How To Invest In: Early Stage Fintech Firms with Clocktower Ventures, Partner Ben Savage

Speaker A: Hello and welcome. I'm Daniel Scribner and this is Outlier Academy, where we study the world's best entrepreneurs and investors to deconstruct what they've mastered and how they got to the top of their game. All to help you win and achieve outsized success at, uh, whatever it is you're pursuing. And today we're going to hear from Ben Savage of Clocktower Ventures. Ben's background is fascinating. From starting his career at Bridgewater to launching the actively managed ETF platform Ardevest, to becoming a partner at Clocktower Ventures in 2013. Ben focused on investing in financial innovation well before fintech investing took off over the last five years. And in this episode we discuss everything from what he learned about giving and accepting feedback as a gift at Bridgewater to why Clocktower focuses on hiring great macro thinkers and and focuses on human capital when making investment decisions, and why they've explicitly never invested in any crypto or defi projects because of the belief that most things benefit from centralization. This episode is filled with narrative violations and non consensus takes and it was one of my all time favorites to record. For the notes, links and transcript for this episode, visit outlieracademy.com and if you enjoyed this episode, please share it with one friend or or leave us a short review on Apple Podcasts. And with that, let's jump into my conversation with Ben Savage of Clocktower Ventures. Ben, welcome to Outlier Academy. I am so excited to have you here.

Speaker B: Thanks for having me, Daniel. I'm really delighted to be here.

Speaker A: I want to start off this conversation by just having you give a quick overview of your background because I find it fascinating you have some experience on the public side, you have some experience on the private side, and that all knits really nicely together at Clocktower Ventures. So let's start with just a quick overview of your background.

Speaker B: Yeah, sure. And I do think most of the time, especially in the investment industry, people tend to pursue these very deeply vertical careers in sort of one discipline and then maybe expand. And really from the very beginning of my career, I've sort of been a broader palette that I was drawing from as an investor. I started off, joined an investment bank at a college called Wasserstein Perella in our merchant banking business at the time, doing both private equity and venture capital transactions and did that really for six years. Started at the height of the dot com bubble in August 1999 and perfect timing, interesting timing. So spent three years in New York and then three years in the Bay Area. I kind of landed in San Francisco In August of 2002, when I was probably the only net migrant into the Bay Area that year or something like that. It was just a wasteland at the true nadir of the dot com bubble. But after six years of that, went to business school at Stanford and then shifted to the public markets, really in business school. Then I joined a small hedge fund in Connecticut called Bridgewater Associates on the back end of Stanford. Because I was drawn, I think, to the idea that to be a really good investor, you wanted to learn as many frameworks as possible for thinking about markets, thinking about the discipline and craft of investing. Bridgewater, obviously a lot of people know about it now. Back then, not many people did, but those who did were sort of very clear. No, no, this is a good place. They know things. So I went to Bridgewater, spent a few years there learning public markets and how to be a bit more of a macro thinker. And then when I left Bridgewater, founded a company that was a fintech startup that I founded in really 2010, 11 time period. And there was an initial business plan that was to focus more on applying some financial technology to public markets that then later pivoted around the time I left into focusing more on private markets. And then when I moved to Los Angeles, I met my current partner, a guy named Steve Drobny, and the two of us sort of started building, along with other partners, the firm today that is Clocktower Group, which spans public and private markets and represented in some ways kind of a closing of a circle. A few years into Clock Tower Group, which really started purely in public markets, liquid markets, we launched Clock Tower Ventures, which was sort of a return for me to venture capital after a decade of doing other things. And, wow, did sort of the industry and the market change in that time period. And so here we are today, and I joke that we get to stick our fingers in lots of pies, which is frankly pretty fun from a, uh, day to day point of view that you get to see and think about lots of different things. As an investor, you have an incredible

Speaker A: purview, given your background and given what Clocktower Group does. And a little bit later in the conversation, I'll have you kind of flesh out that and we'll talk about some of the beliefs that unite the different businesses that Clock Tower Group has together. But I want to talk about one thing in particular in your background for listeners. Uh, I'm always fascinated whenever we have someone from Bridgewater on the show. And one of the things that you said in our prep call Which I loved, is just about Bridgewater's culture and that it's a gift if you let it. And I'd love it if you could expand that, uh, a little bit and talk about your experience there.

Speaker B: I think Bridgewater is a really remarkable organization because it is so profoundly aware of the power of culture on an organization. And to me, there's a tremendous number of great lessons I took away from my time there. But one of the really big ones is that if you're intentional all the time about crafting a, uh, culture, there's lots of different cultures. It's not like one is necessarily superior to another, but if you're very disciplined about saying to yourself as an organization, and in particular if it's modeled really from the very top of the org down, this is the culture that we're aiming for. We're going to talk about it, we're going to teach it, we're going to focus on it, and we're going to filter the people that we bring into the organization for that culture. You can really accomplish great things. It's sort of how you unite people who are generally hard to unite, actually. And what Bridgewater, I think, has done with its culture is, which is now much more visible and conspicuous obviously than it was a decade ago when I was there, is a really core piece of Bridgewater's culture is this idea of being open, honest, transparent and direct with each other, with your co workers and not allowing things to kind of build up inside without expressing it, not allowing someone to talk behind someone's back negatively, although even positively to some extent, and just trying to put out where everyone can see it, what you're thinking about, with the idea that this is a very powerful way, although it's certainly not the only way, to get at kind of ground truth, to get at reality, as I think Bridgewater would describe it or Ray would describe it, and that there's really value in doing that, especially if what ultimately your business is, is like investing. And so one of the core tenants or just practices inside Bridgewater as an organization is the giving of feedback. There's a tremendous amount of feedback that you get. You get it person to person. You get it organizationally like the tools and sort of techniques that exist. And the really remarkable thing about feedback is that it's the only useful way you can improve. If you're not sitting and looking at results, looking at outcomes and looking in particular at how those results were gener and critiquing that process, you can't actually change the results. It's going to either be totally random that causes the change, or it's going to be the same over and over again. But it's very challenging for us as human beings to actually accept critical feedback. You think you want it and, like, everyone's first blood, like, not everyone, but most people have a first pass of, like, yeah, I'd love to get feedback. Of course I want feedback. Of course I want to grow and change and evolve, and I want people to tell me how I can do better. But it's actually not clear, especially when you get it at scale. Like, you get a lot of it and you get it unfiltered. And the hard part, I think, for most of us anyway, although certainly for me, but I think for many other people, is trusting that the feedback is coming from a good place. If someone you love and someone you know loves you, gives you feedback, it's very trenchant because you know that they care about you and they really mean it. And hopefully you understand that they mean it with your best interests at heart. If they're giving you that feedback. So it really. It kind of cuts deep. And it's not necessarily bad. It's just. It's very effective. It's powerful. If a total stranger walks up to you and gives you some feedback, you're very quick to dismiss it because you have no idea of what their motivations are for, why they're giving it to you. And I think the gift of being at Bridgewater is that you're in an organization surrounded by people who provide you with a tremendous amount of feedback. They're all thoughtful, sophisticated people. Like, they're people you should take seriously because it's an organization that filters very highly for who gets in the door. But the gift piece of it is that you have to kind of make that mental leap that they all really have your best interests at heart, that they're your co workers, that it's a shared environment where everyone is trying to make everyone else better. And it's hard to do. It's hard to keep yourself in a headspace where you really believe it, that this person who is telling you you've done a terrible job on something, and it's easy for us to believe it when somebody tells us we've done a good job. Just human nature. It's hard for you to really hear it when someone tells you you've screwed something up. We're all good lawyers in our heads. Our first instinct is to start arguing in our heads about, no, no, no, it wasn't as bad as you think, or that wasn't me, or you're seeing it wrong. But if you can just open yourself up to it and say, I trust that you have my interests at heart and that you're giving me the facts as you see them and you're trying to help me improve, it's really remarkable what that can lead to from a personal growth and an evolution standpoint. And for me there are many. But one of the big takeaways from time inside that culture is that it was a gift to me to get that feedback. And I want to try to reciprocate that and give honest and direct feedback to other people. And it totally informs the way we do business at uh, Clocktower is that we want to be as direct as we can and as transparent as we can with as much compassion and consideration for our counterparties in these discussions as possible. But I think in particular in private market investing, where you're not just sort of sending an order to put on a Microsoft trade, you're like sitting across from real human beings who are working hard and it's a very personal process, venture capital, that there's tremendous value for everybody in that experience to just say, can we get to a place where we acknowledge that we're in the boat together and we trust each other, we have each other's best interests at heart and let's just cut through it and be honest. It's a really powerful place if you can get there, but you have to work hard to do it. And that's all part of, I think, the lesson from Bridgewater.

