Andy Jenks - General Partner at Drive Capital: Bootstrapping vs. Raising Capital, Mission-Driven Startups, and the Silicon Valley Journey

Andy Jenks  00:00

A lot of technology startup companies believe that the path is, "I raise capital from an investor, and if I don't, woe is me, the world is over." That's not always the case, and I would say that you should bootstrap until it hurts.

Callan Harrington  00:18

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back, everyone, to another episode of That Worked. This week, I'm joined by Andy Jenks. Andy is a general partner at Drive Capital. Drive is a Columbus-based venture capital firm focused on investing in world-class technology companies outside of Silicon Valley. Prior to Drive, Andy was a three-time founder at Formation Data Systems, Discovery Mining, and Infinite Research. Both Discovery Mining and Infinite Research were successfully acquired. Andy's career was a wild ride. He experienced the early days of Silicon Valley, and I thought his viewpoints on a number of common topics were super interesting. We talked about Andy's experience founding a mission-driven company versus a company that was purely out to solve a hard problem. Both of these can bring really unique people and are really motivating in their own ways, but a mission-driven company has additional benefits, and Andy gave a great rundown of these. We also talked about the importance of stage fit—more specifically, how important it is to have people that are the right fit for the stage the company is currently in. Now, the part of the conversation that I loved the most was diving into when to bootstrap and when to raise capital. So for those that are unfamiliar with the term "bootstrapping," that essentially just means you are building the company off of your own savings, and then when you start generating revenue, reinvesting that revenue as growth, as opposed to raising capital from outside investors. I always love having this conversation because I don't believe there is one perfect way to start and grow a business. So much of it depends on a number of different factors, and given that Andy has both raised capital and bootstrapped as a founder—plus he's a full-time investor at a very large VC—I loved hearing his answer to this question, and I think it's a must-listen for anybody that's thinking about starting a business, but even more so if you're thinking about starting a technology company. So with that, let's get to the show. Andy, I've been looking forward to this one for a while now, and the area that I want to start with is: walk us through how you decided where you were going to go to college.

Andy Jenks  03:13

I grew up in New Jersey. My dad was very encouraging of me to experiment and do things on my own. I built my own car from scratch—a 1966 Mustang. My dad helped me do that, and that was kind of the first hint of, "Hey, go for it and figure it out on your own." I was a competitive athlete in high school and was on the recruiting bandwagon for soccer, but I really wanted to get off the East Coast. One night, I was with some friends, and we put up a map of the western half of the United States, and I threw a dart at the map, and it landed in the Great Salt Lake. I'd never been to Utah, but I knew that there was great skiing, so that was exciting to me, that that's where it landed. I emailed the soccer coach, applied very late, ended up getting in and going, and, yeah.

Callan Harrington  04:07

Okay, was it only one dart throw? It landed there, and that was it.

Andy Jenks  04:11

You're in high school, right? So it's a bunch of kids, and the bet was, "I bet you don't go to wherever the dart lands." And it was one dart throw. It was a life-changing experience.

Callan Harrington  04:23

I think I might love the most that you did this because you wanted to honor the bet, and it was this, "We're gonna just go and figure this out." Did you know also at that point that you wanted to be an entrepreneur? You wanted to found a company?

Andy Jenks  04:39

When I was in high school, the joke was that I never had a traditional job. I was always doing something—from diving in lakes at the golf course and cleaning golf balls and selling them, you know, a dozen for five bucks, to I started a small business. Way back in the day, there was a collectible called a Pog. I started a Pog stand in the mall, and then I ended up building that into three different Pog stands in three different malls, and then selling that business right before it collapsed. That was luck, not skill, by the way. So, yeah, I'd always kind of done stuff that was more non-traditional. As far as scratching that itch of what I wanted to do when I was in college, I wasn't saying, "I want to be an entrepreneur." I was very much saying, like, "This computer stuff is super interesting." And again, this is more luck than anything. The University of Utah—people may not know this, but it was one of the early universities that was on ARPANET. So we had the internet, we had email, we had all this stuff from the computer science lab. I had a buddy who was a computer science major and was showing me all the stuff that he had access to in the lab. And I was like, "Holy shit, I'm doing this." And so I picked up a computer science minor, but being in the early days of the internet and having access to that in 1996, 1995, 1997—I mean, that was really what kind of put me on the path of, like, "I gotta get into this internet thing," whatever it was.

