The Exchanges

Q the schedule, so like, ah, fuck it, I'll just ask them anyway. So Shishir told me that there were some incredible war stories from the multiple different amazing companies that you worked at, from Microsoft to SAP to Dropbox. When you think about, like, your favorite war story, I'm just too intrigued. What's the one that stands out the most to you in terms of the war story you remember?

A Well, I mean, look, Microsoft was a master class in everything. Building products, building strategy, building a business, building organizations, leading, managing, There's a lot of stuff that stands out to me. Probably the stories that people find the most entertaining are the ones that involve Bill. Bill Gates famously had a little bit of drive and impatience, let's call it. And it was a rite of passage to be in a conference room with Bill and in a debate with him and win a point. Like, just to win a debate, right, was this major rite of passage. And he usually had a couple of different interesting quips to kind of come back, even when he was acquiescing. My favorite moment on that was I was working on this project called WinFS, and I was debating with him about this ontology model. That we were working on, and very complex topic. This is actually a debate that took more than one meeting, and I'm in this meeting, and I think I finally have him. I could see it on his face, like, oh, yeah, maybe they're right. And he pauses, he sits back, and he looks at me, he says, okay, great, but who's the smart person you're going to hire to go get it done? And so it's like, okay, he was willing to admit that I kind of won this point over, but also kind of remind me that it shouldn't have taken me so long to get there with him.

AI assessment note: “My favorite moment on that was I was working on this project called WinFS”

Q Oh, you are far too kind and too charming, but I do want to kick off with a little bit on you. So tell me, how did you make your way into the world of venture, and how did you come to be an MD at GC today?

A Yeah, it's a good question, and I think it's an important question relative to how I got to General Catalyst as well in specific. But I'm a longtime operator, right? I was 20 plus years building software, building businesses, building teams, etc. And I was at Microsoft, and Microsoft before Satya was a little insular. Like, we're up there in the woods in Seattle, and we didn't really kind of get down to the valley very much, right? When I moved here in 2014, friends that I knew, people that had moved down here said, you really should meet some venture capitalists. Like, you should understand that part of the world. I'd just become the CTO of SAP, and I'm like, that makes sense. And I had friends set up meetings. Meetings number one, and number two, Reid Hoffman, Hemantinajah. I kid you not, I sit down for breakfast with Reed, and I'm like, so Reed, what is it you do? And he looks at me, he's like, you are new here, aren't you? And, you know, I started chuckled, right? But SAP was a great job, because everyone took the call from the CTO of SAP, right? And I was able to network, and I was able to learn. And when I left SAP, I was able to spend a lot of time with people, and a lot of time on things I was interested in, right? So I was able to kind of operate like an investor might. Spent time with the tier one VCs, including, of course, General Catalyst, looked at deals, went to M…

AI assessment note: “at some point I started to realize that I think I want to do this professionally”

Q I'm not even the one who sends like, you know, ridiculous messages at three in the morning with new projects that we need to do, and then like, just expect this kind of trail of destruction to be left behind me, and I'm a shit manager. What's the difference in your mind between leadership and management, and how should I think about that, and how should we think about that?

A Yeah, I think it's pretty simple. Leadership is about followership. Leadership is really about if there comes a moment when a group of people need to head in some direction, Do you have the followership to lead those people, to literally guide those people in that direction, push in that direction? Management is about all the stuff that it takes to have a functioning, cohesive system of people. And ultimately, so the very best people that I've worked with over the years, that includes Gates, it includes McDermott, it includes Satya, it includes so many people, are both great leaders and great managers. And yeah, they spike a little bit one or the other, but saying that direction, getting the followership versus just setting up a system. That is capable of doing great work is also a different discipline, different art.

AI assessment note: “Leadership is about followership. Management is about all the stuff that it takes”

Q You said there about kind of learning new skills, though, in terms of kind of the leadership and the management. You know, obviously now on the other side of the table with GC, you know, Why did you choose GC? What was the thinking and rationale behind that? Let's start there on the investing side.

A I am very fortunate. I had options, and General Catalyst felt really right. I mean, part of it's a little bit unfair. I had been working with them, 2016, 2017, spent a lot of time with them. Himatha and I hashed a company together in the healthcare space. Steve Herod and I worked on a deal together, so I knew that team pretty well, but like I say, I had options, and my calculation was basically the following. I was looking for a firm on the rise, and if you look at General Catalyst's book, Livongo, Stripe, BeCommerce, Simcera, Gusto, Oscar, Lemonade, Underworld, Applied Intuition, Canva, Grammarly. I mean, do I have to go on? Like, it is clear it is a firm that in the last several years, let's call it like between now and the past five years or so, has really come into its own in terms of making great, great investments, great bets. And it has real leaders in the industry, right? Joel Cutler, David Fialco, these amazingly humble, high-value human beings that founded, of course, General Catalyst. Hemantanaja, one of the very best now in the game, really coming into a zone. And I knew them well. And the final thing really was about culture and what they stand for. And This notion of responsible innovation really wanted to be partners to their founders, and so builders, that was important to me as an ex-operator. So GC just felt very much right.

