From Addiction To Acquisition With Ryan Shank

Welcome to Forward Obsessed, where we talk to breakthrough business leaders and rising entrepreneurs about their journeys, origin stories, and aha moments.

On this episode of Forward Obsessed, we spoke with Ryan Shank. Ryan Shank is an entrepreneur, operator, and the stories that he tells in this episode, I think you're getting a lot of value from. You're going to hear about what it's like to be a first-time founder, what it's like to go from a number 3 in an organization to a number 1, starting your own organization. The founder jitters, the ups, the downs, the exits, lawsuits, all the different things on the roller coaster of business that is entrepreneurship. It's about being forward obsessed. And you're going to hear how Ryan did that and how now his latest venture is already quickly establishing MVP and product market fit. So he's breaking all the odds and you're going to talk about how to do that too. I really, really love the vulnerability that Ryan shared with us on how he dealt with addiction and the different things he had to develop non-negotiables in his life with respect to his own growth, personal development, mental health. So please, please, please be sure, as always, if you enjoy this episode, share it with somebody, like, subscribe, and give us a review. 5 stars please on whatever platforms you're on. It really helps the show go a long way and keeps helping us go. And remember, stay Forward Obsessed.

Hello and welcome back to Forward Obsessed. Today's episode, we have with us Ryan Shank. Ryan, thank you so much for coming. To the show. You are an accomplished entrepreneur that has rose to companies that have exited. You've started companies that you've exited. We're just really happy to have you here today. Tell us where you're coming from.

Hey, thank you guys so much for having me. Beautiful campus here in New Haven. And took the train up from New York City today. And Yeah, excited to be here. Excited for this conversation.

So we often like to start the show by going back to your past, digging for the kernels that might have created who you are today, and also giving the listeners a little understanding of where you come from. So were you born in New York?

No, I was born in Ocean City, Maryland, actually.

Ocean City, Maryland. Okay. Tell us more about that. Mom and dad entrepreneurs or?

So my mom was a schoolteacher and my dad worked at a poultry company. So Ocean City's on the Eastern Shore of Maryland, so there's a lot of chicken as an industry— Perdue, Tyson's Chicken, that sort of thing. And a few of my friends' dads were also in the poultry business. So they weren't entrepreneurs by trade. My mom had a bridal show that she was always kind of like working at when I was growing up. So, you know, I, and I actually never thought about this until like only in the past couple years, 'cause I was like, no, my parents weren't entrepreneurs. But she did, she was doing that where she would like put together vendors and put, you know, rent out like a convention center and like, you know, that's entrepreneur-y. And so, yeah, so I grew up there. My parents divorced when I was 10. So then kind of had like split household. And, you know, I did, and I have one brother, one older brother. He's more of the academic. And I was kind of more, I guess, you know, I was more like social. I was more, you know, kind of like got in a little bit of trouble, not a lot of bit of trouble, but different personality types. And I guess growing up, you know, I was doing like small level, like entrepreneurship stuff. So like back in, call it 2004, 2005, I was like buying stuff on Alibaba and selling it on eBay, kind of the classic stuff that's sort of happening now, but like really, really early.

So you had hustle, see, because your mom was hustling and you picked up that Yeah. Did she shape you there? Like, do you think that seeing her sort of book the shows and booking the vendors, like, did that influence you? Like, you can get in the middle and sort of work that arbitrage between Alibaba or anything like that? Or do you look back and think that that could have influenced you?

Potentially. It's hard for me to attribute it to that specifically. But, you know, again, I was like young at the time. So maybe like even subconsciously, you know, maybe that it showed me that like you can sort of put things together and create things from nothing essentially. And then, you know, I think I also was picking up on just like other people doing stuff. Like I remember I had a friend in high school and they're like, my brother sells Juicy jumpsuits. And I was like, what are Juicy jumpsuits?

Oh man.

I don't know if you remember that.

Of course.

We pitched Juicy. That's a fun story.

But yeah.

Yeah.

So then I got into like bought all these like and I think they ended up being fake, but I bought all these like Lacoste polo shirts from like some place that I thought was maybe like a distributor or like a warehouse, but it might have just been fakes. And then I was like selling them out of the trunk of my car in high school. And then eventually towards the end of high school, me and a buddy started a clothing brand called Koloko. That was— Koloko means local in Hawaiian. We're from Ocean City. So there's this whole like locals aspect and we wanted to have, you know, like local designers and models and everything be like local to a specific area. And the idea was like we would have different shops in different areas, and it would all be like locally sourced, um, with all like the vendors and everything.

So yeah, so, uh, you and your friends started the clothing company. What inspired you to venture into the world?

What made—

was it just out of like necessity for money? Was it actually that you wanted to— you thought you could build a clothing company? Like, what was the inspiration behind the clothing company in high school?

So, I mean, I think ultimately we wanted to make money. I think we also just wanted to— I think we thought we could do it right. We were like, we can do this. The other thing we were doing, which I thought was kind of cool, which I never really tell because I always forget it, but like in Ocean City, senior weekers come there and they get these like wristbands where they can ride the bus for free if you have like the senior week wristband. So we would get the senior week wristbands and then we would— and only for senior weekers, then we would sell them to a lot of like tourists come to the town or a lot of people work there for the summer. So then we would sell the wristbands to these people that were there for the summer for like $20. So anyway, we were doing like little things like that and then we're like, we should make like a real business and like actually do it because we thought we were like— so that's when we first recognized that we were really good at sales because like in high school, like I graduated high school in 2006, like sales wasn't a thing then. And so, you know, you don't learn about sales, you kind of don't even really hear about it. As like an industry, right? And if you did, it was like you're like slummy car salesman. Like I remember one time in middle school, my teacher was like, you're going to be like a used car salesman. It's like, okay.

It's like the biggest insult someone can give you when you're in middle school. It's like, yeah.

It's often the case when you're good at sales and someone is not, there tends to be the reflection that they put on you or the perception that they have for you is that you're a used car salesman. Salesmen because they're uncomfortable selling. And that's what happens often with lots of people. I mean, I've been called a used car salesman by him at points in our career when we first started working together. And he would think that sales was like slimy and that it wasn't something that had a profession with integrity because people are afraid of it. But it's actually not the case, obviously. And there is no lifeblood and no business without sales.

I mean, also it's like if you're selling a great product to someone that needs your product, like that is actually noble. Yeah, you're like, I'm showing you that I have a solution to a problem and you're explaining how it's going to, you know, solve their problem. Like, that's, that's amazing.

Yeah.

Yeah.

I think if you're selling vaporware or something that, you know, has deficiencies in it just for the sake of sales, that's when you're a scumbag salesman. But if you're selling something that, you know, has a purpose and a use case that someone needs, then it's obviously the lifeblood of the business. So I'm so curious, having been in sales, been so social and in and being a hustler, You then pivot to go to pursue a degree at Clemson in financial management and accounting. What made you choose that as a major?

I heard all the people. I thought all the money was in Wall Street. I said, I thought you're supposed to be an analyst, you know, go to Wall Street, work like 100 hours, sleep under the desk, but then you'd make, you know, like $180,000. And I thought that was the path to just making money.

Got it. So money motivated. I mean, I was the same. I mean, I did anything possible to earn money as a kid. I mean, you used to design flyers for rappers when I met you just to bring some extra cash in, right? A lot of us will do what we need to do out of necessity.

I also thought it was interesting though, in school, like the modeling and creating and that. And I actually felt that I was really good at that, which, you know, again, I didn't know about that going into school or anything. But, you know, once I started getting into like the upper level, like finance courses, I was like really interested in, you know, building the models and like kind of seeing how things would shake out, doing like weighted average cost of capital and stuff like that. I was like, oh, this is actually really cool because I think, you know, I'm wired also as more of like a math guy. So, you know, I actually think that, you know, there's the argument of like, is college worth it? Is it not? But I just think like, first of all, the discipline of it is super valuable. But I also like think I learned a lot. And especially I was able to take like the skill set of like modeling and being like, you know, able to sort of look at numbers and, you know, especially if you couple that with like sales and stuff is actually like a really valuable skill set to have.

Absolutely. We say it's the plumbing of a business. And I wish that I had spent more time in college learning it because I didn't. And I had to do a lot more work after the fact as an entrepreneur to try and keep up with, to make sure that I understood how the business was performing.

Yep, for sure.

Yeah. So you said startups weren't hot, which is one of the things at that time is what made you join Yext specifically on the sales side. So when you say startups weren't hot, help me understand what that meant to you in terms of was that like because of where you were living at the time? Was it because of just like what was happening in the economy? Just want to get a sense of—

So like when I went to Clemson, I didn't even have an iPhone. Like I didn't get it actually my whole— sorry, even when I graduated Clemson, I didn't have an iPhone. So when I say startups, weren't hot. I just meant, you know, it was early in terms of just like timing. That Facebook movie hadn't come out. I think that like really glorified it. Like Zuck was the man, Sean Parker was the man. Like that was just cool.

Now he's just got shirtless six-pack abs pics.

Dude, he's fucking awesome. Like he's the boy. And so, so yeah, I just think it was early. Like there was no Uber. There was like not a lot of this stuff was there. By the way, I actually started this club in college that basically is the Airbnb concept. It was called SHIPS, Students Hosting and Informing Prospective Students. And the whole idea was almost like Airbnb. It was like, if you want to go to a college, don't do the bullshit campus tour where you're going to like look at like these buildings that you never go to and the housing that you might live in as a freshman, like stay with a real student and get hosted by like an actual student, go to a game day, go to all this stuff. And we created this like club and it was awesome. And I was like, dude, that literally is Airbnb. Wow. I mean, it wasn't obviously, and everything's about execution and stuff, but the idea, you know, was there.

It's smart. It's like the Glassdoor of universities.

Exactly. Yeah. So it's like a lot of kids just go to these schools, like their parents will take them, they'll stay in a hotel, they'll do the like official campus tour. You'll go to like these—

It's so lame too. Yeah.

It's like you don't even go to those buildings when you're actually at the school. Like maybe you'll go to like, these random office buildings or like whatever. But it's like, that's not what the kids actually do. So anyway, I thought that was interesting.

But did anybody ever do that?

What's that?

Do you ever look into it to see if anybody ever executed some kind of marketplace like that? I haven't looked into it because it's a great idea. I mean, I hate to shine light on Glassdoor because I think they're a piece of shit company, but I do think that that concept mixed with the Airbnb with someone to stay with where the student gets a little bit of money, but they're also able to show the school in an interesting light.

Yeah, I would sort of tweak that to something a little bit more positive, right?

Great idea.