Speaker A: I, uh, just have one follow up question on that. I imagine you're in that culture. I'm sure at first it's shocking, kind of like you say. Then over time you get used to it. I imagine once you leave, that part never leaves you. And you probably can tell when people give you soft, disingenuous, overly nice, fluffy feedback. So clearly you said that that shaped not only how you interact with your colleagues, but obviously the founders you're talking to. But how has it shaped, I guess the way, I, uh, don't know the way you can call bullshit on someone giving not real feedback.

Speaker B: It's funny, I think part of being an investor in companies, it's a little bit different if like you're trading dollar yen or something like that. Although even then you sort of uh, are trying to figure out whether politicians are full of it or not. But just part of being an investor in companies is your job in some sense is to judge other people, especially as a VC, you sort of VCs all talk about, I want to back the best founders. It's all about the founders. But, okay, so what does that really mean you're doing? You're just judging people and trying to figure out who's going to be good by your lights and who's not. And I think a really important part of that is trying to access this question of honesty. And I think most good venture capitalists that I know have a bit of a bullshit detector in them and that you can just hear in somebody's pitch, do they really believe what they're saying or are they trying to game you? There's a, uh, prominent VC that I know who sometimes talks about authenticity as this variable that really matters. I want to back a founder with a lot of authenticity to the problem they're trying to solve. It's a little bit of like, do they really believe it? Are they really passionate about this? Are they committed to that story? And so I think the way Bridgewater fits into what I would characterize otherwise as like a broad skill set that I think we have to cultivate and other investors have to cultivate, is that once you've experienced anything at extremely high quality and high fidelity, you remember what that's like. Think about like the best ice cream you've ever had. You didn't know how good it was until you tasted. You're like, oh my God, that was, or the pizza, or whatever your food is. That's like the best pizza I've ever had. You now in your head have some like, ideal of what pizza can be. And then you have run of the mill pizza and it's fine, but you're like, you know what? It's not. And, uh, occasionally you might run into some piece of piece, like, this is pizza. And it's kind of the same with this. It's like you've experienced something like a really high fidelity feedback culture. You know what that feels like. And so accordingly, you know what's not that? So it's less that you go the other way of like, this just isn't even pizza. It's generally easy. It's an epistemological thing. The limits of our knowledge are the things we've experienced in many cases and especially in human interactions, you just don't know. And sometimes we talk about this internally at Clock Tower, but also externally with our portfolio companies. Sometimes there are people who have just never really experienced world class colleagues because there are just certain organizations where the culture just isn't great. And even if you had Elite, compelling talent in that culture, they couldn't perform, they weren't unleashed, their capabilities weren't unlocked at the highest level. Once you've experienced that, you know what that's like. You want that all the time, and you design your organization to aim for that. Your standards literally move. But if you've never had that, you don't even know what it's like. So you don't even know what you're looking for. And when we hire people, and I encourage our companies to do this, it's like, find people who know what greatness looks like and know what greatness feels like, and they'll seek that out. And it's a little bit of the same thing here, that if you know what real feedback that's actionable, that's accurate, that's considerate and compassionate, and just quality feels like, then you know what everything else is. And that idea of once you've experienced something of a certain quality, you forever reset your benchmark.

Speaker A: I love that point around quality. It also, I think, makes it clear that giving feedback in that way is really difficult. It takes a lot of you to be able to say it, to be able to articulate it, to figure out what to say. Yeah.

Speaker B: And most people in most things, by the way, have gotten to, like, I know what 80%. They think they've experienced the top quintile of things behind the delivery trucks that keep your life stocked. Thousands of employees at BP go to work every day. People bringing a new offshore production platform online, people making our refineries capable of more like making renewable diesel from agricultural waste, people trading and shipping fuels to our customers, and people helping truckers fill up and get maintenance at our convenient locations. They're part of the more than 300,000 jobs BP supports across the country. Learn more@bp.com investinginamerica but really, you haven't. In almost any facet of human experience, there's some small group of people who've just tried a little bit harder on anything. I mean, it could be anything. It could be building paper airplanes for all I know. And, like, I know how to do that. I've built that. But, like, somebody's just thought that much harder and, like, they're in that top quintile or top decile of quality. And of course, you couldn't experience that in everything you do, but once you touch it, it's like a reference point for almost anything that you're doing and feedback in particular. To your point, we all kind of intuitive, like, well, I know how to give feedback. On how to receive feedback. And the reality is you do, but you also don't at a certain level. And that difference between 80th 90th, 95th, 99th percentile in certain domains probably doesn't matter that much in paper airplanes, but in feedback, it does actually move the needle, I think, for an organization. I think it's a big part of why Bridgewater has been successful.

