Justin Gray: What Matters to You and The Marketing Cheat Code

If you can really sit someone down and say, what is that roadmap for you? What do you really want to do? What matters to you? How do you want to evolve your family life, your personal life, your financial life, and so on and so forth, your career, and really get to the heart of that?

What are the ingredients that go into someone that becomes an entrepreneur?

When I started to hire to augment my own shortcomings is really where I started to find those people where I felt like, wow, you're integral to this business.

You were looking to break the trust barrier. And the best way I've found to break the trust barrier in order to eat the next day is through word of mouth and trust-based relationships.

So this is kind of all a crazy story, from the beginning of my career, which was the most bland, boring time in my life that you can think of. But I was trying to add some excitement. So I was working a crappy job at a company called Hughes Calihan and had just graduated school, what, like a year or so prior to that.

I had a bunch of buddies down in Tucson, and it was coming up on Halloween and I had no plans. They just happened to call, because Halloween was on a Thursday night, and say, hey, what are you up to? I'm like, nothing, I'm going to work tomorrow. And they're like, we're throwing a big party, you should come down, it's only a two-hour drive. I'm like, I'm not going to do that. Well, it sat there for a couple of minutes, and I called them back. I was like, all right, fine, I'm on my way.

I had a review the next day with my boss. It was a breakfast review, full-on, hey, promotion, career.

Yeah, exactly. So that's hungover territory. But I was like, yeah, I'll do it. And this was already like 8:30, 9 p.m. at night. So I drive down there, and I get there somewhere around 11. I saw a bunch of friends of mine. It was great. I'm like, I've got a good bed or whatever. It's like 2 a.m. at this point, and I was like, I've got to be back in Phoenix in the morning.

So I just crashed. They had this corridor. His dad's a builder, so the front of the house was all glass, and that was the entryway. And then you went right out through this sitting area into the backyard, so that was all glass too, a glass sliding door. And I just plopped down on the couch there and went to sleep.

I really don't know how much time had passed, but I woke up to his brother jumping on top of me. I orient myself, look around, and all that glass is just dropping. That's the first thing I remember, just cracked glass falling everywhere. I was like, what in the world's going on? It's like someone's shooting into the house.

It was over largely by that time. I'm sure people were running, and everyone's checking everyone out. Fortunately, no one was shot or hurt or anything like that, because they were largely all in another room. I'm the only person in that area, where I guess they decided to shoot into. We start looking around, and everyone's like, oh my gosh, it was crazy. People are running out front trying to figure out what's happening out there. And we look around and obviously the bullets had gone through the glass, but I'm on this leather couch and there's two holes over on one side, and then there's one literally two inches above my head where I was sleeping.

And so I went to kind of spring up, right, and that's when his brother jumped on top of me like, no, stay down, type of a deal. But yeah, it was an interesting evening. And I guess it turns out it's just my buddy, a guy named Carlos Talavera, had started dating some gal, and her ex-boyfriend, a drug dealer or something like that, and they were obviously not happy about the situation. So I was caught in the crossfire, quite literally.

Carlos is a good guy. I think he was in an interesting situation at that point. But yeah. Don't go to Tucson very often anymore.

It's a great town until school's out, in which case it's absolutely dead.

Yeah. So, obviously police showed up and everything like that. They're interviewing people. I think by this time it's like 4:30 or 5, and I'm like, I need to get on the road. Can I leave? And they let me go after another 30 minutes or something like that. And I drove up. I did get a raise during that review. But I did have to call in the way and be like, hey, I'm going to be like a half hour late. I've got to stop at home and shower and put a good face on, and so on.

Yeah, it's also one thing you don't really want to tell your boss, like, why am I late? So yeah, that's a good point. A lot of inferences can be made on, I just got shot at. So I don't think I divulged the reason. I think I said, oh, I had to go to Tucson and I'm still driving back, or whatever.

This was, oh God, this was my first job out of college. It was a company called Hughes Calihan, and they were an office equipment dealer, right? I guess some people still do that, but copiers, faxes, high-volume printers, things like that, networking. So definitely the most interesting thing that ever happened at that job was getting shot at in the midst of working there.

I didn't drop out. I graduated with a deficiency. I changed my major literally halfway through school. So I did my freshman, sophomore year as a journalism major, and then came to the realization there was no money in journalism, and maybe not even a career any longer in the near future. So I said, I'm going to shift over to business. I love marketing. I'm going to go that direction.

But that meant the math requirement for journalism was literally a class called Math in Modern Society. It was word problems and things like that. So now I had to take calc and algebra and so on, and I had to largely do this in summers and Christmas breaks. I was scrambling for that entire two years. It also required that I have two years rather than one of language credit. I had taken German through high school, so I had two years there. I had taken my language credit, or the one class I thought I was going to need, already, the German class, passed that. And so now I needed this other language credit, which would be German. And I was like, oh, I'll just push that off and get this hard stuff dealt with.

Well, it comes out that I'm still four credits shy when it comes time to graduate, which is no big deal. Universities do that all the time. Okay, just get that credit. I think you have two years to get that credit. And so it's literally called graduating with deficiency. I came back to Phoenix, and obviously I had to get a job and so on. And it was like, oh, I'll just register for this class via community college or something like that, which I did for literally four semesters.

I registered for it at a school locally here, in Scottsdale, called Rio Salado. I think one was at the campus, the other one was online, one was at a different campus. But every single time they would cancel this class because there was not enough interest. One of them actually came down to me going to the first class, and there's no one there. Oh no, we must have forgotten to notify you, it's canceled. So that got canceled.

So I literally still have no degree from the University of Arizona. I'm four credits shy. I probably haven't given it a second thought in the last decade. But for a while there it was like, no, I've got to get this done. Man, do I have to go back and learn a completely different language? Because you have to get it in the same discipline, right? But anyway, that's my lack of degree story.

Yeah. I think people have told me that getting into college. But when you're first signing up for college, at least for me, it was like, I've got plenty of time to figure that out. Four years is a huge amount of time, right? And I think the burden of finances brought me to that realization. My parents did supplement my school in terms of the tuition, but I had to pay for everything else, right? My car, my living, and so on and so forth.

Right. And so then you're like, maybe I can use what I'm working towards to try to earn some money, in addition to my crappy job at the Sports Authority or whatever I worked at back then. And it just very much came about like, no, you've got to write an article and then chop it around, and once you get that placement, hey, here's your big payday. I did that two times and I was like, this is not it. Then everyone's telling you, well, digital's on the rise and everything's moving to a different model, and no longer are there these big, retained employees that are looking for interesting things to write about.

And by the way, it's not as creative. Creative writing is really what I love, and it's really not in that vein. So everything just kind of started coming together. I think why it happened at that moment was that I looked at the courses my friends were taking, which were largely all business majors, and marketing was kind of an add-on into business. They were much different than what I was taking for journalism. And it was just like, man, this is really going to be a steep climb. And it was, even with two years trying to play that catch-up game. So yeah.

Yeah. I know a couple of those folks.

Yeah. But I can't take a lot of credit for that. This is an interesting topic that I think about a lot: what are the ingredients that go into someone that becomes an entrepreneur, or someone that has a high risk tolerance? I grew up around parents that, number one, just had a get-it-done mentality, a blue-collar work ethic, very hard workers. So that degree of difficulty never came into my mind. It was just like, well, I've got to change my major, better do it now, type of a deal. So it was almost like a default mode of operating.

But I do think there's a larger sociological and, you know, psychic exercise there on why people pick up those traits. Because people do the opposite as well, right? They have entrepreneur parents and they see the feast-and-famine aspect to it, which, to a T, was my upbringing. And then they're like, oh, I'm going to go into risk compliance, or whatever. And that was the only advice my parents ever gave me: get a government job, get something that's always there, that's not going to have a big upheaval. Obviously that advice didn't land. But I feel like people who were in it are always like, hey, get into this with eyes wide open, or just don't even start that conversation. But yeah, it never really was an option.

