The Exchanges

Q The challenge that I often face when I'm looking at that and product experiences like this is absolutely you have that gut punch, but it's the market timing question on adoption. How do you think about the dangers of market timing risk, even when you have that kind of transformational product experience for the consumer?

A Market timing, Typically relates to adoption forces, right? So you're asking the question of, will the pull, not your screaming at the market, but the market grabbing at your products be there? And there usually are antecedents, right? Preconditions for that market pull to fall into place. In the case of New Relic, we needed the cloud. We needed Ruby on Rails. We needed over time, you know, the move to cloud AWS and Microsoft deployments. Those were beyond our control. But we set the company up. If you look at the Series A, there were four people. Now, of course, we committed to Lou, and it was just Lou. And we managed our headcount and our expense load to be able to respond to the market forces without getting in front of them. And I think one of the bigger risks that's going on in 2021 is there's a lot of invested capital is going in to market preconditions that either don't exist or are still too early to support the economic development of the businesses. And so That was very conscious in 2007, 2008 for us. Cause we were going into the global financial crisis and we thought, okay, this is a terrible time to be trying to start a company, but by keeping it relatively tight, then allowed us to add in compound when those market forces became more visible. So market timing question was, will people want to ever have APM delivered in a cloud service? Back then it was a real quest…

AI assessment note: “we managed our headcount and our expense load to be able to respond”

Q look back at our last episode piece, he said, I'm always amused by VCs that say they look for big markets. And so I'd love to hear, kind of projecting your mind back to 2008, when doing the deal for New Relic, How did you evaluate and break down the market, I guess? And what excited you so much then when it wasn't the obvious market that it is today?

A Yeah, this was both an issue for the New Ellic investment as much as the Wiley investment. And the category, the APM, fell into the damned bucket of developer tooling. The conventional wisdom at the time, also when I invested in Wiley in 2001, was that developer tooling would never leave a significant business because, you know, they all tap out at about fifty million in revenue. And there were plenty of examples of that, of dev tools that Borland had acquired or CA had acquired that tapped out. And I think so much of the art of early stage venture is to ask the question of, can you unlock consumption? Can you tap into a latent potential energy of demand that can be made kinetic through a product experience that's radically easier to engage with and more immediately convincing minute zero minute one than it is in its current form. So The theory behind APM, Application Performance Management, was that there were billions and billions of dollars of software written every year. They were going into the world and torturing their users, either by slow response times, you have everything from lag to brownouts to full blackouts of sites going down, and that developers were being blocked from seeing that in the world. And the idea behind APM, back to Wiley, was we can give people the consciousness, the awareness of how their products do In the wild. And I think every developer has that…

AI assessment note: “can you unlock consumption? Can you tap into a latent potential energy of demand”

Q I want to start today really with a focus on the origin story as we unpack the series A that you left for New Relic way back in 2008 now, so let's start with the story and some history, and I heard that it all originated on a Golf course. So I'm going to let you take it from there. What was the story, Peter, from that golf course moment?

A Yeah, it is embarrassing in a way because I don't dislike golf, but I'm no good at it, and it's exceedingly unlikely you'll ever find me on a golf course. So the fact that that isn't the origin of this company is sort of hilarious to me and a little bit embarrassing. So Lou, I had known since 98, 99 when I was at Stanford. I'd met him and was fortunate enough to back him at Wiley, where he was the CEO of Of a generation prior to New Relic application performance management product. Wiley had sold to computer associates, and Lou was sufficiently enjoying his time off, which led him to invite me to play golf with him. And so we're both not very good. Now Lou's better than me, and doesn't stop the fact that about halfway through the golf round, we start to drink. Maybe two or three beers in could have been more. He starts to share with me his ideas about a new company. And one of the things that Lou had earned after Wiley was economic freedom. So he didn't need to have investors. He didn't need to have a board. And Lou was positively giddy about Ruby on Rails. He had a sense of sort of like butterflies in his stomach excitement about starting a new company in this new area. And with sort of a Cheshire cat grin, he said, and I don't need a board and I don't need investors. And so I had another probably beer and contemplated my relevance in this universe and then challenged him. And…

AI assessment note: “halfway through the golf round... He starts to share with me his ideas”

Q I want to start today really with a focus on the origin story as we unpack the series A that you left for New Relic way back in 2008 now, so let's start with the story and some history, and I heard that it all originated on a Golf course. So I'm going to let you take it from there. What was the story, Peter, from that golf course moment?

