E264: The Asymmetric Edge: Generating Alpha in Venture

How do the best venture investors consistently spot unicorn founders before the rest of the market even knows they exist? In this episode, I talk with Jamie Lee, Co-Founder and Managing Partner of Tamarack Global, about sourcing asymmetric deal flow in deep tech and why founder referrals are the single strongest signal of future breakout companies. Jamie explains how Tamarack applies hedge-fund-level diligence at the seed stage, why intuition and pattern recognition matter as much as data, and how concentrated conviction—combined with relentless research—drives their unusually high unicorn hit rate. We also explore humanoid robotics, labor automation, and why the next industrial revolution is already underway.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00David Weisburd?

  Jamie, I've been very excited to chat. Welcome to the podcast.

• 0:04Speaker 01

  Thank you, David. Thank you for having me. Really excited to be here. I've listened to you for a long time. And so, thank you.

• 0:11David Weisburd?

  You have, according to Ilya Strubalov's unicorn list, you have 19.2% of your companies end up at the C-stage becoming unicorns. Tell me about your sourcing strategy. How do you go about sourcing such a high quality and high caliber companies?

• 0:27Speaker 01

  The number one signal that we found, because we've regressed a lot of this data and looked at where the companies that we've invested in, where does it come from? And we crunch these numbers all day. The most powerful signal has been the founder referral. So not the peer-to-peer, not our other competitors in the space. That tends to be about a third of the time. The majority of the time and the highest signal time and tying it back to the investment process of which companies end up being billion-dollar outcomes. Or when I get a phone call from that five out of five founder, often they may already be, you know, a multi-billion dollar company.

• 1:07Speaker 01

  And they say, hey, Jamie, like, hey, I just met this kid. He's an also good note. You need to go down and meet with him or her like tomorrow. And those are the strongest signals that we get. And those are the ones where my antenna kind of pop up. And there are only a handful of folks that I will kind of listen to in that regard. But thankfully, some of them are already in the portfolio. But when they say, you need to meet this person, you know, I'm going to see them in the next 24 hours, most likely. Of course, there's many other ways that we source, but I think that's the most powerful one.

• 1:45David Weisburd?

  Why do you think that founders, specifically unicorn founders, are the best source for deal flow?

• 1:54Speaker 01

  Oftentimes, they're already looking at these companies. They might be developing commercial relationships with them. They may have actually already worked for them. Tom Mueller was famously the number one employee at SpaceX. If you count Elon as zero or two, if you count Elon as number one. So you know how many funds that have been spun out of SpaceX? How many companies that have been spun out of SpaceX? Every single one of these companies or kids or funds has worked for Tom in the past. He knows every single one of them. So if we're talking about aerospace or defense and space defense or where those things meet as a category or just as a for example, Tom knows these people.

• 2:39Speaker 01

  So when he calls me and says, hey, Jamie, you've got to meet this kid. He actually knows the company and says, you know, we use this company. We don't use this company. This one's great. This one's pretty mediocre. And this kid who worked for me is the best, one of the best engineers I've ever had.

• 2:57David Weisburd?

  Some of the best venture portfolios of all time, literally ranked at the highest, are not actually venture portfolios. They're angel portfolios. They're Mark Andreessen's portfolio, David Sacks's portfolio. Some of the super angel portfolios, technically some of them took money. And that's because they had this asymmetric information where they were investing in friends that they went to at Stanford or in business school or engineers or engineers that had worked for them. And they had the benefit of knowing how effective these employees were over years of working with them.

• 3:29Speaker 01

  To be truly excellent at this game, you know, if you want to play with it, if you want to be in that category with Sacks and Mark Andreessen and those folks, you're not in venture beta. And there's, in a venture beta, it's not easy to get to venture beta. But I think there's a lot of firms out there that are offering venture beta. That's good and that's fine. But if you want to be truly excellent, you need asymmetric information. Now, that's true in private markets and it's true in public markets. I used to work in public markets there too. What you just said, David, is absolutely true. There has to be something out there, some kernel of truth or some kernel of information that you're getting that not everyone else has.

