Psychology of Successful Entrepreneurship: John Kerber
15 May 2025 · 57 min
In this Dream Big Studios podcast, host Christian Brim interviews Jon Kerber, founder of HooFi, a software platform for community spaces such as libraries, parks, and museums. Kerber recounts the 12‑year journey from his first venture, Who’s on My Wi‑Fi, through a series of pivots, major wins (state‑wide library contracts, UK expansion, reaching 1,600+ libraries), and low points (a failed Indiegogo launch, a million free‑user freemium model, a router product that flopped). He reflects on the psychological traits that helped launch the company—disliking being told what to do, over‑working, ego, and blind spots—and how those same traits became liabilities as the business grew. The conversation delves into his 20‑year partnership with co‑founder Luke, describing their visionary‑integrator dynamic, trust issues, and conflict‑resolution style. Kerber discusses the difficulty of defining a target market, the importance of solving problems in the customer’s language, and the role of peer networks (EO Forum, local startup community, the 404 coworking space) in shaping his leadership, cash‑flow mindset, and willingness to delegate. Throughout, he emphasizes self‑awareness, humility, and the ongoing challenge of modeling behavior for a growing team.
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All right, Christian Brim back here from the Dream Big Studios. I have a wonderful guest today, Jon Kerber with HooFi. Welcome.
Hey, Christian, how are you?
I'm great. Thanks for coming.
Great.
Yeah. So give us the 2-minute version of Jon Kerber and HooFi.
Yeah. So as far as HooFi, you know, we do software and tools for community spaces, right? So libraries, parks, museums, we make it easier to manage a community space and also stay connected with their community, with their patrons. So think like a calendar of events, registration and reminder emails for somebody to go to an event, booking the meeting rooms. We also do this thing with wireless statistics so we can see like busy times of day and collecting stats and things like that. So basically, a lot of the tools that are out there for community spaces are not very good. And we just kind of came in there and said, you know what, we're going to, we're going to make this better, you know, so that it's easier to run a community space because I used to run a coworking space, The 404. Okay. And I ran into all those problems with that. And so it just kind of, you know, it was sort of like half solving my own itch and problems that I had when I was running my coworking space that ultimately shut down.
Right.
Right. So trying to make it easier for other people like me effectively. Yeah.
Yeah. Well, that's how a lot of great businesses get started is scratching your own itch.
Right. Yeah.
So, so how long have you been doing WhoFi?
Yeah. So I left Paycom in 2012 and, and it was that summer that really like launched WhoFi. And so yeah, so it's 2024 summer. So it's solid 12 years, which is nice. I mean, that's, That's a solid decade.
Plus some. So what are some of the highlights of that 12 years?
Oh, I mean, that's what's kept me engaged the whole time. It's like there's so many different things that are like new highs during the whole process. So I mean, one of our big wins was getting the State Library of Ohio to, you know, basically use the Hoofi service in all the public libraries across the entire state. Nice. And that was in 2016, 2017. And that was awesome. And then we kind of continued with working with different states that would provide it to all the libraries and kept getting those until about 2020. And then of course COVID hit, right? And so we were just doing the wireless statistics. That's what we started off with.. But then when COVID hit, you know, I was kind of looking around, talking to our library customers, and it was like, you know, did everything just change? Right? Because suddenly, I mean, we could see in the Wi-Fi stats drops of 70 to 80% usage of the space. And what we saw was, you know, there were some places, right? There were some places that they kept going, right? They started doing like Zoom story times. They started, you know, and so basically just decided that our role would be to document, one, the Wi-Fi statistics drops because we thought like, this is just fascinating. This is a once in a lifetime situation. And we just need to like track this for, if nothing else, just to show up on like a History Channel one day about usage because we could see it. We could literally see in our data like what was happening. And then two was we wanted to share like the people that were, that we were talking to that weren't, that didn't look like they'd been hit by a truck or didn't seem like they were, they were excited. They're like, oh, you know, now we're doing these videos on YouTube and now we're having more people show up this way. And, you know, kind of all the things that people kind of who successfully navigated COVID were doing. And so we started like blogging about it and telling people about it. And then, and then that's when it became more apparent, you know, again, some of the other tools that were out there, you know, yeah, there were calendar programs, but they weren't like making it easy to share a Zoom link. And this is like what everything was. And so we just started kind of down this path of like, well, you know, the, you know, the events have changed, right? Like people's expectations of being in-person or virtual have changed. And so that was a big win too. Like when we basically kind of pivoted from just the Wi-Fi to doing like calendar and meeting rooms and all this, you know, with, with kind of a focus on you know, the hybrid element of being in person or virtually to almost everything that people do now, you know? And so, you know, that was kind of our second, well, it was kind of a major pivot in 2020 from that. And that was a big win. And then, you know, I mean, then there's been big wins along the way too. Like a most recent one is we just opened up a HooFi UK. So we opened up a subsidiary in the UK and it was because the University of Glasgow Caledonia, they wanted to start using our Wi-Fi statistics, but now they're interested in like the meeting room management and all that. And so, so that's been a big win too. So it's kind of our first international, you know, library and university that's using us. So, so that was a win. I mean, getting to like, I mean, getting to our first 1,000 libraries was a win and then, you know, now we're at about, I think we're at like 1,600 or 1,700 or something. And it's just, you know.
