The Exchanges

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

A So there were three things, and let me see if I can remember them all because 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 the permanent, right? You, when you post it 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 You got a hundred likes on your last post. Are you going to get a hundred likes on this post? Like if you don't, all of your friends are going to see that it wasn't as popular. 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 kind of, 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.

AI assessment note: “there were three things that were sort of key to Instagram that we just needed to flip”

Q Not at all. I'm excited for this, but I want to start, and 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 orgs as you have done?

A So completely unintentionally is the answer. Um, 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. 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, 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 We were just surrounded by all of 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 want to go do that. And so, uh, really thanks to her. And, you know…

AI assessment note: “So completely unintentionally is the answer.”

Q I love that question. You should be on more boards. Trust me. Um, final one. What's the most recent publicly announced investment and why did you say yes and get so excited with Scribble?

A 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, uh, 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 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. Um, 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.

AI assessment note: “Yeah, it's a company called Fig, uh, and what they're doing is reimagining”

Q you mentioned conviction, decision making, and then stories, and the backdrop of stories. From the outside, and maybe this is naive, it looked like a reactive move from, like, towards Snapchat's, obviously, stories which were phenomenally successful. Is that true? If so, is that kind of conviction and decision making, because it's a reactive move based on a competitor, like, and what's the backstory there? I'm intrigued you mentioned it.

A 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 want to share this way. And it just showed that Instagram didn't have that way of sharing. 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 want to represent myself forever? 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 going to get a hundred likes? Ah, maybe it's not, maybe, maybe this isn't good enough to post on Instagram. You know, 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 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, and, and then how exactly they…

AI assessment note: “for sure, in that sense, it was, it was a reaction”

Q the seven years at Twitter, I'm, I kind of jumped over it, but I, I do want to 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?

A Well, so I think one was really, when I look back at my time at Twitter, it's a lesson in humility, um, because, and this is true in a lot of dimensions, but I'll give, I'll pick one. Um, in the early days, we thought of Twitter, and like, this is kind of true of social media in general, as this unalloyed good. Right. And in the winter of 2010, 20 11, 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 down time to upgrade, upgrade services, right? You remember sites would be like, we're going to be down for three hours because 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 can't be said. Someone from the State Department reached out and said, wait, wait, you can't go down at, you know, two a.m. 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 dai…

AI assessment note: “when I look back at my time at Twitter, it's a lesson in humility”

Q and then I compare it to the best that I'm friends with, like, Belsky or, like, Tony Fidel, and they're still, like, the kids in the playground with product, 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?

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

AI assessment note: “I do. I think you can, uh, I think it's tempting to over process”

Q you mentioned conviction, decision making, and then stories, and the backdrop of stories. From the outside, and maybe this is naive, it looked like a reactive move from, like, towards Snapchat's, obviously, stories which were phenomenally successful. Is that true? If so, is that kind of conviction and decision making, because it's a reactive move based on a competitor, like, and what's the backstory there? I'm intrigued you mentioned it.

A 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 want to share this way. And it just showed that Instagram didn't have that way of sharing. 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 want to represent myself forever? 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 going to get a hundred likes? Ah, maybe it's not, maybe, maybe this isn't good enough to post on Instagram. You know, 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 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, and, and then how exactly they…

AI assessment note: “for sure, in that sense, it was, it was a reaction to seeing”

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

A So there were three things, and let me see if I can remember them all because 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 the permanent, right? You, when you post it 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 You got a hundred likes on your last post. Are you going to get a hundred likes on this post? Like if you don't, all of your friends are going to see that it wasn't as popular. 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 kind of, 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.

AI assessment note: “there were three things that we, um, that were sort of key to Instagram”

Q us in very vehement directions. 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. What does it take to be great at communications as a product leader for you?

A 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 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 time, 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, you know, keep them engaged and, Show that you're having original thoughts and all of that. 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 got to make sure that those are the right things that you're sticking to the points that really fundamentally matter that you want to drive into everyone's heads. 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 want to 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. They're starting to repeat your word…

AI assessment note: “it's really important to be clear about a small number of things”

Q 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. 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?