AI assessment note: “my calculation was basically the following. I was looking for a firm on the rise”

Q How do you think through that? Because I'm seeing this with a lot of companies today where it's like, absolutely, kind of, blatant consumer demand is through the roof, and I'm essentially analyzing sustainability of consumer demand, and whether it's like a pivotal seismic change into Societal behavior, or actually a transient moment of how we act versus the sustainable ongoing. How do you think through that?

A I think that one of the things you can look at is there evidence of something working before the pandemic hit to distinguish between are we looking at acceleration because of the forced onboarding, or are we looking at something that has been created just during this environment? So I'll give you an example. In the healthcare industry, one of the things we've observed is that telemedicine has been taken off like crazy. Right. And you may know that we're the largest shareholders in Livongo. Livongo is merging now with Teladoc, and there's like a whole thesis behind that. And you could say, okay, is that just a pandemic thing? Or is it actually more of an acceleration of something that already was coming into its own? And we really believe in the latter. After we've now taught everybody that to go to the doctor, what you do is you get out your phone and the app, or you go to a website, you log in with your provider, and you telemedicine somebody in a couple of hours. And if you really need to be hands-on, With somebody, then they'll bring you in and get you an appointment, etc. After we've been on board in that experience, nobody's going to go back to the old way. Like the old way of, I pick up the phone. I punch a lot of buttons to go through a call tree. I finally end up with a human being. They send me up on a schedule four weeks from now. I drive to the place. I sit in the lo…

AI assessment note: “is there evidence of something working before the pandemic hit to distinguish between”

Q the schedule, so like, ah, fuck it, I'll just ask them anyway. So Shishir told me that there were some incredible war stories from the multiple different amazing companies that you worked at, from Microsoft to SAP to Dropbox. When you think about, like, your favorite war story, I'm just too intrigued. What's the one that stands out the most to you in terms of the war story you remember?

A Well, I mean, look, Microsoft was a master class in everything. Building products, building strategy, building a business, building organizations, leading, managing, There's a lot of stuff that stands out to me. Probably the stories that people find the most entertaining are the ones that involve Bill. Bill Gates famously had a little bit of drive and impatience, let's call it. And it was a rite of passage to be in a conference room with Bill and in a debate with him and win a point. Like, just to win a debate, right, was this major rite of passage. And he usually had a couple of different interesting quips to kind of come back, even when he was acquiescing. My favorite moment on that was I was working on this project called WinFS, and I was debating with him about this ontology model. That we were working on, and very complex topic. This is actually a debate that took more than one meeting, and I'm in this meeting, and I think I finally have him. I could see it on his face, like, oh, yeah, maybe they're right. And he pauses, he sits back, and he looks at me, he says, okay, great, but who's the smart person you're going to hire to go get it done? And so it's like, okay, he was willing to admit that I kind of won this point over, but also kind of remind me that it shouldn't have taken me so long to get there with him.

AI assessment note: “My favorite moment on that was I was working on this project called WinFS”

Q You said there about kind of learning new skills, though, in terms of kind of the leadership and the management. You know, obviously now on the other side of the table with GC, you know, Why did you choose GC? What was the thinking and rationale behind that? Let's start there on the investing side.

A I am very fortunate. I had options, and General Catalyst felt really right. I mean, part of it's a little bit unfair. I had been working with them, 2016, 2017, spent a lot of time with them. Himatha and I hashed a company together in the healthcare space. Steve Herod and I worked on a deal together, so I knew that team pretty well, but like I say, I had options, and my calculation was basically the following. I was looking for a firm on the rise, and if you look at General Catalyst's book, Livongo, Stripe, BeCommerce, Simcera, Gusto, Oscar, Lemonade, Underworld, Applied Intuition, Canva, Grammarly. I mean, do I have to go on? Like, it is clear it is a firm that in the last several years, let's call it like between now and the past five years or so, has really come into its own in terms of making great, great investments, great bets. And it has real leaders in the industry, right? Joel Cutler, David Fialco, these amazingly humble, high-value human beings that founded, of course, General Catalyst. Hemantanaja, one of the very best now in the game, really coming into a zone. And I knew them well. And the final thing really was about culture and what they stand for. And This notion of responsible innovation really wanted to be partners to their founders, and so builders, that was important to me as an ex-operator. So GC just felt very much right.

