Raised $630,000,000 for that first fund. What was your pitch? The pitch was first and foremost, no. You actually can build a huge business, and you can do so in a way that is more reliable. This is Dan Ahrens. He runs a $2,000,000,000 investment firm in New York City that he started at just 29 years old. I wanted to know what his secrets are. So today, I had him here at our studio and asked him to teach me everything he knows about investing.
What is the number one trait that makes a great investor? Curiosity. There is a real advantage to knowing two times more than the next best investor. For someone early in their career, what piece of advice would you give them to get to a position like you are in today? The first thing, honestly, is Dan, you're a beast. You're the former vice president of a $90,000,000,000 investment firm.
And today, you run your own firm called LeftLane Capital with over $2,000,000,000 in assets under management. For someone early in their career who might be listening to this, what piece of advice would you give them to get to a position like you are in today? I'd say it's really a couple things. I'd say the first thing, honestly, is pay attention to all of the little details, that are going on around you.
I think as I think about my road to Insight Partners where I started my career in venture, a number of steps along the way, I'd say each one of those steps required me to really pay attention to other people who previously were in my life and and who were able to to be successful to understand what worked and what didn't. I'll give one example from earlier on in in my life. I'm a venture capitalist now, but perhaps the earliest influence on me was one of my older sisters.
So grew up in Saint Louis. I had two older sisters, one of whom was nine years older than me. She's actually one of the world's leading scientists and doctors specifically around curing rare genetic diseases in small children. So you look at that and you think, okay, what does that have to do with anything that I'm doing now? Well, as I was growing up, I learned a couple of different things from her.
I'd say the first thing really that I learned was just the level of conviction and self belief it takes in order to do something that's generally pretty highly improbable. I'd say the second thing is just, frankly, hard work and a complete lack of shyness.
Like, if you're especially if you're looking to get into venture or get into something that is a competitive space, being willing to make yourself the expert or the greatest expert that you possibly can, learn everything around you, but then also reach out, get in front of people, and just have, frankly, the the extroversion and hustle and effort to just make it happen, I think, are probably the two biggest things.
When you're paying attention to the details of the most successful people on the planet and you study them, what are a few things that you've noticed that they all have in common? Very surprisingly is a level of humility and an understanding of the importance of context and the context you put yourself in relative to all of the things you're ultimately doing yourself. I remember about a decade ago, I had my, my final round interviews at Insight Partners for my first job in venture.
That point, I think Insight was on its eighth or its ninth fund. They had proven themselves to be an institution with real staying power. And I actually asked, managing partner, a man named Richard Wells was my last interview. I asked him. I was like, hey. Why have you all been so successful? And I expected to hear things around, oh, it's because we look at it this way or we understand this.
First thing he said was just, we ran we run a great race, and we were super intentional about the space that we wanted to play in. And understanding that you as good or as strong or as smart as you think you are, minding your context and actually actively managing that context, be it the industry you're going after, the problem you're trying to solve, the people you're surrounding yourself with is incredibly important.
And I think everybody that I talk to who's been super successful has really thought about it that way. The second thing that all of them have is a continually renewable source of self belief. You know, at this point, I've had the chance to work with almost a hundred different growth investments, venture investments between my time at Insight and and now my time at Leftlane.
All of them, even and especially the those that have gone on to very successful multibillion dollar exits for twelve, eighteen, twenty four months in each of those cases, there was a point where we didn't know if the business was ultimately going to exist. And the successful founders were the ones who were able to find that belief not just for themselves, but also for the entirety of their teams and be able to instill that through an organization.
So I think when you put those two things together, those are two of the most common themes, specifically within founders and people looking to start companies that I've seen be successful. You mentioned hustle. As much as it's talked about, I still think it's a little bit underrated. You did what I'll I believe a lot more people should do. So instead of going to an MBA, you kinda just jumped right into it. I think that if you wanna be successful as efficiently as possible, don't get an MBA.
Instead, I think you should learn from the most successful people in the world who are already in the position that you want to be in. And then go out, work for them, and take notes relentlessly for two years and figure out what do do they do differently, like you mentioned, that other people don't. And then just reverse engineer what they do into your own life and apply that. And by the way, you don't end up with hundreds of thousands of dollars in debt along the way.
But what do you think about, an MBA and going through that process? So I understand the argument against an MBA, particularly when you are earlier on in your career. I I agree with the thesis that getting practical hands on experience to the extent that you can, is ultimately going to trump anything you're going to be able to learn in a classroom.