Yeah. I don't have as many employees now as I've had in the past, but to them it was always, what's the alternative? Oh, this is going to be hard, or it's impossible, or we're going to do a lot of stuff. It's like, what's the alternative? You know what I mean? Just get it done.

My parents actually lived in very close proximity to one another and never met during that time; they met out in Phoenix. My dad had taken a job as an architect, which is what he does by trade. He's a builder and designs custom homes. And my mom worked for the airlines. She was flying around on American Airlines, and she was based in Phoenix, which was a hub back then. So they met in Phoenix, but he didn't have his own business right at that point. Soon after, he was working for a firm that went out of business and then decided to hang his own shingle.

He has been doing that out in Fountain Hills, Arizona. You guys are in the Valley; it was nothing back then, right? It was dirt roads coming into Scottsdale. Nowadays it's hard to even tell them apart. But back then, that's very much kind of their spirit. They wanted to be away from the normal things. They wanted to be that pioneering aspect, I guess, and it was fewer regulations. It was a township at the time. So they moved out there very early, in 1971, and he started building custom homes. He's still doing it to some degree today.

After a while my mom actually came to work for him and managed everything: the books, front office, so on and so forth. And they did that until she went back to work, largely just because she wasn't feeling challenged in that role, I think. But that was our life. If you're not building a home, if you're not working, there's no salary there. You are killing what you eat.

Everyone's first job who had a parent that was in construction was sweeping construction sites. That was 120 degrees. Yeah, I think I was probably 10 or 11 at the time. We'd go there because my mom would clean the homes prior to the handover to the resident. She would clean them, and we would go with her and have to help out in that regard, or I'd go with my dad and sweep the job site while he was doing whatever. We were just always around it.

Then that progression was obviously, okay, now you can put the brim down and go help me install windows or doors, or frame this little area, type of deal.

Yeah, but that's not by design. That's my father's mentality. I've seen my dad jump down in the ditch and start digging along with the folks that are paid to do so. He runs backhoes, he runs dozers, whatever needs to be done. That's his famous saying, which is not unique but is true: I will never ask you to do anything that I won't do myself. I've seen that ad nauseam in both my parents, but certainly my father.

Well, I always start that conversation with the fact that we both fired each other numerous times.

But I mean, he's built a home for me, we've worked together in other businesses and so on, where we've said, screw it, I'm out. And so, you know...

Yeah, exactly. Tell me how to start that conversation. Nothing big ever happens. We are very similar in many ways, different in other ways, obviously, but both very stubborn, very hard-headed. We both have a temper. So it's always been something small. My dad's got very strong opinions about things, and obviously he's been doing that craft for a long time. You don't need this here. I think we got into an argument over electrical outlets. Why do you need an electrical outlet in the commode room, the toilet? You call that, I can think of the terms, sure. But anyway, I was like, I want one in there. I don't know what you're going to plug in, but I want an outlet in there. And that turns into a huge blow-up and so on.

It's always over some element of control. My dad's a big control guy, even when he's building a home for someone else. In fact, I would venture to say that all his customers over the years, and my dad does high-end custom, right, so you kind of have to be a little esoteric and a little off just to even go down that path, but most, if not all, of his clients have said, you know best, go do this, we'll put our faith in your hands. I did that to a certain degree, but I've got pretty strong opinions myself. So yeah.

Yeah. We were definitely middle class growing up, but sometimes I can remember my dad coming home with a boat and it was like, oh, awesome, and then our four-wheeler, that not being the case, and a lot of things getting sold. I think my parents were good about insulating us from some of that, but still, as a kid, you know what's going on. Definitely times where there were big money problems and struggles in that regard. That's as a result of the construction industry as a whole, and also the very niche product that he delivers.

And probably, when I think about it, one of the biggest impacts for me is that my dad does not sell anything. You are selling him on doing the work for you. I am the exact opposite. You take those personality tests, and I will absolutely be accused of doing more selling than telling. I think that is a direct response to, well, why aren't you willing to go out there and advertise your services more from a sales perspective? I am overly cautious and overly afraid of that being the reason why something fails. I've said before, I am a hype man. I'm a promotion machine. I'm not going to fail due to lack of demand.

So I think that is definitely a reaction to seeing those lulls and being like, no, you've got to get out there, you've got to put yourself out there. For people like my father, that is the kiss of death. You're pandering. And sales in general is, sorry to anyone watching, a low-life profession, a used car salesman type of deal, and we would not lower ourselves to do that. I just have a much different perspective on that aspect.

Yeah. I literally had this conversation yesterday. I was talking to a buddy of mine who owns what I think is one of the very first headless or fully digital agencies, meaning no FTEs. He's always done things through a diverse range of contractors, and he's assembled this Voltron team of folks that he knows does incredibly high-quality work. They do very expensive work. And typically, the more you see that artistic or craft element go up, the lower you see that desire to sell and put yourself out there.

But strangely, I think the centerpiece of both, whether you're on the sales side and you are paper thin and selling vaporware and you've got this incredibly strong sales muscle but little else, or you're on the other side, where you're offering this artisan, bespoke craft that only you can do and it's such a rarity, the middle ground for both of those, which I think both sides eventually have to come to, is highlighting the customer. Putting the customer at the end of that and telling the stories of what you are doing with those people, not for them. That is a hypercritical aspect.

This is what I used to always tell my team at LeadMD: it's not about us advertising our services. It's about advertising what that client was able to do with us, or through things that we created for them or helped them implement, and so on and so forth. How are they succeeding? How are they driving revenues? How are they retaining customers? How are they doing cool things? What are the cool things that we're highlighting? And I truly think that's the middle ground.

You're seeing that. I don't know if you guys have gone on, I had to buy a belt the other day. I'm like, where the hell do you buy a belt? I don't go to Nordstrom's or anything like that anymore. So you go online and you see that there are these highly bespoke belts. You're going to pay 400 bucks for a belt. But okay, great.

There is. There's actual quality there. It's not just a marketing gloss that someone put on it. You're going to pay a lot for it. But when you look at how they market those products, this is lower-end luxury, right? They are still putting a ton of time and effort into who crafted it, how is it made, why is it still around, oh, here's someone that's been wearing it for 50 years, and so on and so forth. You see that with spurs, with saddles, with homes, whatever it happens to be. People are trying to tell stories with that, and that's what people gravitate towards.

I think, to your point on AI, yeah, there is a ton of automation, a ton of value to be had through these cutting-edge technologies. And what it leaves is a gap and a thirst for that connection. Everyone can log on and learn how to prompt pretty quickly and automate. You guys want to set up a podcast, you email me with a date, it's on my calendar as a meeting invite, all that logistic BS is handled. Anyone can do that. But a very small group of people can go out and actually build something with their hands. And saying, I built something with my hands, is not the way to market that product. It is, hey, look at how this is done, what people are doing with it, and so on and so forth.

And again, on the more sales side, if you can't tell those stories, I don't see a place in the future for those types of vendors, because of even things like AI, where it's like, hey, go get me all the customer feedback around this solution, let me talk to people that look just like me, let me mine that information at the snap of someone's fingers. That visibility is, I think, really eliminating a layer of just crap and useless service out there.

I mean, what year do you think that was?

I was going to say 30s and 40s. So why, in 2025, are marketers still so damn bad at doing that? If you go out and look at any modern-day, cutting-edge organization's website, there's still me, me, me. I think you guys mentioned buyer personas and things like that. The distillation of those things down to these very cookie-cutter tactics has failed to transform the marketing industry. Even the way that we hire and structure teams has failed to serve what marketing really should be doing.

Because who writes content? Who assembles all this stuff? The low-level person that you can get at the lowest cost, or AI. And then we go try to put all this effort into promotion. But who should be creating it? The CEO of the company, the people talking to customers. Your own customers should be creating it. It's such a backwards thing. Which, your example just got me off on a tangent.