That's impressive.
Yeah, I mean, you know, opening the new office was a win, you know, getting to 10 people was a win. I mean, like these all felt like wins along the way, you know? And so it's hard for me to say like a single.
No, no, that's great. So what were some of the low points?
Oh man, low points. So, you know, we originally started off as a who's on my Wi-Fi, you know, security app.. And, you know, this is some of the same technology. And, you know, I would say, like, I very distinctly remember year 3 because year 3 was when we actually got to like a million free users, right? So we got to a million, you know, think everything should be amazing. However, a million free users literally don't pay anything.
By definition.
By definition, right? So, so,, you know, we were— we— I'd read all about the freemium and, you know, all those kinds of things, uh, you know, with a million free users, think about the level of support and questions and stuff like that that comes in from that. Uh, and we were making $30,000 a year between my co-founder and I, and it was just like so painful, right? So this is circa 20— let's call it 2014 or something like that, 2015. And, and, you know, my co-founder and I had basically just like What are we doing? You know? And, and we'd launched a router. We'd taken on a little bit of investment money. We had an employee and launched the router. Router fails, right? So because we thought that was like another thing. And so, I mean, literally around— I mean, I want to call it, you know, let's call it like February of 2015. I mean, this thing is teetering on just absolutely shutting the whole thing down, right? Because my co-founder and I were like, What are we doing? The guy who built the router is like, well, this didn't work. And that's why, you know, and, you know, we— because of the free users. Well, okay, so let me just stop there. So this thing's teetering like we're about to— it's about to just shut down. And my co-founder and I literally have the conversation of what are we doing and should we just shut this down? Right. And, you know, the one kind of the kind of spark of it was I don't know if you know Danny Maloney is from Tailwind. A really good entrepreneur in Oklahoma City area, tech entrepreneur. And, you know, I was telling him about what was happening, you know, because what was happening with all those free users is we were getting— I mean, we were getting, you know, 100, 200-something signups per month, right?
Okay.
And then we were churning 180 signups within 2 months or 3 months. So we had this like constant setup process and everything. And Danny and I were having lunch one day and he basically was just like, So, John, have you ever looked at the people that don't churn? And I was like, what do you mean, Danny? He's like, you know, you've got, you know, you've had thousands of people or you've got millions of free users. You've had thousands of people pay for the premium product. You know, most of them leave. I'm like, yeah. He's like, have you ever looked at the people who don't? I'm like, no, Danny, I never, I never thought that. Right. And so, and so when we, when we analyzed it, there were basically like groups of people, it was banks and libraries. And, you know, it was like, this is weird. And then we called them up and we're like, hey, you know, yeah, you know, John, who's on my Wi-Fi, saw you using our paid product. What are you doing? Why are you using it? And, you know, for banks, they still saw it as a security tool and they were like, well, it's just low cost and, you know, the security is okay. But like, if it catches one guy eventually, cool, then it was worth it.. And the libraries were different and they were like, you know, it's not— we're not using it for security, we're using it for these like wireless stats that we have to provide to the state and all this kind of stuff. And so they wanted something totally different. They wanted privacy, they wanted all these kinds of features. And my co-founder and I were just like, man, this seems like a good, like a good mix, you know, like this seems like this would work better. And so you know, we, we talked to them and, and then just started pivoting the product that way. Right. So then that's, that was how we, you know, became Hoofi and that was how we started working with libraries. But it was literally in this moment of like 2015, the company's teetering, the security company that was originally planned is failing. You know, Luke and I were like, okay, we've got 12 months to make like $5,000 each, right? So like when, when you and I can make $5,000 apiece, this thing can continue, right? And so, and then that's what happens. So we literally put like all of our energy into postcards and emails and all this kind of outbound to libraries. And then that's when it, that's when the whole thing kind of shifted. But so, so that was definitely a low point. Yeah. You know, an early employee leaving, product failing, pivoting for sure out of money. Like it was just like that was an absolute low.
When we discussed you doing this interview, you were a little resistant at first. Sure.
Why? Yeah, so I think it probably comes down to a couple of different things. So the first is that a little bit how you framed it was that you were talking about the psychological makeup of entrepreneurs.
Right.
And I'm not super excited about anyone having my exact psychological makeup. Right. So that's, you know, that was That was one concern. And then the other concern was just that, you know, I've definitely been around film and video and audio recordings and stuff since I was like a teenager. And certainly it's usually better to have edit control than not.
Yes.
