The Exchanges

Q note, because I had Avicel Gog on the show, and he said, though, that despite the power of remote, Silicon Valley would still retain this kind of power and dominance that it has because of the tribal knowledge that's inherent within so many of the operators that have seen true scale. Do you think that's true in terms of that tribal knowledge, or do you think actually we're overthinking it?

A The number of experienced and talented people across multiple functions that you'll find in Silicon Valley is The concentration and depth of that talent pool is certainly higher in Silicon Valley than anywhere I've seen to date. So as a result, I think, regardless of where your company starts, there is going to be talent in Silicon Valley that you can attract to your company that's really going to push your company forward. And a great example of this is Sketch, which is primarily in Europe, recently recruited Matt Langdon as a COO, who's based in Silicon Valley. And he's one of those extraordinary people that has had experience running teams in sales, Marketing, finance, and most recently he was the CFO of MuleSoft when they both went public and got acquired by Salesforce. He's a uniquely talented person across multiple functions of an enterprise software startup. And so folks like that are, I believe, only available in the Silicon Valley ecosystem. And so as a startup, it's critically important to get folks with that depth of knowledge early on. And so, so, so people like Matt Langdon are available in Silicon Valley. Those that have Depth of knowledge of software across functions that have a depth of experience and have seen it at scale and have succeeded at scale. And if you want to attract managers and executives of that caliber, the depth of that talent pool exists in Sili…

AI assessment note: “The concentration and depth of that talent pool is certainly higher in Silicon Valley”

Q note, because I had Avicel Gog on the show, and he said, though, that despite the power of remote, Silicon Valley would still retain this kind of power and dominance that it has because of the tribal knowledge that's inherent within so many of the operators that have seen true scale. Do you think that's true in terms of that tribal knowledge, or do you think actually we're overthinking it?

A The number of experienced and talented people across multiple functions that you'll find in Silicon Valley is The concentration and depth of that talent pool is certainly higher in Silicon Valley than anywhere I've seen to date. So as a result, I think, regardless of where your company starts, there is going to be talent in Silicon Valley that you can attract to your company that's really going to push your company forward. And a great example of this is Sketch, which is primarily in Europe, recently recruited Matt Langdon as a COO, who's based in Silicon Valley. And he's one of those extraordinary people that has had experience running teams in sales, Marketing, finance, and most recently he was the CFO of MuleSoft when they both went public and got acquired by Salesforce. He's a uniquely talented person across multiple functions of an enterprise software startup. And so folks like that are, I believe, only available in the Silicon Valley ecosystem. And so as a startup, it's critically important to get folks with that depth of knowledge early on. And so, so, so people like Matt Langdon are available in Silicon Valley. Those that have Depth of knowledge of software across functions that have a depth of experience and have seen it at scale and have succeeded at scale. And if you want to attract managers and executives of that caliber, the depth of that talent pool exists in Sili…

AI assessment note: “The concentration and depth of that talent pool is certainly higher in Silicon Valley”

Q Well, that is so, so kind of you, and it means a huge amount to me coming from you, but I do want to kick off today with a little bit about you, and for those that maybe didn't hear our first round, how did you come to be a GP at one of the world's most successful funds? In the form of benchmark. What's that origin story?

A Yeah, absolutely. So I trained as an engineer at Stanford and being in the area at such a young age, you get very exposed to the ecosystem here. I just wanted to be associated with technology and associated with businesses that were doing really interesting things. And so I spent a couple of years in financial services. And then most recently I was a general partner at a It was there that I joined a company called Elastic on the board, and that was where I met my fellow benchmark partner, Peter Fenton, and we've now been on that board for a little over five years and running, and it was an incredibly remarkable experience to be on the board with Peter. I've learned so much from him, just observing how he goes about being an incredibly effective board member, and when given the chance to work with him, Bill, Eric, and Sarah on a full-time basis, I had to jump. So it's been about a year since I've joined benchmark and it's been an incredible experience.