• 4:11Speaker 01

  And that's the kind of, that's part of the secret sauce of finding, you know, the next unicorn or next unicorn or, you know, major company.

• 4:19David Weisburd?

  When you find this next

• 4:23David Weisburd?

  Unicorn or Decacorn that's sourced through you from your very top founders, people that they worked with. How do you go about winning? These tend to be extremely competitive rounds. How do you elbow out the other VCs in that round? And what's your secret to winning?

• 4:42Speaker 01

  It's a terrific question, David. And I think that the honest answer is that we have to out hustle them as a smaller fund. This is where kind of some of the hedge fund background kind of plays to my advantage and plays to our team's advantage. Just riffing a little bit here, but when I first got into venture, I just didn't see the same level of diligence and homework that I saw that was being applied at places like Co2. But before Co2 had made this or they, you know, headed to become a crossover fund, investing in publics and in privates. Because the amount of diligence, the amount of research that we would do

• 5:25Speaker 01

  to get something in the book, at the public book at Co2 before, you know, they had a big privates book as well. So when you bring that level of homework to a founder at the earliest stage, and you say, hey, listen, I have a 50-page deck, you know, or I have a 50-page memo, rather, on your company. And I am going deep, I'm going almost private equity deep on your company at the seed stage. And I'm going to share this information with the, with the growth players or with the seat, you know, whoever is writing the next check into the next round. I'm going to help them underwrite your next round. And oftentimes, you can beat people with the research that you do. And I think that that's something that goes unsaid or it doesn't get said enough.

• 6:08Speaker 01

  Maybe I shouldn't even be revealing it publicly here.

• 6:11David Weisburd?

  I had JR from Industry ventures and he talked about just the meticulous diligence process that they go on, both on funds as well as deals. And a lot of people in precedents seed, they kind of throw their hands up and say, well, it's unknowable. It's unknowable about this market. By the time Bain creates a research report, it's already too late and all these things are unknowable. And that might be true, but to me, that's also an excuse or a form of laziness to not do as much as you can to try to get more information in the space. The worst case is you end up getting information that is not very useful or that doesn't move the needle.

• 6:53David Weisburd?

  But I think people don't do the necessary hard work that takes to both diligence, both companies, founders and everything, and just kind of use this whole framing of a precedents seed just to be lazy, for lack of a better word.

• 7:06Speaker 01

  I agree with you and I, and I don't want to cast shade upon any peers or any peer firm, but I do agree with you that the, there is a tendency or proclivity for folks out there to at the precedent level to just say, hey, you know what? It's a small check anyways and it's a big end market. So let's just kind of see where this thing shakes out and this guy's ex-Adrol or ex, you know, mock or, you know, and so it's probably a decent sharp ratio bet. But you can go much deeper. You just have to get creative and you could become your own investigative journalist of sorts and just go down any rabbit hole to find bits and nuggets of information that

• 7:51Speaker 01

  may surprise you as being incredibly informative in uncovering blind spots and things like that.

• 7:57David Weisburd?

  Perhaps it's not binary, but one of the main sources of diligence that I think that needs to be uncovered in these precedents seed opportunities is why that individual is leading this name brand startup. Let's say they're at Anduril at SpaceX. Again, it's not binary, but they tend to fit in some continuum as they're not a great employee. They're burning out or they're the top of the top and they want to build something even bigger. Or they want to build something for themselves. And zeroing in on that diligence on just how quality of an engineer

• 8:36David Weisburd?

  that first one or two employees are at a company, I think is one of the things that goes under diligence.

• 8:44Speaker 01

  You know, I started my career at Goldman Sachs and it was the, it was the ultimate training ground. It was where you went to, you know, to, you know, to cut your teeth. And I think I sort of use SpaceX as the new, as kind of having that ethos. And I think it's the, their star is so bright that's shining at what is admittedly now a large, a large institution. You know, let's use SpaceX as an example to where they've got bigger dreams and their ambitions are so bright that they can, they can chase those dreams. And that might not be starting another space company. You know, in many cases it's I want to build small modular reactors in the nuclear realm. And this is my dream.

