The Exchanges

Q But I want to start with a little bit on you. I mean, it's an incredible scaling story, so talk to me a little bit. How did you make your way into Venture? Talk to me, how did you come to found Left Lane in this incredibly fast and awesome ride that it's been so far?

A Specifically, how did I make my way into Venture? I kind of fell back asswards into it. I went to Wharton undergrad, 2007 to 2011. The compulsion or the status quo was for every Wharton Knight to go into an iBanking or consulting track, right? There wasn't this codified path for young adults. So you're right out of uni to go into venture capital or growth equity or private equity. That was a rarity. And there was this firm Insight Partners who was, I'd say, arguably the group that pioneered this concept of kind of an institutionalized analyst program. And I was highly entrepreneurial growing up. I had a lot of different companies and pursuits and hustles from Selling candy on the bus as an eight year old. Right. And, and with zero cogs, because my mother fueled my entire business until I got caught by the principal to starting more legitimate business throughout high school. And so coming into university and navigating that journey, it was very clear. I didn't want to do something that was the stereotypical track. I was always trying to swim a little bit against the grain. And so this firm insight was interviewing and I landed an interview and my interviews with insight, which I'm sure were less rigorous back then than they are now are comprehensive. Largely talked about the same things I talked about to get into Wharton, which were my entrepreneurial pursuits, kind of how I sa…

AI assessment note: “Specifically, how did I make my way into Venture? I kind of fell back asswards into it.”

Q Okay, so what have you recently changed your mind on, Harley?

A That we should do more media more often. There was some element of no one wanted to see four guys in their early thirties or at the time 30 raise a large inaugural fund. I think just emotionally, instinctually that rubbed a lot of people the wrong way or they perceived us to be Playing for something of getting rich off of fees or whatever it was, as opposed to objectively sizing us up and realizing, like, that was the asset class in which we were raised professionally that we best knew how to navigate, and anything but that would be counterproductive, and so I felt like doing media would draw attention and negatively bias that if people didn't want to root for our success, and I think that we've changed our tune there recently, case in point, with even wanting to finally be able to have the opportunity set to speak with you.

AI assessment note: “That we should do more media more often.”

Q I do want to ask you, when you think about like speed, speed of execution, winning deals, is Venture Today a game of picking or access, do you think?

A I would offer that those aren't the bookends. There's more convexity to it than that. There's other vectors and dimensions on which to play and on which to compete. I mean, listen, if picking is important, it's nothing without access. You could just sit there and put your finger in there and say like, oh, that company's going to be great. But like, if you can't get in touch or a founder doesn't buy in to your being a thought partner or a sounding board, then he or she, it doesn't matter. And then access, I think is, can be a bit overrated because you can figure out, you know, you can't teach picking. I think that's something that's innate and comes with pattern recognition. Access can be achieved in different ways, but I think honestly, the way that we strive to compete is on discoverability, right? And sourcing and of parsing and sifting through the sand to find that gem that no one else saw. A lot of the deals that we do are proprietary or bootstrap. They don't need money. They're profitable. Masterworks is a great example of that. There's plenty in our first fund and our second fund that behaved like that. And I think that's something we pride ourselves on. And again, the world, especially internet consumer technology world, which is where we focus exists outside of the coast, right? Every ecosystem is getting more and more robust. And I think we play there and spend a lot o…

AI assessment note: “I would offer that those aren't the bookends. There's more convexity to it”

Q I'm obviously a long-term believer in the power of media, so that makes me very happy to hear. Tell me, what's the secret to a happy relationship working with your bro?

A I'll start with the following. He's my best friend now and forever. We live together. I mean, really powerful thing. If harnessed the right way, and if boundaries are respected, which I think is first and foremost rule of thumb, second would be, let him be his own man. He needs to be, can't live in my shadow, empowering that and respecting that. And then ultimately, you have to treat him The same as anyone else, whether that be with positive reinforcement where deserved, and then harsh constructive criticism as appropriate, and make no mistake, I've towed that line appropriately over the last few years, and even predating our working together at Left Lane. And that was a thing. That was a real thing that people glommed onto, and they had to diligence it and get comfort with that, because it's not going to be neutral. It can't be neutral. It either is a negative, or it's a huge positive. And I think, suffice it to say, it's clearly Found its way into that, that latter camp, but that's not something you ever take for granted. You have to keep working at.

AI assessment note: “boundaries are respected, which I think is first and foremost rule of thumb”

Q How did that lead to left lane? Because it's a big move to start on your own and it's a massive thing to found your own firm. Talk to me, how did the founding of left lane come about?