AI assessment note: “my calculation was basically the following. I was looking for a firm on the rise”

Q Can I ask, you know, when you have, like, very young founders in particular, maybe first-time founders, or just younger founders, you have such weight of experience that when you pose your questions, Even if they're posed as questions, the weight of your words are pretty heavy. Do you have to think through that and be very kind of cautious and deliberate in the weight of your own words?

A Yeah, it's funny, like, as an operator, many senior operators will tell you that they all had this similar experience, which is, you're in a meeting with a team, you make an offhand comment, you come back with this team, like, a month later, and you find out that they've been busy, like, off doing some crazy thing because of this comment you made. Cause they took it as direction, right? They took it as gospel. And so at some point in your career as an operator, as you go through this, you kind of learn, oh, I've got to be cautious about being clear when I'm actually giving strong guidance or I'm making a decision versus when I'm just showing curiosity. And one of the things I got very used to as an operating leader and that I'm accustomed to as a board member is posing these questions and being really clear. Like I am just curious. I don't know if this is the right thing to do or not, but I'm curious about the following thing. And let them take that ownership from that point and sort out whether or not it makes any sense or not. There are occasionally times as a senior operator that you are making decisions. It is ultimately accountable. And even as a board member, there are times when there are things that the board has to really weigh in on and agree to. But I would argue that those are fairly rare things. For the most part, the job is mentoring, coaching, guidance, challengi…

AI assessment note: “I've got to be cautious about being clear when I'm actually giving strong guidance”

Q Oh, you are far too kind and too charming, but I do want to kick off with a little bit on you. So tell me, how did you make your way into the world of venture, and how did you come to be an MD at GC today?

A Yeah, it's a good question, and I think it's an important question relative to how I got to General Catalyst as well in specific. But I'm a longtime operator, right? I was 20 plus years building software, building businesses, building teams, etc. And I was at Microsoft, and Microsoft before Satya was a little insular. Like, we're up there in the woods in Seattle, and we didn't really kind of get down to the valley very much, right? When I moved here in 2014, friends that I knew, people that had moved down here said, you really should meet some venture capitalists. Like, you should understand that part of the world. I'd just become the CTO of SAP, and I'm like, that makes sense. And I had friends set up meetings. Meetings number one, and number two, Reid Hoffman, Hemantinajah. I kid you not, I sit down for breakfast with Reed, and I'm like, so Reed, what is it you do? And he looks at me, he's like, you are new here, aren't you? And, you know, I started chuckled, right? But SAP was a great job, because everyone took the call from the CTO of SAP, right? And I was able to network, and I was able to learn. And when I left SAP, I was able to spend a lot of time with people, and a lot of time on things I was interested in, right? So I was able to kind of operate like an investor might. Spent time with the tier one VCs, including, of course, General Catalyst, looked at deals, went to M…

AI assessment note: “I was able to kind of operate like an investor might.”

Q to touch on one thing before we touch on remote work, and it's just we've mentioned Colonel, we've mentioned Camille, you have board seats at both, and board membership is not often talked about, I don't think, actually, and so I'd love to hear your thoughts. Like, how would you describe your style of board membership, and what does that look like to you in terms of your own style?

A I think it's a lot like senior management roles in a way. I ran 8000 person division at SAP, a couple thousand people at Dropbox, a couple thousand people at Microsoft, lots of different products, lots of different efforts. You can't be super hands-on and all that stuff, right? It just doesn't scale. So you're not day-to-day involved with these teams. So you have limited interactions. You don't have all the information. So the question is, how do you be helpful? How do you help make sure that they're heading the right direction? How do you help guide them and provide them value? Connecting the dots, guiding decisions, helping them hire. These are all kind of the obvious things. But what I think that I've tried to do more of is what I sort of think of as the Socratic method. Ask questions. Recognize that I don't have the answers. It's up to these leaders and these teams to find those answers. But I've seen a lot of these movies before. If it comes to a team that wants to start building a self-service experience, I've seen that movie a couple of times before, and I can ask the protagonist in this new movie, right, the founders, the leadership teams of these companies I'm working with, how they're thinking about the challenges that are in front of them. Our job is really to help them find their answers by being a focusing factor, right? Help them sort out their own thinking, not i…

AI assessment note: “It's leading without authority, and it's leading through mentorship, is sort of the mentality.”

Q Can I ask, how do you know when to let go? Because when you know things like you do, it's so easy to run with them and execute, and kind of do the job for them in some respects, and then they don't actually learn. How do you think about knowing when to take your hand off the tiller, and go from, like, guide to kind of observer?

