Wil Schroter - Founder & CEO of Startups.com: From Service Business to Product Business, Embracing Opportunities, and Managing Health

Wil Schroter  00:00

Especially with startups, our whole culture among startups is to get to the exit, right? I mean, there's a whole bunch of reasons to do that, and I'm not knocking the goal, but there has to be some part of you at some point that says, "Why?" Like, is this just a means to an end, and the end is the exit? What happens after that exit? By the way, that's a conversation very few people have seriously, and if you press them for details, they usually don't actually have an answer.

Callan Harrington  00:26

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 Wil Schroter. Wil is the founder and CEO of startups.com. Startups.com is the world's largest startup platform. They help over 1 million startup companies find customers, funding, mentors, and world-class education. Before founding startups.com, Wil founded multiple successful startups like swapolese.com and fundable.com. He also founded Blue Diesel at the age of 19 and grew it to $700 million in capitalized billings before it became Inventiv, which is now valued at $6 billion. I gotta tell you, I learned a lot from this conversation. We talked about the importance of balancing work and personal life, which is a really common topic, and we more specifically zeroed in on the impact that too much stress can have on everything around you. Wil dove into a specific event that caused him to take this seriously, and he also dove into what he did about it. I can tell you, this is a very timely conversation for me, and I loved hearing his story around this. We also dive into the power of saying yes to opportunities. You hear a ton about saying no to opportunities and really focusing on the essential, and I thought that Wil provided a different viewpoint on this that was really interesting to hear, and it was definitely something that was worth listening to. Now, selfishly, the part of the conversation that I loved the most was talking about how he scaled a services business, and also how to transition from a services business to a product business. These are two topics that are constantly on my mind because I have a service business, and I really enjoyed diving into both of them. And for anybody that's looking to create a product company of any shape or form, I thought he gave an excellent roadmap. So with that, let's get to the show. Wil, I've been looking forward to this. You know, there are a couple of things that I was thinking about where to start this out, but the thing I really want to dive into is, tell me about the age of 37 and what specifically happened to you at age 37.

Wil Schroter  03:12

I've had this theory for a long time, and it started when I turned 37 that there's this curse among 37-year-old founders. Maybe it applies to everybody at 37, but I'm just going to apply it to founders specifically. And our creative director at startups.com turned 37 years old today, and when I told him, I said, "Hey, I've got a story for you." He's like, "Don't even bother." He sends me an article about where I talked about this. He's like, "I already know about all your warnings, Schroter. I get it," right? So here's where these warnings come from. Here's what happened to me. I'm 37 years old at the time, and it was an incredible year, but so much life was happening to me at that same time. I was running five companies full-time, and I was building like an incubator, but they were my companies, not other people's companies, and the last three of them were all venture-funded companies. So they were real stakes companies, not like a landing page that I put up and threw AdWords next to see if it was working—like these were with full staffs, with payrolls and everything else like that. While doing that, I had also just gotten engaged to my now-wife. We had just had what’s now our 12-year-old daughter—a lot going on. We had just moved from California back to Ohio. We had just launched startups.com. Everything in life was happening at once. So it's like a Tuesday, let's say, and I'm at lunch with my friends, and we're sitting there just talking, just a regular day, and I say to the guys, "You know, something doesn't feel right. Like I can't put my finger on it, but I don't feel right. I don't mean emotionally. I mean like physically, something just feels off." And I'd never said this, and I did something that I had never done before. I went home. Up until that point, I started my first company when I was 19. I'm 37 at the time, so almost 20 years, I had never left work to go home because I wasn't feeling well. In fact—and this is so weird to say because I don't want this to come across as a badge of honor, because it's a warning—I had never driven to work or from work in daylight. I was like, first car there, last car out. Like, I leave every night from the office at like, 10 o'clock, 11 o'clock, midnight on a Tuesday or whatever, and not think twice about it. So for me to just say, "Hey, I'm gonna go home," meant I was feeling really off. I'm driving home, and I'm only like, five minutes from my house, and I called my wife and I said, "Hey, you know, I can't explain this, but something's definitely not right. I feel off." And as soon as I said that, my heart stopped. By the way, you can't not notice when your heart stops. That's not like you got some back pain or something. That's how you die, right? And I'm sitting there, like, behind the wheel, and all of a sudden, like, my hands go numb, my feet go numb, and I just feel like all, like, literally, the life draining out of me. It was the strangest thing. I just knew it was really bad. It's kind of like passing out, except you don't wake up. And so I'm also, by the way, behind the wheel of my car doing 55 miles an hour on the highway, right? Great timing. Okay, I don't know how, but I somehow recover. I wake up, the car still going straight. It was bizarre. Okay, I come to, and again, it kind of felt like I had passed out. And because I'm an idiot, I'm like, "Oh, well, this can't be that bad. I'll just keep driving home." I get home, and at that point, my body just goes into shock. There's a scene from the movie Wolf of Wall Street when Leonardo DiCaprio is in a Lamborghini, and he's trying to get out of his Lamborghini. But in his case, he's all on drugs and everything. Whatever—the irony was, I was actually in a Lamborghini trying to get out of a Lamborghini, crawling across the ground with no idea what was going on, minus all the drugs. And I'm like, "What the hell is happening?" So I, like, kind of crawl, stumble my way into my living room, and I call my friends who are back at work, which is only five minutes away, right? And I'm like, "Guys, I don't know what's happening, but you need to come and get me." And so they come over, they bust in, and because they're idiots, they take me to a Minute Clinic, right? I just had a cardiac moment. And they're like, "Cool, let's take you to the place where you go if you scrape your elbow." Yeah. And so sure enough, we get to the Minute Clinic, which is also, fortunately, right around the corner, and the nurse puts a heart rate monitor on me and stuff. She's like, "You've got a cardiac condition, like you need to be in the back of an ambulance, like yesterday," right? Next thing I know, I'm on my way to the ER, spending the next two days in the ER. Essentially, my heart had stopped, and at that time, at that very moment, my daughter would have been about a month or two away from being born. I was just about to get married. I had just started startups.com. I had been running five other companies; like, I could not have had more things going on. I'm 37 years old, but as I'm cruising down the highway heading to the hospital, I'm thinking to myself, "This is how it ends."  After a couple days of testing and being terrified, my doctor comes to me and he says, "Good news, you're as healthy as can be." I'm like, "You've got to be kidding me." He said, "You didn’t have a heart attack. You had a panic attack. You had a severe panic attack, which is basically almost like a cardiac condition." And I was like, "I've never had a panic attack in my life." He's like, "Let me ask you this, have you had any life events that would cause any level of stress?" And he gave me a chart, and he listed all the things you could possibly have, and I checked like every single one off. He's like, "Yeah. I don't know if you realize this, but if you keep running your body without ever taking your foot off the gas, which I had been doing for 20 years solid, your body will give up, whether you realize it or not."  And it was at that moment that I was like, "What am I doing?" And my wife summed it up perfectly. She said, "Wil, you're doing all of these things, running all these companies, making all these commitments, working your ass off, not because you should, but because you can. And what you need to do is determine what you should do, not what you can do." Changed everything at that point. I unwound everything that I was doing. And get this, I started talking to a bunch of other founders about my experience, trying to warn them, thinking they'd be like, "Oh, well, I appreciate you telling me this. You know, I'll look out for this." Here's what I actually got back—all the other founders were like, "Oh, you just had your first panic attack. Yeah, I get them like every six months." Like every single person I talked to was going through the same thing and somehow forgot to mention it.  So that was my curse of the 37-year-old founder, because after that, for the next decade plus, every founder I talked to that had gone past the 37 or hit the 37-year-old milestone had had one of these moments, and it sounded like you might have had some of those yourself.