AI assessment note: “when given the chance to work with him, Bill, Eric, and Sarah on a full-time basis, I had to jump.”

Q too intrigued on these ones not to dive into them. So if we start on one, which is market size, I've spoken to your partner, Sarah, about market size, and she says, go after markets that are small, but adjacent to very large markets. Bill said on the show, managers make the biggest mistakes when they do TAM analysis. So how do you think about an approach market sizing today?

A This is a conundrum that I think all investors face on a daily basis when they're evaluating startups. I think Bill also said on your show, one of the things to consider when evaluating a startup and the opportunity in front of them is what can go right. And that's particularly important when thinking about market sizing. And so is there a market that exists here that could shift towards this company because of this unique product? And you see that in enterprise software, especially with the advent of cloud of what used to be a fairly small market. Addressable market when everything was running on premise becoming a much larger market because it moves to the cloud. And so I think TAM analysis is the first step to that mental trap where you can look at historical or legacy markets and say, well, the last 10 years or the last 20 years, this market has been this small. And the important question to ask then is, well, is that going to be true going forward? And in some markets, the spend is actually going to go down. In some markets, the spend will probably multiply Multiply by 10 X or a hundred X. And so that's a very, very critical question to ask and not rely on these historical precedents because what was true 1520 years ago, there's certainly no guarantee that it's going to be true tomorrow.

AI assessment note: “ask then is, well, is that going to be true going forward?”

Q named Peter Fenton's quote show because I quote him so often. I do have to also, I'm biggest fan of his in terms of what I've heard from his founders about what he's like to have on their board. So you on the other side, sitting on the board with him, unfair of me to ask, but what were the biggest takeaways from seeing and sitting on boards with him?

A Yeah, number one, just how incredibly prepared he is at every single board meeting. He spends an incredible amount of time ahead of every board meeting, diving deep into the materials, having the conversations with founders and executives about questions that arise. In his mind, as he's reviewing the materials, he comes in with this mode of listening, and so he wants to hear all the things that the management teams Are going through, are thinking about, and are focused on. And because he comes in so prepared, and combined with this huge wealth of experience and knowledge that he has, everything that he talks about or focuses on in a board meeting pushes the company forward. And it's an incredible thing to watch when you have a board member that's so well-prepared, engaged, and pushing the agenda forward that each board meeting is incredibly productive, and you don't have lost time. And so you have this mode of interaction that It's hugely strategic, and you can just feel the company pushing itself forward out of those interactions, so it's been an incredibly instructive experience serving on a board with him.

AI assessment note: “number one, just how incredibly prepared he is at every single board meeting.”

Q named Peter Fenton's quote show because I quote him so often. I do have to also, I'm biggest fan of his in terms of what I've heard from his founders about what he's like to have on their board. So you on the other side, sitting on the board with him, unfair of me to ask, but what were the biggest takeaways from seeing and sitting on boards with him?

A Yeah, number one, just how incredibly prepared he is at every single board meeting. He spends an incredible amount of time ahead of every board meeting, diving deep into the materials, having the conversations with founders and executives about questions that arise. In his mind, as he's reviewing the materials, he comes in with this mode of listening, and so he wants to hear all the things that the management teams Are going through, are thinking about, and are focused on. And because he comes in so prepared, and combined with this huge wealth of experience and knowledge that he has, everything that he talks about or focuses on in a board meeting pushes the company forward. And it's an incredible thing to watch when you have a board member that's so well-prepared, engaged, and pushing the agenda forward that each board meeting is incredibly productive, and you don't have lost time. And so you have this mode of interaction that It's hugely strategic, and you can just feel the company pushing itself forward out of those interactions, so it's been an incredibly instructive experience serving on a board with him.

AI assessment note: “number one, just how incredibly prepared he is at every single board meeting.”