A I think the number one thing is you've got to have a strategy. Um, 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'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 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 there's 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 f…

AI assessment note: “gives the team a litmus test... Is this part of our strategy or is it not?”

Q 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, hypergrowth, or whatever, they're very operator lab, but they're not crafts people. Do you agree that people are destined for stages?

A I don't know about destined. I agree that people's like mindsets are definitely right for different things. Like you, people, people, some people thrive in 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 going to do amazing work, work that would stupefy the people that want a blank space, right? People, the people that want a blank space are like, I don't want to 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, it's not destiny, but I do think people, uh, people are best in different situations.

AI assessment note: “I don't know about destined. I agree that people's like mindsets are definitely right”

Q Which product leader do you most admire and respect?

A I have been so lucky in my career, um, you know, across folks like Kevin Systrom, Jack Dorsey, et cetera. Um, David Marcus, who was my boss in my previous role was incredibly well-rounded. Like he was 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. 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 we, and when he dove in, his instincts are 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 take forward myself.

AI assessment note: “David Marcus, who was my boss in my previous role was incredibly well-rounded.”

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

A I try and always remind myself that it's how you feel in a race, especially a long one is kind of a sinusoid. Like you're going to have moments that are good and moments that are bad, but because you felt good an hour ago and you feel bad now doesn't mean you're going to 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 going to feel better. And you have to tell yourself that because you're naturally going to be like, oh, I'm going to 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. I think that has applications in running and, uh, probably also in life and in work.

AI assessment note: “I try and always remind myself that it's how you feel in a race”

Q You mentioned Whatnot 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?

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

AI assessment note: “there are a couple of companies that I chose not to invest in”

Q 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?

A So when I was leaving Twitter after about seven years there, it wasn't the first company I'd ever been at, but it was the first company I'd ever been at where It was all successful and I had any degree of responsibility. And, uh, somebody I 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 of that. And it was so right. So I give, I give Kevin Systrom 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 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, if you think back to…

AI assessment note: “I'd say a couple things stand out from working with Kevin. Um, number one”

Q us in very vehement directions. 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. What does it take to be great at communications as a product leader for you?

A 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 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 time, 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, you know, keep them engaged and, Show that you're having original thoughts and all of that. 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 got to make sure that those are the right things that you're sticking to the points that really fundamentally matter that you want to drive into everyone's heads. 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 want to 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. They're starting to repeat your word…

AI assessment note: “it's really important to be clear about a small number of things”

Q I totally get you. I, 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?

A 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 companies or founders or whatever, it's always like you get this story that, well, they did this and then, and obviously the step was this, and then obviously it was this, and it was just the 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. Um, and you, 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 you just, you see, so now I've seen a hundred other stories and it's so helpful.

AI assessment note: “one is just realizing that there, there is no one single way to succeed”

Q Which product leader do you most admire and respect?

A I have been so lucky in my career, um, you know, across folks like Kevin Systrom, Jack Dorsey, et cetera. Um, David Marcus, who was my boss in my previous role was incredibly well-rounded. Like he was 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. 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 we, and when he dove in, his instincts are 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 take forward myself.

AI assessment note: “David Marcus, who was my boss in my previous role was incredibly well-rounded.”

Q 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. 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?

A I think the number one thing is you've got to have a strategy. Um, 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'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 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 there's 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 f…

AI assessment note: “you've got to have a strategy... that gives the team a litmus test”

Q Can I ask, what forums do you find the best and worked well for you and what worked 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 want to imbue. What worked for you and what didn't in terms of the forms?

A So I like finding, well, I guess in general, I, I, I write to think. And so for me, I try and 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 going to try and write something down on paper, it's going to force you to think all the way through it and, and like have a narrative all the way through. Um, so I always start there. I think the other key thing though, um, is 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 going to get busy and not do it. And then you're only going to do it when something's actually going wrong or when you need to, and then it's going to feel sudden and people are going to be like, wait, why is he writing all right? 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 t…

AI assessment note: “with Planet, I write a note to the company every Monday”

Q 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, hypergrowth, or whatever, they're very operator lab, but they're not crafts people. Do you agree that people are destined for stages?

