Keith Rabois on What It Takes to Be #1 in Venture | The Rise x Nucleus100

In this interview, Keith Rabois discusses how he structures his work as a venture partner, emphasizing rigorous calendar audits to allocate time across portfolio duties, board meetings, recruiting, and deal sourcing. He explains the role of his executive assistant in handling logistics and how he measures quarterly time distribution to align with priorities. Rabois critiques the current venture ecosystem, noting that excessive capital chases a limited pool of truly iconic founders—drawing a baseball analogy to illustrate the scarcity of high‑impact opportunities. He shares a personal fantasy of taking over Apple for a year to help the company navigate AI disruption, highlighting his belief in vertical integration as a competitive advantage. The conversation shifts to the Nucleus 100, a forthcoming benchmark that aims to become the gold standard for tracking investor performance across vintages and categories, and Rabois speculates on who might rank #1 in 2035, acknowledging age‑related network decay and the rise of younger talent. He predicts that the next top VC could be an unknown 20‑something, citing current rising stars like Jack Altman and Delian. Throughout, Rabois reflects on his ability to context‑switch across dozens of portfolio companies, the importance of sourcing, recruiting, and closing deals, and his competitive drive to stay ahead of younger peers. The interview blends practical operational advice with broader industry insights and forward‑looking speculation.
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Welcome to a very special episode of the Rise, celebrating the launch of the nucleus 100. Over the last six months we've reimagined what a modern Midas lift should look like. Built from real data, founder validation and input from dozens of the top gps in the valley to nail the weights and formula that measure what actually matters. The full methodology is live on the site for max transparency. As the top investor of the last decade, Keith Raboy joins us to share how he got there, his advice for those trying to take his place, and how he picks the emerging managers he lp's into. Of course I couldn't resist asking about Opendoor and how he landed Ramp Fair and more. Hope you enjoy. Keith, thank you very much for coming on on my podcast called the Rise.
Pleasure to be with you.
Amazing. I so two main reasons we have you here today. My team has spent the last three months collecting data from founders, fund admins, Pitchbook, Crunchbase, anything public. We scraped X posts, press releases, LPs, LPs, everything possible. Trying to get extremely creative to confirm and validate who did what, deals where. And what we did is we pulled that together and we looked at the last 10 years performance of who are the best early stage investors out there. I think over a dozen posts on X. I have a decent following of partner gps that have given hundred comments on iteration and feedback to the model and the weights. So trying to do it as transparent as possible. You are our number one top performing early stage investor of the last decade.
Sounds great, the methodology sounds perfect. I don't have any questions, honestly, just.
Wanted to celebrate you on that.
Awesome. Well thank you very much, I appreciate it. Obviously I didn't really do much. The founders did all the hard work. I'm sure we'll talk about all of them.
We'll talk about. Well, let's start with Ramp. Just because I'm in New York, right. We're in New York right now. They're the talk of, I think the world to say and definitely tech. When I look at Eric and Ramp, I know that was a wildly competitive deal and you didn't just participate, you let it. My question to you is why do you think Eric and the Ramp team went with Keith or boy to lead that first round?
Well, I think they appreciated first that I immediately groked what they're up to. Literally 30 seconds to a minute into the meeting, they're presenting off Google Notes. They didn't have a dac. I was like oh my God. Boom, boom, boom. Yes, yes, yes, yes, yes, this works. Boom, boom. Rift off. Some of their ideas immediately were in mind meld with both Eric and Kareem. So I think they appreciate that. Obviously, I've had a track record of innovation and financial services, PayPal, Square, a bunch of other ones actually, too. And so, you know, they recognized that I had a lot of expertise in the areas that they were planning to compete in. But I think it was actually we were in strategic alignment from, like, the split second we met and cultural alignment. They really believed in this mantra that Vinod taught me when he was on the border Square, that the team you build is the company you build. And so from day one, they were investing in how do you build a critical density of talent? And they realized, and that resonated with me, that that would be, you know, one area I could be insightful. I love it.
Did you. Did you have a prior relationship with that?
No, I had never met them, literally. My colleague Delian Asperov had met Karim playing a video game. Now, I had been looking for somebody to innovate and build a company in that space and had been trying to pitch people, friends, random founders that they should build something like Ramp. And then Delian was playing video games. He said, oh, my God, I found your founder. And I was, like, a little skeptical, honestly, but I said, well, if you really believe that, bring them in. And so they flew out the next day and literally they set up in this conference room and started presenting because they didn't have a presentation.
Ramp flew out to the Bay.
Yeah, flew out to the Bay Area, put up their notes on the screen, start sharing. And Eric started speaking about the vision. And I was like, oh, my God. I started smiling at Delian. Actually. We've been friends forever, like, probably at that point, like a decade. And so he knew that I was very happy with him. And literally, I was like, as we walked out of the conference room, I'm like, we need to give him a term sheet now. So we offered, like, $3 million within 24 hours, and the rest hopefully is history.
Wow. So that kind of leads into the next question. I think the two lead deals here, Fair Ramp, were like, big winners on our list. We shortlisted these companies before I move on to Fair on the Ramp side, like, in particular, massive presence in New York. Of course, you're now in New York. I'm curious, are you guys doing anything? Like, do you see them? Do you support them in any way.
While you're at it? Yeah. So I joined the board from the very beginning of the seed round. I'm still on the Board, whatever, years later. So, yes, absolutely, we do one on ones. Actually, in their case, it's Cream and Eric together, typically. So Cream and Eric and me. But we, as of today, still only have one other official board member. So we have a company, you know, it's going to do a billion dollars plus next year. We have two board members, external board members. That's it. Partially because the formula is working, the company's working, the culture is working, and most other people could just screw it up. So we're very judicious. We've even investigated what's the minimum number of board members you could have to have an IPO. Long story, but I. I personally think seven is better than five, but you probably pull it off in five.
Interesting.
When you see us announce the fifth board member, I just expect an S1 pretty soon thereafter.
Was there a moment, like you mentioned, that Delian was smiling at you a little bit? You could tell that you really liked the founders. Was there a signal or trigger? Was it a vibe? What was it?
First of all, Eric explained the vision of what they wanted to build and they weren't going to use points. So I have this 20 year crusade against points. I think people use points are usually silly. Secondly, they.
When you say points, what do you mean by points?
Points. Other competitors give you points for spend. It has misaligned incentives. Economics of it don't really work. It's like discounting. There's so many things wrong with points. So I have this allergy for basically my whole career against points. And Eric's like, we're not using points. And I was like, okay, great. All right. I'm already like leaning in. We want to use real cash back. I'm like, great, this sounds amazing. Then they explained what they built at Paribus, which had some leverage, so receipt parsing was going to be part of the original value proposition on expenses. And so Paribis did that. So I was like, great. These founders know how to do one of the core elements, what we're looking for. It was very obvious that they were talking about the team. They wanted to build, the quality of the team. So that resonated with me, with the Vanote expression and adage. So it was just like, as they literally went through the notes, there's even an old obscure podcast that my friend Corey Levy did where he got his hands on those notes from the meeting and he asked me about it and you could see the notes and the quality and. Exactly. They had the roadmap, they had the vision. We've been Executing the vision, actually we've been. The velocity of execution at Ramp is unprecedented. So actually I think we're going to hit most of the vision next year, which almost no one's ever done in less than 10, 10 years. So. But he had the. The breadth of the vision was literally there on day one as well. We are going to be the cfo. The future of the CFO suite. I love it.