Callan Harrington  06:07

So with that being said, actually, I'd love to fast forward. So you went to Silicon Valley in '98. What was Silicon Valley like in '98? Because this was right before all the boom, right?

Andy Jenks  06:17

It was before-ish. I'd say that things were ramping. I'd say that, you know, Alexa, which was the first technology company I worked for, was started in—I believe it was '95. It was a web page archival platform. That's what Alexa started out as. You had E-Trade; you had a handful of these companies that were leveraging the internet to get information out there. Craigslist was started maybe in '97 or '98, but you started seeing some of this stuff. It was different. And what was cool about it—this, I think, speaks a lot to the Silicon Valley mindset—kids showed up like me. We didn't know jack shit. We knew nothing. We knew some HTML, and you'd go experiment, and you'd be in a coffee shop, and you'd meet somebody who was also figuring stuff out. There weren't communities online like we have today. It was all word of mouth. It was all people helping each other, and it was very communal, and I think that that speaks to San Francisco's culture. That was very much the ethos of the city. And you'd be like, "Holy crap, we just put up this web page, and people from Asia are looking at it. That's weird." Like, you all of a sudden had reach into all these different corners of the planet that you never had reach into before, and that was this, like, mind-blowing experience.

Callan Harrington  07:35

I'm curious, you know, growing up on the East Coast, how did that feel, being in that environment?

Andy Jenks  07:40

I woke up every day, and my roommate, Matt Kinsey, he and I would wake up every day, and we'd be like, "I can't believe we live here," feeling so fortunate that we were in this time and place, that things were happening that the rest of the world could not comprehend. We felt lucky. And everybody that would show up had the same kind of wide-eyed opinion. In today's terms, we were making no money. My first job out of college as an engineer, I was getting paid a whopping $31,000 a year—very different than it is today. But the point is, even though we barely had enough money for rent and food, we felt like the luckiest people on the planet.

Callan Harrington  08:18

Alexa was acquired by Amazon, and you were starting to see some success. What was the moment where it was like, "Okay, I've got to start my own thing?"

Andy Jenks  08:28

It was probably at that Alexa moment. So Alexa got acquired by Amazon, which was very exciting. We were kind of working at Alexa because it was a passion. That's the other thing that I really like about Silicon Valley: people like to solve hard problems. At the time, we were solving a really hard problem, which was crawling and archiving the internet. And we were doing something that was more about the mission than about anything else. Amazon acquires Alexa. These stock options are all of a sudden worth money. We were like, "Well, that's kind of cool." And my boss at the time—this guy, his name is Matt Work—Matt and myself and this other engineer, Jason Maxham, we kind of started talking about it, and we were like, "Well, I mean, we really liked the Alexa mission. The Alexa mission shouldn't be shelved. It was a good mission. And B, a good business. Not quite yet, but it was getting there." So we kind of thought to ourselves, like, that mission that we had was really why we were there. It wasn't about the money; it wasn't about all this other stuff. It was about this mission. Because again, back then, it was like everything was new, and so you were so excited about every new thing that happened. I can remember when MySQL released like, dot one version, and we were like, "Whoa, a database that actually works. This is amazing." So doing things like that was actually more important to us than anything. And so we kind of said, "Hey, I think we can do this." We went to—so Brewster Kahle and Bruce Gilliat were the founders of Alexa. Brewster's one of those under-the-radar people that we should look back in history on as like a founding father of the internet, quite frankly. And we went to them and said, "Hey, we kind of want to continue down this path." And they said, "That's cool. Go for it." Like, that's the ethos of the Valley, which is, you do your time here. You work hard; you do your things, and then I support you with the next endeavor. And we asked for a copy of the internet. We got access to it. We gave up some equity, obviously, in the business, and we were off to the races with a new company that we started called Infinite Research, and we were kind of down that same path of the mission from Alexa. 

Callan Harrington  10:39

You mentioned working on hard problems, and you mentioned being very mission-driven with the company. Which one's more important to you?

Andy Jenks  10:47

My thinking has changed on this over time. I'd say if you asked me 15 years ago, I'd tell you hard problems. One thing I have realized is that hard problems for hard problems' sake do not make for a business. So I would say that mission-driven, for me, is more important today. You know, when we started Discovery Mining, which was after Infinite Research, it was very much, "We're solving the hardest problem. We have the best technology, so we should therefore win." And the answer was, we weren't winning.

