#10: Greg Galant, Muck Rack

Welcome to From Startup to Grownup, the podcast. My name is Alisa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grownup. Each week I talk to founders, creators, advisors, investors, and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number 10, double digits. So exciting, and I'm super excited about this conversation with Gregory Gallant. Greg is the co-founder and CEO of Muck Rack, which is a software platform enabling PR teams to find sources for their stories. He's also the co-creator of the famous Shorty Awards. Greg and I had an incredible conversation covering all sorts of topics, like why he decided to bootstrap and the pros and cons of bootstrapping versus taking VC money. Greg talks about how his job as CEO changes every 6 months, how he learns what he needs to, and why he's come to be grateful when he gets to sit around being bored. Greg also talks in depth about what it was like the first time he had to fire someone. This is such an honest conversation filled with value. Please enjoy my conversation with Greg Gallant. Welcome to the show, Greg.

Great. Thanks so much for having me, Alisa Cohn.

I'm so excited to have you. And I first want to just ask you about the early days of your entrepreneurial career when you founded an internet company at age 14. Tell us about that.

Sure. So there we have to go all the way back to the '90s, and it was when it just became possible for anyone to put up a website. I was a bored kid in the suburbs, so I played around and figured out how to make my own website. And then it occurred to me like other companies would probably want to have websites too. And it's just so weird to describe now, cause it's just so obvious why you need a website. Right. But I was going around pitching local businesses and no one asked me, why should I use you to make my website? They were just, the objections were what's a website and why would my business ever need one? But I ended up building the websites for a local chain of weekly newspapers. A French philosopher, a clinical trial labels company, and, uh, quite a few other clients.

A French philosopher?

Yeah, I'm probably not going to pronounce this right because I don't speak French, but Bernard-Henri Lévy, who's a big public intellectual there. Here philosophers don't get all that much attention, but they're like— he, you know, he's married to a model, lives in a castle, like If you're gonna be a philosopher, be a French philosopher.

Okay. That's an important tip for everybody. So after that auspicious beginning as an entrepreneur, you then, I'm sure a lot of things happened to you, but you founded Muck Rack. So tell us the founding story.

Sure. So I, I ended up getting into the whole social media world really early when I launched my podcast back in 2005. That was right when I graduated college and having been in the early web world. The early podcast world reminded me a lot of that. In 2005, nobody knew what a podcast was. So I started one interviewing entrepreneurs. I interviewed Reid Hoffman back when LinkedIn only had 50 employees.

Incredible.

I'm pretty sure it's the first podcast he was ever on. I had the founder of Yelp, the founder of Vanguard Group. And then one of the people I had on my podcast was Ev Williams, who was working on a really hot podcasting startup. Called Odeo. This is back in, I think, '05, '06. Odeo didn't work out, but I'd stayed in touch with Ev because we were both in the podcasting world. And that led me to sign up to the little side project he was working on on the side of Odeo, Twitter. So I signed up for Twitter early. I got my first name on there, @Gregory, because no one had grabbed @Gregory yet. And I saw this great stuff happening on Twitter, but no way to figure out who you should pay attention to, you know, if you're interested in any topic, who's someone who you should follow. So we had this idea that we could crowdsource who would be the best person on Twitter by letting people vote with a tweet, which now everyone lets you vote. You know, they say, please share your vote on social. It had never been done before. So my co-founder Lee Semmel and I had this crazy idea. Well, launch this Twitter voting system. We'll call it an award so people want to vote. Tweets are short, so we'll call it the Shorty Awards. And we launched it, and that was the birth of the Shorty Awards. Within 24 hours of launch, it became the top trending term on Twitter because this social media voting was so viral.

I see.

And then when we actually put on the Shorties, we saw it just got a ton of press. Wall Street Journal, New York Times, BBC, all covered it. We had lots of journalists at the first Shorties. And having launched other things in the past, I'd always saw how hard it was to get press for a new idea. And here I saw the journalists were tripping over themselves to come to and cover the Shorties and then realize it's because all the journalists are using social to figure out what to write about. So that led us to launch the first version of Muck Rack, which was just a place you could find all the journalists in one place, kind of playing on the name muckraker, the old term for investigative journalists, and a magazine rack to find all the news in one place. So Muck Rack version 1.0 was just a free website. Here are all the journalists. It became very popular with journalists. We had over 10,000 requests to get listed there. And then I kept running into PR people all over New York and they were like, oh, I love your site. I'm using it to figure out who to pitch on the story ideas. Like, oh, there's probably a business idea in that. And I saw from friends of mine who'd launched SaaS companies with recurring revenue models, like Ryan Holmes over at Hootsuite, an old friend, they won a Shorty that first year. And I saw them taking off and MailChimp in the early days and a bunch of other ones. So while the Shorties were profitable every year, it was always this kind of roller coaster putting them on. Since we never knew if we'd make profit, we never knew in advance we'd make the profit for sure. And we had to sign these huge venue contracts that put us on the line for a lot of money. So wanted to switch Muck Rack into being a SaaS business, provide this value for the PR community while keeping it free for journalists so it'd be sustainable. And we did that a couple of years after launch and it worked. So for the past 10 years, we've just been growing it and tremendously expanding the feature set and what it offers.

Well, that's so fascinating. I did not know that the Shorties predated Muck Rack and that actually one idea led into another.

A lot of people assume it's the other way around, but Shorties came first.

Right. Are you the kind of person where you sort of are like, oh, that's interesting, I'm gonna follow that, and I have this insight, so I'm gonna think about that? Do you just tend to follow your curiosity when you have new ideas?

100%. That's what led me into using the web early on in the '90s and then podcasting. And I mean, in '05, it wasn't even called podcasting. It was just called RSS feeds with enclosures. But I just thought it was so cool that you could like get an MP3 automatically on your iPod at the time when you synced it. So when you were in traffic, you could listen to something. And then, yeah, same with social media. I just love kind of playing around, having an idea, seeing what we can implement fast and then learning from it. And I found in everything I've done, like a reverse correlation between how much thought I put into it beforehand and how successful it is. I find the ideas that I really put a lot of thought into and planning and get advice around before I launch end up being more conservative and not, not as interesting and don't do as well. And then the ones that are just like, it'd be so cool if this thing existed, or the— for me have been the biggest breakthrough successes in my career.

What's an example of something that you put a lot of thought into and got a lot of feedback and then it didn't go anywhere? Yeah.

So actually, uh, alongside doing my own podcast, which I put very little thought into, it's like, how can I get one episode up? Yeah. I had this idea to launch a podcast advertising platform where we could dynamically insert ads into podcasts and run an ad network. This is back in 2005. So, you know, in retrospect, 10 years too early. There are companies that have done this 10 years later and been very successful with it. But yeah, I did a lot of research. I had a whole huge Excel model on how the economics would work out at scale, even though we had barely any revenue. And we actually, you know, built the, you know, we actually built the software for this. Like we built, I think, I think it was the first ever dynamic ad insertion into podcasts. But yeah, a lot of thought into it. I got lots of people's advice on it. But then I just, it was just like hitting my head against a brick wall. There was just no market for it back then. And so I kept trying and trying and, you know, asking experts for what, what could be done and talking to other entrepreneurs about it and writing up pitch decks and running it by people. And the market just wasn't there.

