Adrian Fortino, Venture Capitalist & Entrepreneur, Joins The Herd Has Spoken

Venture Capitalist & Entrepreneur -- Arian Fortino

Adrian Fortino is an early-stage technology investor, entrepreneur, and a pioneer in the ridesharing space. Adrian is Managing Director at Mercury Fund, an early-stage technology Venture Capital firm. He is an educator, mentor, and someone who loves competition. He’s known for working his ass off constantly and is not content until completion. In this episode, Brad and Adrian dig really deep into what it takes to become a successful entrepreneur.

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Enjoy the conversation between Adrian and Brad

Brad  
You and I have known each other for a number of years, across a lot of your pursuits. And they’re worth noting, I guess, right from right from the beginning, as an entrepreneur, as an investor. As now I will say a professor, you might say the lecturer at the University of Michigan. So obviously an accomplished guy to me, you're just Adrian. But But one of the things I've come to appreciate so much about you is your your love of tradition. So you have a fantastic post Christmas party every year, which we can get into you've hosted flag football game until, you know, our collective knees expired on an annual basis. And you're sort of one of those people that finds ways to get people together on a regular basis. So I'd love to kind of kick off by asking you why is it that tradition is so important to you?

Adrian  
It's it well, thanks for having me, Brad. First, it's good to see you, my friend. It's a great question. And it's one that I don't actually I've never thought about before, but I'll try to you know, come up with something, you know that that. But I feel like I don't know. I'm a very nostalgic person. I've always been a very nostalgic person. And I guess I feel like and I and I also am incredibly sort of community focused and community driven. I think that probably comes from a few things like I grew up in a very small town in the middle of Michigan, right, Elma Michigan, town of like, when I was there, 10,000 people, right, so everybody, you know, everybody knew everybody. And I think that there's something to that, that I sort of strive to, to build community and build relationships, kind of in, in all walks of, of my life. And I think there's nothing to me, there's nothing more important than building genuine relationships with people, right? But

Brad  
I want to I want to come I want to come back to you know, your, your childhood and dig more into this. But you know, and we'll and we'll talk about a lot of what you're doing now, but I want to just butt in for a second here. And say that when people typically think of venture capitalists, which which you are and you work for a very well respected organization, Mercury fund, and they don't usually think about community built community builders, right? And so how do you how do you mentally think about that, where as a, as a venture capitalist, you have to be pretty damn focused at providing returns to your investors. And yet, you've obviously garnered a tremendous amount of success by caring so much about those around you, and community. And I think that's a tough thing for a lot of us to wrap our, our heads around. So how do those come together?

Adrian  
Yeah, it's a great question. So look, I am a founder first, right? When I think about myself in if I how I would identify, identify as a founder operator first, that's, that's that was my first entree into anything, startup community, anything around that. And I am, I am a venture capitalist, you know, now, and that's what I do is my, you know, full time, you know, occupation, and I enjoy it a great deal. But that doesn't mean that I don't still have you know, my philosophy or my kind of, you know, the way that I that what drives me is is still building community and, and so, it is something that I've always been passionate about, in fact, some some friends from Ann Arbor, you know, remember like, once I got back from from going to California all the time, you know, I got back and this is in southern Ohio ended, ended 12 something like that. And I saw that there were a lot of people sort of, on their own doing their own you know, startup like what Their own startup journey, you know, but almost in their own, you know, worlds right. And, and I kind of saw that. And I knew what was happening having been in the Bay Area and how much more conductivity there was about founders kind of relying on other founders to get through difficult situations. And so as I saw that, I was like, man, I gotta, I gotta see if I can do something, you know, and connect some people so, so very, this is when David and I were running flop tag. Together, we ended up doing these Friday beer sessions, like until it kind of beers and tears. were, you know, I would bring in and invite you know, not many, like 10 ish founders and some folks that are still in town. I remember doing this Brian Hayden was there, Molly and Mike from at adapted, were there. And we would come in, and and we would, and we would just be like this. This is messed up. Like, I don't know what I don't know how to deal with this. How do you deal with this? Right? Because I don't know what to do. We have an Brian Hayden and I actually go where we actually were talking about this earlier, he'd come in from Boston. And it was this kind of mutual kind of concept that we came together like, hey, let's, let's see what I've experienced in San Francisco. He's experienced in Boston trying to put this together. Right. And I think like, that is always something that drives me. And that kind of goes back to the work that I did in Detroit. We'll fast forward to mercury. One of the things that I was most excited about joining my partners at Mercury, this is, you know, six and a half years ago, because they were community builders. In Houston. Like you think Houston is big town, it is big, fourth biggest city and country. Completely nascent when it comes to venture capital. Absolutely. Right. And you've been there, you know, Brad, you know, my partner's. And so and so, you know, my, my guys down there, they were building accelerators, they were building fund of funds, they were building things down there. And so it is like, ingrained in our fund. In our in our people. It's like, we are community builders. And we are completely upfront about that with our LP base. And it's important because we invest in the middle of the country, we don't invest in the completely built out capital sectors, like the West Coast, in the northeast, when you're building in places that are still emerging, you got to do more, you can't just be like the capital coming in and writing, because there's like a well oiled machine. Right, you gotta you got to do the work to help build out that community, we believe that we know that we've always done that, we'll always do that.