Speaker A: It's a fascinating way to articulate that. So I want to dive into now, explore a little bit of Clock Tower Group, and then we'll dive deep into Clock Tower Ventures. But on the Clocktower Group side, I mean, I know there are kind of two uniting beliefs that knit all of the businesses that Clock Tower Group has. And that is, one, that everything is macro, and two, that you're intensely focused on human capital. Both of those, I think, are kind of very opinionated, differentiated points of view. Talk a little bit about how you guys got to those, what those three businesses are and how those show up and how you work together.

Speaker B: How we got to them is maybe a good place to start, which is. It's just sort of who we are. All of us are, in some sense, macro thinkers, macro people by nature. And some of that's a function of the career journeys we've been on. I wasn't really a macro person, or at least I didn't know I was until I spent some time at Bridgewater. My partner, Steve, started his career in macro and spent his whole career in macro. My partner Marco, wasn't quite macro and then fairly quickly became someone. It's just like, uh, somehow we all discovered that this is the thing that's exciting and interesting to us. And we've tried anyway, as an organization to filter for people who are similarly sort of of the same mind, where they just like thinking about macro questions, and that's their wiring. And you can to some extent test for it. If you start asking people certain kinds of questions, do they reason by zooming out to bigger and bigger pictures, or do they reason by zooming down into specific anecdotes and personal experiences? Is like a good tactic for it. But we happen to just be a collection of people who like thinking big picture and have come to value and appreciate what that can do for you over time. That it is a distinct way of looking at the world and of looking at markets and investing. But we've come to value it, and that in particular, it informs the types of businesses that we have gone into, all of which lend themselves naturally to macro thinking. And I think it's kind of the same on this idea that what we really want to try to do is be specialists in human capital because it actually fits sort of hand in glove. If you're going to start thinking about macro trends and thematics to make sort of investment bets on and then you go, well, now how am I going to pick within a thematic of the different things? If you started at like fundamentals, and I'm really going to dig super deeply into like Inventure for instance, which product is better, you're going to naturally form sort of bottoms up views on company A versus company B. In our case, we said what we really want to focus on is the people behind it. And it's a very top down way of thinking about companies actually that let's focus on organizational behavior and organizational design. And in particular the human beings that comprise that organization. Like companies are just people at the end of the day. And in particular they're people who make decisions over and over and over again. Like what we describe of as a company is really just a decision making engine. And our job is look, if we can identify decision making engines that sort of slightly better than 50% of the time make slightly better than average decisions, the resources will compound. And so if we give people who we think are slightly better than average at making decisions resources, they will compound faster than average. And that is really almost axiomatically what you're trying to do to make alpha as an investor. And so all the businesses that we've built end up being focused both as macro centric businesses and human capital centric businesses. And so today we really have three things that we do. There's the financial innovation venture capital practice. We have a hedge fund seeding practice which is focused on global macro investing specifically. And then we have a China capital markets practice which focuses on seeding hedge funds in China as well as allocating to hedge funds in China. And all of those are really linked by macro things and human capital things. They're all macro in the sense that China and technology are sort of the two dominating macro thematics of our lifetime. And financial services and macroeconomic thinking are two sides of the same coin. And they're all very human capital centric in that at the end of the day we're giving resources to people running these organizations who then go make decisions along the lines I described earlier. And it turns out that in many respects, although certainly not all selecting hedge fund managers who are going to go run an investment strategy and allocate capital to companies or bonds or trades or whatever it is they're doing is very similar to allocating capital to management teams of startups that have to make capital allocation decisions that lead to the fastest growth possible. Because startups are very specific thing, they're really about building very, very high growth companies as fast as possible. The way the industry has evolved and the capital dynamics work. So really it's about picking the best people to make the best decisions reliably in a macro way. And that in some sense is just kind of what we like doing. It's who we are as human beings.

Speaker A: No, it's fun on the macro side. I mean, one question I wanted to ask there is I'd love your insight on what makes someone a good macro thinker. And part of the reason I want to ask that is I think, at least from my perspective, it feels like when you focus on fundamentals, it seems easy to gut check reality in some sense when you're down in the details. But as you get further and further away, it feels like you're getting further and further abstracted. And I'm just curious, I guess, what are some of the qualities or what are some of the things that make someone a good macro thinker? What does that look like? What does that feel like?

Speaker B: There's not necessarily a checklist. Some of this is you kind of know what it feels like when you see it. And in particular, again back to this idea of what's been your exposure to quality. I think I've been very fortunate to be exposed to some really remarkable macro thinkers in my career. Investors, policymakers, academics. And sometimes it's like anything, you recalibrate your sensitivity from having seen something and you go, I know what that looks like. I might not know how to define it. So there's a little bit of that that kicks in in macro. But I would say there's a couple things that you can think about. One is you have to be someone who's a bit of a conceptual thinker and a bit more of a theorist than a pragmatist. I think, or I shouldn't say more of you have to have this in you. Ideally you actually have both and you have an ability to marry theory and practice. But you can't not have some ability to be a big picture conceptual thinker by nature. And you probably know people who are like this in your life. You ask them a question and they turn it into a bigger question. The answer they give you is a bigger question. And so there's a little bit of that's just how people are. Some of that's hardwired. Some of that is, I think, what did you study in college and how did it shape your thinking and just what have been your life experiences? I think the second thing that in my experience is a hallmark of really great macro thinkers is that they are creative. There are almost always people who end up looking at this very big picture and find original ways to formulate and stitch together ideas. Because the macro palette is so large, there are so many different things you can pull in to how you got to a conclusion. I find sometimes two macro investors might have an identical view on what's going to happen to, like, the currency in Brazil. But they get there in totally different ways. And they both actually can be correct about the causality and the outcome. And that's because the world is a complicated place. It's not that simple. There's a tremendous amount of complexity. And so part of the creativity is being able to identify within that complexity different recipes for getting to the same outcome. But the third thing is actually that really great macro thinkers have a gift for simplification and can cut through it and say, this is what doesn't matter, and then really focus on the handful of things that do to at least their worldview. And some of that is like, do they have an explanatory power that you can just see and feel? And it's a little bit of. There's this. I forget what it is. But real mastery is being able to teach something. The best macro minds, the best conceptual thinkers I know are actually teachers. And when you talk to them, it almost feels like you're being taught every time you sit down with these folks. But then the last thing I would say is, and some of this is just the nature of being an investor. And so I've maybe calibrated this to macro investing is they have to be deeply curious. Deeply curious. Because part of being macro is not taking for granted the way the world works. It's almost like some people just follow the rules by nature. And those people honestly tend not to be great macro thinkers because you have to be willing to go, well, wait, why on earth did that thing happen in the bond market? And wait, the fiscal policy is going that way. And there's this consensus that that means this is going to happen. But that doesn't actually seem like that's likely to hold in this moment or something like that. It's not like you can just sort of study the laws of classical mechanics and like, be a physicist. And although even there, I think the very best physicists are actually Very similar to macro minds. They're very creative people, very curious people, very big picture thinkers. And so there just aren't predictable rules. And part of being good at macro in some respects is challenging. Not even challenging, just asking questions about things that other people don't ask questions about and take for granted. And again, I suspect, you know, people who live like this, there are people you know in your life and they just sort of. You think they're out of their minds half the time that you're like, why are you thinking about that? But that's very much what macro people do. And to some extent, that's what great just entrepreneurs do. I mean, I think there's an overlap between being a great entrepreneur and being a macro person and a macro thinker. Not always, because sometimes there are entrepreneurs that just, man, they dug deep into something and they kept scratching at that edge until they found something to change and then started building back from there. But a lot of times we talk to founders and you really figure out that the impetus for their entrepreneurial vision was a very big picture question.

