The Exchanges

Q Guys, how do you think about the decision to build your own models? I'm just intrigued on like, you know, I asked Scott at Atlassian that question. He was like, no, it's not our call. We don't need to.

A Actually, I think that's, that's sort of the right answer is you should build models if you're the best company in the world to build them. And so, um, you know, for us, it was like, You know, who, who's going to build a better imaging model? You know, we, we've got the, the advantage in terms of understanding the customer's use cases. We have the data, you know, no one should build a better imaging model than Adobe. And so we're like, okay, we need to set out and make sure we hold ourselves to that level. But when it comes to like building a massive LLM to Gustav's point, like let's partner with the LLMs of the world that, that, you know, do this, you know, as a business. And I think it's as simple as that. So when we're looking through all the different vectors, you know, we want to build the models that we believe are our competitive advantage is to, is to be able to build and be best at, and then those others we should partner with.

AI assessment note: “you should build models if you're the best company in the world to build them.”

Q In product reviews and product testing, how do you think about intuition and gut versus data, customer feedback, and usage?

A It's a great question. It's something I think about all the time, and you know, the analogy that I use is that intuition is what brings you to a mountain to climb. Data is what helps you climb it. You know, you think about it that way, oftentimes what you really believe the customer will need is not something that the customer knows they need yet. And, I mean, I experienced this myself with Behance. We had a focus group back in 2006, and we got a group of creatives together, um, that we wanted to build a portfolio network for. You know, we asked folks, do you need, you know, we described what we were building, and universally everyone said, no, I don't need that. And we said, why? And they're like, well, there's already MySpace, there's already DeviantArt, there's already LinkedIn, like, why do I need yet another place to build a profile? And we're like, oh, ok, well, instead of giving us feedback on what we want to build for you, tell us, like, what you're struggling with. And they're like, oh, well, that's easy. You know, I never get attribution for my work. My portfolio is always out of date. You know, my projects within my portfolio have no way of reaching people based on what they're interested in hiring someone for. You know, I, there's no way of me posting the stuff that I've done for particular agencies that were for other brands. Like they go through a whole list of th…

AI assessment note: “intuition is what brings you to a mountain to climb. Data is what helps you”

Q In product reviews and product testing, how do you think about intuition and gut versus data, customer feedback, and usage?

A It's a great question. It's something I think about all the time, and you know, the analogy that I use is that intuition is what brings you to a mountain to climb. Data is what helps you climb it. You know, you think about it that way, oftentimes what you really believe the customer will need is not something that the customer knows they need yet. And, I mean, I experienced this myself with Behance. We had a focus group back in 2006, and we got a group of creatives together, um, that we wanted to build a portfolio network for. You know, we asked folks, do you need, you know, we described what we were building, and universally everyone said, no, I don't need that. And we said, why? And they're like, well, there's already MySpace, there's already DeviantArt, there's already LinkedIn, like, why do I need yet another place to build a profile? And we're like, oh, ok, well, instead of giving us feedback on what we want to build for you, tell us, like, what you're struggling with. And they're like, oh, well, that's easy. You know, I never get attribution for my work. My portfolio is always out of date. You know, my projects within my portfolio have no way of reaching people based on what they're interested in hiring someone for. You know, I, there's no way of me posting the stuff that I've done for particular agencies that were for other brands. Like they go through a whole list of th…

AI assessment note: “intuition is what brings you to a mountain to climb. Data is what helps”

Q momentum that has the potential to fade out and become mortal compared to momentum that has the potential to turn into, let's say, a benchmark investment, Uber. You know, the momentum was there, I think, quite early from the start, wasn't it? And that has obviously skyrocketed and continued and continued. Is there a, is there a kind of transition point where it becomes clear that the momentum isn't dying?

A Well, when there is a increasing level of benefit from using a product over time, I feel like that's sustained momentum versus you get this big hit, you know, it's, it's fun. It's cool. I mean, like Pokemon go, for example, right. Is something that just got a ton of momentum super quickly, but it wasn't like the more you used it, the better it became. It was sort of a novelty that at least for me began to fade. Whereas you look at a network effect driven business like Uber, where The more people who are using it, the more drivers, the more drivers, the better the service, the better the service, the more people that use it. And so I think when you see momentum, you want to dig into whether or not it's being driven by novelty, and something that is really, really exciting and cool, but doesn't necessarily aggregate increasing amounts of value over time of use.