Brad  
Yeah, I love that so much, because there are probably 10 or so. And you can make an argument that it's smaller, higher, but there's Let's run with there's 10 or so VCs out there. And I'll just say nationally, that everyone in the startup community knows, and they're really aspirational. And startups are going to find those organizations and they're going to get great deal flow. And that's great. And, and disproportionately those organizations, support startups that are in the Bay Area and the Northeast, and leaves a hell of a lot of opportunity for everything in between. I think it's so smart in terms of what you guys are doing. And I've always appreciated the ability to kind of find that find the whitespace. And that's clearly something that you've done over time. So you mentioned a couple of a couple of buzz terms, or I guess, not buzz terms, but some some things that you've done in the past. And I just kind of want to bring those to the surface. So you mentioned flock tag. So flock tag from my understanding was was really your second big soiree into the into entrepreneurship or being an operator. So can you kind of walk us through how you went from being an engineering student at the University of Michigan to being then a multiple start a multiple business founder? And then getting into the investment world? We'll get into the investment world first. I'm really curious about that venture from being a college student in an engineer into being a startup founder, how the heck did that happen?

Adrian  
Yeah. So so you know, you're right, mechanical engineer, undergrad from Michigan, graduated in 2000. When you graduated in 2000, and you're a mechanical engineer, you had one choice. Seemed like no one choice, right? You go into automotive. Either that or just I wasn't creative enough at the time to think about something else. I was like, Oh, I interned here. I guess I should work there. Right. And so I went into this company called Ricardo, which is an engineering consulting firm that worked for all the large OEMs in the auto world. And it was just the most wonderful place to grow up professionally. I got to do all kinds of great work, I traveled the world. I lived in the UK, like it was just, I mean, it was magical. And the way that I built up was able to build up both an engineering mind and a business mind. That said, fairly early on, I knew that I wanted to get into the world of of entrepreneurship. I didn't know how I didn't know what, and I didn't know where.

Brad  
And let me just let me just pause you right there. How did you know that? Because, because when you're going through engineering, I mean, it's, it's in the weeds, it is in depth, you don't have a lot of time to learn about business or anything except the details of mechanical engineering. So where did this desire and knowledge that you wanted to start something on your own come from?

Adrian  
Yeah, two to two reasons. Right. One sort of internally driven one, externally driven. So the internally driven ones that my grandfather and father, were both business owners, they're lawyers, right. But but they had their own practice, right. And they, you know, and they, they had that I kind of saw the way that they were able to operate as owners of that business, right. And in some of the kind of freedoms they had in the ability to kind of, you know, you know, be beyond their own. And there was an aspirational aspect of that, you know, I mean, my dad said, since I can remember, never be a lawyer, so

But, but, but I still thought like, there was something there. That's the only piece of the external pieces that once I got into automotive, I saw what my boss's boss's boss, and my were how, how they operated, and what it looked like from a corporate perspective, in auto. And I felt like that sort of senior level management, like what most people would, you know, auto would probably would aspire to, I didn't feel like it was right for me.

Brad  
I thought it was there's too much bureaucracy, there's just too much, you know, Bs that I think my friends had to deal with. And in lots of things that you know, you know, whether it's like, you know, bad behavior from peers, the backstabbing, just the stuff that you choose to see across corporate life. So so I did. So you're wired as a child and in your, in your formative years, to really appreciate the ability to do something on your own. And then you get into this, this engineering world, and you say, wow, this is really cool. I really like what I'm what I'm doing. I know, you're putting in a huge amount of effort. But But you also said, but this, this is interesting. This is a great launching point for me. But I don't see myself climbing the ranks here to a senior level, because the way it's set up is not something I aspire towards. Yeah. And at that point, you start to look at the horizon, and you recognize that there might be some opportunities to start some things on your own.