A Early days with a lot of probably naivete and bravado, I was confident and was pretty decent at the role and at the job, right? Some of it was work ethic and input. Some of it was having a nose for markets, emerging markets before it was so apparent before it was obvious or an ability to have a resonance, mutual resonance with founders. And I was able to do a lot of deals and they were more internet consumer technology deals, which was not what the industry at large was focused on. It was very enterprise software or SaaS focused. And that wasn't where I really cut my teeth. I think there was something about sort of growing up in Pittsburgh, middle-class being deep into the bell curve of that common consumer. And I wore that on my sleeve that forgot other entrepreneurs that felt like that. And so that's where I carved out my own niche in practice and I became decently well-known in internet and consumer tech. I knew pretty early on that I felt like, okay, I could do this. I want to be a founder. But within a venture context, and the only way you do that is to start your own firm, build an institution of your own.

AI assessment note: “the only way you do that is to start your own firm, build an institution”

Q Can you do that same level of work in today's compressed fundraising timelines with soft banks, with tigers, with your crossovers, doing checks on coffee meetings? Are you still able to do your process to the quality and level that you need to?

A A hundred percent, and we never sacrifice on that. Well, one, first and foremost, we don't see those groups often or hardly ever. I think we're generally earlier by nine out of 10 times. We pride ourselves on being at the earliest semblance of product market fit. And then again, before it's obvious is when you strike, because when it's obvious, it tends to be expensive. And then you talked about, is that even possible in this environment? Listen, I think there are certain pockets of the world where an entrepreneur says, give me the money as fast as possible in the path of least resistance. And by and large, that's not a fit for us. I think we don't want to be passive like that, right? We want to put our name next to something. We want to spend the time. And spend the time to get to know someone before investing. Now that doesn't mean that can be speed dating and it's crash course work the way I, which I described. The trick is when you come at it with that contributory mentality, I don't want to say like bedside manner with a founder or a founding team, but it's that consultative sort of expectation management of this is not just for us to check the box. We're going to teach you things about your business in really short order that you didn't appreciate. And we won't be learning on the job, post diligence, post term sheet, post first board meeting. Like I see so many other firm…

AI assessment note: “A hundred percent, and we never sacrifice on that.”

Q I'm obviously a long-term believer in the power of media, so that makes me very happy to hear. Tell me, what's the secret to a happy relationship working with your bro?

A I'll start with the following. He's my best friend now and forever. We live together. I mean, really powerful thing. If harnessed the right way, and if boundaries are respected, which I think is first and foremost rule of thumb, second would be, let him be his own man. He needs to be, can't live in my shadow, empowering that and respecting that. And then ultimately, you have to treat him The same as anyone else, whether that be with positive reinforcement where deserved, and then harsh constructive criticism as appropriate, and make no mistake, I've towed that line appropriately over the last few years, and even predating our working together at Left Lane. And that was a thing. That was a real thing that people glommed onto, and they had to diligence it and get comfort with that, because it's not going to be neutral. It can't be neutral. It either is a negative, or it's a huge positive. And I think, suffice it to say, it's clearly Found its way into that, that latter camp, but that's not something you ever take for granted. You have to keep working at.

AI assessment note: “boundaries are respected... let him be his own man... treat him The same as anyone else”

Q But I want to start with a little bit on you. I mean, it's an incredible scaling story, so talk to me a little bit. How did you make your way into Venture? Talk to me, how did you come to found Left Lane in this incredibly fast and awesome ride that it's been so far?

A Specifically, how did I make my way into Venture? I kind of fell back asswards into it. I went to Wharton undergrad, 2007 to 2011. The compulsion or the status quo was for every Wharton Knight to go into an iBanking or consulting track, right? There wasn't this codified path for young adults. So you're right out of uni to go into venture capital or growth equity or private equity. That was a rarity. And there was this firm Insight Partners who was, I'd say, arguably the group that pioneered this concept of kind of an institutionalized analyst program. And I was highly entrepreneurial growing up. I had a lot of different companies and pursuits and hustles from Selling candy on the bus as an eight year old. Right. And, and with zero cogs, because my mother fueled my entire business until I got caught by the principal to starting more legitimate business throughout high school. And so coming into university and navigating that journey, it was very clear. I didn't want to do something that was the stereotypical track. I was always trying to swim a little bit against the grain. And so this firm insight was interviewing and I landed an interview and my interviews with insight, which I'm sure were less rigorous back then than they are now are comprehensive. Largely talked about the same things I talked about to get into Wharton, which were my entrepreneurial pursuits, kind of how I sa…

AI assessment note: “Specifically, how did I make my way into Venture? I kind of fell back”

Q What's the most memorable first founder meeting you've had? Mine was Johnny at Hopin. It was terrifying. He was like, we're going to build the fastest growing company in the world in 12 months. I was like, I'm in.