Callan Harrington  10:07

I've done the diet, I've done the imaging, I've done all the things that you can think of, and the only thing that it comes back to is stress. I'm like, yeah, that started when I was 37. Last year, it started at 37. I turned 38 this year. And the funny thing about this is it coincided with the early stages of the business, taking on too much, dealing with the fluctuations of the up-and-down market, and everything else, and it's the only indicator that makes sense. And what you said really sank in. In my eyes, it was, "I hope the stomach pain doesn't hit because I got a lot to do," right? And so, like, when you just said that to the other founders, like, "That's it? Like, that is it? It's like, I can't afford to have the stomach pain. It's not that I need to take care of the stomach pain. I can't afford this right now because I'm busy."

Wil Schroter  11:06

At what cost, at what point is your success going to outweigh your health? Never. Now, when we're younger, our health is kind of free, so we don't think much about it, right? But as you get a little bit older or as you come across some of these incidents, then you start to see it. I gotta say, up until 37, it didn't occur to me that I could be unhealthy. Now, that doesn't mean I'm perfectly healthy in every way. It just meant that those problems hadn't occurred yet. I'm a few months from turning 50; I'm well aware of those problems now, all of them, right? There is no way you can't be facing down all of those things. And so I think, from a founder's perspective, I don't know that by default they understand how significant this toll is—the health toll, the mental health toll. A lot of us can complain, because we can see it, about how it's affecting our bank account. Isn't a great way to get rich first? It's a great way to get poor first, and then hopefully get rich at some other point. But the poor part always comes.

Callan Harrington  12:08

So true.

Wil Schroter  12:09

The way I look at it is, again, early on, you can kind of ignore your health. As you get a little bit older, your consequences go up. Family, kids, if you have them, etc., all of a sudden those things become very consequential. When I'm in that ambulance and I'm staring at the ceiling, I'm like, I've got a daughter on the way. This isn't just about me or whatever I'm messing around with. Like, what would happen to her if I'm not here? Right? And these things start to become really heavy, which, ironically, creates way more stress.