• 9:27Speaker 01

  And due to, due to the beauty of the SpaceX tender process and the liquidity around the name, you might have some of these, you know, younger people that are in their young thirties. You know, I'm 41 now, so they seem like kids to me. But, you know, they might be in their young thirties and they've got quite a bit of money in the bank and they can start, they can start, you know, their own company. And these tend to be very ambitious young people. So I think it's more the latter that their star is so bright that they, you know, they're not running again. They're not running into any ceilings at SpaceX. It's just that they, they can have a much larger outcome for themselves. And I think it's more of that.

• 10:07David Weisburd?

  When I spoke to Jamie Goll from Wave Function Ventures, he's a former SpaceX guy. He said that people at SpaceX fit in three different camps. One is the ones that burnt out after six months. So they just couldn't take it. They couldn't take this responsible engineer culture, which basically means that every engineer was responsible for everything in their orbit. They couldn't hand it off and they couldn't kind of say, that's not my job. The other end of the spectrum were these SpaceX lifers. They're the people that are there for 10, 15 years that just could not see a bigger mission on the planet than making the human species multi-planetary, going to Mars and all this. And then there was people in the middle that would go there for five, 10 years, build their skill set, build their network

• 10:52David Weisburd?

  and go on to start other great things. So he kind of saw this as these three camps.

• 10:58Speaker 01

  Jamie's a good friend. So I talk to Jamie all the time and getting his experience is incredibly helpful. Part of this business is bringing it back to that sort of asymmetric advantage is collecting people like the Jamie Goll's out there that are just a phone call away. We just chat about this kind of stuff. And so that's, that all feeds back to those information loops that are asymmetric and he's got a good, as good of a take as any.

• 11:31David Weisburd?

  Tell me about the humanoid robot space. You're an investor in Figure, which, just to bring it back to Elon, directly competes against Tesla. Elon says that the optimist is going to be their biggest product ever. Talk to me about the humanoid space. How big is it? And what's going to determine who wins that space?

• 11:54Speaker 01

  So let's start from the top. So the labor market, the global labor market is the largest end market in the year. So going back to what I was saying at the beginning, the market for physical labor is about $42 trillion a year. So we'll start there. So we've got a big sandbox to play in. Now, if we look at, you know, many of these applications and many of these jobs within this kind of sector and what are the subsectors, these are not necessarily jobs that we want for Americans in the future, or at least let me say that differently, that I want for Americans in the future. So like picking and packing, you know, there's

• 12:33Speaker 01

  about 150% a year turnover for laborers in this, in this kind of space. These are jobs that can be automated. I believe they should be automated. And I believe in its inevitability that major corporations will have no choice but to automate many of these jobs, especially if we want to re-industrialize and relearn how to build things in America again.

• 12:59David Weisburd?

  One of the things that I'm trying to figure out is whether the humanoid robot space is going to be more of industrial or a residential product. In other words, are we going to get these maids that are cleaning the house and, and, and doing the laundry? Or is it more production lines and automation?

• 13:20Speaker 01

  Elon has said that this is going to be the largest asset class in the world. It's going to be bigger than the smartphone market. It's going to be bigger than the auto market. I think it's both and it's, and it's beyond that. And the math pencils for the reasons we just discussed. So you think about industrial applications and repetitive tasks like, you know, in the 3PL space, worker, worker 247 move this pallet, you know, that contains two sticks of deodorant over to this area. There's that job, right? Think about cleaning hotel rooms. How many hotel rooms around the world need to be turned on a daily basis? All those sheets need to be cleaned. All those towels need to be cleaned

• 14:02Speaker 01

  and rehomed. You think about all the office spaces out there that are cleaned each day. The minimum wage in the United States right now is, is call it like $52,000 or $53,000, I want to say. Maybe it's a little bit higher than that. So you tack on, I'm going back to the industrial application, like the industrial kind of worker or the logistics, you know, worker. You tack on disability and insurance and then you factor in that they work about a six-hour day, but they show up for work half the time and there's 150% turnover. When you talk to some of these warehouse owners, their total cost for each of these employees is closer to $150,000 or $200,000 a year.