Adrian  
That's right. That's right. And here's the here's the point where, you know, Ricardo, North America, you know, I knew the president, well, there's a couple there in terms of like, they had all all the responsibility, but none of the control, right, because the UK kind of mothership was always controlling kind of pulling strings and stuff like that. I'm like, Man, that's like the top job in the country for this company. And it doesn't seem that great, right. So and so that that was where I kind of felt like it was it was the time to try to figure it out. And I didn't know what to do. So my path was, much like you just go get an MBA, let's go to let's go to it was Michigan business school at the time, it turned into Ross during my time there. And that was purely on the basis of I had learned about the salary Institute, I had, you know, learned about that opportunity to kind of figure things out effectively there. And what is it? It's the it's the entrepreneurship Institute, in the in the business school, right. And so he was established before I was there, from Sam Zell and Bob Laurie. And, and so that's kind of why he and there's one reason I wanted to go to Michigan, I love Michigan, but you know, a lot of times, you know, people say hey, don't double up on your undergrad and grad school, but I was like, I want that. It's here. Like, I'm just gonna do that. Right? Big practical. And it was a great decision. Because I went, I networked sound a lot of people and it's still a very, still very warm place, right for people that are learning for students. And so I just, you know, I ended up meeting You know, a couple of just wonderful mentors in that program. You know, one was Tony Grover from RPM ventures, and it was Tom Porter. And, and so these guys became, like, go to mentors for me while I was still at Cardo. And I would just continue to ask them, Hey, what, you know, what's the right path forward, and I learned about venture capital and this and that, and then to kind of, you know, finding my way to the startup that was just getting off the ground and Arbor. And I was through most of the MBA program, and I was like, you know, what, now we're never and decided to jump in, you know, took an 80% pay cut, didn't get nearly enough equity. And in jumped in, in April 2008. And

Brad  
What was this startup?

Adrian
Yeah, a company called boom, dash, right? And so great name. And it was, it was a really good idea in concept. In practice, we just, we just, you know, it was very difficult, right? So in, here's what it was. pitch, you got to take yourself way back to 2007 2008. Okay. At that time, Google AdWords search engine marketing was somewhat established, but not well understood at all. And not well known, you know it very well, obviously. But people didn't really understand how to work with it. And so what we said is, like, Hey, we're gonna build a kind of, you know, digital platform that integrates with AdWords, build landing pages, for your kind of mom and pop, small business. And then and this is the this was the kicker, we were going to sell that through Yellow Page directories. So at the time, there were a lot of these regional Yellow Pages directories that had, at that point, still reasonable revenue base, people were still advertised and great margins, directories, and fantastic margins. Right? As we said, My God, these guys have no digital offering, we can be their digital offering. Great idea. Right? And isn't it great that it is very technical, heavy company can rely on somebody else, you know, as a as a sales engine. So, boom, boom, boom, check all the boxes. Great founders. They're one of them. Still very close friend of mine. Now, and like, I'm in, let's do it, right.

Brad  
Yep. So 80% 80% pay cut, you're ready to to not just work 80 hours a week. But do it work all hours of the week, and get paid a whole lot less with this with this dream in front of you, of this grant? Fantastic Yellow Pages partnership?

Adrian  
Yeah. And go all in. And what we found is that we tried ever, we experimented all over the place. And we could not at the highest level, we could not get the Yellow Page directories, at the time to recognize their industry was dying. Right? Because they say, Oh, yeah, we totally want to sell this offering, we totally want to sell it right? Yeah, we want to get some footprint there. And then you offer it to them. And they're like, they're their customers or clients are saying, well, I only have so much budget. Well, which one are they going to pick, they continue to pick the higher margin one. Right? You know, ours, obviously, by default, ours is the lower margin. And so we tried all these experiments and kind of offerings and different yellow based directories, and in the end, could not figure out the right way. And, you know, my big lesson here is like, Hey, don't hit your ride in the dying industry. You know, that's the that's the core lesson. That's what it is. And so, you know, we tried for a year, and, and then, you know, the CEO, and I had to just shut it down, just the two of us shut it down in March of 2009.