A Yeah, it is embarrassing in a way because I don't dislike golf, but I'm no good at it, and it's exceedingly unlikely you'll ever find me on a golf course. So the fact that that isn't the origin of this company is sort of hilarious to me and a little bit embarrassing. So Lou, I had known since 98, 99 when I was at Stanford. I'd met him and was fortunate enough to back him at Wiley, where he was the CEO of Of a generation prior to New Relic application performance management product. Wiley had sold to computer associates, and Lou was sufficiently enjoying his time off, which led him to invite me to play golf with him. And so we're both not very good. Now Lou's better than me, and doesn't stop the fact that about halfway through the golf round, we start to drink. Maybe two or three beers in could have been more. He starts to share with me his ideas about a new company. And one of the things that Lou had earned after Wiley was economic freedom. So he didn't need to have investors. He didn't need to have a board. And Lou was positively giddy about Ruby on Rails. He had a sense of sort of like butterflies in his stomach excitement about starting a new company in this new area. And with sort of a Cheshire cat grin, he said, and I don't need a board and I don't need investors. And so I had another probably beer and contemplated my relevance in this universe and then challenged him. And…

AI assessment note: “halfway through the golf round... He starts to share with me his ideas”

Q Can I ask, when you talk about the kind of the kinetic energy there, when you think about that transition in terms of the product experience, is that a gradual transition or is that actually quite a sudden product update that causes a momentary shift in terms of that transition to kinetic energy?

A I think the great products are gut punch, where you just say, wow, I can't unsee that. And it goes from like the consumer experience we used to talk about pay at the pump, right? But that was the kind of feeling you had when you ordered your first Uber and certainly the feeling that I think developers have when they deployed New Relic on a Rails application. I remember the conversation with Toby and his eyes sparkled and said, this product is magical. What it allows our developers to get access to and see versus the alternatives, which are so radically deficient compared to the gut punch feeling of one of these great product inventions. So the beginning of New Relic was that visceral. It was that immediate. Now, That didn't mean it served every market. In fact, it was very narrowly constrained to the Rails market, to Ruby on Rails, and the virtual machine that it ran with. And so what then became an issue of, okay, how do you want to have that gut punch? How do you spread that to as big a population as possible over time without losing the immediacy of that product experience as you push out into Java, into Python, into PHP? And we, you know, we debated all these different directions we could go. What we didn't debate is that the gut feel, gut punch sort of product joy was Had to be primary in the experience of the developer versus the current market that they were competing in…

AI assessment note: “I think the great products are gut punch, where you just say, wow”

Q hear is that when you think about the incredible twelve-year journey you had on the New Relic board, how do you think that experience in particular changed how you think about great board management? And this could be from the founder perspective in terms of how Lou managed the board so efficiently, or from your own perspective in terms of what it takes to be a great, great board member.

A The original New Route board stabilized at about three people for, I want to say, the first five years. I think we're accountable to the fact that it wasn't diverse. It was Lou, myself, and Dan from, at the time, Trinity Ventures. Yet there was something that I think was elusive in the dynamic, and to me, precious, around a very transparent, honest, and direct set of conversations about the state of the business. We didn't sit through PowerPoint slides, and I've talked about the Power of having written narratives. The unsung hero of New Relic's financial success is Mark Sackleb and the CFO. Lou brought in early, and Mark would write a crisp, succinct narrative with the team that laid out the core business metrics with the story behind them. We were able to, as issues surfaced in our consciousness, management team scaling, pricing pressure, competitive dynamics, have a very fluid conversation that felt like You were talking to not just people who had context and expertise, but that would stretch your thinking. And I think the really great boards, you come out and think, I wouldn't have thought about that if we hadn't had that conversation. So one of the things that I think we maintained through our addition of Sarah Fryer, who joined the board, Peter Curry, was that core culture of just being really direct and making it safe to be vulnerable, which is the key thing for Lou. The …

AI assessment note: “Power of having written narratives. The unsung hero of New Relic's financial success”

Q look back at our last episode piece, he said, I'm always amused by VCs that say they look for big markets. And so I'd love to hear, kind of projecting your mind back to 2008, when doing the deal for New Relic, How did you evaluate and break down the market, I guess? And what excited you so much then when it wasn't the obvious market that it is today?