I guess I would say so. So it just kind of— when it was sort of framed as, I'd like to dig into your head and dig into the psychological makeup of you as a person and your history, it's like, you know, and so that was concerning. And then the other concern was just things like, you know, certainly have already seen times where things get recorded and you think it's like thrown away, but it's actually not. And then you see it years later and you're like, oh my gosh, you know, what was I saying there? Right.
So, well, so let's talk about the psychology of an entrepreneur. So We've covered a lot of ground on previous episodes, but the thing that keeps surfacing for me is this concept that the character traits that make us disposed to be an entrepreneur, to start a business, those character traits can become liabilities after the business is started, right? And the idea of being self-aware to know that you, the individual, the entrepreneur, are the business's problem. Yeah. Right, so a business has, lots of problems. If it has employees, it's got people problems. You have customer problems, you have competition problems, you know, all of these things that every business has. But the one that I think that is often overlooked— I definitely overlooked it for a long time— is my effect on the business and how I was potentially limiting the business. Not potentially, definitely, because of the way I showed up, my behaviors, my biases, prejudices, whatever, thought process, feelings. So can you talk about that?
Sure. So as far as kind of like my behaviors, which are also, you know, what would lead me to become an entrepreneur and start my own company and do things like that. And then how those turn into liabilities. Yeah, I mean, think about it for just a few seconds. I mean, as an entrepreneur, one thing was I didn't like being told what to do very much. I still don't really— still don't really enjoy that.
No.
Even when other people have way better ideas, that's, that's a problem, right? So started, started off as, as a reason to do it, right? But then can definitely be an issue because, you know, as the company's grown, I'm not the expert in everything, not even close to it, right? Other people become the experts. And when I don't take the advice of the experts that are on my team, that can be a real issue. Yeah, that's one thing. I was kind of in the hard worker, achiever camp or whatever. So I would want to take on a lot of projects and effort and do stuff till 8:00 at night, whatever, to get things done. But then— and so that was a positive because that helped the company and the product get off the ground. But the liability on that is either A, I expect other people on the team to behave in that same manner, or B, I don't delegate enough because I'll just like, oh, I can just do it. I can just throw 5 minutes, you know, I can just, I've got 10 minutes, I can do that. And then literally, I mean, I find myself still in situations where like other people on the team are waiting on me because I've thrown too much on my plate because I just think that I can, you know, and that's definitely a liability.
I think for me that showed up in two ways. One, I had this expectation of work. Like I had to, work hard, right? And that's different for everybody. But like, I had an expectation of myself of what I needed to bring to the table, right? If it needed to get done, I had to make sure it got done. But, you know, the thing that I realized was for me, the flip was when I always felt like I was having to pull everybody along, right? I was the workhorse and they were just kind of getting dragged by ropes behind me.
Yeah.
Was when I felt like they were actually taking the lead and going in front of me. Like they knew where we were going.
Yeah.
And so they went ahead and passed me, right? Yeah. And started doing the things to get to where we needed to go. And I was like, Holy shit. I, you know, I can't tell you exactly when it was, but it was in the last, I don't know, 2, 3 years that it was like, oh, wow. I didn't believe that was possible, right? I thought that if something happened, had to get done, I was the one to make it happen.
Oh, yeah. Got it. Yeah, I luckily Luckily, because I have a co-founder who's like a college friend of mine from 20 years ago and we played rugby together and everything. Let's just say we don't pull any punches in our conversation. So, so, you know, bottom of the scrum, nasty stuff happens. Yeah, because I've heard that before, but it hasn't been my experience as an entrepreneur. And I think a lot of it is because Luke has been able to be like, 'Hey, Jon, you're being a jackass,' right? Like, not, you know, in a very friendly, professional, but we've known each other for 20 years and quit being a jackass way, right? Like, he's been able to, I think, point out some times when I'm doing that and like, 'Jon, why are you not— let that guy go, right? Let him do his thing.' Yeah.
You guys have been together, friends, for 20 years. You've been co-founders together for 12. 12, yeah. That seems to me, my experience, fairly unusual. What would you ascribe the success of the partnership to?