Yeah, you already can. My avatar just took that.

Yeah, yeah, exactly. I love that.

Yeah, couldn't agree more. I think the other big gap there on marketing is: how do you teach it? The way that traditional higher education has answered that is extremely poor. Because what do you latch onto when you try and teach something? You try to latch onto concrete, tangible elements. And so much of marketing and sales and any customer-facing position is so intangible.

I think trying to combine those elements with this rise of technology, which largely has turned marketing into this operations center, where we were at the forefront, we implemented all this crap, but along the way you could see it happening. You're losing what were at least core tenets in marketing, advertising, promotion, and so on and so forth, and exchanging those for something that is a step-by-step process, and people building careers out of it. Now when you look at a marketing ad, there's so much around, can you run X technology? People have built careers off this, right? I'm a HubSpot expert. I'm a Marketo expert, whatever it happens to be. And you've been, again, distilled down to this set of, I want to say rare skills, but they're just incredibly specialized so that no one else wants to do them, quite frankly. And at the end of the day, the results are no better than when we didn't have that technology, because we've lost those fundamental elements of how to tell stories and identify with people.

I mean, my entire life's thread is rooted in have to. Again, I'd love to be able to tell some magnificent yarn about it myself, but any business that I've started, any market that I've entered, I've always been the underdog, meaning I don't have some sort of immediate door-opener cheat. Take LeadMD. If you look at why most people start a quote-unquote agency or consultancy or any sort of professional services business like that, they're often leaving a very large organization that they can count on becoming their first client. I don't know what the actual data and the ratio is, but every single one of my competitors had that situation where their first client was, oh, it was Aon, I worked for them, it was Insight, whatever, a large company. They had developed a specialized skill set, they wanted to go out on their own and hang their shingle, and they counted on the fact that, yeah, we want to retain that great work that you were doing, so here's oftentimes a large retainer to do so.

I never had any of that. I had the idea for LeadMD after I bought Marketo as a very early client, less than 20 clients in the cohort when I adopted that solution. And the pain of adopting it, I was like, what do you mean there's two webinars that we go on and then you learn all these things that didn't exist prior to it? Nurturing, scoring. You can't tell me that's the enablement process here. I just saw, wow, that's a huge opportunity. I think this is powerful software, because it's doing things that I've wanted to do and we were trying to do through ESPs and just manual brute force in the past. So I think there's opportunity for a business. Okay, great, there's an idea. How do I earn a living with that idea?

Fortunately, it was not my first entrepreneurial go-around. I had worked at an early startup prior to that called BillingTree and really helped them start from scratch. They were at like 100K in revenue, and we took it to 250 million inside of three years. Everything that we did there was referrals and relationships: hey, if we can get in with this person, can you introduce us to someone else? So that natural storytelling just came about as, hey, that's what's driving business here.

And then parlaying that into LeadMD: okay, if I can win two great customers, charging them little to nothing, what is the value I really want to get out of them? I want to get access to the people whose ears they have, to their networks, and so on. So we did very cheap work at the beginning of LeadMD. Yeah, I'll implement that for 15K, when other people are charging six figures for the stuff. But I need you to be ultra happy. I need to deliver hyper value in this engagement, in exchange for you telling people that ask you where you're going for a solution, or at CMO roundtables or conferences and events and so on. I need this from you. That's the primary value exchange I want to get. Are you open to that? Yeah. Okay, great. Then let's perpetuate this.

That's where all of the partner stuff that we preach comes from. And we can go down a whole diatribe on why, even once people embrace partners, they do it extremely poorly. But at the end of the day, you were looking to break the trust barrier. And the best way I've found to break the trust barrier in order to eat the next day is through word of mouth and trust-based relationships. I don't care what anyone says, that's how we buy in considered purchase situations. I've rarely found anyone that goes to move to a new city, buy a new home, buy a car or some other large-ticket item where they don't at least talk to their friends, or a trusted individual in their life, and say, hey, what do you think about this?

Even though people say it's so much, this buying process happens online, the buying process doesn't happen online. The fact-finding process happens online: what do I want, what's out there, roughly how's it performed. But at the end of the day, most decisions are made on, hey, I'm thinking about doing this, what do you think about it? If your friend is like, oh, that's completely lame, okay, back to the drawing board. What would you recommend? So that's how we operate as humans.

We got dog ears and everything. I love it.

Yeah. Again, it's not that, with the rise of digital, and you guys were talking about it with Zoom and so on, we don't want to meet in person. It's that so many in-person interactions were just worthless. How many meetings have you been in where you've got 20 people in there and someone's like, this is the most expensive meeting we've had all day? But if you have a great conversation and you get things out of that interaction that you can't get anywhere else, that's what people are starving for.

The same thing goes for buying. Do I want to talk to a salesperson? Most people are going to say no out of reflex, because they've had such terrible sales conversations in the past. Do I want to talk to a sales engineer? Hell yes, because that's where they're getting their value from. That was our entire methodology at LeadMD. Our salespeople weren't salespeople; we called them solution consultants, right? I want people that can actually give value in those interactions, not just, oh, let me show you a product, or here's our pricing structure. That's stuff you should be able to get online. What you can't get online is what people are looking for in those interactions. And oftentimes it's stories.

Yeah, I don't think there was ever a moment where I said it was great for a little while. That was what I had to do. Being the son of a GC and a contractor, I never enjoyed that crap. I never wanted to be doing it. It wasn't a labor of love. It was just a labor.

I think fundamentally, and now we're getting into deep psychological aspects here, I have an incredibly bifurcated mind. In one aspect, I crave stability, in terms of, no one can pull the rug out from underneath me. Because of that rug pull that I saw when I was growing up, I have a huge affinity to creating situations where that supposedly can't happen. I want to believe I'm in control, right? Never heard that before from an entrepreneur. And at the same time, I have an extreme risk tolerance. I don't know how those two items coexist within one individual, but they do.

I always say that I've been fired from every job I've had, and I think it's actually true. I don't think I'm forgetting anything. Well, I did leave one job, but I think I would have gotten fired there eventually as well. Never for underperformance, always for overperformance, but for not knowing my lane.

My first go-around, we can go into that backstory if you guys want, I graduated with a degree in marketing, I applied to a bunch of marketing jobs and I got one. It was terrible. You're definitely in a box, you're doing this one thing, and no one respects marketing. I don't think I really fully understood that until I started operating in those roles, and granted, I started out on the low end of the totem pole, right? But I didn't see that change as I went. I think the highest I got was a marketing director, what I would call someone's employee. I hated those jobs. I hated being in a box. I hated feeling like what I was doing every day wasn't making a difference. It didn't matter. Whether you have that sales slick or not, is that really going to move the needle? And that's literally what I was doing. I was building websites, designing, writing copy, building digital assets, and so on.

And then I got the opportunity to jump into a startup. And this is, again, risk tolerance. I made that leap, and I found what I'd been looking for, which was a no-barrier, no-bureaucracy, no-red-tape situation. They're called startups because no one cares if you want to go out and suddenly answer a customer service phone call. They are happy that you're willing to do that, right? No one cares if you see something going on in sales and you want to redesign that process, redesign the messaging, pitch it, test the messaging out with customers. No one cares. They want to make sales. That was my aha moment. That's my manna from heaven, where I'm like, oh my God, you mean I can do whatever I want as long as I do it well? Yes. And that seems like such a stupid unlock for companies, where it's like, oh, you can't do anything but what we've hired you to do. But it happens obviously every single day.

With that lack of structure in startups, I was able to say, yeah, I can do all of these other things, which I had been doing to a certain degree in past jobs. I had a job right before that for a software company called Computer Guidance. When I got the job, I was one of five on the marketing team. I slowly worked all my colleagues out of a job. They would get fired because they weren't performing at the level I was performing, and I would get saddled. So I'm literally doing six people's jobs at the end of this road. That was my way of doing, hey, what's within my arm's reach that I can pick up? But it didn't necessarily lead to success. I was just doing six people's jobs for the salary of one, right? I wanted to break out of that structure.