AI assessment note: “when there is a increasing level of benefit from using a product over time”

Q I'm super pleased you touched on some of the products there, because I want to deep dive on one aspect that you particularly love in terms of product, And that's the first mile. So, so for those that don't know, what's the first mile, and why do you feel that the product's first mile is always an afterthought nowadays?

A Well, the first mile of a product includes the onboarding to the product, the default user states you get when you first open the product, and when you start to go through the screens. The failure of the first mile for most products is that the teams fail to remember that every user in his or her 15 seconds is lazy, vain, and selfish. They're lazy in the sense that they don't want to read anything. They don't want to learn anything. They're vain in the sense that, gosh, you know, if I'm going to do this new thing, it better make me look good quickly. And they're selfish in the sense that even if there's something better for the collective by using this product, at first it better serve me because I've got very little time. You know, I'm busy with my life and my work and my family, and I just don't have the tolerance for anything unless it's going to help me right now. Now, of course, you want to build a more deep relationship with customers so that there's a long-term benefit. And a lot of Entrepreneurs struggle because they are always focused on that long-term gain from using a product, and they're always trying to get people invested in the product in order to get that benefit, when in fact, they should just be focusing on the first mile. They should make sure that a customer can get in, can see something in it for themselves, they know why they're there and what to do next, …

AI assessment note: “the first mile of a product includes the onboarding to the product”

Q most broad, but also kind of important, which is fundamentally we're all told that AI changes everything that we do. When we apply that to product, what do we think are the most significant ways that AI will change the product development process, specifically on the product development side? What will change specifically with AI? And I just want to throw that out there so anyone can jump on it.

A Well, I mean, I'm sure we're all experimenting with, um, with GitHub co-pilot in our engineering teams, and there will certainly be, you know, an improvement in both the productivity of developing code and products and also testing and, um, you know, and identifying and reconciling bugs and that sort of thing. But the only other thing I would throw in there is that when you're developing the interface of a product, You are oftentimes trying a few different approaches to find the one that works best. And that just takes a lot of time, uh, to have three or four different options and, you know, and explore, but then, you know, stop going down that path and go down another path. And then fast forward now into, you know, today into the future, we're in a world where AI will suggest alternative scenarios. You can try variations and just look and, you know, with the mistake of the eye, find a better solution. That, or at least something you want to A-B test. And so I think that the product development process, you know, will, the products will become much better, frankly, you know, just with, with fewer cycles, we'll find better solutions.

AI assessment note: “AI will suggest alternative scenarios. You can try variations and just look”

Q Guys, how do you think about the decision to build your own models? I'm just intrigued on like, you know, I asked Scott at Atlassian that question. He was like, no, it's not our call. We don't need to.

A Actually, I think that's, that's sort of the right answer is you should build models if you're the best company in the world to build them. And so, um, you know, for us, it was like, You know, who, who's going to build a better imaging model? You know, we, we've got the, the advantage in terms of understanding the customer's use cases. We have the data, you know, no one should build a better imaging model than Adobe. And so we're like, okay, we need to set out and make sure we hold ourselves to that level. But when it comes to like building a massive LLM to Gustav's point, like let's partner with the LLMs of the world that, that, you know, do this, you know, as a business. And I think it's as simple as that. So when we're looking through all the different vectors, you know, we want to build the models that we believe are our competitive advantage is to, is to be able to build and be best at, and then those others we should partner with.

AI assessment note: “you should build models if you're the best company in the world to build them.”

Q Uh, uh, tell me, uh, Scott, what have you changed your mind on in the last 12 months?

A The, the need for centralization, you know, and where things should and shouldn't be centralized. Like, I always go back and forth, honestly, on this. You know, there have been periods of time where I felt like design needed to be in different organizations because people had to prioritize and properly resource design for their business. And then recently I re-centralized design in one organization because our strategy, you know, required it. And I guess one of the things I'm learning is that sometimes You know, you make a completely opposite decision at different times in the same business because the playbook is different. And we typically don't think that way. We like when we make a huge decision and it's like, this is the way it's going to be. We just stick to it because we almost think like it's first principles, but you just have to be willing to discard the playbook consistently.

