Weil32:56

       I don't know about destined. I

17. 32:58 – 34:08

    Are certain people good for certain stages of a company?

    1. KWKevin Weil32:58

       agree that people's, like, mindsets are definitely right for different things. Like, you, people, people, some people thrive on ambiguity. They want you to give them a blank space and say, "Go figure this thing out." And other people, other people would have no idea where to start if you did that to them. But if you give them something that's kind of working and you say, "Make this thing twice as efficient," uh, or, "Go perfect this thing, go find the edges, go find what's not right and make it better," then they're perfectly at home and are gonna do amazing work, work that would stupify the people that want a blank space. Right? People are, the people that want a blank space are like, "I don't wanna just, like, you know, mess around with the edges. Give me another blank space." So, I think you can learn those mindsets, and I think you, i- it's not destiny. But, I do think people, uh, people are best in different situations.

    2. HSHarry Stebbings33:49

       When doing references, do you have any favorite questions which help you unpack the weaknesses of someone? So like mine that actually Danny Herzberg at Sequoia taught me is, if you were to hire someone beneath Kevin, what would they be brilliant at? Because most often they will lead with, "Oh, they'd be really organized," because Kevin's

18. 34:08 – 36:02

    Questions to Ask When Doing References

    1. HSHarry Stebbings34:08

       not organized. Or what, what ... (laughs) I'm not saying that at all, but you know what I mean.

    2. KWKevin Weil34:12

       Yeah, yeah.

    3. HSHarry Stebbings34:12

       What, do you have any that help you really get to the crux of weaknesses?

    4. KWKevin Weil34:17

       So, yeah. I like to, um ... A, a, a friend of mine actually, a person I worked with at Instagram, um, this guy Mike DeVelin, who led analytics, had this, uh, this theory that's really resonated with me, that you want alternating skills, just like you were saying. You want alternating skills. And he kind of classified people into like, you know, are they, are they kind of, um ... I'm trying to remember the word he used. Um, uh, I don't remember. He had a provocative word for it. But basically, are they, are they the kind of person that like, they're, they're gonna, they're gonna instigate things and they're gonna break some eggs and cause some trouble? Or are they like a politician, uh, and not in the bad sense of the word, but a politician who's, who's gonna kind of smooth things over and make everyone work together well? And his theory was you want these sort of alternating rows of, of politicians and like instigators, um, and if you have that, you can actually be incredibly effective. And so I try and sometimes set that up and then ask people, uh, ask, which, which is this person and why, and what would their colleagues say about them? I think that's kind of the other trick is people are hesitant to say, uh, themselves me- necessarily to say something, you know, uh, constructive or negative about a person. But if you say like, "You know, what do their peers say about them?" Everyone can say, "Oh, their peers say." Um, so, uh, try and poke around that way and, and, and get insight.

    5. HSHarry Stebbings35:42

       Can I ask you a bit of a weird one? But I've interviewed now some of the best product leaders in the world, and, uh, a concerning trait that I've seen is there's more and more process-driven, uh, kind of bureaucratic product leaders that are operators and like to instill processes and more processes and more legislation and more, like, red tape.

19. 36:02 – 38:10

    Process-driven Product Leaders

    1. HSHarry Stebbings36:02

       And there's very little product innovation. There's very little craftsmanship. There's very little true leadership. It's much more, "I'm a pre-IPO or post-IPO company, and I am the grownup product operator." And then I compare it to the best that I'm friends with, like Belskey or like Tony Fadel, and they're still like the kids in the playground with product.

    2. KWKevin Weil36:22

       (laughs)

    3. HSHarry Stebbings36:22

       Like, brilliant minds, free, creative, visionary, but also hand on the tiller still. I'm not saying not. But like, do you share my concern around this rise of the kind of product operator leader and their actually ever-increasing dominance in orgs?

    4. KWKevin Weil36:40

       I do. I think you can, uh, uh, I, I think it's tempting to over-process something and also just kind of over-control things.

    5. HSHarry Stebbings36:47

       Oh.