Callan Harrington  11:21

Why was that? Why in particular?

Andy Jenks  11:23

Because, yes, we had the best technology. Yes, we were redefining an industry, but we were redefining an industry, and so that was really hard to do. We were in the legal technology space, and we were going against 15, 20 years of status quo. And so changing that behavior pattern is very, very difficult, especially when you're talking about bringing confidential documents online. And so the good thing about that business was we had a whole bunch of people that were mission-driven. And so while we weren't winning every deal, while we had all kinds of issues with the technology, we were in a market we didn't know or understand, we were there for the mission, and so that was—that's kind of what got us through some of those hard times. So I'm very much mission-driven. I'm on the board of a company called Immuta, and Matt Carroll is the CEO there. He's ex-military and all this other good stuff, and so they are 100% about the mission, and they find some of the best talent in the world to work at Immuta. And of course, they pay them fairly, and they do all those things, but the talent that they can attract is just world-class because of the mission of the business and what they're going after.

Callan Harrington  12:33

Yeah, and I think it's one of those things, right? It's where, if you've got really good people, right, you could have the greatest mission in the world, and you're not going to report to a bad boss for very long. But if you've got great people and it's mission-driven, I always feel like that's the key. The key is it's going to get you through those hard times because you're working on a problem that's really worth solving.

Andy Jenks  12:52

Yeah, startups are hard. I mean, it's the hardest thing you're ever going to do. It's not really harder than raising kids, but almost. I mean, it's a really hard thing to do, and if you do not have the resolve, if you do not have the grit, if you do not have the people around you, if you do not have the mission, if you do not have the clarity of that, it could fall apart real quick.

Callan Harrington  13:13

How did you pull all those together in these startups that you founded?

Andy Jenks  13:17

San Francisco was a mentor. Like, the city itself was a mentor. The collective intelligence and people in the city, and then mentors—specifically mentors along the way as well, of course—watching other people, other founders, other startups, other people that worked at startups go through all these processes. Like, the entire city was your therapy session because everybody was kind of rowing in the same direction. And so you had this collective wisdom that was just kind of passed. It was like, you know, it takes a village; it truly took a village, and you'd see breakout successes happening, and then you'd see somebody—like a buddy of mine was employee number, I think he was like, 29 or 27 at Google. And you'd be having drinks in the Mission, and you'd be talking about hard problems that you're working on and how they're getting through it, hearing about that and seeing that firsthand. So when you do experience it, a little edge of knowledge is kind of how you pull it all together. And then again, I mean, at least our companies were super transparent. I mandated a very flat organization. We tried to have zero hierarchy. We did have hierarchy—obviously, you have to—but the point is, we really went with this kind of lean mentality, even at, you know, 150 people. You have to really put a culture on a business, or else the culture will be put on you, and you may not like the culture that you get.

Callan Harrington  14:46

So San Francisco has that, right, and it's a very known position. They have the ecosystem. Everybody gives back. I'm starting to see a little bit of that here in Columbus, but New York doesn't have it even close to the level that Silicon Valley does, although I'd say New York is probably the number two, maybe Austin.

Andy Jenks  15:02

New York, more so than Austin, I'd say.

Callan Harrington  15:04

How can that be created?

Andy Jenks  15:06

I don't know, and I attribute a lot to the culture of specifically San Francisco and the Bay Area historically—that kind of 60s, Bohemian, kind of just infused culture of the city. I think so. Like, when I moved there, it was very accepting. Anybody could move there and feel like they could do it, and when they did, they felt like, "Pay it forward." It's kind of like, "Sure, I have $25,000 to invest. Let's go do this." You know, it's like that type of mentality just kind of was in the culture and the DNA of the city, and Columbus is starting to get there. Like, I can see some of that, but I will say that Columbus, we found—and again, in a parallel to San Francisco when we moved here—it's a very welcoming city. People were really quick to be like, "Welcome to Columbus. We're your neighbor. We live around the corner. How old are your kids? Oh, we know some people with kids your age. We should connect you guys." And like, it's very community-oriented, a lot more so around kids, though.