AI assessment note: “The, the need for centralization, you know, and where things should and shouldn't be centralized.”

Q Do you guys not find that inherently concerning? I think every company on this call is a public company. When you don't have the control of the outcome, and the outcome could be a hallucination, is that not concerning to you when you don't control the outcomes?

A Well, it's funny. I mean, you know, in, in some ways, listen, for some, for some practices hallucination, hallucination is a bug, but in some areas it's also a feature, right? So if I'm trying to discover some cool new music, I mean, I can imagine that might be a feature as opposed to a bug. You know, when you're trying to You know, when you're trying to do generative fill in Photoshop and imagine what's behind an object or, you know, extending the frame of a photo, hallucination is actually a feature. And if you get the wrong answer or something you don't like, you can just, you know, run it again. So I think it is a bigger problem, though, in, in applications that really, you know, are mission critical around, you know, writing NDAs, you know, for legal purposes or, you know, where, where hallucination actually could get you in trouble.

AI assessment note: “for some practices hallucination is a bug, but in some areas it's also a feature”

Q most broad, but also kind of important, which is fundamentally we're all told that AI changes everything that we do. When we apply that to product, what do we think are the most significant ways that AI will change the product development process, specifically on the product development side? What will change specifically with AI? And I just want to throw that out there so anyone can jump on it.

A Well, I mean, I'm sure we're all experimenting with, um, with GitHub co-pilot in our engineering teams, and there will certainly be, you know, an improvement in both the productivity of developing code and products and also testing and, um, you know, and identifying and reconciling bugs and that sort of thing. But the only other thing I would throw in there is that when you're developing the interface of a product, You are oftentimes trying a few different approaches to find the one that works best. And that just takes a lot of time, uh, to have three or four different options and, you know, and explore, but then, you know, stop going down that path and go down another path. And then fast forward now into, you know, today into the future, we're in a world where AI will suggest alternative scenarios. You can try variations and just look and, you know, with the mistake of the eye, find a better solution. That, or at least something you want to A-B test. And so I think that the product development process, you know, will, the products will become much better, frankly, you know, just with, with fewer cycles, we'll find better solutions.

AI assessment note: “we're in a world where AI will suggest alternative scenarios”

Q Uh, uh, tell me, uh, Scott, what have you changed your mind on in the last 12 months?

A The, the need for centralization, you know, and where things should and shouldn't be centralized. Like, I always go back and forth, honestly, on this. You know, there have been periods of time where I felt like design needed to be in different organizations because people had to prioritize and properly resource design for their business. And then recently I re-centralized design in one organization because our strategy, you know, required it. And I guess one of the things I'm learning is that sometimes You know, you make a completely opposite decision at different times in the same business because the playbook is different. And we typically don't think that way. We like when we make a huge decision and it's like, this is the way it's going to be. We just stick to it because we almost think like it's first principles, but you just have to be willing to discard the playbook consistently.

AI assessment note: “The, the need for centralization, you know, and where things should and shouldn't be centralized.”

Q I mean, respectfully, All three of you have moved really fast. My question is, like, is it kind of old BS that incumbents can't move fast? How have you guys been able to move so fast to embrace it? Scott, you talked about kind of the, you know, Cambrian explosions or Cambrian waves and jumping. How do you move so fast at scale, and is it BS that incumbents can't?

