The Exchanges

Q journey in itself. We have mentioned Will a couple of times from Stripe and he said in particular, On joining Sequoia, how impressed you've been with the team in so many different parts. I really wanted to kind of dig in on this. And in terms of the Sequoia team, I guess a couple of different elements, but like, what have you been most impressed with? Let's start with that.

A Yeah. So I mentioned mission earlier, and the most impressive thing to me about Sequoia is this single-minded devotion to the mission, which as far as I know, has been pretty identical since 1972, which is we helped the daring build legendary companies. From idea to IPO and beyond. And Harry, I mean, everything is built around this. The culture is so purposeful. I mean, it's in the behavior that's rewarded. It's in the stories that are told. And then this devotion to the mission leads to things like partnering with Patrick and John and Will and Claire. But I mean, at the time, Patrick and John at Stripe, when all they had was an idea and not a single line of code, because they were remarkable and they were daring. And Sequoia believed that they were going to build something of consequence. And we had to partner with them. And so That's the piece that's been most impressive to me.

AI assessment note: “the most impressive thing to me about Sequoia is this single-minded devotion”

Q Okay, question. There's always surprising elements. What have you found the most surprising?

A Yeah, I knew this coming in, but I've definitely still been pleasantly surprised by it, which is the level of collaboration. Sequoia wins as a team and loses as a team, and to use a sports analogy, I think a lot of places do talk about being a team, a lot of venture firms, but my observation is they seem a bit more like a golf team. Everyone does their own thing, and then You add up the scores at the end and hope that you win. Sequoia is more like a basketball team. Your strength or your superpower is added to a team with the sole focus of making sure that companies win. And the only thing that matters is the team success. This is reinforced by things that seem like they are one-offs, but they're not, they're critical. This is reinforced by things like unanimous decision-making, which means we all need to be bought in when we decide to partner with a company. And it's reinforced when entrepreneurs ask somebody at Sequoia, hey, if I work with Sequoia, who will my board member be? And the answer is always the same, which is whoever you want. You get to choose. We just want to support you, and no matter who you choose, you're going to get all of Sequoia no matter what. That means that if you need help with go-to-market, we're going to have Carl talk to you, who's scaled VMware from forty million in revenue to six billion. If you need help with engineering, we're going to have Bill…

AI assessment note: “I've definitely still been pleasantly surprised by it, which is the level of collaboration.”

Q and every great company has to have a great leader? And as we said, I spoke to Cigar, who's obviously CFO at Instagram now, and he said that when it comes to leadership, your superpower above all others is your ability to prioritize so ruthlessly. I'm interested in kind of double clicking on this. How do you think about the importance of saying no as a founder and leader fundamentally?

A It's a lesson that comes from experience, Harry, which is you start out, it feels so good to say yes. Somebody wants to do something. Yeah, let's do that too. But the problem is, is that that feeling is fleeting. Because nothing gets done when you have seven priorities and 10 sub priorities and it's on a Google sheet because nobody knows what's actually important. And so I remember this time at Instacart where we had six company priorities in a quarter and a month into the quarter or halfway into the quarter, we weren't moving nearly as fast as we wanted on any of them. And so a quarter and I just sat down in a room and said, if we can only get one thing done the rest of the quarter, what would it be? And the answer was so obvious. And we were like, well, let's just go do that. Let's not not get that done because we wanted to say we're going to work on more things. And so we literally had all hands the next day and we rallied everyone around that one goal. And that's all it took to get us moving again. And so I think that focus is dramatically underrated. And I think that it's one of those things that it is a little bit more painful up front to say no and to pick the one thing. But I think the outcomes that you get are so much better. And I think over time you can make that one to two, but I think that people sometimes think that you're going to go from eight to 10. And in my e…

AI assessment note: “it is a little bit more painful up front to say no”

Q journey in itself. We have mentioned Will a couple of times from Stripe and he said in particular, On joining Sequoia, how impressed you've been with the team in so many different parts. I really wanted to kind of dig in on this. And in terms of the Sequoia team, I guess a couple of different elements, but like, what have you been most impressed with? Let's start with that.