Callan Harrington  12:36

Yeah, 100%. I want to pull this back a little bit. I want to come back to this in particular. But you started Blue Diesel, the services business, when you were at Ohio State, and you grew this into a large company, especially for a services business. Yes, walk me through that because services businesses are very different. It's challenging on when to hire people, how to grow that, when to get rid of people, because, like, you have this constant ebb and flow. What were some of the challenges that you had in growing that? 

Wil Schroter  13:06

That was the first business that I had started, so I didn't understand any other businesses. And I was a theater major, so it wasn't like I was inherently a business guy. I had no interest in business whatsoever. So I started a business by mistake, not by intention. And I don't say that lightly. That said, the cool thing about a services business is you typically tend to get paid for services, right? Let's compare that to a product business. You and I can work on a product for years before we get paid for it, right? Whereas a services business, you tend to just charge for your services, so you tend to get paid upfront or a few months later, but you tend to actually make money. Ironically, this is why we tell a lot of product companies to start a services business so you can get paid for a while, while you build the product so you can kind of keep that cash coming in. But it was the only business I had known, and I also didn't know how to charge for my services. To give you an idea of how far off the mark I was: now, mind you, this is like kind of pre-internet. You couldn't Google anything, right? I would go in and tell somebody, number one, there's a new thing. It's called the Internet. Nobody had ever heard of it. It's kind of the way AI is now, although AI has got better press. So I would show people what a website was, their minds would be blown, and they would say, "How much for Internet?" right? As if they're paying me for all of the Internet, right? And I'm like, "$200?" I had no idea. I love it. I'll contrast that to a $6 billion company now. It gives you an idea of kind of where I was on the spectrum of being able to understand business or a company. I was like, "This will pay me enough to eat at the end of the week, and so I will price accordingly."

Callan Harrington  14:46

So you grew this, and like, as you got into this next stage. How did you approach when to hire people? Did you approach this in closing deals and then hiring into the backlog? Did you hire ahead of where you thought you were going to close? Did you use contractors and flip them?

Wil Schroter  15:01

Yeah. The paradox of the services business, it always works like this. When you're swamped with work, you think the work's always going to be there, and when you have no work, you think that you're never gonna get work again. Everybody thinks there must be this other version of services where it's just this constant stream of business, and you always get paid. It is always feast or famine. I don't care if you're a web designer or landscaper. It's just the nature of the work. And the secret that I had found out, but certainly nobody told me, is that every services business is a sales business that happens to produce a product. It's not a services business that happens to sell. And the sooner you understand that, the sooner you'll be good at services. What we became really good at at Blue Diesel, one of the first web design companies, was sales. Because of that, we could sell ahead of our capacity being, of course, the number of people that we had on staff. So what I would do, which is kind of odd to a lot of people, and I get why, I would sit down with you and I'd say, "Oh, you need a website? The answer is yes." I don't care what you're about to respond with, my answer is going to be yes, and I'll go figure it out. "Wil, do you know how to build XYZ technology?" "Yes." Not because I'm lying, because I'll go figure it out, right? Whatever you need. I'll just go figure it out and go do it. But if I don't keep saying yes, I'm never going to grow my business. To give you an idea of how consequential that yes is, I'm going to tell you another story. In 1997, at the beginning of that year, I had cut this amazing deal with a local restaurant that you'd be familiar with called Damon's, the place for ribs. And I walked in and I told the manager, I said, "Listen, I'll build a website for you in exchange for ribs." And when I came back to the office and I brought back the bounty that is this sale to my staff, they were over the moon. It might have been one of the most exciting projects they ever worked on because we got $500 of free ribs. So I'm starting there to give you an idea of what a savvy businessperson I was and about how well things were going for me at the time.

Callan Harrington  17:07

Here's a question. When did that change? Was it that your learning curve caught up, or was it that you brought on experienced people that helped kind of operationalize some of these pieces? What was that for you?