A Well, here's the thing. I mean, every platform shift is not the same. Right? They're all different. And if you're going from on-premise software to delivering in the cloud, that is a major, major transition that I can imagine many incumbents would struggle to do in a way as fast as a startup could do. And maybe that's why startups totally led the pack in terms of cloud alternatives to on-premise software in the past. And then you, mobile was probably the same sort of thing. Different stack of developers, You know, totally different go to market in some cases, different relationships with Apple app stores, and like, you know, there were so many differences. But with AI, I'm not actually sure that as a platform shift, which it certainly is, there are as many, um, differences in how a company facilitates, you know, and, and leverages that platform shift. Because, you know, when someone comes into Photoshop and they have an image that they want to change, right? If I can just give them a default bar that just shows up where they can just articulate what they want instead of using all the knobs and bells and whistles of Photoshop that have accumulated over the last 40 years, right? That is like a very incredible way of disrupting Photoshop to some degree. I don't have to build a net new company and a net new product from zero to one in order to reimagine Um, the capabilities of Phot…

AI assessment note: “every platform shift is not the same... with AI, I'm not actually sure”

Q Sorry to, again, convene me, but what makes a great first mile experience versus an average?

A Oh, wow. Two comments. You know, one is that as a great, great product leader, there are three questions you should ask in every screen you look at to ensure that it is accessible and navigatable for new customers. Right? The first is, how did I get here? What do I do now? And then what do I do next? Right? So those are the three questions that you need to ask. What you'll often find if you look at every screen of a product experience is that there are many moments where you don't know how you got there, or you're not sure what to do, and it's not clear what you're actually supposed to do next. And that means that the object model is broken. It means that the breadcrumbs aren't there, that someone didn't see, whether it's through an animated sequence or some sort of experience design issue in the product. They don't know They don't have their orientation. It's kind of like me taking you on a car ride, dropping you off in the middle of somewhere with your blindfold on and being like, okay, now figure out what to do. You're like, first of all, I don't know how I got here. I'm not sure what I'm supposed to do here, and I don't even know which way is north. Why do we let our customers in a digital experience get lost, you know, is wild to me, and I think that if you're a great product leader always is, you know, making sure that the compass exists in every moment of the product exp…

AI assessment note: “there are three questions you should ask in every screen you look at”

Q No, I do agree. But I do want one final question before we move into my favorite of any interview being the quickfire. And it's a great summary question with the book in mind. We touched on some investor topics there. So how's the work with the book? And everything around that really influenced your work as an investor and the mindset that you bring to new opportunities today.

A Well, the funny thing is, is that this writing is really for me. You know, I like to synthesize the things that I learn, things that I learned the hard way. I like to make sense of it. And I typically do that by either sharing it with others on social media or writing it down or both. And to me, it just helps, you know, it helps it sink in. And in some ways it builds my own instincts and becomes kind of the gravity or, you know, the magnet for my own core conviction when I meet People or products that get me super excited or when there's a decision that needs to be made and I want to have, you know, the energy to execute it in full force and to get people to buy in and to keep us loyal to the decision once it's made. I just think all of this stuff that I included in the messy middle, you know, these are things that have become tactics that I also turn to or those that I learned from people that I interviewed, you know, when putting the book together, but collectively, like it's all in there because it made the cut for me. And I think also, by the way, I think it's refreshing for entrepreneurs. I get so many pitches these days where people talk about the fact that they're in their messy middle. First of all, it's great that we start having a truthful exchange from the offset as opposed to we're going to change the world. We're building this. It's amazing. Customers love us. It's…

AI assessment note: “builds my own instincts and becomes kind of the gravity or, you know, the magnet”

Q No, I do agree. But I do want one final question before we move into my favorite of any interview being the quickfire. And it's a great summary question with the book in mind. We touched on some investor topics there. So how's the work with the book? And everything around that really influenced your work as an investor and the mindset that you bring to new opportunities today.

A Well, the funny thing is, is that this writing is really for me. You know, I like to synthesize the things that I learn, things that I learned the hard way. I like to make sense of it. And I typically do that by either sharing it with others on social media or writing it down or both. And to me, it just helps, you know, it helps it sink in. And in some ways it builds my own instincts and becomes kind of the gravity or, you know, the magnet for my own core conviction when I meet People or products that get me super excited or when there's a decision that needs to be made and I want to have, you know, the energy to execute it in full force and to get people to buy in and to keep us loyal to the decision once it's made. I just think all of this stuff that I included in the messy middle, you know, these are things that have become tactics that I also turn to or those that I learned from people that I interviewed, you know, when putting the book together, but collectively, like it's all in there because it made the cut for me. And I think also, by the way, I think it's refreshing for entrepreneurs. I get so many pitches these days where people talk about the fact that they're in their messy middle. First of all, it's great that we start having a truthful exchange from the offset as opposed to we're going to change the world. We're building this. It's amazing. Customers love us. It's…

AI assessment note: “it builds my own instincts and becomes kind of the gravity or, you know, the magnet”

Q Well, you are very kind, but I would love to start, and for those that maybe missed our first interview, talk to me, Scott. How did you make your way into the world of startups and investing and come to have the dual head of CPO at Adobe and venture partner at Benchmark?