When I took the job with what was then EPP, which became BillingTree, hired as their marketing director originally, then moved up to VP of marketing within six months, took over sales within a year, I had my own little fiefdom. I could do whatever I wanted. Now I started creeping into areas like customer success and support and so on, and that's where all of that friction came from. We mutually decided to part ways at that point, but that's just a nice word for being fired, right? Because I saw things being done that were not the best that they could be, and I wanted to go over there and fix it. So when I say fired from every position and so on, that's the undertone of it. And finding not just startups but entrepreneurship, that feeds my frenzy in that area to a very satisfying degree.

Yeah, I mean, how else are you going to weather the intense ups and downs of starting and owning a business, right? You have to believe in that. And so let's go back and try to apply that to how this often is not the thing everyone expects it to be.

No, seriously, now I've lost my train of thought, man. What did you ask?

Yeah, so let's look at that again through LeadMD. We are a go-to-market consultancy, right? Am I just so pissed off that other people aren't doing go-to-market well that I have to do this? In the beginning, I was like, oh, there's something that no one's doing, and I feel like it needs to be done, and I want to do it. But shortly thereafter, that stopped being my mission in that business completely. What it became was providing upward mobility to employees, because I knew I wanted that as an employee. I wanted to say, hey, if I work my fingers to the bone and go all in on this, reward me with ownership in this organization, reward me with the ability to see the fruits of my own labor.

And it started the business, early employees, very easy to see an employee that's going to work out versus an employee that's not going to work out. And then you've got a different class of employee, which is, wow, they are amazing me, which is hard to do. Great, I want to reward you in that. I see where you're at in life, and I see echoes of where I was in that same position not too long ago, and I know how good it feels now not to wake up at 3 a.m. in a panic attack on not being able to pay a bill, or have crushing debt on top of you. I know what that feels like, and I don't want you to feel like that. I'm not going to just give something to you, though. Here's the exchange for that: I see what you're [inaudible] to be rewarded.

That became my absolute must mission in life, in seeing the types of individuals that were willing to provide that commitment and that work ethic, quite frankly. I recognized it. I've seen it before. I've seen it in my family. I've seen it in myself. And I think there are too few organizations that truly reward that in a way that is commensurate with what that takes to perform.

So, to your point, it wasn't necessarily the product offering of the business, but it was, wow, this is a people-based business. My product walks out the door on two feet every single day, and they can choose to come back or not. Every single one of them can go earn more working for one of my customers than they can working for me. And by the way, when you do really great work at a consultancy or an agency, what do we do? We give you a lot more work. That is going to be the equation here. If you are a great employee, congrats, you just got your own department and now you own a P&L. Not a lot of people willing to sign up for that. So I think that's amazing, and I think the only way to reward that is with the seeds that can ultimately grow into upward mobility and financial security.

Yeah, because I was amazed. When I took the leap and joined that company, with my classically conditioned brain at that time, I probably would have just been happy for a salary and a good bonus program. But what they structured for me enabled everything that I've been able to do in life. And even though we stopped getting along in very big ways, I respect the hell out of that. My first bonus check was more than I earned in a year working at my previous job. That's a big life changer right there, right? Okay, debt's gone. All right, now I'm actually saving, and I'm a fully functioning member of society now. Had that not happened, there is a totally different path.

That was a LeadMD thing. So yeah, my wife got hired for one of our clients, and she was a director. She was in charge of running the relationship between LeadMD and that company. I didn't interface with her on a daily basis, but we threw a big customer appreciation party in San Francisco. I think that's another key element. I'm going to go a little bit of an aside, but when people start businesses, I think you can always tell what their aspirations are based on how they think about their market. I sure know so many people that own agencies and consultancies. Again, I'll speak from a professional services standpoint, just because it ate so much of my life. What's our client roster? It's Arizona.

I think I had two clients in Arizona across almost 4,000 over an 11-year period, because we never wanted to be an Arizona company. I wanted to be in that group over there. So every tech center, certainly the Bay Area, Pacific Northwest, the Austin area, Texas, East Coast, Boston, New York, and then you've got some things going on in the Midwest as well. Those were our client bases. When we threw parties, we didn't throw them in Arizona, we threw them in San Francisco. Had we not had that mentality, I would not probably have met my wife. She walked in the door and said some very snide comment about, you can't be the CEO, because apparently at that point I still looked young. That was the beginning of our relationship. But yeah, she was a client. So I still joke to this day that she is my largest bad debt expense.

We have two kids. Yeah, that's kind of our main job. We work together every day. We did some projects together, because throughout my career at LeadMD, I stopped delivering, being responsible for delivering client work, probably around year five. But I would get called in for crazy stuff, really off-the-wall stuff, hard stuff, or just, hey, we've got to go talk to a very imposing board of directors at a Fortune 5 company. Obviously, I'm going to be there. So I sprinkle in ad hoc like that, and I enjoy that ADD-type approach to anything.

So yes, we did work on, I think, two or three projects. Then she left that company and actually got hired at an Arizona company, and that was one of our few Arizona clients. She brought us on there as well, and we did work together on that project as well. So yes, we have worked together over the years.

I don't think it would be a good idea for us to work together every single day, just because you need some variability in the dynamics of the relationships that you're dealing with. But a long time ago, I learned that the entire key to teams, to hiring, to employee relationships is hiring to augment. My first go-around at LeadMD in hiring was, I just need to find more of me. I think every entrepreneur says that at some point: copy myself. If I could just hire another 10 of me, it would be great. No, it wouldn't, right? Because the same gaps would be in the business all the way across. I am very bad at a lot of things. When I started to hire to augment my own shortcomings is really where I started to find those people where I felt like, wow, you're integral to this business. If I had just gone out and hired myself, I'd probably fire myself.

My point there was that Jen and I are extremely different. Jen is a rule follower, right? She wants to know what the process is and not deviate from that process, or someone could get in trouble. I don't know who the trouble police are, but she has in her mind that there is one. And I'm, did I read the instructions? No, I didn't read the life instructions. I'll figure it out. And if something blows up, hey, we'll deal with it at that point. The reward was too great not to take the risk. So we are very good complements in that regard.

I'd never buy a piece of Ikea furniture. I'm a big advocate for buying things once, even though in a lot of cases that's impossible. I hate buying something twice. It really gets my goat. But yeah, I would not read the instructions if I had bought that piece of furniture.

Oh God. Great day. Oh man. Yeah, so this is the first life of Justin, right? I'm working normal jobs. Hughes Calihan, they've been sold now, so I can talk openly about it. What a boring job. You're in a company that is, by every definition, sales first. You've got salespeople that literally are going, technically, door-to-door to businesses and either trying to win new business or upgrade.

Exactly. And so marketing was an afterthought. I think they knew they needed it, because they had billboards and radio spots and things like that, and someone had to manage this crap. So they termed that marketing. It was a miserable existence. I hated my job.

I was dating a gal at the time, and the absolute worst time to ever have a child would have been that. I was in no way self-sufficient. I was living on credit cards just to subsist, because I think my starting salary there was $23,000. And this was not that long ago. This was 2002 to 2004, so it wasn't like 1914, right? But not a lot of money. I think everyone I knew was making more money than I was, and I hated what I was doing for a job. I wasn't really happy in my life. Great gal, but she hits me with the news one day. I think it was us pulling into work, actually. It was, oh, great way, eight o'clock in the morning. Oh. Yeah, guess what, we're pregnant.

