How I Invest with David Weisburd - E425: What 30,000 Founders Taught Me About AI, Judgment & Top Founders

Episode Date: September 4, 2026

David sits down with Byron Ling of Twelve Below to unpack the judgment required to invest at the earliest stages of technology. After roughly 30,000 founder meetings over the past decade, Byron believes the strongest signals rarely appear on a résumé. He looks for an almost biological drive to win, second-level thinking, exceptional learning velocity, clear communication, authenticity, and a sense of urgency that makes a founder difficult to compete against.

Many investors just focus on pedigree. They focus on, did you go to the right schools? Did you go to the right companies? Did you have the right titles? And we think those can be important, but really focusing on do they have they executed differently in their life? The best founders are inherently very authentic, and you feel that. And this is part of why are they doing this? You actually don't actually have to ask why that many times, because they're going to be such clear articulators of why they're doing this

and why they're probably the only person that would use. Byron, what do you look for in a founder outside of intelligence, pedigree, or early traction? What I'm really looking for is a set of traits that don't show up in a resume, but they're going to make a founder impossible to compete against with. And so things like pedigree all can amplify those traits, but without these traits, we're less likely to get conviction. So we look for an unbelievable chip on their shoulder. It's almost like a biological level drive. you almost want to feel intimidated by the individual and what they're trying to prove to the world. The other thing we really think about, I kind of borrow this from Howard Marks, is really a level second-degree, second-level thinking.

And so are they thinking deeper about the market than just the surface-level size and growth? And what we find is people who have been historians of the markets they're going after, they can talk about how market share has been won or lost over many years. Some of the other ones we think about are incredible storytellers. We think if you're going to go on this journey that's going to look impossible, you have to marshal capital and talent very early. And so how someone communicates the clarity of their thinking really matters. And the last one is both observed but also felt, which is do they have this incredible sense of urgency? Is it almost as if they're getting so much done in 24 hours that they're going to be hard to compete against?

The sum of it all is you never really know the degree of every single trait, but When you spend enough time with someone, that's how we get to conviction. And what you're trying to see is do they have a pattern of just leading with excellence across their life? I want to get to all those traits later on. But second order of thinking, it's an unusual trait. How do you figure out whether someone's able to think about the market? I borrowed this from an essay Howard Marks wrote years ago, which is first level thinking is really sort of, if a stock price drops, everyone assumes you should sell the same. stock where second order thinking forces you to say, well, what do you believe and what do you

believe relative to the market? And so a lot of the focus on these traits is going back to original question, many investors just focus on pedigree. They focus on, did you go to the right schools? Did you go to the right companies? Did you have the right titles? And we think those can be important, but really focusing on do they have they executed differently in their life? And so going back to second level thinking, I want to go deep around what do they know about the market. Have they gone through the history of the market. Many founders will just say it's a big market. I've talked to a couple customers in the space. It's growing. And I think that's okay, but it's probably not excellent. What we find is the excellent entrepreneurs have become obsessed about the market.

Sometimes that's through professional experience. In many cases, it's just from hard work and research. And so the responses that we prefer to hear are, I've earned the right to this insight. I've cold called 600 customers in the last month. And I've earned the right to this insight that no else will have except for me. Reminds me of previous guest, Volger Shunavasson, talks about this IDMAs, this long and winding road that founders get to figuring out what their business is and what their right to win is through just years and years of suffering. One of the sort of clues around that are they very inward focus, meaning are they pursuing

this mission because they're authentically tied to it? And what you find is that if building a company is going to be a series of small decisions and big decisions, do they approach these decisions as a hypothesis? that they want to validate, or are they constantly pursuing the decision based on what they want to see? And I think that's a big difference between founders very early is many of them are willing to say, I actually don't know what the answer will be, but here is how I'm going to test it. And so I think that's kind of when we probe really deep on their thinking. You start to pick away at how deep have they thought about the problem.

And more importantly, how are they going to run experiments over the course of the company? There's a bit of a paradox, and this is going back to my startup days, and I knew that it was time to start a business. If I was so obsessed, I couldn't get out of my head. It's not something that I wanted to do. It's almost like I had to rid this thing from my head. And some of the best companies, if you just ran this kind of hypothesis, I'm a scientist looking to validate A, B, and C.

If A and B was invalidated, you might go on to another business. But if you're just so obsessed, you're going to find, new ways to bring the company forward. It sounds like you had that sort of innate level of drive and connection to the problem. And I think you can explore this pretty quickly because you just go deep with the founder and you kind of push them over the course of several meetings. And sometimes that's in person, sometimes that's in the phone. And so what you're trying to build, I feel like this is the job as early stage investors,

is how do you generate alpha different from the market? One of the things we always try to do is how do you assemble that picture of all these traits? And I think what you're getting at is can you really break down their drive and obsession? And I think the second level thinking component is just one facet of it. But that comes through in the responses. It comes through in the work behind the answer. And how do you fit that obsessive drive with this hypothesis thinking? Drive is somewhat next to, but adjacent to what you're describing.

So drive is, I'm going to prove this to the world. It could be something shaped from a young age that I have to prove to the world. it may not necessarily be tied to the specific problem. But I think being obsessive about the problem and having a hypothesis-driven sort of approach to solving it is another ingredient you have to have. Big picture, I'm going to chew glass to get this done, but I'm also going to do it in a thoughtful way.