A So mine was probably two weeks in my job, June, 2010. I was meeting with Lukas and Koya of Lieferheld, which means delivery in German. This is the precursor to Delivery Hero before they acquired and expanded and merged with Online Pizza Norden and Niklas Osberg, the current CEO, to form Delivery Hero Holdings. So the company was principally in just the Dock region or in Germany at the time. I had obsessed, first week on the job, I looked at online education, online travel, and online food. Right, I was told not to, and that's where I spent my time, and so they happened to be in New York. I remember showing up to Soho House. Now I wear black, and people think I dress like a pirate, and that's just me, but at the time, I was dressing to the nines, right, with a A nice suit, a fish hook on my lapel, right, or something. I was trying to obfuscate my age, or my tenure, or lack thereof, and trying to be serious and not convey that I'd been on the job for all of 10 days. But they gave me the time of day, and I had spent enough time thinking through the space and had started a company actually in college in the mobile food. I had a native Blackberry app. It was way too fucking early, or it was just whatever. At least I could say I was just too early for the space. Reality is I didn't have the execution chops to see it all the way through. It was memorable and not in the sense that it w…

AI assessment note: “mine was probably two weeks in my job, June, 2010. I was meeting with Lukas”

Q How did that lead to left lane? Because it's a big move to start on your own and it's a massive thing to found your own firm. Talk to me, how did the founding of left lane come about?

A Early days with a lot of probably naivete and bravado, I was confident and was pretty decent at the role and at the job, right? Some of it was work ethic and input. Some of it was having a nose for markets, emerging markets before it was so apparent before it was obvious or an ability to have a resonance, mutual resonance with founders. And I was able to do a lot of deals and they were more internet consumer technology deals, which was not what the industry at large was focused on. It was very enterprise software or SaaS focused. And that wasn't where I really cut my teeth. I think there was something about sort of growing up in Pittsburgh, middle-class being deep into the bell curve of that common consumer. And I wore that on my sleeve that forgot other entrepreneurs that felt like that. And so that's where I carved out my own niche in practice and I became decently well-known in internet and consumer tech. I knew pretty early on that I felt like, okay, I could do this. I want to be a founder. But within a venture context, and the only way you do that is to start your own firm, build an institution of your own.

AI assessment note: “the only way you do that is to start your own firm”

Q Can you do that same level of work in today's compressed fundraising timelines with soft banks, with tigers, with your crossovers, doing checks on coffee meetings? Are you still able to do your process to the quality and level that you need to?

A A hundred percent, and we never sacrifice on that. Well, one, first and foremost, we don't see those groups often or hardly ever. I think we're generally earlier by nine out of 10 times. We pride ourselves on being at the earliest semblance of product market fit. And then again, before it's obvious is when you strike, because when it's obvious, it tends to be expensive. And then you talked about, is that even possible in this environment? Listen, I think there are certain pockets of the world where an entrepreneur says, give me the money as fast as possible in the path of least resistance. And by and large, that's not a fit for us. I think we don't want to be passive like that, right? We want to put our name next to something. We want to spend the time. And spend the time to get to know someone before investing. Now that doesn't mean that can be speed dating and it's crash course work the way I, which I described. The trick is when you come at it with that contributory mentality, I don't want to say like bedside manner with a founder or a founding team, but it's that consultative sort of expectation management of this is not just for us to check the box. We're going to teach you things about your business in really short order that you didn't appreciate. And we won't be learning on the job, post diligence, post term sheet, post first board meeting. Like I see so many other firm…

AI assessment note: “A hundred percent, and we never sacrifice on that.”

Q the team bringing you deals, wanting to do deals. And the truth is, I'm slammed today. I've got board meetings all afternoon. Tomorrow's even worse. I can do Thursday. And that's a bottleneck. If we're trying to do a great deal, if we're trying to do something and move fast, I am holding the team up now. How do you prevent yourself from being the bottleneck to great people pushing?

A I literally take myself out of the equation. One, if it requires the immediacy with which we need to respond now, it doesn't matter whether we need to speak at seven in the morning or at 11 p.m. at night, we will create that space for us to do that. Privileged to have three other managing partners and a lot of other great senior folks at left lane who do deals and do them incredibly well. So I'm by definition, not the bottleneck. There's a lot of latitude and surface area in sort of different permutations of how a deal could get done. And then ultimately the way that we scale, like our fund size grew. We just closed our second fund very recently at 1.4 billion from our first fund, six hundred thirty million, which I'm tremendously proud of. And that was again, a lot of pounding pavement, a lot of groundwork and ground game laid over Over the last couple of years, but it's not like we're going to all of a sudden start doing investments that are double or triple the size, right? We want to keep doing more of the same. And the only way to do that is to provide the leverage for yourself and your partners organizationally, which means get people up the curve quickly, drive that upward career mobility, make sure that people at a young age get the reps and exposure to do deals. Sure. They will make mistakes. They will have their successes. You have to be that sounding board and though…

AI assessment note: “I literally take myself out of the equation.”