Yeah.

And then I compare that later on to, uh, Muck Rack, for example, where, you know, same guy doing both of them. I mean, I had a lot more experience by then, but looking back, I mean, the main differentiator was just, you know, the market was there. And I think there's something about it, like when the market's there and you don't have to contort yourself for it, um, it, you know, kind of pulls you in a way. And And I think if you are just, you know, love the field that you're in, if you love the internet and you're on the internet or whatever, you know, probably the same for coffee or anything else. You know, if you're drawn to it, um, you'll be more successful.

Yeah, I can see that has worked for you. You know, I read that you have said most of the things I tried failed, but the cost of failure was low. But I would say for many people, the ego cost of fail— of failure is high. So have you ever had concerns about failure? Do you ever like beat yourself up or worry about it?

Oh, 100%. Yeah. I'm not immune from all the emotions you'd imagine. I found the hardest thing about it. I mean, there's two things because at least I find when I go into a business, I like contort my identity around that business, which, you know, retrospect, probably not too healthy, but, uh, and it's, and maybe less so now as I round it out, but especially in the early days and, you know, my teens, my early 20s, it's like, hey, I'm going to launch a podcast ad network company. I am the podcast ad guy, you know, a podcast entrepreneur. That is who I am. And then, you know, after a year or two of it not working and seeing that you need to pivot, it's like, not just, okay, we got to get away from this. Business, you know, it's also like I have to— okay, I have to untangle my entire identity from it. I think I got better at that over time, but that was one, uh, you know, really big challenge with the ego in it. And the other is, you know, it's so funny, when I was doing my podcast early on, I talked to all these entrepreneurs who at the time were a lot older and more experienced than me. One of the biggest pieces the tech entrepreneurs would give me as advice is like, The worst thing you can do is be too early to the market. And I was always thinking to myself, yeah, old man, whatever. I'm going to figure out how to make it work.

Okay.

So, you know, just, yeah, exactly. Okay. Boomer. So, so despite, um, despite being in, you know, at the time, probably the best opportunity of anyone to get advice from a lot of top entrepreneurs as I was, I had to learn it the hard way. And there was a big part of me, cause you know, you read the books about the people who like, have to push and push and push, and then it works at the very last minute. So you kind of get it, you know, you, you know, your ego can lead you to believe like, okay, well, if I'm as good as I think I am, I can just make it work. And, you know, it's a humbling moment to realize that part of your job as an entrepreneur isn't just to make it work, but to test assumptions in the marketplace and realize your assumptions might be wrong. Doesn't mean you're a bad entrepreneur, just means you have to pivot your idea, right?

Actually, that's a fantastic way to look at it. I think that the most healthy way to think about, especially early stage when you're building something, is I'm doing an experiment, I'm testing my assumptions. And when you think about testing your assumptions, it kind of cushions the blow of it not working out and the ego risk.

Yeah, well said. And actually, I, I kind of learned that lesson a bit because by the time we did, uh, the Shorty Awards and then Muck Rack, um, we'd launched we called the company, the holding company that didn't do anything aside from try ideas, Sawhorse Media. And we came up with the name just because I was looking around our office and we did this little trick to save money on desks where instead of buying a desk, you go to Lowe's or Home Depot and you just buy two sawhorses and a door. A door is like $20. These plastic sawhorses are really cheap too. You throw the door across the sawhorses. So, you know, we just needed a name really quick to incorporate so we could get going.

Right.

And that actually, in a way, kind of lessened the risk. Cause unlike any idea, like with the Shorty Awards, with Muck Rack, I mean, I told you the quick version of the story, but we actually launched a dozen other ideas simultaneous between Shorties and doubling down on Muck Rack. And by this point we kind of perfected it. We were like, you know what, we're just gonna try to because their website, I mean, this advice wouldn't be good if you're going to open, you know, a coffee shop that you have to sign a 5-year lease for, like, then you should sit down and do the math.

Don't do that.

And all that. Yeah, exactly. But, you know, if you were in a position like we were, where it's like, hey, we know we can build websites with the people on our team. We know we can get them out in a week or two and just see how the concept does. We were like, you know, let's just launch as many as possible. We're not even gonna think about the business plan. We're not gonna model it out. We're not even gonna get advice because if we screw up, you know, it's just 2 weeks of time that we lost. So we kind of got into that mode and, you know, everything from the corporate structure to the ego structure made it so that if an idea or an experiment didn't work out, no big deal. We move on.

Yeah. Very elegant. I love that. Well, as you said, MuckRock was a success. And my understanding is that you never, you've never taken VC money, that you bootstrapped bootstrap the whole way. Was that a conscious choice? Was that just, again, you experimenting? How did that happen?

Yeah, that's correct. And it was a conscious choice. You know, it wasn't— we weren't— you know, there's some people who are like religious about it. VCs are evil, we're never going to take VC. We weren't that way. I mean, I think, you know, I don't begrudge Twitter and Facebook and Google. Like, it worked out great for them. Sometimes VC's right. But for us, you know, we saw that we had this business model with SaaS where you can, you know, you can really get the revenue from the customers. There were a few times actually where we thought to ourselves like, hey, should we go out and get VC and turbocharge and all that? Every time we did, we're like, well, you know, to raise venture capital, at least at the time, and probably still, although I hear it's easier now, but at least at the time, it's like, okay, you got to drop everything and spend 3 months doing nothing but raising venture capital., you know, going out there and pitching and refining your story and dealing with the rejections and the long-form paperwork. And, you know, there's so much that goes into it. And each time we thought, you know what, what if we took those 2 weeks and just tried to get more customers? Or sorry, 3 months, uh, and then took, tried to get more customers. And each time we're like, well, that sounds a whole lot better because then we'll have more revenue. So the company will be more valuable and we'll still own the whole thing. And so he kept doing that. And in retrospect, um, you know, really grateful that we did, uh, for a whole bunch of reasons. You know, one is that it's great to control our own destiny. Uh, my co-founder and I own the vast majority of the company, and, you know, the board of directors is the two of us having dinner every month. So we're, we're able to make decisions quickly and then take all that time that we would have taken with, um, board management and dealing with investor egos and all that and, and put it into the company. Yeah.

Also, I mean, it just seems to me that you then don't have the pressure on you of outsiders who want a certain outcome in a certain amount of time.