And it also should, again, especially early in your career, be available to you now that there's more information available than ever for you to read, dig in on, make yourself an expert, and then work to get yourself in front of people who ultimately work with you. I do think the MBA certainly has a place. As I think about people who are mentors for me. I can think of one person, right out of college in in my BCG days. He was actually a former army combat engineer.
And so he spent the first eight years of of his career helping build bridges in Afghanistan. And so for somebody like him coming back and being able to say, okay. Now let me get the skills and let me spend two years of my life networking. I think there's value to it. But as you think about someone who's just starting out, I would really if you wanna be in business, really prioritize experience first. And you decide to leave in prioritize experience first.
And you decide to leave Insight to start your own firm with your, with Harley and Vinny. Why did you decide to leave Insight? And what was so special about LeftLane when you first started and and still is that led you to gain a competitive advantage against other VC firms in the space? Yeah. So Harley, Vinny, and Jason, Schiedler, who who joined us as well.
So I'd say the motivation behind it was a real conviction in the strategy that we were running and a desire to, frankly, build something ourselves. So Insight Partners, for for those listening who may not know, really successful growth equity, private equity, investment fund primarily focused on enterprise software over the last several decades. So that's where, all of my partners and I started our careers, in in venture. And Insight taught us a couple very important things.
I'd say, perhaps first and foremost, it was becoming an expert in your space and and on the investment thesis that you wanted to run down. Now for them, that was enterprise software, and they started doing this in the mid to late nineties. It was an amazing choice, an amazing race, and and they've run it particularly well. As I think about what our thesis has been over the course of our careers, it's been a little bit different. Right?
Which is, you know, if enterprise software, which is an asset class that so much of the industry has ultimately flocked to, It's been a great asset class because of a couple things. One, there have been technological tailwinds behind it. So you had, compute power move into the cloud, things move off premise. You had more and more companies building on top of of these software solutions so that you would end up with businesses who will be customers of Salesforce for as long as they exist. Right?
When we looked at our space, we saw a different technological tailwind and a much larger opportunity. So rather than focus on the, you know, couple hundred billion dollars a year of enterprise software spend, we turned our eyes towards the now $55,000,000,000,000 a year consumer market and market of consumer spend in the Western world. And we've seen a couple tailwinds that we think are actually even more transformational.
First and foremost, smartphone penetration dating back from, you know, late two thousands all the way through to to where we are today. That enabled a complete transformation of the way that consumers use the Internet. You know, it went from the place where you find a doctor's office, the place where you share photos of your friends, to now it's actually the place you go to the doctor. It's not where you find a tutor. It's the place where you receive the tutoring services.
So we saw this transformation where we thought Internet properties and things solving these really lifelong problems for consumers were both going to be more available than ever because of smartphone penetration. And then also, they were going to be able to capture more wallet share than ever because, again, there was just way more economics that were actually moving through the platforms as opposed to something that was going off platform. So we saw this thesis.
We saw a market where everybody was really focused in the venture world pretty purely on enterprise software. And so we thought there was an opportunity to to build an organization and a and a fund that was just dedicated to working with founders to solve these problems. It's a the the journey for m one finance, one of our first investments out of our our first fund at left lane relative to an enterprise software company is absolutely night and day.
And so if we we felt if we built a team, a network, resources, a thesis just around understanding that that we were gonna be able to stand out. And when you started your first fund, you raised $630,000,000 for that first fund. How many meetings did it take to get to that? Somewhere between 1,502,000. And what was your pitch? So the pitch the first part of the pitch was really exactly what I just laid out to you. It wasn't so much selling people on us. Although, at the time, I was 29.
The oldest of my partners was 30. So there was an element of establishing credibility. The pitch was first and foremost, no. You actually can build a huge business in in consumer, and you can do so in a way that is more reliable. Because if you think about limited partners, LPs, the people who invest in in our funds, they'd gone through this wave of social networks, let's say, where one out of every end social network going after a particular space was ultimately going to win.
They went through a wave of low repeat, low retention d to c brands, mattress brands, for example, which had astonishing growth, but then you had no repeat customers. And so, ultimately, there was real volatility. So the default assumption from so many people was that you just can't do this in consumer. Right? Like, this enterprise software is the only place you can run a sustainable venture playbook.