    6. KWKevin Weil36:47

       Um, and I say this knowing that one of my weaknesses is I probably bring process in a little bit too late. I appreciate it. But it's, it's, I would rather make the error of having a little bit less process than having a little bit too much. Um, so I think it starts with, again, it starts with your strategy. If you have a bold strategy, if you have su- if you, if you can lay out an ambitious direction for the company, and then you have great people around you who can, uh, who can take that and, and sort of make it their own, and you leave them the room to go and do that, then I think you're going to get ambitious, bold work happening from your teams. Whereas if you feel a need to control it and kinda lock things down and op- have people operate within, you know, their particular silos, then, you know, you're gonna... If that's what you reward, then that's the kind of work you're gonna get. So, I think there's a huge amount of benefit in, like, laying out a bold direction, hiring great people, and letting them go at it.

    7. HSHarry Stebbings37:44

       I totally get you. I think that's right. Um, I do wanna move into a very important chapter, though, of your life, which is obviously Scribble. Um, if we start on Scribble, I'm really fascinated in you. You are a product OG, Kevin. Um, you're too humble to admit it, but you're a product OG. And when you think about investing today with Elizabeth and with Scribble, you have founder, you have market, and you have product. Or any of the three things, if it's post-product. As a product

20. 38:10 – 40:59

    Founder vs. Market vs. Product

    1. HSHarry Stebbings38:10

       person, how do you prioritize the three? And what takes centrality to you?

    2. KWKevin Weil38:17

       Uh, founder, for sure. No question. And this is early stage investing, right? Scribble is a, is a pre-seed/seed, uh, fund. So, at the early stages, to me, it's almost all founder. Because market will change, the product will definitely change. And, to me it's more, are they ambitious? Are they clear-eyed? Do they believe in themselves and what they're doing? And, you know, sure, if they're going after a tiny market somewhere that doesn't make sense and they're, they're totally, that's all they wanna do, then maybe it's not the right investment. But in most cases it's all about the founder.

    3. HSHarry Stebbings38:51

       I get you. I, I, I have one learning recently, which is I lost money, um, on a deal, and it's because there were negative externalities associated with a market that could render the company bust, essentially.

    4. KWKevin Weil39:04

       Mm-hmm.

    5. HSHarry Stebbings39:04

       And now I take market first. Market is the single most important thing. If there are externalities that can kill a company that you can't control, uh, no matter how good the founder is, it's not gonna work. And actually, when you think about, like, pivots, I know Twitter was a pivot from podcasting, obviously, to a social network, but they're all in the realm of the same sector. They're all in the realm of a recruitment marketplace, a customer success solution. And so I'm like, "Actually, I've got to like the narrative direction of where this is going." You know, it's like, the wave will change, but the tide is still the same. Do you know what I mean?

    6. KWKevin Weil39:41

       Mm-hmm.

    7. HSHarry Stebbings39:41

       Do you agree with that?

    8. KWKevin Weil39:42

       Yeah. I think-

    9. HSHarry Stebbings39:42

       Or are you still like, "Nah, don't buy it." (laughs)

    10. KWKevin Weil39:44

        Well, uh, like I said, I think that, I think you have to have a market that makes sense. But it's less the... I, I focus less on... I- if the market is big, if the opportunity is there, if they're not going after, like, a sub-segment of a sub-segment, then I think great founders are gonna figure it out. And it's also the case, uh, I always remind people of this 'cause at, at Planet, in my day job, we're kind of building a new market. And if you look at the size of that market today, it's big, but, uh, I think it's gonna be 10X as big in the future. And, uh, when people, when, like, Salesforce went public, you know, let alone when Salesforce started, but when Salesforce went public, you can go look at analysts saying, "Yeah, you know, the SaaS market, it's at least a $10 billion market." And I mean, now think of the SaaS market. I don't know how many trillions it is, right?

    11. HSHarry Stebbings40:32

        Mm-hmm.

    12. KWKevin Weil40:32

        So, these things also grow when you find the right product.

    13. HSHarry Stebbings40:35

        I totally get you, and I, I agree with that. Do you guys do market sizing analysis? Do you do outcome scenario plans? I find them useless because, like you said, you have Gartner giving you numbers, and it's just bullshit to me. Do you do them?