Yeah, I don't know. I mean, being totally honest, I have no idea, except that We're very different people, right? So he and I have very different views on a lot of different things. We have a different skill set. So for example, I tried to start a company, I mean, when I was like 20 or something like that. And I have an engineering background and I tried to start with another engineer and we were constantly stepping on each other's toes and doing all that. And, you know, he'd do something, I'd redo it, I'd do something, he'd redo it, you know? So let's just say that that project or idea, I don't know if it failed because I think he ended up just doing it himself. But that's kind of how that— definitely us working together wasn't going to work. And, and I tried to launch some like different products and stuff on my own, but clearly I have massive blind spots and things didn't really kind of take off. And, and really, I mean, he was in a situation where— so he has more of a sales, operational service type background. I mean, at one point he was managing like 4,000 people for kind of a mega-cap type company and he got fired from this major corporation that he wanted to like work at for 20 years. And it— well, he didn't even get fired. He got downsized, right? His layer of management was no longer needed. Yes. Like, are you kidding me? You know, so, and so hilarious and I was just talking to him and I was like, and he was then very upset about the whole corporate, you know, mega company, don't care about people kind of thing. It's like, you know what, you're right. You should join me and I should leave and we should do this thing together. And this, you know, it'll be great, right? And of course, that's where I went. And it just kind of worked. I mean, it's, you know, I kind of like to say if we were a mountain climbing expedition or something like that, like I'm the guy who's pointing at the top of the mountain like, hey, we need to go there, you know? And Luke's the guy who's like, John, that's great. No, yeah, we got to go there. You see that big ravine you're about to lead everybody into? Like, let's go around the ravine. I'm like, it's right there. He's like, yeah, yeah, I get it. Let's go around the ravine.
So he's— it's more of a yin and yang, more of a visionary integrator dynamic.
Oh, 100%.
Yeah.
100%.
Yeah. And I think that relationship, that dynamic of The visionary integrator is, well, I mean, they wrote a book about it.
Is it the Rocket Fuel? Rocket Fuel. Yeah.
Yeah. I mean, because it is rocket fuel if you can find that person. Yeah. For me, that was a challenge because I didn't want to let go of the operational, right? Not that I was particularly good at it, It was, you know, when we first tried to implement EOS, we did it ourselves. We didn't bring in an implementer. Yeah. And it failed. And it was only after we had hired a professional implementer and been doing EOS for a year which was probably 4 years after we had tried it, I really began to get some insight as to why it failed. And it was a— I describe it as a gut punch because what— there were some small things, but the big reason it didn't work was because there wasn't any trust. And that trust showed up, that lack of trust showed up. It was reciprocal, right? I didn't trust them, they didn't trust me. Yeah. And that was a gut punch because I would have told you that there was trust, right? Yeah. And I think for me in my journey, honest self-assessment. Visionaries tend to be focused on the mountain and miss the ravines, right? But it's also about not just the external factors of what's going on, but me, myself. So, yeah. Is there a point in your partnership where besides the, you know, I don't know, this thing's going to work, we're going to have to shut it down. Sure. Has there been a point where your partnership didn't work or there was conflict that you— I mean, you know, that was challenging?
Yeah, I mean, not yet, I guess I would say, because it's the— and I don't know, like the people that I'm closest to, and that's, you know, my co-founder, my wife, my brothers, my sisters, we kind of were skirmishers. And maybe this is just me. Like, I don't—
I don't know. Rugby, you're saying?
Well, no, no. Yeah, right. Well, what I mean is I don't let things build and then explode generally. My personality type and the personality type of the people that are very close to me, when something's wrong, they say it then. They might give you a day. They might not do it in public, but like, it's, I mean, within that day, like if you're doing something stupid, they're going to say it. And if I think they're doing something stupid, I'm going to say, like it doesn't build up into a list of, Grievances. Grievances over time. And we tend to hash it out. I mean, I won't go into any details. I mean, we were literally talking about something on Wednesday that was like a miss that I thought he had and a miss that he thought I had, you know what I mean? And we weren't mad. It was like, well, you know, you know what I mean? And things can get like a little elevated. Right. But then it's like done. Because it didn't build up. It was, hey, why did you do this on Monday? How did—
why?
Oh, hey, why was this going? You know, like, boom, done. You know, and we've done that. We've done that for a long time. Right. And that's why I said, because we've known each other so long, like, he's not afraid to pull any punches with me. Right. I'm not afraid to pull any punches with him. And so I think it gives a lot more insight because what I like to say, and this is definitely— this is my belief of this, is that Who's on My Wi-Fi was a company that I imagined I built, had a co-founder kind of come on, but then absolutely collapsed that I didn't listen to. And really, WhoFi is the company we built together, right? Which was that like, you know, that was library community space focused. You know, we were doing different marketing stuff that he wanted to do, some sales stuff he wanted to do, some customer service stuff I wanted to do, some product stuff that I wanted that he would like, you know, There literally would not be WhoFi without my co-founder, right? There was a Who's on My Wi-Fi without him, right? To some degree.
You know, you just said that you started it and it was your idea and it failed and then you pivoted. Yeah. Was there something that excuse me, had to change in you or for you at that point beyond like the market dynamics of like these are the people that are actually using it and I need to focus on them.
But like, yeah, well, that's, that's a really good question.
I like to ask good questions. Yeah.
I mean, no one's ever asked me that, but I would say 100% yes. And what I mean by that is You know, who's on my Wi-Fi and the router failing, I would say was probably the first massive big failure of my life. Right? I mean, I mean, like, yeah, hey, did not achieve everything. Not your first screw up. No, plenty of screw ups. Right. But like, but like, this is what I told everybody I was going to do. This is what I quit my job and left to do. This is what like I put all my eggs into this basket and it failed. Right. And, you know, I was, I was crushed by that. But then there was also— and this is what I did not expect from it, you know, especially because just, just a little bit of backstory on it. I mean, it was— we launched it on Indiegogo, right?