Wil Schroter  17:21

Two things happened, and there were just things that I couldn't have planned in a million years, and they were absolutely game-changing. But again, let's set the stage for January of that year, 1997, and about how things were going for one young Wil Schroter, okay? And I said I was pretty happy about this rib situation, if I'm being honest, but that's where my expectations were. We were doing incredible work, like we were working for a guy like Chase Bank, BMW, Best Buy, you know, all these amazing clients, but they were paying us ones of thousands of dollars because we didn't know how to charge. We knew how to do the work, but we were so far gone. One of the clients I was working with was doing work for a small local ad agency in Columbus, Ohio. The ad agency had maybe 40 people there, and we met with them to talk about doing some work for some of their clients. Well, they had a new executive that they had just hired on that was a friend of some of the partners of the firm, a guy named Blaine Walter. And Blaine was maybe 26, and I was 22. We sat down, and I remember at this restaurant called Cooker, and we're talking about how what if we took the 40 people you have and, like, maybe the dozen people I have, and we merged them together. Not only can we do traditional advertising, but we can also do digital advertising. We could have over 50 people at this megalith of a company, right? And he was like, "Yeah, sure, let's do a deal," and so we merged the agencies. Okay? Not three months later, Blaine gets an opportunity to pitch Eli Lilly, the pharmaceutical company based out in Indianapolis, whose key product at the time was Prozac. He gets an opportunity to do an agency pitch. Now, the way agency pitches work, like the big agency pitches, is you send out an entire football team worth of people to the pitch, and the client sends their football team worth of people, and you have these massive, grandiose pitches and massive decisions get made. We had none of that, right? We were just a bunch of Hill Jacks from Columbus, Ohio. We had no business even getting in on the pitch. How we even got that pitch is beyond me. Blaine did all the work, right? I just showed up and pitched, but he got it set up. And I'll never forget, we shut everything down, we rolled the dice like nobody's business, and we said we're gonna do nothing but work on this pitch for an entire month. And we did. And I think the incumbent at the time was a firm named Grey Advertising, a big firm, right? And this was a huge, huge account, so we're like, "Screw it. Let's roll the dice. Let's see what happens when we go pitch up against the big boys." And I remember, we rented this, like, tour bus that we took, you know, across I-70 to Indianapolis to go pitch. And we took everybody with us. We took our receptionist just so we could look big, like, we took everybody, like, getting off this bus. Yes, and I'll remember too, a fun fact at the time when we were driving to Indianapolis—it's like a three-hour drive—I remember I was getting picked on by some of the other staff members because I was still studying for midterms because I was still thinking that I needed to finish my degree. So that, again, gives you an idea of where my head was at. Right. Fast forward, we get into this pitch, and I'm like, in a giant auditorium, and I'm thundering away, talking about the future of the Internet and what it can be and to be fair, the exact same pitch I'd be giving you about AI right now, and in many ways, falling on totally deaf ears, but it was maybe one of the best presentations I've ever done in my life. Everything felt right. So we do it. They kind of pat us on the head. They send us back to Columbus. They were like, "Hey, you know, that's really cute. Thank you. We don't think much of it," right? But we were like, "Hey, look, we rallied. You know, we gave it our best, whatever." So a few weeks go by, and we get a call from Lilly, and the call opens up with, "Hey, you know, it was great talking to you guys. We thought you did a really good job," you know, we're like, "Oh, okay, whatever." And, "We'd love to work with you." "Okay, really? How? Like, maybe we'll get, like, a direct mail campaign or something like that." And they're like, "No, like, we want to give you the account." And we're like, "What do you mean?" They're like, "The whole thing. $250 million a year worth of business for a 40-person agency." Right then, shit got real.

Callan Harrington  21:27

Was it that you were coming at it from this different angle, and that it was just attached to a key initiative that an executive at Eli Lilly had? Was that essentially it? 

Wil Schroter  21:36

You know, I have this sneaking suspicion, and it's just a suspicion, but I've never been able to confirm this, that whoever the key stakeholder was between Eli Lilly and the agency rep over at Grey, he was looking for the world's biggest FU. I mean, maybe. Now, to be fair, it wound up being a phenomenal decision for Lilly. They basically wanted to own their agency, which they did. And if I'm not mistaken—again, I haven't been there in a long time—Lilly is still a client to this day. That's 30 years ago, right? Which is unheard of, absolutely unheard of. And so you know what's interesting about that? Let's just rewind back to $500 worth of ribs. At the beginning of 1997, I'm walking into restaurants selling websites for ribs. Sometime in that summer, I'm sitting across from a Fortune 500 client. Basically, I'm the same guy, right? I'm the same guy doing the same stuff I was doing five minutes ago. The difference was I got put in front of a different audience. You ever have one of those "What if?" moments? What if, maybe you are capable of doing something far beyond what you're doing, but you haven't been given the opportunity? Now, if I'm being honest, being a guy who works with founders all day, I work in the "what if" business, right? Every founder is a version of a "what if." What if this person can actually pull this off? And I see this happen all the time, but I also see it fail way more than I see it work.

Callan Harrington  23:06

Well, but you do run across situations where somebody has a freakish talent in a spot that's hard to get the spotlight shown on that specific talent. And when you get put into that situation, it's kind of like getting called up to the major leagues. Who knows what you really have until you get called up there?

Wil Schroter  23:27

And if you never put yourself in a position to find out, then you won't find out. And I think that's the big thing. Had we not driven out there and said, "Screw it. Let's see what happens," none of that would have happened, right? So you have to put yourself out there. That's why I said earlier, when the client says, "Can you do this?" my answer is, "Yes." Again, I'm not trying to deceive the client. What I'm saying is I will do it, not that I have done it or whatever. It will get done, and I deliver. I go back and I do what I need to do to make that happen. You can't grow a services business only selling what you already have, by definition. 

Callan Harrington  24:07

That brings up a good segue, and I've heard you talk about this quite a bit, on "you gotta have a product." And let me clarify that, not that you have to have a product, but over the long term, a product business is going to be a better business than essentially a service. Yeah, absolutely. Yeah. So, for example, I have a services business, and I totally agree with what you're saying, for what it's worth. And I've got ideas that I wanted to test out. How do I test those out? How do I test out the product ideas? Right? Because it'll be a significant investment for me to just hire an engineer in order to do this. And I've heard you talk about things like deferred compensation and things like that, but I would love to walk through that. What is your advice in that scenario?