Brad  
Well, I think that's a really interesting period of time, I want to pause and say, is an interesting lesson, not just from a founder perspective, but from a business perspective, which is, if you as an organization, have the opportunity to cannibalize your own business, by all means, cannibalize your own business, because if you don't, someone else will. So I you know, from from my perspective, I mean, that's, that's the big mess of Kodak. That seems like the big mess with the Yellow Pages organization is an unwillingness to change and to be the disruptors yourself. Because ultimately, the their demise is largely well documented. And of course, this ultimately led to you forcing yourself to make this really hard decision to shut down the company, I want to know of what that moment was like, because this seems like a really big low in your, in your career, because to date, you've been working in largely a corporate position, you've been doing really well, you've been getting the feedback that you're doing really well, you give all that up, you give a comfortable salary up, you go and you launch something with some fantastic mentors and people who are really experiencing this. 

Adrian  
And you see have in theory, every advantage known to man. And he made this decision to to call it doesn't work. Right. And I mean, it was, and I, I want to make sure it's clear, like, you know, I was the first employee in the company, and so not a founder, not the CEO, and it was just the CNI, CEO, CEO and I left and, you know, he said, Look, I can't continue to fund this company. And, you know, I, we just got a, you know, you can't continue, you know, and of course, I didn't have any money to help fund it, and I can see the writing on the wall anyway. And so, you know, it's very much, you know, I would say his decision with with maybe some, some consultation with me, and, and others, but it was the right decision, no question about it. It wasn't working. And so, to the question of like, what is like, what do you do with that? What do I take from that? Here's the thing, because of exactly what you said, Brad, I came out of that experience with this the most, like, huge confidence, right? I was, I was so excited about what was in front of me after that. And here's why. everything you just said, fantastic founders. Really, really solid opportunity problem. And it didn't work out. And so what I took from that was like, well, man, if this thing can fail like that, with all of that there, what am I worried about? I gotta go out and just try it myself. I gotta drive something. I gotta start something. Right? Because of course, the reason I went in as a first employee, even though I wanted to be a founder, I was like, Well, I don't know what I'm doing. Right? And so I was like, nobody else is doing. So so why not. And so and by the way, I mean, the other thing, I'm, you know, that story, but for the benefit of the podcast, that the week that we shut down the company, my wife told me, we were pregnant with our first son, same week. no job, no outlook. And so I gave myself nine months to figure something out. And I was able to very quickly find a couple partners, in that we're also experienced consultants. And we built this nice little boutique clean tech consulting company, that kind of ramped us up to a very reasonable income base. And then all along, I'm looking in trying to find, okay, where is my opportunity to start a tech company, as a founder, because I knew that was my next step. Like, I didn't want to be consultant forever, I'd already done that. Right? Well, with the opportunity. And so I was just networking all over to try to find that next opportunity. And of course, that's what I kind of came across the opportunity to start shepherd.

Brad  
So if you need to start a new business, and you need income consulting is a great way to go about that. Because it actually get can get income in the door right away. But that that also is a huge slog, and you didn't stay doing the the clean tech consulting for very long. So you, you found yourself quickly pursuing what ultimately became a main competitor in the in the share in the ride sharing ecosystem, and a competitor to Lyft and Uber. I'd love to hear about how you translated this clean tech consultancy into a ride sharing player.

Adrian  Yeah, yeah, there's a big chunk in between there, right. And so, you know, I was I was doing that work around in Arbor trying to find what my kind of opportunity might be on the starting a software company. You know, I met this master's student at U of M, through my friends at rpm. And one of my, also one of my friends that, that I work with it boom, dash. And they said, Hey, you know, this, this young guy is working on some, some kind of, you know, fleet management software. It's, it's sort of, you know, kind of a A codebase that's been built out from student projects, but you know, there's an opportunity to maybe clean it up. And maybe there's something there, Adrian, you have some transportation in experience. Maybe you want to go into tickets, have a chat, have a chat, began to do some homework and figured out that, you know, there is an opportunity, but of course, at that point, it was fleet management, right. So, the management of fleets like bus fleets, shuttles, limos, taxis, things like that, right. And, in this, you know, my then my kind of, we decided to partner up. And he and I founded this company called Shepherd is, and the shepherd is, was really was the first cloud based fleet management solution. It started in 2000. And in 2009, and great opportunity, rebuilt the code base built a nice UI UX to offer to the university fleet, and then small private fleets. And it will

Brad  
And it started started, right?

Adrian  
I mean, we've absolutely we got momentum at this point in time, you got an emerging industry, you're an early mover, and things are happening, you guys have to be feeling pretty good about yourselves.

We were We were but what we did find out after you're right, we got business in Indiana, in Boston and Michigan, what we found is that the market opportunity for that company was going to be relatively small, because it was just University fleets that really wanted it, it was too risky for me to Miss innisfil fleets. And then the taxi limos were just a little still tight, understandably, with what they can afford.