Yeah, it's well said because we've been doing it now. I mean, we launched, uh, the free version of the website in 2009. So it's like a dozen years ago. And then the SaaS version in 2011. So, you know, still a decade ago. And the average VC time horizon is 5 to 7 years. Uh, but looking at it now, like we've created the most value in the last couple of years because it's, you know, we've been growing fast and the, just the nature of compound growth, you always create the most value in the last couple of years. And I always think to myself, if we had an investor who had a 5 to 7 year time horizon, as every VC does, not because they're bad people or impatient, but just because that's how the fund structure is set up and that's how their investors are expecting to get paid back. We would've had to do something, sell to a bigger competitor, as many of our contemporaries did, or found some other bigger VC to come in, or maybe we'd just taken some weird moonshot bet to see if we could have gotten bigger sooner, and it might not have worked out. And then we'd have hired a bunch of people, laid them off, and you hear these stories all the time. And instead, I mean, it's been very low drama. We've never done layoffs. We've never just done— I mean, we make mistakes. We build products, features nobody sees, but we've never had like, make it or break it bet on the company that could have led to catastrophe because we didn't need to and just steadily built value.

Right. That's, uh, I mean, it sounds so relaxing the way you put that. Like you can just sort of do things at your own pace. And then to your point, you're, you know, you're managing your co-founder relationship, but managing your board is kind of very drama-free. But I'm just curious, have there been any cons to that decision for you? Would you say any downsides?

I would say the biggest downsides are, you know, in retrospect, I don't think it was bad for us, but it takes a lot longer to hire executives.

Oh, interesting.

So it was just like a lot of years of my life of like just dealing with a lot of, you know, I dealt with a lot of things longer than somebody who took VC would have, you know, for example, like doing the financial projections. I mean, I figured out how to do it, but I don't have a finance background. It wasn't until a couple years ago that we, we got to the point we could afford to hire a CFO who's excellent. And now he does all his financial forecasts much better than I did. It's just a huge weight off my shoulders. But had we raised VC immediately, we would have hired a CFO, or at least, you know, someone, someone to do the the forecast. And same with, you know, getting an experienced VP of People to deal with all the HR issues that, you know, there are many years where I was the de facto VP of People, assisted by someone else on my team who'd never done it before. And we're just figuring out like, how do you— should you use a PEO or not? Just all these basic things where if we'd raised VC in the early days, we'd have hired someone and they just instantly instantly know, yeah, here's what we do about, you know, all these policies. There are so many things we learned the hard way where the second you get a professional VP in, it's just like, oh, this is how it's done. I'm like, oh wait, I stressed for weeks and tried to figure out how to do that for so long. And it's just like, oh yeah, they're professionals. They would've known exactly what to do.

Right.

So it was all that, you know, pros and cons too, because I got to learn a lot. And I think, You know, one of the things I think a lot of people don't realize is a lot of, uh, you can only learn so fast. So I think, you know, I have no idea, like, if we'd scaled from, you know, 1 people or 1 person to now we're at over 100. If we did that scaling up in 2 years, maybe I couldn't have cut it. Maybe I wouldn't have figured it out fast enough. But it was nice to learn one step at a time over 10 years, going from 1 to over 100 people. Uh, and same for a lot of our team members. We have a lot of homegrown people who are now, uh, leading departments or, and, you know, holding senior roles and have jumped around the company. And many of them might not have made it if we just scaled up super fast. So there's, yeah, there's pros and cons to it all. It's hard to look back and know exactly.

Right. Well, you'd never know exactly, but what I'm hearing you say is that there was like the pace that you underwent by, you were forced to undergo because you just didn't have all the VC money to throw at problems. It forced everyone, including you, to go a little slower. To go actually a lot slower. And that gives you time to learn. It's like, that's actually what big companies do for people. It grooms them, it teaches them, it gives them context and structure. And it sounds like you had that inside of Muck Rack just as it was growing.

Yeah, it's well said. And it gave us time to develop in our market. And, and, you know, that can be good or bad. Like for us, in, in retrospect, we've proven that, uh, th— this is a long-term market. There is time to grow. Grow. It wasn't like a, you know, a quick winner-take-all game. So I think we benefited off that. Also, now, I mean, still the majority of our sales comes from inbound and word of mouth. And you can only make that grow so fast because it just takes a while to build a reputation and have people refer you, everything like that. So, you know, for us and in the dynamics in our market, it worked out. You know, for Coinbase, like, yeah, crypto came out of nowhere. They probably needed the VC to, to grow up as fast as they are. But a lot of markets, you know, you don't know how long they'll take to develop. And I just always think, like, I've seen so many good businesses just blow up because they were just 1 or 2 years too early to the market, and they just got so much pressure from investors that, you know, it ruined things for them. So, you know, I really encourage people to think about time horizon. I almost wish, you know, VCs would restructure themselves to have some ways so that if it, if it took 10 years or 15 years instead of 5 years, they could, they could roll with it and not have it kind of, uh, become a headache for them the way that it does now, because some businesses just take longer and there's nothing wrong with that if it ends up being a huge outcome.

Right. You know, when you talk about the time it took you, so you've, you've, it's a 10-year journey, right? Muck Rack's been around for 10 years. Is that right?

Yeah, yeah, 10 years since you became a software platform.

Yeah. And so in that period, you've had your own journey of growth. That's what I'm always so curious about. Can you talk a little bit about how you've grown as a leader? And when you talk about giving you the time to learn the things you needed to do, like, I'm just so curious about that whole trajectory of growth for you and the things that you've noticed in yourself and you grow as a leader.

Yeah, there were several different phases to it. One was just learning how to manage people as we were starting. I was like, just starting to really learn that. And honestly, like one of the biggest, one of the hardest parts for me was I'd never really been an employee.

Yeah.

And, uh, I just kind of assumed everybody was like me and was super entrepreneurial.

Right.

So it took me a long time just to figure out like why someone would want to be an employee instead of starting their own company. Why they ever want to work for me instead of starting their own thing. And in retrospect, it's like, oh yeah, it's the paycheck dummy and a million other things.

But most people are actually like that.

Yeah. A lot of turns out a lot of people like a paycheck and knowing that they'll get paid in 2 weeks, you know, versus, uh, I always felt like we were kind of staring down the barrel of a gun and not knowing, like, will we have, um, you know, we have enough money in 2 or 3 months to keep going. And I, I was able to live like that, but a lot of people can't, uh, for a whole variety of reasons. So, you know, one was just kind of learning that and the basics, you know, training people, talking to them about their career, creating an environment where they, you know, they feel safe and productive. Then kind of next level, like having more experienced employees, because early on, like we were just hiring people out of college and teaching them. We didn't have the resources to be hiring experienced people, but then When we were hiring more experienced people, or even like the people that we'd hired early on got more experience, it was then another transition to learn like, oh yeah, this person probably knows more about their function than me, so I got to give them a little room and kind of paint the bigger picture for them and maybe just not automatically assume I know better. And then even now, you know, it's always a, it's a continual journey. So, you know, now we're at the point where like everyone who who reports to me has a whole department of their own that they're running. So it, it's a totally different style of leadership I need to bring.