I always joke it's now in my pitch when I introduce myself to, to like new people that I really want to work with that Ramp has the cfo. I have the emerging and breakout manager. That's so that's. That's my ICP for.
For Nucleus. That's what I'm building for.
You know, I. The other one that was notable on here was fair before I get to that really quickly. Do you have a different calculus for making determination if you want to lead at Seed versus just participate?
I generally want to lead. So for a lot of reasons I have this metaphor of concrete. And so concrete, when it's in liquid form is very malleable and easy to shape. Once it solidifies, you have to pull a jackhammer out and jackhammers are extremely noisy, painful to use. So the earlier I get involved in a company, I can help shape the foundation. And so the earlier I get involved, the better. And that typically means leading. There are times and exceptions. For example, unfortunately haven't figured out how to track every single startup created across the globe. And once in a while I find out about a startup a little bit too late to lead and they've already committed some money that someone else can invest. So an example of that was Aven, which is a phenomenal financial services company that will definitely propel me on your list next year. And Aven I inter accepted after he'd already had a bit of a handshake deal to take money from Max Levchin. And obviously Max has been a friend of mine for 25 years, so I can't really convince him not to take Max's money. So I could only invest a million dollars and didn't lead the seed round. However, three months later, I did lead the series A.
Let's go.
So I knew I'd found like one of the best founders in the history of the globe. And I was like, oh my God, I only got a million dollars in. How do I lead the next round? And didn't miss on that. And we've collectively kv. Someone at kv, either me or Vinod or Vinod and me has led the.
Next three rounds you mentioned, okay, the era of AI. I feel like we're in this moment of time right now. There are more like new grads starting companies, fresh out of school. I'm curious, just like zooming out a little bit. Like, what is, like what are the effects 5, 10 years from now with instead of like the traditional route of go work at a great company, scale up thing, whatever it is, learn best practices, then go do it yourself. I think that was like way of the past. Now we're just like diving in full speed. What's your take on that period?
I was so by metaphor, I think it's a little bit like football. There's quarterbacks who are drafted in the first round that sit on the bench for a year or two and watch and they occasionally get some, you know, reps. And then there's others who are thrown in to start, you know, day one. And I've studied every NFL quarterback since the modern era. Every quarterback who starts their first year right at school has the worst year of their career. Their completion rate and certainly their touchdown to interception ratio is usually terrible. And then they get better and better and better and they become hall of Fame quarterbacks. I've said literally every hall of Fame quarterback.
Fascinating.
However, the ones who sit on the bench for two or three years by the time they start their first year isn't that distinct or worse or inferior than other years in their career. So there are advantages. Now, can you wait two years in a startup, maybe not so in the football season, maybe you do, maybe you invest in the next 10, 15, 20 years and you wait. But in a startup there may be a time, a window, et cetera. I think there is a movement towards younger founders though. We've definitely noticed this, that there was a window three years ago when everybody was asking what happened to really young founders, because there weren't any companies really being created for about three or four years with super young founders. And now I think you see a lot of the best companies do seem to have, whether they're 19 or 20 or 21 or 22, barely young. And I think anytime you have a rapidly emerging technology that can make some sense. So my friend who's on the board of Ramp, Zack Frankel, who helped start the company, actually has convinced me that the best founders in the AI wave are likely to be younger and they're likely to be more technical than we've seen over the last decade. And there's a lot of logic to.
Why is there more gravity towards first time founders building an AI right now? Than maybe the repeat founder who's been in the arena for a little while with you.
Well, I think the younger founders are growing up like basically AI native everything they do, every part of their life, totally. And they don't have to learn new tricks. And so I think that's important because sometimes the worst thing you can do is try to retrain your brain. Like David Sachs, who is our COO at PayPal back in the day, totally before going on to political fame, used to basically say I'd rather take someone as a blank slate than try to retrain someone's brain. And there's a lot of advantages in a rapidly emerging new technology in just learning things and doing things and then actually truthfully, honestly, they compare with someone like me who's got a lot of experience and I can point out where the grass isn't quite as green as it might look and avoid some unforced errors hopefully so that that concrete doesn't, you know, solidify in the wrong way. But they can take advantage of all the insights they have that, that I would never have.
Totally. I was, I'm not going to say the firm, but I was with an exceptional firm earlier this morning and I made a comment something to the fact of like I, I've worked at some really incredible firms. I think True Search is the best firm on the planet. I think Mercedes at Artico is absolutely like hall of fame Mount Rushmore, a search partner out there. I've worked with great associates. I earlier this summer hired an intern. Reed goes to school in Pittsburgh, not a computer science major and is the first true 10x employee I've ever worked with in my entire life. And it is like a fun thing to watch. He's now with me junior year, full time entrepreneur in residence. Ramp inspired candidly a bunch of experimenting and I think it's like a different breed of this, like next generation. So that's very exciting.
Well, this is why I always counsel entrepreneurs. Once their company gets to moderate skills you want to hire interns, especially technical and design interns because you can get world class talent.
Interesting.
And those people become founders and once they become founders, you're never going to hire them again. So you're one opportunity to tap into the top, you know, 1%, 1 basis point or 10 basis points of talent maybe as an intern.
That's amazing. I don't know if this is an intentional strategy of yours, but I have met 100 plus emerging managers this year. I've definitely seen you on a few lpacs. Right. Is this Something that you like, intentionally seek to back emerging managers. Is it more organic like in network folks that, you know, how do you think about that?
It became. It was organic. Initially. People just reached out who wanted to become emerging managers said, hey, can I tell you about what I'm up to? Do you have any advice, et cetera? And then, by the way, would you invest? And so if I had a strong relationship and really believed in the person, I would typically say, yes, it does have the byproduct of occasionally creating opportunity flow and that's not a bad thing. Now, that said, I want to be the first institutional investor. So I don't love it. When my seed emerging managers send me deals, it means I've missed something. But I still rather invest than or lead the A totally. Which can be a very, you know, lucrative business. Leading A. I'd rather lead seeds than A's, but if I'm going to miss the seed, I definitely want to try to find the series A's that really matter. And so having a strong network of relationships with emerging managers does percolate a lot of opportunities that could be excellent Series A's.
Totally. That's really interesting. I think the. The emerging man I met with an emerging manager last week who I thought was fascinating, they're doing the exact same thing, but with super angels. So they're alping as super angels. Yeah, the first look.
So no, they mean in somewhat. Brian Singerman's strategy with his, you know, announced fund with Lee is something like that on steroids, which, you know, I've told him I think that's a brilliant idea.
I interesting when you, when you do decide to back an lp, let's say they were like lesser known. You didn't work with them super intimately on a deal before. Like, what attributes are you really evaluating with differentiation?
You know, there was one time, now pretty successful emergency manager, ramped in at Abstract, walked in, got introduced to him by Kevin Hart. So it was highly qualified referral. Totally. But when he walked in, I was actually like, how much of your GP do you have left? And I took all of it on the spot. I never met him before in my life.