Brad  
So you created a business and you said, you know, it'd be cool. A billion dollar business?

Adrian  
Yeah, exactly. Exactly. Right. So we started to brainstorm and about what else it could be. And we noticed how much, you know, we had in consumer engagement and sort of, what can we do because we're offering these estimated time arrivals for these bus riders, you know, and we put some investment materials out there and finding an interested investor, and then subsequently partner in the Bay Area, who was also thinking about next gen next generation transportation. And we started to brainstorm, right, and we did for months on end about what it could be, he'd bring ideas, we'd bring ideas. And then in time, we came together to start, you know, this, this new company effectively, right? We put some money in some other folks put some money in, and initially kind of, you know, you know, built you know, the first you know, what, turned into sidecar. Right? didn't call it sidecar first, because we were still kind of working through some things. And in sidecar was before and Lyft it was, it was before, most of these guys had really understood. I mean, we were trailblazers, as it relates to ride share, like true instant ride, share what you see in Uber x what you see in, in Lyft, we were there at the forefront. And it was just an amazing experience, you know, to do that, to raise some money. You know, my, my team year in Arbor moved out to San Francisco, I then started going out there all the time, was out there almost every week, kind of building that first, you know, community for sidecar. And it was just just, again, a magical experience, being able to build that and also to be able to see, you know, you know, San Francisco Bay Area thought of is like, you know, the kind of the apex of startup ecosystem. Right. And it was really interesting to be able to experience that too, especially now that I'm, you know, based in the middle of country.

Brad  
Yeah, absolutely. So, you know, I'm thinking back so for those who aren't familiar with sidecar sidecar had an original business model that was different than Uber black, it became similar to Uber x today. But it was basically a model where, hey, I'm going from point A to point B, if a rider was somewhere between point A and B, instead of having a ride board at a university or something, you could do it, you know, through through the app, you could do it online. I don't know what it was originally. And now you have a digital way of saying, hey, let's let me pick someone up. Like, that's kind of the sidecar mentality is me as a as a driver. I'm going to work every day anyway. So I can, I can pick someone else up and sidecar was was really successful, ultimately wound up being acquired by General Motors, and GM, but of course, it's not as well known as Uber and lift today. So I'm curious to hear you know, your personal experience as you evolved out of the out of the business. How did that How did that come to be? Because I've been You've you've since transitioned, by way of flak tag another startup, but you you've, you're now, as we've we've mentioned a couple times your venture capitalist, but But what was that exit like for for you personally, out of sidecar?

Adrian  
Yeah, I mean, it'd be clear like we did I mean, we preceded Uber x we preceded Lyft, you know, I, you know, we definitely were there, at the forefront kind of building blazing new trails. And, and there and it was just a wonderful experience, you know, to the question of kind of, you know, my, my kind of leaving operationally. So, as I mentioned, I was going out there all the time, almost every week, sometimes two weeks on end. And, and yet, when that started, my second son had been born before I started that, and so we had a have had a house in Michigan, I had two kids under two, and I had, my wife was still working as a teacher, right. And that's a lot. And so I did it, you know, I did it for over a year. And, you know, it got to a point where it just was too hard to do that to be, you know, head of operations and, and do all the work and have the family back here. And so, look, at some point, I just said, you know, to my partners, they're like, hey, look, I, you know, we can't, we can't make the move, we're just still too early, in it from a company maturity perspective, to justify that risk. And remember, I'm an engineer at heart, there's still kind of a certain risk profile and early stage investor, but there's still something there. Right. And, and, and so I didn't see that, you know, and, and so it just sort of felt like, you know, it was the right time to make the transition and said, Guys, you know, I want to transition out operationally, you know, I'll continue to be an advisor, I'll continue to be, you know, help out, which I did. And, but, uh, you know, I think it's time for me to kind of, you know, come back home effectively, right, and, and then continue the journey, you know, and building something new. And I had an opportunity then to, to focus a lot of my energy on flop tag, which was kind of getting off the ground, you know, at that point, and had a great opportunity to help build that out, too, with my partner there. And, you know, and then, as you said, kind of in time transition and investment side, initially at invest Detroit, and then later on, Mercury.