A It's a confusing series of identity explorations. Well, you know, listen, it's funny because I've had the experience Experience now as a startup entrepreneur bootstrapping for five years, a venture backed entrepreneur, building something, going through an acquisition, big company, being absorbed and dealing with all the issues around getting acquired and making sure that that works out in a positive way for the whole team and the product. And then took my foray into formal venture capital. I think I learned a tough lesson, which is just because everyone says you should do something doesn't actually mean you should do it. I've been an angel investor for, you know, many years now and have had some great experiences. Experiences working with companies, and I said to myself, well, I should be in venture capital, and I should join an incredible firm like Benchmark, and this is the next 15 years of my life, and then I felt quite quickly like I had hung up my spurs, and my partners and I knew this is not what I was meant to do. I actually wanted to still build teams and products, and I actually feel like I'm a better investor in the early stages of products by being in the craft as well, so them giving me the opportunity to describe my own role, which I made into a venture partner role, which is a somewhat ambiguous But it was perfect for what I wanted to continue doing, you know, wit…

AI assessment note: “made into a venture partner role... and then some as chief product officer at Adobe”

Q Now, naturally as a massive venture nerd and inquisitive person, I have, I have actually a ton to unpack from there. One, one that really struck me early was you said about the transition from bootstrap To VC. How was that for you as an entrepreneur? And what were the differences then that you saw when you made the transition?

A Well, I think when you're bootstrapping a business, you get a tremendous feel for the granularity of your business, the money coming in, the money coming out, the true cost of every decision that you make. And it's a very healthy way to build a sustainable business because you feel in real time the impact of every decision you make. When you get venture capital, you get this dry powder. You know, you get to think longer term and make a lot of decisions that may not be scalable or, or, or may actually interfere with profitability, but you're doing so in exchange for a long-term return. And I think we all take for granted the ability to do that and, and sort of, and some of the dangers actually with being able to exercise and operate a business without a real relentless focus on the bottom line on a day-to-day basis. So I, I benefited from the discipline, but of course I also benefited from being able to scale and grow more quickly once we had venture capital.

AI assessment note: “I benefited from the discipline, but of course I also benefited from being able to scale”

Q Now, naturally as a massive venture nerd and inquisitive person, I have, I have actually a ton to unpack from there. One, one that really struck me early was you said about the transition from bootstrap To VC. How was that for you as an entrepreneur? And what were the differences then that you saw when you made the transition?

A Well, I think when you're bootstrapping a business, you get a tremendous feel for the granularity of your business, the money coming in, the money coming out, the true cost of every decision that you make. And it's a very healthy way to build a sustainable business because you feel in real time the impact of every decision you make. When you get venture capital, you get this dry powder. You know, you get to think longer term and make a lot of decisions that may not be scalable or, or, or may actually interfere with profitability, but you're doing so in exchange for a long-term return. And I think we all take for granted the ability to do that and, and sort of, and some of the dangers actually with being able to exercise and operate a business without a real relentless focus on the bottom line on a day-to-day basis. So I, I benefited from the discipline, but of course I also benefited from being able to scale and grow more quickly once we had venture capital.

AI assessment note: “I benefited from the discipline, but of course I also benefited from being able to scale”

Q And you said about the big learnings then, when you made that shift into benchmark and with the onboarding process, what were the big learnings that were really striking for you in the early days?