And I'm not going to just run into a wall and bang my head against the wall. And I think those are the two dichotomies that you have to have, both like big picture vision and drive, but also the ability to problem solve in the right way. You mentioned one of your factors, a sense of urgency. You have to have the sense of urgency, but also this patience on the outcome and being focused on the long term. How do founders marry those two concepts? You probably felt

this as a founder, but it's your commitment to this 20-year view, but in the minute day by day, you're constantly chewing glass, you're being told no, and you just have to balance those two things. I really think it's one of the things you learn, though, as you're starting to spend time with the founder is how do they approach all their decisions. And I think that's one of the things you're trying to understand is, are they thoughtful behind decisions? Do they make decisions quickly? Do they choose to change course or pivot or whatever the situation is at hand? That's sort of the sum of what you want to figure out very quickly before really leaning in. Guest Nico Benazas, who ran General Catalyst's seat program for close to 15 years,

he called these people freaks, these people that every time he talked to, they had worked so much on a business that they had changed their mind and just made so much progress sometimes within three days of talking to. I love that. We don't use the term freaks, but I do remember that term. I think it's you're trying to find rate of learning. I think it's a felt sense. And one of the beauties of spending time in person over the course of several days is similar

to Niko's point. You can kind of see, did they listen to a comment you made? One of the things I'll try to do early on is it may not be give feedback, but to push on an assumption and then maybe try something where we push their ambition a little bit and say, you thought this company could be here, but like, what if it could be bigger? And a lot of that is a test to see how do they respond to feedback, but also are they generative? Did they process all that information, whether they agreed or not? And do they come back? And you see the difference between the founders who just have this incredible rate of learning. And the reason we care about

is it's a competitive advantage. Someone who's just going to learn more and is going to get done more faster in a day versus someone else is going to be a competitive advantage that's going to be hard to keep up with. You mentioned another term storytelling. It's one of the most overused probably terms right up there with contrarian. What does that really mean? How do you distill that? Storytelling, I agree with you. It's commonly used. I think it's more about building trust, but communicating effectively. And I think one thing we've realized is that some people can develop great storytelling. This comes back to, it's a skill. But one of the nuances is, we're not looking for all these traits at 100%.

Like that would be a checklist model. And I think in early stage investing, it's very hard to have a checklist. I think the best investments actually come when you break your own rules because you're uncertain and you're breaking your own rules relative to the market. But storytelling is, I think you can get a felt sense of someone's arc of becoming a great storyteller through the way they write, the way they communicate, even just interactions in person. How do they greet other people?

observing all these things helps give you a picture of that. So it's not to say everyone we back is an incredible storyteller, but I think we want to see the ingredients of can they write clearly. One of the things I love doing is actually, as we're going deeper with a company, really analyzing their writing and really trying to think about, how did they choose the words in this response? How did they think about the response? When did they write the response?

It's almost like you're trying to be multimodal. You're like trying to collect all these data points from phone calls, from Zooms, from in-persons, from a meal, and then synthesizing that all together and saying, okay, how do we think this individual is going to be over the course of 10 or 15 years? How much of this needs to be in person? Three-dimensional needs to be experienced three-dimensionally versus behind a Zoom background. I definitely prefer in person. After COVID, Zoom has come to offer in place the first meeting.

It is more efficient in some ways. But I think the best founders and investors want to meet in person. Everything in person is way better, especially because you're going to be able to. especially because you're going to go on these journeys for 10 to 20 years. If you think about it, you may want to put the effort in to get a great partner, and that goes for both ways. So I think in person is far superior. I also think it's how your job is not just to analyze, but to also build trust both ways.

And so I think if you're trying to have what feels like more of a conversation as opposed to a pitch meeting, in person is you can't beat it. And also, the other thing you care about is can the individual generate energy? Like, that is something on a Zoom screen, you can get a phone. you can get a felt sense for, but it's no comparison to someone walking up and saying, hold on, we're going to whiteboard together, right? You just can't get that. And so I just think you get so much more surface area around the individual. You look at somebody's writing, not just their writing, their substack, but their emails, their cadence. What are some things

that you're looking for there? I'm looking for the clarity of thought. And what you're trying to find is, oftentimes we're investing really early when there's very little of the company around and maybe the market's very unknown. And so I'm trying to see, do they have clear thinking about what they want to do? They have clarity around how they're going to approach solving questions. We don't expect them to have all the answers. I have gravitated towards founders where they're extremely clear thinkers, often from a young age. And when faced with a bunch of questions, including many that are unknown, they're able to write in a really coherent way that is both convincing but also humble.

And I think that's what we're looking for. We're not looking for a specific answer because I suspect you're going to learn along the way as opposed to knowing all the answers. It's like taking a position but also be open to changing that position. I actually really love it when they truly just say I actually don't know. And there's two things that can happen. They'll say, I'm actually going to go figure that out. I want to come back to you in five hours and tell you. But I would say the more common thing is it's okay if they don't know.

I want to hear how they're going to approach the problem. They will inevitably face all these product and customer problems that they have to solve. And so much of what we're trying to do at the earliest stages is to say, how good of a problem solver are you? And I think communication is a big part of that. One of the things that's coming up over and over between the GP and LP layer is this authenticity and vulnerability and really getting to know you because LPs are going to be invested in you for at least 10 years. Here you could argue it's similar timeline. Is that also a great leading indicator when a founder is just very authentic with why they're doing something? something even if not every part of the story may be the most flattering thing about themselves?

Yeah. One of the things you want to do is get the founder to trust you. And I think a lot of that comes down to how do you conduct the first meeting in a way where it's not putting them on the stand. It's actually, why don't we just go have a conversation and can we find the truth together around what you're doing? The best founders are inherently very authentic and you feel that. And this is part of why are they doing this. You actually don't actually have to ask why that many times because they're going to be such clear articulators of why they're doing this and why they're probably the only person in the world that would do this otherwise. When you go on these journeys, you're going to be with them. I think about the cap table is like a living room. It's like people

move in. They rarely move out. And I use that expression oftentimes with founders that we're starting to go deeper with because we want them to feel like they can learn about us. And it's not a one-way road. It's a two-way partnership. Getting to authenticity quickly and then figuring out, do you work well together? It's very hard if people are trying to put a facade on and just trying to raise money. What we find is you want to get to the authentic purpose really quickly. Everyone I talked to on the show is chasing the same thing,

an edge. And more and more, the edge comes down to your information, not just having it, but being able to trust it when the stakes are highest. AI is doing more of the information gathering for you every day, and most tools are very good at sounding right. The summary reads clean, but can you trace it back to the filing, the transcript, the specific path, that drove the answer, or are you just trusting the confidence of the output?

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We've probably met about 30,000 founders so far in the last 10 or 12 years, just having been focused on precedence seed, so it's a very high volume. It's an evolving muscle. It's sort of like you're just trying to get better at it every single day. One of the challenges is you make these commitments with these founders very early, but it can take seven to 15 years, sometimes pretty quickly if it's not working. And so you're constantly trying to pattern match things in the past while also making that new investments that are going to take another five to 10 years.