A Yeah. So I mentioned mission earlier, and the most impressive thing to me about Sequoia is this single-minded devotion to the mission, which as far as I know, has been pretty identical since 1972, which is we helped the daring build legendary companies. From idea to IPO and beyond. And Harry, I mean, everything is built around this. The culture is so purposeful. I mean, it's in the behavior that's rewarded. It's in the stories that are told. And then this devotion to the mission leads to things like partnering with Patrick and John and Will and Claire. But I mean, at the time, Patrick and John at Stripe, when all they had was an idea and not a single line of code, because they were remarkable and they were daring. And Sequoia believed that they were going to build something of consequence. And we had to partner with them. And so That's the piece that's been most impressive to me.

AI assessment note: “the most impressive thing to me about Sequoia is this single-minded devotion to the mission”

Q and every great company has to have a great leader? And as we said, I spoke to Cigar, who's obviously CFO at Instagram now, and he said that when it comes to leadership, your superpower above all others is your ability to prioritize so ruthlessly. I'm interested in kind of double clicking on this. How do you think about the importance of saying no as a founder and leader fundamentally?

A It's a lesson that comes from experience, Harry, which is you start out, it feels so good to say yes. Somebody wants to do something. Yeah, let's do that too. But the problem is, is that that feeling is fleeting. Because nothing gets done when you have seven priorities and 10 sub priorities and it's on a Google sheet because nobody knows what's actually important. And so I remember this time at Instacart where we had six company priorities in a quarter and a month into the quarter or halfway into the quarter, we weren't moving nearly as fast as we wanted on any of them. And so a quarter and I just sat down in a room and said, if we can only get one thing done the rest of the quarter, what would it be? And the answer was so obvious. And we were like, well, let's just go do that. Let's not not get that done because we wanted to say we're going to work on more things. And so we literally had all hands the next day and we rallied everyone around that one goal. And that's all it took to get us moving again. And so I think that focus is dramatically underrated. And I think that it's one of those things that it is a little bit more painful up front to say no and to pick the one thing. But I think the outcomes that you get are so much better. And I think over time you can make that one to two, but I think that people sometimes think that you're going to go from eight to 10. And in my e…

AI assessment note: “it is a little bit more painful up front to say no and to pick the one thing”

Q like, insecurities and the kind of vulnerabilities, often new VCs are insecure, concerned, nervous about their first deal. It's a very common thing. I was chatting to Will Daybreak before, and he specifically asked, and Will wanted to hear your thoughts on this, and his question was, how did you approach your first deal at Sequoia? Were you nervous, and what did that mindset and process look like for you?

A Yeah, it's a great question, which I actually think, and I don't know what it would be like anywhere else. I think Sequoia helps on this nerves point in sort of a counterintuitive way, because the expectation is that you go all in on the investments that you do. And with that expectation, you get to be super selective on the companies with whom you partner, because people view it as a 10 or 15 or 20 year partnership. And so you are allowed to keep the bar and are encouraged to keep the bar super high. We actually partnered with them first at The Seed. And they've just consistently blown us away. I think that when we talk about the people we like to invest in at Sequoia, we talk about investing in slope rather than intercept. And I think Samir and Runek slope is so incredible that it actually made it quite an easy decision for me of, yeah, absolutely. We want to go all in on this. And, and so I would say, I think Sequoia's approach to go all in, keep the bar high combined with getting to meet Samir and Runek and just believing in them. Made it for me a lot easier than it could be.

AI assessment note: “I think Sequoia helps on this nerves point in sort of a counterintuitive way”

Q I mean, that is so kind of you. May the bromance blossom, but I do want to start today and pretend to be blissfully ignorant on how you got into the world of Venture. So for some context, how did you make your way into the world of Venture and come to your partner at Sequoia today?