Incredible.
But his strategy was differentiated at the time. He had a whole deck explaining why there was alpha in his strategy. This is very coherent. You definitely know you're seeing things that other people are missing. I want to have every dollar available. And then Kevin got annoyed because I took all the dollars before Kevin could take some of them.
Is there an emerging manager out there that maybe you're not an lpn, but you're like, oh God, if I can get a little allocation with her or him, that would be incredible.
Well, I was mentioning actually I think Brian Singerman's the most interesting. Brian's definitely not an emerging manage, but I think that approach is very clever and differentiated. So that's what I'm usually thinking is like does this person have a differentiated network that's really hard to scale or do they have an approach to investing that's differentiated? And then I can kind of watch and learn from.
Amazing. I Since you're number one on the Nucleus 100, I think you're a good person to ask these questions too. So I work with a lot of folks who are either at tier one funds today, unhappy thinking about exploring, talking to building this next gen program for Nucleus. Right. A lot of these folks are looking to break into venture coming from the prods and the teal fellowships of the world. So they're already in good company. What's your advice for someone who has no venture experience? No investing experience is clearly a top decile technical talent. New graduation has an itch to break into venture. Should they apply, should they join a startup?
What's the problem? I think they should either join a startup or found a company with almost no exceptions. Like especially if they're technical, you'd ask the question like why are they interested in venture? And usually when I meet people like that, the answers are pretty superficial. Like most people don't even understand what venture really is versus what it looks like on TV sort of thing. So I think it's better for almost everybody to try to build or actually build or watch people building. First of all, it'll make you more confident that you're making the right decision. This is a 20 year job minimum. Secondly, you'll be better suited probably to perform the job. And third, you'll have more credibility which also helps you perform the job. So I think it's, you know, Delian wrote a blog post lessons. He had a series of five lessons he learned from Keith and the first one is about how to become a vc. So I actually recommend that for people who are serious about like the topic versus you know, a quick 30 second, you know, sort of piece of advice for me. But fundamentally I think it's a bad idea for almost anybody right out of school to want to be vc. Doesn't mean you can't be an associate somewhere. You know, spend two years like watching and learning. A is this right for me? Because you'll, you'll see what the industry, how the industry really works. Then use the platform and vantage point of seeing 100 or 200 portfolio companies totally and choose the best company for you to join and the best culture and the best opportunity for you. So it could be an introduction, like an entree job, and then find a company to go build. Then if you really enjoy the experience of working a venture and think it's what you want to do, then doubling or tripling down after you've built something is a very good move. And if you do this right at school, you know, by the time you're 30, you'll be, you have two, maybe two shots at a startup.
I, I think that's amazing advice. The themes that I hear on my end when I'm talking to principal partner types that are reaching out to me or I'm, you know, we're getting connected in some way, shape and form. I want your reaction to. I think the number one theme is, first of all, gravity has shifted to track. It used to be on brand. Two years ago, if you worked at a great fund, if you worked at Khosla, you could go pick an emerging fund or someone a little lower in the pecking order, they would hire you because you were from Khosla, you were trained well, you were under Keith, you were working the node. Now it's all tracked. It doesn't matter if you worked at Khosla, if you didn't do any great deals at Khosla, it's, it's, it's less important that you work at kb. Right. I'm curious your reaction to like this sentiment, Alex. Like, I want to start exploring. I am lacking track because of the fund and the platform that I'm at. And I want to go to a new firm where I can see better deals and get into better deals.
Well, if you're young, that might be a mistake, at least in the second statement. Because part of the art when you're young is to find and identify opportunities like that. When someone wants to work at kb, let's say one of the things we're looking for is can they find and source in quotes, opportunities. So when you're young, you've got to be able to develop that you don't have to win. I think that's a mistake to try to prove you can win, that you can develop over time. You can partner with me, you can partner with the node I mentioned. You know, Delian basically found me Kareem, which led to Eric. Lots of good investments can be found by somebody early in their career that's what you want to prove you can do. So if your excuse is, I'm at this mediocre place but I can't identify opportunities, that's not going to work very well. If you can't win or you can't convince your partners or colleagues to invest, that's a problem that can be solved by changing funds or starting your own fund. But if you're not finding opportunities, that isn't going to get better.
I, I'm really glad you said that because that's what I think in my head every single time is like, okay, I, I actually think there's more synergies between like true tier 1 executive search and like what an associate capacity looks like at an early stage venture fund.
Definitely. I mean, I can help you close an investment that's great. I can even help counsel the founder afterwards so that the company arguably improves its probabilities or amplitude of success. But you know, when I serve on 15 boards or whatever it is, I can't go track every founder across the globe anymore. There was a time in my career when I could because there was less startups. I actually did try to track every startup and like, did I meet them for the seed? Did I meet them before their Series A and I consider it a flaw every time I did it. That is impossible right now. So when you hire young and up and coming talent, one thing they must infallibly do is find, identify opportunities and develop some taste in escalating. Yep, yep.
I think it's a figure it out job and venture.
Yes. Well, I suppose osmosis learning is important. It is important to pair with the right people, whether you can, whether you're paired, you know, with someone like me or someone else in a different firm. But there's one or two years at minimum of osmosis learning that I think is incredibly valuable. After that, I think you hit diminishing marginal returns.
Totally.
And so then maybe you should start your own fund, become an emerging manager, think about other options. But one to three years of immersion is incredibly valuable.
Let me ask you this, this is the second one on the more junior end. We do typically try to stay on the partner GP front if it's an outlier junior role, like if you were hiring a chief of staff, I jump on that. Trent's in the room right now. You're not hiring a team of staff. So we're good. But that's an example of like something that we would take on. Right. I have one of those right now and through line for these junior folks. That were running out.
You found a pretty good one, actually. I.
Who is that?
Well, I mean, at least I don't know if he's your chief of staff or entrepreneur in residence.
Yeah, Reed, that's right. That's right. And Joseph's in the room too. Joseph's gonna. Joseph's the next read. He's coming. He's week two right now, and he's off to an amazing start. But this is so. This is a very real sentiment right now. Excellent associate, excellent junior. But they're at a C fund. They want to do big deals. So they might have the perfect relationship with that founding gp. That founding GP might be beloved by people all across the valley, people like you, that you definitely want to, you know, be in those circles. What is your advice to folks like that? Do they stay and learn? Do they start exploring? What do they do?
It's extremely difficult if you want to lead larger stage rounds just because the price of being wrong is so high. So if we have a junior person and they want to see a seed round, even a series a, you're talking one to $20 million in a fund that's X billion dollars. Totally. So the only thing I can do is give you the license to do that, give you some feedback. But ultimately I don't want someone who's just going to mirror my decision to make. I want to see if you can actually invest. Maybe you can invest better than me.
Totally.