Q person who's using it is the one who actually submits the credit card, but often also for large enterprise contracts that we both see often. Actually, there is an element of agency with someone buying it on behalf of someone else or a department. How do you approach this agency problem? And is that a big sticking point for you today with the rise of bottoms up that we've seen?

A Yeah. So understanding who the user is and who the buyer is, is critically important. If they're two different people, you have to create engagement within the user to the point that they become your champion, such that when the buyer enters the decision-making process, the user is heavily influential on your behalf. As a champion of your product. Oftentimes if you don't understand that relationship and the user has not become a champion of the product, the buyer then has an enormous decision-making power, whether it's like a procurement process in large enterprises or whether it's a decision-making process in smaller ones. If that interaction isn't clear and you haven't sort of mapped that out, it's very difficult to convert into paying users and you'll find difficulty in renewals and difficulties in expansion. But once that interaction is clear, And you've aligned yourself with that. It can be hugely beneficial, especially if you can get users to become champions of your product.

AI assessment note: “you have to create engagement within the user to the point that they become your champion”

Q had someone on the show, David, from Expansify, and he said that too many people are not thinking about the really long term and investing for the really long term and actually building companies for quick flips in the valley today. Do you think that's a fair summary, or would you actually say that there is this incredible generation of kind of visionary thinkers building meaningful companies with long-term visions?

A You know, we talk about this quite a lot in our partner meetings. The energy and the enthusiasm we see from the entrepreneurial ecosystem, In Silicon Valley is incredible. The just big dreams that people are thinking about on a daily basis, and the idea of wanting to build companies that go for 1020 plus years, is something that I think is actually becoming more common than not. And I think that people are starting to understand that, especially in my world of software, that companies now have an opportunity with the introduction of cloud and all these new technology modes that are coming online. That it's a special moment in time to build components of the enterprise IT stack in a meaningful way that you can create really, really valuable companies that become great places to work for a long extended period of time. I would say that the energy towards long-term orientation and building really meaningful companies is extraordinarily high, and it's, it's a lot of positive energy.

AI assessment note: “the idea of wanting to build companies that go for 1020 plus years”

Q too intrigued on these ones not to dive into them. So if we start on one, which is market size, I've spoken to your partner, Sarah, about market size, and she says, go after markets that are small, but adjacent to very large markets. Bill said on the show, managers make the biggest mistakes when they do TAM analysis. So how do you think about an approach market sizing today?

A This is a conundrum that I think all investors face on a daily basis when they're evaluating startups. I think Bill also said on your show, one of the things to consider when evaluating a startup and the opportunity in front of them is what can go right. And that's particularly important when thinking about market sizing. And so is there a market that exists here that could shift towards this company because of this unique product? And you see that in enterprise software, especially with the advent of cloud of what used to be a fairly small market. Addressable market when everything was running on premise becoming a much larger market because it moves to the cloud. And so I think TAM analysis is the first step to that mental trap where you can look at historical or legacy markets and say, well, the last 10 years or the last 20 years, this market has been this small. And the important question to ask then is, well, is that going to be true going forward? And in some markets, the spend is actually going to go down. In some markets, the spend will probably multiply Multiply by 10 X or a hundred X. And so that's a very, very critical question to ask and not rely on these historical precedents because what was true 1520 years ago, there's certainly no guarantee that it's going to be true tomorrow.

AI assessment note: “the important question to ask then is, well, is that going to be true”

Q Well, that is so, so kind of you, and it means a huge amount to me coming from you, but I do want to kick off today with a little bit about you, and for those that maybe didn't hear our first round, how did you come to be a GP at one of the world's most successful funds? In the form of benchmark. What's that origin story?