Okay.
So Indiegogo, A unique thing about it is that it's 30 days, right? And you know if you're not going to hit it within day 2. And so literally on day 3, this thing was like toast and rumblings were in the company. They said one of the guys was going to leave. Everybody flew in. I mean, this is kind of a big thing. And this launch just completely bottomed, right?
Cratered.
And there was nothing I could do. There was nothing I could do for 26 more days, right? And so it was a very like, the first week was just like, oh my gosh, I can't believe this, you know, all the things that go through your head. I'm an embarrassment to myself and my family and whatever, right? But then you get to week 2 and it's like, well, I guess I'm just gonna sleep, you know? And so, 'cause I don't—
You don't have anything else to do.
Yeah, there's not really much else I can do. Stuff was still coming in from the other stuff and still having conversations, but I'm gonna rest. And I finally took a rest, and it was kind of like— and then at the end of it, I would say it was just kind of like a full acceptance of the failure that had actually just happened and that that was okay. And that not only was that okay, But that, you know what, those other customers again, we were making like $30 grand, but like they mostly didn't even know about it because we'd done such a poor job of marketing the launch to it. They still had other things. Our, you know, like my, my wife still loved me. My kids had no idea. The people that were using it for some other thing were still using it for some other thing. And so even though it was this thing that like I'd built up and the team had built up and we'd built up and it was big in our minds, in my mind, and it completely failed. Well, I mean, for the most part, everyone just kind of goes on, right? And it's not really as big of a deal. And so I would say that was a big shift for me just to like recognize that. But it was very humbling, right? So I definitely had some arrogance and ego. I mean, you have to almost to launch a company, right? So it's very humbling.
I say delusion, but okay.
Delusion. Fair enough.— it was very humbling to fail like that. But also it wasn't, you know, not fatal, right? And so it made me a lot more receptive to, like, quite frankly, other people's ideas. And I would say that, like, you know, probably if that first idea had succeeded, but the way even Luke and I's partnership was, if it had been from that idea, which was originally my idea and I'd done some of the work, like it would have blown up later. You know what I mean? It would have absolutely cratered later from my blind spots that if I wasn't listening to him, you know, but we had succeeded kind of on the security space. Does that make sense?
Yeah, but I mean, I would even push back that it was a failure because if you had not done that work, you wouldn't have found the libraries.
100%. Right. Yeah. Well, and that's, that's what's so tough about it too, because when people ask me about like finding a market or finding your product market fit, you know, we basically gave away our product for free to a million people to then, which was awful, to then find that there were like these small groups of people that thought it was amazing. Right. You know, the masses thought it was garbage, but like the small group of people, it was something they were looking for and didn't exist.
Right.
And And those people really valued it and really thought it was great and have really, you know, kept us for a decade.
And I think that's a critical point that people need to hear that, you know, you had this idea.
Yeah.
Right. And you thought it was very widespread applicability.
Yeah.
It wasn't that you had the wrong idea. It was that there was just this smaller subset of everyone that actually needed it and would pay for it. And I think that's one of the traps that visionaries and entrepreneurs get into is they see all of the possibilities, right? And for me, what that looked like was, I had a real hard time defining a target market. Yeah. For many years, I thought I had a target market, but it was way too loosely defined, even the way I had it. And I mean, to the point that I guess I was resistant to it subconsciously, like I wanted, to be— I wanted to be for more people, right? But that's the exact opposite of how you get traction, right? Yeah.
Yeah. I mean, yeah, I couldn't agree more. You know, it's, it's funny because now, now 10 years later and 8+ years in libraries, you know, now we're looking at a second market, right? Right. Like after, you know, now at several people and an office and a product that is well-defined and works and, you know, and now it seems much more obvious. It's like, oh, well, it turns out this can also work for universities. But that was a decade of builds and improvements and business processes and everything to get all of it to a point to where, yes, it could actually handle additional people beyond this narrow scope. Right.
Yeah. And I think that's a classic. I think it shows up in the tech space more quickly or easier. It's easier to see, but it's applicable to every business is not just knowing your target market, but what the problem they have in their terms. So for existing businesses like ours, that becomes a real challenge because you have all of this baggage that you're dragging along, all this history, all these biases, your perceptions of what the customer thinks, right?
Yeah.
And you know this is what they want, right? But at the end of the day, that's what business is about, is solving people's problems, right? And they're willing to pay you money for it. So if you're not real clear on what the problem is that you're solving in their terms, not your terms, then you're gonna struggle with growth.