A It's a question that's actually relevant to the operating arena as well. How do you feather that throttle on being involved and being super hands-on versus like mentoring, guiding, and coaching, etc.? I think a lot of it has to do with understanding what the outcomes you're really looking for are, and if you believe that a person or team really understands the outcomes that you're after, and they just need a little help with a system put in place to help push that forward, then you can very often let go. I mean, I've been in situations where I've set up a way of engaging on a problem and being very hands-on in the beginning. Every meeting, every discussion, Right? Helping, like, set the framework, do the math, whatever it is, but then over the course of a number of weeks, just slowly letting go. You give more and more room to the people who are picking up the mantle, and very often you can find yourself working your way out of being relevant in a lot of these engagements, which is good.

AI assessment note: “if you believe that a person or team really understands the outcomes”

Q know, there's such well-structured, well-managed organizations when you look at the different ones. When you think about kind of management takeaways for you from Especially the 20 years at Microsoft. Again, it's so hard asking me to distill, like, the biggest takeaway, which is, like, a horrible question to ask, and I'm cringing at asking it. But, like, what was the biggest takeaway in terms of management lesson for you?

A I would say the single biggest thing it taught me in my time there is that it's people. It's all about people, and it's always about people. At the end of the day, like, you have no ability to win long term unless you have the right people around you. And over and over again in my career at Microsoft, I was fortunate to have these great mentors and these great managers who Who helped teach me some skill in terms of building teams and leading people and kind of recognizing that every challenge that you have at the end of the day gets solved because you've married that problem against the exact right person to go solve it. And so much happened at Microsoft in my 20 years there. I mean, think about it, right? Department of Justice, antitrust. We built the Xbox business from nothing. We lost the Windows franchise to Apple. We led the business that grew from number five in market share to number two when I left and is now actually number one recently. I mean, just huge, huge, huge sea change happened. And at the end of the day, every one of those things that Microsoft did well, and every one of the things that we missed, comes down to a very, very, very small number of people.

AI assessment note: “the single biggest thing it taught me in my time there is that it's people”

Q few investments, what, seven or eight from GC now. We chatted before about the first few months in venture and then the first few years for kind of operators moving into venture. And it was really interesting. You said about two humps. Specifically. And I love this because I haven't heard it before. And so what did you mean by the two humps when it comes to like entering venture?

A Again, I'm just super lucky, right? I'm fortunate to have known people like John Lilly or Bill Corrin, who'd been operators who then joined venture and, you know, get some perspective and mentoring from them. And kind of, here's what I distilled. The two spots are kind of six months in and two years in. At the six month in mark, it's kind of, what am I doing exactly? Especially for a lot of people that come into venture, they show up for their first Monday or whatever, and they literally have nothing to do. There's no portfolio or There's no deal you're already pursuing. Like, it's kind of strange to go from operating roles where 30 hours of your week is programmatic. It's managing the system and operating the system. It's like this regular cadence to, I don't know, Monday partner meetings, like six hours a week or whatever, right? And to have so little of your time structured that way, it can be pretty jarring. I'm really lucky in that when I came in, I was already on a couple of boards for GC portfolio companies. That work sort of continues. I was able to jump in pretty quickly in part because Dropbox diaspora, other things that had kind of come across my way. So I was able to jump in pretty quickly and sort of start to get some things going. And so I didn't really hit that six month mark kind of wondering, how do I spend my time? And what am I really doing here? At that poin…

AI assessment note: “The two spots are kind of six months in and two years in.”

Q Can I ask, you know, when you have, like, very young founders in particular, maybe first-time founders, or just younger founders, you have such weight of experience that when you pose your questions, Even if they're posed as questions, the weight of your words are pretty heavy. Do you have to think through that and be very kind of cautious and deliberate in the weight of your own words?

A Yeah, it's funny, like, as an operator, many senior operators will tell you that they all had this similar experience, which is, you're in a meeting with a team, you make an offhand comment, you come back with this team, like, a month later, and you find out that they've been busy, like, off doing some crazy thing because of this comment you made. Cause they took it as direction, right? They took it as gospel. And so at some point in your career as an operator, as you go through this, you kind of learn, oh, I've got to be cautious about being clear when I'm actually giving strong guidance or I'm making a decision versus when I'm just showing curiosity. And one of the things I got very used to as an operating leader and that I'm accustomed to as a board member is posing these questions and being really clear. Like I am just curious. I don't know if this is the right thing to do or not, but I'm curious about the following thing. And let them take that ownership from that point and sort out whether or not it makes any sense or not. There are occasionally times as a senior operator that you are making decisions. It is ultimately accountable. And even as a board member, there are times when there are things that the board has to really weigh in on and agree to. But I would argue that those are fairly rare things. For the most part, the job is mentoring, coaching, guidance, challengi…

AI assessment note: “you kind of learn, oh, I've got to be cautious about being clear”

Q things that first-time founders often struggle with, one, the ways of words, and two is actually just kind of board management and board opt Optimization. It's like you never learn to manage a board anywhere in life. You've worked with some of the very best founders, as you said, like Bill, Satya, Drew. It's a pretty impressive list. How do the very best founders manage their boards from your perspective?