Brad  
I love this story. Because I feel like, I feel like to be really successful in life, you need to get punched in the face a little bit, you need to experience some setbacks. And I remember an employee of mine previously, who had, you know, was just a rock star, had crushed everything to date, and he was applying to business schools, and never shared this to him publicly, because I didn't want it to be taken the wrong way. But I was secretly rooting for him to not get into his number one choice, not because I didn't want the best for him. But because I did want the best for him. Because I wanted him to experience some of that adversity and some of that, like drive to succeed and the need to prove themselves, but I just couldn't imagine a better setup. So here you are. Adrian 14, oh, from middle of nowhere, Michigan, Alma Michigan. And, and you go to the state school, and you find you find yourself out here in the Bay Area, competing with the absolute, best and brightest, in a lot of cases, winning. And this is all happening after you've already had one failed startup under your belt. And and this this kind of feels like the dream scenario here, especially as a community builder, someone who's got a great network. And yet, I know you went into flock dag, right. And so in the interest of time, and you'll maybe we'll fast forward because you had this really interesting rewards program, that that was growing in the Midwest, and getting traction, but ultimately, you make a move that I think, as someone who considers themselves an operator themselves, is is really hard to do, and I think requires a huge mental shift where you move from being the hands on operator to to being the investor. So when you were going through that decision making, what was what was the driver for those decisions? And was there any part of you that felt unsatisfied in terms of what you had done to date as an operator?

Adrian  
Hmm. I don't think that there's anything that I felt unsatisfied in that every company that I had founded was certainly at a very strong position, when I made the sort of transition. And so I think what I felt like is like, I feel really, I really liked that first kind of founding level, you know, you grow and build out, right. And then, you know, once there's a team under the team, they're growing, building, you know, I felt like I, you know, I was a good point where I could kind of hand off the reins, you know, to someone else. Right. And, and so, I don't think there's anything that I would take from that. I do think, though, as I as I go back and think about that, the way I was going through my head, like I, even from business school, I had an interest in venture capital. Right? When I was talking to Tom and Tony, both mentors, I always had that interest. And so that was always in my head. You know, I did an internship at the Michigan venture capital Association while I was in school there, and I and I always had that there. And so, you know, in time, you know, I felt like, again, Florida was in a good position, we had raised, you know, some some money, and we have built out a really, really strong team pulled down the technology in house. In, you know, in my partner, Dave, who was always the CEO of the company, you know, from the beginning, you know, was like doing, he was doing a great job, it was like, Okay, well, maybe there's an opportunity here for me to still stay on the board. And then which I did, and, and maybe just take a little bit of a step back, and then, but then, you know, have the opportunity to do something, basically scratch an itch that I hadn't had the chance to do yet. And so, you know, I was interested in scratching that itch on the investment side.

Brad  
What is it that you think, allowed you to be successful as an entrepreneur, and then also allowed you to believe that you would be successful as an investor? And of course, now we have the benefit of hindsight, no, you're a humble guy, you'll still see say, it's still to be determined, but clearly, you're a successful entrepreneur, and investor. And so what are what are the characteristics that you look back and at yourself in your career that you think allowed you to be successful in these two? Certainly linked but distinct worlds?

Adrian  
So I, I firmly believe that operationally, heavy early stage investors, US me Look, a lot like founders, like really look a lot like them, right? We all have to be able to, to see things that aren't there are obvious to others. We need to see around the corner, competitively in certain industries. And we need to build incredible teams. And I think that there is way more commonality like that Venn diagram, there's so much overlap, in my opinion, and that Venn diagram between the early stage that kind of sea level investor, and founder that I felt confident that I would go in and be able to create some value and be helpful and supportive. Here's the other thing, like, because of my, my journey, I have incredible empathy, for how hard it is to build a company. And I try to, you know, do my best to walk that every day, I'm working with companies and meeting new companies working with CEOs that I that I sit on the board of physicians boards have, but like, that's incredibly important to me, to continue to be that empathetic investor, because it is really lonely. And it's really hard to be that co founder. Right. And so I guess, I just felt like there was, there was a good opportunity for me, and I felt like, invest Detroit because we were just doing pre seed and seed investments. And we're doing it a lot of different kinds of investments, different kinds of companies, right. So a great way for me to kind of cut my teeth a bit, and, and learn, you know, learn a bit on the job, which I very much did.

Brad  
So, Adrian, it's interesting because as a society, we're trained to think of startups as sexy and we think of Mark Zuckerberg and Elon Musk, and Jeff Bezos, and people who are building these huge empires, and it's, it's cool. But I'm starting to think from your perspective, it's a little bit different, right? I mean, even the entrepreneurship network that you you created, it was called beers and tears. And, and one of the things you're talking about is as an investor, empathy and understanding how damn hard it is, is a huge asset that you bring to mercury fund. Why is it that starting companies is so hard?