Wil Schroter  24:49

I always start out with this: What is a version that looks like a product, but it's actually a service behind it? Here's an example. I'll tell you another story. So in, let's call it 2009. Remember I told you I was running five companies? Yeah, this is Company Number Five. I had this idea, and this is stupid now, but you gotta understand, it was a different time when I had the idea. What if you could click a single button that would unsubscribe you from any email? And anyone now would be like, "Well, yeah, it's in your Gmail," right? There was a time when it didn't exist. There wasn't a time when you couldn't unsubscribe from stuff, or to do it was such an insanely manual process that you just didn't do it. So you just got deluged with all this email, and this is before Yahoo or Gmail and stuff really filtered much stuff. And I would have this routine that I did every Sunday morning. I would sit at my computer with my chocolate Pop-Tarts, dipping them in chocolate milk, because I lived like a 10-year-old. And I would sit there, and I would go through a folder and find every single newsletter that I was stuck on. I would unsubscribe manually and just try to, like, declutter. And even back then, there were 800 million active email accounts, and generally speaking, they couldn't unsubscribe from stuff. So it was a big TAM; it was a big problem. So I called a friend of mine, a guy named Jamie Siminoff, and my friend Josh Roth, and I said, "Hey guys, I know you've been working on their stuff, but would you like to team up with me on this initiative?" And they loved it. And so the three of us co-founded a company called unsubscribe.com. So Josh, who was the CTO, and Jamie, who became the CEO, because, remember, I was running other companies too, they were like, "Well, I mean, to build this would take probably a year and a half, two years, we're gonna have to raise a bunch of money, and, you know, we're gonna have to build engineering teams." I'm like, "We're not gonna build a damn thing." He's like, "What are you talking about?" Here's what we're gonna build. We launched Unsubscribe in six weeks, okay, to give you an idea of how long it took to go to market. Here's what we did: we created two buttons, one that you could download to put in your Outlook Client and one that you could download to put in your Gmail client. And all it did was add a button that, when you clicked "unsubscribe," would forward a copy over to a mailbox that we set up. And what did we do? We were based in LA. We had a bunch of USC interns going in there and finding the unsubscribe link, just like I was doing with my chocolate Pop-Tarts, and unsubscribing. And as far as you were concerned, the technology was beautiful, right? Interesting. So we were able to test this concept. See, from a user's perspective, you don't care how it gets done, short of probably privacy issues we were running into with looking at people's emails, you don't care how it gets done. You care that it gets done, right? And so initially, when we were testing this, it worked 100% because every single time you hit that button, somebody did get you off your email. So it did actually work. Now, was there technology behind it? No, but if we're trying to test in a product before investing in a product, that's the way to do it. So in six weeks, we went from, "Hey, Jamie, Josh, here's a cool idea," to "Hey, we've got people actively, you know, unsubscribing and raving about the product." Here's the funny thing about it. We hadn't even gotten ready to raise money yet, and when that product went out, it turns out someone who has this problem a lot are investors and VCs. So every investor in VC signed up for this thing and went nuts about it. And so we started getting all these inbound calls about all these investors that wanted to put money into this company, which never happens, by the way, and we ended up raising money, like, in 24 hours without even a pitch deck. It was unbelievable. And I give Jamie all the credit. Fun fact, Jamie is the founder of Ring, the doorbell company, so definitely different ventures, and you can see how we've all been through these things together.

Callan Harrington  28:30

It's super interesting. The dirty little secret of a lot of tech companies is there's often somebody behind the scenes pushing the buttons. And I actually think that that's where AI is going to be very interesting, right? AI will allow a lot of those people that are typically just pushing buttons and doing some manual tasks to either automate some of those or make those people more effective at being able to do those in mass, which is an area where I'm personally exploring because I've got a services business, and it's like, how can I use technology, largely AI, that unlocks this to be able to make the service that I'm delivering more valuable? So certain things don't sit on the shelf once it's done.

Wil Schroter  29:07

There's two components to that. One is, how do I package it to make it easy for people to buy? So think like landing page, checkout process, and the second is, how do I create a pricing mechanism that looks and feels like SaaS? Because typically, you're trying to do a subscription or something like that. I'll give an example. I bought a company years ago called virtual.com. It was a virtual assistant business. Now that is the most manual business you could possibly imagine. You're literally hiring a human to do work for you. Okay, can't get more manual, but we put a web front end on it so that people could buy online. We put a subscription model so people could pay on a recurring basis, and all of a sudden it feels like SaaS. It kind of works like SaaS. All we did was change the front end for how the services were acquired. And I'm not saying that that works for everything. I'm saying a lot of that early transition comes from how you package and sell what was even a service before.