A The number one piece of advice I can give founders is around managing their boards is don't surprise anybody. Just no surprises. Even good surprises erode trust. I've seen situations where you walk up a couple months later and you've been engaged with them. You've been talking about other things and then they pop up with this Hey, we've actually, like, beat these revenue targets by this, like, massive amount, and you're kind of like, whoa, how'd that happen? Because we were still wrong about something, so it's worth reflecting on why we weren't correct. Even if it's a good thing, you always want to know why, why, why, why, why, right? So no surprises, that's kind of number one. Board members don't really like feeling like they're being corralled, so board members don't like the sense of being kind of, like, led around by a bridal, and yet we have to be to a large extent. That's a little bit of the dichotomy that founders faced Dealing with their boards. But I think when this is done well, for the board member, it feels like you have the space to think, to collaborate, to contribute. More like improv. If you want to compare this to different kinds of bands, right, it's more like jazz, less like orchestra. When it's not done well, you feel like you're on an amusement park ride, and you really can't have no control over what's going on. You're more of a passenger in their thing th…

AI assessment note: “The number one piece of advice I can give founders is around managing their boards”

Q know, there's such well-structured, well-managed organizations when you look at the different ones. When you think about kind of management takeaways for you from Especially the 20 years at Microsoft. Again, it's so hard asking me to distill, like, the biggest takeaway, which is, like, a horrible question to ask, and I'm cringing at asking it. But, like, what was the biggest takeaway in terms of management lesson for you?

A I would say the single biggest thing it taught me in my time there is that it's people. It's all about people, and it's always about people. At the end of the day, like, you have no ability to win long term unless you have the right people around you. And over and over again in my career at Microsoft, I was fortunate to have these great mentors and these great managers who Who helped teach me some skill in terms of building teams and leading people and kind of recognizing that every challenge that you have at the end of the day gets solved because you've married that problem against the exact right person to go solve it. And so much happened at Microsoft in my 20 years there. I mean, think about it, right? Department of Justice, antitrust. We built the Xbox business from nothing. We lost the Windows franchise to Apple. We led the business that grew from number five in market share to number two when I left and is now actually number one recently. I mean, just huge, huge, huge sea change happened. And at the end of the day, every one of those things that Microsoft did well, and every one of the things that we missed, comes down to a very, very, very small number of people.

AI assessment note: “the single biggest thing it taught me in my time there is that it's people.”

Q I'm not even the one who sends like, you know, ridiculous messages at three in the morning with new projects that we need to do, and then like, just expect this kind of trail of destruction to be left behind me, and I'm a shit manager. What's the difference in your mind between leadership and management, and how should I think about that, and how should we think about that?

A Yeah, I think it's pretty simple. Leadership is about followership. Leadership is really about if there comes a moment when a group of people need to head in some direction, Do you have the followership to lead those people, to literally guide those people in that direction, push in that direction? Management is about all the stuff that it takes to have a functioning, cohesive system of people. And ultimately, so the very best people that I've worked with over the years, that includes Gates, it includes McDermott, it includes Satya, it includes so many people, are both great leaders and great managers. And yeah, they spike a little bit one or the other, but saying that direction, getting the followership versus just setting up a system. That is capable of doing great work is also a different discipline, different art.

AI assessment note: “Leadership is about followership... Management is about all the stuff that it takes”

Q the brilliant elements of working with Quentin is he has this phenomenal ability to know which hat to put on and when, the two hats being VC and operator, and he says, like, obviously you have both very, very high quality, but you know when to put them on and why. When you think about deciding when to put it on and why, how do you think about that today?

A Yeah, that's a great question, and Commure is a unique-ish example in the sense that Commure is a company that Hamath and I started within General Catalyst. It's a quote, what we call hatch, Right. It's an incubation from within the firm. And so there's typically a little bit more hands on in those scenarios, but this comment applies really to everybody. Like, do they need a thought partner, a coach, a guide, or do they need someone to roll up their sleeves and help them do some of the digging? At any given time, there's a couple of companies I'm working pretty closely with. I'm working on customer development, or I'm helping guide product and technical strategy, or I'm helping doing hiring. Right. And it's just what they need. And I'm fortunate to have the experience to be helpful. So I'm privileged enough to be able to dive in. And I actually see being asked to help as a sign of this ultimate trust and partnership. And it's very fulfilling when you can do it, but you have to kind of really know when to let go, right? Ultimately, again, it's their company, it's their decisions to make. So I sort of tune into, are they looking for advice, or do they really need someone to pick up a shovel and help out?