Speaker A: That's fascinating hearing you talk through that. I mean, the person that keeps coming to my mind is Richard Feynman, someone who's able to have that creativity, have that ability to simplify. And even hearing you go through those qualities, it makes it clear to me why I feel like I know a few of those people more from a distance than people that are close in my life. But when you put that list together, it's very difficult to have all of those things to be able to be truly great at being able to see and imagine, analyze and explain what can be very complicated. It's very loose and it's very wide open.

Speaker B: And I think there's almost as a way, uh, to visualize this is one thing that I think is a good indicator. If you get somebody to kind of paint for you like a hypothetical scenario, it could be an investment, it could be an operating company decision. It could even be a, uh, like, tell me about this trip. You're going to plan to the beach and you get somebody to paint a hypothetical construct for you. And then you start changing constraints and you say, okay, so what if I said, well, on that day of your itinerary, you can't go to the beach. Like, what are you going to do? And you start taking away constraints in a hypothetical construct. You can't do it in something that's too real. Then it's like too easy for people to ground on. But something that's inherently not grounded in Reality is it's explicitly hypothetical and you see how people react to that. That turns out to be an interesting way to assess, I think some of the things you're getting at that well, what did they come up with when you changed the rules? And I found that that can be powerful in helping understand is someone going to share some of these qualities and where are the limits of some of it? That might be a little bit abstract in the way I'm framing it because it's hard without coming up with an example. But in particular, working through changes to the constraints around assumptions turns out to be a good way to identify this. And I think you're right. A lot of people just don't want to think that way. Can't think that way. It's annoying to think that way because it's impractical. Yeah. And it's uncomfortable. It is unusual.

Speaker A: I love that. I love that test. Switching over to the second part, I mean something that I want to spend a little bit of time on is to your point kind of earlier. It's paid a lot of lip Service that obviously VCs are at the end of the day, they're judging talent, they're judging people and using that to inform whether to make a decision or not. I've heard very few people put a flag in the ground and say no, we invest and we focus on human capital. And I love that approach and it makes a ton of sense to me. So I'm curious, what does that look like? How does that shape your investment process? And are there examples of maybe qualities or characteristics that you underweight or overweight? And I'm m asking this almost more about a person than an organization. But feel free to take it anyway. Whatever seems more interesting.

Speaker B: So I would say our investment processing clock to our ventures, which is what I'll anchor it on rather than on our sort of other pieces of the business is calibrated almost from the beginning to try to form as holistic a view as possible of the management teams, the founders that we're engaging with as possible. And everything we do in some sense is structured to try to understand who these people are, how are they going to make decisions. And it's very similar actually to how we just interview people to join the organization. But we spend a lot of time trying to understand in like our very first conversation, why are you doing this? Motivations really matter. Don't tell me about your business. We've read your pitch deck. Why are you doing this? What got you here? And I actually ask it often as Just a very open ended, uh, question. So like, oh, we got connected from so and so, like how do we get here right now to this moment in time? Tell me about everything that comes before this. And it's just like fascinating to hear what people tell you.

Speaker A: That's a wide open question.

Speaker B: It's a super deliberately, very wide open question. And some founders are like thrown by like, well, where should I start? And I'm like, start where you should, I won't bias it. And sometimes you get like, well my parents met and it's like, okay, maybe I don't need quite before you were born, but you really learn a lot about why did people make the choices they made. And sometimes what you also learn is people actually didn't have a lot of intentionality in the life choices and career choices they made that got them to the moment of starting a company. And then it actually almost out of the gate becomes challenging to envision yourself really giving capital to someone on a five or ten year time scale. If you're like, but you just sort of randomly decided to do this or it wasn't. And there's a lot of serendipity in life for sure. But when we talk about human capital, we're trying to really just understand the behavior, the observable behavior in the future and we can't possibly know what that's going to look like. So we're trying to make predictions about it. And we have identified a series of things that in particular we focus on. I think they are all important and we debate all the time internally whether some are more or less less important. I think the real answer is no one's going to be 100% on every variable you'd care about. So a lot of what matters is thinking about the mix and thinking about depending on the nature of the stage that we're looking at, who the other people around the table are, what type of business someone is building. There's a lot of trying to just match, make and think about complementing and offsetting and balancing strengths and weaknesses on teams. When we're looking at teams and then when we're looking at single founders, there probably is one variable that rises a little bit that we spend a great deal of time thinking about, which is, are they an attractor? Can they attract the things they need to be successful? And if you're a solo founder of a startup, what do you have to attract? Well, the most visible one is talent. You can't do it on your own and so you have to be someone that's inspirational operational. You have to be a person that other people want to follow, at least for some period of time. Founders don't necessarily have to carry the company all the way. But this is a hard thing to in some ways talk about because it kind of doesn't feel super comfortable. But we all know people who just are magnets for other people. There's something about that person that makes you want to pay attention to them, maybe makes you care for them, maybe makes you like them, maybe makes you not sure how you feel, but you still want to follow them and figure it out. It's different things in different people. But is someone an attractor of talent? That's a really important question for us. And then similarly, are they an attractor of capital and of resources and of commercial relationships? And it's a slightly different thing that's going to drive that. But I think what we've really come to believe is that gets human capital kind of all the way down. And you want to be backing teams where across that team there is enough of a, uh, magnet function kicking in where they're going to pull other great people into their orbit because that's the only way to actually move the ball forward.