Right.

And it was really shifting. Um, you know, I, I love the concept for this podcast cuz I always say like the, the way I always think about it is first of all, like the, the skills that it took to start the business had nothing at all to do with the skills to be the CEO of the business, even though it's, you just automatically get the CEO title when you start it because, you know, you can print whatever you want on that first business card. So, you know, that was a huge shift. And then I— a lot of my friends ask me, like, am I bored after 10 years of doing this? But I always think, like, I really get a new job, like, about every 2 years because every 2 years we more than doubled. And, you know, even though the job title is the same, it's totally different. You know, being the CEO of a 2-person company has nothing to do with being the CEO of a 10-person company. Being the CEO of a 10-person company where you kind of know everyone and can manage everyone directly has nothing to do with being the CEO of a 30-person company where you have reporting layers and you can't know everybody. And then being the CEO of a 30-person company, it's totally different job than CEO of a 100-plus person company. So I feel like there should almost be different titles for it because it's kind of ridiculous when you think about it. The person who starts a company this morning gets the same job title as Tim Cook at Apple. That's a good point.

Yeah, they should, they should like, it's almost like levels, like CEO 1, CEO 2, right? So everyone kind of can see where you are.

That's right. Yeah. Yeah.

Greg, how would you describe your leadership style now? And, and I guess I would ask you to maybe compare it to even like 2 years ago or 5 years ago, just to give a sense of what your job is today versus what it was in the recent past.

Yeah, so I think my leadership style, a lot of my leadership style has been similar in that, uh, one thing I recognize, certain things about my personality that I think I, I've just learned to use an asset as an asset in my leadership style rather than think of it as a liability. Like I've realized like I'm very bad at anything that has to do with consistency. So it's like, hey, there's something that should be done every week to make sure this business runs well. And there are plenty of things like that. I just hate that. I'll procrastinate it. I'll begrudgingly do it. I'll find excuses not to do it. And then I found through hiring people pretty early on, like, oh wait, there are other people who love consistency in their job and they hate dealing with uncertainty and creating stuff out of nothing. So when I find those people, I'm like, oh great, you take over this, you do the thing that has to do with consistency. The thing that has to do with process. And because of that, I always like being kind of very hands-off, giving people a lot of space to do it, which can be good and bad. I mean, overall, I think it's really good as long as you find the right people who have a lot of ambition and passion for it. But I found I don't work well if there's someone who has to be micromanaged or checked in with. I just won't check. I'll forget to check in with them and they'll be off my email for weeks. Because that's consistency. Yeah, exactly.

Right.

Uh, so, so that was one really, one really big thing. And then, you know, in terms of kind of evolving my leadership style, I think it's gotten much more about kind of switching into kind of a coaching mindset. Cause early on it was still like, hey, I know how this business works better than anybody else. Let me tell you, you know, you messed that up or you spent too much money on that, or how do we do this? Um, quickly till now. We're, we're at a point now where everyone that we're hiring, uh, that reports to me, or, or that promoted that reports to me, knows more about their functional area than me. My CFO knows more about finance than me. Our VP of People knows more about, uh, you know, running a people organization and HR practices than myself. We just hired a VP of Legal, and she definitely knows much more about legal issues than I do. So, you know, across the board, it's like, it should be that everyone knows, knows more than me about everything. So kind of shifting much more of my time and even the product, like when I go into demos, like now I used to know the product cold because early on I was doing a lot of the product work along with my co-founder. Now I log in, it's like, oh, there's some feature that launched 2 days ago that I've never used. And you know, someone else even knows the product better than me, which is something I would never thought I would say.

Yeah.

So it's kind of learning, hey, it's much more about like setting the vision, thinking further off. And then when I'm talking to my reports, like going at it much more from a coaching mindset, like how do I help you be better? How do I help make sure that we're aligned on the vision? And a lot less like, hey, what are you doing this week? Let me, you know, you could have done that better. Let me show you now. Yeah. And that, and that takes a while to get used to. And, and you know, there was a long time, yeah. One of the biggest switches for me, just as I'm thinking back now, I'd kind of forgotten about this, but I remember I used to go through days, I'd get caught up in internal meetings and, you know, doing my one-on-ones with my reports. There's so much internal stuff. I didn't get any work done today. At some point I'm like, oh, wait a minute. Maybe, maybe I did. Maybe this is my job. And you know, my job is actually to talk to people at the team. And, and that was kind of a revelation for me. Cause I used to feel like if I wasn't talking to a customer, closing a deal or shipping a product, I wasn't doing real work. And then it's like, oh, wait a minute. The real work is everything that I thought wasn't the real work. And the stuff that I thought was the real work, I shouldn't be doing because I should be delegating it to someone who knows what they're doing.

That's absolutely right. But I'm curious also, did that come with any mourning? Because a lot of times, you know, I work with CEOs or, you know, founders growing into CEOs who they're product guys or they're sales guys, right? Or, or, you know, whatever, wherever they come from. And it's actually really hard for them to give up that thing that they loved, right? Or technical founder who is growing into a CEO and has to hire a VP Eng and a CTO. Did you have any of those feelings of regret when you began to give up the things that you'd really started the business in the first place?

100%. Yeah, I had, I mean, there was just such an adrenaline I always got from shipping a product, you know, being there, wireframing it, like watching it go live, emailing the first few users and knowing that I controlled a big chunk of that. A big adrenaline rush I would get from like working on a deal myself and, you know, going through the initial meeting with the prospect and going through the, you know, getting the yes and the legal commitment and seeing that through. And yeah, I was kind of just always built for that kind of adrenaline rush, uh, you know, to now where it's like the features launch that I haven't seen before they launch, or maybe I just saw a product review of them, but it's all done on its own. Or I'll see a new customer, you know, big deal gets closed and I hear about it after it's closed. Maybe I saw it in a pipeline review, but I never talked to the customer. I didn't personally contribute to that particular deal. And there is some degree to where, I mean, I gotta admit, like when I see that big customer just come in, I mean, there's a certain degree of satisfaction. It's like, oh, that's nice. We got all this extra revenue. I didn't have to do anything for it, but it's nowhere near the feeling of personal pride and accomplishment that I got when I was the one working on it. And there were definitely moments then, and there are even moments now where it's just like a quiet day where all I'm doing is coaching people on internal meetings and kind of almost because it's the, it's almost like this weird irony I find, like when the business is running really well, in a way I feel like less personal satisfaction because if it's running really well, I kind of don't have to do anything except for just the basics of my job of, you know, one-on-ones with my reports and the team meetings, dreaming up what we're going to do in 2 years and setting the vision and preparing for our all-hands. So when it runs well, it's like sometimes I almost feel unsatisfied, whereas when something goes wrong, when there's something, a feature that didn't work right and we got to prepare the plan for it, or a tricky contract issue that no one else knows how to handle. I mean, this doesn't really happen anymore at our scale, but even a couple of years ago, tricky contract issue no one else knows how to handle. So I would jump in and work on it and figure out a creative solution to get the deal done. Yeah, I'd feel this accomplishment, but then— and feel good, but then I'd reflect on it and be like, oh wait, the only reason I had to jump in is probably because we hadn't yet hired a strong enough leader here. It's like I fixed the symptom, I didn't address the cause. So yeah, it's this weird— it's just so weird psychologically. That, you know, in a way it's like, yeah, the better it runs, the less needed I feel. And whenever I do feel needed, it's probably because I didn't hire right or I didn't plan right. Or, you know, maybe it's just that we're growing and we just now have to figure out the solution, but the solution is something other than me, you know, jumping in and doing something.