AI assessment note: “I sort of tune into, are they looking for advice, or do they really need someone”

Q like, incremental loading on. I do want to ask, in terms of the kind of the companies that you work with, we mentioned Camille, we mentioned Kernel earlier. Bluntly, compared to the rest of the venture ecosystem, they're quite out there, Quentin. My question to you is, like, are we fundamentally, or is the ecosystem fundamentally doing venture investing, or are we doing, like, incremental innovation investing for IRR multiples?

A Speaking of Kernel, it's worth pausing on that for a second. Kernel is truly venture capital, right, in the sense that the market that makes it really interesting is Not only as an investment, but as an impact to our species come as it creates that market. Ultimately, venture capital, we get paid to underwrite risk. Otherwise, we'd be retail stock traders, I guess. And the risks are different, different stages. For something like Kernel, the insight that Brian had around, we do not really understand the brain. And I mean that in really both senses. As an organ, we don't understand it as an organ, like physically. Like if some harm comes to it, we don't really understand it physically, and we don't understand it as a collection of software. We understand neither of these things very well. But what if we knew how the brain actually worked, and what if you could understand how the software was running? Imagine what you could do, right? You could manage your emotions better. You could learn better. You could develop better. You could recover better. Like, all this unlock can happen as big as an opportunity as in genomics, right? When we start to understand genes, to this day, we're still learning how to take advantage of that knowledge day to day in the medical industry, in the medical research industry, and the same thing will come for the brain. So I do believe that there are som…

AI assessment note: “Kernel is truly venture capital, right, in the sense that... we get paid to underwrite risk.”

Q is trust and delegation, and it's, I struggle to delegate, and this sounds really arrogant, but I just know what I do, and I know how to do it, and I struggle to delegate because I don't trust anyone to do it as well as I think I can do it. Can you advise me? How do I get over this? Because it's actually inhibiting the scaling of my business.

A It's a good question, and it's actually one I think so many people struggle through. At some point in their careers. I remember this was like my first few years at Microsoft. I'd been made into an engineering lead and had this little team that I was working with. Right. And I remember having this moment where I was in a one-on-one with someone that worked for me and they're supposed to get this thing done. They hadn't got done the way I wanted it done. Something like this. And after the one-on-one, I just went in and just did it myself. And then I was having a one-on-one with my boss, this guy named George Santino, great guy. And I'm all like proud of myself. You know, I'm like, then I went and I like fixed it. Right. I like straighten it out. And he looks at me deadpan. He's like, well, that's a total failure. And I'm like, what do you mean? Like, I'm a hero. He's like, no, you're the donkey, not the hero. You rob this person of this learning opportunity. You rob them of the skill development. And instead of paying you to do the job I want you to do, you're now doing someone else's job instead. Like, it's a total failure. And it really reset my mind, right? It really changed my mindset around the job as a manager. And we can talk about leadership versus management, but the job as a manager is to develop The capabilities underneath you at all times. And yes, it does mean that s…

AI assessment note: “the job as a manager is to develop The capabilities underneath you at all times.”

Q Can I ask, how do you know when to let go? Because when you know things like you do, it's so easy to run with them and execute, and kind of do the job for them in some respects, and then they don't actually learn. How do you think about knowing when to take your hand off the tiller, and go from, like, guide to kind of observer?

A It's a question that's actually relevant to the operating arena as well. How do you feather that throttle on being involved and being super hands-on versus like mentoring, guiding, and coaching, etc.? I think a lot of it has to do with understanding what the outcomes you're really looking for are, and if you believe that a person or team really understands the outcomes that you're after, and they just need a little help with a system put in place to help push that forward, then you can very often let go. I mean, I've been in situations where I've set up a way of engaging on a problem and being very hands-on in the beginning. Every meeting, every discussion, Right? Helping, like, set the framework, do the math, whatever it is, but then over the course of a number of weeks, just slowly letting go. You give more and more room to the people who are picking up the mantle, and very often you can find yourself working your way out of being relevant in a lot of these engagements, which is good.

AI assessment note: “if you believe that a person or team really understands the outcomes that you're after”

Q to touch on one thing before we touch on remote work, and it's just we've mentioned Colonel, we've mentioned Camille, you have board seats at both, and board membership is not often talked about, I don't think, actually, and so I'd love to hear your thoughts. Like, how would you describe your style of board membership, and what does that look like to you in terms of your own style?

