The Exchanges

Q How do you think about market timing, then, as a VC? With that in mind, Because obviously timing is always crucial. What are your takes on the importance of market timing and, and especially that where I think Sonos is probably a rare example where it was maybe too early, but it kind of worked out incredibly well, no?

A Yeah, absolutely. I mean, I think timing is a tricky thing. It's a tricky needle to thread where you want to be ahead of the trend, but not too far ahead of the trend, right? So for example, you know, the company I worked at earlier in my career was OpenWave, and we created the first mobile browser, and really we're selling the promise of the mobile internet. Well, that was a company that got a lot of hype at the time, but the market for, you know, true mobile data and mobile internet didn't come till much, much later. It came like 10 years later, and OpenWave had already boomed and busted by the time the market was there. So the ability to sustain and ride with the wave of innovation is really critical. One thing I've noticed on that Front just real quick is I always think back like the companies that do a vertically integrated product when the market's early seem to have a better chance, in my opinion, than trying to be one piece of technology in the stack of a market before the market is there.

AI assessment note: “want to be ahead of the trend, but not too far ahead of the trend”

Q How do you think about market timing, then, as a VC? With that in mind, Because obviously timing is always crucial. What are your takes on the importance of market timing and, and especially that where I think Sonos is probably a rare example where it was maybe too early, but it kind of worked out incredibly well, no?

A Yeah, absolutely. I mean, I think timing is a tricky thing. It's a tricky needle to thread where you want to be ahead of the trend, but not too far ahead of the trend, right? So for example, you know, the company I worked at earlier in my career was OpenWave, and we created the first mobile browser, and really we're selling the promise of the mobile internet. Well, that was a company that got a lot of hype at the time, but the market for, you know, true mobile data and mobile internet didn't come till much, much later. It came like 10 years later, and OpenWave had already boomed and busted by the time the market was there. So the ability to sustain and ride with the wave of innovation is really critical. One thing I've noticed on that Front just real quick is I always think back like the companies that do a vertically integrated product when the market's early seem to have a better chance, in my opinion, than trying to be one piece of technology in the stack of a market before the market is there.

AI assessment note: “you want to be ahead of the trend, but not too far ahead”

Q Which contrarian thinker have you most enjoyed working with? So as one of the most enjoyable person to work with, it's like, whose completely radical ideas, maybe sometimes mildly insane, do you find incredibly refreshing and inspiring?

A Yeah, I think the biggest contrarian, I go back, I'm such a John McFarlane fanboy having, I worked for him for like eight years when I was in my early to mid twenties. I think if you put yourself back in his mindset in the early days of when the internet was being created, he was very, very much, you know, there were all these big, powerful companies trying to create these standards, you know, internet standards and make them as proprietary as possible. And he was Just a total contrarian at the time, the world kind of evolved this way, and being a huge proponent of open standards, and really believing that these interchange of technologies across services would, like, grow the whole market a lot faster than if they were to be siloed, and, you know, seeing the walls break down around SMS and stuff was a, that now it seems obvious, but at the time that wasn't obvious.

AI assessment note: “I'm such a John McFarlane fanboy having, I worked for him”

Q I do want to discuss the transition. From operator to VC, we spoke about some of the founders that you've worked with. One founder that you backed, Alexandra Lola, before the interview, asked a very poignant question being, as an operator turned VC, what do you think characterizes your approach to really working with portfolio companies today?

A Yeah, I mean, my approach is based on the fact that I think I'm pretty fortunate to be a well-rounded exec at the startups that I worked at. So I ran engineering teams, product design teams, and marketing partnership teams. So I've seen all the kind of the critical bits of inside the startups and had to make all those decisions around how we organize and how we hire and how we plan and prioritize. And so I think my approach usually, since what I have to go on is that experience, I try to think of myself as an extension of their team. Think of myself as an embedded resource that's helping them think through all these decisions and Just like I did when I was an operator.

AI assessment note: “I try to think of myself as an extension of their team.”