Yeah, no, I completely agree. I mean, um, it's kind of like, uh, I'm not really much of a golfer, but my son plays golf and I've kind of started to pay attention to it. And it's the— I feel like it's the, you know, golf is a good analogy for business, right? Like, it doesn't matter how, how much effort, how much work, how much strength or speed or any of that that you may have naturally, or even that, that you put into it, it's really about how well you hit the ball. Because like, if you know, and the more dead on you hit, right, what the— what the— who the customer is, what their problem is, how they want it solved, and the price they want it solved for. Like, if you hit all those factors, that's hitting it dead on and it goes straight and can fly. And it doesn't matter if you're 6 years old, you'll, you'll knock it past a 72-year-old with, or 40-year-old, whatever, with all the experience in the world that doesn't solve the problem that well. Right. So, right.
Yeah. And then you can add things like strength And speed.
Then you can do that. Right. But if you don't. Yeah, 100%.
So you've had some experience with EO Forum. Yeah. Has that— how has that contributed to your personal growth?
Yeah, that's again, a really good question, Christian. Thank you. Good question. So I think what I could say is just a little bit of a story, which is that after about a year in EOA, I was like, I don't know if I'm getting anything out of this. You know, it's nice and it's fine and everything, but whatever. And I was talking to my wife, right? And she was like, well, I don't know what's going on there, John, but 'You just seem better.' You know, like, interesting. Like, she was basically like, you know, 'You don't seem as wrapped up in the company. You don't seem as agitated. Like, you just seem better and like happier.' And—
but you didn't perceive that?
I didn't perceive it at all, you know. And it was actually another guy from EOA, Andrew Cross, that I was having a conversation with the same thing. And he said that to me too. And he was like, And I was like, ah, you know, I don't know if I'm getting much out of this or whatever. And he was like, and he was like, John, when you showed up on day one, you like had your laptop bag with you, like you were about to check support yourself during breaks or something. And then look at you now. You showed up with a pencil and paper. Right. Right. You know, so, so, you know, it's kind of like from a business leader standpoint or business owner standpoint, you know, delegation and forcing myself to let go and all that, like that, that had such a profound impact on me because, you know, that was the thing I didn't do, right? I didn't take chunks of time and like disconnect from the business regularly.
So would you say that it was—
That was massive.
Skills that you acquired through that, or was it like being around other people and seeing how they behaved or what? Like what?
It's all of the above. Yeah, it's really both. And so my EOA journey was 5 years basically. And, you know, there was such an aspect of skills. And again, because I go back to my blind spots, like I had, you know, so my thought on running a company was, oh, startups are supposed to burn all the cash so that, you you can grow as fast as possible, right? And I know you're laughing, but that's literally what I thought, right? Because it's like, oh, because it's a risky part of a portfolio or whatever. So that's what all the investors say. It's like, you know, you just burn all the cash. Okay, that's great if you're VC funded, right? If you're bootstrapped, that cash is yours and it like burns out real quick, right? So I'd made that mistake. And so it was actually, I think it was you that pointed this out, right? That like, you know, my earnings at the end of every year were zero or negative. And then amazingly, we didn't have any cash to grow with. And it was like a weird, you know, and, and that was just looking at my financials in year one. And that was— and, and that sounds basic, but that was actually so profound for me and for us as a company because then once we had earnings, then we could reinvest them, right? Then we could like take chances and do things and either hire the person or not hire the person or try the marketing or try the, you know, buy the equipment, whatever. To make everything better, but without that, like earnings or cash just literally to use, then where does it come from? And that's what had happened. That's why we joined EOAs that, you know, had grown but then had stagnated. And this was even before COVID kind of did a number on a lot of the community spaces. So, so that was a skill, right?
Right.
But then the other side of that was You know, so when I joined the 404, so I didn't actually start off as the owner of the 404. I was just a member going there. And I remembered thinking like, you know, I was the only guy in Oklahoma City doing a startup. That's what I was thinking in my head before I found it. But I kind of found that Oklahoma City startup community and that was very helpful just in and of itself to like, you know, there's other people doing this or, you know, and they've got the same crazy and it's, you know, so, so when I joined EOA, it really felt like I just kind of hit the next level of that because mainly in the startup community was a lot more very, very early stage, you know. So if somebody was making $50 grand, you're like, oh my gosh, how did you do that? You know, right? You know, or you go hit the EOA and it's like all those companies are at least a little bit established. They at least have a customer, they at least have a market. They're making revenue. They usually have at least some amount of employees, right? You know, to just, you know, and so it kind of just felt like the next level of that. And so, you know, that's hugely impactful anyways, because I also found that in EOA, I mean, and probably in EO as well, like everyone has their own different skill thing that they're awesome at, right? I mean, whether it's— and it's probably not what you're awesome at, right? So learn so much more about, you know, people who are good at marketing, people who are good at sales, people who are good at finance, people who are good at like operations, people who are good at product, you know, like everyone's got their thing that has kind of taken them to this, to this level. And can just rapidly learn from them. So I would say it was, again, and that goes back to skill. But then the emotional side was like the, because we all share the same crazy, right? That when I'm in my crazy that other people don't understand, it's like, Well, so-and-so would get this. Yes. So there's a very, you know, it's sort of like there's technical or skill type things, there's learning from others. And then there's also just kind of the, yeah, this might be a little bit off what I'm doing, but I'm pretty sure like he just did that too. Or she, you know, like it's— you see what I mean?