Q boom, that was like gold dust. Final one, and I'm super excited for this. I'm actually changing it because I'm more interested by this one, actually, which is your ambition is, is incredible. It's very tangible. You feel it when you talk. Man, what do you want to build with Left Left Lane. In 3040 years time, grandchildren running around. What does Left Lane look like? What have you built?

A I don't have a crystal ball to say this will be the size or this is where we'll play. It'll be a lot larger than it is today. It will have cultivated some of the world's foremost investment professionals in the internet consumer space. And we will evolve. We will iterate as long as humans walk and grace this earth and need to eat and sleep and learn and keep learning and manage. Like everything that's fundamental theme and condition, we will be highly relevant. And we wanted to find that space, and so when people think about what is greatness there, our name will be synonymous with that. We will grow. We will have global presence. We already have global presence across Brooklyn, New York, our headquarters, and our London office, right? And this needs to be, it must be a firm. I will work for the next 3040 years, or as long as I have a sound mind, body, and spirit, but this will be a firm that transcends that, that withstands the test of time, you know, long after I'm gone.

AI assessment note: “this will be a firm that transcends that, that withstands the test of time”

Q the team bringing you deals, wanting to do deals. And the truth is, I'm slammed today. I've got board meetings all afternoon. Tomorrow's even worse. I can do Thursday. And that's a bottleneck. If we're trying to do a great deal, if we're trying to do something and move fast, I am holding the team up now. How do you prevent yourself from being the bottleneck to great people pushing?

A I literally take myself out of the equation. One, if it requires the immediacy with which we need to respond now, it doesn't matter whether we need to speak at seven in the morning or at 11 p.m. at night, we will create that space for us to do that. Privileged to have three other managing partners and a lot of other great senior folks at left lane who do deals and do them incredibly well. So I'm by definition, not the bottleneck. There's a lot of latitude and surface area in sort of different permutations of how a deal could get done. And then ultimately the way that we scale, like our fund size grew. We just closed our second fund very recently at 1.4 billion from our first fund, six hundred thirty million, which I'm tremendously proud of. And that was again, a lot of pounding pavement, a lot of groundwork and ground game laid over Over the last couple of years, but it's not like we're going to all of a sudden start doing investments that are double or triple the size, right? We want to keep doing more of the same. And the only way to do that is to provide the leverage for yourself and your partners organizationally, which means get people up the curve quickly, drive that upward career mobility, make sure that people at a young age get the reps and exposure to do deals. Sure. They will make mistakes. They will have their successes. You have to be that sounding board and though…

AI assessment note: “I literally take myself out of the equation.”

Q time, it takes huge amounts of energy, and then in the majority of cases, they churn out and leave you to go join another firm and take everything that you've given them, and so I'm like, nope, I want check writers, I want people that come in, give me leverage, and let's fucking roll. Why am I wrong? Why to you was building this model and this team so important?

A There's the cliche answers of it's the lifeblood of the firm, or all that, Which for what it's worth is true. I sort of just touched on it anecdotally of as the firm and the fund size or AUM grows and the deal count gets wider, right? We do more deals per fund as opposed to the same number of deals, but we drift into a different asset class. By definition, you need to have more people. So if one provides a space at the top for other people to climb the ranks and make partner and stay, and we want people to come in and build them from the ground up. It's something that we invest heavily into the training. From the outset, before you're allowed to get on the phone with entrepreneurs, and we probably speak with a thousand companies per month, right? Really rigorous, robust sourcing. So the best learning curve for a young, early, mid-twenty-something is to get that level of repetition, right, of putting the reps there, and all of a sudden they became really dangerous in the field, and I think one of our mantras is don't consume. If you're a consumer, no one's going to take you seriously. You need to be contributory in everything that you do and respect that bilateral value exchange, right? You give something to get something, and if that's Means you have a good comportment and temperament. You have something to offer a founder. I don't mean in the business of horse trading informat…

AI assessment note: “we want people to come in and build them from the ground up”

Q What's the most memorable first founder meeting you've had? Mine was Johnny at Hopin. It was terrifying. He was like, we're going to build the fastest growing company in the world in 12 months. I was like, I'm in.