Callan Harrington  16:17

It's interesting. You brought up a key point: Columbus is definitely very welcoming when it comes to the family, the family environment, the neighborhoods in particular. The challenge is that unless you grew up in the business community here, I think it's actually one of the harder ones to break in and network. And I've had friends from outside—they moved here—like, "How do I break into the business community?" And I can't even make this up, they literally say, "I love my neighborhood and all the people in it, but I'm struggling to get into the business community," and it's definitely something I think that it's going to take real effort for people to get behind. But when it is, man, does it actually make things move a lot easier. You know, I've been surprised. I put on a monthly CEO dinner, and the amount of people that have been interested to come—I thought this was going to be really hard to kind of get off the ground. It's the opposite because there's just not as many outlets like you're describing. Another thing I'd like to circle back to is you've had two VC-backed companies and a bootstrapped company. What are your thoughts on that? And I'm really curious to get your opinion because, obviously, you're a partner at a very successful venture capital company. When should a company bootstrap? When should a company take capital?

Andy Jenks  17:25

A lot of technology startup companies believe that the path is, "I raise capital from an investor, and if I don't, woe is me, the world is over." That's not always the case, and I would say that you should bootstrap until it hurts. And what do I mean by that? I mean that Infinite Research—we raised money; we did that whole thing. Discovery Mining—we didn't raise money; we bootstrapped, and it hurt. Oh man, it hurt. We didn't get paid all the time. Even when we were 60, 70 employees, there were months where we would have to ask the executive team to, like, wait a month for their paycheck, and that hurts, but it was the right thing to do because we weren't a venture-backable business. We thought we were, and maybe we could have been, but we really weren't. You have to really understand the type of business that you have and determine if it is venture-backable because once you take money from an investor, you have to think about it—it's not Andy's money or Drive's money. It's the teacher's pension's money; it's the endowment's money; it's the sovereign wealth money; it's somebody else's money. Of course, we contribute—every investor contributes capital to their fund. It's a requirement, and it's part of the deal because it makes you have skin in the game. So, yeah, it is some of my money, but like, if I'm writing a $10 million check into a Series A company, like, that's not $10 million of my money, right?

Callan Harrington  18:54

Right.

Andy Jenks  18:54

So what we have to do is we have to believe—because at the end of the day, we're stewards of their capital, right? So we have to believe that this check that we're writing into this business is going to get a return, a multiple return of that capital that is asymmetric to where that endowment or pension or whatever is going to get elsewhere in other markets. So what does that mean? Once you understand that as an entrepreneur, it should either terrify you or it should make you really excited because it should terrify you if you believe that you're going to be able to sell your business for like, $100 million, because for a venture capitalist, like, it's not worth it. That's not worth it. If you believe that you're Google or a trillion-dollar business, it should make you really excited because now you've got a partner that can come along for the ride with you and continue to back you. And when you have to raise $200 million, like, you've got that money in the back seat, and you're just going for it. And so, like, that's really the split point is understanding, "Do I have a venture-backable business?" From different fund sizes' perspectives, that could mean outcomes of different levels of magnitude. Where we typically think about the world is, "Can this business get to a billion dollars of gross profit?" So this has nothing to do with valuation. We don't care about valuation—a billion dollars of gross profit. Like, think about how big that market has to be.

Callan Harrington  20:24

Sure. I mean, you're talking, what, five to 800 million in revenue? So, yeah, it's gigantic.

Andy Jenks  20:28

It's gigantic. And so, like, if you've got a great business, and this happens all the time, where people come to Drive or talk to me, and they've got a killer business, and it's like, "Don't raise money. You've got an awesome business." And sure, you can't see it yet, but there's a clear path to $30, $50 million in revenue in here. And like, if you bring me on board, guess what? We're going to be having board meetings. I'm going to be asking how you expand your TAM. I'm going to be asking when you're moving into adjacent markets. I'm going to be holding you accountable on governance items. You're going to have to deal with all the personalities of the board. Like, there's a lot of things that—you've got a great business on right now, and if you got it to $50 million, like, I don't know, that's pretty good, but for us, not even close. So, like, are you ready to step into that? And so I didn't realize that, and it was more by luck, that Discovery Mining was the non-venture-backable business that turned out to be probably the best outcome that I've ever had in my life. You have to just understand the ecosystem and where you're at. But once you get on that treadmill, you're not getting off.