Just having a base of thousands of meetings, starting to see the difference between excellent and good, gives you this foundation for some of these traits to assess very quickly. I still think you need to spend a lot of time with founders. There's no substitute. I don't think there's any shortcut to sort of coming up with this judgment. Certainly not at the CEDRA. The beauty of CED is it's, sort of there's low persistence. It's incredibly hard to predict. You see this in the data with the

funds that there's actually very low market share of funds that consistently lead at these rounds and the companies that become great. And so I think of C does. There's a lot of things we can talk about around the role of AI and sourcing, but there's no real substitute. It's a ground game. You've got to hustle. You've got to be outward focused. In our model, we really like, we have a sense of the people we want to meet. When you have clarity going back to your question, And you can then start to target your sourcing efforts around those individuals. But CED is about being prepared, being ready when the next amazing company walks through the door, but you don't know it. And you've got to be ready when that happens.

To quote Peter Thiel, the next Google will look nothing like the last Google, next Facebook will look nothing like the next Facebook. You really have to keep this beginner's mind. That's why we focus on it's like competency and capability. At the beginning, there's a lot of folks, I think, who just look at pedigree. they'll say, did you go to Stanford? Did you work at this well-known company? And I think if you look at the history, going back to Peter Thiel's quote, many of the best companies did not start that way.

Many of them were actually fairly non-consensus, misunderstood, nearly died along the way. That doesn't mean every single company would be that way, but I feel like that's a part of history that I try to internalize, especially at the earliest stages. There seems to have been this hard reversion from five years, years ago was all about the 40-year-old third, fourth-time founder. And today, it's almost becoming this race for how young the next founder is. I think there's a TL Fellow. That's 15. That's the youngest I've heard so far. In the age of AI, where do you stand on that?

One of the reasons I like focusing on traits is it doesn't bound your market size. You're right. There's been a huge wave of interest in these really young, quote, AI-native individuals who are founders. And there are some amazing companies built like that. But I feel like that takes a very narrow view of the world because you're going through this enormous technology shift. And if you focus on traits, you can say, well, why don't we have a wide market around what might make a great founder? And if they happen to be younger, great. But if they happen to not be young, that's totally fine. What we have found is that in some, one of the benefits of AI is it's sort of collapsing the experience gap in some industries.

And so we have had a lot of success with really young AI native teams going into market. where they didn't know a single person in that market. And one of the insights we've seen is that the sort of rate of product development kind of makes up for the lack of a Rolodex, the lack of any gray hair. It's absolutely a profile we believe in. We have a specific founder architect we call for it. But again, I think that lens of saying, well, you graduate from these schools, you have a degree in computer science and you were in these specific clubs, let's invest.

I feel like that's sort of simplistic thing. Going back to the Howard Mark's thing, I think that's sort of first level thinking. The other part of that is the whole market can do that as well. So you should ask yourself, why are you going to have superior returns when the other 50 funds are doing the same thing as you? What else have you learned from Howard Marks? The most popular essay was the whole non-consensus and right framework that I think many investors like Bill Gurley have popularized.

But this first and second level thinking, I can just apply to all areas. We've been talking about it in the sense of founders, but the other area I think about it a lot is in market quality. Another general thing that many investors in this age have been thinking about is just overall revenue growth. People will say, oh, it grew from zero to 10 to 100. And I think one of the things, that might be a really impressive company for the record, but one of the things I try to probably that thinking to is like, do all markets grow at the same rate? If it's an attractive market, what is the right adoption rate for this market, even in the world of AI?

A lot of Howard's writing over the years just really pushes on this point of how are you thinking different from the market. And that's one of the things I really admire about investors and other asset classes because the one, I don't know if it's a downside of the private markets, is everything is marked in a way that's not daily. And so you're not really faced with the weighing machine of the daily market mark. And I think that's one of the things when you're a public investor or a credit investor, you sort of face those results daily and weekly. Getting a quicker feedback cycle. Yeah, exactly. the whole idea of being non-consensus is right is much more challenging than it sounds and that's because your competitors in the venture game are a 99.9% kind of intelligence

in terms of society so that bar for even average is so high so that Peter Thiel question which is what do you believe that nobody else believes if you're in that kind of industry becomes that much harder to be non-consensus and right? It requires you, there's this chart floating around where it kind of shows all the companies everyone talks about today. I think many of you will underwrite new investments because they look at a company like SpaceX or the foundation labs. But I actually think the Howard Marks framework would say, well, what was the shape of those companies when they were just getting started? What was the shape of the environment and the market when they were getting started and using that as a framework to say maybe that's the way to think about the next new market? That's at least how I like to look at the world, and we use, given the stage we invests,

the traits are a really good proxy because you're building a portfolio and the one constant, assuming the market stays the same, is the founder's traits. And so that's why we focus on that. How much does the industry play into the founder attributes and the companies you're looking about? There's this notion of founder market fit in some areas that really matters if it's a really capital-intensive business, if there's a high degree of something. scientific or technology risk that there's a specific background that's required. In those cases, generally speaking, you want people from that background, or you could be

convinced by someone who has no experience, and sometimes that's a competitive advantage. If they're a learning machine and they're going to figure out how to build something in a space they've never done before, that could also be a competitive advantage. But for the most part, we care more about after getting conviction on the founder and their traits, what specifically about the market is really compelling and what is the why now? So we think in addition to a great founder, there has to be some catalyst in the world. In this case, there's a lot of in the AI space, there's a lot of technology catalyst that's opening up a change.