I'd say there's always a gradient of who's more into the relationship, and I think that was definitely in her court. And I was like, holy shit, right? But whether it's right or wrong, and I'm not going to get into those nuances, we decided to keep it. But she ended up miscarrying, like month four or five, which, I don't want to say this and be heartless, but my God, that's the biggest relief I've ever felt in a day in my life. Things could have gone in a very different direction, I'm sure a fine direction, right? But I was not in the place to be a father at that point. The relationship stuck around for like six months after that. I still know her and we are friendly today and so on, but it would have been a much, much different life.

For that four or five months, I remodeled a condo for us to live in and this, that and the other. We were going on that path.

So, like I said, I'm not going to make a judgment there. But yeah, I felt like I had to do the right thing.

There's a lot of, you're young, come what may, type of an attitude and so on. All the stereotypes are true. The decisions that you make early on will impact you for the rest of your life, and it's not something that people just say. It happens every single day. That was a wake-up call, I would say. There are consequences. I think it was also a kind of call to action in terms of, what am I doing with my life at that time? If something were to come along, because I always felt like, oh, this will be my first job, and then there'll be a natural progression. That was not coming.

So I did leave that job not too long after that. Actually, I think it directly coincided with the miscarriage, when I was leaving that. Yeah, absolutely it was. I got a better job, right? It was more fulfilling from a work perspective. But I think that sparked, hey, it's time to get your shit together. Yeah, you're 24 at this point, but that's kind of far along as well. I'm a total believer that it's never too late to do something. But man, the earlier you get started with something... I remember something that always stuck in my mind. People would say, if you just start saving $100 today, this is what you can realize down the road. And I was like, man, not only do I not have $100 today, but that seems like a different life to even consider. And I was like, why is that? That shouldn't be the case. You've got to make some changes and get things at least moving in the right direction.

Yeah. I think I was very much in the mentality of, let's just go have as much fun as possible, right? That was my weekends, that was my weeknights. At that first job, it was not uncommon for us to go out four or five days a week drinking after work. And that's not tenable for a lot of reasons. It wasn't tenable financially, it wasn't tenable from a health perspective, and it certainly wasn't leading to the best decisions.

I'm extremely blessed in my life, but man, I don't think about it a ton. Every once in a while I'll be like, man, this is the whole multiverse. You could be living a very, very different life. I didn't get married until I was, shit, what was that? 39. So that's another 12 years to actually getting married, and then another three years past that to having kids. I say all the time, no one would marry me when I was 21 years old, and it's true. I just didn't have the maturity, financially, emotionally, and so on and so forth. Taking that time and having that time to develop, not only from a safety and security standpoint but from a mentality and emotional standpoint, just everything that goes into being a human. I think about raising my kids now, raising them when I was 25, good God, that's terrifying.

Yeah, I think it'll be interesting once my kids get to that age, right? Those will be interesting conversations.

I remember my dad said to me, okay, you finally got out and done something I didn't do. I can't help you with this one.

When I told them that my girlfriend was pregnant. It's like, you finally got out and done something that I don't have any experience with.

Not well. Not well.

No, I think it was more from the vein of, wow, this is a monster fuck up. How are you going to deal with this?

Oh, yeah. Yeah, no, I was getting no help from that angle.

I think it'll be very interesting. You can sit there and say, oh, no, I'm going to let my kid fall down a ton of times and learn from their experiences and so on. But I was talking to a friend of mine because they're thinking about having kids, and I was like, well, be prepared to have the degree at which you love something scare the shit out of you. So I think that's why it will be interesting. I know what I want to do. What I will do, I think, is something that can only be decided in the moment.

Five and seven. I've got some time to work on it.

Oh yeah, in fact I already make him sweep the garage with me.

Did you spin it into an office cleaning business?

Well, it's funny, because right now I'm looking for main street businesses because I want to have something more tangible. Because you always ask me, my daughter is a little bit young to ask this, [inaudible] and stuff like that. But you'd be like, Dad, what can I help you with? What are you working on? It's like, I'm analyzing an investment right now and I've got to talk to people on the phone all day long. It just doesn't have that same gravity for kids. So I would love for something to work out in that regard, to find something that they can actually operate in on a daily basis, and make sure that job sucks too, because I think that's a great learning experience. I don't know, analyzing investment for a kid kind of sucks, so it sounds like a great idea.

I mean, for some reason my son is very money-centric, so he'll probably enjoy it. My daughter will give him money, she gets it in the Valentine's Day card or whatever, and she, oh, you're a Grayson. Like, he will never give up any. He's got a bank inside of a bank that has a combination on it. Oh, it's awesome, man. I honestly cannot say this came about as something that we've taught him. We're like, where is he getting this from? Very protective over his funds. And he's dealing with crypto. He could tell you immediately what he's got in dollars and change in his bank right now.

I think that's been a process that has kind of snowballed over the years, quite frankly, trying to learn how to manage people and align people and rally people. I've never found it successful to just tell people things, like a list of instructions. If you can get them understanding and believing, it's kind of like when you go buy a house and the family's like, oh, the couch would go well over here. If they can picture themselves in that moment and what it's going to mean for them, I think that's the only thing that I found sustains. Other things kind of diminish, other financial rewards and accolades and so on, they just kind of fade away. But when people believe something like that, they're going to do it.

I've never found a better way to identify with that than, I guess it's actually two things. One is being open and vulnerable, right? Hey, this is why I'm doing this, this is what I've seen, I want better or I want the same for you, whatever it happens to be. And the other one is, have you identified what they really care about? I think that's something that very few employers take the time to actually learn. We just make assumptions and so on. What is that roadmap for you? What do you really want to do? What matters to you? How do you want to evolve your family life, your personal life, your financial life, and so on, your career, and really get to the heart of that? You've earned the trust to have that interaction. That I've found to be the other motivator as well.

I think, for me, that is all rooted in finding people worth that investment, because I think that's hyper important to that equation. If you don't have great people, that is never going to manifest. It's never going to come to fruition. And now I've got kids on top of that, which is, yeah, all right, how are we not only going to create that mobility, but how are we going to create this generationally moving forward? So frankly, that's what I spend most of my time thinking about.

Yeah, I do think it has to start with, what are you looking for? We spent a ton of time on that. One of my buddies from college actually became a PhD, a Northwestern PhD research psychologist. He's got his doctorate, he's got a ton of accolades. We brought him on as our head of data science. And in his spare time, literally not outside of work hours, he and I would work on these little problems. Hey, this team is working really well over here. Why? Let's analyze. Let's give them traditional personality tests. And then we came up with one to augment our own and so on. Why does that work really well? What are the traits that we're actually hiring for? What are the components of a successful team?

We talked about this just a bit ago: you've got to find the puzzle pieces that fit together. If you've got the same piece, it's just not going to work out. So we spend a lot of time trying to understand that first and foremost. But then, how you actually identify that within people. Quite frankly, the amount of time that we normally spend in a hiring process is woefully abysmal. Right? What are you dealing with? Some Zoom meetings and then maybe an in-person if you fly someone out? Or maybe if they're local?

Yeah, dude, what are you doing? There is no way you know this person at this point, just because they said the right things or you're looking to check a box. I do think hiring is the number one superpower of any great leader across the board, not just the CEO but all the way down the chain. If you can identify great people, the commonality that I find amongst all of them is that they are spending a lot of quality time with those individuals. And they are rarely talking about the job to be done. They're always talking about their personal lives and what they want to do. What do you love about this? Tell me about the best bosses you've had and why, and the worst, and so on. Getting outside of that concentric circle of, this is what the job requires from a day-to-day basis, and this person as a human. For me, that is going to tell you so much more than any of the BS ways that companies hire today.

Yeah, way too many people, right? Just an anecdote in that vein: we hired over 380 people at LeadMD to get the 64 that I sold the company with. And not all of those were firings. Some of them were Tour of Duty, which is another great concept that was brought in by a guy named JT Bricker.