A Yeah, this was both an issue for the New Ellic investment as much as the Wiley investment. And the category, the APM, fell into the damned bucket of developer tooling. The conventional wisdom at the time, also when I invested in Wiley in 2001, was that developer tooling would never leave a significant business because, you know, they all tap out at about fifty million in revenue. And there were plenty of examples of that, of dev tools that Borland had acquired or CA had acquired that tapped out. And I think so much of the art of early stage venture is to ask the question of, can you unlock consumption? Can you tap into a latent potential energy of demand that can be made kinetic through a product experience that's radically easier to engage with and more immediately convincing minute zero minute one than it is in its current form. So The theory behind APM, Application Performance Management, was that there were billions and billions of dollars of software written every year. They were going into the world and torturing their users, either by slow response times, you have everything from lag to brownouts to full blackouts of sites going down, and that developers were being blocked from seeing that in the world. And the idea behind APM, back to Wiley, was we can give people the consciousness, the awareness of how their products do In the wild. And I think every developer has that…

AI assessment note: “The theory behind APM, Application Performance Management, was that there were billions and billions”

Q of valuation, uh, comes up a lot for me in my role speaking to VCs, uh, and, and you said never turn down a company based on valuation because it's a mental trap. I, I do have to touch on this and price sensitivity is, Surely some rigidity has to be applied to ensure fund returning economics. How do you think about that in comparison to the investment decision-making process?

A Certainly, if you look at it as a relaxing of the constraint of having a point of view on potential value, it's not a good way to come at the investment question. And I think what you're trying to understand is, in my view, fundamentally, what's the full potential look like? And knowing that full potential is deeply irrational, like the chances that you would have I've come up with the idea that Facebook could be worth more than three hundred billion dollars when you saw the Series A pitch work. You would have been hauled away. You would have been asked to leave the firm and felt more like one to two billion. I would say that there was a pretty good case in the industry that Uber at the very beginning would struggle to be more than just a niche product for wealthy people in highly affluent urban environments, and the challenge then becomes, okay, knowing that the outer limits of possible are hard to imagine without being clinically insane, we have to find a fair A fair trade for us to know that we're going to get it wrong in terms of the full potential a number of times, but what matters the most is when we get it right, and the fund return dynamic is not defined by having purchased companies the right way. It's really defined by did we get involved, and this is the way Benchmark practices the business, but did we get involved with the three to five companies for that decade th…

AI assessment note: “the fund return dynamic is not defined by having purchased companies the right way.”

Q How have you seen yourself develop as a board member, and what have been the inflection points in your learnings?

A You know, I would say that my beginning tenure as a board member, I was awful. I had very strong points of view, which I freely communicated without much context. It, it, uh, I had Been blessed by working with David Strom, who's one of the founding partners at Greylock. And David pulled me aside a few times and encouraged me to exercise a little more of the listening, you know, part of my psyche. And I, I then, in a way that was, I think nothing less than transformational, became a student of great board members and interviewed a number of the people in the venture business who I really respected and, and entrepreneurs and said, what does it look like to be extraordinary at this? And so, you know, for years in, I went Onto a pretty steep learning curve, and I've ultimately concluded the Socratic method is far more effective than being didactic, so meaning Socratic of the form where you're inquisitive, asking questions, but really in your mind synthesizing, what are the two to three most important questions that I could ask, as opposed to the 15 that might be on my mind, and what I saw at Dora about that role is that you have a dynamic, and a great board has, you know, multiple perspectives that are, if you will, seeing the same phenomenon, and I think revealing more of it Through their diversity. But I think it's not just you being the great board member who's asking the right …

AI assessment note: “I've ultimately concluded the Socratic method is far more effective than being didactic”

Q Well, thank you so much. I'll pay you later. Um, but I, I would love to ask then, uh, You, you're trying to teach your eldest child in and out group bias. What does that mean in reality? I was intrigued.