Right, right. So, I mean, I guess I would ask you, how have you come to terms with that? And what advice do you have for other founders as they go through their growth journey, how to come to terms with a lot of the adrenaline rush you're talking about and also having to step away from those things that give you that satisfaction?

I've taken up cycling, do long-distance cycling. And, uh, but I said kind of half-jokingly, but seriously, like, I, I just found, like, I got, you know, one thing I realized kind of getting— doing this for a few more years is that it's really— I used to always think it was a sprint. You know, I'd see a competitor launch something or see a weakness in the business, like, oh man, we gotta, we gotta get this out in 2 months or it's checkmate and our competitor wins and we're toast. And, and, you know, either we, we fix it now or we screw up. And, and then the longer we've been doing it, I've seen like it's actually much more like a marathon. If we can keep doing it for a long time, we build a tremendous amount of value. And yeah, like in this example, We sold it 2 years ago, the company would have been worth, you know, much less than half of what it's worth today. So it's like the marathon of going from 8 years to 10 years is worth more than the whole first 8. It's such a weird thing to wrap one's head around. But to do that, like, you can't sprint for 10 years, right? You know, one was I kind of gave myself a bit more permission to like, yeah, not not work on the weekends, pick up other hobbies, whatever, pick up cycling, pick up travel, have a bit more fun. So that's definitely one element of it. Another is just recognizing what I just said that like, hey, if I'm sitting around bored today, like take a moment to just be satisfied that like the company's running well, be grateful for all the great people that work at the company and that are that are doing the, you know, doing the work that means that I'm not jumping in and doing it. You know, connect with other, connect with other founders I found was great. That was part of my motivation for bringing back the podcast and, you know, just hearing how other people have done it. And, you know, I do have to say, I don't want to make it sound too bad. Like, it is fun to learn new things. So every year it's like, okay, what does A couple years ago when we hired a CFO, I mean, I didn't really know before that. I didn't really know what a CFO did. I mean, I kind of knew they balanced the books and did a financial forecast, but it turns out there's all these other things you rely on a CFO for. I had no idea. I remember I sat down with the CFO of a company that's since IPO'd who got just to ask him like what the hell he does. Oh, I had no idea. All these parts of my job that I thought the CEO had to do and were a big pain, turns out the CFO does that. And if you hire a CFO, you don't have to deal with that anymore. And in fact, they should do it better than you. So, right. Uh, yeah, you know, and I just, and I find continually when I, you know, as long as we're growing, it's like there's always something where it's like, okay, how do we figure out how to do this next thing? You know, you know, even for us, like we're still not the size of I was talking to a friend who has a much bigger company, you know, that already has like a matrix system and we're not that big yet. So it's like, oh, at some point I'll have to figure out how to do a matrix system. So that'll keep, you know, that'll keep me learning.

Yeah. Forever matrix will keep you learning forever. Take my advice. Don't go, don't go fast, go slow on a matrix system.

Just to say that.

But did, how do you, do you set yourself also learning goals? Like if you think you talked about becoming more of a coach and becoming more of like a, you know, sort of a supporter. And I'm just curious, how do you learn? Do you mostly learn by just talking to people, or are there other ways that you sort of get your education and advising from?

It's a combination. Uh, I'd say I never set kind of formal goals, but it's more kind of systems and putting myself in the right place. So a lot of it is networking. I'll really try to seek out people who who had grown their business to the next level ahead of me and learn from them. And sometimes, you know, rarely I find it's like a formal mentoring thing. Often it's just like having friends batting ideas back and forth and, and learning along the way. You know, same, you know, sometimes it's even functional executives like, hey, we're not able to hire the person in this function at the next level yet, but let me just meet an executive who's doing it at the next level and buy them lunch and just hear how they've dealt with these situations. Books I found are still really big, especially early on. Like, I remember one of my favorite books is High Output Management by Andy Grove, the former Intel CEO. I just remember reading that early on. It's like, like the idea. I mean, it sounds so obvious now, like just doing like regular one-on-ones with my reports. Was like not on my radar. And I read that like, oh, that makes a lot of sense. I've got to set up regular one-on-one meetings with my reports. And surprise, surprise, it made my relationship better with all my reports. I mean, he has a lot more advanced stuff in that book too. So I found all that. I also joined professional organizations like Entrepreneurs Organization, Young Presidents Organization, where I've been able to get in forums with like-minded entrepreneurs where, you know, it's more of a peer group, but we would all push each other and bring in guest speakers and all that. I found that very valuable too. So yeah, just kind of piecing it together every which way I could.

Mm-hmm. Mm-hmm. Now, one thing that you, I think, instituted early on in your company, maybe even at the very beginning, was this notion of remote-first work. And that, I'm sure you grew into that and then we had a global pandemic, and then I think you went remote forever. You signed the, what is it called? The Work Remotely Forever Pledge. And I think you yourself, are you still in Miami right now?

That's right, we're still in Miami. And we not only signed the Work Remotely Forever Pledge, we created it and got a whole bunch of companies on board to join with us.

Oh, I didn't realize you created it. Wow.

Yeah, it was a lot of fun, a lot of, you know, and companies that are bigger than us probably even did more than us to pioneer it, like Matt Mullenweg over at Automattic, the makers of WordPress, and InVision all signed it too. So we're really proud to bring such an amazing group of companies together.

Yeah, that's incredible. Well, I guess I'm curious, I mean, you know, you were an expert in remote work before there was even a pandemic, and now everyone's dealing with it. What, what are your thoughts about the ways to think about managing remote workers, and what advice do you have?

So it's funny, but before the pandemic, we were, we were kind of half, half remote. So half our team was distributed, were just people working from home in cities we weren't in. Then we had a beautiful office in SoHo, but we decided, like a lot of companies that were like us, they were like, okay, well, if you're near headquarters, you gotta come in because we spend all this, you know, we bought this beautiful headquarters.

Right.

But we were like, well, you know what, if some people are working fine, totally remote, like It'd be hypocritical to force the people who happen to live in New York to come in. And, you know, even we have people who live in Greenpoint, it would take them 45 minutes to get from Greenpoint to SoHo on crowded subways. So early on we were like, okay, well, we'll have an office in New York, but you don't even have to show up. And it was so funny because a lot of days less than half the people would show up.