Tour of Duty. The recognition that, yeah, you're probably not going to retire here, but what do you want to accomplish within this two- to three-year block? And at the end of that, if you want to re-up, awesome, if we both feel good about that time, we both got value to give to one another, let's go through another tour together. But the expectation that you work at the post office for 60 years and then you retire is just not feasible these days, and certainly not within fast-moving B2B SaaS. So I think that concept is absolutely critical. And just constantly re-upping and renegotiating that relationship, I think, is key.

But 380-some-odd people to ultimately house between 60 and 65, that we typically did, just goes to show there's a lot, even with good hiring in place, that you're never going to know about someone within that period.

Definitely discover them? They've been out there.

What I love about it is it literally works every time. I have yet to see that methodology not work. I'm not saying every single interaction. I'm saying when someone embraces that mentality, I have yet to find that that is not one of the most, or even the absolute most, performing channel for them. And the reason is, again, every business I've started, largely other than in revenue now, because I'm later in my career, I did not have a name within that space. So how do you gain access to the people that you want to look at your product and hopefully buy your product, right? You've got to get access through someone who holds those trusted relationships. And there are tons of those people out there.

So I'll pivot quickly to what I hate about it, what this has become. Normally, the first conversation with a founder will be, hey, what's your partner ecosystem strategy look like? Oh, we just got on board as an AWS partner or a Google partner or an Adobe partner. Okay, so you get a logo on your website. What are you doing with that? And largely, normally, the answer is nothing, right? Oh, they just want referrals from us and they don't want to give us anything in return. I guarantee that's not true. At some layer in that organization, there's someone that you can provide value to. And then the question is always, no, but I want things from them. You're going to have to give them value first. You're going to have to find someone in that org that, again, has access to the people that you want to gain that access to, and find out what they're struggling with and solve that problem. That will then earn you the goodwill. Oh yeah, these guys do great work, let me bring you in to that relevant conversation, to that customer account, whatever it happens to be.

But you have to find great partners that are aligned, that at least certainly have access to your ideal customer. They serve the same companies that you do, and they're at least peripheral to the problem that you solve. If I'm offering a marketing solution, it doesn't do me a lot of good to interface with partners that are all on the finance side. It's a bridge too far. And you see that all the time as well: oh, I see you're connected with so-and-so, can you make an intro to them? It's like, yeah, but you're selling a totally different solution than I do. They have no purview over that. They don't care. You've got to make sure all that alignment's in place.

But then if you really go beneath the surface and say, okay, where can I add value to this organization? For us, it was first in sales. Why weren't people buying marketing automation? They weren't buying it because they didn't have the staff to do so. We can solve that for you. We can take that objection off the plate, because guess what? We run marketing automation for people. Or they couldn't speak CMO. The CMO or the CRO was the purse holder of the budget. They're a 25-year-old kid hustling out of Marketo's office over in San Mateo. Why am I going to tell you my strategic goals for the business? You're talking features and functions and I'm talking brand expansion and demand gen returns and so on. Someone needs to speak to us. Guess what? We can do that. We can come in there and do that for you. We will be your solution consultants: your ROI models, we'll create your decks, we will help you pitch this to boards. Those are holding deals up for you, so let us augment that for you. And by the way, we're willing to do that for anyone you bring to us, even if they haven't won, they don't want professional services or whatever. I will be your augmentation layer. And eventually that will snowball back in the other direction.

Same thing happened on the customer success side. Oh, there's one of you for every 150 customer accounts, and you're being asked to find green across the board, and you've got a very simplistic framework that your boss gave you that doesn't understand marketers whatsoever. Oh, we will do health checks on all of your yellow customers for you, free of charge. I just want the business that comes out of that. No problem, right? I'm delivering value first, and I'm not even necessarily asking for a return, but I know it's going to come, because I'm serving the same people, the same organizations, solving the same types of problems, and I'm filling gaps that your solution doesn't.

All right. I mean, we work from their offices.

The passion, yeah. I think there's also a big element there where I am just a natural marketer, in that I believe in top of mind, probably above all other things. So yeah, I want to provide you value, to have a solution that has outsized returns associated with it, but I also know you're going to forget about that tomorrow because it's not something that's right in front of you.

The thing that sparked it for me was I would see how employees learn so much from osmosis, from being around one another, and they constantly say, if I didn't hear these phone calls happening, it would have taken me years to come up to speed on delivering these services. It's like, right. Well, every time I go and talk to someone, it's like, oh yeah, this account needs to talk to you guys. So how do I take those moments and extend them out? Hey, would you guys mind? They had a bunch of empty offices. Would you guys mind if we came over here two weeks a month? I hired all of my go-to-market staff, all my salespeople, from the Bay Area, and a lot of them were former Marketo AEs. So, hey, how do I get entrenched in that ecosystem and show them there's no barrier here? When something comes up that's opportunistic for us, we're right there. Why wouldn't you pivot that chair?

You have to deliver great service. And I think that's what we did, to the pinnacle, because we had great people. When we sold, we had an NPS of 82. A true NPS in a services business of 82, all nines and tens. And that is table stakes. A lot of people say, oh, I'm delivering great service and clients should come to me. I've never found that to be true. You've got to get out there and, again, tell those stories.

Everywhere my customer looks, and my first-run customer was my partners' AEs, how do I get in their newsletter? How do I get sending them videos? How do I get in their office? How do I sponsor trips? We took them to Lollapalooza. We took them to Napa. We took them to Tahoe skiing. We took them to the Waste Management Open out here. Every year we did a reward trip, and we wouldn't just invite the people that had done great referrals for us. We invited the people that we wanted to be doing great referrals, right? Hey, bring one friend with each of you, because we'd never have a limited budget. Bring another good rep out with you, and we'll show you guys a good time, put you up in a five-star hotel, and [inaudible].

And those stories, still, I'll run into someone. I was on someone's podcast the other day, and he's like, you work there in the marketing department. Man, those bonsai trees you guys did for us. I'm thinking, what don't people throw away? They don't throw away trees. So let's get them bonsai trees, print the logo on the bottom of it with the email address to email.

And speaking of obvious, right? I've got one of my portfolio companies, and they've had kind of a slow burn to them. And then finally that pendulum is swinging the other way. It's solely because we put someone in there who I used to employ and manage, so I know he's great, who has that mentality. And at the same time, he hired someone from the CEO's network, basically doing the same job. They're not geo-based around [inaudible], right? Young company. They both have the exact same opportunities. Who is blowing the doors off?

It took a while. And it took a lot of, oh, so-and-so just sent out 10,000 emails last week, what did you do? They're making X number of calls per week, what are you doing? And a lot of frustration from the individual in there, a lot of talks on our weeklies and at night and over Slack: hey, you just need to have faith that this will work. And now the windfall is happening at this point. So yeah, it does require investment and trust and a very aligned organization to make it happen, but I've never seen it not work.

Marketing is normally totally disconnected from the customer. That's insanity. We eventually built a pretty sizable marketing department for ourselves, and their goal was, hey, you need to get out there. A customer engagement every time someone's pitching, you're in there. You just can't do that without that proximity, and certainly from a management perspective.

Immersive, yeah. Is it just a fancy term for paying to work?

Well, not only that, we're incorporating ourselves into an industry that, so what do we know about venture capital? We know that it is a results-based business. So who are great VC firms? Those that are generating great returns for their LP base, right? So starting a new venture capital firm when you've not been a part of a previous VC firm as an operating partner or a GP of themselves, any of that cachet, you can't say, look at my track record. But I love venture because of what it stands for. I love it because it's early. I love early-stage venture because of that one-to-ten journey, which is absolutely my pinnacle favorite. But how do I get into this space? How do I provide a unique value that no one else is providing? Same thing, other than—

Yeah, I mean, you can get money anywhere, right? And if you can't, then you probably don't want to invest in that company. The question is, how do I break into this space where I have no inherent cheat? Again, you don't know me, you don't know our brand, you don't know our track record in this industry. And speaking of speaking to customers, that's all I did for six months prior to leaving, because I sold LeadMD. I didn't have a [inaudible], stupid enough to stick around and try to make sure the customers and the employees didn't head for the hills.