A Yeah, there's a link which I would love for you to put up in your podcast on the implicit bias test, and it turns out that we all carry subconsciously fairly spectacular when revealed biases about people in the world. I think one of the defining traits of humanism is a eradication of the notion of the other, and the notion of the other is something that comes from these implicit biases, and they could be racial, they could be socioeconomic, They could be gender-based, and with my son specifically, you know, he's in school in Paris. I've tried to give him what I didn't necessarily get, which is an opportunity to be the one that crosses the divide when there's bias. They have a student who joined their school recently as a Mali refugee, and, you know, that student, I think, was, as he told me stories about it, not included into the core groups and cliques of the eight-year-old school ground, and what I begged of him was to be the one, and I thought, you know, we've all felt this in our past, the individual that crosses the divide To grab you and pull you in. Because I felt that for both that student, but also my son, that would be one of those life lessons that they could carry forward. And so concretely, that's what I've tried to do. And I think, you know, the rationale and logic behind it comes from this awakening that I think we've all gone through around our own biases and ho…

AI assessment note: “They have a student who joined their school recently as a Mali refugee”

Q hear is that when you think about the incredible twelve-year journey you had on the New Relic board, how do you think that experience in particular changed how you think about great board management? And this could be from the founder perspective in terms of how Lou managed the board so efficiently, or from your own perspective in terms of what it takes to be a great, great board member.

A The original New Route board stabilized at about three people for, I want to say, the first five years. I think we're accountable to the fact that it wasn't diverse. It was Lou, myself, and Dan from, at the time, Trinity Ventures. Yet there was something that I think was elusive in the dynamic, and to me, precious, around a very transparent, honest, and direct set of conversations about the state of the business. We didn't sit through PowerPoint slides, and I've talked about the Power of having written narratives. The unsung hero of New Relic's financial success is Mark Sackleb and the CFO. Lou brought in early, and Mark would write a crisp, succinct narrative with the team that laid out the core business metrics with the story behind them. We were able to, as issues surfaced in our consciousness, management team scaling, pricing pressure, competitive dynamics, have a very fluid conversation that felt like You were talking to not just people who had context and expertise, but that would stretch your thinking. And I think the really great boards, you come out and think, I wouldn't have thought about that if we hadn't had that conversation. So one of the things that I think we maintained through our addition of Sarah Fryer, who joined the board, Peter Curry, was that core culture of just being really direct and making it safe to be vulnerable, which is the key thing for Lou. The …

AI assessment note: “a very transparent, honest, and direct set of conversations about the state of the business”

Q Final one, Peter. What's your favorite story from working with New Relic and the incredible 12, 13 year journey that it was now?

A It's hard to distill that many experiences over that many years. I do think the moment that I remember most in hindsight was in the middle of financial crisis, 2009, we started missing our number. And I felt in one of those moments in a career where all the stars align, where you have a sense for serving a purpose that you're uniquely able to serve. And Lou had come to the board meeting really down, not sure of what it could become. And we were probably at three or four million in revenue. So it wasn't very big to be slowing down to breathe confidence into that room, into Lou, into the business to get through that trough. And that board meeting, he came out, and I think felt uplifted by our support for him. And in a sense, it prevented a spiral of psychology around we weren't going to be great, and elevated us back to the upwards virtuous cycle. I think that that sort of durable commitment is what defines the role we like to play.

AI assessment note: “the moment that I remember most in hindsight was in the middle of financial crisis”

Q allocation and comparing to this day, it was interesting when I had Bill on the show the first time, not with Howard Marks, but Solo, he said that his biggest challenge today is the oversupply of capital. Would you agree with Bill there? And you know, bluntly, I'm very nervous about it. Would you agree with Peter and me in terms of the concern and the nerves around the oversupply?