A So mine was probably two weeks in my job, June, 2010. I was meeting with Lukas and Koya of Lieferheld, which means delivery in German. This is the precursor to Delivery Hero before they acquired and expanded and merged with Online Pizza Norden and Niklas Osberg, the current CEO, to form Delivery Hero Holdings. So the company was principally in just the Dock region or in Germany at the time. I had obsessed, first week on the job, I looked at online education, online travel, and online food. Right, I was told not to, and that's where I spent my time, and so they happened to be in New York. I remember showing up to Soho House. Now I wear black, and people think I dress like a pirate, and that's just me, but at the time, I was dressing to the nines, right, with a A nice suit, a fish hook on my lapel, right, or something. I was trying to obfuscate my age, or my tenure, or lack thereof, and trying to be serious and not convey that I'd been on the job for all of 10 days. But they gave me the time of day, and I had spent enough time thinking through the space and had started a company actually in college in the mobile food. I had a native Blackberry app. It was way too fucking early, or it was just whatever. At least I could say I was just too early for the space. Reality is I didn't have the execution chops to see it all the way through. It was memorable and not in the sense that it w…

AI assessment note: “mine was probably two weeks in my job, June, 2010. I was meeting with Lukas”

Q and he said Harley was unique in many ways, but he was unique in his, in The enthusiasm and confidence with which he would bring deals to the table, even in the earliest of days. Now, clearly you excelled in an exceptional way in rate. My question to you is, when you look at younger investors today, how would you advise them on scaling their careers internally within large funds?

A It's not just get deals done. It can't be that. It can never be that. That proverbial one-way option where you credit monger if it's great, And you parry it off and say, well, the buck didn't stop with me. There are quite literally this concept of supervisors, which is what managing partners are. Even if someone else is a partner, right, or a senior invest professional, if there is someone above them to say yay or nay, or sort of bless that, even if they're not principally involved in decision-making or management thereafter, you as a junior or mid-level person are able to parry that off and sort of suggest that it didn't go, it went wrong for X, Y, Z reasons, or it wasn't purely you who was putting it all on the line there. So it can't just be that you have to Think like an owner at all times, even if yourself are not principally an owner, you're still early in your career. Talk about finding that conviction, but you have to be a strong and original thinker. More so than conviction, it's about being an original thinker and being resolute in those beliefs, and then working to pressure test and substantiate that with a very cogent argumentation with facts and data, especially if people aren't seeing eye to eye with you, are not aligned with you. You can't just kill them with persistence or perseverance or with kindness. You have to kill people with substance. Proverbially, as fa…

AI assessment note: “you have to Think like an owner at all times”

Q as much first, and it's not the hundred true fans or thousand true fans. One, and then two, CACs are not the same, and so if you take the predictive assumption that it's going to continue being this customer acquisition cost for In perpetuity. There's not reality. So that's my challenge with the variability of both. Can you just help me actually investing wise? How should I think about that?

A Yeah. In internet consumer, right? Not all revenue is created equal. I think there's something nicely codified about enterprise software. Everyone has a principally similar spreadsheet. You can kind of put it in, you get this magic number, which seemingly governs and dictates the entire industry at large, which went a little bit bananas over the last Half a decade or in specifically the last couple of years, it's now retreated clearly, but a hundred times ARR was like the new norm or that was considered fair or cheap. And everyone was doing that. In internet consumer, you have a huge range of multiples, right? And you have to understand and appreciate that not all revenue is created equal. There's different margin profiles, retention profiles, so many different more kinks in the conversion funnel. So you have to be able to look into these second and third order derivative layers that inform sort of unit economics. There is no standardized playbook or a button that you can push to kind of Assertain economics or other surplus economics. Will this break in the right way? In the wrong way? Will this hold? There's so much more variability, and I think it can never be plugged into a spreadsheet with like a thumbs up or thumbs out. That just will be definitionally impossible in consumer, but to the extent anyone has, I don't want to say automated, but has streamlined that process in b…

AI assessment note: “There's different margin profiles, retention profiles, so many different more kinks in the conversion funnel.”

Q but it was actually when I spoke to Scott at Masterworks, one of your founders, he said that it's your speed of execution that is everything, and just unparalleled compared to anyone else. My question first is, How do you determine the things to go really fast on and where speed of execution is key versus actually we do it slow and we're very tempered in how we do it?

A Some comments. First and foremost, let it go on the record. I don't want going fast or moving with serious pace to be conflated for recklessness or lack of comprehension or diligence, right? One of our core mantras here at Left Lane is that they need not, they must not be a trade-off. You have to move with real pace and speed, but Not at the expense of execution and diligence. Oftentimes, one gives in this world, and I think we've architected a practice to be able to do both, and it's how we train our people. Every single person that works with us at Left Land on the investment team is trained on how to use SQL, how to use Alteryx. They can cut through raw data. It allows them to be really dangerous in the field with entrepreneurs and cut right to the heart of what you need to believe, and again, that's a two-way street. A founder or a founding team needs to be able to match that tempo. If you're just driving really fast as the investor without Visibility into where you're going. That is reckless. I think decision-making is critically important. To kind of give you the bit of the story, right, as opposed to the theory behind Masterworks, that deal was proprietary. He wasn't out in market in earnest. This was last summer, July or thereabout of, you have, you have, you have, you have, we dropped everything. We canceled our vacations in sort of early August to drive at this deal b…

AI assessment note: “One of our core mantras here at Left Lane is that they need not”

Q Speaking of kind of team members bringing investments to the table and the decision making that comes, you had a canvas that was blank when you started Left Lane in terms of how you structured decision making. How did you think about taking the lessons that you'd learned and optimizing your decision making at Left Lane? How do you structure it, and why is it that way?