• 14:43Speaker 01

  And so when you present to them something that might be $100,000 a year or $80,000 a year, but guess what? The thing can work for 15 hours. It can work for seven days a week. It can work in the dark. It can work in the cold or the extreme heat. You know, there's no COVID, there's no unions, there's no problem, there's no complaints. There's a big 3PL player that's already expressed interest for 85,000 humanoids from FIDIA. So at $100,000 a robot per year, that's 8.5 billion dollars in ARR right there. So that's from one customer.

• 15:25Speaker 01

  So I think that's why if you get really excited very quickly and that they'll play a big role in the future.

• 15:34David Weisburd?

  You've deployed now two funds into the ground. $35 million first fund with a total of $100 million deployed, including Co- Invest and 75 million with 200 million with Co- Invest. What were your learnings going from Fund One, Fund Two? And what do you plan to do different for Fund Three? One thing that I've learned from talking to hundreds of investors, founders and business leaders is that planning for the future isn't just about growing assets. It's also about protecting the people who matter most. Life comes with a lot of important milestones. Maybe you're buying a home, starting a family, planning for college, or simply thinking more intentionally about your financial future. As those responsibilities grow, it's worth making sure you protect those you love. Not sure what kind of life insurance you may need? Concerned about how much it may cost? Think life insurance is too complicated?

• 16:18David Weisburd?

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• 16:35Speaker 01

  The main learnings from Fund One to Fund Two was that we got, we got quite a bit more concentrated in Fund Two. So we started to get a little bit more aggressive and what do I mean by that? I don't mean aggressive like, you know, I'm going to argue down on this term sheet and I want this lick breath and I want, you know, I don't mean aggressive in that sense. I mean like preempting rounds at inflection points. Where, you know, your typical VC might, you know, come to you and say, hey, well, they're not going to raise their Series A till next year. And, you know, I sort of hear that and my first thought is like, well, okay, fine.

• 17:13Speaker 01

  I don't, you know, that's, maybe that's what they told you, but if you ask the question, you know, will they, will they take a little money? You know, will they take a little more money now? So what, what is something that we've done very successfully in Fund Two? Is identify those companies that are, you know, exhibiting some sort of like escape velocity or just true velocity to the upside. And they're hitting just one or few big contracts or they're going to about to win some big strat five program or whatever it is. Calling them up and they, they say, oh yeah, we're going to raise our Series A next year. And you say, okay, great. Well, how about you take another couple bucks from us now, you know, on a safe? And we'll do it at a, you know, a discount to the next round or whatever it is.

• 17:57Speaker 01

  More often than not, you'd be shocked at the response and the response at first is like, well, I don't know. I don't want to take the, you know, and then you say, well, what could you do with another $3 million? I'm making the number up. So well, I could, I could advance this program. I could advance this program. I could hire eight more engineers. And so more often than not, people come to, yeah, a little bit of extra capital right now would be nice. And so, and then that Series A happens and we've already added, you know, more to our breakout winners. And that's, you know, another thing that we've really, we've really changed about our process is just really being, you know, playing offense as opposed to defense.

• 18:39David Weisburd?

  After spending eight years at Goldman Sachs, you went to Co2 and you got to work with Philip LaFonte, who's a co-founder of Co2. What did he teach you about investing?

• 18:50Speaker 01

  Oh my gosh, Philippe, so much. It's hard, it's hard to even boil it. So I'll give you a bunch of four examples because he taught me so much and his brother Thomas as well. Philippe, Philippe is a, is a true savant in terms of boiling down very, very complicated things into the two or three things that really, really matter. And so the, I'll give you a, you know, sort of a hypothetical and then an actual. The amount of times, for example, that I would come to him with some, you know, really complex model and laundry list of the, you know, about a certain company.