A No, I don't have that same fear. I personally think that oversupply of capital is historically a good thing for innovation insofar as it creates higher degrees of entropy. Therefore, you have more random mutations, if you think about it in a biological sense, for things that might not otherwise have been possible to become possible. The confluence of variables to create a compelling product experience, in many ways, are non-deterministic, and they come from experimentation. And so when you have more capital, you have more experimentation. The pernicious effects of too much capital, I think, show up principally in the later stages of a company's life, where you get categories that get flooded with capital, and then that could, in fact, Lead to uneconomic business models that aren't sustainable. But then the flip side of that is they also allow for foundations to be built that enable businesses that wouldn't otherwise be possible. So I think a lot of what's gone on, say, for example, local delivery and local businesses required an overabundance of capital to be able to create the critical mass to support high cash flow businesses. And so I don't think it's so black and white easy. The stage of capital that you're in, it matters intensely. And so right now we're, of course, you know, so far down the path of a 1516 year, one would say, bull market, that there are weird perversions …

AI assessment note: “No, I don't have that same fear. I personally think that oversupply of capital is”

Q do you call out in the board meeting and then have a constructive discussion around it with the great minds that you have around the table? Or do you actually go, this may be challenging for the founder to face having not prepared, but I don't want to put him on the spot in a certain way. How do you think about calling someone out or a founder out effectively?

A Well, I think we underestimate the social, emotional nature of any discourse, because I think we're humans at the end of the day, and we have natural emotional responses to critique. We can defense it. If you're threatened, and the emotions of fear take over, you're not going to hear the feedback. You may hear it an hour later, or a day later, a month later, but in the moment, the human response to critique is defense, and it takes a highly evolved founder to say thank you for that criticism. So, I think a huge part of doing our work is to be able to separate out the emotional reality of the moment, which is these people have killed themselves to create this board material. They're working their asses off every day, and we come in, and if we're full of critique, and believe me, this is a line I fear I've crossed one too many times, then it not only won't be heard, which means it's not effective feedback, but it can damage the ability to have a trust-based relationship. So a huge part of getting it right is something you can take out of the parenting books. I don't think it's discipline, but I do think it's, you start with validation, and you have to, in any situation, if something's gone off, or you think that we're not talking about a big issue, you need to validate the emotional space that the team is in, in a very real way, and so not just platitudes, but then I think you ea…

AI assessment note: “a huge part of getting it right is... you start with validation”

Q You said there about realizing full market potential. I do have to ask, and one of your investments being Snapchat, when the full market potential is so undefined, ephemeral messaging at the time of Snapchat's inception was, was barely even a market. So how do you view market creation with regards to this, uh, investment process and trying to assess the value of the market pre-investment?

A It centers almost entirely, at least in my case, on the quality of the entrepreneur. If an entrepreneur has a perspective, in the case of Evan at Snapchat, that there's something missing in the world that, that he wants to manifest and do it in a way where there's an authentic, unique point of view around what that is, and then something very deep, which is a, uh, hard to describe, but you Feel it, which is a sense of purpose to go do that. Then you have a hard time bounding and setting up a frame to say, okay, this is what it will be worth. I'm always amused by people who say invest in big markets because, you know, in many ways, by definition, the startup companies that do the best invest and get going in very narrow, almost ill-defined, if not completely invisible markets, you know, what was snap really doing with disappearing photos, 10 second photos for what it turned out to be, you know, late Teenage dominant female versus male. And you would have said, well, how big could that be? And I think any frame you would have applied would have missed the underlying phenomenon, which is you have a human being, a team, a company, you know, both Evan and Bobby as co-founders who had a point of view and the point of view, if you heard it, I mean, I'm telling you, if you felt it and heard it from Evan, 2000, well, gives you goosebumps. And specifically what I heard was we had lost, m…

AI assessment note: “It centers almost entirely, at least in my case, on the quality of the entrepreneur.”

Q How have you seen yourself develop as a board member, and what have been the inflection points in your learnings?

A You know, I would say that my beginning tenure as a board member, I was awful. I had very strong points of view, which I freely communicated without much context. It, it, uh, I had Been blessed by working with David Strom, who's one of the founding partners at Greylock. And David pulled me aside a few times and encouraged me to exercise a little more of the listening, you know, part of my psyche. And I, I then, in a way that was, I think nothing less than transformational, became a student of great board members and interviewed a number of the people in the venture business who I really respected and, and entrepreneurs and said, what does it look like to be extraordinary at this? And so, you know, for years in, I went Onto a pretty steep learning curve, and I've ultimately concluded the Socratic method is far more effective than being didactic, so meaning Socratic of the form where you're inquisitive, asking questions, but really in your mind synthesizing, what are the two to three most important questions that I could ask, as opposed to the 15 that might be on my mind, and what I saw at Dora about that role is that you have a dynamic, and a great board has, you know, multiple perspectives that are, if you will, seeing the same phenomenon, and I think revealing more of it Through their diversity. But I think it's not just you being the great board member who's asking the right …