Yeah.

Whenever my other CEOs would come in and they'd walk into the office and it's half empty, They'd look at me like, uh, is everything okay, guys? I'd be like, oh yeah, yeah. You know, everybody's working. They're just working remotely. And everyone's like, how do you know if they're working if they're not in the office? And my response is always, how do you know if they're working if they're in the office? You can see someone at their desk, but you don't know. They could be checking Facebook. They could be, even if you see that they've got a spreadsheet open, or their email program open, they might not know what they're doing. They might be wasting all day because nobody set up a, you know, gave them a goal or, or set up a KPI or properly trained them. So our philosophy is always like, if you're going to bring someone on, you should be managing them by, you know, with goals, with key performance indicators, KPIs. We're big on OKRs, you know, getting people objectives for what they're going after, you know, training, setting up systems to, to check in with people. So, you know, our philosophy was always it should, even when we had an office, we're like, it should be irrelevant if they come in, because you should set up ways to, you know, to monitor performance and to know where people are headed without them being in the office. And, you know, I actually think it's an asset not being in the office with someone because we've all had that awkward situation where it's like, you know, hey, we've got, I'm making up a name, Joe, you know, we have Joe on the team, you know, has Joe hasn't hit his goals. We don't quite know what Joe does, but, you know, he comes in early and he stays late and everybody likes him. So we can't get rid of Joe. We can't put Joe on a performance improvement plan.

Yeah.

But it's like, no, you know, like if they're not performing, you gotta let them go. And, and, you know, the office almost biases you and vice versa. Let's say you had a, a top salesperson, you know, again, to make up a name, Juliette, and Juliette comes in at 10:00 AM because she, you know, drops off her kid on the way to school. And leaves at 3 PM because she likes working from home in the afternoon, but she crushes her sales goal. You know, she doubles it. In an all-office environment, everyone's be like, yeah, you know, she's hitting her sales goal, but like, it's bringing down morale. We can't have the top salesperson walking out at 3. That's bad for everybody. You got to tell her to stay till 6 so she sets a good example for the rest of the sales team. But it's like, No, her job's to sell. If she hits her quota, nothing else should matter. Nothing else should matter.

Mm-hmm.

So it's just like these things are just unpalatable in an office environment due to human dynamics, like all go away. So like we have no idea how many hours our, our salespeople are working and we don't care. You know, we could set up software, like some people do that monitoring software where you like get the screenshot and it's like, what program, how many hours are they spending in Outlook or Salesforce or this or that? We don't do any of that because it's like, who cares? You know, if someone can double their sales quota and work 4 hours a week, you know, to use the name of Tim Ferriss's book, that's awesome. You know, I want to train everybody else to work that way.

Right. That's a good point. They should work the fewer hours and achieve the maximum of their goals. Right. That's a great point. And I love the way you frame that, especially like, how do you know they're working? They're in the office and this whole notion of FaceTime. But I guess I'm curious, how do you think about culture? Have you thought about culture with MuckRec? Have you thought about culture either the sort of days you were hybrid and now the remote? What do you think about that?

Yeah, I think culture is key. I mean, to be honest, we— I think we have an excellent culture. We've had almost no, almost no voluntary turnover in the last 12 months, you know, during this time that like everyone's reporting like the Great Resignation. And, and, you know, we've been growing quickly and getting a lot of new employees through referrals. Uh, so it's gone well. I gotta say, like, I was never someone who used the term culture for the first several years because I was just like, you know, we, we gotta survive and, uh, and all that. But, you know, in retrospect, there were lots of things you were doing that was culture. I just never thought about it using those words, and now I do. Uh, yeah, that's one of the things I've learned. But we found there's a lot you can do to build a remote culture that can be as positive, I think, as what you do to build an in-person culture. You know, a lot of it is like being very transparent on Slack. We share, you know, all the metrics about the company's revenue, you know, most of the big technical decisions, how we deal with customer decisions, all that are in public Slack channels anyone can go look at. We were big on using Zoom prior to the pandemic. It was like every one of our rules was like every meeting has to have a Zoom link because you don't know who's going to be in the office that day. Because otherwise what would happen with a lot of companies that were hybrid, in a way hybrid is the most challenging because like people who aren't at the mothership feel excluded and it's like, oh, hey, Alisa, we got to tell you about this decision that got made around the water cooler. Sorry, you weren't there. You were in this other city or you didn't show up to work that day. I mean, you didn't, you chose to work from home that day and now this decision's made. So we were always like, you know what, we're not going to have, we'll talk to each other by the water cooler as we had the espresso machine about what we did that weekend, but we're not going to talk business there. We're going to talk business at the pre-scheduled meetings that all have a Zoom link. And it used to be that, you know, there'd be a conference room that you could click into Zoom. In a way, it's gotten a lot better since the pandemic because now everyone's on equal footing. In fact, people who are in different cities told me that they preferred working for us during the pandemic because they used to feel a bit like a second-class citizen because you, you click into the Zoom and we invested a lot in AV so the remote person could have the best possible experience, but it still sucks to click into a meeting and see 5 people are in the room and you're out of the room.

And especially during lunch, let's face it, when they bring the sushi in, it's like you're just not going to have the sushi on Zoom.

Oh my God, we did the stupidest thing, which is we used to have birthday lunches for everybody. Oh, and so we'd have the lunch at the office, so then we had— we invested all the, uh, equipment so people could tune in virtually to watch us eat. And at the time it seemed logical, like, oh yeah, we're having this lunch here and now we're gonna make it so you can tune You know, zoom in too. But looking back at it, it's like, how stupid was that? How bad was the experience to anyone tuning in? And then it only got worse as we got bigger, because it's one thing to look at 5 people, you know, through a camera. You can at least see what everyone's up to. But it's another thing to look at like 50 people through a camera, all eating lunch, where you could barely, barely see each person, and you're watching them all have a good time eating. Whereas now it's like we still do birthday, well, we had to shift because we got too big. We still do group meals, but it's like, yeah, everybody has a way to expense the delivery to them and everyone's on their own Zoom camera. And now you're on equal footing, whether you're in New York or San Francisco or Italy or Warsaw or Argentina, as we all have among the many places we have our team.

Yeah. So one thing you said, as you were talking about what you learned as a manager and also the remote culture, you talked about how if someone's not doing their job, you have to fire them. That's just the truth. You have to let them go. I'm curious, when are the moments that you've realized, oh, I have to fire that person? And what was that like for you to learn how to do that? That's a hard thing for everyone to do.