A I won't go into like the ins and outs of our decision making process. I think there's a mechanical way, which is there's an investment committee of the four managing partners, right? And it needs to be a certain ratio. And I think we strive for simplicity there. I think in practice, it's about accountability and sponsorship and true ownership, whether that's one of the partners, whether that's one of the other senior members or even mid-level people who really want to step up and swing the bat. I am in the business as a founding managing partner and CEO. Sure. I do deals and I do a lot of deals that will always be a part of my job. It's a muscle that if I ever have to stop exercising, I will go insane because it's arguably what I grew up with professionally. It's what I love, but I've now also had to be in the business of rewarding conviction. And I think you have this natural tension from a decision-making standpoint of junior investment professionals who are pushing up to do deals. And sometimes with that sort of proverbial perceived one-way option, right? If it goes well, it's great. If it doesn't go well, I sort of get to brush it off. And you have the senior partners pushing down to do good deals. And it's that in the middle point where that healthy Tension, right? And that sort of sparring partnership, that dance that occurs is where magic happens. I think that's cultural…

AI assessment note: “there's an investment committee of the four managing partners, right?”

Q Man, I would love to see the conversation with your mom. How many times did you buy HelloFresh? What did you order this week? Have you bought it much this month? How did your friends buy it? Oh, lovely to see you too, Harley.

A Yeah, yeah, I mean, something along those lines, right? So, Again, if you knew my mother, she's world-class human. I mean, truly, like universally, I think what she's taught me is how do you have the surface area and range to connect with people and have that fundamental respect for the human condition. I think that's actually what has made me earnestly a good investor and someone that can connect with founders, right? And not just a founder that's intense in the conventional sense or ambitious in that conventional sense. I think you have to be able to have different speeds, different tempos, and that's ultimately from her. And so most of my conversation talks about Just being a better human, which I think in turn makes me a better investor.

AI assessment note: “most of my conversation talks about Just being a better human”

Q as much first, and it's not the hundred true fans or thousand true fans. One, and then two, CACs are not the same, and so if you take the predictive assumption that it's going to continue being this customer acquisition cost for In perpetuity. There's not reality. So that's my challenge with the variability of both. Can you just help me actually investing wise? How should I think about that?

A Yeah. In internet consumer, right? Not all revenue is created equal. I think there's something nicely codified about enterprise software. Everyone has a principally similar spreadsheet. You can kind of put it in, you get this magic number, which seemingly governs and dictates the entire industry at large, which went a little bit bananas over the last Half a decade or in specifically the last couple of years, it's now retreated clearly, but a hundred times ARR was like the new norm or that was considered fair or cheap. And everyone was doing that. In internet consumer, you have a huge range of multiples, right? And you have to understand and appreciate that not all revenue is created equal. There's different margin profiles, retention profiles, so many different more kinks in the conversion funnel. So you have to be able to look into these second and third order derivative layers that inform sort of unit economics. There is no standardized playbook or a button that you can push to kind of Assertain economics or other surplus economics. Will this break in the right way? In the wrong way? Will this hold? There's so much more variability, and I think it can never be plugged into a spreadsheet with like a thumbs up or thumbs out. That just will be definitionally impossible in consumer, but to the extent anyone has, I don't want to say automated, but has streamlined that process in b…

AI assessment note: “not all revenue is created equal. There's different margin profiles, retention profiles”

Q Man, I would love to see the conversation with your mom. How many times did you buy HelloFresh? What did you order this week? Have you bought it much this month? How did your friends buy it? Oh, lovely to see you too, Harley.

A Yeah, yeah, I mean, something along those lines, right? So, Again, if you knew my mother, she's world-class human. I mean, truly, like universally, I think what she's taught me is how do you have the surface area and range to connect with people and have that fundamental respect for the human condition. I think that's actually what has made me earnestly a good investor and someone that can connect with founders, right? And not just a founder that's intense in the conventional sense or ambitious in that conventional sense. I think you have to be able to have different speeds, different tempos, and that's ultimately from her. And so most of my conversation talks about Just being a better human, which I think in turn makes me a better investor.

AI assessment note: “most of my conversation talks about Just being a better human”

Q Can you give me an example where you've gained conviction super, super fast from meeting one or the first couple of days, and then one where it took actually quite a lot more time, quite a lot more work, maybe months. Maybe even years. Maybe you passed on the first round and did the second. Can you provide an example of each?