Which is like, if you think about like food and wine tours or like museum experiences, I know I met a guy recently who did like a museum touring company and he ended up exiting it. It was really successful. He was like ranked in New York Magazine, all these different things and like coolest places. And like, that's a pretty experiential type of concept, right? Versus like, it's not just a website with feedback. It's like, this is the website would have the feedback on it, right? But like, being able to go and actually do those tours. A lot of different folks can create some things. I can see that that's definitely got some legs. So what was that like? So I don't have a background in business development, which I'm guessing you figured out 'cause my co-founder here told that. So when I think about sales, my early exposure to people in business development was folks that were selling products that they didn't believe in. And as a result of it, it kind of had that Wolf of Wall Street type of feel or that Boiler Room type of feel. If you remember the movie back in the day, Vin Diesel selling stocks and whatnot. And it was like, it was very disingenuous. It was people that were kind of hawking things and they, you know, they just were peddling products they didn't believe in that didn't really solve problems, you know, whether it was a Cutco knives or whatever it was back in the day. Right. So here you are now, obviously super smart, like a chill guy. You now get into your first sales position and now as sort of a post-college type of thing, if you will. What was that first exposure like into the field? Like, how did it not feel like used car sales been in business for you? And then take us through how that story ultimately really what I would say sparked a career in business development that then turned to ops and entrepreneurship. But I'm just curious to take us down that journey, if you will.

Yeah. So, you know, getting the job. So basically it's like, how did I even end up there? Well, it was pretty much my only offer out of school. It was like, hey, take this, you know, sales job in New York City. At this startup. And I was like, startup? And it's like, you know, and I think they were like calling themselves an internet startup. I was like, whoa, that's crazy. But it really just opened my eyes to startups in general. They were just coming off of raising a Series B, a $20 million Series B. They had this two-floor office in Chelsea Market, like on the 7th and 8th floor maybe. Like it was buzzing, it was really cool. And I was like, this is awesome. Sales reps there were like, you know, fresh out of college basically. And they all came— we all came from like similar schools. So like all the kids were like really outgoing and salesy and stuff like that. So it was awesome kind of being in that environment. But so that's what I just learned about startups, about venture capital and sort of just like learn the game really.

That's awesome. And then obviously with, with any type of position, I always want to know is like, what was it about that role that or maybe roles that came after it that kind of gave you the itch, the itch where you're like, you know what, I'm ready to evolve from being in business development, doing this thing for somebody else to now I want to do it for myself.

Yeah. So I think it was sort of the repetitive nature of it. I think, you know, initially it's, you know, you're guns blazing and, you know, you're firing on all cylinders and you sort of like— but then I started to kind of look around and sort of just notice the game, right? It's like you hire basically like classes of sales reps that come in, you train them up, you get them on the phone. Some of them don't make it out of, you know, like the trial period. And I was like, oh wow, this is really like a system here. And I started to just kind of like notice, you know, notice that system and be like, I think I could, you know, do this on my own, right? Instead of just being, you know, that cog in the wheel, I was like, I think I could kind of like build, you know, infrastructure like this and build, you know, the bigger thing here instead of just being like, you know, a player in it. And, so I think that itch came from, you know, I'm like, holy crap, like I can't make 100 cold calls a day forever. And like, it was almost scary, you know, every day it's like you're sort of dependent on yourself to go in and like perform, at a high level too, right? It's fairly competitive. It's hard. You're calling, you know, we were calling SMBs, you know, all over the country selling them, you know, pay-per-call advertising is kind of like the product that they were doing then, which is in the lead gen space. So, Yeah, it was really more of like, can I do this on my own? I had, you know, I have and had confidence that I could. So I was like, you know, you know, I want to, I want to try to see if I can figure something out where I can build this sort of like organization.

How old was I here?

23, 24.

So that takes, that takes a lot. It's also obviously it's brave, but also at the same time, it's, it's somewhat, I mean, we did the same thing. We started at 24 and 26, our first, our first company. You always feel like you can do it better. So you had the models, you then you went to go work at M Help Desk first, right? And then after that and then watched, saw that through to an exit and then started your first company where it was your baby, correct?

Correct. Yeah.

If just going back for a second, I think this is really important for the audience, especially the younger audience. Do you think out of college, your first gig, Yext, you learn the deal, you see how this machine works. If you had started right then and there, you think you would have been successful?

Hell no, absolutely not.

So talk more about that. What do you think would have happened?

I didn't know the game at all. Like I didn't know it. It's also important, you know, and I'll talk about this in a second that you have a great product, right? Like even coming out of Yext, like I didn't— I wasn't a developer, right? I didn't have a product really that I could sell. And that's why me teaming up with the guys who initially like built mHelpDesk was a perfect match because I was a sales guy. They were software engineers, right? They came from Lockheed Martin. They built this product. I'm like, I know how to sell it. Let's join forces. Coming out of college, like, again, I did not know sales, the sales game. I did not know I'm first of all, like, I didn't know SMB. You don't know anything in college like that. Like, you're not exposed to like, especially in that world, SaaS or even like lead gen, right? Like, I didn't know about clients, enterprise clients, SMB clients. I didn't know about, you know, compensation plans, anything like that.

Even the language of it, right? It's like, you know, when you first get out of college, like, what is SaaS and SMB and all these different things? Like, you know, and like back then it wasn't as easy, you know, easy to ask ChatGPT or ask Google for an answer to these things, right? It's like, you have to almost learn the language of like all what these things mean. Like we're throwing these terms around, we all know what they mean, but you know, when you're first coming in, you don't know what those words mean.

Yeah.

Well, I asked the question only because I think that in today's world of sort of instant gratification, like the Uberification of everything, everybody's sort of watching like Hustlegram and TikToks and like all these people that are so-called making it. And they think that, you know, at 22, 23 years old that they're just gonna, yeah, I can do this and they're gonna jump ship and start something. And I think, 99% of them probably, you know, that's a made-up number, but I think 99% of them fail as a result of that sort of ignorant bravado, right? I had it too. I remember when even our first year we did $500,000 in sales in our first company. And, you know, I ran out and I was like, I'm going to go borrow money from my, from my father. I'm going to see if he can lend me some cash or help me with a little bit of a line so that we can get ahead. And he was like, no. He said, you got to go one step at a time. And I look back and I think about this all the time. If I had taken that money, I probably would have lost it on him. Because I was too immature at the time to really understand that I didn't know what I didn't know. So I appreciate you sharing that. Some people are like, yeah, I would have fucking crushed it.

But yeah.

So what was that like? So you were a COO at Emscript, right? So, and I would imagine, you know, had some equity position at that point, even though technically didn't find it, found it, you were kind of a key leader in the organization. What was that like sort of leading up to the acquisition? I'm curious to hear like, how do you go from a business that clearly you're coming in systematizing, obviously your systems mind, your accounting finance mind is really your best of mind. You're bringing all these tool sets to the table, which ultimately leads to a really nice exit. But what's that buildup part happen? Like what I wanna understand for the audience is how do you go from like, I'm grinding and I'm building to now all of a sudden we have this exit moment. You know, people talk about the grind, people talk about the exit, but what happens? What's that transition point in between?

So it was, it was a, it was a long, like, ride. I think we built it to over 80 employees, ended up selling to HomeAdvisor.

Right.

Which is like the largest, you know, home services marketplace owned by IAC and Angie's List. I think, you know, it was a lot. You know, we, we would go through sales reps, we would figure out, you know, how to hire, how to fire, what metrics we needed to track. There was a lot of stuff going on there. And yeah, we only raised a little bit of capital. So, you know, it was nice. We weren't like overfunded. We were very disciplined.

And did you approach them or did they approach you?

We had a lot of inbound, so we were making a lot of noise. We were doing a lot of press stuff. So we had a lot of inbounds and we ended up just raising from one like local VC that we became friendly with.

Right on.

So just for the audience, what was mHelpDesk?

So it was field service software. So we basically helped anyone who sends someone into the field like electrician, plumber, manage their work orders, scheduling, dispatching. There's products now like ServiceTitan that are like really big in the space. But yeah, that was the product. So we would basically replace like the clipboard back then for a lot of these service businesses.

So were you recruited into that? Like, how did you meet the founders and the other founders and like, what was the journey to get to mHelpDesk?

So I met Vincent, the CEO, at a startup event in D.C. I was briefly working, you know, after Yext for this company called Repair.com. And, you know, I met him at this startup event that Repair.com sent me to. I was like, I have to go to this event and met him there. He, you know, was doing mHelpDesk with this other guy, and he was trying to basically see if repair.com could use mHelpDesk. And I was like, look, repair.com was inside of this larger, you know, multibillion-dollar insurance company. And I was like, they're never going to do it, but I'm looking to leave here. I was just, you know, in New York selling to these same type of, same type of servicers. I'd love to see if there's a way to work together. So met him at that event. We started talking over the next few months and then eventually realized that, you know, look, look, if we want to do this, we all have to go all in. And so I was like, I'm going to quit my job. You guys got to quit everything else that you're doing and let's all go all in together. So it ended up being, you know, a perfect fit, but only after, you know, meeting by chance at this event and then, and then talking over the next few months.

Looking back at that time, and I know obviously you had a successful exit and you made some cash. Looking back, were there— what could you talk about? Any of the pivotal moments during that first run, that first journey like that you can remember that might have shaped things differently for you in the future?

So on the positive side, I learned, you know, how to build— how to truly build sales teams by doing it. You know, I'm not going to say myself because we did it as a team. But, you know, before at Yext, I was like just a part of the team. Now I'm part of you know, the hiring, the modeling of like, what do the sales reps look like? What does ramp look like? What does comp look like, like with ramp? So on the positive side, there's that. And then in addition, how important, you know, product is and even customer success, right? Because we would sell sometimes, maybe oversell, right? And then customer success or onboarding would then get the customer and be like, what the hell? They need like these features that like we clearly either don't have or they're like weird workarounds and it's like not a great experience for the customer. So really learned about, you know, setting expectations, especially during the sale. And then also like, you know, sales don't matter if the customer is just going to churn. It's all about, you know, like net sales and sort of retention. It's like, what is the sale number at like at the like 60-day mark? So it's like, especially if it's a month-to-month contract where they can cancel out. So on the positive side, there's that, I guess. You know, some of the lessons, there was tons of issues. Like, it was an example.

Yeah.

Yeah. So like one example is, you know, I wrote a blog post about a former employee and got sued for defamation. Right. I didn't say his name or anything. We were just trying to pump out content. But I wrote this blog post and it was in one of those like back, you know, Forbes like contributor articles that you can kind of basically get. No one really reads them, but they're good for backlinks. And I wrote this article just like, here's why you should never courtesy hire and like ended up getting a lawsuit against us. So we had to deal with that.

Like got a lawsuit.

Yeah. Like a real, not cease and desist, not take it down. Like a real filed lawsuit that we had to spend hundreds of thousands of dollars and ended up settling.

Oh man.

All because you wrote a blog post.

Mm-hmm.

But so I don't, I don't want to open up old wounds. Right. But So you didn't mention a person's name. You talked about a particular topic, which in this case was Curtis Sayer. If you're okay with talking about it, we can skip over if you don't want to, but— No, it's fine. At a high level, so you write a blog post, which is a part of your entrepreneurial journey, right? And then someone files a lawsuit against you and the lawsuit was based on defamation of character. So how could that person successfully articulate that? That's—

Yeah. So what I learned was that defamation, you don't have to say their name. They just have to be easily identifiable. Which is, you know, obviously subjective and it warrants enough merit for the suit to actually at least get filed. And then you have to have lawyers to defend it and go back and forth with their lawyer and stuff like that.