A Well, I wish the story was as interesting as starting a podcast when I was 18, but, you know, we had to all be Harry Stebbings. So, I joined Sequoia last year after four and a half years at Instacart. And, you know, in 2015, I met at Porva, and he shared the vision for what he wanted Instacart to be with me. And honestly, Harry, I was captivated. I was inspired. And so, it was just a team I wanted to join, a company I wanted to help build, and I was lucky enough to be the COO and CFO there. That four and a half years is a crazy time for Instacart. We went through hyper growth. We had all the fun that came along with that. And we also saw all the issues that came along with that. I got to know Sequoia because Sequoia has been partnered with Instacart since the earliest days. And I just really liked their style and how they partnered with us. And so when I decided to get back to investing and really work with the next generation of founders, Sequoia was kind enough to let me join the team.

AI assessment note: “I got to know Sequoia because Sequoia has been partnered with Instacart since the earliest”

Q I mean, that is so kind of you. May the bromance blossom, but I do want to start today and pretend to be blissfully ignorant on how you got into the world of Venture. So for some context, how did you make your way into the world of Venture and come to your partner at Sequoia today?

A Well, I wish the story was as interesting as starting a podcast when I was 18, but, you know, we had to all be Harry Stebbings. So, I joined Sequoia last year after four and a half years at Instacart. And, you know, in 2015, I met at Porva, and he shared the vision for what he wanted Instacart to be with me. And honestly, Harry, I was captivated. I was inspired. And so, it was just a team I wanted to join, a company I wanted to help build, and I was lucky enough to be the COO and CFO there. That four and a half years is a crazy time for Instacart. We went through hyper growth. We had all the fun that came along with that. And we also saw all the issues that came along with that. I got to know Sequoia because Sequoia has been partnered with Instacart since the earliest days. And I just really liked their style and how they partnered with us. And so when I decided to get back to investing and really work with the next generation of founders, Sequoia was kind enough to let me join the team.

AI assessment note: “when I decided to get back to investing... Sequoia was kind enough to let me join”

Q Tell me, what would you most like to change about the world of Venture Ravi?

A You know, we've touched on it, and it's not true for everyone, but I think that some people in our industry treat founders and companies like deals, and I've been on the other end when people call you or email you and tell you they're passing on your company, and I think that's fine. But I think sometimes they feel the need to convince you that your business was bad so that they can feel like they're right. And I think that that just, it misses the whole point of companies are not numbers on a page. They're groups of people devoting their careers to a mission. And after I get off the phone with you as an investor, if I'm working in a company, I got to go back to my desk and go do work. I got to go to an all hands and talk about why what we're doing is great. And so I think that investors would be best served to remember that Companies do not exist for their pleasure. Companies exist for people to do their life's work. And when you do decide it's not for you, that it's not about proving that you're right. You got to genuinely hope that this thing does great because the people are still working there, even if you're not going to invest in it.

AI assessment note: “investors would be best served to remember that Companies do not exist for their pleasure”

Q told you about this earlier before deleting this when anyone criticized me about it, but I tweeted actually about the dangers of vision because actually you can often always exceed the vision and it can almost limit and put mental constraints around what you can achieve. Would you agree with that? And how do you think about kind of the pros and cons of vision and how you evaluate it?

A It's interesting, Harry. I actually, I would tell you I agree with a part of it, and I don't agree with a part of it, but I bet if we go through it deeply, you and I will end up in the same place, which is, I think that vision is really important, but I think that you can't be locked to it, which means you need a vision to get people excited about joining your company. You need a vision to get investors excited. You need to be able to tell the story of why your company matters, but you also need to be able to adapt if things change, and you can't be locked into that when the environment changes around you, and so When I say that I am captivated or inspired by a vision, it's not that that's the only way that the company can be built. It's that that story and that big picture resonates with me. It's a world that I want to live in. And I think that the part of the vision, for instance, that Apoorva gave that resonated with me was, doesn't it seem crazy to you that we shop for groceries the same way we shopped for them 80 years ago? Don't you want to live in a world where the store changes every time you quote unquote walk into it? That it's built just for you, that it knows what you want, that it recommends different things. Don't you want to live in a world where you could spend all this time with your kids? I have three sons, as you know, where you could spend all this time with…

AI assessment note: “I agree with a part of it, and I don't agree with a part”

Q know I need to hire the best, but I also just need to hit target for next quarter. And bluntly, I don't have the timelines in place to make that happen. How do you think about the balance between filling seats, but also maintaining quality bar? And it's something that I think Stripe's done so well in terms of keeping up just the velocity, but also keeping up the quality.