Q Which contrarian thinker have you most enjoyed working with? So as one of the most enjoyable person to work with, it's like, whose completely radical ideas, maybe sometimes mildly insane, do you find incredibly refreshing and inspiring?

A Yeah, I think the biggest contrarian, I go back, I'm such a John McFarlane fanboy having, I worked for him for like eight years when I was in my early to mid twenties. I think if you put yourself back in his mindset in the early days of when the internet was being created, he was very, very much, you know, there were all these big, powerful companies trying to create these standards, you know, internet standards and make them as proprietary as possible. And he was Just a total contrarian at the time, the world kind of evolved this way, and being a huge proponent of open standards, and really believing that these interchange of technologies across services would, like, grow the whole market a lot faster than if they were to be siloed, and, you know, seeing the walls break down around SMS and stuff was a, that now it seems obvious, but at the time that wasn't obvious.

AI assessment note: “I'm such a John McFarlane fanboy having, I worked for him for like eight years”

Q I do want to discuss the transition. From operator to VC, we spoke about some of the founders that you've worked with. One founder that you backed, Alexandra Lola, before the interview, asked a very poignant question being, as an operator turned VC, what do you think characterizes your approach to really working with portfolio companies today?

A Yeah, I mean, my approach is based on the fact that I think I'm pretty fortunate to be a well-rounded exec at the startups that I worked at. So I ran engineering teams, product design teams, and marketing partnership teams. So I've seen all the kind of the critical bits of inside the startups and had to make all those decisions around how we organize and how we hire and how we plan and prioritize. And so I think my approach usually, since what I have to go on is that experience, I try to think of myself as an extension of their team. Think of myself as an embedded resource that's helping them think through all these decisions and Just like I did when I was an operator.

AI assessment note: “I try to think of myself as an extension of their team.”

Q I have to ask, what were the big challenges making the move in? And were there any really big surprises? Maybe kind of having that external view of what VC would be. Were there any big surprises on entering, on kind of realizing that vision?

A Yeah, I think the biggest challenge to me is if you spent 20 plus years working at startups, like I have You wake up every morning and you go move the ball forward on your thing, whatever that, you know, you work at a company and you have some plan and you go execute that plan or evolve the plan. And it's very clear how you can spend all of your time working to make that thing better. As a venture capitalist, I think the biggest challenge for me is just how do you spend your time? I mean, we're in the business of manufacturing serendipity, and that's very unclear to me how you do that. There's a lot of, so you wake up in the morning, you're like, I could read a bunch of stuff. I can listen to these things. I could talk to these people. I could go to this conference and it's unclear which one's going to be the most productive. That's a huge.

AI assessment note: “the biggest challenge for me is just how do you spend your time?”

Q I do have to ask though, Kevin, you mentioned your time at Twitter there, and a few stats. When you joined, there were less than 20 employees and a million users. So tell me, what were the big lessons from really seeing that first-hand hyper-scaling of Twitter?

A Yeah, I mean, my time at Twitter was incredible. I mean, it's like the opportunity of a lifetime to be part of something like that, that really changes the way information is, you know, distributed and consumed around the world. And it's amazing to me that over all these years, they still own that use case. No one's even come close to disrupting them for the Twitter use case. I think one of the challenges of hyperscaling company, especially Twitter, when you have a product that is used by so many people in so Focus and prioritization becomes a big challenge, and I think when you grow very quickly and you are fortunate enough to raise a lot of capital, it can sometimes make you lazy in how you make those hard decisions. When, if you're constrained more, you'd say, well, we can literally only do one or two things, but when you are growing fast and you have so many resources, it's easy to say, well, if we just had more Engineers, we could do more things, and then you end up not doing as many of those things as well as you should if you were constrained more.

AI assessment note: “Focus and prioritization becomes a big challenge, and I think when you grow very quickly”

Q You spoke about themes and theses earlier. Although you don't have one, as you said, very much founder-centric, you do have an instinct for, for consumer brands and creating great consumer brands. So I have to ask, what is a great consumer brand today, do you think? And what are the core tenets of that brand?