And then it becomes a who wants to settle and not spend money and time.

Exactly. Yeah.

So yeah, that's the—

wow.

The love.

Okay.

Just, just curious. So let's say I want— let's say that I own a coffee company and I hire an employee through courtesy hiring, which I don't know what that is, but I'm getting, I'm getting a sense of what it is from the words. And let's say that I, I fired that person and I write an article about why you shouldn't courtesy hire as a coffee company owner. Now I've had 20 or 30 baristas that I've hired and for whatever reason, hired, fired, whatever. Yeah.

So I think, I think the issue is I was probably like, here's why you should never courtesy hire. We hired a barista last July and then it was like identifiable.

So specificity was there. So if it was more generalized, you'd be okay?

I believe so.

Okay.

I'm not going to do— I'm not going to go down that path. Yeah, but I believe so.

Understood.

Got it.

So, yeah, so what I'm— so what I'm hearing there, just to, to kind of, to move past that, because it sounds like a terrible part in the journey, sounds like you dealt with a lot of people challenges. I'd imagine people's expectations, people's sense of entitlement, maybe those kinds of things, you know, as a, as a leader What's some advice that you would give to your younger self on when faced with these issues, which everyone's gonna have people issues, right? What are some of the lessons you wish you knew then that you know now?

I also, so another people issue too is, you know, employee, sort of showing employees like a path, right? I think a lot of employees feel similar to my story at Yext where I felt like a cog in a wheel. Like you really gotta show them the path of growth, right? And show and really like communicate that, you know, I think pretty frequently. So, so a lesson would be, you know, just overcommunication with everything really, right? Whether it's comp plans and how you get comped and why you get comped that much and then showing, you know, market rates and why, you know, this is actually like a fair compensation. And then also, you know, really showing people, hey, you're really part of like, you know, continue to paint the bigger picture always. I think, you know, you get— we get so stuck in the day to day that we, you know, these are people and their lives and they talk about their work at home and like, you know, it's their lives.

Sure.

So I think like really painting the bigger picture and the bigger why is really important for people to be able to like see like, hey, I'm part of like something bigger and magical that's happening. And I don't just show up here and, you know, make my sales and go home.

Right on.

So really just being able to instill a sense of purpose and make sure that as a leader you're putting vision in place where people can see themselves in that picture and that vision. And how that can attribute to their life and their growth. So what's in it for them?

Right, exactly.

Right on. I appreciate that. Any other like stories that come to mind for you that you feel like the audience would really find valuable, or should we keep moving?

I mean, there's, there's some like interesting stories. Like we fielded some early acquisition offers. So, you know, some of the stories were, or I guess lessons really were you know, do we do this or do we continue on? Right. And we had some like pretty big offers early. Like we had been doing it for maybe a year and a half, getting like a $13 million offer from a pretty big company. We would engage one of our advisors to sort of help us. We were negotiating that deal and then just being able to like walk away from that and say, and just like have confidence like, hey, we're going to go way bigger. So like, I guess, you know, a lesson from that would be you know, if you do have confidence and also it's like if you are on to something like these things compound over time, it's like it is hard to like say no early. But, you know, there's classic stories with like Zuck turning down, you know, $1 billion and Snap turning down a lot of money. But it's like, look, if you're on to something, sometimes these things, you know, and I've heard like Jason Lemkin.

Yeah.

And certain people like that talk about this. It's like if you have, you know, product market fit and a product that's working and you're like, it's like just stick it out because these things compound. And they're going to be worth so much more over time.

Yeah, no, I love that. One of the things I'm hearing from you, which we haven't talked about yet, but I want to poke on, is you strike me as a very talented marketer. And when I, when I did my research on you for the show today, I didn't see marketing come up a lot. But one of the things that you said is it sounds like in both these organizations and we haven't even gotten to the phone line yet. Right. But both these organizations, you got a lot of inbound, inbound acquisition opportunity, inbound, you know, in different ways. What was it that you were doing, whether it's just the principles or the thinking or the strategies that ultimately led to all that interest? I'd have to imagine pretty crowded space in the previous job and organization. But for you to be getting these acquisition opportunities so early, year and a half in is what you're saying. You had to be doing something right from a marketing perspective, if I'm hearing you correctly.

Is that— did I read that?

Yeah. And as you were saying that, it's like outbound create— like creates inbound. You know, so we were doing a lot of, we were just trying to make noise as much as possible. We were, you know, pitching press all the time on different stories and different, you know, things about us. Oh, M Help Desk is growing from, you know, 13 to 30 employees. Like any type of like story, we were like pitching press.

So you're doing that yourselves? You didn't have like a PR firm or something?

No, yeah, yeah. And, you know, we were, I mean, we could have been creating, you know, more. And I did a lot with PhoneWagon, which we can talk about in terms of like creating content and doing like outbound stuff. But like, yeah, I think like with a lot of this there was just a lot of, you know, I think the product again, it kind of comes back to product. The product had product market fit. We were getting a lot of traction there. We were also in an incubator at AOL with a bunch of other just at their campus. They're pretty— they didn't take any equity or anything, but they had a huge campus in Northern Virginia.

Right on.

And we were out of there. So then other startups sort of like saw us working and then that created chatter sort of like in the D.C. like tech community.

Right on.

So yeah, it was really about sort of just like making noise, whether it was with press, whether it was with like videos, whether it was with just like other startups attending events. We just wanted to like sort of be known. And then I think that's when like eyeballs came on us. The other thing, by the way, where I think, you know, the acquisition offers came in is we would like, we would really, really ask a lot of our customers for reviews. So we like basically seeded all the online review sites for anything with like software reviews, you know, Capterra, G2, like all those software advice, all those. So we had all of these like like reviews on all these different sites. So I think like a lot of times, like even VCs, I think look at those sites to see like what products are like ranking high. So we did that super early back then, like 2013, 2014. And I think that's, you know, where people started to see like, wow, they have like 150 reviews. Like that's a lot.

That's awesome. So really content strategy was tight. Just one quick, quick thought on that, Dave. So if I'm a startup founder and I'm trying to figure out how to make noise from a press perspective, where would you suggest I start? Because that's the thing that I know a lot of founders, it's like, okay, that, that's the first question I have. And then I've got a follow-up to that just to hear your, your thoughts on something.

I would pitch individual writers, like don't go to Info, don't pitch them all, like target specific writers. Like I remember, I mean, this is kind of like nitty gritty and stuff we were doing back then. But like this TechCrunch writer, John Biggs, I remember back in the day he was like in DC at some event and then the event ended and he needed a ride. Like I gave him a ride to this, you know, to wherever he was going, you know, after some event. And just like, I feel like we were doing like scrappy things like that. Like we were just like everywhere and we were like pitching people. I was like finding, you know, phone, like not being like too crazy, like too, too like too much. But, you know, if I could get a writer's number, I would text them. If they said like, no, like I wouldn't like blow them up. But like pitching the individual writers with actual stories, I think is like, is where what you should do in terms of press.

So how do you come up with the stories?

You create the stories, right? Or you have the stories.

So great business development, right? Figuring out what the story is around it.

Yeah.

My follow-up for you is one of the things I like to do is ask people to define something because I think that everyone's mental model is different. When you say product-market fit, what does product-market fit mean to you?

Product-market fit means that customers actually need your product. They're not just courtesy buying it, back to courtesy, you know, because they're your friend. They're not buying it and not using it but not canceling. So then you think, you know, you have product-market fit, but they're like using it and it's actually making their lives better, right? You're solving for a problem with a real customer.

I love that.

Yeah, thanks for sharing that. It's because it's like a widely known thing, product-market fit, but I think there's a lot of nuance I'm hearing in terms of how people are describing it and the stickiness of it and that sort of thing.

So thanks for that.

You were going to ask something. Sorry about that.

Well, I was going to say, I mean, business development and PR, I've often— I have always said are the same, right? You just— it's outreach. It's like outbound calls. The question is what's the story that you're pitching? And obviously there's some nuance and some things that you have to learn, but I think it's important for the For the viewers and the listeners to hear that like PR is reaching out to people that write stories no different than you would reach out to somebody to buy your product. You're asking them to buy the story versus the product. So you'd be naturally good at it. I think that's fantastic. But so now I want to walk into the back to, to M Help Desk. You raised a little bit of money and you obviously got acquired. Were you a part of raising the capital? And so what was that journey like for you?

Again, it wasn't a crazy process because we were getting a lot of inbounds. It was pretty much like we took a few meetings. We were going to take, um, we were actually going to raise like a Series A, and like as that was happening, we got the acquisition over. So we never did that. We basically only had like, call it a seed round. Um, and it was, again, at mHelpDesk is a lot different than PhoneWagon and other companies because again, we were, yeah, so that was like almost easy. It was inbounds. We were already at almost a million in ARR before we even raised, and we pretty much set our terms, like it was very different than a lot of people experience and that I even experienced later.

It's also, yeah, it's also 2012 to 2016 is a bull market. Yeah.

Yeah.

So exactly.

And we were early in our product category, like again, like ServiceTitan hadn't happened. They're now a multibillion-dollar company worth like $7, $8 billion. They got funded by Bessemer. Like our category was super early, which I think also matters, right? Sort of like what you pick to go after.

Yeah.

So it was hot and it was early and we were getting traction and Yeah. So I think like we were in a good unique position then with raising.

And then so then, so then walk us through the acquisition to HomeAdvisor.

What was, what was that all about? What was that?

What did that feel like?

It was awesome. So they, again, they came inbound and it's funny. So, so Yext, the company I used to work at, eventually spun off the division that I worked at. They renamed it Felix and sold it to IAC. And that was actually then rolled under HomeAdvisor. So I think the story goes, this guy, this SVP from HomeAdvisor was in the Felix office and he was talking to people and he was like, hey, we want to acquire a field service software company. We're looking at, you know, Jobber and a couple other players. And one of my friends was like, you should check out mHelpDesk. This guy used to work here. So he— they came inbound to us and we're like, hey, we want to, you know, see if there's a deal. And we're like, oh, hell yeah, you guys have 100,000 service providers that we could sell to. So we ended up like meeting with them. They actually flew us out to their campus in Golden, Colorado, like outside of Denver. We met the team and we're like, these guys are awesome, right? It's a sales organization. We were a sales organization. They have, you know, you know, 200 sales reps, right, hitting the phones, calling servicers for lead gen products. And we thought it was a good fit. So it was, it was nice because again, we had talked to a company before that, that we fielded another acquisition offer and it was like, I think there just like wasn't that connection. Like they came and saw us one time, but I think we just didn't like love each other. Whereas like with the HomeAdvisor deal, like we went out there, we would go to dinner with like their CEO, this guy Chris Terrell. He was the man, their SVPs. Like it just felt very like family. It felt, it just felt good, you know, they weren't— we felt like they weren't like dicking us around or anything. And then so basically the deal ended up being they would— they bought 51% of the company, which I thought was an— so I think this is an interesting deal structure that IAC does frequently, which in my head, especially theoretically, it's a good win-win situation. So they bought 51% of the company and then they create put calls to buy the rest of the company in future years. Right. Put call— anyone you can call to sell, they can call to buy. So pretty much there's going to be a sale. At future market value. So you're really incentivized to like keep grinding at the business and get the valuation up because like your future money depends on it and there's guaranteed liquidity in the future. So the deal was like really interesting. So we took money off the table in 2014 and then the rest of the money came in like '16, '17, '18. And, and we were able to then leverage, you know, their entire, you know, customer base of like 100,000 servicers. So it was like a really win-win deal structure. And they ended up, look, they ended up then buying Angie's List, basically spinning out of IAC, IPOing. Like, so it was a cool—

So you, but you didn't stay on for that, the '17, '18, '19, you left.