    14. KWKevin Weil40:50

        So, our, our litmus test is, what do you have to believe for this company to be 100X their current size or current valuation? And if

21. 40:59 – 41:59

    Outcome Scenario Planning

    1. KWKevin Weil40:59

       in the pro- if, if it's sort of like, "Well, you have to believe that this thing, this one thing goes really well," then you can build a good story around it. If instead, you're like, "Well, this has to work, and then at the same time, this market has to open up over here, and then if this competitor doesn't do..." Like, when you start staking beliefs, that's when we start getting a little nervous, when five things have to all work. Um, but if it's really like there's this one core thing and then you can see a real path to being 100X, that's kind of what we, what we look at.

    2. HSHarry Stebbings41:27

       No, I, I totally get you. I h- I, I call it multi-dependency risk, which is like where you need those multiple different things to all come together. It's interesting, we spoke before and you said that actually, because you mentioned, obviously, your day job with Planet there, you said that being an investor made you a better operator. I, I was intrigued. In what ways did it improve your operating mindset specifically?

    3. KWKevin Weil41:47

       A few ways. So, I mean, one is, one is just realizing that there, there is no one single way to succeed. Right? When you, when you read the biographies of successful

22. 41:59 – 46:38

    How did being an investor improve your operating ability?

    1. KWKevin Weil41:59

       companies or founders or whatever, it's always like you get the story that, "Well, they did this, and then, uh, obviously the step was this, and then obviously it was this, and it was just this single path that was, like, clear from the beginning." And it's never like that. It's full of twists and turns, unexpected changes and pivots and everything. And so much of it is, is remaining sort of open to listening to those, to those things, and then having just the raw determination to drive through when things are hard. Uh, and y- you work with a lot of different companies, and you see that play out in so many different ways. And it's just, you know, when you work at a company... I've worked at, I don't know, five companies, maybe, my whole life. So, I've seen five different things, and only three that really had any scale.... and getting to work with founders, we've invested in, you know, I think over a hundred companies, Elizabeth and I, over the course of the years. And, uh, and, uh, you just, you see, so now I've seen a hundred other stories, and it's so helpful.

    2. HSHarry Stebbings42:58

       Do you know what's interesting? It's the same with investing that I find. If you listen, and one thing I've learned from doing this show, there's no right way to invest.

    3. KWKevin Weil43:06

       Right.

    4. HSHarry Stebbings43:06

       And that's what I always say to people starting. It's like, just find the thing that you are singly best at in the world, or best at for you, and just do that as the investor. But don't try and be the analytical investor, the thesis-driven investor. Be you. Do you know what I mean?

    5. KWKevin Weil43:21

       Totally. Leadership's the same way, right? If you look at somebody who you think is a great leader, but who's sort of a different person to you... I mean, I couldn't lead the way Steve Jobs leads. It would kill me...

    6. HSHarry Stebbings43:31

       (laughs)

    7. KWKevin Weil43:31

       ... to, to act like that to people. And Steve Jobs has done amazing things, and you can't... You know? And, um, in the same way, you can look at, like, what Ron Conway's done and what Benchmark has done. They've both been massively successful and their investing philosophies could not be more different. So, there's no one way to do things. You find your own way.

    8. HSHarry Stebbings43:50

       What did you believe about company building that you now no longer believe, due to your experience investing? Obviously when you are operating, you learn things that you no longer believe, but like specifically that you've seen investing that you're like, renders previous beliefs false or wrong or different, compared to operational times?

    9. KWKevin Weil44:09

       I, I think it, it really is that there's no one way to do it, and it just repeats every time you see a company and a founder doing something a, a massively different way. And it's, it's also it- it's the mission. The mission matters so much to people. This is something that, you know, maybe I'm biased because this is a lot of how I choose where I spend my time. I want to work on a mission that, that matters in the world, and something that when I'm 80 years old and I've got, you know, grandkids on my knee, that I'm gonna be proud to say that I played a role in. But startups are really hard. It takes a ton of determination. You have to believe when there's no real logic to believing sometimes. And a lot of that, to me, is the mission. If you, if you're there because of the mission, and you're going through hard times, and in the middle of the darkest hour you can kind of look up and go, "Okay, can we still achieve that mission? The reason that I came, can we still achieve that? All right, we can." Then that's, it's, it, it gives you strength to sort of buckle down and fight through the bad times and come out the other end. Whereas if you're there for other reasons, you know, m- m- maybe you don't do that. So mission, to me, matters so much, and we see that play out in our best companies as well.