A Yeah, absolutely. So I trained as an engineer at Stanford and being in the area at such a young age, you get very exposed to the ecosystem here. I just wanted to be associated with technology and associated with businesses that were doing really interesting things. And so I spent a couple of years in financial services. And then most recently I was a general partner at a It was there that I joined a company called Elastic on the board, and that was where I met my fellow benchmark partner, Peter Fenton, and we've now been on that board for a little over five years and running, and it was an incredibly remarkable experience to be on the board with Peter. I've learned so much from him, just observing how he goes about being an incredibly effective board member, and when given the chance to work with him, Bill, Eric, and Sarah on a full-time basis, I had to jump. So it's been about a year since I've joined benchmark and it's been an incredible experience.

AI assessment note: “joined a company called Elastic on the board, and that was where I met”

Q I do have to ask for some that maybe want to attribute some form of measurement to it. How do you feel about MPS? How much weight do you pay to it? And how do you think about that when assessing companies today?

A Yeah, in software and enterprise software, Where I spend the vast majority of my time, NPS and customer and whatever metric you like to use to measure customer satisfaction is critically important, especially in the early stages. An NPS service may not be the right mode of engagement with your customers. So every company has to pick the right way to get feedback from their customers about how that product is going. But that is one of the main things that you have to go about collecting data on from the early stages. Number one, why are customers interested in the product? What are the use cases that they see as addressable by your product? Number two, how are they getting value out of the product itself? How are they using it? What problems are they trying to solve? Then three, just trying to understand within the organization itself, who is using the product? And once you get those three data points across your customer base in the early days, it can be very, very instructive in terms of how folks are interpreting the product, how people are using the product, Where the value proposition really lies in the customer's mind and where you can push the product in terms of new modules or new features to further that engagement with the customers.

AI assessment note: “NPS and customer and whatever metric you like to use to measure customer satisfaction is critically important”

Q I couldn't agree more in terms of getting that internal champion. The other element that I did want to touch on was you said specifically about metrics relative to other companies. How do you advise maybe portfolio founders that they should think about and address the element of competition?

A Again, I go back to product fundamentals here. I think that in most markets, There are multiple competitors. There are going to be competitors that are from products that are from legacy brands or legacy companies. There are going to be competitors that are just starting and are perhaps a couple of years behind your startup. So the best way to go about it is really understanding the products of everybody involved in your market. And I think the optimal strategy is to assume that everybody that is competing with you has actually had or has found some unique insight as to why the market is addressable in their unique approach. And so to assume that your competitors are all really smart, that they all know what they're doing, and you go about, and you look at that strategy and say, like, why did they pick it this way? Why are they going about doing it this way? And then really picking apart and trying to understand that product strategy is particularly important, because that may reveal to you some insights about the market that you had been previously blind to. I think the optimal strategy about competition is to really, again, orient towards product, and two, assume that your competitors have found some unique insight And investigate and try to figure out what that insight they may have discovered to create a product strategy that they're going about creating.

AI assessment note: “the best way to go about it is really understanding the products of everybody”

Q You said about the places to work there, and that's a really interesting point, because it is a war for talent now in the Valley, and I, I do want to ask your kind of insider perspective How do you assess this kind of war for talent, so to speak, and see the recruiting for startups market today?

A Yes, absolutely. If you are a talented engineer, a talented product manager, a talented sales executive, talented marketer, if you're a talented employee at the moment, and you're looking at the opportunity of startups to go work for, the opportunity set is really, really large at the moment. And as more and more companies start to embrace remote working cultures, which I've been a huge fan of, And I think is a great way for startups to build from day one by being remote from day one. You have, as someone that's looking for startup opportunities, a wide range of options. For startups to effectively compete for that talent, they're going to have to really communicate their mission and why they exist as a company very, very effectively. And I think really compelling your potential new employees to join because of what you're building, why you're building it, It's critically important in a recruiting market that is becoming more and more competitive every single day. And, and it's becoming more and more competitive, not only in Silicon Valley, it's competitive everywhere. I talk to startups that are trying to recruit, you know, the West coast of the United States, the Midwest, the East coast, you know, the Rocky mountain area, look at Europe, you look at India, the talent and recruiting continues to be very, very competitive in all of these markets. And so really orienting towards…

AI assessment note: “it's becoming more and more competitive, not only in Silicon Valley, it's competitive everywhere.”