I'm like, for example, Delian pulled the trigger on a couple investments that are turning out pretty good that were certainly not right down the middle for me. Yeah. But the only way you learn that is like, like, like Delian, make some investments. It's a little bit like playing the guitar. You can read a book, totally. But unless you pick up the guitar, unless you start playing it, you can't really tell. However, if you're leading 50 to $500 million deals, it's very hard to get any fund to just say, hey, go, you know, make a couple investments. Because it actually does matter to the returns of the fund, which is a pretty serious challenge. Like, we have to deal with this all the time that the various funds, you know, I've worked at, which is, when do you let someone sort of give them rope on a $100 million check? That is a very complicated management decision.
I could only imagine. What about for the partner that is not feeling like they have a clear path to GP at a strong fund?
There's a simple path to that. Find interesting investment opportunities. Prove that top tier founders Appreciate you in some capacity. Everything else you can envision happening later. If you can't do those things, it's not going to get better. Like I actually think you can assess, typically an early stage investor. Early stage investor, three years into their career, you don't need to see the returns. You can tell whether they can they find things that are interesting. Can they forge a relationship with the founder where the founder will pay attention to them? And if you can't do those things, it doesn't get better. Five years. Five, six, seven. Like Semmel. So Semel's a great early stage seed manager.
Hey, Stack.
Semel Shaw. Yeah. Hey, Stack. So he wrote this blog post probably 10, 15 years ago called something, your portfolio is your career or something. And basically the argument of that, I'll have to find the link for you. But basically the argument is after you've made five investments, that's kind of your trajectory. And there's a lot more truth to that. It doesn't mean you can't find exceptions. I don't need everybody sending me every exception. But fundamentally there's a lot more truth to that interesting than false.
At seed.
Yeah, interesting. So my first five seeds, this is a little crazy.
Did you start off at seed?
Well, as an angel investor.
That's right.
So my first five angel investments, I should just have retired there. Truthfully, it was like YouTube, Palantir, LinkedIn, one other really good one. And I was like, okay. But the point is, I think he marshaled some evidence that that's actually more common. The funny thing is I started my angel career for a totally different reason. Almost no one knows this, why I was trying to look for a new cool job. So I figured out, well, at the time, Silicon Valley had crashed and burned, kind of. So as PayPal, we sold the company to ebay, which is a bunch of NBA bureaucrats. Hell no, I'm not working at this place. So I gotta go find a cool, new interesting opportunity. Well, what's a good way to do that? Because there's usually one cool business role, smart. And once they hire a business role, there's not a lot of great opportunities for someone like me who wants to be the business person. So I was like, okay, well, if I find interesting things, I'll just be an angel investor and I'll watch the company's trajectory. I'll like a get to work with the founders, see if I'd be a good cultural map. Watch, you know, watch the comeback. When do they need a business person? Like, when's the right time? To inject yourself. And that's why I started angel investing. I had no idea that I'd be, you know, proficient at it. It was really to find your career. And then fundamentally what happened though, is I forget. There was one great part that I forgot about though, was I actually wound up joining LinkedIn. I made an angel investment in the seed round, joined LinkedIn when they needed a business person. This is January 1, 2005.
Wow.
And six months later go by and I found YouTube and I'm like, this is the coolest thing ever. I need to invest. And I did. But then Chad really needed someone like me, and I actually parked them in our LinkedIn office in spare so I could kind of track them, what they were up to. And. But the problem was I had just joined LinkedIn six months earlier and I can't, like, really leave my job in six months. Especially I was working for Reid Hoffman, who's a friend of mine. So I was like, that strategy worked perfectly. I had two perfect opportunities. LinkedIn and YouTube show up, but it can't do them both at the same time. Although that was before the days that founders did multiple things. So there was a problem with that strategy. But anyway, I did actually eventually then turn it into, oh, I enjoy angel investing, so I should do more of it. But it wasn't the initial. Oh, Yelp was the other one. So the original goal though was definitely find career professional opportunities for me. Qua me.
It's a tough bar to set for first five.
Well, it's a problem. Well, I was mentioning my first year at KV too. Also, the same thing happened. So in the first 12 months at KV, I led the Series A first institutional round for a firm. Doordash Seed seeded Open door and invested Source co led whatever. The series C for Stripe. That's in the first 12 months. So I was like, maybe I should have taken the rest of the decade off. Yeah, you could have. There's something to though. The fairer point is some people think it's a little bit like vintages and wine. There are years that are just better to be an investor and you can't control that. You don't even maybe know it at the time, but your network is fresh. So when you first joined Venture. This is, I think actually what happened in 2013 when I started Venture. My network is very fresh. So I knew the Stripe guys well. I knew Max really well, you know, et cetera.
Totally.
Tony really well. I've been my intern at PayPal folks. Totally. And so also when I left, when I mentioned my angel. You know, I knew YouTube guys all worked at PayPal, Yelp guys worked at PayPal. So I was like leveraging LinkedIn, leveraging that. Palantir was one step removed. Nathan, that actually co founder Nathan Gettings had actually worked at PayPal. So I was just leveraging the network that was really fresh and transparent, porting that into angel investing or venture. And then your network decays over time. And then you have to reinvent yourself and use other tactics and techniques and strategies. Your network will not be that fresh. So I think your first one or two years actually should be very good. If you have a strong network, then you have to figure out, how do you become successful without a fresh network.
On the network front, pay fair.
So we didn't talk about fair. So fair. Both of the co founders, the CEO and COO currently worked for me at Square.
Interesting.
So fair was a very controversial investment. Actually. Most people did not appreciate fair, especially the seed was this KV or KV in 2015 or so. So almost nobody appreciated. They're like Amazon's killing retail, blah, blah, blah, blah, blah. And people's brains just locked. I would say even internally, many people did not appreciate what Ferro is up to, but they trusted me. They're like, these guys worked for you at Square. If you think they're awesome, of course we should invest in a seed. Totally. So I. But.
And were they people you were tracking or they just reached out to you? Hey, Keith.
No, they reached out. I mean, they worked directly for me. So we played soccer. Like, I hired them to Square from my soccer team. So they were. Yeah, they'd even brainstormed with me. Max had a couple actually really bad ideas that he almost didn't set a fair and I fortunately persuaded him not to do them. One was atrocious. It was like insurance for Latin American drivers.
Nice.
And then the second one, it wasn't as atrocious. It was like using a different drill, like a gold drill for your dental work. That one had IP issues. But anyway, fair was much, much better. Gold is ripping anyway. But that one was very different because the art was both just not getting too obsessed on the idea. In fact, if you go to the fair's office today, there's a quote in the office hanging from me which says, my first quote when they pitch me on Fair versus the other two was, this is not obviously terrible. It's still hanging in their office because it actually had a kernel of a really good idea there. But I knew I was going to invest in them. It's just a question of what are they going to do and could I help steer them into something that hopefully would pay real dividends, which they found. And then after the seed, though, what was interesting was they uncovered this financial services edge to what they were doing. At that point. I was like, this is the greatest thing ever because the founding team had all worked at Square in Cash app. And so I was like, now you're doing something not just in retail, you're doing financial services, which all four of you have a competitive advantage in. Okay, now I want to lead the A. So we co led the A with Kirsten.
Awesome.
Same thing again, only in a few months. So one of the other lessons of being an early stage investor. So ramp led the seed. Four months later, we led the series A. Same thing was true at Fair.
Four months from cta. Yep.