A Venture capital and investing in general is a business of exceptions, and whenever you talk to any, uh, seasoned investor about some of their greatest hits, you know, they'll tell you that the Team didn't look right, or the market seemed too small, or, you know, there are a lot of things that struck them as off-putting when they made the investment, but they made it anyways. And then they'll cite something that just pushed them over the edge to warrant an exception in the investment that they made. So that's one point. Then the counterpoint is that it's all about pattern recognition and seeing the same thing you've seen before and, and leveraging the past to predict the future. And so you have these directly opposing series of forces. That are supposed to dictate how you act and make decisions as an investor. And I think the learning that I had from the many conversations we had and continue to have as a team looking at potential investments, you know, you start to learn how to weigh the exceptions versus the rules and how you probe and your own values as an investor and a person that allow you to double down on something you're unsure about or stay away from something else.

AI assessment note: “you start to learn how to weigh the exceptions versus the rules”

Q In terms of another shift, though, that you mentioned there, and it was where you mentioned your angel investing and then the transition to benchmark. How did that transition affect your investment-making mindset?

A Good question. I think as an earlier stage angel seed investor, it's all about investing in the potential of a product or the potential of a team. When you start to do more traditional venture capital And certainly venture capital at the benchmark level level. It's a lot more, or it's also about momentum because, um, you know, there are a lot of great ideas and great teams and great aspirational products out there, but there is nothing more promising than, than something that's already getting momentum. Now, sometimes it can only be in a specific vertical or in a specific country or with a specific demographic of people, but nevertheless, it's when you have momentum, it's, it's, you know, it's, it's something that you can clearly capitalize on. So it was hard for me in some ways to, Start focusing more on the measuring of the momentum side than anything else.

AI assessment note: “Start focusing more on the measuring of the momentum side than anything else.”

Q And so if we apply it to you, as you said, you're, you're not a traditional VC. You're much more hands-on. You're a builder. You're building again now with the kind of stealth startup. How can you and then other creators then optimize the onboarding process? What are the pillars that they should focus on?

A Well, you have to consistently go through it yourself. And, you know, you'd be surprised how many teams don't revisit it because they, in fact, a lot of teams do it last, you know, right before they launch something, they Quickly do the onboarding, you know, and then after it's launched and they never look back. So I think the first thing you'd have to do is read to continually reinvent your onboarding. Um, watch other customers use your product, really understand from analytics what people are doing and why they're not getting through and focus on one little bit at a time. You know, why are they getting stuck here? Can we remove this? Can we remove that? Let's not ask the user for so much information at the expense of getting them through the funnel. Let's just Find a way to deliver a great service without that information, and then garner it over time from regular use. Those are the types of principles that I think are helpful in the first mile.

AI assessment note: “continually reinvent your onboarding. Um, watch other customers use your product”

Q So if we take from the first mile now to the middle, and I love the fact that you love the first mile of the product, and then you have a fascination with the journey in between the entrepreneurs. It's a nice correlation. But talk to me, what do you mean by this statement, the journey in between, and why, why does it fascinate you so much?

A Well, it fascinates me most. Actually, is how obsessed everyone is with the start and the finish of every journey. If you look at all media, it's basically about the founding, the financing, and then the inevitable bankruptcy or shutdown or acquisition or IPO. And we have this obsession with the starts and finishes because they're easy to summarize, they're motivating, they're pithy, yet they mean or really teach us nothing. What really makes the difference in any sort of venture is your ability to endure everything in between the anonymity, The struggle, the lack of financing at times, the failed products and the iteration and during all of that as a team and personally is very challenging. And then optimization. How do you not only optimize your product and the onboarding and everything else we just discussed, but also how do you optimize the way your team works and functions and the culture and the way you actually approach your work and, uh, and perform. It's, it's just, we, there's just not as much discussion and coverage and Over the most critical insights for the journey in between that endurance and optimization phase. And so that's what, that's what I'm really interested in because I think that's what makes all the difference.

AI assessment note: “What really makes the difference in any sort of venture is your ability to endure”

Q Do you guys not find that inherently concerning? I think every company on this call is a public company. When you don't have the control of the outcome, and the outcome could be a hallucination, is that not concerning to you when you don't control the outcomes?