Speaker A: And it's very, very hard to do. I've met a handful of those people, more than a handful, just because I've been in the VC world for a while. But I love that framing of the question, is this person an attractor or is this organization an attractor? And I love too, the way you talked about assessing team, because I feel like what's shown through really clearly, even just talking about the mix and the qualities, and it sounds like you're looking at individuals, their qualities, their characteristics, then how does that all form together in a group? And it embraces all of those qualities of kind of. It feels like the macro approach to making an investment decision with a bias towards human capital.

Speaker B: I think if you view sort of human capital resources as investments in some sense, even within a given company, I think the best leaders, the best organizational builders I've known, are conscious of building a diversified portfolio within their teams. Monocultures don't really work. You need boundaries of, like, this is what is sort of, uh, person for our company, and this is what isn't. And I think, in fact, the very best companies are ones that manage to actually transfer out people that are high performers on the job, but not great culture fits. That's hard to do for organizations, but really great ones figure out how to solve that problem. But within whatever the boundaries of your culture are you need a diversity of perspectives and a diversity of styles and a diversity of strengths and weaknesses. And most great leaders are very explicit about this. In my experience they'll be like, these are the things I'm good at. These, these are the things I'm bad at. Where the people who I'm going to surround myself with can offset those weaknesses for me and allow our organization and allow me to be more successful. And like I found that to be powerful personally. I found that to be powerful for all of our entrepreneurs. Especially as you're thinking about building companies that are durable. It's not a uh, two year trade, it's like a ten year marathon ideally. And you have to hire folks that some of them are going to transition out over time. But to really build great companies you need to be conscious of, I have to make sure that across the sort of C level team and the team below that and the team below that, we're really being honest about the qualities of who these people are and what they can do. And it's not about finding somebody who can fill a role. It's finding a set of attributes that are complementary to the other attributes we have. And it is like a portfolio company construction equation, both inside companies but also for us, like when we're actually trying to back teams.

Speaker A: I love the thought process and the way you guys think through that. I uh, want to transition and talk a little bit about the types of companies you invest in and I am not going to try to rattle off a list of names because you've got a pretty large portfolio of a bunch of really interesting companies. So for anyone that's interested, I encourage you to go and check out Clock Tower Ventures website. But I mean something that was striking to me is you're completely focused on what you term financial services. Some people call Fintech and the firm started eight years ago. And uh, it just, at least in my recollection I feel like Fintech has done really well and gained a lot of prominence over the last five years. To do it eight years ago seems interesting to me and seems remarkable and I know there's a connection between being at artvest and seeing this hole in the market. So can you maybe share a little bit of that story and then just talk about how you guys got to this focus on innovation and financial services services.

Speaker B: The prehistory of Clock Terra Ventures is very much that I tried to raise money for an innovative financial services business in 2010, 11, 12 and it was hard to find people who wanted to talk about that there just was not capital in the system or certainly meaningful capital for financial innovation. At early stages. It was very difficult to find. Couldn't have been more than 15 venture capitalists who were excited about this sort of thing. And we found them all and we talked to them all and we had unfair advantages at the time when we started raising money, we had a very, very prominent Silicon Valley investor who had committed to be a big part of our fundraise before we even started raising because my co founder had worked for him. And today I think in this environment it would be like a, uh, feeding frenzy and in 60 seconds we would have raised money. But it took us like a year to raise Money back in 2011, 12. And I remember just going through that process and thinking, gosh, it's strange to me how little appetite there is for innovation capital in this enormous part of our economy. Financial services is 20 plus percent of GDP and a similar percentage of market capitalization. And some of this is that we were still in kind of the hangover from the global financial crisis. But you could have looked then and frankly today can still look at the amount of capital that is allocated to financial services, broadly speaking, as a sort of sector being underweight relative to others. And so while fintech venture has become a relatively big category, if you looked at private equity leverage buyouts, financial services is still hugely underweight relative to manufacturing or media or consumer durables and things like that. Way more money gets thrown at that. And there's a bunch of historical reasons that financial services, private equity isn't a super big category. And a lot of it has to do with regulation and the balance sheet intensity of those businesses. But it's still in my mind really underweight and a really big opportunity for builders in the investment management world to go and focus on these things. But so when we decided to build Clock Terra Ventures, it was just really in a big way because there was a hole in capital markets. And so we thought that that made it a very attractive place to enter, but also because we could look at it and say, hey, for fundamental reasons associated with changes in technology and some big macro drivers, there's going to be a change here. That hole is going to get filled by capital coming in the door and playing, pointing at financial innovation. And so we really felt there was an opportunity to start getting in front of that when we started talking about this in 2013 14. And I think it's been a faster move than I would have expected in terms of capital inflow to financial innovation. But I also still Think we're in the first five minutes of the game when it comes to the durable secular impact that financial innovation is going to have on the economy to zoom way out.

Speaker A: There's a couple profound kind of points of view that I know that you have around financial services. One, longer term, this idea that there's so much good that comes from financial services innovation, that it's going to save the world and then zooming way, way, way back in time, that it's also, we're just reinventing the same things that have been the same since Mesopotamia. I love both of those equally and I would love it if you could try to knit those together and just share a little bit of your overarching framework for, I guess, how it's evolved over time, or if it's evolved over time and what it's really doing that benefits and impacts society moving forward.