A Yeah. I think that Stripe is absolutely inspirational on this topic. And I personally, I think they've done it the right way, which I think they are willing to deal with the pain of not filling a spot because they respect that spot so much that they're only going to put somebody great in it, and I think that's the right approach. I personally think that trying to hit targets over hiring the best team, I think it's a real mistake, and I think it's short-term thinking that doesn't scale, and it's very normal. I've done it. I've made that mistake. But the lesson you learn is if you're trying to build something enduring and great, I think you really do have to focus on getting the right team. And I think that that comment from earlier around the compounding is really important here because the instant you put somebody in the seat who's not that great for your org, I think that you all of a sudden have a real risk that who are they going to go higher? And I don't think it's something that's that easy to go and fix. So I end up being somebody who pushes pretty hard on Why is this person going to elevate the org? Why is this person going to be somebody who we can learn from? Why is this somebody that we would be delighted to introduce that at all hands and proud to talk about them coming and joining our company?

AI assessment note: “trying to hit targets over hiring the best team, I think it's a real mistake”

Q I have to ask, sorry, too interested by this. What do you mean by slope, not intersect? Is that lines, not doors? How do you think about that from an investment perspective?

A Yeah. So I think it's not about where the person is today. It's about where we think they can be in five years or 10 years or 15 years. And so with Samir and Runik, who are very young, I mean, I think we made our series A investment when they were both 19 years old. Their clock speed, their speed of learning, their speed of generating insights, how much better they are today than they were six months ago, and how much better they will continue to be in six months when they're already great. That's the kind of stuff that makes us excited. It's about this, how steep their slope is, is what we get excited about at Sequoia because it's such a long-term thing. So it matters a lot less what the business is today. It's about what the business can be in the future. And I think that when you have founders who blow you away, you're almost giddy because it's very hard to think about what it could be, but all the possibilities are good.

AI assessment note: “It's not about where the person is today. It's about where we think”

Q told you about this earlier before deleting this when anyone criticized me about it, but I tweeted actually about the dangers of vision because actually you can often always exceed the vision and it can almost limit and put mental constraints around what you can achieve. Would you agree with that? And how do you think about kind of the pros and cons of vision and how you evaluate it?

A It's interesting, Harry. I actually, I would tell you I agree with a part of it, and I don't agree with a part of it, but I bet if we go through it deeply, you and I will end up in the same place, which is, I think that vision is really important, but I think that you can't be locked to it, which means you need a vision to get people excited about joining your company. You need a vision to get investors excited. You need to be able to tell the story of why your company matters, but you also need to be able to adapt if things change, and you can't be locked into that when the environment changes around you, and so When I say that I am captivated or inspired by a vision, it's not that that's the only way that the company can be built. It's that that story and that big picture resonates with me. It's a world that I want to live in. And I think that the part of the vision, for instance, that Apoorva gave that resonated with me was, doesn't it seem crazy to you that we shop for groceries the same way we shopped for them 80 years ago? Don't you want to live in a world where the store changes every time you quote unquote walk into it? That it's built just for you, that it knows what you want, that it recommends different things. Don't you want to live in a world where you could spend all this time with your kids? I have three sons, as you know, where you could spend all this time with…

AI assessment note: “I agree with a part of it, and I don't agree with a part of it”

Q know I need to hire the best, but I also just need to hit target for next quarter. And bluntly, I don't have the timelines in place to make that happen. How do you think about the balance between filling seats, but also maintaining quality bar? And it's something that I think Stripe's done so well in terms of keeping up just the velocity, but also keeping up the quality.