Callan Harrington  29:57

Going back to what we talked about earlier, in having to constantly sell so you can consistently hire people and not have to do this churn-and-burn model, meaning, I hire a bunch of people, I fire a bunch of people. You know, recurring revenue, of course, has higher multiples and everything else, yeah. But even more than that, and it's so funny, that's all I cared about before because my whole career is in SaaS. Right? When I got to the services side, I was like, I just want recurring for prediction, period. I just want a better prediction. It's a better revenue that I have in, and it's not necessarily that it's always going to be the most profitable. It definitely can if it's high gross margin SaaS, but it's the prediction and how you can actually grow this business and invest in the right areas. It's way, way, way, way, way easier to do that once that gets going. 

Wil Schroter  30:39

We ran into the same things with the agency. The agency we built in the '90s, no matter how big that agency got, the problem stayed exactly the same, just with more zeros. So here's, I think, the fantasy that small services businesses have: "When I just get bigger, insert problem will go away." It does not. When you get bigger, new problems arise, and the original problems stay. Because before, you're like, "Well, I wasn't making enough money, so now that I can cover payroll," yeah, but now you have more payroll, right? To give you a sense of it, when we were running in 1997, let's say that our payroll was $20,000 a month, right? Like, insanely cheap. Mind you, like, I was the oldest person in the company. I was 22 years old, so we weren't exactly hiring seasoned executives, right? We were hiring all college kids anyway. Within, like, three years, our payroll was $10 million a month, okay? So to give you a sense of, like, "Oh, well, when you get to that size, everything takes care of itself," no, it doesn't. You know how freaking hard it is to feed the beast with a $10 million-a-month payroll? Right? You get a client that calls and says, "Hey, we can't work with you anymore." You know how long it takes to sell to backfill that? Or how many people are affected by that? My job was 100x harder when we got bigger than it was when we were small. At least when we were small, I knew what I was dealing with. As you get bigger, you start to get problems you actually can't solve. You think you're bigger and you're more stable. Doesn't work like that.

Callan Harrington  32:06

Going back to the beginning, you had these five businesses. You just founded startups.com, and you just had a potentially life-changing moment. What did that go into? Right? How did that change? How you decided to build startups.com as a result of that.

Wil Schroter  32:21

Night and day. It could not have been a more seminal kind of "Holy cow" moment where you just stop everything you're doing, which is exactly what I did. Again, I was just overwhelmed with so many things, and at that time, I just did a hard stop on everything I was doing. So here's what I said. This changed everything for me. Mind you, I'm 37 at the time. From this point forward, whatever I work on right now is whatever I plan on doing for the rest of my life. In other words, prior to that, all those businesses I had started, I didn't give a shit about any of those businesses. I wasn't so fired up about getting people off of email. That is all I want to do for the rest of my life at unsubscribe.com. Right? I wasn't so fired up about building websites for Eli Lilly's pharmaceutical business that I was jumping out of bed. Now, I appreciated the challenge of those businesses, but the actual work wasn't something I cared about. So I challenged myself, and I said, instead of trying to say, "What's my dream job?" whatever, I did the opposite. And I said, "What are things that I don't want to do for the rest of my life?" And I think that's an important lens to use, because I think it's really easy for us to talk about stuff we don't like doing. So my thought was, what if you could take all of those things off the table? What would life be like, not in the presence of your dream job, but in the absence of all the stuff you don't want to do anymore? Okay, so I made a list of all the things that I just didn't want to do anymore. Didn't mean I got to magically not do them, but at least gave me clarity as to what to take off the table. So I'll give you some things that were on the list. The first thing: I don't want to work with people I don't like in any capacity for five seconds, right? Now, that is way easier said than done. Okay, let me give you examples of categories of people you kind of have to suck it up with whether you like it or not: clients, right? Yeah, I wasn't working with clients because they were my best friends in the world, and I'm sure that the feelings were mutual, right? But I had to do the work for them. If Eli Lilly called, who was representing, like, 90% of our payroll, and they were like, "Hey, it's two in the morning, you have to hop on a plane and go to Botswana to solve a problem," I'm on a plane to Botswana. There's no way around it, right? They own my life. I never wanted to do that again. They were actually a wonderful client, so I'm not knocking them totally. Get it, but the fact remains. The other part was, when I was doing all these startups, raising money from investors—and I'm not trying to vilify investors, but I didn't like working with them. I just didn't, right? And I appreciated what they were trying to accomplish. I appreciated their contribution to the startup community, but I don't like being told what to do. Not at all, not even a little bit. And that was kind of the implicit thing with the clients, with investors, was I essentially had a boss, and I didn't want to have a boss. And there's different ways to get a boss, even though you think you're the CEO. And so I didn't want to go down the venture route again. I didn't want to go down the fundraising route. The other part of it was, I love helping people. Now everyone says that. Everyone says, "Oh, of course, I love helping people," right? But like, I do it, whether I should or not, I help people I don't like. To give you a sense of how much I like helping—well, it turned out at the time, again, 37 years old, most of the time I was spending personally was with founders like you, just because that happened to become who my friends were. And it turned out that they kept coming to me for lots and lots of guidance and mentorship and advice. What was interesting about that, it wasn't because I had built, like, the biggest thing in the world, like I was Elon Musk or something like that, nothing like that. By doing all of those companies in parallel, I got to live, like, five parallel lives. It'd be like if you graduated college and you took five different jobs in five different industries, and all of a sudden you got to see in real time how your legal lawyer job would have compared to your doctor job would have compared to your night manager at Wendy's job, you know, whatever, yeah. And so I got to see all these versions, like when Jamie and Josh and I were starting unsubscribe.com, and investors were jumping over themselves to give us money. An hour before that, I was running another company. We were about to run out of money and fire everybody, right? So, like, living all these parallel lives, well, all these founders kept coming to me and asking for advice on how to build their companies. And after a while, I kept giving the same advice over and over and over. And it occurred to me maybe there's more founders that needed this advice 100% all of them, yeah. And so I said, you know what? If I aligned what I'm gonna do next with what I love doing on a Saturday, and I use Saturday as something that that usually disconnected from work, like, what are you doing? Because you want to do it. What do I tend to do? On Saturday, I go have dinner and drinks with friends who tend to be founders, and we talk about founder stuff all day in the same way, if you're a sports fanatic, you'd want to start ESPN so you could start talking about sports all day, right? I just found something that I just naturally loved to do, and decided I was going to start a business around it. Although I had no idea what business that would actually be like, what that business would actually do, I just knew I wanted to help founders the rest of my life. 