A I think it's a lot like senior management roles in a way. I ran 8000 person division at SAP, a couple thousand people at Dropbox, a couple thousand people at Microsoft, lots of different products, lots of different efforts. You can't be super hands-on and all that stuff, right? It just doesn't scale. So you're not day-to-day involved with these teams. So you have limited interactions. You don't have all the information. So the question is, how do you be helpful? How do you help make sure that they're heading the right direction? How do you help guide them and provide them value? Connecting the dots, guiding decisions, helping them hire. These are all kind of the obvious things. But what I think that I've tried to do more of is what I sort of think of as the Socratic method. Ask questions. Recognize that I don't have the answers. It's up to these leaders and these teams to find those answers. But I've seen a lot of these movies before. If it comes to a team that wants to start building a self-service experience, I've seen that movie a couple of times before, and I can ask the protagonist in this new movie, right, the founders, the leadership teams of these companies I'm working with, how they're thinking about the challenges that are in front of them. Our job is really to help them find their answers by being a focusing factor, right? Help them sort out their own thinking, not i…

AI assessment note: “what I sort of think of as the Socratic method. Ask questions.”

Q this industry and just being a lot more authentic. In terms of vulnerability, one, for me, it's like, you know, I'm a recent board member. Last two years have been the first boards that I've joined, Big vulnerability that I feel, and I am very keen to be the best board member that I can be. What do you think about your vulnerabilities? What do you feel vulnerable about, Quentin?

A I'm new to this job, and I'm learning, and one of the things I like to do when I'm learning something new is surround myself with people who are good at those jobs and are willing to teach, and so I feel pretty good about how I'm kind of set up inside General Catalyst in the industry to learn to do a good job at being a venture capitalist, but it is a vulnerable thing. I mean, I've done a twenty-something year operating career. I'm shifting careers all together. It is a fundamentally different job to be an MD, right? To be a general partner at a venture firm. And that's a fairly vulnerable thing, right? The easy path for me would have been take another big operating gig, right? As the CEO of something and just ride up the next 15 years. But I really wanted to learn to do something different. It's not that I was bored or unchallenged. It was just simply, I could see how that plays out. And so the vulnerability for me right now is like, it's scary to take on something that's brand new this way.

AI assessment note: “I'm shifting careers all together. It is a fundamentally different job to be an MD”

Q is trust and delegation, and it's, I struggle to delegate, and this sounds really arrogant, but I just know what I do, and I know how to do it, and I struggle to delegate because I don't trust anyone to do it as well as I think I can do it. Can you advise me? How do I get over this? Because it's actually inhibiting the scaling of my business.

A It's a good question, and it's actually one I think so many people struggle through. At some point in their careers. I remember this was like my first few years at Microsoft. I'd been made into an engineering lead and had this little team that I was working with. Right. And I remember having this moment where I was in a one-on-one with someone that worked for me and they're supposed to get this thing done. They hadn't got done the way I wanted it done. Something like this. And after the one-on-one, I just went in and just did it myself. And then I was having a one-on-one with my boss, this guy named George Santino, great guy. And I'm all like proud of myself. You know, I'm like, then I went and I like fixed it. Right. I like straighten it out. And he looks at me deadpan. He's like, well, that's a total failure. And I'm like, what do you mean? Like, I'm a hero. He's like, no, you're the donkey, not the hero. You rob this person of this learning opportunity. You rob them of the skill development. And instead of paying you to do the job I want you to do, you're now doing someone else's job instead. Like, it's a total failure. And it really reset my mind, right? It really changed my mindset around the job as a manager. And we can talk about leadership versus management, but the job as a manager is to develop The capabilities underneath you at all times. And yes, it does mean that s…

AI assessment note: “the job as a manager is to develop The capabilities underneath you at all times”

Q the brilliant elements of working with Quentin is he has this phenomenal ability to know which hat to put on and when, the two hats being VC and operator, and he says, like, obviously you have both very, very high quality, but you know when to put them on and why. When you think about deciding when to put it on and why, how do you think about that today?

A Yeah, that's a great question, and Commure is a unique-ish example in the sense that Commure is a company that Hamath and I started within General Catalyst. It's a quote, what we call hatch, Right. It's an incubation from within the firm. And so there's typically a little bit more hands on in those scenarios, but this comment applies really to everybody. Like, do they need a thought partner, a coach, a guide, or do they need someone to roll up their sleeves and help them do some of the digging? At any given time, there's a couple of companies I'm working pretty closely with. I'm working on customer development, or I'm helping guide product and technical strategy, or I'm helping doing hiring. Right. And it's just what they need. And I'm fortunate to have the experience to be helpful. So I'm privileged enough to be able to dive in. And I actually see being asked to help as a sign of this ultimate trust and partnership. And it's very fulfilling when you can do it, but you have to kind of really know when to let go, right? Ultimately, again, it's their company, it's their decisions to make. So I sort of tune into, are they looking for advice, or do they really need someone to pick up a shovel and help out?

AI assessment note: “I sort of tune into, are they looking for advice, or do they really need”

Q Talking about kind of being partners and builders there, kind of a crucial part of being any partner and builder with someone is the element of trust, which you touched on earlier. How do you think about with the compression of fundraising timelines, building that really deep sense of trust with a founder in what now is very short timelines?