A Yeah, I think it's really interesting, this concept of brand that I think people are waking up to a little bit more, which is exciting. And, you know, I think the core tenets are, for me, fundamentally, it's not One or five things. It's like a thousand little things that make your brand. Everything from the descriptive language to the aesthetics and the colors and that, like all the little design details make your brand. The imagery, the product experience, the subtle language you use in your product, I think really, really builds a brand. I mean, I think Twitter was a great example of that. Very much a consumer internet product that has a Brand persona, right? And we could sit here and probably come up with, like, 20 things that make that so, but we both know instinctively that it's true. Even a product like Facebook is one of the most impressive companies and products of all time. It doesn't really have as much of a brand persona as a Twitter does, and I think it's because of all those little, little things.

AI assessment note: “it's like a thousand little things that make your brand.”

Q I have to ask, what were the big challenges making the move in? And were there any really big surprises? Maybe kind of having that external view of what VC would be. Were there any big surprises on entering, on kind of realizing that vision?

A Yeah, I think the biggest challenge to me is if you spent 20 plus years working at startups, like I have You wake up every morning and you go move the ball forward on your thing, whatever that, you know, you work at a company and you have some plan and you go execute that plan or evolve the plan. And it's very clear how you can spend all of your time working to make that thing better. As a venture capitalist, I think the biggest challenge for me is just how do you spend your time? I mean, we're in the business of manufacturing serendipity, and that's very unclear to me how you do that. There's a lot of, so you wake up in the morning, you're like, I could read a bunch of stuff. I can listen to these things. I could talk to these people. I could go to this conference and it's unclear which one's going to be the most productive. That's a huge.

AI assessment note: “the biggest challenge for me is just how do you spend your time?”

Q I do have to ask though, Kevin, you mentioned your time at Twitter there, and a few stats. When you joined, there were less than 20 employees and a million users. So tell me, what were the big lessons from really seeing that first-hand hyper-scaling of Twitter?

A Yeah, I mean, my time at Twitter was incredible. I mean, it's like the opportunity of a lifetime to be part of something like that, that really changes the way information is, you know, distributed and consumed around the world. And it's amazing to me that over all these years, they still own that use case. No one's even come close to disrupting them for the Twitter use case. I think one of the challenges of hyperscaling company, especially Twitter, when you have a product that is used by so many people in so Focus and prioritization becomes a big challenge, and I think when you grow very quickly and you are fortunate enough to raise a lot of capital, it can sometimes make you lazy in how you make those hard decisions. When, if you're constrained more, you'd say, well, we can literally only do one or two things, but when you are growing fast and you have so many resources, it's easy to say, well, if we just had more Engineers, we could do more things, and then you end up not doing as many of those things as well as you should if you were constrained more.

AI assessment note: “Focus and prioritization becomes a big challenge, and I think when you grow very quickly”

Q You spoke about themes and theses earlier. Although you don't have one, as you said, very much founder-centric, you do have an instinct for, for consumer brands and creating great consumer brands. So I have to ask, what is a great consumer brand today, do you think? And what are the core tenets of that brand?

A Yeah, I think it's really interesting, this concept of brand that I think people are waking up to a little bit more, which is exciting. And, you know, I think the core tenets are, for me, fundamentally, it's not One or five things. It's like a thousand little things that make your brand. Everything from the descriptive language to the aesthetics and the colors and that, like all the little design details make your brand. The imagery, the product experience, the subtle language you use in your product, I think really, really builds a brand. I mean, I think Twitter was a great example of that. Very much a consumer internet product that has a Brand persona, right? And we could sit here and probably come up with, like, 20 things that make that so, but we both know instinctively that it's true. Even a product like Facebook is one of the most impressive companies and products of all time. It doesn't really have as much of a brand persona as a Twitter does, and I think it's because of all those little, little things.

AI assessment note: “It's like a thousand little things that make your brand.”