AI assessment note: “I've ultimately concluded the Socratic method is far more effective than being didactic”

Q an article by Elad Gill on the end of cycles. And he stated that we're entering a period where, where everyone's looking for the next truly deep vein to explore. However, your recent investment in Zenly suggests you think there's potential runway in maybe the social vein that is somewhat considered the predecessor. I'm intrigued. How do you view the potential end of this tech cycle that we're currently in?

A You know, it's an interesting lens as you look at our investments as they cluster around trends or sectors. Or phenomenon. I think we end up putting a little bit more structure on the phenomenon than reality merits, meaning I think it's hard to say that any one of these companies is an instantiation of a trend and not something unique in and of itself. So I think you would have probably said in 1999, an intelligent person looking at the internet that the search engine phenomenon had played out. In fact, there were half a dozen search engine companies that were teetering on bankruptcy. It just, it just felt over. It felt like it was a feature of a bigger phenomenon of And of course, that was the year that Google got funded, and the rest of the industry, I think, recognized that we oftentimes, again, when we have greatest certainty about where the future will go, we tend to do the most damage in both understanding the current phenomenon most clearly, but also just the subtleties of a great entrepreneur who has a point of view and some meaningfully differentiated experience they're bringing to the world. So we resist defining the end, and I think Elad's comment was that I believe, and I share this point of view, that one of the major oxygen supplies For consumers, especially, is free and open distribution, and I think we could say pretty emphatically that that has evaporated in th…

AI assessment note: “So we resist defining the end, and I think Elad's comment was”

Q You said there about realizing full market potential. I do have to ask, and one of your investments being Snapchat, when the full market potential is so undefined, ephemeral messaging at the time of Snapchat's inception was, was barely even a market. So how do you view market creation with regards to this, uh, investment process and trying to assess the value of the market pre-investment?

A It centers almost entirely, at least in my case, on the quality of the entrepreneur. If an entrepreneur has a perspective, in the case of Evan at Snapchat, that there's something missing in the world that, that he wants to manifest and do it in a way where there's an authentic, unique point of view around what that is, and then something very deep, which is a, uh, hard to describe, but you Feel it, which is a sense of purpose to go do that. Then you have a hard time bounding and setting up a frame to say, okay, this is what it will be worth. I'm always amused by people who say invest in big markets because, you know, in many ways, by definition, the startup companies that do the best invest and get going in very narrow, almost ill-defined, if not completely invisible markets, you know, what was snap really doing with disappearing photos, 10 second photos for what it turned out to be, you know, late Teenage dominant female versus male. And you would have said, well, how big could that be? And I think any frame you would have applied would have missed the underlying phenomenon, which is you have a human being, a team, a company, you know, both Evan and Bobby as co-founders who had a point of view and the point of view, if you heard it, I mean, I'm telling you, if you felt it and heard it from Evan, 2000, well, gives you goosebumps. And specifically what I heard was we had lost, m…

AI assessment note: “It centers almost entirely, at least in my case, on the quality of the entrepreneur.”

Q are incredibly meaningful for any founding team, for any board, How do you think about caveating the weight of your words so that people don't simply act on them? Because as you said, you know, it's not always going to be right. It's just input. So how do you think about caveating the weight of your words to prevent that being the right way to do it for the founder?

A I think it starts with a bit of a oath that you'd take where what is your responsibility on the board in terms of impacting the outcome of the business and the quality of the business, the rigor and the probability of success. If you think your role is to provide the answers, then I think you probably shouldn't be in the boardroom. And there are times when you feel that way. When you see something with such clarity, this is the wrong VP of sales. This is the wrong pricing structure. And when you feel those instincts to give the answer, you're dishonoring the relationship. And I think that those moments require you to pull back and say, if I trust the entrepreneur and their critical thinking skills, are they asking the questions, the appropriate questions to get to the right answer? And so if you do take a step back from answer giving to question asking, And you have faith in the entrepreneur, they'll get there. That takes longer at times, because it may be easy just to say, hey, this is the wrong leader for this role, but instead say, what are the expectations of this role? And if you made those explicit, and what confidence do you have that they're going to be achieved? And so much of what you end up doing in that case is unlocking the capabilities of the organization, as opposed to scripting it. And I think most directors failed this. I have failed at this multiple times, and…