A In general, I feel like I know within five or 10 minutes of meeting an entrepreneur, whether I would work with him or her. It's something instinctual about that, and then in a way, I start to work backwards to pressure test those assumptions of, is this the right race? Is this a worthwhile race, meaning the space that you're playing in? Is this the right horse or jockey or team to bet on? I mean, that's the calculus constantly. I think there's been times in my career where I've probably been impetuous, right, and rash. Jumped to conclusions about this is a deal I want to do. I can talk about deals where it was certainly wasn't obvious, right? I remember pounding my fist to, to invest in HelloFresh and still not too shabby at a ten billion dollar market cap, right? It was a lot more six months ago, but nonetheless, it's company and it was space that was still nascent. And a lot of people that I would talk to about it dismissed it as, you know, mate, you're out of touch. Like no one cooks anymore. I was like, wow. Okay. Let me go talk to my family and friends in the suburbs of Pittsburgh or other parts of the middle of the country. For whom it's an incredibly powerful product. They live and swear by it and use it a handful of times a week for months on end and years on end. My parents were actually early customers of HelloFresh and that customer ethnography is I think about innat…

AI assessment note: “I can talk about deals where it was certainly wasn't obvious, right? I remember pounding my fist to, to invest in HelloFresh”

Q Can you give me an example where you've gained conviction super, super fast from meeting one or the first couple of days, and then one where it took actually quite a lot more time, quite a lot more work, maybe months. Maybe even years. Maybe you passed on the first round and did the second. Can you provide an example of each?

A In general, I feel like I know within five or 10 minutes of meeting an entrepreneur, whether I would work with him or her. It's something instinctual about that, and then in a way, I start to work backwards to pressure test those assumptions of, is this the right race? Is this a worthwhile race, meaning the space that you're playing in? Is this the right horse or jockey or team to bet on? I mean, that's the calculus constantly. I think there's been times in my career where I've probably been impetuous, right, and rash. Jumped to conclusions about this is a deal I want to do. I can talk about deals where it was certainly wasn't obvious, right? I remember pounding my fist to, to invest in HelloFresh and still not too shabby at a ten billion dollar market cap, right? It was a lot more six months ago, but nonetheless, it's company and it was space that was still nascent. And a lot of people that I would talk to about it dismissed it as, you know, mate, you're out of touch. Like no one cooks anymore. I was like, wow. Okay. Let me go talk to my family and friends in the suburbs of Pittsburgh or other parts of the middle of the country. For whom it's an incredibly powerful product. They live and swear by it and use it a handful of times a week for months on end and years on end. My parents were actually early customers of HelloFresh and that customer ethnography is I think about innat…

AI assessment note: “I remember pounding my fist to, to invest in HelloFresh”

Q you're looking at security or login enterprise software, where you're like, okay, where's this the eighth Ten billion dollar. And so what I find is the price sensitivity on consumer deals is much less because the upside scenario planning in a lot of people's heads is so much more. How do you think about your own price sensitivity today? And have you had some big lessons on it over time?

A I'll offer a couple of things. One, I think the challenge and the pushback I always received was that, no, this is too early or it's too variable or unpredictable. And I would challenge that somewhat instinctually of understanding the actual underlying inputs and mechanics and drivers. How can you actually take growth equity, analytical rigor and sort of principles and frameworks and apply that earlier stage in internet consumer tech? The simple answer is there's lots of littles, right? Even a company at a nascent stage of a million or two million dollars of annualized revenue is probably thousands or tens of thousands of customers that have purchased a product, used it, liked it or not, taken out their wallet and come back. All the hallmarks of product market fit can actually be ascertained and deduced at a much earlier point in that company's evolution as compared to a infrastructure software enterprise security company that it's at a Million of ARR with half a dozen or a dozen customers, half of which are pilots or introductions from their, their seed network. And like, it's just not predictive. And so that was the mantra of, can we apply growth equity principles, but in a venture context in the internet consumer? So minimize downside, have the same sort of proverbial hit rate as you would have or expect to have in growth equity, but at the cost basis and entry point of vent…

AI assessment note: “can we apply growth equity principles, but in a venture context in the internet consumer?”

Q but it was actually when I spoke to Scott at Masterworks, one of your founders, he said that it's your speed of execution that is everything, and just unparalleled compared to anyone else. My question first is, How do you determine the things to go really fast on and where speed of execution is key versus actually we do it slow and we're very tempered in how we do it?