• 19:34Speaker 01

  Of the, you know, 45 things that this company would have to just nail, all 45 of them, they would have to nail. And then it could get in the book. And he'd look at me and be like, Jamie, this, this feels like something with too much sole supplier risk. And I would sort of double click on that and let's go deeper on that. And that would probably most of the time, he'd be, he'd be kind of right. The other big thing, which I think is very applicable in the sort of the crossover space, if you think about applying sort of the hedge fund mentality to venture that he taught me, was he always thought it was crazy that sell-side analysts and the rest of the street, and you know, Warren Buffett thinks this way, Jamie Dimon thinks this way,

• 20:16Speaker 01

  that companies being, measuring companies on quarters is just absurd. Even measuring companies on, on T plus one year or T plus two years is kind of absurd. And so he would look at a certain company and let's make up a company like Netflix. I don't know what it trades at right now, but I'm going to make up a number from a few years ago. Maybe it traded at 20 times or 25 times earnings. And, you know, and people would say, you know, maybe that looks expensive optically. And Philippe would challenge the assumption, but he wouldn't challenge the assumption on the 20 or 30 times T plus one or T plus two years. He would say, well, in five to seven years, do you think?

• 20:58Speaker 01

  That they can grow at this rate and do you think that they can get to X hundred million dollar subs? And then say, because I think if you just should think about it this way and this way, if you think about it on a five year or seven year or nine year time horizon, I think you're buying this company at three times earnings. Or I think you're buying this company at two times EBITDA. And then I think he was able to apply that same lens of thinking to venture. And I think he taught all of us, all of us that.

• 21:32Speaker 01

  Cause it's really not that different. We're not really looking at the next one or two years in venture. We're looking at, you know, obviously five, 10 years down the road, what can this company be? And so those are some of the things that I think Philippe taught.

• 21:47David Weisburd?

  I had Dan Ives on the podcast. He, he thinks about public markets very much like a VC. He thinks about if you froze the market for five years, what would you invest in? He was early at Apple, he was early at Tesla, he was early in Palantir. And he takes this private market lens into the public markets. What else did you learn from Philippe?

• 22:10Speaker 01

  Another thing that I'm, I, I sort of blatantly ripped out of the Philippe Lefont playbook, but I'm proud to say that I did is that he would have us rank every investment that we brought to him as a one, two, five from a gut score. And that was literally what it was identified in, in the internal kind of CRM and, you know, portfolio tracking tools. You actually had to input a number one through five. And so I think, you know, and I think that the best investors in the world will admit that intuition, which is really what kind of gut, you know, meant plays a huge part, if not probably one of the biggest parts of, of true alpha. And

• 22:56Speaker 01

  Because whenever we brought something to Philippe, we actually had to put in that that got scored one through five and five being the best. And and then, of course, that would give him the benefit of being able to say, well, okay, well, JB brought this five to me and I can regress that versus the performance of his stock picks. And, you know, it would give him the good lens into our own sense of intuition. We've taken the same thing to Tamarack. We take the same level of approach and it the results and the correlations are pretty striking. And I, you know, I'll just give you an example there that if you're just if you're debating whether it's a four or a five, you kind of know that in your head. You're like, well, they kind of were they were kind of so so on this and they were kind of a four on that, but I really did like this part of the business and that's more of a five.

• 23:41Speaker 01

  You can talk yourself into it being a five and make the investment. And most of the time it doesn't work out. But when you see a five and you know, a five, it's like every fiber of your being, you know, you feel it at the deepest part of your gut and you just know it's a five. And you take a look at that data versus the ones where you were at like a 4.5 or talked yourself into a five is pretty striking. And, you know, I read a an interesting quote from, I think it was from Josh Krasner from from Thrive recently. And I'm gonna paraphrase here, but he said something basically like, my deepest insecurity

• 24:23Speaker 01

  is that I will oftentimes have intuitions about a certain thing or a certain company that I cannot explain to anybody else. But I just have to invest and I love it. And he rattled off a few for examples and they were, I think it was Instagram, Spotify and OpenAI. And and I think that that was a big learning that, you know, it basically goes back to what we're saying, which is intuition. And, you know, do you have it or do you not have it? And I think the best habit and it's something that it's another thing I'll be eternally thankful that Philippe taught me.