But we also care about what's the market going to look like in 10 years and where has value been captured in the last 10 or 20 years and where is the opening for a new 10-person team to come in and take a bunch of market share. We care just as much about it. I want to get into how AI has changed venture capital in a bit, but maybe tell me a little bit about your background. How did you get in this seat? I worked in finance briefly, but entered the startup world, and I was lucky to start in

New York City working with a great founder here named Kevin Ryan. He had been the CEO of Doubleclay, co-founded Guild Group and Mongo, and I had worked with a company called Guild Group. And it was through that experience in the mobile era, seeing the beginning of the iOS store that I got really interested in early stage investing. And so after business school, I joined what was the first time fund called Primary Venture Partners at the time. It was a brand new firm. Nobody had heard of us. There was an amazing experience working with Ben and Brad. And not just learning how to become an investor, but also building a firm from scratch. Nobody

invited primary to the seed stage party in New York City. I then transitioned to a bigger firm called Canaan, where I was a partner and general partner. It's a multi-stage firm, about a billion dollar fund, still based in New York, investing across the U.S. and Europe. And a couple years ago, my partner today, Taylor and I met 12 years ago when we got into venture. He was at a competing firm, but we worked on a number of investments together. And we had the beginning of this style of investing of just being really early, having specific traits that we looked for, and then having a partnership model where we would just work really close with these founders all the way through product market pit.

And so we came together a couple years ago to start 12 below, which is an early stage focus firm based in New York. Has things gone harder or easier in the last couple of years? Overall, it's a very interesting time in the sense that the amount of capital that has come in has never been greater,

but the amount of concentration has also never been higher. So I think we're at our stage in the business of net new, great founder starting companies. As long as that is happening consistently, we're thrilled. Some of the nuances that have gotten

and harder for founders is much of the capital has gone later stage and it's concentrated in called the labs, some of the SpaceX and a couple other companies. And so on the whole, it's a dizzying period. It's what makes it really fun to be honest as an investor. Like you want to feel the mental jizzitsu of how to navigate these environments. But for founders, it has been harder. Unless you're a set number of companies where capital has come really cheap, there's a lot of founders at all stages that I've had a hard time because of the concentration of capital. But I think the flip side is the optimistic side is if you have a great market and you are the beginning to be the market leader, one thing you saw in the 2000,

kind of 18 to 20 era was you would have 10 competitors funded at the same time. So I actually think even though it's hard, what you're probably going to see in the next couple of years is the companies that have just had conviction, they've had market leadership, there were real customers and real venture scale markets. You may actually see an acceleration of those companies, even if there was a period where funding was challenging. Maybe because funding was challenging. It goes back to what we were talking about in the beginning, which is figuring out people that really have founder product fit, that have a chip on their shoulder that really focused on solving this problem. How do you figure that out?

Well, you do it in a space where there's not a bunch of funding. Going back to your question, one of the other elements that's been hard in the last year is the pace of the model changes. So just on this point of funding, there was a period where there's some Apple, applications in AI getting funded, and then there's been a fear that the labs will do everything, right? So if you're a founder and you're making this 10-year commitment and you started two or three years ago, the volatility of who's going to win and how can you win as these new foundation model scale has made it hard. But to your point, the flip side, the people who have, it goes back to the fundamentals, they have a clear view of what they want to do. They've got an end market that is in transition. and if they win, there's a really big venture scale prize,

you just got to solve through it. And on the other side, when you wake up and you're of scale, you may have a lot fewer competitors, and that's going to feel really good. Yeah, people said that, or an investor in Lagora, people said that the large language models are going to disrupt the legal space and it's publicly disclosed.

They're growing just like wildfire. One of the frameworks I use is if you're thinking about that threat, it's like go talk to a bunch of customers in the end market and ask them, do they even know the names of the different models? Do they even know what Codex is? Do they even know what Himmy or Sonnet or Opus? And you'd be shocked. There's a couple trillion dollars of the economy beyond just AI infrastructure where many

of those customers don't know and they frankly don't care. And I think that's kind of how I think about it. It's so easy to be myopic, me and my business partner. We once looked up, not how many people know who Scott Besson is, but how many people know that there's such a thing as a Treasury Secretary in the U.S. And there's something like less than 10 percent even knew that. was a position, let alone who fulfilled that position. So it's so easy to be myopic.

That's when you're in it day to day, you can feel like this is going to be done soon, right? And it's kind of that adage of people overestimate what's going to get done in a short period, and they underestimate what can get done over the long run. You could track AI adoption by sector. And like today, it's very low. Maybe developers it's really high.

But there's so many parts of the economy where it's barely 1%. Having that balancing act against the volatility of the pace of investment is really important. Lucas Swisher from GoTo talked about these different S-curves. So first you had the consumer adoption, which most people have tried chatGBT, and that's the chat GPT moment. Then you have the developer adoption, but most businesses have not actually seriously integrated AI. Then that's why you've seen a lot of the investment go on the enterprise side, because depending on the industry, the amount of there's just so much work still to diffuse

AI into their businesses for them to actually get returns. So yeah, we're still early. There are some categories where you mentioned legal where there's been a lot of investment and there's been a lot of companies. But when you step back in some of these end markets and realize how big they are, even if there's a couple early winners, having a view, is it going to be one company to rule the entire industry? These are some questions to think through when you're thinking about doing more investments

in a certain category. Yeah, it's that's second order of thinking. Yeah. What makes it really fun is you're kind of dealing with this new form of magic intelligence, and that's going to create more volatility, too. Like, what are the language models like in a year or two? Does that impact when we look back in 10 or 15 years, when we look back at the products built in year two compared to year five and say, oh, of course, we should have thought about that. It's volatile. It makes it challenging, but I think that's what makes it fun. Sitting right where you're sitting a couple weeks ago is Michael Gilroy from Marathon Venture Partners, $400 million. mostly Series A fund. You're saying one of the challenging things in venture capital today is that so many people could vibe code startups that you'll have the 1020 startups that look almost indifferentiable. Are you seeing that seed around?

Yeah, I mean, the cost of developing software, the cost of getting up and going, that's been a real advantage for the companies we fund because when you're trying to figure out product market fit, you're just trying to get iterations to the customer. You're trying to find this breakthrough around this deep unmet need. but I think that doesn't change the quality of the authenticity, like the connection to the purpose. He's absolutely right in that there's been a way for sure since all these vibe coding tools, tons of founders starting things that probably have low depth, meaning there's not a lot in the product. It was easy to get up and running.

Maybe it was easy to get a little to scale, but the insight wasn't that deep or the pain point wasn't that deep. And so when we think about the easy, ease of building the product. So we spent all the time thinking about the moat specifically. And I feel like that's kind of the inverse around, not just how hard is this product to build, but why is this going to be a great product with scale? Why is it going to be hard to rip out?