A Yeah, that's a tough one. I think the pandemic has really We've changed a little bit about the cadence that we're in. If you think about the way things used to be, we'd get in touch with someone. We'd have them come by the office. We spend a little time. We get interested. We schedule another meeting. Maybe we go to their site, right? Maybe we go to their offices. I think it's a little time to schedule. Maybe bring a partner. So there's like kind of a multi-body scheduling problem. You get more interested. You want to spend more time. Maybe you have dinner. Like this whole thing would take weeks and weeks and weeks, and you have a lot of these in-person encounters along the way to sort of build that trust. With the pandemic, Going on and everyone kind of sheltering in place still in travel, not really being a norm and whatever. You have to kind of rethink a lot of this, right? So you have to think about how do I get enough just one-on-one time with that founder? Because the little moments have been robbed, right? Like they greet you down the lobby of their building and you're 10 minutes early for a meeting. You're sitting there. You're kind of getting to know them, right? Before the meeting content starts, right? So how do you create those moments? And I think one of the things that I've learned to do is use the phone more. I am using the phone more than I did before this whole…

AI assessment note: “one of the things that I've learned to do is use the phone more.”

Q How do you think we'll collaborate around the in-person time and not have scattered time, which is obviously less efficient?

A I think we're going to invent new ways of working terminology. There'll be things like, how many in-person days are there? For this department of this company. It's a kind of a new interview question in a way, right? And I think what's going to happen is we're going to use more collaborative space, bring people together for the team building, for the problem solving, for the strategy setting, and then let people kind of fan out and do their jobs. And that'll go on for, I don't know, like a week, two weeks, a month, a quarter, and then bring people back. So we're going to use bigger spaces with more people in them, ironically, to do that kind of team building collaboration, but then let kind of people fan out and go do the heavy lifting.

AI assessment note: “bring people together for the team building, for the problem solving, for the strategy setting”

Q Talking about kind of being partners and builders there, kind of a crucial part of being any partner and builder with someone is the element of trust, which you touched on earlier. How do you think about with the compression of fundraising timelines, building that really deep sense of trust with a founder in what now is very short timelines?

A Yeah, that's a tough one. I think the pandemic has really We've changed a little bit about the cadence that we're in. If you think about the way things used to be, we'd get in touch with someone. We'd have them come by the office. We spend a little time. We get interested. We schedule another meeting. Maybe we go to their site, right? Maybe we go to their offices. I think it's a little time to schedule. Maybe bring a partner. So there's like kind of a multi-body scheduling problem. You get more interested. You want to spend more time. Maybe you have dinner. Like this whole thing would take weeks and weeks and weeks, and you have a lot of these in-person encounters along the way to sort of build that trust. With the pandemic, Going on and everyone kind of sheltering in place still in travel, not really being a norm and whatever. You have to kind of rethink a lot of this, right? So you have to think about how do I get enough just one-on-one time with that founder? Because the little moments have been robbed, right? Like they greet you down the lobby of their building and you're 10 minutes early for a meeting. You're sitting there. You're kind of getting to know them, right? Before the meeting content starts, right? So how do you create those moments? And I think one of the things that I've learned to do is use the phone more. I am using the phone more than I did before this whole…

AI assessment note: “one of the things that I've learned to do is use the phone more.”

Q like, incremental loading on. I do want to ask, in terms of the kind of the companies that you work with, we mentioned Camille, we mentioned Kernel earlier. Bluntly, compared to the rest of the venture ecosystem, they're quite out there, Quentin. My question to you is, like, are we fundamentally, or is the ecosystem fundamentally doing venture investing, or are we doing, like, incremental innovation investing for IRR multiples?

A Speaking of Kernel, it's worth pausing on that for a second. Kernel is truly venture capital, right, in the sense that the market that makes it really interesting is Not only as an investment, but as an impact to our species come as it creates that market. Ultimately, venture capital, we get paid to underwrite risk. Otherwise, we'd be retail stock traders, I guess. And the risks are different, different stages. For something like Kernel, the insight that Brian had around, we do not really understand the brain. And I mean that in really both senses. As an organ, we don't understand it as an organ, like physically. Like if some harm comes to it, we don't really understand it physically, and we don't understand it as a collection of software. We understand neither of these things very well. But what if we knew how the brain actually worked, and what if you could understand how the software was running? Imagine what you could do, right? You could manage your emotions better. You could learn better. You could develop better. You could recover better. Like, all this unlock can happen as big as an opportunity as in genomics, right? When we start to understand genes, to this day, we're still learning how to take advantage of that knowledge day to day in the medical industry, in the medical research industry, and the same thing will come for the brain. So I do believe that there are som…

AI assessment note: “there are some things that are truly venture capital”