So the original deal happened in 2014. That was when the 51% happened. And then I left in 2016. So I stayed 2 years after the deal, after, you know, you know, we were able to sort of kind of like become one organization.

Got it. And you felt it was time?

Yeah.

Yeah. So like by that time, again, once you are in a larger organization, you like work for them, basically you're reporting up to them, you know, at that big. It's like in my head, it's like if I leave, I'm not going to— nothing is going to materially change. And maybe that's like the wrong mindset. Like I should be able to like, you know, move the needle here and like, I got to stay. But like, if you're fully vested and like the organization's that big and you're sort of rolling up to even an even larger organization, it's like, how much personal impact can you have? Also, the bigger thing I think is like, I don't think I'm that good at that stage. Like, I think I'm good at like the 0 to 1, getting things off the ground, being creative. Let's like figure it out. At that level, 80 employees rolling up to a large, you know, now public company, it's like, it's all systems and like, ops basically, whereas I'm more like, hey, let's like figure out product market fit and like figure out, you know, can we even scale this thing?

No, I think there's a— I wasn't a huge fan of the book, but there's a lot of people talk about Blitzscaling, that book that's sort of like the playbook. And he talks about sort of like stages. Yeah, exactly. Of the stages and the tours and saying that like what makes a great, you know, chief revenue officer of a publicly traded company is entirely different than a SMB, entirely different from someone who's like the first salesperson at a SaaS tech company. So I think it's like there's all these different stages. So I love that self-awareness that you've got in terms of like, this is where you want to add the most value, where it sounds like you had more fun. I can even hear the shift in you where you're like, one was fun, you're building, the other was like you're kind of a cog in the wheel, you're in this machine, kind of lost your sense of agency, if you will, if I'm hearing that correctly.

Yep.

So Did you leave knowing you were going to start PhoneWagon or did you just leave and say, you know, I'm going to go figure it out?

I left saying I'm going to go figure it out. I had a couple things in my head that I wanted to make sure, like parameters that I wanted to stay between, right? I wanted to, so there's a notion of founder market fit. So like I wanted to stay in my lane, right? Like I didn't know e-commerce. I don't know enterprise. you know, I don't know, like D2C, like I couldn't start like a cool toothbrush brand or anything like inter— I didn't have any experience with that, right? I knew like SMB and particularly SMB SaaS, and I wanted to really stay in my lane. I actually had a friend who, you know, was pretty much in like SMB sales as well. And then he started this like dating app and it's like, that's just so out of your lane, you know, that's like consumer and it's like, that's just really hard. And so I wanted to stay in SMB SaaS. I liked selling to the customers that we were selling to. You know, one of the things that I found was that, you know, they were getting all these leads from HomeAdvisor. They were using mHelpDesk to manage the leads, but a lot of them like weren't contacting the leads quick enough. So like they're all like, we want phone calls, we want phone calls. So, you know, there's a few call tracking products in the market. A lot of them were like heavy, expensive. And then there was also like things popping up at the time, like Dialpad to like basically build like a new phone for, for small businesses. And the other interesting thing is that Twilio IPO'd that summer. So Twilio IPO'd summer of '16. So I was like, you know, do I— I was like, I should do something in the phone space, right? Like you could do it on top of Twilio. These customers, they like value the phone and phone calls, right? So that's where I kind of ended up shortly after I left. Okay.

Like the RingCentral.

Exactly.

Yeah.

There's a hot space for it. Sure.

Was PhoneWagon your idea? Did you meet somebody that had the idea and you sort of attached to it or?

No, it was my idea.

So it was your idea.

Yeah. When I left after like 30 days, I was like, man, I need a product to sell. I was like, I just need to like sell something. So I was like, all right, let me just, and the thing is I didn't want to, and maybe this to a fault, but it's like, I didn't want to like fall into like decision paralysis where I'm just like, what do I do? Do I, you know, Is this big enough? Is it not big? It's like there is a market for it, right? And with this play with PhoneWagon was more of like a differentiation play. It wasn't like, hey, bring a new product to market and figure out if there's product market fit. It's like there was product market fit. It's like, could I carve an angle?

I love that. Now, so what was that moment like for you when you're like, all right, now I've got this idea and now I'm going to go like, where do you go from there?

So it's funny because it evolved a lot. It was like, I'm just, you know, I went on like Upwork and I got some, you know, I like created the requirements. By the way, I'm building a new company now and I'm doing everything so different because of all the learnings with PhoneWagon. But it's like, I was like, all right, I'm gonna get some, you know, offshore devs and, you know, I'll get them to build the product. And then I was like, ah shit, I probably need some design. So then I was like, all right, I'm gonna get a designer from Dribbble. And I was like, I should probably do wireframes too. I was like, maybe I should do wireframes before design. That seems like it makes sense. And I was kind of like all over the place and I wasn't initially doing it like I'm going to go all in. I was like, all right, I'll spend like $50K of my own money. I'll like build something. I'll see if I can like start making some sales. And it kind of started off as like just that. And I was like, okay. And like as the developers were like building, you know, I would like build the website, but I wasn't spending like too, too much time on it, right? Like I would kind of give them a lot of like feedback and stuff and I was like, talking with them over Skype because this is like 2016, like I didn't even have Slack yet. And so it was kind of like that was sort of the approach. And then once I started to get like MVP up and started to get like our first real customer, so I started building in July of '16 and then I got our first paid, like real product, first paying customer in like December. So it kind of happened fast.

Yeah, that's right.

But then like there's this high that happens, right? You sort of get that first paying customer and you're like, holy shit, I just built this product from scratch and now someone's paying actual US dollars for it and they're using it in their business. Like, that's fucking awesome. Like, that's so cool.

Yeah, no, that's— I mean, this is why we do what we do. This is what the show is all about. You know, it's like that. Even just reliving that, I saw like you're like, hell yeah, right?

Yeah, I remember I like, I couldn't even really take credit cards yet. So I was like on the phone because I was like also just doing outbound. And by the way, we should talk about that strategy. But I like wrote the credit card number down. I was like, $39 a month. I was like, you know, you can cancel any time.

I was so excited.

I was so excited.

There was no Stripe back then, right? It's like nowadays you got a tool, you can just Google a tool and it comes up. Back then you had to figure shit out.

Yeah, yeah.

A lot harder.

There was Stripe. I just hadn't hooked it up yet because we were like so early with product.

Though it wasn't as easy, right? Like now it's like you can have a Stripe account going in less than 24 hours taking payments with a link and it's like no code required. Back then, you know, give yourself more credit. You had to figure some shit out.

So walk us through the development. Now you're building something on your own from scratch. You got skin in the game, $50K. You just got product market fit. Like give us a little bit more of that story. Like what was that trajectory? Did you raise capital?

So I didn't know that I had product market fit. So this is actually kind of interesting. So had the product up. Well, I know that there is product market fit in general, but I was like, I don't know how to sell this yet, right? So I started calling all these businesses, right? All the HVAC guys, the pest control guys, you know, the plumbing companies. And I'm, you know, making hundreds of calls. I have one of my buddies who I used to do sales with that I gave advisor shares to. We would like sit in a room and we would just like dial. We're like, dude, let's go. Headsets on. Like, let's hit it. And We were calling all these companies and what we realized, well, we started talking to them and they're like, oh, I don't do that. Like, we have an agency that does it. And we're like, dude, fuck. Like all these, no one manages this themselves. So we're like, shit, we gotta go to the agencies. These agencies, you know, and there's like Google certified partners that manage like PPC for these companies and they drive, you know, traffic to a lander and then that would then go to a phone call and the agencies have to prove to their clients that I drove you that call and deliver them like a cost per lead, cost per call.

Used to be a pay-per-click monster back in the day. Yeah.

And there's a lot of verticals that value phone calls, personal injury lawyers, remodeling companies, a lot of those service companies that I just talked about. So I'm like, okay, we got to go to the agencies. And then it's like, I realized, shit, we can sell one agency and get like 20 clients. And then that's when we realized like, oh, that's the play here. Like we got to go to the agencies. And the, you know, the interesting thing is I was like, this is, this is a land and expand, get the agency. Hey, try it out with your next client that comes in that needs phone calls. They like it with them. Let's roll it out to everyone, right? Or can we replace, you know, if you're using, you know, a different call analytics software.

So, so Vertrax or, you know, we had LongTag.

Yeah, there's a bunch of— Marchex.

Yeah, Marchex. Yeah, yeah. Marchex. Yeah, we used like so many of them. Yeah, there were, there was like, yeah.

What was Berkowitz's company's name? He sold it.

Oh, Adam Berkowitz? John. John Berkowitz.

Oh, who?

With H?

Yes.

He's at Austin, Texas right now.

He is.

But he was in New York.

He had a— he had a dialing— no, no, no. He had— but he, he had a company that sold to like U-Haul.

It was like— it's like ReachLocal, but it wasn't ReachLocal.

Yes, exactly.

That's—

you're exactly right.

I didn't think of it, but they sales-focused business. They were dialing for dollars. Big sales.

Yeah.

Yeah.

And they was basically arbitraging pay-per-click and then, and then pay-per-lead. Right. Same, same thing.

Yeah, it's going to bug me.

It's going to bug me.

Me too.

I'm going to Google it. I'm just going to do it. You guys keep talking.

Yeah, yeah. So now we talked to that guy, by the way. I've had a call with him.

Berkowitz?

Yeah.

His brother's in New Haven. He just sold his company, C-Click Fix. They sold it to a Civic tech company, right?

Civic Plus.

And yeah, both of them, they're both pretty successful.

It's just a small world.

Yeah.

So take us back. So, so you start landing customers, you see that this thing's got real legs, right? You know what that feels like. You got that spark that you were just feeling with us. Where does it go from there? Because that's really where the beginning of the rocket ship really started to kick.