A Yeah. I think that Stripe is absolutely inspirational on this topic. And I personally, I think they've done it the right way, which I think they are willing to deal with the pain of not filling a spot because they respect that spot so much that they're only going to put somebody great in it, and I think that's the right approach. I personally think that trying to hit targets over hiring the best team, I think it's a real mistake, and I think it's short-term thinking that doesn't scale, and it's very normal. I've done it. I've made that mistake. But the lesson you learn is if you're trying to build something enduring and great, I think you really do have to focus on getting the right team. And I think that that comment from earlier around the compounding is really important here because the instant you put somebody in the seat who's not that great for your org, I think that you all of a sudden have a real risk that who are they going to go higher? And I don't think it's something that's that easy to go and fix. So I end up being somebody who pushes pretty hard on Why is this person going to elevate the org? Why is this person going to be somebody who we can learn from? Why is this somebody that we would be delighted to introduce that at all hands and proud to talk about them coming and joining our company?

AI assessment note: “trying to hit targets over hiring the best team, I think it's a real mistake”

Q you're like with teams, hey, this is your project to own, go make it happen, go run with it within these parameters, and you want them to be as aggressive and to be as ambitious as possible, but you also don't want them to have this fear of failure and not hitting targets. How do you think about kind of having the accountability, but also not constraining ambition when delegating?

A That's tough. I think that the first thing for me is the most ambitious people, they want the hardest problem. They want to have the ball. They want to be accountable for something. And so I try to look for people that really want to have that role. And then what I have found to be helpful is to let them drive the interaction with leadership on the topic, which is to say, look, I want to check in with you once a week, but you tell me what you need. We got to get this done over this time period, and if you tell me you want to go off and do it, that's cool. My normal way of doing it is like this, but you tell me what it is to be helpful. And I think that one of the things for me that I think you have to do is build that relationship of trust where they know you have their back. I think one of the things your team needs to know is you desperately want them to succeed. This is not a test. You know, it's funny. People think about this in interviews. When you're going to go interview somewhere, generally you're nervous because you're thinking that the person wants to find a way to stump you. And Harry, you know this when you're building your team, when you're interviewing somebody, you desperately want them to be great. All you want them to do is to blow you away. You don't want to stump them. And so interestingly, I think for accountability mechanisms, I think it's important for the…

AI assessment note: “build that relationship of trust where they know you have their back”

Q last few years, especially kind of as I've kind of been developing invention. I guess my question to you is on the theme of kind of leadership and And strong leadership. There's also insecurity within everyone. How do you think about insecurities in leadership? And what's been some of your lessons through, I guess, the Instacart journey, and then also now seeing it on the other side as a VC?

A Yeah. I mean, Harry, one of the things I respect the most about you is your willingness to talk about those things. I mean, I think that that makes a big difference to people to hear somebody that they view to be successful and someone like you who absolutely has done these amazing things. Talking about things that they're not great at or things that they're insecure about. And so for me, I think it comes down to authenticity. I don't think people expect their leaders to have all the answers, but I do think that they expect their leaders to be honest with them. And I think that is a absolutely reasonable and good expectation. And so when I was an Instacart, I used to share mistakes that I'd make with the company in all hands, because we wanted to have a culture where people would try things. And the best way for me to model that was to tell people sometimes we're lucky. Hey, we messed up on this. At Sequoia, this is not exactly what you asked me, but it is the thing I thought of. At Sequoia, one of our partners late last year shared their three 60 feedback with all of us at a partner meeting and then asked, can you help me get better on these? I mean, I thought that took just incredible strength and it made me gain even more respect for the person. And so I think on these kinds of things, I think people respond to authenticity. I think they crave these real human interactions. …

AI assessment note: “when I was an Instacart, I used to share mistakes that I'd make”

Q but it's just too interesting for me. You're such a family-oriented Person. And both Sagar and Will said this also. How did having children, do you think, change your operating mindset and change you? It's something that I think about a lot, despite obviously being hopelessly single for the rest of my life. It is still something I think about a lot. How do you think it changed your mindset?