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And great financial decisions come from having a complete picture and proactive management for your income expenses and investments. Take control of your finances with Monarch. It brings together all of your accounts, investments, saving goals. and spending into one place, making it much easier to understand where your money is going and whether you're actually on track to achieve your financial goals. What I like most about Monarch is that it doesn't just tell me what already happened and helps me plan ahead.

The AI assistant lets me ask questions about my finances in plain English and the AI weekly recap highlights spending changes or upcoming expenses before they become surprises. It's like having a financial advisor in your pocket. Write your own money story with Monarch. Use code invest at Monarch.com to get your first year of Monarch core half off at just $50. That's 50% off your first year at Monarch.com with Code Invest. Growing up, I thought managing money meant paying bills and balancing a checkbook. But as you know, that's only a small piece of the financial puzzle. Managing your money takes more than just checking your bank account every once in a while.

And great financial decisions come from having a complete picture and proactive management for your income expenses and investments. Take control of your finances with Monarch. It brings together all of your accounts, investments, saving goals, and spending into one place, making it much easier to understand where your money is going and whether you're actually on track to, your financial goals. What I like most about Monarch is that it doesn't just tell me what already happened and helps me plan ahead. The AI assistant lets me ask questions about my finances and plain English and the AI weekly recap highlights spending changes or upcoming expenses before they become surprises. It's like having a financial advisor in your pocket. Write your own

money story with Monarch. Use code invest at Monarch.com to get your first year of Monarch core half off at just $50. That's 50% off your first year at Monarch.com with code invest. This comes back to being a second level thinker on the market. Have you thought through the integrations, the entire, the existing software stack today? If someone just says this is a big market and here's a problem I'm going to go after, that might work. We tend to be more convicted when they can say, here's like the treasure map to win. And in many cases, it's this is the wedge to get in the door.

It's the way to get integrations. But if you have a 10-year review, you're thinking about defensibility. You're thinking about why is this the best part of the market to go after? One of the analyses I'll sometimes introduce to founders, if they don't know it, is a profit pool chart. And all it does is show an industry on the X axis, the different stakeholders in a value chain, and on the Y axis, it's the margin. And so when you see it in a chart, it's basically you can see visually where are the most profits owned and by who and by what margin. And it's okay if they don't know that, but what I like to understand is like, where does your vision intersect with that? And maybe tell me about the industry.

Like how has market share changed over the years? That tends to force you to say, huh, is my wedge really strong? Is my position going to be defensible if I get there? Those are the questions we try to better understand defensibility. The way that we think about it, our business is a little bit different in that we have the media side to business and the venture side to business. And we always think about not what happens if AI gets better, but what happens when AI gets better? How do we continue building value?

On the media side, we think about, well, what will continue to be true? People still want the best guess. People still want to see how the top people are thinking in the space. What will AI improve? AI will improve guest booking, guest follow-up, editing, all these things. So we think about, are we in a business where the pace of a. AI and the acceleration of AI hurts us or helps us. On the venture side, it's almost all about access to these companies. Our value proposition is connecting them to these 10 trillion and

AUM and guests. Are any parts of our business getting disrupted when AI improves, not if AI improves? A lot of people look at it defensively. Like how do I defend against AI versus thinking about how do I build my business that is accelerated by a? We've built a bunch of agents. I would say on the early stage side, I think some of these tools will have. help amplify the things that you care about. So I'll give you a couple examples. So I'm sure you use tools like granola and scribes and whatnot. One of the things that it's been helpful is stitching together. What are the patterns that we've cared about in the past and making sure, are you being more thorough in your follow up conversations? Are you covering all the points that matter

when you think about a long history of investing? The other thing it's been helpful for is getting to founders more quickly. There's a lot of tooling out there across data and I where you can say, here's a set of traits that we care about and here's maybe some public data around writing or things that they've published that lets us increase this top of our funnel and then choose to proactively go after some founders because we feel like they might be founders that we're going to like. The parts that it's not going to replace is just the quality of your judgment. The quality of how you build trust in person. This is still a business where the founder picks the investor. It's not like buying stocks in the public markets.

So there's a lot of things around efficiency, thinking about analysis and whatnot. But I don't know that it's going to replace how you pick and more importantly, how you win that deal. You mentioned you use agents to find traits of founders that you would want to talk to. And I think it's so important with AI integration gets lost in the details. How do you exactly do that? This is a work in progress, but it's where we've started to have some success. And a lot of it is really, again, this is specific to us where we can look at a profile or a body of work online and pull together and say going back to writing. That's something I think a lot about.

So you can even start to train a model and say, based on someone I've never met, but I've got all these artifacts around how they describe themselves on their LinkedIn profile. What have they said on a podcast? Maybe they have a blog from a couple years ago. I can then start to piece together a picture of, I haven't even met you. But, like, boy, you have really clear thinking in a way that reminds me of another founder I backed that we had a lot of success with. I don't think that is anywhere close to making a judgment on investing, but it's helping pull together. Can you reach out and find founders before anyone else? And can you also find a better hit rate from the first meeting to the second meeting?

That's another thing we think about, which is not just the total number of meetings. Are we finding more of the people that we should be backing? Is your new model better than your old model? You're just trying to get better every day, like a little bit every day and just try to find edges and experiment with things, as I'm sure you guys are. But a lot of it, you're not changing the core judgment, but you're saying, can we make better decisions every day? It reminds me of this parable. All clear writers are clear thinkers, but not all clear thinkers are clear writers. So if you do have clear writing, you are a clear thinker.

And it's just such a great razor to get to the essence of whether someone's a clear thinker. The reason I've always clung to writing, whether it's email back and forth when we're in touch, or I love looking at, did they have a personal website at some point that they forgot about? It's kind of like breadcrumbs over someone's journey. One of the interesting things is it's not that were they an amazing writer eight years ago. It could be, wow, I saw how they wrote eight years ago and how they write today and like, boy, they did something. You can find clues around this growth mindset. Writing matters for just clarity of thought as well.

How are you going to recruit a talented person to join you? How are you going to fundraise? But it also just shows you a line around maybe they've really improved. Maybe they just became amazing writer and thinker. It's another way to tell that speed of learning that you're focused on. I was just on a podcast with Jason Gallaghanis, and we had this debate on this panel about whether using AI and emails and communications was acceptable. How do you look at that?