Yeah. So what happened? I actually think this is like a pretty important moment is I actually saw that this guy Alex Iskold from Techstars posted this thing on Twitter where he's like, hey, we have extra space in our Techstars office if you want to rent a desk. And I was in New York and I was working out of my apartment and I was like, man, I got to get out of my apartment. So now it's like winter of '17, like early '17, right? And I was like, hey, I would love to. And it's like, you know, a couple hundred bucks a month or whatever it was. So I started going into the Techstars office. I wasn't a part of Techstars, but I was just working out of their office and started to get to know the guys there. And I was like, you know, working every day. And one day he's like, hey, do you want to— would you want to do Techstars like in our summer program? And I was like, I don't— I was like, how much equity do you have to give up? I was like, I don't really want to do that. And then I was like, look, I need the accountability and the structure, right? Because like, you know, just going into the office I think helped me. And then, you know, going through a formal 3-month program, I was like, okay, I see the value there. So Ended up, you know, committing and then ultimately getting accepted and doing Techstars in summer of '17. But I think it, you know, it really happened because I saw this like posting on his Twitter of like, hey, we have extra desks at our office if you want to rent one. So, you know, then I get into Techstars and I'm like, okay, this is in 2017. I was like, I need to create content. You know, everyone's consuming video. I was like, I'm going to vlog. You know, like Jake Paul was hot at the time, Logan Paul, I was like David Dobrik, I was like, I'm going to do— and also like GaryVee. So I was like, can you kind of do the GaryVee style but like kind of YouTubery where it's more like entertainment? And then if you like vlog through Techstars, like that's kind of cool, like a little like documentary. So I hired this kid that I found on YouTube to like move to New York. I paid him like $4,000 or $5,000 a month and he would like follow me around and we would just do like daily vlogs, like every day for 100 days straight going through Techstars. And so that was like kind of a different angle than what everyone else was doing. Like no one was creating like videos like that in the startup scene, especially in like early Techstars. And now if I were to do it again, you know, you would probably do like more short stuff and do like TikTok, but that wasn't really like popping then. But so did that. And like kind of back to your question of like, when did you know you were on to something? Like just going through Techstars and like having a real product and selling a lot of the companies were a lot earlier. And so they weren't, you know, selling like that. So like, you know, I felt like we were, you know, making a lot of progress, you know, during Techstars and like it just really helped in general. Like it helped, you know, make this, you know, create structure for everything. And that's when it just became really real. So now I have, you know, camera guy, I have a product guy, sales guy. So now there's like 5 people on the team and it's like a real thing. Whereas before I was like, I'm just going to do this on the side and like get a product to sell. Now I'm like, oh shit, now I'm in Techstars. I took some money from Techstars. Now we're talking about raising capital at the end of Techstars. I was like, this is like the real deal. And that's kind of then, you know, where then I'm like putting a lot of pressure on myself. You know, I'm a first-time real founder now because before I was like the number 3 guy. Now I'm the number 1 guy. I'm not technical. I have these like offshore engineers that built it. I'm like, I don't really know where the code is or even if it's real. And hopefully they don't like just take it and leave one day. You know, there's a lot of like things that are out of my control but sort of fall onto me. And that's where I was like, you know, and then after Techstars, we raised, you know, like $1.2 million. So we had raised $1.2 million. So now we have investors. So I just, you know, so now it's like very, very real. And that's where I feel like I started to feel a lot of the pressure. And again, most of it was probably myself putting the pressure on me. But, you know, there's a lot of people and I'm also like managing people now, whereas like I said before, I don't really like managing people. I like sort of creating and like figuring it out. But now I'm managing people. I have investors, you know, I like also don't want to fail. I'm creating videos every day. So I'm like making a lot of like noise and putting a lot of like pressure on myself. And that's when I like kind of fell into this like hole where I'm sort of like taking Adderall now during the daytime and like it's kind of just going down this like path of like, you know, bad habits and like kind of got into this like substance abuse issue where I think a lot of founders maybe don't talk about it, but it really happens. And yeah, it started to like really take a toll on me.

Was it— I could definitely relate to that in a big way. I think I almost ended up in the hospital one day because the amount of caffeine that I was taking in was just absurd between the Red Bulls, the Starbucks, whatever. And I remember like the heart palpitations. It was crazy. So I can really on a very small level, was it Adderall because of ADD or ADHD or was it just because this is going to give you like the focus and the edge at that time?

Well, I definitely think I have ADHD, but arguably a lot of people have ADHD. And also it's like, should you really medicate yourself with effectively meth? Is that really like what we're doing now? It's like, so So yeah, I mean, it was, it was, it was prescribed. It is prescribed. But yeah, I think I was like taking it in a way where, you know, I was like kind of using that as like, hey, I'm just going to like go in on work. But it also what happens with me is it makes me like incredibly antisocial. Like, I don't want to talk to anyone. I just want to like build spreadsheets and like look at like formulas and stuff. Whereas I actually think my superpower is the social element and I like being able to talk and express myself and people. See the passion. And when I do that, I like become a ro— like a zombie. So it's like you're literally— I'm literally like taking away like the best thing that I have and then like kind of like becoming arguably the worst version of myself, you know? And then it's like, you know, sort of once you go down that spiral, then it's like you can't sleep and then you're not sleeping and then you're kind of on this like roller coaster of up, down, up, down. And that really like takes a toll on you. And look, we can get into, you know, a lot of that. But I also want to then say sort of like at the same time, like PhoneWagon is kind of booming like we're, we're doing, we started to do well. We're selling to agencies now, you know, we're opening up sales offices. But, you know, one thing that I think, you know, is important to note is that once you raise venture capital, you're sort of like on this venture capital treadmill, right? Like you, you're, you're kind of encouraged to burn the money in, in order, like ramp up spend in order to ramp up growth. But what happened with us is we actually didn't have true, true product market fit in terms of like, so we were able to sell to customers, but we weren't able to sell to a lot of customers because we had missing integrations and features. Like we weren't there yet. We were able to sell to, you know, some use cases, but not a majority of the use cases. So we ramped up sales and marketing before product was there. And it's like we would get into demos and people would say, hey, I love this, but I need a Salesforce integration. I need an integration with, you know, Google Ads and or Google Analytics, something like that. HubSpot. We didn't have these integrations. Hey, I need, you know, a call flow builder. I need to, you know, simultaneous ring. There's all these like little like nuanced features, especially if you want the larger companies. And it's like, so it's like we would get to them, sales and marketing, we would get them in the funnel, we would do the demo. It is a good fit. It's qualified lead. But then it's like we're only converting, you know, 15% of our demos into paying customers. And, you know, there's a huge, you know, gap of customers that we're not closing just because we don't have, you know, the right features and stuff. So we've ramped up spend too early, in my opinion, because the— and before the product was ready to like truly kind of like blitzscale or like really scale it. And a lot of our modeling was like, okay, if we get this many sales reps and this is our close rates, like this is like what the MRR shakes out to be over time. And that just wasn't the case. And I think like Seeing that also like freaked me the fuck out. Like I was like, holy shit, like we're burning $80K a month. We have $800K in the bank. We have 10 months left to live. Like we got to figure it out. We're not going to be able to raise if we're not growing either. So I'm like, are we about to die right now? And like, that is a scary realization as a founder, seeing the burn, seeing the burn that high, seeing your runway and then like you know, I mean, you do have to take a step back and say like, look, we need to do something about this like immediately, right? Because like we can't just let ourselves die. So, so yeah. So I think like all of those things combined, you know, I think as like a founder, I was like, holy shit. Like I was under a lot of like pressure. How old? 29, 29, 30.

Yeah. It's a lot. It's a lot of pressure.

That is a whole fucking, that is a whole fucking lot, man.

Totally appreciate you sharing that, by the way.

And how was your, how were you dealing with, or how do you think your team was interpreting that pressure on you and like your, who you were becoming?

See, this is what ended up happening. I felt like I ended up being the weakest link, right? Like I was the one that would be like canceling team meetings, moving team meetings. I'd have a one-on-one, like, ah, move that. At this time now it's like 2020 also. So like we're all remote. So it's like they maybe didn't like see it necessarily, but like I just felt like I was way more unresponsive. I was unresponsive or like would be so delayed in my communication. Like I felt like I was the weakest link. So the team and I kind of looked around and I was like, man, the team is firing like on all cylinders. Like they're awesome. I have this awesome CTO, this awesome, you know, director of ops person. And so I don't, I don't know if they noticed, but I noticed and I felt it, you know? So there was a— so by the end of 2020, I was like, man, something has to change. And I was like, I'm going to a treatment place in South Florida. I hit up my CTO and I was like, dude, like, I have to do this. You have to run the team right now. I'm going to be like offline for 2 months. Well, I actually went in there thinking I was only going to be in for 1 month and I ended up extending. But I was like, but I have to do this, you know? And I kind of told him where I was at and he's like, all right, let's go. And, uh, that's awesome.

Crazy brave of you, man. Yeah, that's awesome. A lot of people can't do that on their own. Somebody usually has to come in and tell them to do it.

No, that was the other frustrating thing. I was like, God, I'm like the old— so I was like, everyone thinks everything's fine. I was like, it's not fucking fine, you know? So that's like almost even more frustrating when you're like, dude, I know. And you know, there's also a lot of like internal, uh, factors as well. You're like, I'm not living up to like my best self. And especially it's like, dude, I've proven that I'm capable. So then when I'm like sort of not being as capable as I know I'm able to, that like really kind of like messes you up a little bit like inside. And then again, just like seeing the team, like the team is like killing it and like, yeah, so it had to happen.

So this was through COVID?

Through COVID, yeah.

So it's— wow, that is a tough time period. Yeah, that's like a perfect storm. Like literally.

Yeah. I mean, and this is the journey that we're we talk about, man.

This is like, people think the lows are lows. Like, the lows could be literally crazy low for people. They don't even see it coming. Everybody thinks it's all flashy and stuff like that. But like, you're on, you've got COVID to deal with as a founder and a leader. We had to deal with it on various, in various businesses. And then you've got this addiction and then you've got all the pressure of like, people think it's really easy and they get pissed off when people don't give them money. But like, it's a real big honor to give somebody, to give somebody's money, whether it's a person or a venture capital firm that they raised it from somebody and it's a lot of fucking pressure.

100%. The other thing I didn't mention is we were also in a lawsuit, a pretty big lawsuit at this time. So by 2020, we had been in a lawsuit for 2 and a half years. It was, you know, I don't want to get into it, but, you know, it was like, it was basically, in my opinion, anti-competitive lawsuit. Someone saying like, oh, a few lines of code were like a few lines of arguably a few lines of code were taken from JavaScript that's like public-facing. So there was that like sort of allegation, but this like massive 2.5-year lawsuit that we're spending like tons of money fighting. So all of that combined plus layer on a pretty big lawsuit.

That's intense.

Yeah.

Oh man.

So yeah, I mean, that really like, that takes a serious amount of grit to work your way through that. What do you think is the biggest thing you learned about yourself when you had that 2-month treatment?

So I learned that I thrive under structure. You know, going through that was like the first time that I had been basically someone else was like really telling me what to do every single day. And it was fucking awesome. You know, I would go in, you would have your schedule. Pretty much it's like therapy boot camp also. And I hadn't done therapy and I have known that I needed to do therapy for so long. So there was like, you basically just go in and you do group therapy, you do individual therapy, and then you like get massages and stuff. I went to like a really nice place. It was like, it was kind of dope. To be honest. But I learned, yeah, so I learned that I thrive under structure and I actually need structure and that's incredibly important. I also learned that it kind of gave me more confidence in myself that I know when to raise my hand and say I need help because a lot of people are maybe afraid to ask for help and like—

Heroism.