A I love that you asked that question because my wife and my kids are the most important thing in the world to me. And so we have three sons. They are seven, seven, and six. I'm shocked that on this podcast that you have not heard them yet. But I think in terms of how it's changed me, I think it's really helped Me focus on what's important rather than urgent. I read this book called How Will You Measure Your Life by Clay Christensen, and it's just, it's just my favorite book because it helps make sure that you think about this question that's so simple, but I don't think most of us ask it enough. And when I think about how I'll measure my life, the vast majority of the ways that it will matter will be the relationship and impact I have with my family and with my friends and closest people in my life. I think having kids has helped me make sure that I focus on the things that are important rather than the urgent. There's always a reason that you should stay late and work on something, because the impact that you'll make at work will be more visible for that next hour than the impact you'll make at home by the things you do with your kids, and it's more visible and tangible. But over a long period of time, I think it's deeply important to spend that time with my family, and so I think they've helped me a ton Maintaining an even keel. They've helped me a ton on remembering what's im…

AI assessment note: “I think it's really helped Me focus on what's important rather than urgent.”

Q he's coming from me. He said that in a nice way, you're a talent snob. And in terms of acquisition, though, it's the toughest labor market in tech that we've seen. So I'm really interested when you think about the self-reflective question there and actually applying that To acquiring the most competitive of talent. How do you think about determining the very good from actually the best of the best?

A Well, Harry, I'm going to have to talk to Will about the way he said that, but Will truly is one of the most talented people I've ever met. He's also one of my best friends, and so I'm glad you talked to him. I do think it is critically important to seek out the very best when you're building your organization. I think it's important to make sure you're surrounding yourself with people that make you and the team better. Mark Zuckerberg talks about how he only wants to hire people who were the world different that he would work for. And I think that's totally right because you got to find people who elevate your organization. They should be better than you at something. And so you asked about how do you determine the very good from the great? I don't think that's a static thing. I think it's about, are they great for your org? Which to me means do their superpowers compliment your org's weaknesses? And are they somebody that you and the team can learn from? And I think the reason I'm so passionate about this is because this really compounds over time. I think about something my partner, Carl Eschenbach says, and it's so simple, but it's so true, which is A's hire A's and B's hire C's. And so I think it is critically important. And I try very hard to be surrounded by A's all the time.

AI assessment note: “do their superpowers compliment your org's weaknesses? And are they somebody that you and the team can learn from?”

Q but I think you have such a Fascinating purview. Having seen the very best of board operations at Instacart in particular, and then now also again on the other side of the table with Sequoia. And so a couple of different questions, but taking one by one is like, first you've seen the best of the best. How would you advise me on what makes the truly special board member?

A Oh, I love that question. Harry, the first thing is you already are on boards and you are going to be, and I'm sure you are great. I would tell you, I think the way I would articulate the goal for you is you should Seek out to build enough trust from the very beginning with a founder where you are their first call when things are good or when things are bad. And so to me, when I think about how you can do that, I think there's probably three things that come to mind. The first one is I think you got to remember what this means to the founder. You know, one of our values at Instacart was this is your baby. And I think that that is especially true for the founder. I mean, the company is not numbers on a page. It's not the board deck. An analogy that I think would be good for you to think about is this company to the founder is as important as your mom is to you. And I think that that will help you empathize in the right way for the founder. The second thing for me is quality is just so much more important than quantity. One of my partners, Michael Abramson, he often doesn't say a whole lot in a board meeting, but when he does talk, everyone's leaning forward in their seat because each comment is incisive and insightful, and it just gets right to the point. Oh my gosh, we've got to think about that. And I think the last thing is in terms of trust, I think if you remember that the …

AI assessment note: “build enough trust from the very beginning with a founder where you are their first call”

Q last few years, especially kind of as I've kind of been developing invention. I guess my question to you is on the theme of kind of leadership and And strong leadership. There's also insecurity within everyone. How do you think about insecurities in leadership? And what's been some of your lessons through, I guess, the Instacart journey, and then also now seeing it on the other side as a VC?