    10. HSHarry Stebbings45:19

        You know what it is also for me, is like, just through seeing so many companies, it's clarity of communication. I don't know if you find this, but, like, how many companies can succinctly put on a billboard, in less than 10 words, exactly what they do? Very, very few. And when you say to a founder, "If you had a billboard in Times Square, what would you put on it, less than 10 words?" Very few go, (snaps fingers) "This."

    11. KWKevin Weil45:40

        Yeah.

    12. HSHarry Stebbings45:40

        Uh, it astounds me.

    13. KWKevin Weil45:42

        And, and I think that it, it goes back to some of what we were talking about before. Because if you can't do that, then you probably can't impart it to your employees either.

    14. HSHarry Stebbings45:51

        Yeah.

    15. KWKevin Weil45:52

        And if you can't impart it to your employees, then they don't have the sense of who you are and what you're doing that motivates you. And if they don't have it, then in hard times, they're not gonna be able to fall back on, on the mission in the same way. And so I, I really think that there's a way that that cascades through the organization if you do it well. It's not just about putting it on a billboard. It means you can also put it in everyone's heads in a way that's really powerful.

    16. HSHarry Stebbings46:16

        You mentioned a hundred investments there. When you think back through the hundred investments, what was the biggest hit for you so far? And how did that change your mindset?

    17. KWKevin Weil46:25

        Hmm. Uh, I mean, we've been lucky. We've had, uh, we've, we've got a number of companies that are doing really well, like Whatnot, for example, is doing fantastically well, re-imagining live commerce. Um,

23. 46:38 – 47:48

    Kevin’s Biggest Hits

    1. KWKevin Weil46:40

       uh, i- i- it- it, I think a lot of it is... So you, you have to get kind of lucky to make a good investment, let's be honest. Um, uh, at least I think you have to get lucky. Maybe people are just way better at it than I am. Um, but i- it's, i- then you see, it's, it's those si- those same kinds of properties come through. So it's not just that you have a great idea, but then it's can you build a great team around you and, and, and begin to scale it? Can you, can you help the entire team understand the mission? Can you lay out a good strategy and then delegate responsibility so that you're getting great ideas from all hundred people on your team and not just relying on the founder after some point in scaling? So it's both. You get, like, the lightning in the bottle of having this initial thing that finds product-market fit, but then can you scale a company around yourself? And the ones that can do both are the ones that become really big companies.

    2. HSHarry Stebbings47:28

       Do you worry that you're too nice? What I mean by that is, as an operator, you naturally are like the founder's best friend all the way, all the way, all the way. And this idea that VCs and founders are always like, always aligned is complete crap. You are an amazing founder. You're like, "I want to bring in these amazing angels. Kevin, I want a bigger

24. 47:48 – 49:40

    Do you worry that you’re too nice?

    1. HSHarry Stebbings47:48

       check in your round. I want a million, not the 250K that you've given me." Do you find it hard having to be the VC where you're like, "You saved 200K for me, but I need a million now"? You have a fund, you have ownership goals, you have to hit them.

    2. KWKevin Weil48:04

       Yeah. Uh, to be honest, I do worry about that sometimes. But I think it comes back to you just can't be anyone other than who you are. You know, I, uh, I like to think I'm, I'm a, I'm a nice person, and I would have a really hard time being a different way. And, uh, rather than trying to be different, I think you have to win on, on who you are and how you can help. And so, you know, I like to think that, uh, I, I pride myself in working really hard for the companies that we invest in. And if, if I can bring the value that I can bring, and I'll work really hard for you, then like, you're gonna wanna do the right thing, and you're also gonna want us in future rounds. Like that's gonna, that's gonna compound over time. And in future rounds, we're gonna be able to put even more in because we've been helpful and because we're a group that you love to work with.... you know, which may be different than getting more in in, in the first round and then, uh, you know, poisoning a relationship, which hurts you both with that company and with every company that that person would then refer, potentially. So I think the right things happen over the long run, uh, and I try and, you know, fight in the way that makes sense for me to fight, and, and then just do my best and work hard for people.