And so the pitch always started with that, with explaining the fact that there is a difference between good venture, investable consumer and consumer that really isn't venture investable. And that that thesis started with the same reason the folks at Insight loved enterprise and enterprise software which we learned from, starts with retention.
It starts with the fact that if you back companies that customers will be around for ten, fifteen, twenty years, this becomes the most important thing that they're using on a regular basis. They're going to stick around. And, I mean, I we've seen it, right, over the last half decade where we had people at home for COVID, usage of so many different tools and utilities spiked. You had, capital more available than ever before. You had that pull back a bit.
But if you look at a lot of the companies we work with, because these were the types of things that you don't cut when times get hard, that you really are building your life on top of, then all those consumers persisted. The companies or many of those consumers persisted. The companies are still doing great because of that resilience and that reliability.
So it was finding a way to both convince people that that was a viable strategy and then, of course, you know, convince people on a first time fund where we were going with the the super ambitious. We're raising trying to raise 500. We ended up raising $6.30, but convincing people to to make a bet on four relatively young people running an ambitious strategy. You mentioned your age. You're 29 years old. The oldest of your partners was 30.
I've noticed a couple of things about the age dynamic as a founder. I've noticed one, in podcasting or, I guess, in my instance, being young is definitely certainly helpful to opening up the door. Yeah. But on the contrary, in sales, I've noticed this this actually can be more of a negative than a positive. And the reason why is especially if you are building out a premium service offering and a premium product.
If you're trying to sell that offering about a similar price to somebody who might be, like, ten years older than you, People might question, like, hey. Why should I trust someone who's ten years younger to actually do this? For maybe founders who are also pretty young trying to combat that, what would you tell them? Make sure you understand what you're talking about. And then secondly, quickly adapt to the language that's already used by the people that you're trying to work with.
I think if you can, in the first minute of a conversation with somebody, if you can establish credibility with them about subject matter expertise in the content that you know, immediately, some of the age concerns vanish. The first I mentioned I was a strategy consultant. First thing I did out of, out of college, first project I worked on was working with steel manufacturing, where I was as a 22 year old who knew absolutely nothing about steel manufacturing.
I was working with people who'd been in the steel industry for three, four decades. And my job was, how can we convince them to do x, y, and z and and sort of achieve this strategic goal or identify it? And it was I was bad at the beginning. The first month, two months, it really struggled.
But once we were able to get to a point where it was understanding that language, understanding the lingo, knowing that the first two minutes of a conversation with somebody, that vertical takeoff is so important, if you can nail that, eventually, the the credibility concerns melt away, and you're speaking with somebody as a peer as opposed to somebody you're trying to impress. You mentioned the 1,500, meetings. I presume you've gotten hundreds of rejections through that. More than that.
Yeah. How do you deal with rejection? Keep going. I think you get the rejection. You get feedback. First thing we do, evaluate the feedback. Is it valid? Is it not valid? Are there is there some way we can objection field and and counter this or not? If so, we're gonna change the pitch a little bit. We'll change the messaging. We'll make sure we have additional materials to make sure that people get this specific point about what it is that we're doing. And if not, you know what?
We're just gonna keep going. I think that's one of the advantages, that I have frankly as a VC relative to somebody starting a company is I've had the chance to work with so many different founders and see such an extraordinary level of rejection that founders face as they as they start a company or start a career. It's the norm. It's just what is going to happen the vast majority of the time.
And so I think if you're gonna go start something knowing that's the case and how to use it effectively, let it roll off and keep going, super important. I was listening to one of your cofounder's interviews, Harley Miller, on '20 BC. And he said that to be successful early on in a fund, even if you're an associate, you have to think like an owner. How do you do that? It's a good question.
If you're thinking like an owner rather than thinking about how can you know, a typical thing we'll hear from somebody, you know, junior in venture. How can I get a deal done? How can I start building a track record? That drives great hustle and great drive. That's awesome. But it's not just how can I get deals done? It's how can I get the right deals done, and how can I have my these earliest seeds that I plant in the ground be an enormously positive part of of the track record?
Because the things that we were able to raise fund one of of of left lane on primarily were things that were done across the the group of our careers when we were associates, right, when we were sorted at that stage. You've invested in some pretty successful companies now, like m one finance, Spilt Rewards. What do you look for in the right deals? First and foremost, will this product become part of the operating system of a consumer's life?