Yeah. And I wish I was working at some other company and I had to fire somebody while I worked for another company and could have been shown how to do it. But unfortunately that wasn't how it played out for me. Yeah, for me. And another weakness or a strength I have as an entrepreneur is just, you know, unbridled optimism, which can sometimes be a weakness as a manager. Cause I'm just always optimistic. Like, yeah, I know the person's made the same mistake 5 times, but maybe if I just tell them a different way. They'll figure it out. So I remember the first time I realized I had to fire someone. It was someone who everybody liked, was a friend of a friend, how we hired the person. So, you know, I felt extra accountable for wanting to make it work. And, you know, it's just one of these situations where like the person was well-intentioned, never quite got it. You'd always ask them to do things, never quite never would get it done right, would get overwhelmed with things they shouldn't get overwhelmed with. And just so many things in retrospect were like the writing was on the wall. Despite that, I probably took 6 months. It was probably the difference between when it was clear that this person needed to be fired and when I could work up the nerve to fire them was probably 6 to 9 months. And it just felt almost surreal to me. I'm like, Oh my God, how could I actually walk into a meeting and make it so this person doesn't work for me anymore? Like, it just sounds crazy now. But yeah, it's just, you know, really hard to like think like, yeah, I'm going to walk in and tell them they're fired. And then just, I had to talk to friends of mine who'd done it before, just figure out the logistics. Like, are they, what do you say? How much room do you leave for Q&A, if any? Do you immediately walk them out? Like, She had to deactivate their email account during the meeting. Like all these weird, you know, all these very kind of morbid logistical steps that it takes to fire someone beyond just like saying the words. That was, that was a big learning curve for me, uh, first time I had to do it. And then, you know, I, I saw myself having to train. We had a lot of homegrown managers, so I then had to train for them and show them how to do it.

Can you remember, like, if you knew for 6 or 9 months this person wasn't going to make it, And there was a moment where you actually were going to go do it. Can you remember what shifted for you, which you realized, okay, tomorrow is the day, or like, okay, next Monday?

Yeah, I would say, you know, just kind of over time slowly dawned and compounded on me, like, this person needs to go, you know, just each time more and more egregious examples, you know, again, nothing against the person. I know they've succeeded in their career since in different areas, you know, different fields, but just was not a match for the role. It's just so obvious. And I remember like talking to people and then just, you know, and then I just remember like procrastinating, like, okay, well, maybe today's not the right day because you have this customer meeting and so-and-so's starting, so I'll do it tomorrow. And finally I was like, okay, we've got to do it. And, you know, part of it being bootstrapped too, you're always staring down that, that cash flow and knowing that you need to put it to work. So I just remember, yeah, picking the day, scheduling when we were going to do it, also scheduling a huddle with everyone else right after, because there's also like a dynamic where you have to make it clear to everybody else, like, hey, we fired this person for performance. The company's not in trouble. You know, those early days where that, that wouldn't be clear. And, you know, we're going to fill it again. And I also thought like, oh, everyone's going to be so disappointed when in reality everyone's like, yeah, of course you had to do that. And now even though everyone liked the person, like, yeah, now you don't have to cover for that person. We can get the right person in the role.

Yeah.

So yeah, just like a lot of logistical pieces that, that had to go into place. But yeah, at some point, like everything else, I just, you know, finally chose a date I was going to do it and stuck to it.

Yeah, a lot of people dread that, and then they find that everybody else has been just waiting for this to happen, and they have been covering and kind of working around this person.

Totally. And I do have to say, you know, when I was looking into it, I read a million places like it never gets easier firing anyone. And I've got to say, and I want this to sound callous, like it's still super hard to fire anybody. And I hate, I hate doing it. It's the worst part of my job, even now past 100 people. I do have to say the first firing is the worst, you know, like it's definitely like if you've never done it before, like it's just the first one. And particularly if you're an entrepreneur and your organization has never fired anyone, like, I don't know, it's just the worst thing in the world. And like after you've done it the first time, it's still not easy. It's still painful. You know, I've still had weekends ruined over it, you know, anticipating that I got to fire this person., the coming Monday. But, you know, at least once you've done it once, like, you just know how it goes and you know what to say. And it's something you can build, you know, it's like a painful action that you can at least build a muscle to deal with, right? But that first time is just brutal.

Yeah, it's— you're not alone. It's really brutal for people. You know, Greg, you are so— you're so open and you're so— I feel like, um, you know, comfortable with the things you're not as good at, right? And sort of comfortable having made all these mistakes. I'm just curious, have you ever experienced self-doubt or imposter syndrome in your journey, as your entrepreneurial journey, in your journey to become a CEO? Have you ever experienced that?

Oh, all the time. Yeah, yeah, definitely. Um, you know, a lot of it, like, early on I viewed myself as a scrappy entrepreneur, uh, You know, I kind of had dreams of being a, you know, the company being huge and running it, but I, you know, I was never quite sure, like, yeah, could I really be the CEO of a larger organization? Or, or is it that I'm just good at starting the thing and then got to find some CEO to run it and then I'll just run off and start another thing, which by the way, there's nothing wrong with. And I have a lot of friends who, who are just serial entrepreneurs. They keep a good chunk of equity each time. And, you know, some of them made a lot more money than I have. But yeah, I never kind of knew like, yeah, could I really step into the CEO shoes and run a large organization? And it gets intimidating, particularly bringing on, you know, like I said, people who know more than me about their area. And it took a while to adjust to that. So I'd say, you know, that was one of the big areas. Another was like I kind of had, you know, in retrospect, like some kind of fixed viewpoints. I remember early on thinking I was just like bad at negotiating, uh, and I just had that in my, my head, you know, my track about myself. And I remember like after, you know, like the 100th customer contract we negotiated, like it wasn't until pretty far on that, uh, you know, I was training other people on our team how to negotiate customer contracts. Like, oh, wait a minute, maybe, you know, I'm not the best negotiator in the world, but, you know, I've gotten decent at negotiating. And then it occurred to me like, oh yeah, most people aren't born knowing how to negotiate. It's just a learned skill. And yeah, I sucked at it early on because, you know, the first time I had to negotiate a legal agreement, I had, you know, no experience and no training at it, but I got good at it over time. And I found that about a whole bunch of different skills that, like, you know, things I'm bad at to start because I had zero experience and then kind of worked that into my self-image. And then at some point I have to reassess, like, Oh, I've gotten good at that. I can notch that off. Or, you know, and then there are other things like the consistency thing where like, I've just like, okay, I actually don't want to get good at that. I just want to figure out how to compose a team so that I'm balanced out. But also, I don't need to be good at that to be successful in my role so long as I build the right team.

Right. But when you were— so, I mean, I get that. I also appreciate that you sort of, as you said, like embedded this narrative into your self, like the sort of imposter narrative or the self-doubt narrative. But then you sort of stepped back and then you were able to change your story, right? To reauthor your own story. But in those moments where you were having the imposter syndrome or self-doubt or feeling like, "Oh, I'm not good at this," how did you handle that?