    3. HSHarry Stebbings49:14

       You mentioned WotNot as a massive hit. I actually had Grant on the show. Fantastic, fantastic guy. Um, misses? We always learn from our misses too. What's been the biggest miss, and what did you learn from that?

    4. KWKevin Weil49:25

       So, I mean, I won't name names, but there are a couple companies that I chose not to invest in because they were founded by people whose work that, um, I just, uh, that, that I worked with and, and for whatever

25. 49:40 – 51:10

    Kevin’s Biggest Misses

    1. KWKevin Weil49:40

       reason in that environment, weren't amazing. And so I made the assumption that that was them, not some combination or interplay between them and the environment that they were in, and I didn't invest, and they went on to do amazing things. And it's just been a reminder to me that it isn't just the people. It's also the setting matters. And, uh, some people, I, like as you said, about, uh, zero to one people or, or, uh, whatever sort of perfecting something that exists kind of people, you can be not great in one environment and then go shine in another environment. And so I always try and sort of reset my slate when I talk to people.

    2. HSHarry Stebbings50:17

       I, my, my biggest miss is, I, I did a reference and they said they were terrible at the company and useless-

    3. KWKevin Weil50:23

       Right.

    4. HSHarry Stebbings50:23

       ... and disruptive. And yeah, they were useless and disruptive, but they hated working in a team with an asshole leader. (laughs)

    5. KWKevin Weil50:30

       Right.

    6. HSHarry Stebbings50:31

       And so, that was my big miss.

    7. KWKevin Weil50:32

       And it turns out they're a great founder, yeah.

    8. HSHarry Stebbings50:34

       Amazing founder. Um, yeah, missed that one. Fuck. Um, anyway-

    9. KWKevin Weil50:38

       (laughs)

    10. HSHarry Stebbings50:38

        ... uh, (laughs) I want to move into a quick fire round, Kevin. So I say a short statement and you give me your immediate thoughts. Does that sound okay?

    11. KWKevin Weil50:44

        Yeah, let's do it.

    12. HSHarry Stebbings50:46

        So you run like insane amounts. You know, sometimes 100 mile races. When the running kind of wall hits and you just feel you can't do any more, what do you say to yourself? What is that mind talk?

    13. KWKevin Weil51:01

        I try and always remind myself that it's y- how you feel in a race, especially a long one, is kind of a sinusoid. Like, you're gonna have moments that are good and moments that are bad.

26. 51:10 – 52:08

    What do you say to yourself when you’re running and you want to give up?

    1. KWKevin Weil51:10

       But because you felt good an hour ago and you feel bad now doesn't mean you're gonna feel worse in two hours. What you actually need to do, you're probably dehydrated a little bit or you need food, and if you take care of what's, uh, what you need to right now, you grind through it, and 20 minutes from now, you're gonna feel better. And you have to tell yourself that because you're naturally gonna be like, "Oh, I'm gonna feel worse in an hour. This is terrible." You don't let yourself get into that mindset. You actually can do some things, you make it better, and then you grind through it, and I think that has applications in running and, uh, probably also in life and in work.

    2. HSHarry Stebbings51:44

       What changes have you made in your athletics, running, cycling, that have made the biggest differences, be it diet, be it training, be it equipment?

    3. KWKevin Weil51:56

       Probably just consistency, to be honest. Um, I think people, people move from fad to fad, and, you know, whether it's diet or training or whatever, and it's actually

27. 52:08 – 52:50

    Biggest difference-makers in improving your athleticism?

    1. KWKevin Weil52:08

       just, just getting up and doing it every day actually matters a ton. I, I try and kind of always keep myself in a place where if a friend has like a stupid idea for a crazy race that we should go run, that I can kind of drop everything and go do it, and not be like, "Oh, well, I haven't been training as much, so give me two months."

    2. HSHarry Stebbings52:27

       What's your training routine?