Is that a positive or a negative trait? That's become something. where you have to really discern because I think a lot of written communication has become AI enabled. Sometimes it's done for a position of helping on grammar. Sometimes it's done entirely by AI. For the most part, today is still easy to tell, but it's increasingly going to be more difficult to tell. And I think this is where the in-person really matters. Seeing written communication is helpful, being able to have a spar, sparring back and forth in-person on a topic, I think is when it's going to reveal whether the person has that depth.

whether they really wrote it or not. It's going to make it more challenging, but it just makes that, like most things in life, it's going to elevate the role of in person. It's going to elevate the role of going on a walk together, going to have a coffee or what have you, especially in the early stage business. Because I've thought a lot philosophically,

even internally, I'll draft up an email and then I'll have AI make it sound better. Because I don't want to train people's cognitive resources to figure out what is that I'm writing to them. A.I. is really good at kind of cleaning it out. A lot of this comes back to intent. why did I do that? Was I doing that to see my business partner and the other team members? Was I doing it from a place of care and wanting to? There's an intent aspect there. There's also

a disclosure aspect. Oftentimes I'll say written with love from AI, but I think that's something that's evolving in real time in the market. That's a very nuanced point around decisiveness. And that's like another trait you always want to understand. And decisiveness is not just, how did you choose this vision to go on this journey for 15 years? Decisiveness could be as simple as how did you think through using AI to edit the email? Did you use it because you're trying to improve your grammar and you're communicating in a fundraising process and it was well-intentioned? Or did you just use AI slot to respond? And the decisiveness by that was a fairly low quality. So that's the nuance you want to understand. It's really hard to get at that

unless you just go deep with someone in person. It's really hard to do all of this online. But coming me back to your question of how do you tell? But you'll know pretty quickly in person. Like, if you just try to go deeper around simply, what do you know about this market? Does it match up to your answers in writing? It comes through very quickly. AI in venture capital. It's another one of these memes that everyone's talking about, oh, well, AI is changing the way that I invest, changing everything about my firm. Is AI really changing your firm? And what are some early adoptions of AI that you see a lot of return on? The biggest thing so far has been increasing the throughput and quality of founders that we can meet. And a lot of this comes down to,

there's a lot of tools out there that can now identify individuals often before it's public that they're starting companies. You can use some of these tools to help say, what do we care about things like writing, things like clarity of thought to say. The venture business at the early searches is always a ground game. You always have to be offensive if you're doing this really well. But these tools can say, hey, are you being smart when you're offensive? Are you finding, it's not just finding people. It's finding people that have a high likelihood that you want to be in business with. That's the first part where it's had an impact. Again, it's not making the decision, but it's helping you see more. The second part is really there are aspects of doing diligence using these tools. Again, I don't think those are making decisions.

They're just helping you process more companies at the same time. And so I do think a lot of smaller funds have the resourcing to process a much higher number of deals. than they would have a couple years ago. Those are the main ways today. Like, I don't think it's changing much about how you make decision. I've heard stories of some funds with an AI investment committee member who's non-voting. And I think there's a lot of great experimentation, trying all of this stuff. We're in the business of learning. How can you invest in founders and then at the firm level not try these things?

So it's been great on that front on the early stage side. I still think the earliest stages is still a very human-to-human relationship. And a lot of that comes down to these companies just take so long. They're incredibly hard to get off the ground. I'm not sure founders are going to eventually want some AI-only lead investor. Maybe I'm wrong, but I just don't think that's the case. Sometimes I question some of these AI. Some of these things are so memeable that's like, are they real?

Are they just traveled through the social media very quickly? Because it's such a sexy narrative, perhaps overly simplified. But I think one of the trends I see across different venture firms is what could be called back office versus front office. We have the back office, figure out which founders we want to talk to. And then we have the front office, the human one-to-one relationship. We have the back office go through the deck and see if it's an obvious no or go through a term sheet, see if it's obviously off market. And then we have the front office negotiating or meeting the founder. So that's one of these kind of simplified.

But the dynamic of back office in the sense of like accounting and some of the reporting workflows, there's definitely a lot of opportunity there. On the point you described of looking at the deck, I don't feel like you can disaggregate that. The person who is the one building the relationship with the founder, who's the one who's going to eventually have to win, they have to be close to the work. I don't think they can entirely depend on AI producing the questions that need to be asked. I think they have to put that thought because if you're making a commitment for

10 or 15 years, you don't want to outsource that thinking. You might want that to help augment your thinking and say, hey, here's another question that you might want to consider asking the founder. But I feel like the separating the salesmanship, the winning from the actual investment judgment. I wouldn't want to do that personally, but maybe some people are. Said another way, you're getting a lot of your benefit, not necessarily in figuring out exactly where you want to invest a funnel so that instead of having seven negatives out of every 10, maybe you have three negatives out of every 10 that and would give you two and a half times. Yeah, so I think when the companies, I'm sure there are some funds when the companies are a later

stage and there's metrics. Some funds have very specific buy boxes. They look for X percent growth. They look for Y scale of revenue. At the earliest stages, the decks are helpful, but there's typically no product, there's typically no traction. And so in that model, you would be depending on the AI to ingest everything the founder is saying, all the interactions, and then making a decision. So I think, again, you can use these tools to help you, but you have to be the engine, and then you have to figure out how to put these tools around you to hopefully make better decisions. From a human resources standpoint, have you changed with 12 below how you plan to hire out internally? One of the things that great talent, whether you're coming in the industry for the first time, or you've been doing it for a couple of years or you're seasoned, I think those individuals just have a killer instinct early. It doesn't mean they have a track record, but they just develop a nose for people assuming they want to do early stage investing, where you have to have this felt sense about the person and then you have to have a felt sense about the market.

One of the areas where AI has been helpful is it can do a lot of. the sort of tertiary work around a market size, analyzing financials. And so I still think those are valuable skills, but I think they are increasingly, in a lot of firms over 10 years ago, they would have hired younger people to process all the information. The left brain type of... Yeah, to write a memo, to analyze customer calls, to look at a financial model. And I think some of that today can be automated. Again, you have to put work around it.