Callan Harrington  21:32

Yeah, and actually, just a correction from earlier, you've got to be at, you know, $1.8–2 billion in revenue to land on a billion in gross profit. I love how you just broke that down, and I think that's so important. And actually, what I probably love even more is that you mentioned your biggest success came from a bootstrapped company, because—and this is a debate that comes up all the time on do you take venture capital or do you not with a tech company in particular? And the multiples are still good on a bootstrapped company that's growing very consistently, and if the goal is just to get cash, like, if that's your goal, there's totally okay—if that's your goal. You could be mercenary-driven; you don't have to be mission-driven. I definitely see the advantages of being mission-driven, but there's no reason not to do that, right, and get a good outcome, because you're going to have a hell of a lot more control over where that cash goes on exit if that's the case. Because another thing with the VC world is like, you've got to bet big. And I think it's even more important that you're mission-driven if it's a VC-backed company, because you need the capital to go really big, and you're going to have to deal with all sorts of stuff. It's almost a guarantee you're going to have layoffs if you're going for as big as you can possibly get, and those are so hard to stomach. I've been through countless ones in my career as an example. And if you're not really attached to that mission, that's so much harder.

Andy Jenks  22:53

Totally. And the other thing about a venture-backed business that you have to understand as well as a founder is you will 100% have layoffs no matter what. Even the most successful venture-backed businesses have layoffs, and it's at different stages. So like, let's take an example of a company that's crushing it. One in mind that I'm on the board of—the CTO there, his name's Mitch Coupette, and he talks about companies—he's been a founder several times. He chose not to be a founder this time and joined as their CTO. And he talks about it as stages. As you know, it's a rocket. You've got the boosters; you've got this; you've got this, and then you got to get up, and then you've got to get to the moon, and then you got to get back. And there's different stages along the way of what propels you into the atmosphere, into space, to the moon and back. And people's skill sets—sometimes you outgrow them. And there are people that are zero to one, there are people that are five to 10, and then there are people that are IPO, pre-IPO, post-IPO, right? And so the thing about being a venture-backed business is that you've got to appreciate that there is going to be a binary outcome. And so you have to, whatever you do, put the business first. So you have to be hiring and firing and going for that brass ring and continuing to—so mission-driven is the most crucial part of it. Culture and being mission-driven is the most crucial part of it. And then you also have to understand that this person who's been with you since day one is probably not the person that's going to get you to the next level, and you're going to have to part ways with them, and that sucks, but it's just the facts. It's just the way it works. And so unfortunately, people that are outside of Silicon Valley, when that happens, they see that as a negative versus—I think about some CEOs in the Valley who have taken companies, and what they are is they're the professional person that, when the founder gets moved to exec chairman or something else, they're brought in, they take it public, and then they go and they do that. There are great folks, especially in sales. They show up and they're specialized, and they say to the investors, "You know, I'm zero to 5 million, I can get your business from zero to 5 million. I do it over and over and over again, and once we get to 5 million, I'm out." And so you can start specializing. Outside of that ecosystem, it's harder to find that. And then when that first happens to a venture-backed company, like in Columbus, for example, it's a "Holy shit" moment, and it doesn't have to be. But again, these are the nuances of being venture-backed versus not. And then when you're bootstrapped—you know, at my company, when we were bootstrapped, we definitely brought people along because we had loyalty to them, and we wanted them to continue on with the business, and they weren't bad at their job; they just weren't going to get us to the next level. But guess what we didn't have to do? We didn't have to show 150% year-over-year growth. It was just us, and we were managing to cash. And are we growing fast enough for our cash? And can we take this part of the market? And we just had a different lens on it, so it was different. Now, when I've had venture-backed businesses, yeah, it's hard.

Callan Harrington  26:19

You've got a goal. You've got a goal that you have to hit. Yes, you're gonna have pivots, but the end goal is the same. The end goal doesn't change, and you've gotta be marching towards that, towards that plan. You know, it's funny. You mentioned stage fit. I think stage fit is so critical, and you kind of gotta accept that there are just different stages. And I'll look at myself—I'm very much the one to $10 million guy. Get this thing off the ground, adapt to market signals, and grow this thing up, and it's a lot more organization that you have to do. And there are politics that come into place when you're a $100 million business—just a different business.