Speaker B: Look, one of the jokes we sort of tell is that there's nothing new under the sun in financial services. People have been buying and selling and borrowing and lending and trading forever, going all the way back to Mesopotamia or ancient Egypt or whatever you want. Like this is just at the bottom of civilization is human beings coming together and exchanging value. Definitionally, wealth is created by the exchange of value. The nature of wealth is that it has to be something that can be exchanged for something else. Otherwise it's not really wealth in the sense that we think of it. Wealth as it relates to other people. That's not to say the only things are of value. There's plenty of things that I value that aren't tradable and aren't interesting to other people. But wealth in its nature is something that is socially connected. And financial services in that sense are sort of foundational to civilization, or at least civilization of strangers. You could have family units and I think arguably even tribal units where they're sort of non monetary in the way they sort of exchange things. But at some level you get to a point where it's like, well, my own sort of economic entity is somehow separate from your economic entity. And the thing between us is an exchange of value and sometimes an exchange of risks, which is also an exchange of value. So classically, in some very deep economic sense, that is what financial services does is it intermediates exchanges of value, exchanges of risk, exchanges of goods, exchanges of services, all in the nature of creating some kind of net benefit from that trade, some sort of surplus. And so financial services as an intermediating function is the thing that in turn drives wealth. I think of it as like infrastructure for GDP, like CapEx for GDP, jet fuel for GDP, whatever it is. And so when we say fintech is going to save the world, what I mean by that is that financial innovation, and in particular what people would call fintech today, is simply a way of taking financial services that have been around for millennia and making them a lot better, a lot faster, a lot cheaper, a lot less friction. I mean, one of the frameworks we talk about is just, hey, what causes slowdowns in financial services? It's just the friction of making things happen. And technology is really good at reducing friction. It disintermediates. That's arguably what all the Internet does, is it just disintermediates middlemen all over the world and industry after industry after industry. And financial services is inherently an intermediating industry. But that doesn't mean it can't get a lot faster and a lot less friction in that intermediation function. And so one of the things I would say as a way of connecting this is like, if you think about property rights and as a thing I can trade, like, it's almost, in some sense, it's a definition of property. It's only really mine if I can sell it in some ways to somebody else. That's like very foundational. What technology has done is it has progressively shrunk down the sort of unit size of things that can be traded efficiently. It's almost like you took your mobile phone and you doubled the pixel count on the screen, you increased the resolution at which you can see things. My favorite example of this is always Airbnb, which is not really a fintech company, but in some sense it is because you always had the third bedroom that you sort of. It was there, it was part of your house, but you couldn't trade it, you couldn't monetize it, you couldn't get liquid on your third bedroom in any way. And then Airbnb comes along and says, well, actually, you can list it on our website. We'll put somebody in there and give you income on your third bedroom. And you could have done this before. You could have put it on Craigslist. And before Craigslist, you could have, uh, called the newspaper and put it in there. But just think about how much more friction that is to just listing it on Airbnb. And now, of course, it's gone even further. And you can list it on Airbnb, but then you can pay somebody else to like, run the process of doing it on Airbnb. And you can optimize with software the Rent, you charge for your third bedroom based on demand. And by the way, not too far from now, you're going to be able to buy, borrow against those earnings from your Airbnb and, like, lower your mortgage rate because it changes your ability to repay your mortgage, and so on and so on and so on. And so in some sense, what Airbnb did from just simple technology is it identified a piece of property that you already had, which was that third bedroom, and allowed you to trade it in some way. This is clearly good. No one thinks this is bad. This is obviously a way of creating wealth, creating benefits for everybody, that these third bedrooms are suddenly more liquid. And I think you can apply that principle super broadly. The whole sharing economy is in some sense this Airbnb. But even people selling their used handbags and sneakers and couture online is part of this. And then Fintech, as most of us think about it, is not really focused on these kind of physical spaces and physical goods, but on more traditional financial services, borrowing and lending and making it so much easier for you to access capital or for you to give capital. That is the bedrock thing that financial services does, is it lets me trade guns today for butter tomorrow, or vice versa. And Fintech just lets you make all those decisions faster, more easily, and execute the share and exchange of value, both in current time, but also over time in ways that are more and more frictionless. And this ends up being really, really powerful for human welfare over the long run.

Speaker A: Even hearing you describe that, obviously a bunch of things are happening. You're reducing friction, you're taking underutilized assets over time and finding new ways to utilize them. And even that example you said of someone renting out a third bedroom, and then they get somebody to hire it, and now there's the mortgage piece to lower your mortgage. And so out of this one little thing comes this massive kind of explosion of value, which just clearly hearing you talk through that, it's clear that it's a massive driver of GDP. And that's why it makes up 25% of GDP today.

Speaker B: That's right. And growing as a share of GDP. And if you were to go apply for a loan, and let's say you're, uh, I don't know, a sneaker head, the bank doesn't have any way of putting a value on the assets that you have in your $50,000 sneaker collection. But if you had those $50,000 in a Vanguard account, totally different. The bank can see it. It's legible to the bank. And part of What I mean by this pixelization thing is, well, actually, in theory, if you had the $50,000 sitting in StockX, you might actually be able to show a bank that statement. Now, I actually don't think the bank would know what to do with it today, but in 10 years they very well might. And the crypto thing would say, well, just tokenize the sneakers and then the bank. But like, that's a whole other conversation. But, like, there's something powerful about technology that I think we haven't fully, as a civilization, as a society yet really cottoned onto, which is that we're actually creating so much more visibility into the basic activities that we all do, that it unlocks all kinds of things that we hadn't quite realized made sense. And some of those have really powerful consequences for human welfare. That person who spent all the money on sneakers, for all we know, they're going to make more money in their sneaker investments than they would have if they bought the S and P. But like, it doesn't feel real to the traditional financial services infrastructure because there was just no way to read it. It was like a foreign language. This sneaker collection.

Speaker A: That's such a good modern example, because I, uh, totally could see a world where in five to 10 years, your StockX portfolio, your portfolio of collectibles, maybe even your portfolio of, I'm not sure about NFTs, but of other crypto assets might actually be there. I want to talk about one more thing on the investing side, and then we're going to switch tax and explore a few more questions just around kind of peak performance and how you approach your work and your life. The last question I want to ask is, it came up when we were talking initially that you guys have intentionally made the decision not to invest in crypto. And I find that interesting for a few reasons. I mean, one, it's the fact that it's intentional and it's something that you were very thoughtful about is interesting to me. But two, you had a really different reason why, and that was that centralization is typically much more effective than decentralization. Can you just flesh out that idea? Because I find that fascinating and it's something. It's an argument that I haven't heard made in the space.