AI assessment note: “take a step back from answer giving to question asking”

Q world bluntly looks at you in a form of deity, given all the success Success and the incredible achievements you've had. I'm very much leaning and we spoke about vulnerability earlier. When you think about your own self vulnerability and attitude towards it, what are you vulnerable around yourself? I'm just intrigued given kind of the deity around your brand and providing a bit of humanity to that as well.

A Well, I remember something that someone of my thing, might think the world of Mike Moritz said, which is the minute you figured this big business out, you're done. I don't think I have superficial humility. I really genuinely Believe that this is a craft that gets practiced every day. The minute you think that you figured it out and that you've mastered it, you've shut down your capacity to do it effectively. So I have a deep and genuine sense of, I am no better than, I assure you, I'm not than anyone else practicing this business on any given day. It just depends how I show up in my capabilities and capacities mapped to the problem in front of me and the opportunity in front of me. So that vulnerability means that I'm able to say with high confidence that I make numerous mistakes in any given workday on the perspectives that I have, and I think by being receptive to where I'm getting it wrong, in a sense, it's recursive. It allows, I think, me to model behavior for the people I work with to say that is not only ok, it's part of growth, is that you're in that continual, how could I do better? What might I be missing here? And when you're asking those questions, you then raise the bar on your own internal sense of getting better and what that looks like, but also for the people you work with. Yes, at times we may seek security, but I think there's deep wisdom and insecurity in a…

AI assessment note: “I make numerous mistakes in any given workday on the perspectives that I have”

Q I've obviously from stalking many hours of your interviews, I, I've realized that a lot of your mentality is focused around How could this go right, as you often say? So I'm intrigued, uh, as a, as a new investor with that mentality, how could this go right? How do you look to balance that wonderful optimism with an element of, of caution and critical analysis? Is there a balance?

A Yeah, I think, you know, we go into any investment falling in love and love with the team, the opportunity, the potential. And it's, it's essential that when we are partnering with an entrepreneur, that they feel that belief system, that, that we have the sort of wild optimism that they have on their best Because it's a really important dimension to success is that you have to have unconditional belief in the potential and also set a very high bar around what execution towards that potential requires. So when I look at an investment like Xenly and we go into an investment, any new investment, we of course have risks in our mind around things that, that could go wrong, but we don't obsess on them in a way that it's like staring at the guardrail when you're driving, you're going to hit it. If you don't look down the road and think about what could go right. So a bulk of what we try and do at the early or Stages of a company is to not give product strategy, because I think that's something that's really best done by the product authors, but to ensure that the questions are being asked, you know, what is it that we're trying to achieve and what job are we trying to do for our consumers? And if you have clarity on those questions, then the purpose of the company, the direction, the priorities, you know, manifest in everything the company does. In that first phase, what could go wron…

AI assessment note: “we of course have risks in our mind around things that, that could go wrong”

Q I've obviously from stalking many hours of your interviews, I, I've realized that a lot of your mentality is focused around How could this go right, as you often say? So I'm intrigued, uh, as a, as a new investor with that mentality, how could this go right? How do you look to balance that wonderful optimism with an element of, of caution and critical analysis? Is there a balance?

A Yeah, I think, you know, we go into any investment falling in love and love with the team, the opportunity, the potential. And it's, it's essential that when we are partnering with an entrepreneur, that they feel that belief system, that, that we have the sort of wild optimism that they have on their best Because it's a really important dimension to success is that you have to have unconditional belief in the potential and also set a very high bar around what execution towards that potential requires. So when I look at an investment like Xenly and we go into an investment, any new investment, we of course have risks in our mind around things that, that could go wrong, but we don't obsess on them in a way that it's like staring at the guardrail when you're driving, you're going to hit it. If you don't look down the road and think about what could go right. So a bulk of what we try and do at the early or Stages of a company is to not give product strategy, because I think that's something that's really best done by the product authors, but to ensure that the questions are being asked, you know, what is it that we're trying to achieve and what job are we trying to do for our consumers? And if you have clarity on those questions, then the purpose of the company, the direction, the priorities, you know, manifest in everything the company does. In that first phase, what could go wron…

AI assessment note: “we of course have risks in our mind... but we don't obsess on them”

Q an article by Elad Gill on the end of cycles. And he stated that we're entering a period where, where everyone's looking for the next truly deep vein to explore. However, your recent investment in Zenly suggests you think there's potential runway in maybe the social vein that is somewhat considered the predecessor. I'm intrigued. How do you view the potential end of this tech cycle that we're currently in?