A Yeah. I mean, Harry, one of the things I respect the most about you is your willingness to talk about those things. I mean, I think that that makes a big difference to people to hear somebody that they view to be successful and someone like you who absolutely has done these amazing things. Talking about things that they're not great at or things that they're insecure about. And so for me, I think it comes down to authenticity. I don't think people expect their leaders to have all the answers, but I do think that they expect their leaders to be honest with them. And I think that is a absolutely reasonable and good expectation. And so when I was an Instacart, I used to share mistakes that I'd make with the company in all hands, because we wanted to have a culture where people would try things. And the best way for me to model that was to tell people sometimes we're lucky. Hey, we messed up on this. At Sequoia, this is not exactly what you asked me, but it is the thing I thought of. At Sequoia, one of our partners late last year shared their three 60 feedback with all of us at a partner meeting and then asked, can you help me get better on these? I mean, I thought that took just incredible strength and it made me gain even more respect for the person. And so I think on these kinds of things, I think people respond to authenticity. I think they crave these real human interactions. …

AI assessment note: “for me, I think it comes down to authenticity. I don't think people expect”

Q my, uh, domain of comfort. When you click Excel on my Mac, it says sign in or register. And so, uh, but anyway, my question to you on that is like, it is part of our role, both as operators and investors. But my question to you is how do you think about what to delegate versus what to own and control? And how do you think about that decision?

A To be clear, I would imagine for the audience here that They need to know Sagar was being deeply sarcastic when he talked about my exceptional Excel modeling skills. So I'm with you, Harry. But I think the mistake I've seen people make is needing to do it all themselves. Maybe at the beginning when it's you and your co-founder, maybe it's possible to do it all. But certainly when you have a hundred people or a thousand people, that approach just does not scale. And I think this ties back to that point about building a team that is better than you and that elevates your org. And my philosophy on this is pretty simple, which is you should hire people who you can actually trust to deliver. I think that as the leader, as your company scales, your job is to set the goal or to set the strategy. Here's what we want to get done. But then you've got to give the team the freedom to execute. And so that to me means that you end up delegating a lot, but you don't delegate the, here's what we got to go get done. Here's the kind of company that we want to be in. Here's the values. But I do think that you delegate a lot of how are we going to go do that?

AI assessment note: “you end up delegating a lot, but you don't delegate the, here's what we got to go get done”

Q he's coming from me. He said that in a nice way, you're a talent snob. And in terms of acquisition, though, it's the toughest labor market in tech that we've seen. So I'm really interested when you think about the self-reflective question there and actually applying that To acquiring the most competitive of talent. How do you think about determining the very good from actually the best of the best?

A Well, Harry, I'm going to have to talk to Will about the way he said that, but Will truly is one of the most talented people I've ever met. He's also one of my best friends, and so I'm glad you talked to him. I do think it is critically important to seek out the very best when you're building your organization. I think it's important to make sure you're surrounding yourself with people that make you and the team better. Mark Zuckerberg talks about how he only wants to hire people who were the world different that he would work for. And I think that's totally right because you got to find people who elevate your organization. They should be better than you at something. And so you asked about how do you determine the very good from the great? I don't think that's a static thing. I think it's about, are they great for your org? Which to me means do their superpowers compliment your org's weaknesses? And are they somebody that you and the team can learn from? And I think the reason I'm so passionate about this is because this really compounds over time. I think about something my partner, Carl Eschenbach says, and it's so simple, but it's so true, which is A's hire A's and B's hire C's. And so I think it is critically important. And I try very hard to be surrounded by A's all the time.

AI assessment note: “do their superpowers compliment your org's weaknesses? And are they somebody that you... can learn from?”

Q and saying, no, I'm sure both of us get many emails asking for time, for calls, for copies, whatever it is. And I say yes to far too many. And I need to Say no to more. This kind of question for me is, what is the right way to say no without losing elegance, grace, and without leaving a bad impression, do you think? How do you do it?