About 18 months of that, I was like, this is my nightmare. I don't work for people. That doesn't work out for me. So I told them, hey, I'll sit on the board, but I've got to go out and do the next thing, which I had formulated was going to be venture capital. During that last six months there, I went out and got in front of every single VC that I could, every single founder that I could, every single operating team that I could. How do you work? What do you do? What do you find? What do you struggle with? What do you wish your VC did? Because every VC says they have a value add. Never did those founders bring up the value add. Never.

Hiring is normally what they were seeing value in. They were doing some good referrals. Fundraising, that's probably actually the pinnacle. You take money from someone, [inaudible] relationships, they're going to do the next funding round and so on. Aligning with the right investors. Never heard anything in terms of the value as they advertise so heavily, like, oh, we're going to advise you, we're going to help you navigate challenges, whether it be product or go-to-market or finance, whatever it happens to be.

That was great, because I love go-to-market operations. I loved building this business and doing the little things like spinning up a CRM and creating what was going to be our go-to-market process. How do we denote those partners, and how do we capture the conversations we have with them? I love that building from scratch. So I'd love to do that from within companies, and I think we're pretty good at it. So what if we package this up and actually provide a value add that was highly tangible, because we're going to work alongside you in your business? We're not going to wait for even a monthly meeting or a board meeting, God forbid. We're going to talk weekly. We're going to try to invest at least 20 hours of our time on a weekly basis operating within your business. And we've got companies that we do more than that in. Yeah, we'll bring money, but again, you probably have that covered if you're a business that we want to invest in. So that was the value-add component that we wanted to couple with capital.

And then the question is, well, how do we get access to great deals? How do we get deal flow? Again, I don't want to go out and blanket the market looking for the next best thing that no one else has found, when they've got 50, 100, 150-person analyst teams, modern companies way early in spaces and markets, way earlier than I do. But I wonder if they'd be interested in opening up some allocation for us so that we can provide this value add. How do we advertise to them that it works? You're holding it in your hand. And then, of course, our best referral agents are our founders. What are we doing for you? Will you hop on the phone with that new VC that I want to partner with? Just tell them how the experience has gone. Tell them what our revenue was at that time and what it looks like today. We're on average 3X-plus companies year over year. That's not normal.

So being able to find those gaps within the market, design it around something that we can provide, and then finding, again, a route to market through a trusted partner channel is just the same playbook that we do over and over again, and frankly do within those companies once we invest. Again, it just works, right? And I get to do what I love to do every single day.

Yeah, their biggest red tape is that most VCs are at a point in their career where we don't want to go down and do those things, right? The stuff we do on a daily basis, obviously, ranges from the highest-level strategy, do we dump this product, do we dump this market, what's our pricing strategy, so on and so forth, down into, hey, I'm going to help you stand up that very small operational process, take advantage of an event that you're going to, or help you with CRM or go-to-market tools. I love that gamut. And so what really is the connection is, we're jumping down into the trench. I've never forgotten that aspect: if you can do those skills, just because you get to this level doesn't mean you shouldn't do them anymore.

The most challenging moment? I mean, we've been through a couple of them already. So I'll try to come up with a new one here.

I'll go through an interesting one. So here's maybe the downside of being so forward with partnerships and relationships. I mentioned that I got an opportunity to work at a startup, a company called BillingTree that's still around today, and kind of increased my profile there quite a bit, right? Took on a lot of responsibility, grew the company like crazy. We got to a friction point where I said, hey, we're going to go our separate ways. And after I did that, one of the partners of the organization came to me and said, I want to be involved in whatever you do next. Whatever you're doing, I want to be a part of it. I think it's going to go to the moon. We're going to do what we did here again, right? Because pretty much zero to 250 million is a really fun ride.

Not to get totally in an aside, but I was telling someone the other day, they said, what was the moment that you knew the business was successful? It's like, well, when I stopped counting the GoToMeeting licenses and started ordering the entire menu at restaurants, that was a pretty good indicator. So that's what I did. I think I was in a lot of ways hungry to keep that going. Very nostalgic for, yeah, we did this together, let's do it together again. We violated every rule that I have for hiring or partner alignment. Didn't talk about what the exit strategy was, what we expected for the business, what the business looks like, how's it going to make money, none of this stuff. Didn't talk about it. We just said, yeah, we were really good buds, let's go out and do this thing together. We weren't even aligned on what each person was going to do, right?

Probably downloaded, here's another nugget of terrible wisdom, downloaded an operating agreement off of LegalZoom, formed a company. And before you know it, we had a business that was owned 50-50 by two partners that were not aligned whatsoever. We started growing the business, and it became very apparent he viewed his role to be that of an investor, and I was the operator, although I didn't need investment when I started the organization because I did sell my equity. He said, oh, let me put something in. I said, well, I'm putting in a hundred to start the business, you put in a hundred. That's what we started the business on, and we started growing the business, which, you guys have experience in the professional services world, what does growing a business mean in that space? It means hiring people. When you get successful, you get more contracts, you hire more people. That's what we did. I didn't take a salary for the first three years of the business. Everything went back into it. It was all about how do we do more of what we're [inaudible].

Well, as an investor, it turns out that wasn't what his ideal situation was. That wasn't his utopia, which we both looked at each other and said, how did you not know that? So it got contentious very quickly. No, I'm not going to pay a dividend this quarter, everything is going into the business. Now, remember, we've got a 50-50 operating agreement. Ultimately, he fired the first shot. He sued me for breach of fiduciary duty because he had no visibility into what was going on, but tried to say every expense that I was spending was frivolous, essentially. Because I would go to San Francisco and we'd put on events and so on. That's money that should have come back into his pocket. Keep in mind, we came from the payments world. Payments is almost pure profit. It runs as soon as you start processing for someone. Services in marketing definitely does not. So just two vastly different worlds.

He sued me. I sued him. And by now the business is turning two, and we've got lawsuits going on. The option for me is, well, do you want to fight this? You could easily fold the business, nothing's owed, right? You both just take the assets, split them 50-50. And I said, I think that's going to be detrimental for the organization. I don't think I'm going to be able to fire my employees and rehire them, recontract all my customers, go through that optic, if you will. I don't know if that was the best decision or not. I probably could have done that. At the time it seemed like this is just the kiss of death. We've got momentum, I want to keep this going.

Funny thing is, through lawyers, we had to retain a forensic accountant to come in and figure out where all the bodies are buried. Lo and behold, there were no bodies buried. But what they did, so hard to prove I'm not embezzling or misappropriating funds, I don't realize I'm giving them all of the ammunition that they need to price the business. Funny enough, the forensic accountant, who's a great guy, is one of my investors now, so good things have come out of it. We got all the stuff together, and they said, hey, we didn't find anything, but by your projections that you handed over to us, this is going to be a six million-dollar year. And I'm like, but yeah, I'm a solopreneur, or a solo C-suite at this point. I'm the CFO, I'm the CEO, COO, right? If I don't hit that projection, who cares? That's my pie-in-the-sky goal. But now it's in the record as, no, that's what we're going to do.

So it would have been 12 months in the future, and here's what you did this last year. I think we had gone from zero to a million to 1.8 was the first two years of growth, right? That's pretty aggressive growth, and it's like, okay, well, we can see it's more than doubling the business, which is basically what you're doing, but we can see a straight line to doing so. We think a 2x multiple on that is fair. And that was the high negotiating point. Ultimately, I ended up with a $3.5 million price tag for the business and had to pay him $3.5 million for my own business to go away, essentially. He had never put in a day's work in the organization. He put in a hundred grand. I think it might be the best-performing investment that I've ever been, other than crypto. And just, yeah, not a good day.