A You know, it's an interesting lens as you look at our investments as they cluster around trends or sectors. Or phenomenon. I think we end up putting a little bit more structure on the phenomenon than reality merits, meaning I think it's hard to say that any one of these companies is an instantiation of a trend and not something unique in and of itself. So I think you would have probably said in 1999, an intelligent person looking at the internet that the search engine phenomenon had played out. In fact, there were half a dozen search engine companies that were teetering on bankruptcy. It just, it just felt over. It felt like it was a feature of a bigger phenomenon of And of course, that was the year that Google got funded, and the rest of the industry, I think, recognized that we oftentimes, again, when we have greatest certainty about where the future will go, we tend to do the most damage in both understanding the current phenomenon most clearly, but also just the subtleties of a great entrepreneur who has a point of view and some meaningfully differentiated experience they're bringing to the world. So we resist defining the end, and I think Elad's comment was that I believe, and I share this point of view, that one of the major oxygen supplies For consumers, especially, is free and open distribution, and I think we could say pretty emphatically that that has evaporated in th…

AI assessment note: “we resist defining the end”

Q Can I ask, when you talk about the kind of the kinetic energy there, when you think about that transition in terms of the product experience, is that a gradual transition or is that actually quite a sudden product update that causes a momentary shift in terms of that transition to kinetic energy?

A I think the great products are gut punch, where you just say, wow, I can't unsee that. And it goes from like the consumer experience we used to talk about pay at the pump, right? But that was the kind of feeling you had when you ordered your first Uber and certainly the feeling that I think developers have when they deployed New Relic on a Rails application. I remember the conversation with Toby and his eyes sparkled and said, this product is magical. What it allows our developers to get access to and see versus the alternatives, which are so radically deficient compared to the gut punch feeling of one of these great product inventions. So the beginning of New Relic was that visceral. It was that immediate. Now, That didn't mean it served every market. In fact, it was very narrowly constrained to the Rails market, to Ruby on Rails, and the virtual machine that it ran with. And so what then became an issue of, okay, how do you want to have that gut punch? How do you spread that to as big a population as possible over time without losing the immediacy of that product experience as you push out into Java, into Python, into PHP? And we, you know, we debated all these different directions we could go. What we didn't debate is that the gut feel, gut punch sort of product joy was Had to be primary in the experience of the developer versus the current market that they were competing in…

AI assessment note: “The beginning of New Relic was that visceral. It was that immediate.”

Q You said before that the best founders make you feel the most uneasy. Which founders made you feel the most uneasy and why?

A The best founders make me feel like Number one, I can never control them, and I never want to control them. Number two, that given an opportunity to do the insane, reckless, non-conservative versus the rational, logical, they'll prefer the insane and the reckless. And as a fiduciary, as a board member, as a person who's with them, trying to keep the whole thing going in a coherent way, manage for its risks, I think great founders have the capacity to look past those, and I love that energy. So if I were to give you a specific Name. I would actually be letting down the fact that it's the constellation of the people we work with that represent them and the teams that they inspire, I think actually amplify it to one specific thing that's reckless. I think this is the craziness of, of, um, our world is that most every great company at some point in its early to midlife is given a chance to sell. And that's the specific moment where that founder entrepreneur has to say in a way that defies logic and conservative linear thinking, what might happen, what might go right. And what Evans said, Spiegel did at Snapchat, and this is well documented, but I don't want to talk out of school, was one of those great heroic acts, and I think Twitter did the same thing when Google approached them early in their life, Facebook with Yahoo, and it's, it's such a common refrain that you see that that …

AI assessment note: “If I were to give you a specific Name. I would actually be letting down”