• 25:03David Weisburd?

  I think about two things there. One is the Ashton Kutcher rule. So Ashton Kutcher has this rule that if during a pitch with a startup, even for one second, he has the idea of I should quit what I'm doing and go work for this founder, that's a signal for him to invest because the hardest thing at the seed stage is recruiting. That is the highest form of alpha. Taken to the extreme, you could have a completely nonsensical business, recruit the greatest minds in Silicon Valley, and you'll iterate your way into a hundred billion dollar company. The second aspect of that is this mismatch between gut and words. So

• 25:44David Weisburd?

  if you think about what does it mean you have this gut instinct, it's not something that comes from outer space or from outside of your body. It's inside your brain. Our brains are fully encapsulated systems. So we have parts of our neurobiology that syncing together to tell us that this is good. What we lack is actually the ability to fully articulate why we're feeling this way. So the information is there, the information, our gut is essentially our information. Step two is being able to articulate that information, but step two is not necessary. What's necessary is that you have that gut because the gut is the synthesis

• 26:29David Weisburd?

  of all the information that you have as investor. And as long as you have it in your gut, you could articulate it. This applies to factors outside of investing. If you're in a subway, if a woman sometimes will be on a subway and will feel uncomfortable, she may or may not able to articulate why she feels uncomfortable, but more often than not, there's a good reason for why she feels uncomfortable. And it's again, this intuition, the synthesization of information in her head that leads her to this uncomfort. So the gut is a undervalued aspect. Now, you could obviously corrupt that and you could say, this is my gut. This is why I'm banging banging the table. And maybe it's really your ego, or you have an

• 27:12David Weisburd?

  incentive that's not aligned with the rest of your partnership. And you could obviously corrupt this ability to say it's my gut. When taken in the positive and when not misaligned with incentives, it could be extremely powerful.

• 27:26Speaker 01

  That's all 100% true. And I think that where you nail that is in that inability to communicate it, but you just sort of know it. But you may have trouble synthesizing it. I remember taking a social psychology course back in undergrad, and it was basically a finding that people on average, when there's public speaking, you know, if somebody's watching somebody speak at a panel or something like that, they typically make their decision on if they're going to listen to the person or not within the first three to eight seconds. And that's what the studies show, is that in that first three to eight seconds, the person either grabbed their attention

• 28:08Speaker 01

  and had that sort of, you know, I go back again to that idea of grabby toss and poise, or they didn't. And if you ask those people, like, why did you listen to that person? Or why did you not listen to that person? My sense is that they would not be able to articulate it. They just see, they made a, they made a, they made a snap, snap judgment of like, this person's interesting or they're not.

• 28:33David Weisburd?

  A lot of what becomes being a better investor, one is the input of more information, more iteration, more use cases, seeing what excellence looks like. But some of it is also learning to trust your instincts. And sometimes, to this point, you just don't have, you can't wordsmith exactly what you're feeling. I had a funny example. I was at brunch with my business partner, and we were meeting with someone, and she was, she just spent too much energy smiling. And I just learned kind of, I learned to read micro facial expressions. I literally told my business partner, he said, well, she seems nice. What did you think?

• 29:15David Weisburd?

  I'm like, she spends too much energy, too much facial expressions, smiling. I don't think she's authentic. And I ended up being correct. Not that I'm always correct. But, you know, these absurd kind of reasons for why you trust or distrust someone is actually wired in millions of years of evolutionary psychology and evolutionary biology. So sometimes they might be misleading, but sometimes they might be exactly on point, even if it sounds arbitrary or sounds...