Speaker B: In what remains the most expensive decision I think I've ever made, we at, uh, clocktower, since 2015, when we started, chose to not focus on crypto. There are a whole bunch of reasons for it. Some of them were probably less intellectually good than others. I mean, certainly five years ago, there was a degree of like, was it the message or was it the messengers in crypto that we struggled with? And we would revisit this decision like every six months. And somewhere along the line we formed this view that, look, when you cut through, I think, crypto assets, you get to the underlying insight, which is somehow it's really the word trustless in my mind, that the blockchain leads to kind of an independent, decentralized verification of transactions of these exchanges of value. And in that sense, it's trying to, like, go against everything I just said about financial services. The intermediary is actually not any kind of human at all. It's tech, it's totally decentralized. And the basic idea behind that is that this decentralized trustless architecture is going to be superior over something else. And I think I had a pretty extended argument over the course of a weekend with one of the real pioneers in crypto four years ago, where his argument was like, look, I wouldn't want a financial system where at the end of the day, like, if there's challenges or disputes, it's kind of lawyers who are making these decisions. And I'd much rather be the code, code that's making the decisions, because code is more democratic. Anyone can learn to code and identify the flaws. And that, to him somehow felt very different than like a legal system. And I would say, well, yes and no. You're just sort of swapping one set of high priests for another. On the one hand, it's a very illiberal view of reality, of human nature. In fact, in like, the classic sense of liberalism that like, you have faith in human beings. Crypto is like kind of a short on, like humanity in some ways. It's a good way to put it. It's like, well, I don't trust people to make decisions, so I'll trust these, like robots on a blockchain. But really our view is just much more practical than that. Cleared markets, centrally cleared markets work better than uncleared markets and, uh, lead to better sort of capital allocation decisions at the end of the day and, like, avoid the really unpleasant outcomes that happen in uncleared markets. And I think you can actually look at, notwithstanding even events like the dot com collapse or even the 2007, 08 thing, markets are much more stable today than they've ever been at any point in human history. And it is a function, I think, of central banks. Central banks are a good thing. Clearly the US economy has done better since the Fed was formed than before. And you can look at Almost any macro variable and see this as true. There's virtue in centralization. And I think, you know that even just as a matter of the thing that dominates financial services for most people, which is payments, Visa and MasterCard are incredibly useful. They are centrally cleared payment networks. Now, I think we could argue about, well, is it too expensive, the cost of that central clearing? And it is very expensive. Those guys make a ton of money. And maybe there are ways to drive that cost down and give some of that back to society. Most prices in the United states are probably 2% higher because rich people get credit card rewards and poor people don't. And that feels really unfair, actually. Like, it would be much better if we could just stop that nonsense and the merchants would all lower their prices by 2% to cover the credit card fees. But that is, like, not necessarily a reason to throw out the idea of central clearing. And so we felt for a while that there are probably fairly limited use cases for truly decentralized financial services. And they were largely the first use cases discovered, which is a, uh, store of value independent from government and black market gray market use cases. And those are like the first things that Bitcoin was used for and still dominates, actually, most of it. And then you kind of get the third category, which is now probably taken over, which is just speculation. And that's not necessarily a durable feature of any financial system. It's just a thing. These coins are valuable because people have chosen to hoard them in this current moment as collectibles and because there's a belief that someone will pay more for it. There are very thoughtful folks who are working, I think, on real solves to some of these questions and would say, well, anything that you can do in a cleared financial system, I can do it decentralized. And Uniswap works just as well as a stock exchange does without all the people and without all these weakness moments where humans can get in the loop. And my view has generally been no. Like, I think when things go wrong, most people want there to be a human adjudicator who can, like, fix it. Who can say, no, I get it. You shouldn't have had to pay that airline change fee. I'll waive it for you. In some ways, I actually think about the experience of air travel around crypto. It's like 20 years ago, you could sort of walk up to your gate agent and they had a lot of power in that system to kind of make changes, and today they can't. You have to get through, like, seven layers of managers before you can actually get somebody who can waive the fee, the power has been taken away from those people. And that's actually like, I think, generally a crappier experience for you as a customer of working with the airlines or the phone company or whatever it is. And now you could argue, well, no, no, that's actually more about centralization, where they want to set these rules from the top and then push them down. But I tend to think of it the other way. You've disempowered the people at the edges and pushed all the power to some center. And really that's how, like, crypto works, is that the power all lives on the chain in sort of the center where the code is written. And you've removed any sort of discretion out of the ecosystem. So it's really about discretionary or non discretionary. And like, there's no discretion on Uniswap.

Speaker A: I mean, a good example of that is, I imagine if it weren't all the logic wasn't centrally located, things like someone forgetting a super complicated passphrase and not having access to $200 million wouldn't happen if there was a person you can go to and be like, here's what happened. But that's some of the side effects.

Speaker B: That's right. And that doesn't even get into all the other weird things about crypto that might lead one to sort of not be maximally bullish on it. I think there's a place for it. I think it's not going away at this point, but when I think you really step back from it, most of the time we seem to want some kind of centralized ability to, like, navigate bad outcomes. You want to be able to call customer support and, like, get somebody who can actually do something about it. And that's just not how it works in most decentralized stuff. And so that's a big reason why we've been crypto skeptics.

Speaker A: Thanks for sharing that. I think it's a fascinating alternative take on that space that I haven't heard enough people talk about. I want to switch now and just ask just a few closing questions more around the kind of human side of the equation. Because on this podcast we try to do two things. I think one, help people that are listening have a better understanding of what the world's best entrepreneurs and investors are doing and how they think about the world and how they approach their work. But the other side is just how they function as people, what helps them show up as their best selves. And we've Talked about it a lot. So I don't know if there's anything new that we might be able to mine or get here. But one of the questions I wanted to ask you in particular is I feel like in investing there's just a fascination, maybe overly so, with, like, what gives you your quote, unquote, edge. I think there's so many ways to answer that question. And I feel like the human element, especially knitting in the kind of macro piece and the experience of Bridgewater and all of those pieces, that seems to be one, is that it? Is there another thing you would attribute to your edge when it comes to investors?

Speaker B: For us at Clocktower.

Speaker A: Yeah. Or for you as an individual investor, the decisions that you're making?

Speaker B: Well, I don't know that I have any edge, but I think for us, uh, at Clocktower, where I do think we have edge, part of it is we've designed a strategy as investors that's different. And so without kind of going through the pitch of what we do, I'll, uh, give you a simple example. We've done more than 100 fintech deals. We've invested more than 100 fintech companies, and we've led zero of those. We've never once led a deal. And so most VCs want to lead deals. They tell their limited partners we lead transactions, and then they compete with each other to lead transactions. Because we've never led. We're not competing with anybody who's leading. So there are deals that happen where the founder got seven term sheets from lead investors, and they all said, I'm going to write you a check of size X and I need to own a minimum of N percent of the business. I'm going to take a board seat, blah, blah. And at the end of the day, he picks one of those seven and the other six lose. We show up and we say, no, we're not going to lead, we're not going to take a board seat. We want to own a relatively small percentage of your company and we can win that ability to invest in that deal no matter who wins the lead. We might have a point of view about who we like more and so on and so forth. But. So I think one of the things we try really hard to think about is actually strategy as a way to win and to have some advantage in a marketplace which has nothing to do with like, oh, we're slightly smarter or see things that others don't, or are slightly better looking or whatever than other investors. It's just we're trying to do Something different where there isn't quite as much competition. And so it's a bit of an arbitrage in some sense. But I think for us, that's a big piece of it. And part of that is also we actually describe ourselves as financial services investors first and venture investors second. And I think that's also a bit different. We position ourselves in the market in a way that is intentionally unusual relative to other VCs. And all of that helps from a strategy point of view, I would say. The second thing I think that actually does matter in the market is that we're just people. And we try to, like, really be authentic in our own skin and who we are with founders. Because it's very personal, this business. If you're running a mutual fund and you're buying and selling shares of Microsoft and Bank of America and Nordstrom all day long, it's a different kind of activity than you're sort of going and meeting entrepreneurs who are pouring their lives into building startups. And I sometimes say to founders, I'm like, look, especially our portfolio founders, when they ask our opinion, oh, you know, I'm talking to somebody from this fund and somebody from that fund and some of that fund. Who should I pick? And I say, think about it this way. When you're winning 10 years from now and you're exiting the company that you founded and you've poured your life energy into this, think about which of these people you most want to see around that table when you're having, like a celebratory, such a great question, who do you really want to win with? Who do you really want to be with and make it personal? And, uh, even that is, like, imperfect because in a lot of these places, the people turn over and you're technically doing business with an organization rather than with a person. But if you've picked right, you've picked the sort of person who hopefully has surrounded themselves with people like them. And it all just does come back to the place we started this discussion, Daniel, that, like, it's a human capital thing. And so we just try to be honest in ourselves. And I think to some extent, the founders who we do business with are people who like us, and vice versa. And I mean, with maybe one or two exceptions, like, we really like all of our founders, and I'm joking there, we actually like them all. But, like, they all feel like people that even if we didn't have professional reasons to spend time with, we would by and large be delighted to spend time with them. And again, that's part of the nature of this industry, the venture business. And it's very different if you're going to be, uh, a stock picker, for instance, or you're going to try to trade currency pairs. It's a different kind of dynamic. And so I think some of our advantage, honestly, as ridiculous as it sounds, is that we're just trying to be people like anybody else and find people who want to do business with us. Thankfully, there's enough people out there who kind of like us and like your