Q You said the word market there, and I do want to ask about public companies. Do you think it's fair that often today there's this assessment that in terms of whether they're good for the company itself, how do you view being public in terms of what it does for the company itself?

A Yeah, absolutely. You know, I've been really fortunate to be part of a number of journeys from startup to being a publicly traded company. And one of the things that I've noticed as a company gets close to being a public company is that the operational rigor that's implemented inside of a company just gets tighter. The timelines get more precise. The sales cycles and forecasting capability of your sales team or your marketing teams, they start becoming more precise. They tend to become more disciplined in terms of how they go about thinking about each quarter or each year. And so I think the level of discipline and rigor that's introduced By the idea that, hey, you're going to have a very large shareholder base, and every quarter you're going to have to come out and talk about publicly how you just did, and all your customers are going to know how you just did, all your investors are going to know how you just did, and how all your competitors are going to know how you just did. I think having that light and that spotlight on your company just makes the execution orientation of everybody go to another level, and I think it's just a really, really positive force in In the growth of a company, especially in software, and so I think it's just an incredibly important step for companies to go through, and it's an incredible maturation step for companies in their life cycle, and just…

AI assessment note: “the operational rigor that's implemented inside of a company just gets tighter”

Q You said the word market there, and I do want to ask about public companies. Do you think it's fair that often today there's this assessment that in terms of whether they're good for the company itself, how do you view being public in terms of what it does for the company itself?

A Yeah, absolutely. You know, I've been really fortunate to be part of a number of journeys from startup to being a publicly traded company. And one of the things that I've noticed as a company gets close to being a public company is that the operational rigor that's implemented inside of a company just gets tighter. The timelines get more precise. The sales cycles and forecasting capability of your sales team or your marketing teams, they start becoming more precise. They tend to become more disciplined in terms of how they go about thinking about each quarter or each year. And so I think the level of discipline and rigor that's introduced By the idea that, hey, you're going to have a very large shareholder base, and every quarter you're going to have to come out and talk about publicly how you just did, and all your customers are going to know how you just did, all your investors are going to know how you just did, and how all your competitors are going to know how you just did. I think having that light and that spotlight on your company just makes the execution orientation of everybody go to another level, and I think it's just a really, really positive force in In the growth of a company, especially in software, and so I think it's just an incredibly important step for companies to go through, and it's an incredible maturation step for companies in their life cycle, and just…

AI assessment note: “it's just a really, really positive force in In the growth of a company”

Q You said about the places to work there, and that's a really interesting point, because it is a war for talent now in the Valley, and I, I do want to ask your kind of insider perspective How do you assess this kind of war for talent, so to speak, and see the recruiting for startups market today?

A Yes, absolutely. If you are a talented engineer, a talented product manager, a talented sales executive, talented marketer, if you're a talented employee at the moment, and you're looking at the opportunity of startups to go work for, the opportunity set is really, really large at the moment. And as more and more companies start to embrace remote working cultures, which I've been a huge fan of, And I think is a great way for startups to build from day one by being remote from day one. You have, as someone that's looking for startup opportunities, a wide range of options. For startups to effectively compete for that talent, they're going to have to really communicate their mission and why they exist as a company very, very effectively. And I think really compelling your potential new employees to join because of what you're building, why you're building it, It's critically important in a recruiting market that is becoming more and more competitive every single day. And, and it's becoming more and more competitive, not only in Silicon Valley, it's competitive everywhere. I talk to startups that are trying to recruit, you know, the West coast of the United States, the Midwest, the East coast, you know, the Rocky mountain area, look at Europe, you look at India, the talent and recruiting continues to be very, very competitive in all of these markets. And so really orienting towards…

AI assessment note: “the opportunity set is really, really large at the moment.”