Yeah. And like, You know, it showed me that I know when I need to ask for help, I'm capable of asking for help. And then also like whatever challenge is then put in front of me, I think I can figure it out because I am not afraid to ask for help.

I love that. So just for the audience and even selfishly, I want to ask this question for myself as well is how do you ask for help? And I ask the question because I think a lot of people have that question. I know I myself am terrible about raising my hand and asking for help. There's this like stupid part of me that's like, if I ask, if I'm asking someone for help, you know, I'm gonna just— they're gonna think I suck at life and I'm gonna be imposing on them and all those other things. How do you ask for help in a way that is useful?

So I think it's, uh, I think it's honorable when you ask for help. I also think, you know, people who are curious are the best type of people because they're trying to learn and they're trying to figure things out. I just watched this interview with MrBeast the other day and he was talking about how he's always asking, you know, people, hey, like basically like knowledge transfer me. How do you, how do you do that? You know, as he's leveling up, he's like asking, you know, them to basically like teach him their ways and hopefully he can provide value as well. So I think if you approach the, the ask as curiosity, which it is, right? You're like, hey, like I'm trying to figure this out. I don't know how to figure it out. You could ask, you know, in a way where you're just being curious, you know, and I think people who are curious are like very like intellectually, you know, like, you know, they look for intellectual stimulation. They look to learn. And, you know, that's a way. So it's like whatever problem it is, you know, you're like, hey, I'm looking to solve that. Who should I talk to? And, you know, those conversations just get other people's brains working and then they usually will maybe make a recommendation or they'll make an intro, something like that.

Awesome. I love that. I really appreciate it. I think, I think a lot of people, myself included, are gonna get some value from hearing that. So you've essentially now kind of reconstructed and rebuilt yourself, you know, mentally, physically, etc., in this program. And now you re-emerge into the, the business. You're back, you're back full-time in the business after that.

Yeah, I actually— so, so I initially was like, hey, I'm going to be offline. But really, the place I went, like, we had our computers and phones and stuff, and like, I pretty much online like the whole time anyway. So I wasn't a ghost. Um, I was, uh, I mean, I was definitely dialed back because I was really focused, um, on kind of addressing a lot of like underlying sort of like unresolved, you know, issues and childhood trauma and stuff. Basically a lot of the like therapy that I never, uh, that I had never really addressed. Um, but, uh, so yeah, so that was like 2 months there. Call it December, January— December of '20, January '21. Then I'm like living in this house, um, down there in South Florida with a bunch of other people that just came out of like similar treatment programs. And, and now I'm like full time. I like get a coworking space in Delray and I'm sort of just like in this really like safe space housing and then just like working and at this coworking space that I got an office at. And yeah, so now I'm in like my mind is sharp. Like I'm like, holy shit, I've like reemerged. And so this is like kind of a crazy thing is that Right after I went through that, one of our biggest competitors hits up one of our investors and is like, hey, we want to like acquire PhoneWagon. My investor calls me and he's like, hey, like you probably don't even want to entertain this, but like I got a call and, you know, they want to chat about maybe an acquisition. And he's like, you probably don't want to talk to them. And I was like, fuck that. Like, I definitely want to talk to them, you know?

Perfect time.

Just because like a few things were happening. Like again, our growth had— growth had, you know, my thought process was this is like, you know, our growth had started to slow down, right? If your growth slows down, then your valuation goes down because a lot of valuation in early stage companies is on a revenue multiple and it's based on growth rate. So I was like, if our growth slows down too much, you know, our valuation is just going to continue going down. I was like, it's actually a perfect fit. They're a great organization. You know, there's a lot of like— so I was like, I'm definitely— and then I also wanted to just sort of like sniff the market a little bit, be like, okay, I'm definitely interested in having that conversation.

And this is CalRail.

Yeah, this is CalRail. I'm like, definitely interested in having that conversation. Let me just like see sort of what they're thinking, you know. So ended up, you know, talking with their CEO and it was like a really good conversation. It was kind of weird because it's like, you know, you're competitive in the market, like product-wise, but it's like you're also human beings. So it's like they're like good people and like, you know, they're from Atlanta. I went to school in Clemson. It's kind of like the South, Southeast. And I was like, you know, like their people seem to love working there. And that was like really important to me. So, you know, as I'm evaluating, potentially even considering it, I was like, what matters? Like customers matter the most, then our people, then maybe product, and then me, you know, sort of like I'm last on the list. But, you know, I wanted to make sure that, you know, the deal was going to like make sense for the, you know, people in that order. So yeah, we started talking and then within like 2 weeks got a letter of intent for an offer. And, and then so then it's like once that happened, you sort of like high-level agree to terms. Then it's like lawyers, just like lawyer, you know, they do all the lawyers be lawyers. Lawyers be lawyers. Yeah. So then there's just like a lot of lawyers on it and you're, you know, there's like reps and warranties and like different, like different, like terms besides just everyone talks about like the number, but then there's like like all these different— it's what's escrow period, what's escrow amount, you know, is like there's just like tons of, you know, what's going to happen, what's transition look like, tons of different terms. So it's like then you're kind of like not even really negotiating, but you're sort of just like papering a lot of those terms like into the contract. So ended up getting the LOI and sort of agreeing to terms in February and then deal closed May 5th. So it was pretty quick. Yeah, it's pretty quick.

Was that okay? Like in terms of your mindset, were you, it was, it, you were just ready to go. So it was easy or was it difficult to go through that process? I mean, we've heard from different people, different entrepreneurs that exiting is a huge headache and somewhat bothersome to a lot of people and very stressful. How did you, how are you dealing with this off of this, you know, this journey that you just went through in your life a year before? How did that affect you?

So, well, I mean, look, negotiating the deal, I thought was stressful. There's a lot of like little things that sort of needed to be like tied up and there's like all these like things that you're kind of worried about. It's like, oh my God, are we going to be able to get over that or is this going to kill the deal? So like the whole time I was, I was stressed, but I was able to manage it because I'd just gone through that program, right? If I hadn't gone through that, like there's zero chance I would have been able to manage that process. You know, that's where I'm like, I don't know, I— some universe, something was like looking out for me where it's like I was like in the best headspace of my life at the time and I was able to sort of like navigate a lot of, a lot of like issues that were, that would, that came up. So I was able to navigate it. However, it was stressful. To your question, I guess, of I thought, I thought, look, I think I think I was mentally ready to, to, to do something else. You know, I was kind of like just going through that treatment program. I'm like getting my shit together. I'm like, this is like I need almost like I'm ready for like a new start, you know, the product also like we were in a really competitive industry, like, and there's a lot of like cost of goods sold that go with telephony, right? Because it's not just pure software. There's like, for instance, we initially were built on top of Twilio but ended up building our own like telephony and SIP stack, which is what it's called. But So like anytime there's calls and texts, you have to pay for the numbers and the minutes and like all these different— there's different legs, right? With like all the, you know, outbound, inbound and stuff like that. So there's a lot of like costs. So anyway, it's like a really competitive, arguably getting commoditized type market. And then there's a lot, you know, the cost of goods sold is like pretty material compared to a pure software play where you can get like 80, 90% margins. This was like we're struggling for 60% margins.

Yeah.

So like like, I just think like spacing, the space, the time, all of that. I'm like, you know, is this what I want to do for the next 5, 10 years? And that's when I'm like, now at the time, like 32. So I'm like, am I going to be 40, like pedaling, like cold tracking software, you know? So I think I was, I was mentally ready. That's where I think I was like very fine moving on.

Okay.

That's awesome.

I want to go back just back into that because I read in the show notes that one of you had a pretty big pitfall during the, during the Phone Wagon days with Salesforce that you had, you had hired, you tried to get some like rough around the edges sales guys. Oh yeah.

Yeah.

Can we talk about that story for a second?

So there's actually maybe a couple stories. Uh, once—

call centers require that you do dip. It's either you're going for like young college kids that know nothing or you have to sometimes go into like rough around the edges.

So, so I had this idea that I was like, we should open a sales office in Miami. I think partially I just wanted to move to Miami for the wintertime. So like in, you know, winter of 2019, I opened this sales office there. I'm like, all right, I'm gonna like hire— the profile of the person is like, I want these like South Florida guys that are like hustlers. Maybe they sold timeshares in the past, you know, and like they can get on the phones and sell this. So we would, uh, hired, you know, 4 to 5 people at a time. We would do the, the playbook that I learned at Yext, right? We could hire, you know, do classes, do like kind of training, get them on the phones, who, who would last. So hired this, uh, this class of like 4 or 5 sales reps. Um, and when you get hired, like, you don't get your first paycheck until like 2 to 3 weeks after, right? Because it's like your start date, then here's the payday, and then usually even from payday you don't get it. But I'm like cognizant, like, I didn't come from money or anything. I know that people kind of are like paycheck to paycheck. So instead of doing that, I like wrote these guys physical checks for, you know, their first week or two. I was like, here's your check for the week. Like, I'm not you know, you're not going to have to wait this like 3-week gap. So, so I guess one of them saw and like we kind of were in like an open office space, like a lot of startups are with like little kind of quasi cubes. So I guess one of them saw that I had the checkbook like on my desk that I wrote them the checks for. And, you know, I'm in and out, like I go to the bathroom sometimes, I eat sometimes. I'm not always at my desk. So I guess what happened was he grabbed the checkbook book when I was gone one time, and then he starts writing himself checks in like smaller amounts, but like still like a couple hundred dollars at a time, $500. So I start— so I check the bank account, and we're a startup, and you know on your bank account, your bank statement, you sort of see like it says check and check number, and you can click it and see the picture. Like it's kind of like a unique like line item like in the bank statement, like when you log in. So I started seeing these checks like later, and I'm like, that's weird. And I would look at it, be like, what? Be like, what the fuck? And then it's always to this one guy. And then I was like, that's crazy. So like, had to call him, be like, dude, what the fuck? Like, you literally stole the checkbook, you're writing yourself checks. Like, you're absolutely fired. Like, this is the craziest thing ever. And, uh, had to like close the bank account. It was like so annoying, you know? Like, besides feeling betrayed, which I did, right? And it's like, I was already like dealing with these issues. I'm like, trust issues too. It's like, layer that on. And it's like, I'm like betrayed. And it's like, you know, in my head I'm like, man, I feel like I did you a favor. I literally like wrote you a check so that you didn't have to go 3 weeks without having the money. And then like now you're going to take the checkbook and like kind of like fuck me over and like steal from me? You know, so I was like, like what? Like that's just crazy.

Yeah, character. It's Miami, by the way.

I don't know if it's not just, it's not just Miami.

We have, we've been in, no, but Miami is a wild place with a lot of people that are really interesting. Nobody's from Miami. You ever noticed that? Nobody's from Miami. They come and they go, they disappear.

We've had a lot of people reach into our piggy bank in different ways over the years as well.

So you can help people's character and integrity is a hard thing to come by.

Yeah. So usually you're the one that gets deep into the wire hit moment. So let's, let's dig into that.

Yeah.