Callan Harrington  37:31

What I'm hearing you say is a lot of these companies that you're doing before, they were what I'll call mercenary companies, right? It's like, we've got a business, we've got a good idea. We're gonna go execute on this, and our end goal is to make money on this. Solve problems, have fun, of course, but, like, to make money. But this business, after this event, it's a missionary business. It's, I'm in this business because I deeply am passionate about what I'm doing, and if I'm going to be spending my time on this at this point in my life, it's got to have that.

Wil Schroter  38:00

That's spot on. And I would add to that, my whole thing was, I kept chasing a goal, and as soon as I would get to the goal, I would just reset the chains and go to the next goal. And especially with startups, like, our whole culture among startups is to get to the exit, right? I mean, there's a whole bunch of reasons to do that, and I'm not knocking the goal, but there has to be some part of you at some point that says, "Why?" Like, is this just a means to an end, and the end is the exit? What happens after that exit? By the way, that's a conversation very few people have seriously, and if you press them for details, they usually don't actually have an answer. Usually their answer looks something like this: "I want to sell my company so I don't have to worry about money anymore, and I can live well." Cool. What exactly are you going to do with your time after that? "Well, I'm going to... I'm going to read more books." I'm like, "Cool. You just occupied two hours in a 16-hour day. What are you going to do the rest of your time?" And the reason I say this is because we work with an awful lot of exited founders, and the part that they don't tell you about in the brochure is that's probably, of the entire timeline of founders from the start to the finish, the most depressed group of people in the entire founder continuum. Again, and I'm not knocking exits. Exits are wonderful, right? I've done it five times. I wouldn't give any of them back. However, you have to understand that that's just a moment in time. That's just a bookmark. What I was saying is, what do I want to do for the rest of my life, regardless of whether I have an exit? I don't want my exits to be my defining characteristic. I want my exits to be, like, a high-five moment while on a continuous arm.

Callan Harrington  39:32

For many of my friends that are founders that exited enough to be able to not have to work again, you are so dead on. It never gets talked about because, like, it's a hard thing to talk about. It's a hard thing to say, like, "Oh, I made a ton of money, and it didn't go how I wanted to, and I'm struggling." Because you're not allowed, in their minds, nobody wants to hear that.