A Some comments. First and foremost, let it go on the record. I don't want going fast or moving with serious pace to be conflated for recklessness or lack of comprehension or diligence, right? One of our core mantras here at Left Lane is that they need not, they must not be a trade-off. You have to move with real pace and speed, but Not at the expense of execution and diligence. Oftentimes, one gives in this world, and I think we've architected a practice to be able to do both, and it's how we train our people. Every single person that works with us at Left Land on the investment team is trained on how to use SQL, how to use Alteryx. They can cut through raw data. It allows them to be really dangerous in the field with entrepreneurs and cut right to the heart of what you need to believe, and again, that's a two-way street. A founder or a founding team needs to be able to match that tempo. If you're just driving really fast as the investor without Visibility into where you're going. That is reckless. I think decision-making is critically important. To kind of give you the bit of the story, right, as opposed to the theory behind Masterworks, that deal was proprietary. He wasn't out in market in earnest. This was last summer, July or thereabout of, you have, you have, you have, you have, we dropped everything. We canceled our vacations in sort of early August to drive at this deal b…

AI assessment note: “they need not, they must not be a trade-off”

Q you're looking at security or login enterprise software, where you're like, okay, where's this the eighth Ten billion dollar. And so what I find is the price sensitivity on consumer deals is much less because the upside scenario planning in a lot of people's heads is so much more. How do you think about your own price sensitivity today? And have you had some big lessons on it over time?

A I'll offer a couple of things. One, I think the challenge and the pushback I always received was that, no, this is too early or it's too variable or unpredictable. And I would challenge that somewhat instinctually of understanding the actual underlying inputs and mechanics and drivers. How can you actually take growth equity, analytical rigor and sort of principles and frameworks and apply that earlier stage in internet consumer tech? The simple answer is there's lots of littles, right? Even a company at a nascent stage of a million or two million dollars of annualized revenue is probably thousands or tens of thousands of customers that have purchased a product, used it, liked it or not, taken out their wallet and come back. All the hallmarks of product market fit can actually be ascertained and deduced at a much earlier point in that company's evolution as compared to a infrastructure software enterprise security company that it's at a Million of ARR with half a dozen or a dozen customers, half of which are pilots or introductions from their, their seed network. And like, it's just not predictive. And so that was the mantra of, can we apply growth equity principles, but in a venture context in the internet consumer? So minimize downside, have the same sort of proverbial hit rate as you would have or expect to have in growth equity, but at the cost basis and entry point of vent…

AI assessment note: “at the cost basis and entry point of venture.”

Q Speaking of kind of team members bringing investments to the table and the decision making that comes, you had a canvas that was blank when you started Left Lane in terms of how you structured decision making. How did you think about taking the lessons that you'd learned and optimizing your decision making at Left Lane? How do you structure it, and why is it that way?

A I won't go into like the ins and outs of our decision making process. I think there's a mechanical way, which is there's an investment committee of the four managing partners, right? And it needs to be a certain ratio. And I think we strive for simplicity there. I think in practice, it's about accountability and sponsorship and true ownership, whether that's one of the partners, whether that's one of the other senior members or even mid-level people who really want to step up and swing the bat. I am in the business as a founding managing partner and CEO. Sure. I do deals and I do a lot of deals that will always be a part of my job. It's a muscle that if I ever have to stop exercising, I will go insane because it's arguably what I grew up with professionally. It's what I love, but I've now also had to be in the business of rewarding conviction. And I think you have this natural tension from a decision-making standpoint of junior investment professionals who are pushing up to do deals. And sometimes with that sort of proverbial perceived one-way option, right? If it goes well, it's great. If it doesn't go well, I sort of get to brush it off. And you have the senior partners pushing down to do good deals. And it's that in the middle point where that healthy Tension, right? And that sort of sparring partnership, that dance that occurs is where magic happens. I think that's cultural…

AI assessment note: “I won't go into like the ins and outs of our decision making process.”

Q Incredible, by the way. But for me, I'm obviously a massive nerd on, like, Portfolio mechanics and portfolio construction. You said there about not, like, writing larger checks later, actually just doing more deals. Talk to me, how does it change the portfolio construction from fund one to fund two? And with the increased levels of diversification, if you're not writing the bigger checks, does that not mean compressed multiples?

A No, so I think in our first fund, again, we adhered to exactly as we said we would. We lead deals, we'll position build into those winners, and we have outsized ownership. I think when I came to the ranks at my previous firm, It was a much bigger fund. And so you were somewhat irrelevant if you couldn't produce large capital gains outcomes. And so no one got excited about our writing a ten million dollar check into something, but we're able to do that and achieve good ownership out of the gate and then stay the course and earn the right, coupled with the company doing well, but earn the right with a founder or a founding team to double down and lead or co-lead a subsequent round and really build that outsized ownership and then have big outcomes into companies that are multi-billionaire outcomes. That's how you really move the needle, even in a large fund.

AI assessment note: “No, so I think in our first fund, again, we adhered to exactly as”