The Exchanges

Q Sure. Absolutely. And so would you say you don't agree with the recent view that kind of failure is a necessity for entrepreneurs to be successful and that it's so important to Would you say you agree, you disagree with that view?

A I think it's very confusing. There's, there's definitely a correlation causality problem in the discussion, and there's a, I would say there's a, the trendiness problem in the discussion, which is the, you know, the idea of, you know, failure is a badge of honor, or as human beings, we love the, uh, you know, we love the stories of redemption, uh, somebody's successful, then they fail, then they succeed again. Like, those are natural human things that we're attracted to. Um, I, I prefer to think of Uh, failure as a, uh, continuous thing that happens all throughout one's life on all vectors, and it's not that we're focused on that moment in time where the company fails, but every success I've ever been in, uh, involved in has had multiple points of failure, some of them near-death experiences for the company, and the great founders and the great companies Uh, and I think the great investors are the ones that have a lot of durability, uh, through those moments in time, especially if you're playing a long-term game, which is to say that you might have a company that fails, but if you do it in a way that's respectful, uh, of everybody, it's likely that a number of those people will, uh, be there for you the next time because you've learned a lot from the failure. If you're not respectful and grace, graceful in that context, uh, you know, that's, uh, that's going to come back to hau…

AI assessment note: “I prefer to think of Uh, failure as a, uh, continuous thing”

Q team and being open with them, a lot of what would prevent me talking about depression, bulimia before, Honestly, it's actually LP reactions. How would LPs feel? And on the founder side, I guess it's how would my VCs feel? How would my board members feel? How do you guys think about that fear of transparency with these stakeholders who fund a lot of what we do in many respects?

A Well, let's start from the premise that every single human being on the planet is flawed, and we're all flawed in different ways. We're all imperfect. And this idealized state that our culture Has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful. And on top of it, and I think Jerry said it really well, all of those pressures create endless negative feedback loops, which just makes it harder to be successful or effective or whatever adjective you want to fill in the blank with. As part of it, this notion that you have to present yourself a certain way, because everybody else is presenting themselves a certain way, then creates this recurring feedback loop of loneliness, of isolation. It actually goes the other direction, where you become more and more disconnected from everybody else, because you know your sort of true sense, but you're pretending or you're behaving in a way to try to look like everybody else, who are also Pretending in a certain way because they're not being their true selves and on and on it goes. That doesn't mean that there is a way to be. I think that from my frame of reference, everybody should be however they want to be. And the challenge is this notion that there is a certain way to be. Rather than to allow yourself to blossom and to evolve the way you …

AI assessment note: “from my perspective as an investor, I think entrepreneurs who I encounter and work with”

Q Can I ask, in that scale from product to company, where do you see commonalities maybe in where people make mistakes? Be it not surrounding themselves with that experience C-suite, whatever that may be, where do you see the commonalities in terms of the product company transition?

A It's all over the place, and part of it's because I've made myself so many different categories and types of mistakes. I think a really good investor and really good entrepreneurs recognize that the path to success is a combination of endless experiments where there's two branches. There's a success or there's failure on the individual experiment. If you fail, you learn what you can from the experiment. And then go run the next experiment. If you succeed with the experiment, you do more of that. And when I think about all the different categories of experiments that I've been involved in, whether I've been the one running them or somebody else in the founders of a company or the CEO of a company has been running them and failed. If I look at a successful company, you know, there's hundreds or thousands of these experiments along the way. I look across all the different companies I've been involved in. There's not a category that you say, well, this one happens over and over again. There are lots of different categories of mistakes that happen over and over again, and I have an internal joke that I say to myself, and Amy, my wife hears me say it when I'm frustrated with myself around making a mistake, which is, man, I'm not going to make that mistake a fourth time. This whole idea that, okay, I made a mistake and I learned from it. I never make it again. And like, you know, 20 y…

AI assessment note: “There's not a category that you say, well, this one happens over and over again.”