A Well, that's interesting because I think that there's different things, and what I would tell you, Harry, is I actually think it's harder for you to say no to those than it was for a leader to say no to a team member on the goal, and the Not wanting to work on something. I think it's actually a bit easier because you can at least get to, here's what we want to accomplish in the long term. And I believe that the best way to get there is to work on this thing because it's the most important one. And so you can kind of have alignment on a shared goal. I think that the harder part when someone asks you to meet up or have coffee or chat with them is you might not actually have a shared goal, right? And that they want you to do something and you don't have the time. And so in that world, I think that I would tell you that I think it's important that people know that you need to do an excellent job for TwentyVC, and you need to do an excellent job for Stride, and that those are the priorities for you, and so it's not that you can't do it ever, it's that you can't do it right now. And I think that authenticity in the response, I think people will respect that.

AI assessment note: “it's not that you can't do it ever, it's that you can't do it right now”

Q and saying, no, I'm sure both of us get many emails asking for time, for calls, for copies, whatever it is. And I say yes to far too many. And I need to Say no to more. This kind of question for me is, what is the right way to say no without losing elegance, grace, and without leaving a bad impression, do you think? How do you do it?

A Well, that's interesting because I think that there's different things, and what I would tell you, Harry, is I actually think it's harder for you to say no to those than it was for a leader to say no to a team member on the goal, and the Not wanting to work on something. I think it's actually a bit easier because you can at least get to, here's what we want to accomplish in the long term. And I believe that the best way to get there is to work on this thing because it's the most important one. And so you can kind of have alignment on a shared goal. I think that the harder part when someone asks you to meet up or have coffee or chat with them is you might not actually have a shared goal, right? And that they want you to do something and you don't have the time. And so in that world, I think that I would tell you that I think it's important that people know that you need to do an excellent job for TwentyVC, and you need to do an excellent job for Stride, and that those are the priorities for you, and so it's not that you can't do it ever, it's that you can't do it right now. And I think that authenticity in the response, I think people will respect that.

AI assessment note: “it's not that you can't do it ever, it's that you can't do it right now.”

Q a very rare thing to be able to do. What do you think it is that allows you to create that environment? Often, like, I think about, hey, if I kind of show my vulnerability, then the other person will feel safe and available to open up themselves. What do you think you do to create that safe space for the other person to bring themselves truly to the table?

A To the extent that's true, I think it comes from my parents. I've looked at the relationships that they've built and the friendships. That they've built over 50 years now. I love that. I love that some of my parents' friends were like family, and what I observed in my parents was really just this idea of you should be helpful to people. You should try to listen more than you talk. You should be there for them, and you should actually care, and that's why that point that we talked about earlier about trying to remember that a career choice for somebody is really stressful. I do think it's important to remember that it's more important to them than it is to you, and I think that On this point of building real relationships, I think people crave real human, authentic interactions. And I think people want to trust people. And so I think it's really just about being helpful and genuine with them along the way. And I think that the outcomes that come along with that and the relationships that you can build are really ones that really can last a lifetime.

AI assessment note: “what I observed in my parents was really just this idea of you should be helpful”

Q a very rare thing to be able to do. What do you think it is that allows you to create that environment? Often, like, I think about, hey, if I kind of show my vulnerability, then the other person will feel safe and available to open up themselves. What do you think you do to create that safe space for the other person to bring themselves truly to the table?

A To the extent that's true, I think it comes from my parents. I've looked at the relationships that they've built and the friendships. That they've built over 50 years now. I love that. I love that some of my parents' friends were like family, and what I observed in my parents was really just this idea of you should be helpful to people. You should try to listen more than you talk. You should be there for them, and you should actually care, and that's why that point that we talked about earlier about trying to remember that a career choice for somebody is really stressful. I do think it's important to remember that it's more important to them than it is to you, and I think that On this point of building real relationships, I think people crave real human, authentic interactions. And I think people want to trust people. And so I think it's really just about being helpful and genuine with them along the way. And I think that the outcomes that come along with that and the relationships that you can build are really ones that really can last a lifetime.

AI assessment note: “try to listen more than you talk”