Q your time among the portfolio there. In terms of where you're spending your time, Chathan, you're spending a lot of time in Europe, and I would love to say it's just because of my charm and charisma, but two deals in 12 months for Benchmark. So I'd love to hear, what's the thinking around Europe and the more recent move to Europe for you as a Benchmark kind of strategy?

A As benchmark as a fund, if you look at the historical track record of benchmark, we've always been quite opportunistic in Europe in terms of opportunities, and so there have been great startups that have started in Europe throughout benchmarks investment history that have then expanded pretty aggressively to Silicon Valley. So I think as a firm, we're open to great ideas and innovation regardless of where it comes from. I think that The two sales in 12 months was a, was a great coincidence, and things just happened to work out that way. I think Europe has a great deal of innovation happening right now, and it's an exciting time for startups in Europe, for sure, but we continue to think about all regions, both across the United States, Europe, whatever it may be, that innovation is going to come out of the hands of great entrepreneurs, and you just have to be open and receptive to those ideas, and We can certainly be very, very helpful as those companies scale and become large, meaningful companies.

AI assessment note: “The two sales in 12 months was a, was a great coincidence”

Q the hardest round, but it's on time allocation, the biggest challenge of venture, I think. So how do you think about how you spend your time across the existing portfolio? Because some have the thesis of spend time with the winners, it's those that return the funds, and then others say spend time with the strugglers, it's there where you build your reputation. How do you think about time allocation?

A I think that you have to sign up for the whole journey of the company, and what might look like something that's struggling at the moment could very quickly turn around and be something that's blossoming in a few quarters time. And what seems to be going really well could at the same time turn on you, and they could go through their own struggles. In a few quarters time as well. And so as a board member, you have a, I think an obligation to be there for your entrepreneurs through both the good times and the rough and really try to see through that journey. And I personally think that your reputation is made by both how you behave and how supportive you are as a board member in both the good times and the times when things feel like they're going sideways. And so I think in terms of time allocation, you have to exert a great deal of effort Against every opportunity and every partnership that you're working on, and to make them as successful as possible. And sometimes it doesn't work out, and that's just fine, and sometimes it works incredibly well.

AI assessment note: “exert a great deal of effort Against every opportunity and every partnership”

Q I do have to ask for some that maybe want to attribute some form of measurement to it. How do you feel about MPS? How much weight do you pay to it? And how do you think about that when assessing companies today?

A Yeah, in software and enterprise software, Where I spend the vast majority of my time, NPS and customer and whatever metric you like to use to measure customer satisfaction is critically important, especially in the early stages. An NPS service may not be the right mode of engagement with your customers. So every company has to pick the right way to get feedback from their customers about how that product is going. But that is one of the main things that you have to go about collecting data on from the early stages. Number one, why are customers interested in the product? What are the use cases that they see as addressable by your product? Number two, how are they getting value out of the product itself? How are they using it? What problems are they trying to solve? Then three, just trying to understand within the organization itself, who is using the product? And once you get those three data points across your customer base in the early days, it can be very, very instructive in terms of how folks are interpreting the product, how people are using the product, Where the value proposition really lies in the customer's mind and where you can push the product in terms of new modules or new features to further that engagement with the customers.

AI assessment note: “NPS and customer and whatever metric you like to use to measure customer satisfaction is critically important”

Q person who's using it is the one who actually submits the credit card, but often also for large enterprise contracts that we both see often. Actually, there is an element of agency with someone buying it on behalf of someone else or a department. How do you approach this agency problem? And is that a big sticking point for you today with the rise of bottoms up that we've seen?

A Yeah. So understanding who the user is and who the buyer is, is critically important. If they're two different people, you have to create engagement within the user to the point that they become your champion, such that when the buyer enters the decision-making process, the user is heavily influential on your behalf. As a champion of your product. Oftentimes if you don't understand that relationship and the user has not become a champion of the product, the buyer then has an enormous decision-making power, whether it's like a procurement process in large enterprises or whether it's a decision-making process in smaller ones. If that interaction isn't clear and you haven't sort of mapped that out, it's very difficult to convert into paying users and you'll find difficulty in renewals and difficulties in expansion. But once that interaction is clear, And you've aligned yourself with that. It can be hugely beneficial, especially if you can get users to become champions of your product.