It's the— I call it the tribe. Yeah. It's the people that share the same overall values. Yeah. That, you know, get you. And they, you know, they may sit there and look at you funny and say, well, you know, I wouldn't do it that way. That's not the decision I would make. But you at least know that they've been there to have those types of decisions and have to question them, right? Yeah. I think the thing that's interesting about what you said was, is what I see in my own journey has confirmed this, is that we all reach these— Drew Goodmanson calls it these entrepreneurial inflection points. And it's different for every person in every business because there's too many variables. But this inflection point is when the entrepreneur realizes that it's beyond them.
Yeah.
Right? In whatever capacity, that might be time, that might be money, that might be skills. They come up with a problem that they can't solve, right? Yeah. And, you know, depending upon the problem, you know, it may be that the entrepreneur has to grow themselves to change themselves in order to facilitate that growth. Or it may be where, you know, the entrepreneur says, I've taken this as far as I can go. Someone needs to take it further and having the humility to say that. But that's hard. Yeah. That's hard. Yeah. It's hard for me because I'm like, I think I can do anything. Just, you know—
Grind more.
Right.
Exactly.
Yeah.
Yeah. Yeah. I mean, it's, you know, I'm trying to think of how to articulate it.
In English, please.
Yeah, I won't bust out Spanish. It'd be embarrassing anyways. But yeah, I mean, there's definitely a lot of value in seeing other people who are in similar situations either go through problems that you haven't realized yet, right? Or struggles that you have had experience with. And I mean, whether, you know, if I'm the person that, you know, I'm hearing about somebody else's problem and they're talking about it very candidly, and then when it eventually hits me, right? 2 years later, 3 years later, whatever, I'm in a similar situation. One, I know who to talk to. Two, I've already like, you know, I'm like, yeah, I figured this would happen, you know, eventually, right? Like, it's not caught us off guard as much. So that's been massive. But then also the, like, when I see somebody who's in the exact same situation that I was in, Right? And never to give advice on it, but just like—
How does advice work?
Right, right. But like, literally that happened to me, right? And this is how, this is why I did it even worse than you're talking about. But this is how I finally got out of it. Maybe that helps, right? Yeah.
Because like you pointed out, you don't want to be told what to do. And I think that's a common characteristic of entrepreneurs, right? I remember sitting at EO's master program and one of the speakers, there's 80, 50 entrepreneurs in this presentation. And he looks at one of the guys on the front row and he said, will you get me a cup of coffee? And the guy just kind of balked. Yeah. And he was doing it as a teaching moment 'cause he knows us, right? But even something so simple as, "Hey, get me a cup of coffee." It wasn't, "Can you get me a cup of coffee?" Right? It was, "Get me a cup." If someone tells me what to do, like my wife, I've had to train her. Like, "Can you ask me?" Because it's not that I don't wanna do it, but as soon as you command it, it just— That's what happens.
Spikes come out.
Yeah, right, right. I don't get that about my personality. I don't know why that is. I just, I don't like to be told what to do. But going back to problem solving, if you're around people that want to tell you what to do, you're not going to hear it. Yeah, right. Even if it's brilliant.
Yeah. Not, not going to hear it and not going to stay in that group very long. You know, like, who wants to? I mean, and some people, you know, I would say some people find it easier or more fitting to their personality to kind of have a list of things to do that have been, you know, already identified and then to do those jobs well and then to, you know, kind of be rewarded or not rewarded based on those things being done. Right. And that's great. And I mean, you know, but, but there's also people who like that feels confining, right? Like that feels like—
That sounds awful, actually, to me.
Well, see, to you that sounds awful. But, but I know a lot of people that would find that.
Yes.
Like, you know, it's really about did I get the gold star? Did I not?
Well, and frankly, we have to have those people.
Yeah, exactly.
We have to have those because otherwise nothing gets done.
No, because, you know, like, because the people who don't want to be confined also aren't all that consistent. No, no. That's the downside, right? And that's the, you know, that's the me and Luke dynamic in that case, right? Like, you know, I can come up with ideas and, you know, 10 of them and, you know, 2 of them are like, okay, 2 of them are like pretty good, right? But there's a 50/50 chance that 3 months from now I'm already on to the next idea. And even those 2 gold nuggets, like, I've already dropped them on the ground because I'm chasing something else.
You forgot what they were.
And then he's like, oh wait, don't you remember those 2, like, gold nuggets? Like, oh, those were like good.
Let's keep doing it.
And like, that's the consistency that keeps going.
Don't you remember when you say that? And I'm like, nope, no, I really don't.