Speaker A: track record and not going around. I love that exercise, uh, because I feel like so many people would have phrased that as imagine things are going poorly. Who do you want to have around that table to have that discussion? I love flipping that and focusing on, you're winning, you're exiting this. Who do you want to be celebrating with around that table? It's such a. I think it totally changes the perspective. I want to ask one more question, which is, when it comes to your daily routine, are there things you do daily, and this can be super silly stuff like Inbox zero or this habit that I have, or this routine I do, or this thing I do before I fall asleep that help you show up as your best, best self each day? And are there some of those you can share with us or are some of those you've tried that have failed? Anything there that's interesting, it's worth sharing.

Speaker B: I think I'm like a catalog of failure on personal productivity, to be honest with you. So not really. It's funny. I think there's too much volatility, actually in my showing up and being my best self. It's one of the things that I just personally struggle with. And I said earlier, I think the best leaders I know have tried. The best mentors I have tried to surround themselves with people can offset that. I tried to surround myself with people who can help me offset some of that. And some of that is like, I'm generally not super organized, for instance. And so I need folks around me who can help kind of say, no, you have to be here. I mean, even for coming on your show, there was a lot of, okay, Ben, you gotta be here and put on the headset and do that.

Speaker A: Thank you to whoever that was to

Speaker B: get me in the room. So if anything, I think the hack is just being honest with yourself about where your weaknesses are and asking other people to help you improve. And part of that, again, is back to the conversation we had before, really listening to the feedback when it comes from people around you and um, from your co workers and your colleagues and your spouse and your kids and anybody who's in your life that, hey, that thing you're doing is not working, or that thing you're doing is making me feel a certain way. And I think more than anything, that's what I try to do is, like, give people space to tell me something that's on their mind. And in some sense, I try to then to give myself space to do that too. It's not so much that I'm doing the what's the Saturday Night Live? Skit where he would sit and give himself words in the mirror. Can't remember what that one's called. But I do try to just pause and interrogate myself a little bit to say, why are you so grumpy today, Ben? And, like, really try to name it, whatever it is. Maybe I didn't get enough sleep the night before. Maybe I didn't eat breakfast the right way. Maybe I'm actually anxious about this meeting that I have later today or that podcast I'm gonna go on where I'm gonna get interrogated about my personal habits.

Speaker A: You're welcome.

Speaker B: But, like, being able to just name it and actually for myself say that's what's causing me to behave this way is incredibly releasing. It's just trying to be intentional rather than accidental in the things you do. And I think I found even just articulating it for other people, if I'm in a meeting and I'm not focused, if I'm like, sometimes I'll say, look, I'm not focused right now. Can I just, like, deal with this thing that I need to send this email that's, like, churning in my brain, and then I will be able to be focused on you. People are surprisingly cool with that. I mean, some people are.

Speaker A: I think it's very authentic, as opposed to not communicating that focused looking at your phone. Uh, because then people are really trying to interpret and they have no clue what's going on.

Speaker B: That's right. There's a funny story. Like, a buddy of mine a long time ago was really excited about a girl he'd met. And they met in one city, she lived in another city. And he was trying to figure out, how can I go be there, how can I connect with this person? He was, like, super excited about. So there's a playoff baseball game happening in the city she lived in some weekend. So he emails her and says, hey, I'm thinking of coming down and, uh, going to this ball game. Because, like, it fabricates this Reason would you be interested in going? And she's like, oh, it's so great. I would love to. That'd be great. So he's super excited. He's going to go. He's going to have this weekend. He's not staying with her, but it's going to be, like, a whole thing. So they go. He invests this tremendous amount of time and energy and figuring out every nuance of how it's going to go, and they go to the baseball game, and they have the time of their lives, and then they come away from the baseball game, and somehow she's then, like, oh, hey, let's go, and, like, meet some friends of mine. And she's screwing up all of his plans of how it's gonna turn into this big romantic moment. And then, like, nothing ever comes of it. They go and they meet her friends, and there's a bunch of other people around, and this, that, and the other. And, like, two weeks later, he's, like, distraught, and he finally works up the courage to just call her and be like, what happened? We had this moment. And then I came and I spent this weekend with you. I'm just bummed. And, like, she's like, huh? I thought you just really liked baseball. Because he never just actually put it out there. I'm here because I'm interested in you. And I joke about this all the time that, like, you don't know. You just see the tip of the iceberg, and if you don't ask or if you don't put it out there, what your motivations are like, it's just that things are not gonna go the way you think. I mean, you might get lucky and, like, people intuit what you're trying to do, or the world conspires to, like, give you what you're hoping for, but you have to kind of, like, let people know what's going on in there. Because we're all walking around, like, in our own universes, and if you don't articulate it and tell people, you can't win.

Speaker A: Yeah. And we're all wired differently. And I think some people literally need. The only way their brain works is really explicitly. You have to, like, this is it. It's not an interpretation. You have to put it out there to your point. This has been an incredible conversation. Thank you so much for coming on, Ben. I apologize for interrogating you, although this has been fascinating and I learned a ton. So thank you so much for the time.

Speaker B: Thanks for having me, Dan. It was a lot of fun. I appreciate it.

Speaker A: Thank you so much for listening. To explore other episodes and sign up for our free weekly newsletter. Visit outline and if you haven't already, make sure to subscribe to this podcast. We release a new episode every week on Tuesday. Until next time, keep putting in the work and I'll see you next week right here on Outlier Academy.