AI assessment note: “you have to create engagement within the user to the point that they become your champion”

Q Totally with you. Can I ask for remote teams? The big question I always ask, should they be Paid in accordance to local salary benchmarks, or should it be uniform across the country?

A I think that as companies become remote, and as top talented, whether it be developers, or salespeople, or marketing people, have access to remote companies, it's really hard to do a cost arbitrage these days. I think most people know pretty quickly sort of the going rate for their talent, and so trying to hire remote people primarily, or remote folks Primarily because of a cost arbitrage. I think it's sort of like quicksand type approach. And so I think you really have to just go for the best possible talent that you can attract. You have to then assume that there's going to be pretty perfect information in terms of clearing talent in that market. And so you have to pay and think about compensation in a way that's generous and attractive and will make sure that the person you're hiring feels like they're compensated well.

AI assessment note: “trying to hire remote folks Primarily because of a cost arbitrage... is sort of like quicksand”

Q Totally with you. Can I ask for remote teams? The big question I always ask, should they be Paid in accordance to local salary benchmarks, or should it be uniform across the country?

A I think that as companies become remote, and as top talented, whether it be developers, or salespeople, or marketing people, have access to remote companies, it's really hard to do a cost arbitrage these days. I think most people know pretty quickly sort of the going rate for their talent, and so trying to hire remote people primarily, or remote folks Primarily because of a cost arbitrage. I think it's sort of like quicksand type approach. And so I think you really have to just go for the best possible talent that you can attract. You have to then assume that there's going to be pretty perfect information in terms of clearing talent in that market. And so you have to pay and think about compensation in a way that's generous and attractive and will make sure that the person you're hiring feels like they're compensated well.

AI assessment note: “it's really hard to do a cost arbitrage these days.”

Q I couldn't agree more in terms of getting that internal champion. The other element that I did want to touch on was you said specifically about metrics relative to other companies. How do you advise maybe portfolio founders that they should think about and address the element of competition?

A Again, I go back to product fundamentals here. I think that in most markets, There are multiple competitors. There are going to be competitors that are from products that are from legacy brands or legacy companies. There are going to be competitors that are just starting and are perhaps a couple of years behind your startup. So the best way to go about it is really understanding the products of everybody involved in your market. And I think the optimal strategy is to assume that everybody that is competing with you has actually had or has found some unique insight as to why the market is addressable in their unique approach. And so to assume that your competitors are all really smart, that they all know what they're doing, and you go about, and you look at that strategy and say, like, why did they pick it this way? Why are they going about doing it this way? And then really picking apart and trying to understand that product strategy is particularly important, because that may reveal to you some insights about the market that you had been previously blind to. I think the optimal strategy about competition is to really, again, orient towards product, and two, assume that your competitors have found some unique insight And investigate and try to figure out what that insight they may have discovered to create a product strategy that they're going about creating.

AI assessment note: “assume that everybody that is competing with you has actually had or has found some unique insight”

Q You've been a partner across two of the biggest and best firms in venture. What do you know now that you wish you'd known at the start of your career in venture, Chatham?

A I think that one of the things that become more obvious becomes more obvious as you Spend more time in venture is that opportunities just come out of nowhere and that it's really surprising where the next opportunity that gets really exciting comes from. And it's, and just being very, very open to ideas and being very, very open to entrepreneurs that, that come up with really exciting problems to solve is one that I think is hard to know before entering the industry is I think it's been very, very surprising to me as I've learned and it continues to be An exciting part of my job every day is just the unexpected element of what you're going to see today.

AI assessment note: “opportunities just come out of nowhere and that it's really surprising”