Like it was actually first board. After the first board meeting, it was like, oh my God, like we need to double down. Wow. Fair same thing roughly six months later with the ramp.
Let me just ask you.
I had 30k of GMV.
Holy cow.
Like 30k. Like, you know how small it is in financial services.
Not a whole lot.
One Miami car sometimes has that. Yeah.
Interesting. Okay.
And then the same thing was also true. When you find something really good at seed, I think you do want to double down quickly. So definitely did that ramp and it paid massive dividends. Did that at fair. It was very successful. And then also did that. I was thinking of a third company where same thing happened Seed immediately. Oh, I mentioned Aven. Same thing. So you found the right founders for the right company. Figure out how to invest more money as soon as you can.
Totally.
I lost. Actually, I tried to do that doordash but lost. Partially a mistake on my part and partially how our firm as a whole handled the situation. But in any event, I led the seed, wanted to lead the A Alfred and Sequoia wound up leading it.
I mean, not the worst person to lose to.
No. But in fact, actually it's kind of funny. If I lose, it's is a 10. I've tracked every loss ever and 75% of every. And I know every term sheet I've ever lost. I count them and there's a handful, whatever. But 75% are Sequoia and 75% of those are Talford. But then I have a whole list of ones they've lost to me and usually they do the opposite. Like they were getting frustrated and marking up all my seeds. They had a whole list of all these. They had like six In a row, I think, of seed investments I'd made that Sequoia had marked up and they didn't like that.
Yeah, if there was a way to just invest alongside you all the way, I'm sure a lot of people would do that.
Keith. Yeah, it's a decent strategy. But, you know, Ramp wasn't quite as consensus as you believe. I actually think it was the most difficult, in a certain sense, high conviction investment I made. The reason why was everybody was Brux, Brax, Brux, Brax, Brux, including Peter. It was because I was at Founders Fund when I led the first round at Ramp. Peter invested a million dollars personally in Braxton.
Interesting.
So imagine the conversation. So I was like, peter, we just need to do this.
You were still able to do the.
Deal Well, I was like, we're doing this. This isn't an option. There's things like you need to know when to really say, we're definitely doing this. And this was one of those, we are definitely doing this. I don't really care.
Totally.
But you can imagine the level of conviction. You can't do that every day. You can't do that with your partners every day or every week or every month. You need to really know why. And so I did. I had a very strong thesis why Brexit was going to implode. Turned out to be right second. So that took a lot of conviction. And then secondly, there's not a lot of success historically in funding, in competing with a startup that's already hit escape velocity. It's great to fund a startup that's competing with legacy incumbents that we all make fun of. Financial services. Jpmc. Love to compete with jpmc, you know, whatever. But usually the best angle is not, hey, there's this well funded startup that seems to have some trajectory. We're going to fund the second best. That has generally been a bad strategy. So it had a lot of friction there. But one anecdote. You'll love this. He's going to love this because I'm going to name him. My friend Locky was running his first fund, which was one of his early LPs. You introduced me. I love one of his early LPs, him. And we got him a bit of an allocation in the round and he turned it down because it was too small of an allocation because we wanted 15% ownership. So it was like $3 million. Anyway, Lockheed turned it down and I ran into him that day at Barry's in the Castro and he told me he turned it down. And I just looked at him like a completely Florida like Lockie, this investment will return your fund. Like, go fix that. And he didn't. But later found a way to get to be an investor. But the small allocation we gave him would have easily returned his fund. But I knew at that day at Barry's, I never tell friends like Lockheed, like, this is definitely going to return your fund unless it's definitely going to return their fund. And I knew that day one.
I think that is a big reason why people want to work for you. Honestly, that's like when I talk to partners, they have a short list of firms they would entertain. They also have a Short list of GPS. Like people MPs. Right. Like people that are leading the ship. And you're on a lot of those short.
So here's the problem with that. And I mean it's flattering, obviously it's great. But learning by osmosis, you can't bring an entourage of people to meet with a founder or to a board meeting.
Yeah.
And so the number of people you can work closely with in Venture is very limited compared to a company. You can scale yourself more in a company as an executive and work with more people. And so I found like company building to be much more exciting from a kind of mentoring approach than actually venture Venture. You kind of have to do it sequentially because the founders just don't want you to show up with like three people and you don't want to offend the founders you're working with. It's. You know, I used to. When I first hired a chief of staff, it wasn't that common actually in venture, but noted had one for a long time. But most.
How long though was your first?
2015.
Holy cow. That's like seven years before I started seeing them.
So. Yeah, no, it was like a very intentional hack and actually related to a point we discussed. I'll come back to it. But I had to use a lot of my own personal credibility to bring Delian was the first to bring Delian along to meetings. But I was adamant because I was like, he will not learn what he needs to learn unless he's sitting in the meetings with me. It's not valuable unless I bring him to the best pitches, the best board meetings, the best one on ones. Totally. But at first I actually had to persuade several CEOs. There was only one who generally would kick him out. And that person actually didn't do that well. So maybe it's about. But in any event now it's more common. But I can't have three people. That'd be insane. Every founder would shoot me.
Totally.
So that's part of the problem in working with people. You kind of have to do it sequentially, which I haven't found a solution to.
It makes sense. It makes a lot of sense. Because the founder's gonna wanna work with you too.
Well, they wanna have confidential. I mean, the reality is the founders are right. Like most of what I do is discussing the most complicated, difficult challenges in the company. That's usually extremely confidential. It's about people, it's about strategy, it's about concerns about financing. So you clearly don't want to be exposed to a bunch of random people. So that's why it doesn't work. So if you have a solution to that, that'd be great. I would love to partner with more investors and work with them, but you have to be very selective about how to do this.
Totally, totally. You don't have to share anything here if you're not comfortable sharing. Curious. I think ramp aligning with TPPN people like, you know, Coogan and Doherty, like day zero was not only brilliant, but it was just like it was, you know, it's the right vibe on the right channel at the right time.
So let's talk. Let's talk about why did I lead the series A immediately after there's first board meeting. There was three things in that board meeting that led to this conclusion. One was the partnerships required to ship a ramp card. There's like three or four different moving pieces. You have to negotiate. They had already finished it in X months and I had never seen it done in less than nine months and they had already finished it in three. So I was like, okay, speed of execution, cleverness, all they're a. Secondly, we spent the whole board meeting, other than three slides, reviewing candidates. Talk about the team you build as company build. They literally went through LinkedIn profiles like 10 deep, maybe sometimes more intent deep for every single role that was open. And we reviewed them and talked through like what we liked and what we didn't like and how to clone them or not clone them. Okay, so they were taking the talent density thing extremely serious. I've still never seen any other founder do that, by the way. I was just going to ask you that. And then third is Eric described the value proposition we were going to launch with like the marketing collateral. And it was better than I hoped. And I was like, oh my God, CEO knows marketing. Wow. Okay, we're off to the races.
A pod was. We've been his.