• 29:46David Weisburd?

  Like you're being hypersensitive.

• 29:47Speaker 01

  I don't think you're being hypersensitive at all. And I think those are exactly the cues that we kind of look for. And you know, and I think in some sense, being an investor, you are sort of like a social psychologist, or you are sort of an anthropologist, or you are, you know, you're looking for all those cues. And I think, you know, excess smiling, I love that. I love that as a potential, you know, negative signal where, where, you know, of course, the optimist in me wants to say, maybe David, she was just a really friendly person. And you kind of missed the mark on that one. But, you know, my sense is you probably didn't. And maybe, yeah.

• 30:28David Weisburd?

  What's kind of a mindfuck, for lack of a better word, is I would always excuse these kind of behaviors. And I would always kind of judge myself. Oh, man, you're being so harsh. Maybe she's just, maybe her muscles are just more developed in her face. But the, the degree of precision and the degree of accuracy in these micro facial expressions may not be 100%, but it might as well be 100%. I'm also remembered in diligence. The only guest that's been on the podcast three times, Alex Edelson from Slipstream. He's extremely good at diligencing. And I've, through him, I've actually learned that diligencing

• 31:08David Weisburd?

  managers and CEOs is certainly a skill. And one of the reasons for his edge is because he started out actually as a lawyer. And part of his job was to interrogate people. And he learned, to your point, these micro facial expressions, how to phrase questions in certain ways. And the reason it's such an important skill is one, is I would argue, especially in manager selection and references in general, I would argue, references are one of the most important sources of alpha. And, and because references are essentially game theory, where the other person is disenthusiastic, to tell you the truth, being able to be

• 31:49David Weisburd?

  a top 10% or top 1% reference interviewer, I guess, is a seriously underrated skill and a significant source of alpha, in my opinion.

• 32:01Speaker 01

  I think what you said is is 100% true, and I think it translates directly into what makes a great interviewer, because it's like, it's kind of like jazz, right? We're kind of riffing off of one another, right? You're kind of reading what I'm putting out, feeling what I'm putting out, and I'm, you know, trying to do the same with you. And if you are kind of in sync and in symphony and in orchestra with the other person, and then you might create something interesting. So I think, you know, but the ability to to know when there's some dissonance in the room, or when there's, you know, it's not really jiving, or it's not really sinking because of

• 32:45Speaker 01

  that, you know, whatever it is, that note that whether it's a nose scratch, or an excess smiling, or, you know, look up and to the right, or, you know, any of these things that buddies it from the from the agency of Tommy over the years as well, it's like, it's all those things, all those things, pattern matching, right? It kind of brings me back to what Philippe and Tommy, that was the other thing, it was just, it was just pattern matching, you know, you would, you would tell him a story about a new company that you had just heard about, and you think, you thought this is the coolest new thing that he'd never heard of in his entire life, and he would be like, "Yeah, reminds me of a company I knew in the 90s really well. They tried the same thing, and it failed for these three reasons." And you'd be like, "Well, shit,

• 33:30Speaker 01

  you know, okay, he's probably right, and you know, he's kind of, he's kind of, you know, pretty, pretty good at this." But it's just, it's pattern matching, and it's being able to read between the lines, and it's intuition, and it's gut, it's all these things kind of put together.

• 33:48David Weisburd?

  And I want to take you back a decade ago. You had been at Goldman Sachs for eight years, you're at JP Morgan, you were just about to start at Code Two. What is one piece of advice that you would have got, given a younger Jamie, just entering Code Two, that would have either accelerated your career, or helped you avoid costly mistakes over the next decade?

