The Exchanges

Q Do you have any help you really get to the crux of weaknesses?

A So, yeah, I like to, um, 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, 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, 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, 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 themselves necessarily to say something, you know, uh, constructive or negative about a person. But if you say like, you know, what are their peers say about them? Everyone can say, …

AI assessment note: “what would their colleagues say about them? I think that's kind of the other trick”

Q Do you have any help you really get to the crux of weaknesses?

A So, yeah, I like to, um, 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, 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, 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, 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 themselves necessarily to say something, you know, uh, constructive or negative about a person. But if you say like, you know, what are their peers say about them? Everyone can say, …

AI assessment note: “if you say like, you know, what are their peers say about them?”

Q 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?

A Hmm. Uh, I mean, we've been lucky. We've had, uh, we've got a number of companies that are doing really well, like, Whatnot, for example, is doing fantastically well, reimagining live commerce. Um, 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, at least I think you have to get lucky. Maybe people are just way better at it than I am. Um, but it's, then you see it's, it's those, the same kinds of properties come through. So it's not just, did 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 at scaling? So it's both, do 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.

AI assessment note: “Whatnot, for example, is doing fantastically well, reimagining live commerce.”

Q 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 and what were your lessons and learnings from that experience?

A So, Let me, 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. Uh, 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 IC PM, 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, a 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 t…

AI assessment note: “maybe more of a leadership mistake. I mean, there have been a number of failed product”

Q 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 and what were your lessons and learnings from that experience?

A So, Let me, 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. Uh, 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 IC PM, 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, a 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 t…

AI assessment note: “maybe more of a leadership mistake... when I stepped into the, the leadership role at Twitter”

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: “you really focus on what's underneath what they're saying.”

Q 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?

A Hmm. Uh, I mean, we've been lucky. We've had, uh, we've got a number of companies that are doing really well, like, Whatnot, for example, is doing fantastically well, reimagining live commerce. Um, 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, at least I think you have to get lucky. Maybe people are just way better at it than I am. Um, but it's, then you see it's, it's those, the same kinds of properties come through. So it's not just, did 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 at scaling? So it's both, do 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.

AI assessment note: “Whatnot, for example, is doing fantastically well, reimagining live commerce.”

Q 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. When you make any changes, 99% of people say, I hate it, I hate it, because they like 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?

A 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 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 actually, I think I always, despite having, it's really important to have lots of data because 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.

AI assessment note: “I don't think there's a science to it, to be honest.”

Q 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, like, renders previous beliefs false or wrong or different compared to operational times.

A I think 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 do something 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 going to 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 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, 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.

AI assessment note: “I think it really is that there's no one way to do it.”

Q What are the biggest hiring? What are the biggest hiring mistakes you've made?

A Oh, I mean, I don't know. I try not to dwell too much on hiring mistakes. I mean, Hey, I'm certainly not going to name anybody here, but like generally hiring mistakes. You, 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 going to 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. And for whatever reason in the, in this particular environment, and when it doesn't work out, it 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, not to 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, 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.

AI assessment note: “I try not to dwell too much on hiring mistakes. I mean, Hey, I'm certainly not going to name anybody”

Q 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, like, renders previous beliefs false or wrong or different compared to operational times.

A I think 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 do something 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 going to 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 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, 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.

AI assessment note: “I think it really is that there's no one way to do it.”