You can't just trust it. But I don't know that anything is going to change around what matters to the founder. Can someone build trust quickly? Can they have an instinct on how to get to that founder really quickly? When it comes to the decision to invest, can they sit in front of that founder and go on a walk or meet them wherever they are and still win them? I don't think any of those traits are going to change. And I think the best firms are always looking for people who can do that. Some of the other stuff that we talked about around analysis, I think, is going to matter less.

Respectfully, what you're really saying is that you've completely changed your hiring practice from these analysts that are basically doing this analysis and doing these models to what I would call mini partners, somebody that you want to see a partner five to 10 years out there just earlier on in their career. That's a great point. I mean, I think what's happening is access and awareness around the people starting companies is increasingly more accessible. What is scarce is the judgment. can you sit in a first meeting and with really good accuracy, say, this is someone special, let's go to a second. And the judgment doesn't just come from reps. I'm really obsessed with getting these thousand reps, but a person that didn't have good judgment to start, even after a thousand reps, would come to the wrong decision. It can be developed or you can start to see it early.

You can see it in people who haven't really been practicing the craft, but they just say, yeah, something about that founder was really special. and they start to learn how to put words around it. You're actually right in the sense that going forward, I think that has always mattered, and that's kind of the reason I said nothing has really changed because I think that kind of is the difference between excellent investors versus not. But I think for us and in general, a lot of firms,

focusing more on that quality of judgment rate of learning is probably more important than do you know how to write a memo in a way that we need? Do you know how to do a financial model in the way that we would analyze? it. Are you going after a different type of analysts and associate? Do they have different background, different pedigree, different career path? To the firm is just myself and my partner Taylor. We're an equal partnership model. We are going to expand the firm, but we actually take a similar

view going back to the earlier part of the conversation on founders around it's not really bounded by levels of experience where you went to school, what companies you worked at. It's D.J. just have a slope that we think can be incredible for the types of founders that we want to back. And then there's also things like cultural fit. We're a small firm. Do we love being around you? Do we feel like you're raising the bar? But I would say it's a lot of the traits that we look for in founders. There's a nuance where we fall in love with the person who really wants to be an investor. And what I mean by that, the clues that I look for is like how have they learned about investing? Do they talk about being an investor, but then spend their free time doing other things,

or are they constantly reading letters trying to meet people to learn from? And I think that's probably the thing that we look for, but the traits that we look for around unbelievable chip on their shoulder, something to prove to the world, second level thinking, really important, not just as a founder, but as an investor. And the resilience component is just as important, especially in these extremely long journeys, where you really don't know if a company is going to be successful for 8, 10, 15 years. And so somebody who is just very inwardly focused is passionate up being an investor for the rest of their career, tends to have that resilience because they're convicted in their long-term path.

I realize as we're talking, I also looked for the second level thinking. I don't frame it that way, but I always like to ask why and just keep on asking why and see if people really at a basic level understand what they're talking. One of the other things, I don't want to say test, but I'll try to probe on, especially in markets where I don't know anything about it, but a founder clearly knows a lot, is to almost try to push on their points and take the opposite view. And the point isn't actually the challenge, and the point is to see how they approach being challenged. Going back to second level thinking, the people who have thought about the problem in the market every way possible, their approach is not defensive. They actually are like, oh, great question. I've thought about that angle. And I've talked to these 17 people. And here's why I think that's actually the wrong point of view. So I think you just learn going back to how deep are they? And I think

that's just such an important part of being a founder. Putting my master's psychology hat on, sometimes people get triggered because they don't have a strong point of view. So it's actually threatening to them. Feel exposed. Instead of accepting it, they project their anger onto you. One of the other things I'll try in a first meeting is, I mean, I don't know if you do this, but like, if you're a professional, you go into things prepared in your head. But that doesn't necessarily mean you're trying to run the meeting in a structured way. And oftentimes, whether it's the first or second meeting with the founder, I'll kind of leave it open in it. I'll give an overview, a proper introduction. But then it's like, well, where do you want to take this?

What do you want to accomplish with this time? Obviously, in many cases, they're fundraising and whatnot. But I think the people who are sort of maniacal, they've got a view, but it's nuance. It's subtle. It's not going to be, well, let me run you through your pitch, this pitch deck and go through every single slide. It's going to be, I'm going to build some serotonin up. I'm going to get to know you pretty quickly.

But in the back of my head, I've got things that I got to accomplish in this meeting. I've got points that I've got to make. And I'm going to quickly get the conversation through those points. And I'm going to navigate it, but I've got a goal here. The other part that we look for also, though, is are they just like learning machines? I feel like a lot of founders sometimes feel like a pitch meeting is the investor sort of grilling them and them having to answer. But the thing that I actually really love and why I try to keep it open ended is I love the founder who says, hey, you mentioned something that might be relevant to my business. You talked about a company that you either was successful or failed that you worked on.

I'm going to interrupt this meeting and I'm going to pull all that information out of your business. brain. And that's also a telltale sign of someone who's incredible. It doesn't happen that often because sometimes they either don't want to mess up or they don't even think to do it. So I love that, hey, where do you want to take this? Yes, we'll get through the pitch. But like, I almost, if I just pretend like I'm just there for you, what do you get out of it? And usually what you want to see is they're just incredible learners. And they also are almost starting to interrupt. They're almost not shy about it. They're like, I'm in pursuit of this vision. I don't really care if you invest or not, but I'm going to make this one hour helpful, and it's going to advantage me on my journey. Alex Hermosey recognizes all the billionaires that he met or many of them would be just these freaks at learning things.

So the story says is they would be seeing somebody putting in a light bulb or an engineer work, and they would just be asking essentially, why did you do this? Why did it? Why not this way? They're just intrinsically curious, whether it's a light bulb or a business or a market, it's almost compulsive.

They have to learn more. Yeah. And I think that's one of these things where you never want to lead the witness because I think a lot of founders know that rate of learning, being learning machines is attractive to people. They listen to podcasts. Yeah. They listen to podcasts.