Adrian  
Man, that's a great question. So I think that it's so incredibly hard. Because there is no, there is no set recipe. There is no sort of, you do 123, and you're there, it just doesn't work like that. There are too many variables, the world is too dynamic. People are too dynamic. And so that's why it's incredibly important for, in my view for for founders to surround themselves with the most valuable, objective advisors they can have. Right, and to be able to, for people to be able to call bullshit on them when they're going down the wrong path. And I think that lots of people can, can operate that way. I think that mentors can, I think co founders can, I think investors can. But you got to build that early on. Because it's incredibly hard. There's just there's so many companies and so many people trying to compete in various sectors that, you know, to think that, you know, if I took this approach, this time before, and I take the exact same approach, it might not work, it might work. But you know, the success rate of startups pretty low, very low, very low. And what's interesting is the best success rate, excuse me, the best success rate for for founders is those in their 40s and 50s. And the best success rate also comes from people who've been working in the industry for so long, because there is a lot of nuance to any business or any industry. And having the advantage of living in that for so long, is extremely helpful. And I love what you said about the importance of having honest and forthright advisors around you. And one of the things that I live by and those who have been on any of my teams now, as well, as a true friend, someone who will tell you when you have spinach in your teeth. It's it's hard, because you don't want to be like, yeah, hey, Adrian, you know, right there. Between your, your left big front tooth, it because it's kind of like it's a little awkward, but my goodness, it's so much better to have one awkward conversation than to look like an ass in front of 10s or maybe even hundreds or 1000s of people if you're on stage right on a podcast.

Brad  
Your teeth look great for the record. But but but I think that's something that is that is really important. And, you know, I think some of my friends, I can be a bit of pain in the ass because I am going to shoot people straight. But at the same time when I'm telling you like, Oh, I really liked this, or this is great. There's nothing in the back of your mind. That is like is is bad. I really like this because it's like, No, you, you know, I'm gonna let you know if I'm not a fan of it. I And that's why I love working with you so much at catapult. Right. You were unvarnished in your feedback to everybody in the room? And it's incredibly and it's really rare to you know, and I just don't I think it's a it's an unappreciated characteristic for people to be direct.

Adrian
You know, I mean, it's almost like kind of being empathetically direct. Like, hey, you know, kind of sucks, but you got to handle this, like, talk to you this?

Brad
Absolutely. Well, one of the I'd love to hear your take, right. So you've been through the wars as an entrepreneur, you're now an investor, when you're looking at entrepreneurs. So this is more or less a question about the business and more about the person. What are the characteristics that you're looking for in great leaders and great entrepreneurs?

Adrian  
Yeah, so you covered one of them already. I firmly believe in subject matter expertise. Right, if a founder and like I primarily invest in b2b companies, right, sometimes b2b, b2c, and b2b, b2c b2b but but still, generally speaking, most of the times that I'm going to be kind of get interested, there's going to be some business component usually. And when you have that, that SME, that subject matter expertise, I believe, incredibly important. Right? So that's sort of a, you know, you just you kind of have that like a thing, right? Yep. And then, and then the, the kind of the, who are the, you know, I, as a founder, as an operator, like, I'm not gonna get into the weeds of like, trying to direct to prescribe any kind of tactical action with the company. But I do really thrive in a dynamic where I am, like, on the phone, talking through various decisions, you know, with the company, and again, this is them calling me This is them saying, hey, I need your input here, Hey, can I get a little feedback here? Right? proactively, and you can, you can actually figure that out, in the first couple conversations with with someone, and sometimes, you know, they've got enough experience that they feel like, good, you know, like, I just really need the money and maybe a little bit of outside, you know, views on a board level basis or frequency. And that's great, right? That's not a great fit for me and for us as a fund. But that's, there's nothing wrong with that. And so, you know, I would definitely kind of hedged toward Okay, Hey, who are still some very capable people, but maybe don't think that they have all the answers, or don't have the experience to lead them to have all the answers such that, you know, hey, we can be helpful, right? I think you kind of marry that up, like, my experience, whether on the industrial side, or the kind of enterprise build outside, I can help that CEO or that team really kind of scale up the company. And that kind of marriage is what I probably look for most