He literally had three slides that described what we're going to launch with. And I was like, oh, wow. This isn't like the high level from the pitch. This is like, here's the concrete. We're going to save you time and money. Boom, boom, boom, boom. I'm like, oh my God. This is actually excellent. You find a CEO knows how to do marketing. He's almost always invest, period. Like, that is the rarest trait. So he could cut through the clutter of Amex and Brax. He had it all nailed on that one side of like, I walked down the elevator with Delian and Delian was like, do you think we should preempt the A? I'm like, yes, call Singerman right now and get his approval. Like, literally. I was like, on the elevator. I'm like, call Brian right now and make sure he's okay with it.
That's amazing.
Same thing was true at Fair. The Delta that was noticeable and stark at Fair was a. We discovered financial services was a core asset for the company and the team had an unfair advantage. Secondly, their speed of execution was off the charts. So from board meeting one to board meeting two, they had identified the root causes of what wasn't working and had already shipped fixes. And then that became a pattern that you could see. First two years, ruthlessly, we'd identify problems at board meetings, dive into the potential causes, and by the next board meeting, they'd always not only use quantitative analysis and other techniques to identify the root causes of the problems, but already shipped solutions and could already report back on whether they were working. And that cycle is incredibly successful for startups. I bet there's always this anomaly that shows up really fast. The Aven anomaly was Saadi, who's the founder and CEO of Aven, which also I had met originally. We'd extended an offer to be chief product officer for Opendoor.
No kidding.
And he turned it down. But when he started a company, he called me up. So it's like again, a kind of a network, extended network kind of relationship. But anyway, the thing that showed up between the seed and A was he had contingency plans for every contingency. And in financial services, that's extremely difficult to do, like multiple partners in case. He basically didn't believe in any single point of failure, which engineers and technical people always build for in financial services. To implement that across your stack with partnerships, it's basically unprecedented. I've never seen anybody pull it off before. I was like, I've literally been doing this for 20 years and no one Pulls it off. I used to manage that PayPal, all our financial services relationships. I did that for a living. I made some pretty good strategic moves and changed some stuff up that saved us a lot of money and lots of things. But even at PayPal, scale as a public company, getting redundancy everywhere was something that my team didn't quite get to. So he did it in the first three months of a startup.
You, you mentioned your team. I want to, I want to hit on just like talent and team building a little bit.
Yep.
So like I will call out, like I, I sit up Nucleus because I do think the venture landscape will look incredibly different in the next three to five years. I am very aligned with emerging and breakout manager. So like I love cosa. I. COSA is like not someone that I'm, I'm working with. But it's because the needs are very different from like a partner in talent perspective. You have someone like Kelly Kennard who is in the hall of fame of search. You don't need me. It's a different thing. But I am curious for the emerging managers that are tuning in, just hearing like how you think about hiring and evaluating talent, I think would be really valuable. You mentioned your team. We have someone like Trent in the room right now. You look at Trent's background on LinkedIn. Went from. Talk about a career arc. Right. Like from entry.
I think you had six promotions in two and a half years.
Like, absolutely remarkable. Right. And like those promotions are earned every single time. Right. So I'm like, I'm just genuinely curious. When you think about the associate scorecard, hypothetical role open right now, associate under you, what does that look like? What do you, what do you. Is it something in particular? Is it a scorecard? Like, what is it?
I don't believe in scorecards and I think this is maybe my bias in funding founders. Every exceptional founder is extraordinary, but they're extraordinary in different ways. I'm looking for that proverbial spike. They are in the top 1 basis points on some dimension. So, you know, one of the founders that I've worked with is the most tenacious person I know. One's like the smartest, you know, etc. And it can be anything. But I'm looking for that like a spike. Like, why do you have an unfair edge? It really comes down to that. Like, the world's hyper competitive venture has too much at all. Everybody knows, you know. I saw a podcast with Roelof recently with Jack Altman. Yep. Another great emerging manager, by the way. So talking about how he did the math, which is Roloff's specialty, of why there's way too much capital chasing very few opportunities. And that's true. So if you're going to win in Venture, you need to have an edge. And the earlier in your career you identify what is your edge, the better you're going to do. So when I meet someone and they want to enroll in Venture, the question is, can I envision some edge somewhere? Now, if they're great, they can communicate the edge to me and I don't have to do the detective work.
Totally.
Sometimes early in their career, actually, I have to pull it out of them of like, what's the edge? And it can be like some. Sometimes it's a personal story. One of my favorite ones ever is one of my close friends, he's a founder, told me this story when he was working at Uber. He was like, one of these launch city people is moving around the globe constantly. So he was in a new market and the team there he wanted to bond with. He didn't really know them that well. They were going to do a triathlon that weekend. So he's like, sure, this is like Wednesday or Thursday. When he finds out about it, it's going to be like Saturday. So he didn't train that other people do, but he didn't own a bike, so what did he do? He used a city bike to ride a triathlon because he didn't want to. He's too frugal to buy a bike. He didn't have time probably to buy one. So no excuses. He's in the no excuses world. So you find these traits and then you sort of extract from them. But unless you have an advantage, it's really difficult to be successful, I think, in any field. So I'm always. Every time I meet somebody, even when I meet people in other fields, like music or sports, I'm always trying to. Or Trump. Actually, I did this with Trump exhaustively. Some of my friends know. For two years I sat down trying to figure out, why is Trump so successful? All the criticism is easy to find. All the flaws are very easy to find. They're comparable to books, publications. Open up X, you'll find critiques all you want. Same is true of most founders. The criticisms and the critiques are easy. It's like, why do you have an unfair advantage and what is that? And how do you triple down on that? And so that's what I'm looking for when I meet a junior person is some unique advantage and then the rest can develop Later.
Interesting.
It's the same thing true for gps by the way. So we didn't talk about what's the reason why I like to compete with people. Totally. And the reason why I occasionally do well is the reality is I want to back founders. I don't really care about anything else. So I'm just in the founder assessment business. So the reason why I want to be the earliest possible investor is there is nothing else for my competitors to look at. I want to see a keynote deck and a team slide. That's all I need to make an investment decision. Typically love it. Who the hell else in venture in a traditional institutional fund wants to write several million dollar check on a team slide for unknown people? That's where my alpha is.
I freaking love it.
So other people have different alphas. Like Vinod for example has lots of alpha but it's technology wave driven. He's a technologist. He sees things other people do not see, myself included. He was publishing articles about the future of AI in 2013. How AI is going to replace all your doctors. He just envisioned any technical breakthrough, what it can be and what it can do. That's not me. Like I shouldn't be competing on that dimension because I'm going to lose to people like him or Mark Andreessen's another technology driven investor who's very good.
Totally. Totally. He's. He's on the list. Mark. Mark made the list. Mark made the list. He's in the top 10 caused to open door. So you made me a fortune the last couple of months, Keith. I knew you just keep holding. I had a sense that you were going to come back. And we are. For what it's worth, we're filming in, in Pompeo's office right now in the studio. So I feel like I have. He was very have to make an open plug right now. But I have this like sense that you were going to come back and like try to save it and I obviously follow you on ax and like I went, you know, I went not huge but like enough where I'm like super pumped right now and getting someone like Kaz who I know for a fact, like I was doing a CEO search. Siri C. Andreessen company My last article, he was shortlisted. It was, it was a search anyone would have taken. They were looking at sitting CEOs and first time CEOs. Right. I know for a fact one of my best friends over at True Search absolutely has him on short list. I know people have been putting excellent opportunities in front of him for at least two years. Like, how? And I know you've said this, I don't want you to regurgitate it. Like, how did you, like, how did you make that happen?