And so I think that's where if you take the approach of let's just have a conversation, this isn't a pitch meeting. What I love to understand is like, where do they learn? like what are the sources and one sometimes you'll be really surprised i mean youtube's an incredible wealth of knowledge like the corners of youtube and so you'd be surprised how people find ways to learn and i think the other thing when you figure out how people learn one of the things that i try to figure out is like have they been really clever in their life they can be really clever about learning but have they just been clever in their life and i feel like that's another trait that you

want to look for especially for early stage founders one of your hottest takes is that venture capital today is obsessed on underwriting $100 billion outcomes. Why do you think that? People are considering outcome size as the input. And I think what you need to think about is what are the inputs of those companies that eventually have become $100 billion or trillion dollar companies. And so I think this goes back to earlier in our conversation. If people are talking about the foundation models or companies like SpaceX, being a student

of history is really important and really not looking at what those companies are today, but what were they like in the earliest stages in saying, what are the patterns I can learn about those companies where they were likely in many cases underappreciated or not appreciated by the market at the time? We're in a moment right now where the capital has really concentrated into a select few companies. And on one hand, that is hard for some entrepreneurs,

but on the other hand, that makes a lot of opportunity if you're not just focused on those companies and you're focused on the shape of those companies when they were much earlier. There's this concept called seat strapping, which is a play on bootstrapping, which is you raise a seed round and then you never have to raise again. There's a whole leaderboard tracking people that did this. What do you think about that? That was a response to disliking the need for venture capital.

I think I'm sort of neutral on it because I think generally if you're going on a very big endeavor, a journey where you are going to need capital, you need to find this middle of ground of marshalling capital. capital, marshalling talent, sometimes talent comes when there's more capital. There are definitely businesses where they shouldn't raise venture capital. And I think if you are in a market where you either don't want to be on a company that needs to be fast growing, or you're in an end market that's at a size where you shouldn't raise venture capital. I actually think that's amazing, which is don't raise a lot of capital, own a lot of your business and just be in control of your own destiny. But I think if you are trying to build something great, I think it's important to think about how capital is going to help accelerate that because many of the best markets are not in a vacuum.

You can be early to it, but it's likely there's going to be other competitors. And so if you really want to win, you have to ask yourself, am I going to be able to get away with that as a seedstrap company if my next biggest competitor raises $100 million? How am I going to feel? So another way. If it's a winner take all market and you're not number one, you're going to lose. Ultimately, a lot of it comes down to your drive in what you want to build and the end market size. The end market size, by the way, may do that decision for you if capital isn't there. It feels like seat strapping is also almost a fun thought experiment, but should be taken literally, should be taken as a philosophy to consider in certain circumstance.

Going back to decisiveness, seed strapping implies you took a bit of capital, but then made the decision to say, I'm kind of getting off the venture capital train. And so then where I would go is like, well, before you even started the company, why did you raise that capital? assuming that capital was initially on that train. It feels like maybe there's a change of heart, which is totally fine. But that would be something I would want to probe. It's like, well, if you want to go on this journey, like, why would you bother with high cost capital? It's going to be expensive. People have high expectations.

I think the nuances. Some markets change. People realize maybe the companies won't grow as fast as you can, and it might just be the right outcome for the company. Yeah, doubling and tripling down when you know it's not going to work. You study a lot about these cognitive biases of different investors. What are some cognitive biases that you have that you worked on? It's having experience in markets that either didn't work or business models is a common one. I really just having that beginner mindset both on founders, but also company business model and market is really important.

It's sort of a business where you can only lose one times your money, but missing out on a company that can be incredible work. turn is very painful. So I think being willing to say maybe we have scar tissue from the past and you have to simultaneously say this time is different. So I think there's some blending, but you have to be cognizant of that. The other thing is also if you feel like you had a bad experience with a certain founder, that doesn't mean someone who reminds you of them is going to be that same experience. Just treating at each net new founder and opportunity is completely isolated from the past because chances are it is. It's about not over pattern match. You can be mired in star tissue from the past, but if the world is totally different as it is today compared to

five years ago, you may miss the best opportunities because you're so focused on it not working again as opposed to, well, what has changed in the world? How has that changed in the world opened the doors? Is there a brand new oxygen that wasn't possible five years ago if there's scar tissue for five years ago, that may not be relevant at all. And it could cost you a lot. Yeah, the two most famous examples, web van became Instacart and pets.com became chewy, both multi-billion dollar outcomes. And for at least a decade, it was, it was lampooned as these are like the worst business ideas of all time. It's quote unquote, everyone knows. How could they do something stupid? And then a decade later,

they're at $10 billion. That's a great example. I think it was Michael Moritz from Sequoia, like to have the fortitude to do webvan, see that through, and then make the early investment in Instacart again, I actually don't think a lot of people would do that. I think it requires you to kind of reinvent yourself, open up your mind, and sort of say, are you taking the right lessons from it as opposed to the lesson of just don't invest in that category again? And that makes it doubly hard when it's not your own money because now you're not only making the decision to invest and avoid this over pattern matching, but now

you're opening up yourself of criticism from your limited partners on why you're making the same mistake twice. There's definitely an aspect of in the earliest stages of if you make investments or do you have courage? I mean, do you have courage looking silly? Maybe your peers will laugh at you and they won't understand what you're doing. But where I come back to is that's like that's the job. Your LPs are not giving you money just to do what the market's doing. They're giving you capital to generate something that's superior than the market. So I think having a very specific view on how your system, your model, the way you generate alpha is different is really important. If you go back 11 years ago when you first started as a venture investor and you could give yourself one timeless piece of advice, what would that be?

Just take more risk. I think when you're starting out, it's always easy to worry about the investment that won't work or you're just, you're more risk off because you're early. but risk is how you learn, and more importantly, if you fail a lot quickly, you might actually become a better investment. So I require the right people around you to accept. Absolutely. I was really lucky to be in great environments where I was empowered early. I was empowered to take a ton of risk early.

That's not the case for everyone. So, but I think if you're committed to being in the venture business for decades for the rest of your career, it's one of the things where you want to get those wraps. You want to get the track record. You want to build the lessons. really early so that when you start to make even bigger decisions that are more costly, you feel like you're picking really well. Byron. This has been episode Masterclass. Thanks so much for stopping by.

Thank you. Thanks for having me. It was great. Thanks.