So we are relentless at evaluating the customer's relationship with the product. We're looking for longevity. We're often and this is more of kind of our quantitative approach where we will almost every deal that we do, we will look at raw, anonymized, of course, but raw transaction data. So every transaction that that somebody's ever done. We'll also look at usage data. How often are you opening an app? How often are you, you know, if it's a savings app, checking your savings?
How often are you thinking about that? And we'll do surveys. We'll do all of this to put together a holistic view of, hey. Is this going to be a bedrock of somebody's life? Is it not gonna be a bedrock of somebody's life? And so that node is the first thing that we're really looking for. Does that exist or does that not? I think you'll hear different people who invest in consumer approach things differently. That really sits at the top for us.
And then, obviously, market, tailwinds, competitors, you'll sort of run everything through. But our thesis and our bet is that that node, that customer, product relationship is something that was under misunderstood, under understood, underanalyzed, and that there's real alpha if we're able to understand that better. And the other culture that you emphasized pretty, diligently at left lane is to promote from within. What does that mean, and why is it so important for your team?
It's really difficult to think like an owner if there's absolutely if there's very little chance or no belief that you can become one. I think that's one piece of it. The second piece of it is if we're going to invest as heavily in our culture as we do, super important to us that the people who join us around the table as partners be people who came through the ranks and and sort of rose through that culture.
So to that extent, you know, everybody who works at Left Line has long term incentives with the fund. Right? Has carry in the funds to make sure that they're fully aligned. We absolutely practice what we preach. One of our honestly, one of our proudest days is we had our first partner promotion, with Matt Miller joining us. He, you know, he was one of the absolute first people here at at left lane, started as a senior associate, rose the ranks all the way through.
We've got an incredibly deep, talented team as well where we're hopeful that, more people will join us, but it's super important to us. You've operated with a quite a bit of speed. This is something that I've noticed has been a consistent theme on our show. I interviewed this guy, which you might actually you might actually wanna speak to. His name is Zach Yadeghari. He's, 17. He's got a consumer app called Kallai. And what they do is they scan food with 93% accuracy.
It'll tell you, like, the calories and information and everything in in the meal. They do about 12,000,000 in ARR in high school. And, I asked him, why do you think you've been so successful? And he said, it distills down to one thing, because I operate with speed. When I decide to take action on something, build out a feature, start a company, build a product, I just do it.
And meanwhile, when our competitors decide that they might wanna do something similar, it took them three months to decide whether or not they should do it, and we're three months ahead. But I think there's the other side of it where I think if you operate too fast, where you're just doing things just because they pop in your mind and you're like, okay. Let me go do that now. You actually act more reckless.
Is there a right balance that you can create with acting fast, but also efficiently and being intentional about the decisions you make? It's a there's so many ways you could go with the speed conversation. I think to answer the question directly, there absolutely is, the right balance to solve. Where I've seen founders we've worked with building companies be successful with this, so they have a north star. The north star is usually oriented around the problem that they're ultimately solving.
And so if they know, for example, I recently led investment to a company called Rev AI, which is AI that helps body shops, collision shops repair the computers in your car as well. So if they know that the core problem statement is right now, you know, 80% of the time, certain shops aren't able to do certain repairs on on computers, which leads to a worse experience for everybody. That's the problem they're solving.
Then the product roadmap, let's figure out the best possible way to actually go solve that specific problem. If that's where we think the most economic value lies and where our greatest ability to grow is, then every piece of our product roadmap. We may try, you know, x, option of doing this or y option of doing this. But if that's the North Star, let's solve for that and oscillate within that.
We've seen a bit less success is where that North Star starts to move around and and the end problem that you're ultimately solving. But the the point around speed and the Cal AI story of, you know, I'm able to win because we go fast, Every investment, I think, in in just about any kind of firm that you're evaluating, there's always a really common question, which is, aren't the incumbents going to do this? Or isn't Amazon gonna do this? Isn't Apple gonna do this? Or somebody going to do this?
I worked with some, you know, large companies at BCG and saw attempts at large companies innovating. The fact that an exceptionally talented team, let's say, in fintech or wealth management, for example, can build a significant portion of a personal budgeting app in three months, test it, try it, To even get access to engineering resources at a large existing financial institution, that might take a year.
And then it's system and then there so I genuinely believe in kinda organizational in in large organizations having an endemic slowness to them where it's just difficult to steer the ship. And I think that that's not just an advantage that happened that a company enjoys when they're first starting out. It is something that DNA wise, if you can maintain it, is gonna give you an advantage throughout the entire building process.