Sure. Well, so it's true. Like, he had turned down like every possible approach. He was like, I'm in my dream job at Shopify. There's nothing better. I don't want to leave. However, I had one little secret. Last February, he'd been texting me that Opendoor was insanely undervalued. And he'd been spending his weekends modeling how to buy it out for fun. For fun. And his wife is getting annoyed that he's spending all his free time modeling buying Opendoor. So when we were trying to find an appropriate CEO because the last CEO was catastrophic. When I started this project trying to find a reasonable CEO, the spark was, oh my God. Actually, Trent reminded me of the spark. Actually, the spark was because I told him the story that Kaz was trying to buy opendor. The spark was, oh my God, he might actually really want to do this. And that's the most important thing for recruiting top tier executives, CEOs is they actually really want to do it. Like, you can't sell them on something they don't really want to do. But he actually really wanted to fix and build Open Door, even in his free time. So I told Paul Diversa, who's very good at executive search, like, and he looked up because he knew that, you know, he approached him about OpenAI and all these other companies, blah, blah. And he's like, he kind of stared at me and I was like, no, no, no, no. Like, trust me. He's been texting me about buying Opendoor for a year. Like, I actually think, like, this is very real. So part of it's understanding what people are interested in, in their motivations, especially at world class talent level.
Paul's absolutely on that Mount Rushmore I was talking about.
Paul's the best. I use Paul, like all the time.
Yep, yep. I, I think there's a couple others out there. I'm actually putting a graphic together right now to highlight the people like other like S tier search firms that I.
Have a ton of research. He does it. He, Paul's relentless. He even tried like a couple months into my first job at KV when I first started kv a couple months in, he like tried to persuade me to leave like three months in, he didn't care.
I mean, it was actually a pretty good role. Respect you well, you were probably the best person for the job. And I would have been everything he could.
They chose this incompetent person.
Yeah. Well, I'm sure they're doing really well.
That person got fired. Don't worry.
Yeah, I was going to say. Okay, so I want to move to culture pace ambition when you're. When you're like one. Actually I skipped one. Is Coastal hiring right now?
Oh, definitely. You are KR Coastal Ventures.
KR Coastal Ventures.
Yeah. If you want to send us anybody like we're definitely hiring all stripes. Like different. Don't have to be an expert. Any domain expertise. Generalized investment experience. Non investment experience. I'd like actually for younger people. I do like angel investment experience. If you have some cool. I think that's better than none. At least you can have a conversation about why did you invest? How did you identify the founder? What resonated with you? I think it's very difficult to even have those kind of preliminary conversations with people who've never written a check.
Does it matter if it like when.
You'Re looking magnitude of the check.
Does it matter? And I want to see where line. Does it matter if the angel deal was done like last month or last year? Are you looking at as a signal of like clear interest in investing any anytime. Just so they can talk through.
Talk through. Like okay, how did you know this founder? Why did they just said take your money? What about the business or the founder, you know, resonated with you? It's just hard to have even that kind of conversation to draw out someone's brain. Yep. If they haven't, you know, at least done some of that and it's a decent proxy for what you do as a venture investor. It's not the same.
Yep.
But it's the closest proxy. So I think we generally speaking for all my partners at KB sir probably are more excited about Kate who's at least had some angel investments, you know, while they've been doing some other role building a company.
Totally. And you are. We're in New York right now. You live here. I know you guys are out in the Bay also. Are you in San Francisco and the.
Peninsula or where Mostly in Melbourne. We prefer candidates truthfully. Want to live in the Bay Area? Yep. That'd be best.
Why is that? Is that just where the AI founders are?
It's a center of gravity for certainly the firm, which is important when you join a new firm, you want to learn from as many people as possible, forge as many relationships within the firm. I work with everybody in the firm. Like I. I'm constantly probably spamming at this point, my AI colleagues with investment opportunities to get their feedback. Yep. Even the healthcare team I'm somewhat spamming with opportunities. Love it. So I think it's really important when you start your career to have the relationships and expertise. So like for example, when I joined KV I had to really reinvent myself as an AI investor. I had never made any AI investments when I joined KB six months in I still had it. Rogo in New York was my first one in July. And the only reason I was able to make that investment confidently was Gabe CEO Central casting for the founders I like to work with. Like I knew as soon as I met him for coffee that definitely wanted to invest but I knew nothing about AI. However I had three colleagues Vinod Sven and John Chu who know a lot about AI. So I was able to get all of their feedback. Is there anything I'm missing? Is there technical Pro Smart? Is their team capable of pulling this off? So I could lean into the investment now 2/3. I think we published the stats recently. 2/3 or maybe 3/4 of my investments over the last two years are now AI. I could not have done that without Vinod Sven and John's partnership.
Incredible. And are you like partner more junior. What are we any.
All of the above. Like we. We have a. We truly have a large fund.
Yep.
And there's so many companies and we. Our mantra. Our strategy at KB is bold, early impactful. So bold we can. The partners can handle that part a lot.
Yep.
Early. We need a team that can spot opportunities before anybody else. And impactful. That's the relationship with the founder and the vision. Is this a positive impact? Would the company be a positive impact society? But impact does KV have significant impact in the trajectory of the company? So we really need colleagues who can do. You can really help with that.
I love it. Again I have KV and like the Andreessen Bucket Founders fund Bucket like exceptional firm not going anywhere period. I will say on KV I think of all like the folks who are a little bit more mature with built out platforms right now. I mentioned Kelly earlier everyone I've met from the KV platform team or in an operating partner capacity like a Bruce Armstrong or like a Peter Buckland absolute S tier humans in like profit like just like the best at the craft.
Yeah you should meet some more. We have a. We now have a growth marketing team. Brit Broman who worked with me at Square and Open Door company and Ryan Scott. So we built that out function to help companies scale customers which is critical. We're spending a Lot of time. My partner Samir has really been investing a lot of his energy and amplifying our operating team. So we're turning, you know, it's always been a competitive asset. We're trying to amplify it. I love it.
I love it. Okay, I have one open question and then like a little rapid fire and get you out of time.
Yeah.
Okay, Amazing. So just like how do you actually structure your week? You're the chair at Open, you help run one of the best firms in the Valley. Right. You mentioned you're on other boards as well. You go to Barry's all the time. And then I reach out cold on X, what, like four or five, six months ago by now. And you give me time for coffee and you spend a whole hour with me geeking out on everything venture. Like how do you do that?
Great question. We track it ruthlessly as the first step.
You do?
Yes. So actually my chief of staff pairs with my EA because we're trying to.
So you have a chief of staff and in the ea?