Andy Jenks  26:51

Totally, and that's okay. So knowing where you're fit—I'd even argue on the similar to what you just said—if you're on the executive side, know where you're a good fit, be able to talk to where you're a good fit, and you're a good fit, and you're gonna put yourself in a better position to get some of the best jobs that are out there. Totally, and I've got several friends that have never been a founder, but they've been that kind of consigliere, that right-hand person to the founder from the earliest of stages, and have grown with companies and then left companies, and then grown with other companies and then left companies. And would tell you that that's all they want to do. They never want to start a company. The other thing that's really interesting that I would say I did not appreciate until I flipped onto the investor hat side as opposed to being an entrepreneur, is this goes back to my point about stage fit. If you are a founder—of course, there are legendary founders. There's Zuck, you know, there's Larry and Sergey, there's Brian at Airbnb. They're just special, like there are special people. Just because you have the title "founder," that's cool. That's your title. Nobody can ever take that from you. You are the founder of the business. It doesn't mean that you deserve the title CEO, or CTO, or whatever your C-level is inside of the business that you start. You have to earn it. And there are so many founders that just believe, "Well, I'm the CEO," and it's like, well, yeah, you are the CEO, and you're earning that title every single day. Again, this is mostly venture-backed businesses, right? But you're earning that title every day. You're earning the job. You're getting your stripes, you're taking out the trash, you're doing all the stuff. At some point, the business could outgrow you. And knowing that and being self-aware enough is very difficult. Very difficult. Again, when you raise venture capital, understand what the game is that you're playing. Right? They talk about the arena. Understand the arena and the rules that you're playing in. Because if you don't, you can get blindsided.

Callan Harrington  28:53

All right, you had a ton of success as a three-time founder, and you moved to the investor side. Here's one of the things I'm particularly interested in—you could have just done angel investing. You went all the way to really do this as a full-time job. What led to that, and what have been the biggest changes that you've had to make, going from the founder/operator side to investor? 

Andy Jenks  29:14

I was angel investing, right? Probably made close to 70 angel investments. Now, I've not done any of that since I joined Drive—obviously, there's conflict—and that was fun and exciting, and that actually is what catalyzed me to want to join a fund because writing a check into a business as somebody who's kind of helping fill out the round, so to speak, which is kind of what angels do—yeah, like, Outreach is a good example. Outreach.io—I don't know if you've heard of that company, but pretty good success. We were the first 50k in, and that was fun and exciting. And Manny and I would meet every week, and we'd go through pipeline and do all kinds of stuff. And it was great. That is what's exciting to me about investing. And at $25,000, $50,000, $100,000, $200,000—you don't get that with businesses of more scale and things like that. You're just filling out the round. And so what's really fun as an investor with a platform and where you can write bigger checks is you can have enough conviction for that founder, for that market, for that product, for the data that you're getting back, whatever it may be that you're hanging your hat on, to say, like, "No, let's go for it. I'm gonna write a $10 million check, and we are gonna hire the team, and we are gonna go for it." That's what's exciting and terrifying, but exciting because it gives you the ability to really make a dent in that business's trajectory. 

Callan Harrington  30:40

Your impact is magnified because of the size of the checks that you can write. And honestly, it gets back to the same theme throughout this whole episode. It's, if you're mission-driven, you can be tied closer to it as you help this company grow, is what I'm hearing.

Andy Jenks  30:54

100%. I love that. I just want to be very, very clear, though—the one place where I think investors get cross on that, on the impact, is at the end of the day, investors can make an impact by allowing the founder to pour gas on the fire, but the investors—it's not your job to run the business. It's not your job to be in their ear. It's not your job to micromanage. This is my operator side as a board member. If you think I'm your boss, we're a mess. The whole business is a mess. The board is not your boss. The board is definitely not your boss. The board can hire you and fire you, for sure. Of course, that's true, but they're not your boss. They believed in you, so you need to go for it. So when I say "impact," it's more, "How can I enable the person that I believe in the ability to amplify their vision, their strategy, their mission, whatever it may be?" I would say that for founders that are listening, if you believe that your board is your boss, you're twisted, and you've got to fix it because that is unhealthy. No, it's taking control. You got to take control. Sometimes the investors have pushed a founder too far and their confidence is broken, and unfortunately, that's a really tough spot to be in, but if you want to take your company back and you're in that position, you need to put the investors in their spot because we're not there to manage your business. If you look back at when you first took investment from an investor, it was—they're believing in you, your mission, your business, your metrics, whatever they hang their hat on. Sometimes it's the person, sometimes it's the market, sometimes it's a combination. And so you've got to take it back to that question, which is, like, when you invested in me, Mrs./Mr./whomever board member, what were you hanging your hat on? Was it me? If it was me, then, like, let me run my fucking business. I've got an awesome founder that debates me all the time, and I love it. They don't always do the things that I recommend, and that's cool because it's not my company; it's their company. You really have to be thinking about that as a founder, especially if you take investment from VC.