Yeah, sometimes in very unhealthy ways and just throwing myself into work or making it work and kind of burying it. So I can't say I had the, you know, always the most healthy journey with it. But, you know, never went off the rails either. But yeah, I'd say, you know, sometimes that I found journaling helped a lot, just writing down what happened. Sometimes just writing it out helped me untangle things. Actually, another big thing that helped was joining a peer forum. So first through Entrepreneurs Organization, which I highly recommend, uh, and that which is modeled after YPO, which is basically the same thing for larger companies. And the model that they have is they put you in a forum with other entrepreneurs and CEOs, like 6 to 10 other people, and it's all a peer forum. So you're not allowed to give advice. The idea is you're all at the same level, but you give these extremely candid updates about what's happening in your your business. And one thing that surprised me about it when I first joined was also updates about your family and your personal life. And we all go around and give it. And it was, um, you know, it was so powerful just being able to say, and the idea is you say like the best thing and the worst thing. And you're supposed to say, you know, when you say the worst thing, it's like the worst thing that you would not say to your, definitely to your employees, but maybe even to your friends and all that. I found just being able to go out there and say it. And then like, I remember like there was early on the company, I was worried if we'd have enough cash to make it through our slow season in the summer. And I just remember feeling like so ashamed about it. I'm like, how could I not have managed the cash right? And you know, I must be the first, most irresponsible person in the world. Who else could this have happened to? And then I go into the forum and I share that and someone else is like, oh yeah, I hear you're having cash flow problems. Oh yeah, that's a word for it. Like, there's a word for it, cash flow problems, because I guess it happens to other businesses too. It's like, oh, wait a minute, like, cash flow is one of the biggest headaches of any small business. And it was just like, the second I was able to step out of it, just, just reframing it from like, oh, you know, we've got— going from like, oh shit, I mismanaged a business, we could run out of money, to like, we have a cash flow challenge. Just, you know, it's two, you know, two ways to describe the same thing. But like, it's so Well, I was just like, oh, a cash flow challenge. Like, oh yeah, this is a challenge that a growing business has. Because when you grow a business, there's cash flow challenges and you figure it out. And there's strategies I could go through what's in my control. So, um, so, so yeah, I just found like having that, that outlet and, you know, I think it's all the same thing, you know, journaling, journaling, being at a forum, uh, having a coach. Um, All those things, you know, where you just say, you know, express what the issue is, frame it productively, really helps the growth. And it's just so easy as an entrepreneur to kind of get stuck in your own head and bury the problem and not talk about it.

Yeah, totally. And I love what you said, like writing it out and telling other people, it brings it into the air. And then you talked about being ashamed. You know, the thing about ashamed is that we have these secrets. It's like we can't tell anyone. And then it festers inside of you as a secret that you're ashamed of and that you're hiding. And there's so much emotional baggage to that. And then when you say it, first of all, it does actually get better. You're like, it's not as deep and dark. And then other people are like, oh yeah, that's a thing. I love the way you frame like, yeah, cash flow problem, of course.

Well said. Yeah. And I found it, it's like this big distinction because I knew a lot of entrepreneurs and I'd hang out with a lot of entrepreneurs early on. So I had lots of great sources of advice. But when you only see, you know, a friend who's an entrepreneur for an hour, you know, you catch up with them once or twice a year, you don't go deep. It's just, oh, how's everything going? Everything's going great. I, you know, I'm trying to figure out this small edge issue, but like to actually get into like the deep existential issues of your business like that, you need, you need a particular space for that. So that's one thing I encourage people, even if you have advisors and mentors, Finding the space where you have someone, and it doesn't have to be— it's great if it is a mentor, but it doesn't have to be the best mentor in the world. It could be a peer, could be a coach, but just having that space— could be a journal even— but just having that space to really figure out what your issues are is very important.

Yeah, yeah, totally. Um, what else? What do you wish you had known earlier on your journey, Greg?

So many things, you know, I think a lot of it was that to really figure some, so many challenges are like a who challenge rather than a what challenge. Somewhere early on looking at parts of the business that I found daunting, like how could, like when I was doing the HR early on, I'm like, how would I ever do this if I had, if I, instead of having 10 employees, I had 50, or how would I ever do this financial model? If instead of having a couple million in revenue, we had tens of millions in revenue. And I would always look at that daunted, thinking like, how am I ever going to figure this out? And then looking back, it's like, oh wait, the answer was just, you'll never figure that out. You're just going to hire the person who knows how to do that because that's the crux of their profession and trust them and coach them and make sure they're really good at, you know, have checks and all that. But like, that's someone else's job, you know, the same way that if I, um, you know, had a cavity, I'm not like, how am I going to learn how to drill my cavity? I'm just going to get a recommendation to a good dentist.

Right.

So yeah, that, you know, that would have made it, I think I stressed a lot about all these kind of edge areas, the biz or, you know, functions within the business where had I known how a larger organization functioned, I would have just known like, oh, you know, all I got to do is figure out like, how can I cover this for the gap? Between now and when I can afford to hire the professional that really knows how to do this job function.

Hmm. That's very wise. Yeah, I would— I think I like the way you put the idea that like, it's so daunting until you realize it's actually a person who can cover that thing, who actually knows how to do that. And I love your analogy of the dentist. It's so true. Is there any other advice that you have for founders? That you want to share or anything else you want to say?

Yeah, I'd say, you know, I think a lot— I think we're at a crazy time now. I mean, it's awesome right now. It's like so easy to raise money. It's— you hear everyone celebrating these businesses for like, it was founded a year ago and now they've got a $100 million valuation or a billion dollar valuation. Everyone celebrates the unicorn as defined by it being young. And growing, getting the big valuation really fast. But I think there's a lot to be learned that a lot of these journeys take a while and you've got to set yourself up to have the patience for it. And then you think about the companies we all admire, Intel back in the day, which in turn inspired Steve Jobs with how he ran Apple and which in turn inspired Google and then Facebook and these just enduring companies that built a lot of value, or Berkshire Hathaway. The companies we all admire are these ones that take a long time. And so I think, again, I'm not against anyone raising money, and in many situations it makes sense, but I just encourage people to really think it through. Don't just go for the dollar. Think through What capital structure do you need? How long do you think the journey will be? Are you working with people that you want to spend, you know, 10 years of your life with? And just be very, you know, thoughtful about that in the early days, because the people you get on your cap table, you know, the investors you have in your business, the people on your board, will really dictate the trajectory of your company. So I think you have to be very careful with that and not go for the quick dollar if you want to set yourself up to build an enduring business.

Yeah. Amazing. Greg, so wise. And thank you so much for joining me today. This was such a great conversation. I know everyone's going to benefit from it.

Thanks so much for having me on. This is, this is really fun. And I, I love that there's a podcast dedicated not just to how to start a business, but actually how to, how to grow it and how to step into the CEO role.

Ah, thank you so much.

Good.

It was so good to talk to you. Thanks for listening to From Startup to Grownup. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alisacohn.com.