Wil Schroter  39:54

So here's what happens almost every time, and I warn my friends when they go through this process. When they get toward an exit, I'm like, listen, on the one hand, yes, it's awesome, but let's talk about life after exit, because almost every founder goes through the same gauntlet, and here's what you're about to go through. And I'm not trying to tell you how your world's gonna go, I just want you to remember what I said so that when you hit these moments, you'll understand that this is actually a pattern that you're going through. And so it starts with a whole bunch of high fives, etc. And the first time you notice, as a founder, that something's not right, it's the first time you realize that no one gives a shit about what you have going on today. You wake up, you had 1,000 people reporting to you yesterday. Today, no one cares what you have going on today, that is very difficult to process, unless you've been on the other side of it. It's the equivalent of how parents feel when their kids leave for college, like they were the center of their universe and all of a sudden they're not part of the universe, not in the same way. In this case, you're completely stripped. There's part of you that says, I can't wait to get all of these problems off my shoulders, like I'm so tired of dealing with XYZ, right? What you don't realize is those problems defined how you attacked the world. Those problems challenged you, right? That'd be the equivalent of saying, "I'm tired of going to the gym because the weights are too heavy." That's the reason you go, right? You know, saying that you want to stop doing it is specifically how you stop growing. And so, yes, I totally get it. Those challenges are difficult, and they are, and it feels like something you want to get away from, but it's not until you distance yourself from them that you realize that those challenges are also what made you who you are. But the last part about it, and this is so simple, and no one's allowed to complain about it, is, you actually have no other way to fill your days, and everybody starts with the same BS excuse: "Oh, everybody else doesn't, but, like, I love golf that much," or, "No, not true. I have this hiking hobby, and I'm all about hiking. I'm going to hike everywhere, or all these places that I want to see, etc." The reason that argument falls flat so quickly is because you realize that the only reason those things were special is because you couldn't do them—scarcity theory. Now that you can do them all the time, they're not that special. And if you want to picture what that looks like, think about when you go on vacation and you go to some nice resort, and when you first get there, right? You smell the air. It's beautiful, and you're all stressed out, so it feels so great to decompress, and it feels like the best idea you ever had. About halfway into the vacation, after you've eaten at the same place 28 times, you're like, "Ah, you know, this isn't quite as good as I thought it was going to be." And by the last day of vacation, if you're like most people, you're like, "Dude, I can't wait to go back to do whatever." Right? That's a great analogy. Well, now imagine that's your life, not a vacation. That's not one week, that's the next 50 years of your life, except you can't go back. Now. That's the reason almost every founder starts another company, not because they need the money, but because they need all of those things back. They need challenge, they need purpose, they need relevance. They need all those things back because, yes, it didn't feel like those were important when you had them, but take them away, and all of a sudden, the value becomes obvious. I never thought about it like that, but it makes complete sense. Mark Housel's new book, "Same as Ever," talks about this a little bit, and it says one of the things is, like, we all need a certain level of stress, right? It doesn't need to be overwhelming, like you described, because then you're going to pass out when going down the freeway. But it's that certain level of stress to be activated, right? And I think that's such a good point—challenging consequence, no question about it.

Callan Harrington  43:40

Wil, last question I got for you here is, you know, if you could have a conversation with your younger self, age totally up to you, what advice would you give them? What would that conversation be?

Wil Schroter  43:52

You know, like I said, I'm going to turn 50 in a few months, and so me and all my peers, we have, you know, this thing called the midlife crisis, where you kind of look back on your life, and you question all of your decisions, right? And I look at all of my peers, and I've got a massive peer group, not because I'm so cool. This is my job. I meet lots and lots of founders. I just meet lots of friends, and most of them are very unhappy, and I totally get why. More than anything, they didn't say yes enough. It's so easy to say no to life. It's so easy to be like, "Yeah, I'm not going to do that." Or, "Hey, I'm not capable of doing that. I've always wanted to, but I'm not going to." I'm not sure why, but ever since I was a kid, I've said yes to everything, right? I go in guns blazing everywhere, all the time, without thinking much about it, which I probably should. And I gotta say, now that I look back over the last 30 years of my career, it's the best thing I ever did. Did I make, like, mistakes? Sure, I made huge mistakes, right? But I also lived so much life. I lived like 20 lives, right? And now that I'm old enough to know that you can’t get that back. What I would have told 20-year-old me? Do even more. Say yes to even more. So it wouldn't have been a warning to myself. It would have been a high five to say, "Dude, I had the benefit of you making all these dumb decisions. And guess what? We were better off for it."

Callan Harrington  45:15

Well, you know what? It ties back to what you said earlier, where you talked about Eli Lilly—you had no business being there, but you rolled the dice on that and went anyway. And if you say yes to more things that are aligned with things that you really want to drive towards, sure, you have the opportunity to put yourself in situations where maybe you're not qualified to be there, but if you don't take that swing, you'll never know if that talent's real or not.

Wil Schroter  45:39

You know, my career and my life have been defined by the question, "What if?" What if I could do that, right? What if the delta between where I'm at now and where I want to be isn't nearly what I think? I just haven't taken a step toward it. In my career, I kid you not, I've had like 50 different jobs. I've been a casting director for television. I've been a commercial actor. I've been repping pharmaceutical brands. I've built software. I mean, I've had so many jobs. I've owned a nightclub. I mean, like, you name it, right? Like, I've said yes to everything, right? Now, here's what's really interesting about it: those things, even when they didn't work out, opened so many doors, gave me so much perspective that the only thing I could have done wrong was not doing them right. One day, I decided that that's something I wanted to get into, something that intrigued me. And so I said, I'm just gonna chip away at it 1% at a time until I understand it. And once I started to pick up that, I started to say, "Oh, well, I wonder if I could also do this. I wonder if I could also do this." I just say yes to everything, and I figure it out as I go.

Callan Harrington  46:43

Well, I can't think of a better place to wrap it. I appreciate you coming on, man. I've had a ton of fun in this conversation.

Wil Schroter  46:49

I love it. I appreciate you having me.

Callan Harrington  46:50

Thank you, absolutely. I hope you enjoyed Will and my conversation. What I love the most was Will's courage to be open and vulnerable with his struggles. That's not an easy thing to do, and I feel like I constantly learn something every time a successful founder does that. If you want to learn more about Will, you can find him on LinkedIn in the show notes. Also, if you like 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.