Q Can I ask, in that scale from product to company, where do you see commonalities maybe in where people make mistakes? Be it not surrounding themselves with that experience C-suite, whatever that may be, where do you see the commonalities in terms of the product company transition?

A It's all over the place, and part of it's because I've made myself so many different categories and types of mistakes. I think a really good investor and really good entrepreneurs recognize that the path to success is a combination of endless experiments where there's two branches. There's a success or there's failure on the individual experiment. If you fail, you learn what you can from the experiment. And then go run the next experiment. If you succeed with the experiment, you do more of that. And when I think about all the different categories of experiments that I've been involved in, whether I've been the one running them or somebody else in the founders of a company or the CEO of a company has been running them and failed. If I look at a successful company, you know, there's hundreds or thousands of these experiments along the way. I look across all the different companies I've been involved in. There's not a category that you say, well, this one happens over and over again. There are lots of different categories of mistakes that happen over and over again, and I have an internal joke that I say to myself, and Amy, my wife hears me say it when I'm frustrated with myself around making a mistake, which is, man, I'm not going to make that mistake a fourth time. This whole idea that, okay, I made a mistake and I learned from it. I never make it again. And like, you know, 20 y…

AI assessment note: “There's not a category that you say, well, this one happens over and over”

Q one element there. You said obviously about the primary element of the founder, but then also the product. I'm also today much more enamored and intrigued by the market from a meta perspective, always concerned that products change so rapidly, iterations, and actually the product you invest in today isn't what it is tomorrow. How do you think about product versus market? And that thought process when evaluating opportunities today.

A So most of the companies that I've invested in over the years that have been really successful at the point of the initial investment, the market opportunity, you'd look at it and you'd either say it was zero or infinite. And it was one of these things where the venture cliche of total available market, especially at the early stages is really not that helpful, especially when you're coming into a world with a product obsession, even if you're to Displacing an existing incumbent product. The interesting trajectory of that is that early in the life of a company, the product does matter a ton. As the company starts to grow and develop, the great founding CEOs start to view the company itself as the product. So they evolved from being product focused, and the thing that they're really working on all the time is that initial product, to being company focused, where what they're working on is the growth and development of the company. You actually see this in some companies that look like they're scaling really well and then fall apart for various reasons is that the founding CEOs often get distracted and stop putting the energy into really working on the company. And really charismatic founders can often get a lot of money raised before you really understand that there's cracks in the foundation because there isn't that scaling from product to company.

AI assessment note: “total available market, especially at the early stages is really not that helpful”

Q team and being open with them, a lot of what would prevent me talking about depression, bulimia before, Honestly, it's actually LP reactions. How would LPs feel? And on the founder side, I guess it's how would my VCs feel? How would my board members feel? How do you guys think about that fear of transparency with these stakeholders who fund a lot of what we do in many respects?

A Well, let's start from the premise that every single human being on the planet is flawed, and we're all flawed in different ways. We're all imperfect. And this idealized state that our culture Has created where you have to carry yourself and present yourself in a certain way is actually a massive inhibitor of people being effective and successful. And on top of it, and I think Jerry said it really well, all of those pressures create endless negative feedback loops, which just makes it harder to be successful or effective or whatever adjective you want to fill in the blank with. As part of it, this notion that you have to present yourself a certain way, because everybody else is presenting themselves a certain way, then creates this recurring feedback loop of loneliness, of isolation. It actually goes the other direction, where you become more and more disconnected from everybody else, because you know your sort of true sense, but you're pretending or you're behaving in a way to try to look like everybody else, who are also Pretending in a certain way because they're not being their true selves and on and on it goes. That doesn't mean that there is a way to be. I think that from my frame of reference, everybody should be however they want to be. And the challenge is this notion that there is a certain way to be. Rather than to allow yourself to blossom and to evolve the way you …

AI assessment note: “from my perspective as an investor, I think entrepreneurs who I encounter and work with”