I could, I could. Yeah. Oh yeah, I remember that conversation, kind of.
Yeah, I said that? Okay. Sounds like something I'd say. I think the group dynamic is also interesting because kind of like when I had Pish on and we were discussing counseling and therapy, he was talking about how the counselor's role, as he's being trained as a psychologist and a clinician, Yeah. Is to be detached. They're emotionally detached from the situation, right? Yeah. And that's what I found so difficult in my journey is I get caught up in the mechanics of what's what's wrong in the problem I'm trying to solve and not dealing with the emotions behind it, right? Yeah. And I think in a group dynamic, I can sit here and you're describing your problem and I don't know, I don't have any skin in the game. I don't, I'm not experiencing any of the feelings that you are around that. And there's a certain level of clarity that comes with that. But if emotion, and I, let's say I don't give you advice, I give you experience share, like I had that same situation and this is what I did, this is what I wish I had done, this is how it turned out. If you aren't in the headspace, you can't even hear the advice because you're, you're stuck in the emotion, right? Has that ever come up with you?
Yeah. And I mean, another thing, this kind of goes back to what you were asking about with, was there something that pivoted in me back in 2015 after the failure and everything? And I mean, one of the things that's really been helpful, you know, in the the forum groups is we actually have some integrators in there, right? Like people who are integrators that they're not kind of the visionary type person. Right. And it's been interesting to hear them talk about their visionary, right? Like when they're like, you know, because I know I'm the vision, you know, like they're not talking about me, but they might as well be. Right. And it's so fascinating to hear hear that kind of perspective, to deal with a visionary every day, right?
Yes.
Is its own challenge. And so that alone, I think, has helped me step back on some of the things I do and just be a little bit more aware of it.
I was a contract CFO for a client a few years ago. It was a startup in an industry that was new, and they had very rapid growth. And the visionary— I think I worked for him for about 6 months, and I left with the phrase, "Lose my fucking number." I mean, that was literally like, "Do not call me. Delete it out of your phone." I was so pissed.
Yeah.
And that guy, the founder and visionary, he was— I was never him. But I saw enough of myself in him that it gave me that perspective of what my people had to deal with when dealing with me. And I'm like, "Oh, God, that sounds awful." Because it was awful for me. And I didn't want to— that was a switch because I started thinking about how I showed up to those other people and how I could be influencing them just being me, not like intentionally, but yeah.
And that, I mean, it's taken me a while to work with that within the company too. You know, I, I'm not sure I have great examples of it, but it's kind of like, I mean, very early on in the company, I mean, very, very early on. I noticed that little things, right? Like if I cut my hair a certain way, I started seeing it around the office. If I had— trendsetter. If I had— well, as the owner, you are. And it's the little things and you don't even, you know, like people are picking up on things that you're not even saying or even verbalizing. Yes. And, and that's, you know, that kind of hit me around like I don't remember what year it was. Maybe I saw it a little bit in year 2. I saw it more like as we had more people in the office and everything. And so I just started to try to get very careful with like my actions or words or something because I didn't want, I mean, it's even little things. It's like if I'm leaving every day at 4:00 and they're seeing it, then they think that the exact, correct course of action is to leave early every day. Right now, they may or may not see me at 8:00 working that evening. Right, right. But they certainly saw me leave at 4:00. Or if I'm like, oh, it's not a big deal, then they think it's not a big deal, you know, even though it might very well be a big deal to some of our customers, some partners, etc., to other members of the organization. So I've tried to And I still catch myself doing this, right? Like, you know, in that leadership role, whether you think you are or not, there's a lot of eyeballs on you. Yes. That are looking at things that maybe you didn't even intend for them to see.
100%. And it's— I had one of my leadership team tell me one time, it's not what you say It's how you say it. And you don't understand the weight of your words. Yeah. And I think one of the things that I had to grapple with is that people have this idea of entrepreneurship that it's freedom. Well, sure, there is freedom. Yeah.
Like Braveheart. Right, right.
That freedom comes at a cost, right? If you're gonna act exactly how you want to because you're the boss, it's gonna have ramifications whether you want it to or not. Right. And so, like you said, developing that leadership of modeling behavior, modeling language, it's been a struggle for me. I mean, it's an ongoing one. Have to self-censor a lot of times.
Yeah, yeah, yeah. Agreed.
Agreed. Like that, that the— I was thinking of one instance where I was— to me, it was a funny, practical joke. And like the other team members are saying, "Oh, no, you can't do that. You'll leave her in tears." And I'm like, "Really?" And it was like, "Yeah." And I'm like, Okay, I won't. I mean, like, but to me, I— Yeah. Yeah.
Yeah, it's been a crazy ride. That's for sure.
Well, John, I appreciate you stopping by and sharing your thoughts. Yeah. Good luck. And we'll talk to you soon. Yeah.
Thanks, Christian. Yep. Talk to you soon.