And on the investing side, when you're sitting down looking at companies, you're looking at companies in new and totally different industries quite frequently, which means every two to eight weeks, you kinda have to become like a micro expert on that industry. What's the framework that you go through to understand as much as you can about an industry in a short and condensed period of time as possible? Start with the problem. How big is it? How painful is it at the customer level?
Look at the alternative solutions to the problem. Do I think this problem is going to be bigger or smaller in five years? How well does this company solve that problem? You know, one of the biggest draws of poor venture capital returns or biggest drivers of poor venture capital returns is when you are looking investing into things that look cool or feel cool but don't have same power and don't have that.
So being very problem centric when we're first trying to really understand a new space and and get up to speed. And you're also trying to spend you spend a lot of time trying to find under the radar companies. I think that's where a lot of the value creation can be found. What do you do to find companies that are under the radar, but also highly investable and great opportunities? The first and first and foremost is knowing what good looks like.
Especially at early stage of a company, what's something that has a high probability of of being good or is running a race that we think is ultimately good. And so that's when some of the things I talked about earlier around our strategy works because of high retention. Right? So if something we don't think something can have a ten year customer relationship, we're simply not going to back it. So taking all the opportunities, running it first through that filter.
And then from there, having a combination of an incredible team. I mean, we've got 24 people on our investment team whose job it is is to see every possible angle and every possible company. And I firmly believe we have a a wonderful data backbone that takes credit card data and all these different data sources, runs it through an AI engine, and helps find it.
I think when you're talking about the relationship that exists between a VC and a founder, that that sourcing absolutely has to be human led. And so we've got an incredible team whose job it is is to take all the signals and data that we have, add value in initial conversations with founders, build trust, and get to a point where, you know, ideally before other people are seeing it, we're able to to get in front of it. And then I'd say the a big part of that as well, just getting on a plane.
I think that's a huge part of our culture. I I think back to partner Vinny got married a couple years ago in in Southern California. And the Thursday before the Saturday wedding, one of our, we have a UK office. One of our London team members found an awesome deal in in Hamburg, Germany. He also actually came over for Vinny's wedding in Southern California. So Saturday is the wedding. The Thursday before, we're in a meeting. We see that this is potentially an incredible opportunity.
We're like, alright. That that Sunday, right after morning after the wedding, we hopped the flight to to Hamburg via at least one connection, and had a four hour standing meeting, quite literally standing because the CEO honestly, I think it was a test to see if we would ask to sit down, but we held through it, jet lagged, and all got through the four hour standing meeting and then moved on. Right? I think there's a there's a real element of that that's just core to the culture.
Yeah. I noticed that too because, last year, it was, like, during spring break. I was, like, I saw a conference that Jack Altman was speaking at in San Francisco. I was, like, oh, I should I should go out there and fly out there. Keep in mind, I've probably never flown out anywhere outside of Florida when I was, like, three or four years old in my life. So my parents were pretty hesitant. They're like, why? You don't need to get on the plane. I'm sure you could just email him.
And, like, no. I gotta go out and and try to see if I could strike up a conversation with him. I was walking to Chipotle to get lunch after one of the speakers was done speaking, and I see him coming out the back entrance. So I just walk up to him, like, hey, Jack. This is what I'm doing. Super generous with this time. Spent, like, three or four minutes talking to me. Didn't have to do that. Yeah. And at the end, I'm like, hey. We got the show. We'd love to have you on. He's like, yeah.
I got a baby coming up in a few months, but I'll do it after. I think just having those types of conversations and just getting on the plane, taking the train, going, taking the meeting, responding to that email, I think can be those micro differences and micro, I guess, decisions can be the thing that makes the difference between making it and not. I love the hustle, by the way. That's awesome. But we I mean, it's it's beyond just sort of that initial thing of of winning a deal.
There's also, look, the journey of a startup, as I mentioned earlier, is just never linear. Like, there's always going to be ups and downs and changes because it can take ten, twelve years to go from an investment to an exit. And so if the foundation of the relationship is built on, hey. No. We worked super hard. We came here face to face. We went to Germany or The Czech Republic or wherever, and we sat down. We had a meal.