So for Phone Wagon, you get acquired Did, did I'm assuming there was a, the wire hit and that's it. Did you have an earnout? Did you have to stay with the company or what was that moment like?

So wire hit, it was awesome. When the wire hit, I, I'm literally like living in this sober house with these guys and like we, there's like curfew and stuff. So I'm like, yeah, you guys want to go get a steak dinner? So like that was what I did. I like took the guys in the house out and we got a steak dinner. It was like, it was, it's like funny looking back how like anticlimactic the celebration was in terms of like what we did.

But one of our guests calls that the entrepreneur's epilogue. It's what happens after the wire hits.

He sold the company for like 9 figures and he called his wife and he was like, deal's done, wire hit. And she was like, okay, you grab pizza, I'll grab the kids from soccer. Yeah, it's just like, it like just sort of like anticlimactic.

Yeah.

Yeah.

It's like there's no, You expect like some party.

Yeah. So we had a pretty big, we had a pretty big escrow in terms of percentage of the deal. I think it was like, I think it was like, so I think standard escrow is like 10%. I think ours was like 20% and standard escrow time is like 12 months and ours was 18 months and we negotiated on that a bunch. But that's what it ended up landing on. So when Wirehit, you know, got most of the money and then the rest came after the escrow period.

Okay.

Yeah. So that was like 18 months later. So, but yeah. And so there was, there was a—

audience, tell them why things get held in escrow.

Things get held in escrow because, you know, for instance, people could, for instance, you could have lied about something that happened in the business, right? Your number, you know, your customers could be fake. I don't know if you guys saw that girl that sold her company to JPMorgan and she had like all these fake customers.

Yeah. And it's like, wasn't it like 2 years ago?

Maybe 2 years ago, but maybe the trial's happening now. Yeah, it's kind of like reemerged. She sold it for like $175 million and she said, oh, we have 4 million customers. And it was like they bought an email list of 4 million emails. So like that happened.

They not catch that on DD. That's all right, dude.

That's what, that's what people are, that's what people are saying. But anyway, so that's like on the extreme side. There's also things that could happen that you sort of try to paper into like the reps and warranties. But anyway, you put money in escrow in case there's like things that come up, maybe you know, an employee says, hey, you owe me 5 months of payroll that you never paid and you didn't disclose that or something. Or maybe you didn't even know that, right? There's just things that could come up. So they hold a significant piece in escrow in case there's like, you know, things that need to happen to the deal that, you know, maybe weren't discussed. So yeah, so that's why there's an escrow. Yeah.

Got it.

No, thank you for that. I think it's important for people to know. I think everybody just thinks you get this big check and it's like the deal's over and there's nothing else to do.

But yeah.

So did you stay on after that?

So there was a transition period. So my, my CTO stayed on for 6 months, obviously, to like move the tech and customers over as we, as we merged it. I was on for probably 3 months, so I, so I didn't have to stay on. I was on as a contractor just for transition stuff. There's a lot of things you need to like transition. For instance, like the Stripe account, it's like in our company name and like I have to approve it because like I'm the person on there. So like like there's a lot of this like accounts, like the bank account, like there's like all these like different things, um, that, that happened. So I was on just for transition purposes, not sort of like full-time.

I call it administrative breadcrumbs. It's like all these little things that you didn't realize, like the two-factor authentication that's connected to your phone.

Yeah, this thing, you can't log into like this vendor right here.

Yeah, yeah, exactly.

Totally. So, so now this happens, you go through this transition period, and you're kind of winding down, and then you sail off into the sunset and the now CallRail has acquired this thing and PhoneWagon is in your rearview mirror. And I always say the windshield in the car is the big one for a reason because you should be looking forward, not back. Right. So what's after that?

Yeah. So now, you know, so after that happened, I'm trying to figure out what I want to do next. And same thing that happened after I'm helpdesk. I want to stay in, you know, B2B SaaS and SMB if possible. but I want to, you know, do something that's really big right now. I've made like a few million, which is like good, but it's not great, you know, it's like, all right, I've hit like a single or a couple singles, maybe, maybe like a little double. But I'm like, I need to, I need to do something big, big, you know, I was like, this is kind of like, I listened to My First Million podcast. I was like, this is kind of small boy shit. They talk about that.

Yeah.

So I was like, all right.

I just got invited to Hampton.

Oh, sick. That's awesome. Yeah, so, so I basically, I have like this pretty much like holding company. So I call it kind of like a little like, a little like incubator myself where I'll basically, I'll just like play with different ideas inside of like this entity. Cause like if you have an idea and you spin it up too soon and it's like, do we create a company out of it and then like wind it down if it doesn't work? So I do a lot of stuff out of this entity that I have called Cameo Ventures.

So it's a venture studio basically.

It's sort of like a venture. It's basically a venture studio that's like just me, really.

So it's your fantasy factory.

Exactly. Exactly. It's like Rob Diedrich's Fantasy Factory, but one person. And I like, I'll make startup investments and stuff like out of it. But so anyway, so I'm like looking at different ideas, you know, one was like, can I create an escrow loan marketplace? So there's all this money tied up in escrow. Can you do loans against escrow? It's like, you know, so I'll kind of go down a path, that path for a little bit.

It.

You know, I looked at doing, you know, there's like cell towers were really hot, like rooftop cell towers. So it kind of looked at like all these different ideas and didn't kind of go forward with any of them until rather recently and started this new company called Sharewillow, which is profit sharing software. So instead of, you know, raising venture, there's a lot of companies that do profit sharing and they're profitable, whether they have employee profit sharing and bonuses or they do like distributions to owners and stuff like that. So a lot of companies, you know, instead of just, you know, creating a profit sharing plan with like their lawyer creates the plan and then manages it in Excel and does distributions manually, you're able to do everything inside of like a software tool.

So that's like the Carta for—

Exactly. I used to have that in our deck. I was like, yeah, I was like, Carta is for stock options and cap table management. And this is for all the companies that don't issue stock options, but they still need to motivate and reward employees. How do you do that? Profit sharing, right?

So, and you're funding this on your own, on your own dollar?

Initially I was. We just raised a little bit of capital.

Okay.

Seed or like pre-seed, basically.

And how was that? Was it easy for you?

It was. Yeah. So that was like inbound. I wasn't even, I wasn't even trying to raise. I had a couple of calls and they're like, yo, let me put in $100,000, let me put in $100,000. And I was like, okay.

Is it because people just know that you have track record now?

I think track record. Yeah. So I think a lot of times, like, as you guys know, you know, you're betting on the person. I think like the idea, I think it's a good idea.

Or jockeys.

We ask the question all the time, horse or jockey?

Yeah. Yeah. So it's like you're betting on the person, you know, I think so. Yeah, I think that's why.

So you're a jockey versus a jockey.

So do you— you don't think anybody cares about the fact that you went into a rehab? Are you worried that that could happen again?

I don't think so, because you're very transparent about it. I'm really transparent about it.

I think, I actually think I say fuck people if they have a problem with it. Yeah.

Yeah. I mean, obviously.

No.

Yeah, but obviously that. But I also think people like, I'm so transparent, not just about that, but I'm transparent pretty much about everything. And I think like when you have someone that's like arguably overshares and is like really transparent, like you're at least able to trust them. Like there's a trust factor, right? I feel like when people are too like vague and like kind of keep you at a distance. It's like, it's like, is that person like a real person or not? You know, it's like you can't—

like, he literally said this to me last night at dinner because he's like, you need to start putting more shit out there. And I was like, he's so afraid to show the real him.

He is the funniest, most charismatic guy you've ever met, but he's so smart he only shows this robotic, intelligent— yeah, highly intelligent guy. But if you're his friend, you get drunk with him, or maybe Too many edibles.

Yeah, yeah, yeah.

He like freestyle raps for 20 minutes. He could look at a Netflix title and like just how you could have a ton of fun with him. And I'm like, you gotta let people into the 100% who you, and that's the authentic you I think is gonna come out. So, which I see through you. And by the way, that wasn't a challenge. It was just like, I think that we live in a world that judges people really quickly now, right? That you're guilty before you're guilty and all this stuff. And I see all this character coming out of you and all this passion and charisma and the social thing that you said. And I can also see when you dive into a book the way you describe it, like it's very, it's no question that everything you're saying is true. Like I can feel it in the conversation. And I just wondered if that was ever a worry for you that you put that out there in the public.

So I think initially, you know, I was a bit like, even when I talked to, you know, your guy booking this, I was like, I don't know, I'm a little like more skeptical, but then I've kind of flipped. And again, I think I think the power of vulnerability, like, you know, is, uh, is really magical. I think, you know, being transparent, like, letting people know that, like, this isn't this, like, perfect thing that's gonna happen. But, you know, to maybe what we talked about earlier, like, a lot of entrepreneurs, like, it's almost, uh, irrational to create something out of nothing and think you're gonna succeed when the odds are saying 90% of startups are gonna fail. And you're going to do that, like you're already irrational, you know, coming out of the gate. So there's already a lot of like, you know, mental health things that you have to have that maybe like most of the people, most people don't have, whether that's like, you know, you, you know, a little bit of a sociopath or not sociopath, but you're a little like self-consumed and it's like, I'm going to win when like everyone else can't win. But like you have to sort of like have that internal belief. But yeah, I think, I think there's a lot of like mental health issues that are I think entrepreneurship is a mental illness. Yeah, it is. It's also an addiction in itself, right? It's like you're addicted to the game. You're addicted to like figuring it out, getting that first customer, like that high from the customer. Like I was in this old startup office the other day and I saw like the bell and I was like, man, imagine when you make that sale, you make the walk up to the bell, you ring the bell. Everyone's like, hell yeah, you made the sale. Even if it's like a $50 sale, I was like, that's even cooler. Than like the wire hitting because like, I don't know, there's like these like dope shared experiences.

Yeah. Yeah.

And shared and shared experiences. But like just the little like dopamine hits that you're getting throughout, you know, the journey of entrepreneurship, you make that hire, right? You close that deal. Like this happens, this happens. Like all these little things are just like, boop, boop, boop, boop.

I like to be right.

Like yesterday I was talking to this guy that I'm working with in another business and we got stuck in a negotiation and he was like, I think that's it. And I was like, no, that's not it. We're going to keep pushing. And then that push turned into— and I was able to unlock something. And then an hour later I got a phone call that was pretty detrimental to the stage we were at. And they were like, oh, this is missing. And the vote is next week on Thursday. And I called somebody and they're like, it's going to cost $10,000 to get it done in a week because they were taking advantage of my my weakness. So I went back to the guy that said I needed it and I was like, this is your fault. I was like, you gotta do something. And he was like, listen, I'll make a deal with you. And he cut me a deal. So now I don't have to spend $10,000. And I went back to this guy and I'm like, I got it done. He's like, you always get it done. And I love that feeling of being the guy that always gets it done. Like I love that little confidence of just like that ringing the bell. Sometimes it's not even a bell. Sometimes it's not even a sale. Sometimes it's just a win. It's a W in the column of entrepreneurship where it's like, you know, anything.

Well, just bending reality, right?

Yeah, exactly.