Yes. The EA deals with logistics, scheduling board meetings, like where's this meeting? Et cetera, and have a lot of meetings. Imagine most venture people have lots of meetings and orchestrating the meetings because there's usually like multiple attendees and all stuff. So. But we try to analyze every quarter very carefully. How do I allocate my time? How much is kp, how much is portfolio and what do I do? Within that portfolio is a one on one time with the CEO. Is it recruiting for the company? Is it attending board meetings? What geo you'll recruit for the company? Oh, absolutely. Like I help sometimes source, sometimes assassin, sometimes close, and sometimes all three, you know, founders use me wherever it can be most helpful. So sometimes they already know who they want to close and it's just like help close. Sometimes they're like, what do you think of the CFO candidate? Or what do you think of these two candidates? And sometimes it's like, do you know anybody who can actually do this? So do all three. So we break that down. We also break down how much time is in pitches, official pitch meetings. Interesting. And then how much is on random things like conferences or media or things like that. And then look at the allocation and say, okay, we want to dial this up. This looks a little too low. Or this looks a little bit off what I'd want it to be. And then let's try to effectuate that next quarter.
Amazing.
So the first thing is measure. It's like a calendar audit standard thing. I've been teaching executives since 2013 and how to operate lecture is just like audit your calendar. What are your real priorities? And then how do you audit to make sure your calendar conforms to your priorities?
I love it. It's so. It's not like a Monday board thing.
Tuesday.
This thing.
It is no how to build it. We are dealing with so many different companies. If I was running one company only, I think that schedule where you concentrate, you know, you don't contact switch is probably better.
Totally.
I happen to context switch pretty well.
Yeah.
So I don't mind it. But I don't think it's possible when you deal with like, you know, 20 external companies.
Context switch here. If you had to click a button to reset venture today, what's like one rule or norm that really bothers you or needs to like go with, like, what would you change about venture today?
Well, you know, the obvious thing is what Roelof mentioned, which is there's too much capital chasing. Yeah. Call it 20 companies a year that actually produce returns. And that's maybe being generous. And so then the question is, how do you fix that? Obviously you don't constrain the capital. It's a free market. We believe in capitalism. So if LPs want to invest in venture, can't really constrain that. So I don't have a solution, unfortunately. But I think first thing is any problem. Being aware of the problem sometimes allows for creativity around solutions. But we're all guilty of participating in that. And I know people say, oh, it's just you don't want competition and blah, blah, blah, blah. But the reality is it's a little bit like Major League Baseball. There's only so many people on the planet that can throw a fastball 90 miles an hour. And we have not learned how to teach people to throw a fastball 90 miles an hour. Unless you start at maybe 88, all the coaching in the world is not going to get you above 90. And if you can't throw 90, your chance of being a major league pitcher is almost zero. And so Major League Baseball just cannot expand without changing the game completely. Ventures a little bit like that, there's only 20 founders a year that probably can build an iconic company. Interesting. And we haven't figured out how to mint more interesting.
I love that metaphor. And I'm going to steal it, to be honest. You just came into open. You came back. I should say, if you could take over one other public company for a.
Year, well, the one I'd want to take over, I definitely don't have the time to do this is Apple. So I was an Apple fanboy all my life when I met Tim Cook for the first time in 2013. First I met him, one on one, I walked in and said, I own every SKU you've ever produced, except for I don't have every color of the ipod. And he actually quizzed me. He's like, do you have this and that? I'm like, duh, yeah, you want me to send it to you tomorrow? So definitely would like to help that fix the future of that company because I think they are struggling with how to adopt in an AI world. It hasn't shown up yet because they are vertically integrated, which is my preferred strategy generally. The ability to compete with them on hardware, batteries, chips, et cetera is very rare. But eventually someone's going to break through that because AI is so powerful that it can disrupt one of the best companies on the planet.
The entire experience of going to an Apple Store for me every time is so amazing that I really hope they figure it out because I genuinely am a little bit worried that there's nothing there.
I do like my era though. By the way. This is a great device. Interesting. The battery drain is a little fast. That is really thin, but it's super thin, super lightweight. It is. It is actually quite delightful. If you feel it, you'll see it, actually. There you go. I thought I made my first Apple commercial.
Pay this guy.
I achieved my career ambition.
We're getting you out on time today as last one. So you're number one on the new Midas. Well, I have to stop saying that you're not because I'm gonna get sued. You're number one on the Nucleus 100.
The best list ever.
Best list ever.
Many people are saying we want.
Everyone's saying this. Everyone keeps telling me this, like we are aiming. And the reason why I've been bugging everyone on, on Twitter on X for the last three months and like chasing founders and chasing admin, chasing all this data and like asking like we're trying to do it right. We're trying to do everything we possibly can to do it right. We're aiming for this to be the new gold standard to tracking investor performance. And we'll have different flavors grow right, like category, vintage, the whole thing. The year is 2035. Keith. You are chilling on the beach or you are hanging out. You're maybe you're probably still on some boards, but you're like enjoying life and you're not doing early stage investing. There's probably not a world that doesn't happen. But let's hypothetical. Who am I sitting down with that's number one on the Nucleus 100.
Well, look, Vinod, you know, Vinod's still doing this, so that sets a pretty high bar for me. And the President of the United States is pretty good at what he does and he's 80, so 2035 might be easy. That said, I do believe strongly that there are some things you get better on a venture and some things that decay. We talked about the network that decays. Peter Fenton's talked a lot about some of the other disadvantages of age which I strongly believe in. However, my goal would be to still be number one in a decade. That's going to be hard, but I have companies that have made lots of really good early stage investments over the last two years that will take a while to grow up before I get credit on your refined perfect gold standard benchmark list. It's going to be three, four, five years before they earn that and so might still try to be competing for that space. Hopefully my favorite sort of vice is EDM music and Tiesto and Armand can still compete with the up and coming DJs. Actually when I spend time with them, the most important thing I'm always asking is like how do you compete with these 21 year old DJs? Because it's very impressive. They're my age and they're still at the top of the game. Like if you ask an up and coming DJ who's still the best in front of a crowd, they'll say Tiesto. And so I always try to find things like ways. So I don't want to give up on what about number two?
No, you're going to stay in it. Number two.
Number two will probably be someone who hasn't entered the business yet because I think the disruption of AI is so important and so fundamental that I think the blinders of being a VC historically will not be friends of people in their current 30s, 40s or 50s. So I'd bet it's an unknown person in their 20s. If you force me to pick someone who's currently doing actually Jack Altman's got a shot 100%. I'd say Delian has a shot. They're both young enough, totally already experienced enough already have networks and insights, but I hope to still be able to beat them. I love it. I still try. I still try to, you know, beat everybody at Barry's who's half my age. So why not? I love it.
I'M gonna add. Since I asked you, I'm gonna add my. I. I agree with that.
Oh, you tell me wholeheartedly. Yeah. Where's the research?
So those are actually. Those are actually, like. Absolutely. So I'm gonna give those. I'm gonna throw Liam Marie. She's doing well from KP up there. I'm gonna throw Hirsch from NFTG up there, who's also, just, like, an incredible human that I absolutely love. And then I'm gonna throw. Basically, I'm throw Lana Goyle up there solo. Absolutely incredible track record. I haven't met anyone who's not wildly impressed with how hard she works and how smart she is. And I've never met her. But those would be, like, my ads also.
I know some of them, and you're right, they all have high potential. The ones I don't know, I need to beat. I hear KB's hiring.
All right. That was my last one. Keith, thank you so much for having.
Pleasure to be with you.
All right. Awesome.
Awesome.
Thank you very much.
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