    3. KWKevin Weil52:29

       I will go, let's see, I- I don't miss a day. Um, uh, so I probably haven't missed a day in years. I tend to work out for an hour or two a day, you know, either I'll go run, um, 10 or 12 miles or I'll, uh, be on my bike and trainer, try and do some weights. But like whatever it is, I'm, I'm anal about

28. 52:50 – 53:48

    Kevin’s Training Routine

    1. KWKevin Weil52:50

       this. I like, will do it every day, for better or worse. (laughs)

    2. HSHarry Stebbings52:55

       I love that. That's hilarious. Um, I, I think you missed the, the school of thought that said rest days was an important part of it. (laughs)

    3. KWKevin Weil53:02

       Yeah. Well, you know, it's-

    4. HSHarry Stebbings53:03

       Uh-

    5. KWKevin Weil53:04

       ... y- y- you have, you modulate, right? I don't go hard every day. I'll have days where I feel easy. I kind of listen to my body more than I, more than I follow any particular training plan. So if I'm not feeling great, I'll, I'll, you know, ride my bike instead of run, and that gives my knees a break. Yeah, and so I try and listen to my body, but I'm always doing something.

    6. HSHarry Stebbings53:21

       How many calories do you eat a day, Kevin?

    7. KWKevin Weil53:24

       I don't know, a lot. (laughs)

    8. HSHarry Stebbings53:26

       A lot?

    9. KWKevin Weil53:27

       A lot. I try and eat healthy, but I eat a lot of volume.

    10. HSHarry Stebbings53:30

        (laughs) I can't remember who it was who told me, they were like, "Don't see a hangry Kevin." That was one last thing.

    11. KWKevin Weil53:37

        (laughs) Maybe my wife. (laughs)

    12. HSHarry Stebbings53:39

        Um, do you know who it wasn't? It was someone who worked with you. (laughs)

    13. KWKevin Weil53:43

        (laughs)

    14. HSHarry Stebbings53:43

        Um, okay. Who's the best board member that you've worked with and why?

    15. KWKevin Weil53:47

        Uh, I'll

29. 53:48 – 54:10

    How many calories do you eat per day?

    1. KWKevin Weil53:48

       give you three, actually. Uh, Peter Fenton, David Rosenblatt, and Carl Bass. Peter and David-

    2. HSHarry Stebbings53:54

       Why?

    3. KWKevin Weil53:54

       ... were on our board at, board at Twitter. Carl's on the board at Planet. Because every single one of them, they are available whenever you need them, they're dedicated, they're just like, "Tell me how I can help." Um, all three of them are people that I would call when I had a problem and I felt like I could call them, and when I called them,

30. 54:10 – 54:45

    Best Board Members

    1. KWKevin Weil54:10

       it wasn't an inconvenience. They were just like, "All right, let me de- let me know what I can do to help." And they were all like uniformly valuable whenever you need them.

    2. HSHarry Stebbings54:19

       What would you most like to change about the world of venture?

    3. KWKevin Weil54:24

       Uh, less hype, more hard work for founders. I think the industry's kind of 50/50 there. You know, some people are, some people are in like hustling every single day for the right things and helping their portfolio companies and others are not.

    4. HSHarry Stebbings54:38

       Which product leader do you most re- admire and respect?

    5. KWKevin Weil54:44

       I have been

31. 54:45 – 55:05

    What would you most like to change about Venture?

    1. KWKevin Weil54:45

       so lucky in my career, um, you know, across folks like Kevin Systrom, Jack Dorsey, et cetera. Um, uh, uh, David Marcus, who was my boss in my previous role, was incredibly well-rounded, like...He was-- the, the thing I really learned from him, he was a great product leader. His instincts were really good. But he also really trusted his team.

32. 55:05 – 55:53

    Which product leader do you admire most?

    1. KWKevin Weil55:05

       And so, he would step back and he would give us a lot of room to execute, and he built a great team around himself. Uh, and then when something wasn't going right, he wasn't afraid to dive in. And when he-- and when he dove in, his instincts were really good. But in most cases, he would just sort of set a direction and, and, and let us operate, and that's been something I've really tried to, to take forward myself.

    2. HSHarry Stebbings55:26

       Kevin, you run 100-mile races. You have three wonderful kids. You're on-- work at Planet. You work with Scribble. L- literally, how do you actually do it?

    3. KWKevin Weil55:38

       (laughs) Uh, my wife would be the first person to tell you, I do not have it figured out. Um, I mean-

    4. HSHarry Stebbings55:44

       (laughs)

    5. KWKevin Weil55:44

       ... I'm usually up at 5:00 to get a workout in, you know, take the kids to school, play with them in the mornings, work, come back home, uh,

33. 55:53 – 57:18

    How do you manage to accomplish so much?