A Well, it's funny. I mean, you know, in, in some ways, listen, for some, for some practices hallucination, hallucination is a bug, but in some areas it's also a feature, right? So if I'm trying to discover some cool new music, I mean, I can imagine that might be a feature as opposed to a bug. You know, when you're trying to You know, when you're trying to do generative fill in Photoshop and imagine what's behind an object or, you know, extending the frame of a photo, hallucination is actually a feature. And if you get the wrong answer or something you don't like, you can just, you know, run it again. So I think it is a bigger problem, though, in, in applications that really, you know, are mission critical around, you know, writing NDAs, you know, for legal purposes or, you know, where, where hallucination actually could get you in trouble.

AI assessment note: “it is a bigger problem, though, in, in applications that really, you know, are mission critical”

Q speak to many people. Everyone says that, you know, AI development, progression, technology, stellar, 10 out of 10. We're doing a great job. Enterprise adoption, about a negative four out of 10. Not good. Like, you know, I think as a stat, 32% of European corporates do not know what Slack is. So, That's concerning. How do you think about enterprise adoption keeping pace in any way with AI development?

A Well, I think it's probably good news that we're so early in the adoption curve, because that means that there's a lot of, you know, a lot of potential ahead, ahead, ahead for, for, for these companies. It doesn't happen linearly. You know, that's the thing. I think that the adoption happens in moments where there's like a step function You know, breakthrough, or people just suddenly realize that, I mean, a lot of enterprise selling also happens because of who else is buying it. When I'm trying to work with customers who are thinking about, are we, are we ready to change the way we do this? It's much easier when they hear about that company that has already changed the way they do this and how, you know, they're saving money and, and they're, and they're producing better output. It's like, oh, okay. Um, but, you know, I think that the part of, part of this is always about, Getting small teams in big companies to start to play with something, you know, and that's where I think enterprise sales can fall flat sometimes, and you have to have design partnerships with early customers as opposed to traditional sales, you know, to go into early customers and say, hey, I'm not even trying to sell you on this. I just want a small team that can start to, you know, play with some of our technology. We have this, uh, tune your own model capabilities now for Firefly, where Brands can use som…

AI assessment note: “adoption happens in moments where there's like a step function”

Q And then who's the biggest mentor to you, and how did the relationship come about?

A Um, I have different mentors, I think, for different parts of my life. There's some people like, um, you know, Seth Godin that I've only met with a handful of times, but every time he really makes me think and rethink the A lot of the, a lot of the decisions and career points in my life. There are people like John Maeda, who I see more frequently, where he always says things that I sometimes don't understand at the time, but then as they turn in my head, it's almost like Yoda. They gain on more meaning and make me think about things in different ways. So those are, those are a few, a few folks. But I also, you know, I try to not be too rigid in how I view mentorship. I think mentors can be younger, older, you know, different industries, just people who see things in a different way. And make you think.

AI assessment note: “I have different mentors, I think, for different parts of my life.”

Q Okay, super interesting question here, and not in the schedule, but having seen entrepreneurs operate from the side of the investor, has that changed how you think you'll operate going forward with your own startup?

A Well, I think that as an investor, you're always connecting the dots, and so you're, you're always trying to see the forest, right? And you're seeing trends, and you're, you're seeing things that don't work, and you're wondering, well, did it not work because it should never work, or did it not work because there was one little thing that was off, But that the general concept is still interesting. And, uh, and so it's a very much, you know, broad view connecting the dots approach. Whereas as an entrepreneur, you get a tunnel vision. In fact, you have to have tunnel vision in order to focus on one thing long enough to make it actually happen. And so I'm, I'm struck by the juxtaposition between the perspective of the investor and the wide lens and then the entrepreneur super focused. And I think the best practice for both of them, by the way, is to occasionally jump in or occasionally step back. As an investor, I try to Again, get my hands dirty with one particular area, or I try to pull a thread, I call it, uh, that is super interesting to me and learn everything I can about it. And as an entrepreneur, I, historic, I like to sometimes take a step back and sort of question whether my whole industry should exist in the first place. So I think that's, those are a few tendencies I've learned by being on both sides of the table.

AI assessment note: “those are a few tendencies I've learned by being on both sides of the table.”

Q So what makes you think this over, say, capitalist tendencies of private ownership?