When that trust is established from the beginning, it makes the the tough conversations that you're gonna have over a decade just much easier if that's the orientation from the get go. This is more general, but there are people in the audience who might be listening to this who are kinda following the things that you've mentioned. Maybe they're spending a lot of time grinding, hustling, getting on the plane, paying attention to all the micro details, but they still feel stuck.
How can someone who might be in that position get unstuck? There's two types of stuck. There's short term stuck and long term stuck. Short term stuck is maybe cheesy guys. Get outside. Go for a run. Go if you're in a city, go to a different neighborhood you don't normally spend time in. Maybe don't bring your phone. Don't look at it. Just remove yourself from the problem that you're ultimately trying to solve. Get some different experience or perspective even if it's only for a few minutes.
For me, it's running. I go over the the holidays. I was working on a particular problem. I I I live primarily in Chicago. I went for a run. It was 15 degrees outside. I didn't care about the weather. I responded and helped solve the problem after that. I'd say more more seriously and more long term. If you're feeling stuck, take a second and evaluate, like, what part of this do you feel stuck on? Is it is it a market and or problem issue?
In other words, is the track simply not long enough to run the race that you want to run, or is it too cluttered to run the race that you wanna run? Or are you feeling like you have some limitation that you can identify to say, hey. I'm not able to do this for x y z reason in which upskill. I think it's a matter of, really, for those longer term conversations, thinking about, is it there is it external? Is it internal? And then from there, working to to diagnose it.
I think that's a really good point. And throughout your time investing, you've been investing for nearly a decade now. What is the number one trait that makes a great investor? Yeah. Curiosity. Curiosity. I think that you need to when you're to your point, doing these two to eight week micros you know, sprints to become micro experts in a given field, there is there is a real advantage to knowing two times more than the next best investor knows or the next best person knows.
And so getting to a point where you have this deep endemic curiosity where you see a problem being solved, you need to understand where it is. That's gonna help you find better deals, win better deals. Importantly, you know, people VC, we talk a lot about doing the investment. As you're you know, I'm involved I've been involved with now 20 plus boards over the course of my career.
As you're a board member to and partner to founders, that curiosity alongside of them is also able to make you just a much better thought partner. And you're trying to become the best consumer investor and the best in your space. To do that, you also need the best team. How do you evaluate and distinguish a players between b players and c players? What what is so unique about them that you're able to see early on? Exactly why somebody is an a player, the spike that they have, that can differ.
We have some folks who are exceptional at networking. So they're able to meet everybody. They become a gravitational pull in this space. We have some folks who are exceptional one on one with founders, who are able to build trusted relationships, some who just analytically can see things ultimately in different ways. The underlying, commonalities that exist between all of them is an ownership mentality.
So really caring about what they do, thinking about the big picture, absolute just hunger and drive and continuing to push through things, and then empathy, honestly, and an understanding for the people that they're working with. So those three things underlie each of it, and then you have the specific skills. And so we'll we work with people. You know, I think we're very intentional when we hire people around the goal is, hey. We want you to become a partner here.
That's that's the goal that we have. So we'll work with people very explicitly on, hey. We need to work on this, or you did a great job here. Work on that. But those are some of the traits that we see really distinguish the a players from the from the b players. And we've talked a little bit about the companies that you've invested in over at Leftlane. If you had to start a company today, right now, what space would it be in and why? That's a great question.
I so for me, the thing I'm probably most interested in right now is the intersection between personal finance and AI. If you look at a lot of the deals that I've done or or worked on, just this idea of saving families and households money and helping people start businesses, finance businesses, and run businesses. Those are two of the themes that I think are kind of the the back room the backbone of my career as an investor so far.
And when I look at what we've solved so far, one, I think the issue of, okay, can, consumers, can small businesses get access to financial services? Simply bringing them online was a monstrous step. Right? And I think we've seen a lot of the benefits there. As I look at the limitations, though, of online but done by you, I think they're really clear.
Right now, there is so much information that consumers just don't know, unstructured information that consumers, small business owners don't know, don't have the time to know. Everyone else has has other things that they need to do. And the second, the process of actually using this information to do something with it is extraordinarily opaque.
Like, I I'm a cofounder of a $2,000,000,000 financial institution and bought a house recently, there were huge swaths of it that seemed esoteric, super complicated. Right? Both of those problems seem absolutely tailor made for for for AI to step in and and be able to make it easier for folks and sort sort of take us to the next generation of that.