Callan Harrington  33:09

If that's the case, right, and the VC is very overbearing in what that is, at this point, the VC could already be pushing them out, so you don't really have a lot to lose to come back in here and go back into it. Is that a fair assumption, or is that pushing it way too far?

Andy Jenks  33:24

Maybe it's pushing it a little far. Ultimately, if you find yourself in that position, you got to stand up for yourself and your business. Like, I can tell you, if I show up to a board meeting and they're looking at me for strategy or whatever—man, what are you doing? That's what I'm thinking in the back of my mind. Whereas, again, I've got several excellent founder CEOs that have earned the right to be CEO, that the board meetings are, "This is what we did. This is what we're doing. This is who we are, and this is our strategy going forward." And it's our job to put guardrails on it and have the conversation and push back and test and do all these things, but ultimately, they've made the decision. It's only our job to just push on it enough to make them start questioning and be like, "Okay, did we think about that?" "Yeah, we did." "Okay, we're cool." Whereas if I show up and they're like, "Everything is awesome"—we call it the Lego Man—everything is awesome and it's not. And I'm in there defining strategy or defining a hiring plan, in the back of my mind, I'm like, "What are we doing?"

Callan Harrington  34:34

I think it's an excellent breakdown. Andy, last question I have for you, okay, if you can have a conversation with your younger self, age totally up to you. What would that conversation be? What advice would you give them?

Andy Jenks  34:44

The advice that I would give would be to just trust yourself. So part of the reason why I became an entrepreneur, and I was an entrepreneur, and I had some modest success as an entrepreneur, is because I didn't know any better. You know, like, I didn't have a standard, or "This is what you're supposed to do." I was just like, "Well, that looks like a problem. I'm gonna go fix it." And it comes back to all the way from when I was a kid. It's like, a car shows up, and it doesn't work, it doesn't run, it doesn't do anything. My dad's like, "There's your car." I didn't know a three-speed transmission versus an automatic versus whatever. I didn't know how to do any of that stuff, and I didn't have any pre-knowledge of what it should even look like. I was just like, "Oh, well, I gotta go fix that." And that's the advice I'd give myself, which is, like, you've learned a lot, and sometimes it gets in your way. Don't let it get in your way. Trust your gut. Trust your instinct. When you see something that looks screwed up—like it probably is—and that gut reaction that told you it was screwed up is probably going to make you tinker enough to make it work. And sure, you accumulate a lot of knowledge along the way. But sometimes that knowledge is more of a hindrance than it is a help.

Callan Harrington  35:58

I t's paralysis by analysis. 100%. My problem was I was taking too much advice from too many people.  And then I would change my course 500 times, and I'd get so far away from that original gut feeling. I would do it, and then I'd go back and do my own gut feeling, and that was the one that ended up being it anyway.

Andy Jenks  36:14

Yeah, you know when to trust your gut and when to be like, "I don't know enough about this yet."

Callan Harrington  36:20

I think it's such good advice. Andy, this was a blast. I'm so glad we could do this. I appreciate you coming on the show today.

Andy Jenks  36:27

Yeah, it was great. I enjoyed being here. 

Callan Harrington  36:35

I hope you enjoyed Andy and my conversation. I loved hearing Andy's answer on when to bootstrap and when to raise capital. If you want to learn more about Andy, you can find him on LinkedIn in the show notes. Also, if you liked this episode, you can find me on LinkedIn to let me know. And if you really want to support the show, a review on Apple Podcasts or Spotify is very much appreciated. Thanks for listening, everybody, and I'll see you next week.