A Well, I think that Buses and trains and, you know, some of the lowest common denominator offerings for transportation around the world are run by governments, and for the most part, not always, but for the most part, and I know that the planning and the scheduling of those utilities are done by the government agencies. I think that there are more efficient means to transport people around than laying train tracks and, you know, and having buses with, you know, certain types of electrical systems on top and whatever else. I think that Getting regular vehicles, you know, might be an alternative that some cities might consider in the future, and if so, why wouldn't those be operated off of some of the same software and planning infrastructure as city transportation today? And so, with the increased efficiency that autonomous vehicles would bring, you can't help but wonder if they'll all run off some scheduling software and programmed by the government versus a private company. That doesn't necessarily mean Something bad for companies like Uber and Lyft and others, because I think that the data that is being collected and the optimization of the routes based on the data is a moat, so to speak. And I think a lot of the technology for managing these dispatch systems and autonomous vehicles will be created by those companies. So their company, their businesses will change just like th…

AI assessment note: “Buses and trains and, you know, some of the lowest common denominator offerings for transportation around the world are run by governments”

Q And do you think it's more important now to focus than ever with the proliferation of apps that we have in the multi-million app store?

A I mean, the first mile is forever more important, especially as you try to engage more and more people. The, um, the other area that a lot of companies suffer around in the first mile is that the first mile for the first cohort of users of your product, it could even be the first hundred million users of your product. May be different from the next hundred million of your product or the next 10,000 users of your product because new groups of new users are different, right? And that's one of the mistakes we make is if you get the first mile, the onboarding, the initial user experience of a product perfect for a period of time, you have to continually revisit it and optimize it for new groups of new users with different psychographics, you know, different expectations, different ages. And, and I think, you know, that, that also creates a ceiling. For the potential, a lot of great products out there that get momentum, but then fail to, uh, sustain it.

AI assessment note: “the first mile is forever more important, especially as you try to engage”

Q So when you study it then with both an investor hat on with benchmark and then an entrepreneur hat on, what gives you hope then when you, when you study it for the future and what elements concern you potentially?

A Well, I think the, the more technology and startups is a sensation, the more likely we are to take our eye off the stuff that matters. And, you know, the entrepreneurs that I admire the most are just very practical heads down. They are obsessed with, I mean, I remember talking to Ben Silverman in the early days of Pinterest, asking him what his plans were for the next six months, thinking that he had a few sprints towards a few product features. And, you know, I expected sort of a typical answer like that. And he looked at me and he said, I want to have a better process. And I said, process in six months, you want to have a better process? And he was like, yeah, you know, he was really laying the groundwork for what he saw It had to be a very difficult journey, and he felt like investing and optimizing the process would be a great thing to focus on for the coming months, and it just struck me. I think a lot of great entrepreneurs think that way because they realize that it's, you know, it's the journey in between and surviving it that is really the difference between success and failure. So I think that's, you know, I think Silicon Valley actually confuses or dissuades people from focusing on the unsexy stuff that matters in exchange for all the headlines we're bombarded with. On a daily basis.

AI assessment note: “the more technology and startups is a sensation, the more likely we are to take our eye off”

Q How do you balance that then? In terms of the value investing on whether it's double down or not, is it something that you learn with the help of your teammates, or is it a gut instinct?

A I think that's certainly one of the greatest benefits of a partnership is having a group of people that you really respect and have a lot of affection for, but think extraordinarily differently. And, uh, you know, and one of the things I also took away from, you know, my, my role in the, in the partnership is just the importance of having a very different group of people around the table. I think that there's a lot of discussion in the world about, The benefits of diversity in any respect in any business or whatever, but I think it comes down to having extraordinarily different, extraordinary people around the table to, uh, to challenge you on your thinking, to push you to go against a pattern and invest anyways, in some cases, or, you know, or question momentum. Um, you know, oftentimes the trouble with momentum also is that when something has too much momentum too quickly, in my experience, at least it tends to fade out. And so it's, uh, again, it's this crazy business of, uh, always walking that fine line between, uh, Something to be an indicator or not.

AI assessment note: “one of the greatest benefits of a partnership is having a group of people”