It's like, this is what, like, this is what conventional wisdom says, this is what's supposed to happen. And then when something, when you feel like you could have some influence on bending that reality or bending that light, like, that's where I think it's, that's the, for me, that's the drug of entrepreneurship.

We bought this building for a dollar, the one that you're sitting in. That's a whole property, 9.5 acres.

That's crazy. Yeah.

And everybody was like, what? You're gonna, you're gonna, you're gonna, even the people that were, that we, we bid for against it, they said, could you raise the bid? Because the highest bid is much higher than you. It turned out to be $3.1 million against us. And we held that $1 and won.

What? Yeah.

I think that that's the power of storytelling, right? Like that's the one thing I feel like, because they wanted your use case. Because they liked our story.

Yeah.

Yeah. Branding a story is selling.

Right.

It's biz dev. It's exactly what you and I sort of lit up about. And it's like, there's like, there's something to it. It's like, it may not be for a sale where there's monetary value, but business development is about sort of a ladder or an escalator to a process of a process that leads to something. And I don't know, it's just something that I just love the game, man.

So I'm curious. Yeah, no, amen to that. I think just, just keeping an eye on the clock. So, cause we know we're taking a lot of your time and we really appreciate it. I love this combo. So you used to do a lot of vlogging. You were, you were sort of early in the content game. Have you stuck with it?

No, I'm an idiot. I should have stuck with it. If I had stuck with it, I would probably like be in the stratosphere right now.

And that's—

I'm glad you didn't because you probably wouldn't be here in the show. Like, because we didn't pay you to be on the show, right? So at this point, because you're super inspiring, man, I can see you being on a stage telling your story whether that story is building and exiting, whether that story is fuck around and find out, whether that story is the challenges you faced with your own health and addiction. Like, I feel like each of those individually is powerful. When you combine them together, I mean, it's like, you know, it's like a Korean barbecue taco. It's amazing, right? Yeah. So I just feel like that's the— there's just something dope about that. Like, and I can see you being super inspired. So are you all in right now on Sharewillow or is this sort of all in on that?

All in. All in. And that's, you know, one thing that I'm getting back to finally now is the content game. And that I'm really excited about. And again, like, I've really— that's, that's like my one regret right now. I'm like, because I know how these things, first of all, take time and also compound. So I'm like, man, if I had just kept with it. That's like one regret that I have right now. But, you know, the one, the one thing that is like a little bit of a saving grace is that, you know, if you believe in like the 10,000 hours, I was like, okay, well, I've already logged some hours towards like, you know, being an expert at this. So at least, you know, I'm not starting from zero. I'm able to like kind of log back on to, you know, whatever hours I've accumulated. And, you know, there's learnings that have happened. But, but yeah, I want to— I'd like being in front of a camera. I want to continue being—

I think you belong in front of a camera. So, so I'm big on reciprocity. I feel like to ask you to come in, spend time with us, whatever, you know, that's, that's a take, right? So one thing is you strike me as someone who likes some fun tools and systems. So let's connect offline. I've been— I sort of put my, my tech brain to like the AI shit.

It.

There's a bunch of tools and things I've been messing around with that have saved me like a lot of time. So like if you want to hit me up offline, like I can send you a bunch of stuff. So save yourself 50, 100 hours on, on some of those things. I've given him some tools, he's been using them. Um, I just think that we're starting to put an eye more towards content now outside of this. And if that's—

I was literally looking at your cameras and I was like, I want— because I'm looking like I want to set up this like in— I want to make my apartment just like a studio, like a Star Factory. So I was like looking at your camera, like I need some DSLRs. I was looking at the mics, the Shure mics.

So what I would actually recommend you go with is the list setups and we'll— again, we'll give you a punch list of everything. But like, it's— I think the tech and the tools, because like for you, you strike me as a guy that would be rocking long form and then taking those long form and then turn it into shorts.

Yeah, yeah.

There's a lot of stuff now. So we'll connect offline on that.

So cool.

So what stage are you at with Share Willow?

So MVP should be launched in 2 to 3 weeks from now. So by the time this comes out, it might even be launched. So yeah, so have this awesome like B2B designer that we have everything in kind of like clickable prototype on Figma. Nice. I have I have these two software engineers that are building it right now and it's almost ready for like MVP to be launched. Website's up, I'm getting customer feedback, I'm talking with customers. Again, pitch deck is there. I'm like loosely, I'm loosely like raising.

What's your ICP for that?

So there's three different customers. So SMB, so imagine like basically like I just saw this, there's a moving company in Washington, D.C. called JK Moving and Storage. They just announced, hey, we just did an annual profit share of like like $2, $2.5 million to date since, since the, uh, since inception of our profit sharing program, they've given $30 million to their employees, right? So a profitable company that's, you know, giving back to their employees that wants to, you know, make their behavior change, right? Think like an owner, that sort of thing.

So basically you're gonna— so basically you're gonna scrape job boards, look for the language around that, and then use AI to build a lead list.

So I've done that. So I literally— there's like 100,000 jobs right now on Indeed that have profit sharing as a benefit.

Yeah.

So I've actually created—

as your lead list?

Yeah, yeah, yeah, yeah. Uh, so second, second type is there's like these micro PE funds that are going after boring businesses, Main Street cash flowing businesses. If you follow—

he's just been talking about— if you follow like one of us, man, it's awesome.

Follow like the Cody Sanchez of the world. Yeah, like all of that, right? So like these micro PE funds, they'll have like 5 to 20 investors. They'll go in, they'll buy, you know, a laundromat, a car wash, whatever. There's also like Enduring Ventures and, you know, like all these different— so it's the micro PEs, the profitable SMBs. That's who we're focusing on, you know, initially. Maybe eventually down the line that I'm like taking a look at but not kind of going after. There's large enterprises, Delta, Southwest Airlines, they have profit sharing into a 401(k) as a benefit. We're not going there yet. We're staying like kind of downstream at first, but right now I see—

no, it's awesome.

Price point, what's going to be?

I don't know yet. I got to test it.

Okay.

What do you think?

I want it to be a lot.

You don't want to—

you know, I want it to be a lot. You want it to be? Yeah, I think it's a lot of value. The hardest, like $4,000 a year. Yeah. Plus then you, you know, pay for the 409A A or no, you get the 409A, whatever it is.

I would like to keep us posted because obviously I would be happy to.

I would like like a $5K ACV, like annual. Yeah, something like that. But I'm not sure. Yeah, I got to test it.

That's awesome. Love it. And then just curious in terms of like I always like to use the light bulb as an example is, you know, how many failed experiments led to the light bulb, right? How many failed ideas or ideas did you test before you got to Surewell?

So, I mean, I have a lot of ideas, but I actually went down like a serious path of like creating documentation and like really looking into like maybe, maybe like 5, like 4 to 5 ideas where like, I'm like, I think I'm going to go after this. And then I'm like, ah, like, you know, for one reason or another.

Yeah.

Dope. Do you have a system that you've created for how you generate, capture, validate or invalidate ideas? Like, is that like formalized or is it all in your head?

It's pretty formalized at this point. Yes. There's a lot of documentation that I basically like sort of go go down that same path every single idea.

Can you give us that, like, a high-level principles level for the audience?

High-level principles is initially I'll write out a use case. I'll like free text, like, the actual use case. Then I'll look at, um, you know, products that are in the market. I'll look at, you know, market size of those products, you know. Then I'll kind of like do an analysis, you know, of those products. Then I'll start to make like, all right, like, what features is this? And then I'll just start talking to customers. So, and all of that is like well documented.

And like an Notion or something like that, or I just use Google Docs.

So I'll just use Google Docs and I'll create, you know, customer use case, customer, you know, feature doc. And then I'll just do kind of like overview and look at, look at the different ideas that way.

And then you go from there to like a PRD, like Amazon style.

Yeah, exactly. Right on.

So PRD folks, product requirements document. It's basically like, who's the user? What are we doing? What are we accomplishing? So that's awesome. Thanks for sharing that. Appreciate that. It's What I love is as, as vast and wild as your creativity is, it seems that you've found a lot of structure in some of the things that you've gone through. And it's that structure now that seems like it's unlocking more creativity. And I feel like I wanted to share that with our audience because I feel like as, as these sort of ADHD tendencies that many of us entrepreneurs have, we sort of loathe structure in some cases. We sort of don't wanna be put in that proverbial box. But really what, what I hear and feel in studying this and now I've had so many guests on our show is it's really that structure. It's really those systems and those principles that create the freedom for you to have some of these wire hit moments and now discovering Sherwillow. So would you say that you agree with that?

100%. I've been saying that a lot recently. I'm like, let me put the guardrails up and then let me like bounce around between the guardrails, but I need the guardrails to be up.

I love it.

The last question for me, I'm very, I like to be very clear on where I'm going You mentioned that you made a few million and you mentioned the story about the podcast where they talk about being a small boy or whatever it was. When you look forward at Sharewillow and/or your future, what do you think that next milestone is going to be? They say a lot of advisors that I talk to say you need it. You have to have a number in mind. Like, what does that look like for you?

I want to build in, but, and I actually have it written on my mirror, like I, Ryan Shank, will become a billionaire. I'm working with this life coach right now. And I said like, this is what I want to do. He's like, why do you want to do that? You know, all this stuff. And I was like, look, that's just like scoreboard numbers. If I like, you know, exceeded, that'd be great. If there's like a little short, that'd be great. But it also sort of just makes you think big. You know, it's like these little optimizations in the business are great, right? But it's like I want to just like be thinking big with everything that I'm doing.

So I have to ask a follow-up to that before we let you go. Go, which is clearly you've developed some tools, and those tools have helped you maintain what seems like pretty good sense of mental health, if I'm, if I'm feeling you and hearing you correctly. That's fair.

Yeah, yeah, yeah.

So for the audience, what are some of those— what, like, what are some of your practices or tools that you will do now until forever that help you maintain the same kind of sense of poise that you've clearly developed.

Yeah, so I have 4 non-negotiables that I actually have written on my whiteboard. A lot of this stuff I have to like kind of like visualize or else like, again, if you're like ADHD, you'll just like forget about them, you know? And I'm also operating, I think, with a lot more intent these days. So there's a lot of like intention behind everything. But the non-negotiables is bed by midnight. I would like to push that up, but like I want to be able to like check it off every single day. Bed by midnight, morning cardio, a workout in addition to the morning cardio and do something intellectually stimulating. So like learning every single day. So like those are like 4 non-negotiables and it's like if I can hit them, that's sort of foundation for everything else. Like, like even if I just get good sleep, that's 90%, like 70% of it. Awesome, right? So those are the daily non-negotiables.

Thanks so much for sharing that and thanks so much for coming on. For Obsessed was a great episode and so thanks always for everybody for tuning in.

Thank you for listening to Ford Obsessed. Please share this episode, subscribe, and leave a review on your podcast app. This episode was hosted by Pete Senna and David Salinas from the Digital Surgeons podcast studio in New Haven, Connecticut. Special thanks to our AV crew, Steve Walter and Meg Olson.

Ford Obsessed is produced by Robert Roach.

If you'd like to contact our team, visit us at fordobsessed.com.