    1. KWKevin Weil55:53

       see Elizabeth, see the kids, and then usually get back on and do some more work. So, I guess I sacrifice sleep, which is getting harder and harder as I get older. Um-

    2. HSHarry Stebbings56:02

       What time do you go to bed?

    3. KWKevin Weil56:05

       ... midnight, 1:00 AM, um, except for-

    4. HSHarry Stebbings56:09

       Can you get up at-

    5. KWKevin Weil56:09

       ... Tuesdays. We try and, we try and have date night on Tuesdays, and Elizabeth and I try to be religious about it. We're not perfect, but we try to be religious about it, and it's like the one night where we, you know, go to a movie, go to dinner, go on a bike ride, kind of whatever. Um, and I really try hard not to work in- that evening, uh, and that's a really nice thing. So, that's been like one of the-- one of the things we've tried that's really worked. But-

    6. HSHarry Stebbings56:32

       Do you worry-

    7. KWKevin Weil56:32

       ... I do not have it figured out.

    8. HSHarry Stebbings56:34

       Do you worry about the four hours sleep?

    9. KWKevin Weil56:36

       Yeah, totally. I think it's-

    10. HSHarry Stebbings56:38

        Sure.

    11. KWKevin Weil56:38

        ... probably not good for me and I am trying to get better, trying to like get more efficient faster than, um, than I take on new things. And that means also-

    12. HSHarry Stebbings56:48

        But-

    13. KWKevin Weil56:48

        ... for me learning to say no, which I'm not good at.

    14. HSHarry Stebbings56:51

        Penultimate one, if I could remove one recurring thing from your calendar, what would I remove?

    15. KWKevin Weil56:57

        Oh, that's a great question. That is a great question. Uh, gosh, I don't know. I mean, I like to think... I, I, I really with, with kids and work and all this other stuff, like I really actually try hard to not have recurring things on the calendar that aren't useful. Um, I work with my assistant

34. 57:18 – 58:08

    If you could remove one thing from your calendar, what would it be?

    1. KWKevin Weil57:18

       who's unbelievable and, uh, and we do a calendar audit pretty regularly to say like, "Is all this stuff really valuable? Do we really need it?" Um, I'll have to give that one more thought because I'm sure there's stuff on there, but I really try hard not to do it because I just-

    2. HSHarry Stebbings57:33

       I-

    3. KWKevin Weil57:33

       ... I have no, I have no free time, you know?

    4. HSHarry Stebbings57:36

       I love that question. You should be on more boards. Trust me-

    5. KWKevin Weil57:39

       (laughs)

    6. HSHarry Stebbings57:39

       ... that's something you want to get off. Um, final one, what's the most recent publicly announced investment and why did you say yes and get so excited with Scribble?

    7. KWKevin Weil57:47

       Yeah, it's a company called Fig, uh, and what they're doing is reimagining the terminal experience. So, if you're a developer you spend a lot of your time in the terminal, um, like in the shell, and they're basically building all kinds of, uh, of, of new features into the shell. The shell hasn't changed since like 1969 with the original

35. 58:08 – 58:56

    Kevin’s Most Recent Publicly Announced Investment

    1. KWKevin Weil58:08

       Unix shell, and they're building auto-complete and they're making it a platform and doing all this cool stuff. They're doing it in an open source way. Um, I really have enjoyed working with the founders and getting to know them. Uh, we actually originally made an angel investment in Fig pre-Scribble and then followed up with a bigger investment from Scribble, uh, and they're just... they're, they're super customer focused, uh, they're innovative, they're not afraid to try new things, but like every bit that they do, they're, they're engaging with their community and building what their community wants. I've just... I've loved watching that feedback over time. So, I'm excited about where they go.

    2. HSHarry Stebbings58:44

       Kevin, I've, I've loved this. We've taken it in many different directions from calories and sleep, to, you know, lessons from Instagram and Twitter and investing. So, thank you so much for the broad conversation, and I absolutely loved it.

    3. KWKevin Weil58:55

       Thank you so much for ha-

Episode duration: 58:56