Brad
Yeah, I think it you know, it is it is a it is a relationship, maybe it's not quite as tight as a marriage. But it but it's not that far away, when you talk about a lead investor. And in an early stage, you know, startup that's, that's partnering with a venture capital, so that that fit and having your styles work together is really important. And so I mean, I think that's true for for anyone out there that's looking to start a business, whether it's a hair salon, or a big tech startup, if you're going to engage with a partner, which is really smart to do, make sure that there is incredible amount of trust, that your styles jive, that doesn't mean that your styles are the same. But they have to be able to jive and be able to work together. And clearly, that's something that you have an eye for, you've got a fantastic bullshit meter, I think you call it a spidey sense, you know, a little bit more sophisticated and refined way of saying it, but I think that's, you know, such an important skill, you know, as an investor, and in the interest of time, we'll we'll kind of move on, because I'd love to, you know, pick your brains, and maybe we can have you back on the podcast at a future fit at a future date. But a few questions here before I let you go. So as a as a big time investor, you know, my words, not yours. I mean, your your organization does have over $300 million in investment, which is not not a trivial dollar amount to anyone. But I gotta ask you on a personal level, do you have a Robin Hood account?

Adrian  
No. I thought I could I thought it might be able to catch you there. Now that tells me you're you know, you're one of the real guys. 

Brad
You know, I have a Robin Hood account. I'm not one of the real investors. But I appreciate that. Okay. What is the best piece of advice that you've ever received?

Adrian  
As I was graduating from college, undergrad, my dad said to me, Look, you're going into the workforce. Now you're going to be kind of around lots of different people. Right? And you'll get along easy for you to get along with people. But But look, if there's one thing I'd say is like, do everything possible to learn from other people's mistakes, not just your own. And now you and I think about that well, obvious like you, you and I do that naturally right now, Brad. But if you take yourself back to the young, you know, kid coming out of undergrad getting their first job that was like this, like, like, Oh my god, I'd never even thought about that before. I had never recruited because it's always been Hey, learn from your mistakes. Learn from your mistakes. Well, of course. Do that. Try to, but if you can have your head up, like seeing what else is out there, right? Because that I mean, that takes you mean that you see that in startups, you see that in venture capital everywhere, right? 

Brad  
If that's something that you can truly internalize, you're going to be a step ahead of 99% of the people, because it's not it's not easy to do, learning from other people's mistakes. Adrian, what's your biggest pet peeve?

Adrian  
So I'd circle back to one of the things that you we talked about briefly. You know, we are, we are kind of Capital Partners. Right? I mean, it's really important to us and to me, personally, that we are a partner with, with the founders of companies. And so one of the things that that, you know, maybe it's a less of a pet peeve, I guess it probably could be considered that is, you know, when it when I perceive that companies are really just looking for capital, but they're saying they want the help. Like, I don't think you really want the help, that you're that you, you know, that maybe I think that you need or you want, but look, everybody's entitled their companies do whatever they want. But I think it's when it's when a situation that you see a lot just like, Hey, I definitely want Yeah, I want a partner, I want that. But then, you know, you kind of see like, No, I think he just wants the money. Right? And there are some investors, that's a great fit, right? Have at it, man, it's not a good fit for for us, you know, and we've had that happen to me, it's hard not to here and there. But we I really try to kind of, you know, index on the, on the on the people that really are really truly interested in getting, you know, a real partner a real thought partner. Engagement.

Brad  
Yeah, I mean, two great pieces for us to leave on number, you know, number one, make sure you keep your eyes and ears open learning from other people's mistakes. And number two, when you're talking about the importance of really being surrounded by people who are open to feedback, and open to partnerships, because we don't have all the answers at ourselves. I mean, at MuskOx back, say we're strong on our own, but but we're much better as part of a herd. And I think people who get that mindset are so much better off and it's gonna, it's gonna ultimately turn out to better, better investments for a venture capitalist and better relationships for for all of us, I think.

Adrian  
Yeah, totally. It's the relationships that matter the most.

Brad  
So relationships. It's It's an honor to call you a friend, and definitely appreciate you, you being part of the MuskOx Herd and join us here on The Herd Has Spoken. So thank you for your time, and until next time, we will we appreciate we appreciate you, Adrian.

Adrian  
Well, thanks for having me on, buddy. Appreciate it.

Brad 
All right. Thanks, Adrian. All right. I think we're good.

Adrian  
All right.

Brad  
Yeah, it was great. It was great. Yeah. Hey, appreciate it. We're I know we're a minute over here. So I'll let you free. But thank you. Thank you. Thank you so much.

Adrian  
Thanks, brother.

Brad  
Take care.