A I don't know about destined. I agree that people's like mindsets are definitely right for different things. Like you, people, people, some people thrive in 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 going to do amazing work, work that would stupefy the people that want a blank space, right? People, the people that want a blank space are like, I don't want to 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, it's not destiny, but I do think people, uh, people are best in different situations.

AI assessment note: “I agree that people's like mindsets are definitely right for different things.”

Q the seven years at Twitter, I'm, I kind of jumped over it, but I, I do want to 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?

A Well, so I think one was really, when I look back at my time at Twitter, it's a lesson in humility, um, because, and this is true in a lot of dimensions, but I'll give, I'll pick one. Um, in the early days, we thought of Twitter, and like, this is kind of true of social media in general, as this unalloyed good. Right. And in the winter of 2010, 20 11, 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 down time to upgrade, upgrade services, right? You remember sites would be like, we're going to be down for three hours because 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 can't be said. Someone from the State Department reached out and said, wait, wait, you can't go down at, you know, two a.m. 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 dai…

AI assessment note: “when I look back at my time at Twitter, it's a lesson in humility”

Q Can I ask, what forums do you find the best and worked well for you and what worked 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 want to imbue. What worked for you and what didn't in terms of the forms?

A So I like finding, well, I guess in general, I, I, I write to think. And so for me, I try and 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 going to try and write something down on paper, it's going to force you to think all the way through it and, and like have a narrative all the way through. Um, so I always start there. I think the other key thing though, um, is 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 going to get busy and not do it. And then you're only going to do it when something's actually going wrong or when you need to, and then it's going to feel sudden and people are going to be like, wait, why is he writing all right? 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 t…

AI assessment note: “with Planet, I write a note to the company every Monday”

Q 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?

A So when I was leaving Twitter after about seven years there, it wasn't the first company I'd ever been at, but it was the first company I'd ever been at where It was all successful and I had any degree of responsibility. And, uh, somebody I 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 of that. And it was so right. So I give, I give Kevin Systrom 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 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, if you think back to…

AI assessment note: “number one, he's the best editor I've ever seen. He spent a ton of time”

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

A 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, if you ask customers what you want, what they want, they'll tell you they want faster horses. 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.

AI assessment note: “What you need to do is get a good, is do a good job getting underneath”

Q 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? Do you agree with that or are you still like, nah?

A Well, like I said, I think that, I think you have to have a market that makes sense. But it's less that I focus less on 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 going to figure it out. And it's also the case. I always remind people of this because 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 I think it's going to be 10 X's big in the future. And 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 is at least a ten billion dollar market. And I mean, now think of the SaaS market. I don't know how many trillions it is, right? So these things also grow when you find the right product.

AI assessment note: “I think you have to have a market that makes sense. But it's less”

Q 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 gotten them giving you numbers, and it's just bullshit to me. Do you do them?

A So our, our litmus test is what do you have to believe for this company to be a hundred X their current size or current valuation? And if in the, 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 that, like, When you start stacking 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 a hundred X, that's kind of what we, what we look at.

AI assessment note: “our litmus test is what do you have to believe for this company to be”

Q You mentioned Whatnot 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?

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

AI assessment note: “it isn't just the people. It's also the setting matters.”

Q I totally get you. I, 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?

A 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 companies or founders or whatever, it's always like you get this story that, well, they did this and then, and obviously the step was this, and then obviously it was this, and it was just the 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. Um, and you, 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 you just, you see, so now I've seen a hundred other stories and it's so helpful.

AI assessment note: “realizing that there, there is no one single way to succeed”

Q 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 gotten them giving you numbers, and it's just bullshit to me. Do you do them?

A So our, our litmus test is what do you have to believe for this company to be a hundred X their current size or current valuation? And if in the, 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 that, like, When you start stacking 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 a hundred X, that's kind of what we, what we look at.

AI assessment note: “So our, our litmus test is what do you have to believe for this company”