I've seen the beginnings of some companies, I think, are interesting, but I think there's a decade long plus, tailwind behind that that's gonna just, frankly, improve outcomes for everybody involved. And we have a couple of closing questions that we like to wrap each interview up with. One is, if I slid you over a phone and you could call your 20 year old self Yeah. Would you call? And if so, what would you say? My 20 year old self would be really freaked out if you gotta call for somebody.
No. I so it's a good question. I would call my 20 year old self. I think the main thing that I would push that person to do is to just have far less fear or concern of the downside of interactions and conversations. Naturally, I'm a somewhat introverted person. And so I think if I could go back and just say, hey. Look. No. Go have that conversation. Right? Like, go get in front of that person. Take that initial step.
I think the earlier you can start to do that, the network effects in your life are just exponential and they compound. So I would really push people in that direction. And what's one rule that you live by that most people don't? One rule I live by that most people don't. It's the first time I really have to stop and and think about something.
Probably the biggest thing within venture at times, there can be a trade off between short term outcomes, short term success, and then long term reputationally. Right? Like, what are you ultimately working towards and building towards? I think one of the things I try to focus on is understanding that our goal and our ambition at LeftLion is to be successful for decades. Right?
And so when that's your orientation and that's what you're pushing on, then the way that you interact with founders, the way that you interact with other investors. You try to have that long term orientation. I think we emphasize that. I think you'll hear examples of other folks in the industry maybe not necessarily doing that, and that's one of the things we try to push on. One interesting answer I'll give you to that, question was also Zach.
I asked him the same thing, and he said he wants to constantly reinforce that he has full control on his life. And here's what he mean by means by that. When he got off the train he lives in Long Island. When he got off the train from Long Island to New York to the studio, there are a few different doors that he could go through. The shortest one is what or the one closest to the train is one pretty much everybody was going into. Made the most sense, most logical, etcetera. But he thought, hey.
If my life's a simulation, I'll walk through that door. But I wanna reinforce that I'm not in a simulation. So I'm gonna go to the door all the way on the left just because I can. And he does this, like, all the time. He'll make, like, micro decisions during the day.
Maybe instead of taking the shortest path to a destination, he'll spend an extra three minutes walking a totally different block that would take four or five minutes longer just because he wants to reinforce that he has full control on his life. So that, I thought, was a pretty interesting way to think about it.
So when I was younger, I actually would go through a somewhat similar exercise of thinking about, okay, well, probabilistically what path should I do and and was also somewhat focused on that. Then I had a kid, and I realized that I have very little control over certain parts of things. It went out the window when my son started walking and decided to try to throw himself off the back of my couch several times. Then you gotta be logical and be like, alright.
I I should probably do something here. Right? That that's when I realized, like, seeing a child go through a fascination of simply causing effects in life makes you understand that you really need to be prepared to stop the cause of various effects, come hell or high water. And to wrap it up here, what's one piece of advice you would give to somebody who's listening right now who seems who has seen what you've done and, also wants to be able to accomplish something similar?
With venture capital, the name of the game is finding deals. And so if you want to get into venture capital, act like you have the job now. I think that's a cliche that people use, but we've hired multiple people who got a foot in the door simply by sending us deals or sending us ideas, and ultimately getting in front of us. And so that is for VC, it's simple and super difficult. Get in front of great founders and bring us deals.
Yeah. And Jason Schuman from primary has a very interesting story along that path as well. He started a shoe business in college at U Miami. It didn't end up working out, but he moved out to Boston. And, he's like, hey. This venture capital thing seems pretty interesting, but, like, I don't know how to get a job in it. So he would start sending deals for free. This is before you could, you know, get commissioned or or be be a scout for a firm. He would send deals to VC firms in Boston for free.
But, you know, he still had to pay the bills, so he'd drive for Uber at night. And that's how he was able to get his first job in ventures because one of his passengers was actually a VC and was like, hey. You you should probably we should probably talk. Super interesting path. But I've noticed that one of the things he's told me and I've always kept in the back of my mind is if you can do the job before you get the job, then you can get the job.
A %. That's absolutely the right orientation, particularly when it comes to to venture. Well, I think that's a great way to end it. Thanks, Dan, for taking the time to join the show. I appreciate it. And if anyone's a founder, especially in consumer or in any of the areas that Leftlane invests in, feel free to take a look at their website in the episode description down below. And thanks for joining. Thanks, Simon. Appreciate it.