It was actually not a good six-month period, because everyone would see me coming to the office wearing a suit and tie, knew I was going to lawyers, depositions, so on and so forth. Just a real drag. And then you're trying to grow and run a business at the same time, right? And guess what? The pot of gold at the end of the rainbow is someone else's, because I'm not getting any money. Keep in mind, I'm not taking a salary. I'm literally getting nothing out of this business from a financial standpoint at that point. But now I'm paying, rewarding someone for misalignment.

But that is a lesson learned, and certainly the largest lesson that I've ever learned, which is, number one, don't bring on a partner unless you absolutely, absolutely need it. If you do, there's got to be a massive amount of alignment there. You have to know what you're getting into and what it's going to look like and what happens if things go wrong, things go right, so on and so forth. But those were painful checks to cut. I think it was like a 14-month payment plan. I had essentially, because I didn't have that money just sitting around. That's what we worked towards. Hey, that's what we're indentured basically, and we've got to grow above that. And frankly, that fed a lot of our growth in those years. We got up to around seven and a half, eight pretty quickly after that. And then 10 was kind of a ceiling, and then we broke through and went to almost 20 before it sold. But yeah, just a big learning experience all around. It wasn't just one bad day. It was a lot of bad days.

And the other thing is, it's just so easy to be like, ah, legal, that's a big expense, I don't want to incur that. I've done so many things trying to save legal fees that have come back to bite me in the ass at the end of the day. That is a big one. Never start a business through some sort of online service. And obviously find good representation and so on. But it really makes a difference to dot your i's and cross your t's with a good attorney.

Yeah. We've got referrals out there. We've got partners that will lead us in that direction.

Yeah, and then it got wrapped in with the drug bills.

Yeah. My father's been in the home building industry, and when 2008 happened, he basically said, I don't want to weather the storm, I'm going to do something different. My parents had gotten that piece of land from my grandfather, or got a different piece of land from my grandfather, bought, traded it for this along with some cash. It was supposed to be their dream home, right? In rural Missouri. And in the early 2000s, actually before I got my first job, 9/11 had happened, no one was hiring. I took about four or five months and went back and helped them build that dream home on that plot. He'd been saving up logs from Montana and wood floors and fixtures, from 30-plus years of building, with the idea that it was always going to go into this house.

They had built that home in the early 2000s, and we have farmland around it. We've got about 130 acres of tilled land. And we're like, hey, we can do something more with this than just leasing this out to my uncles and cousins and things like that to traditionally farm it. So we decided to convert it to organic. That gets a lot of harebrained ideas. I've mentioned the Main Street business; we're looking at potentially building an RV storage location, which would be the business that my kids could work in, or at least get some good old-fashioned manual labor. But this was another one of his ideas: hey, organic is going to be big. I want to convert the farm to organic. So that's what we did. And then we started Grayson Organics as a part of that initiative.

Since 2008, well, it takes three years to certify organic, but we went through that whole process, because you can't have any pesticide for three years, and got that certified. We put in a high tunnel, which is like a big greenhouse, where you grow leafy greens and tomatoes and small-batch produce, and in the fields we were doing crop rotation, which you have to in organic. So corn, wheat, and soy. We're just kind of doing that. And then you got another harebrained idea, which was, why don't we try our hand at hemp? Because by that time THC was starting to get legal in some states, and hemp was, of course, strangely following suit. Some states do hemp, some do THC, some are vice versa. We were like, oh, that could be a big cash crop. We could use the organic land, it's certified organic, that'd be a differentiator in the market.

I had just sold LeadMD when we put in our first crop, so I'm basically funding this thing at this point. We hired workers and brought in tons of specialized equipment. My dad and my brother went back and basically were the feet-on-the-ground operation. And man, hemp is a hard business.

It was a hard business, first and foremost because you're dealing with basically day laborers, fractional staff that you've got to bring on, which aren't always the most reliable people. My car broke down, my meth pipe broke, all that stuff. That part is difficult, but what is even more difficult is the fact that you basically see the only people that succeed in either THC or hemp are vertically integrated operations. So unless you have a retail product, where you can say, okay, I've built a market segment that wants this, I've built a brand in that space, now I'm going to vertically integrate and basically control my own destiny, those are the only brands that are succeeding there. Hemp, and even a lot of marijuana, THC, is just a commodity now at this point. It's really kind of a race to the bottom, where it all trades on these broker sites and so on, unless you have that vertical integration.

So this is the first season where we haven't done everything. We just did everything as the organic field crop. But at the end of the day, it's not really a business as I would think about it anyway. It's something to do. I bought that farm from my parents in 2021 when LeadMD sold and gave them a means to retire and so on. It's a home base for the family that's not Arizona. I guess if the American experiment fails, we have a place to run back to. But it's a different walk of life. It's where my grandparents are from, generations of German immigrants coming into that area of Missouri. The closest town is 20, 25 miles away, a little town called Hermann, which is a German enclave that does tons of Oktoberfest stuff, a lot of great culture. So it's all an investment in that aspect, I would say.

Columbia? Very close.

Okay. So by very close, I mean like an hour.

Okay. So it can't be too far away. So it's in Montgomery County. And about an hour and a half total from St. Louis. Some people have actually heard of Hermann, because it's the only place in the state to get decent wine. Missouri fancies itself a wine state, but it's all sweet, watermelon and strawberry and crap. They actually make a really good Norton, which is the grape that grows back there. A lot of people have actually been there, wine tasting and stuff like that, right?

Risk tolerance, number one. I would say infectious optimism. And I feel like I should have three ingredients to this: risk, infectious optimism, and a healthy dose of fear.

So I really do think one of my personal characteristics that led to success is I am, and maybe this is my history and where I'm from, incredibly fearful and paranoid that this will all go away tomorrow. So that's really, I could say it's passion or this aggressive nature to always achieve, but it's all driven by fear. I always have that in the back of my mind. Everything could go to zero. Are you planting enough seeds? Are you doing enough stuff? Since I've had my exits, I have done a lot of stuff, which is the thought process of, hey, I'm not going to miss on all these.

And I just have that nature, I always want to be doing something. I think that all is just born out of the fact of, again, what's the alternative? What happens if we don't? And I don't like the answer to that question very much.

It'll be somewhere.

Fundamentally, you need to have a strong understanding of what motivates and drives you. And mine is leading into the next aspect. I love that Lombardi quote. I don't want to steal people's answers as mine, but that relentless pursuit of perfection, knowing that you're never going to catch it, but in doing so you'll achieve greatness. Mine is this intense desire to be beholden to no one, knowing that that's an impossibility. That's what motivates me to do things. The reasons for that are obviously, hey, I want to create something for my family and their family and the great people that are willing to roll up their sleeves and do whatever it takes. But you've got to have an incredibly strong, centrally motivating thesis.

And then with that, you have to maintain humility. You can't ever think that you're better than a certain task or tactic or whatever it happens to be. I'll say it again: never asking someone to do something that you wouldn't yourself do. I think that blue-collar work ethic aspect is just something to always maintain. I see people step over that every single day, where it's like, I don't do that anymore. I really do feel like that's my secret sauce. I will do whatever. I'm our IT guy. I have accountants and lawyers and so on, but I'm in that stuff every single day. Whatever needs to be done, in search of and in pursuit of that ultimate goal.

Oh, God. I would just, well, certainly if any of this stuff is interesting, I will show my book for a minute. Not because I even care about selling this book. Not because I even care about selling it, but I really do believe in what we describe here and the fundamentals that it's rooted in. People are everything. Relationships are everything. And by pursuing both of those, success is almost a foregone conclusion. I truly believe it. So you can check out the book.

The Go-To-Market Cheat Code. And you can find it literally anywhere books are sold, but Amazon's great. If you pick it up and you leave us a review, we would greatly appreciate it. But more so, I would love to hear, hopefully, how you've implemented some of this stuff, because it's the root of everything that we've been talking about here today as well.

Thank you so much.