• 34:12Speaker 01

  It's a great question. I would say, take big risks and put yourself out there. You know, take a big swing and take a big stance and prioritize conviction over caution. Like Stan Druckenmiller famously, you know, has said, put all your eggs in one basket and then watch that basket carefully. Um, we're all pretty lucky to be involved in this game, whether it be venture, hedge fund, you know, finance at large, right? We're in a developed economy. We're all, we're all very lucky and blessed people. Um, and we take our jobs at Tamarack very, you know, as fiduciary is very, very seriously. But at the end of the day,

• 34:54Speaker 01

  especially early in her career, you know, the realistic worst case scenario to having a wrong stock pick, um, it's pretty low. The stakes are pretty low. I think that if I could give myself one piece of advice, you know, in going back, it would be when I felt like something was kind of a home run and I felt like it was just like a no brainer, like pound the table, you know, wear your heart on your sleeve, even if it's out there. Cause there's that bucket of investing, which we, we call it intern, we call it the weird and the wonderful. If you can find something that's, you know, weird and wonderful, you know, that's, that goes back to that information asymmetry that we talked about earlier in this conversation.

• 35:37Speaker 01

  So I would say, don't be afraid to take huge risks early in your career. That'd probably be the, the, the number one thing I would, I would tell the earlier version of myself.

• 35:47David Weisburd?

  Going back full circle, we started the podcast talking about how you guys have had 19.2% unicorn hit rate, according to Ilya Struvalov's rankings. You were number one of any fund. How sure were you in those breakouts, both in terms of the companies that could really become unicorns and then the ones that you thought could become the deck of unicorns? How much was your intuition able to predict those unicorn, deck of unicorn outcomes in retrospect?

• 36:15Speaker 01

  In, you know, in retrospect, you know, obviously it would be intellectually dishonest.

• 36:21Speaker 01

  For me to say that I could say with one hundred percent certainty that I knew that those ones were going to be unicorns or deck of unicorns. But I could say with a hundred percent degree of certainty that I felt pretty damn good about those ones being winning outcomes. You know, I gave the Tom Mueller example.

• 36:42Speaker 01

  The guy's one phone call away from Elon and he's building in space. You call that an unfair advantage? I think that's like the definition of an unfair advantage, right? Can you just kind of skip the queue and get on the next launch? Like, yeah, just text the guy. Sure. Okay, done. You know, or I think about Chaos Industries and I think about John Tennant and Brett Cummings and, you know, they've already co-founded a company, you know, in Epirus, multiple, multiple companies they've founded. And exited Epirus at over a billion dollar valuation. Do I think, and John, and John's a dear friend, one of my best friends and, and, you know, he's, he's an incredible founder. He's a bull in a china shop. He is one of the most connected people in the world.

• 37:26Speaker 01

  And do I want to put another, if I'm another defense founder, do I want to go up against John Tennant? No, is the answer. Like, do I think he's going to win? Yes, I do. So, like, I'm probably coming off as quite confident in these picks. But when I went into these, people said, you know, that there were, these were not, these were not cheap valuation entry points at, you know, the earliest stages. But it's like drafting like an all-star NBA player, right? You're paying up a little bit for talent, but if you want to be sure that you're going to get that deck of corn, you know, kind of outcome. I felt very good about many of these.

• 38:05Speaker 01

  Same with Brett Adcock, we'd already seeded him when he was at Archer Aviation and exited that company at close to a three billion dollar valuation. So we were his first phone call and he did Figure AI. And he said, hey, guess what, guys, we're doing robotics now, we're doing humanoid. And we said, what's a humanoid? You know, and that was three years ago now. And so, you know, I would say honestly, David, without, without sounding braggy, I felt pretty confident about many of these companies.

• 38:34David Weisburd?

  Well, Jamie, appreciate you jumping on the podcast. Look forward to sitting down in person very soon.

• 38:41Speaker 01

  David, thank you for having me. This has been great. Loved our conversation and I really appreciate it. And yeah, let's get together soon.

• 38:49David Weisburd?

  That's it for today's episode of How I Invest. If this conversation gave you new insights or ideas, do me a quick favor. Share with one person in your network who'd find it valuable, or leave a short review wherever you listen. This helps more investors discover the show and keeps us bringing you these conversations week after week. Thank you for your continued support.