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#45: Startup, pivot, and building the bridge with Greg Coleman

Spoke with Greg Coleman, co-founder and CEO of Sworkit, about the startup journey, identifying common sense pivots, and his specific rejection of the “all-in” concept. I appreciated his incredibly honest and open sharing of his perspective.

December 2, 2020 • 42:18

SPEAKERS
Aaron Spatz, Host, America’s Entrepreneur
Greg Coleman, Co-Founder and CEO, Sworkit

Aaron  00:05
I’m Aaron Spatz and this is The Veterans Business Podcast. A podcast centered around the stories of US military veterans and their adventures in the business world following their time in service, its stories of challenges and obstacles, and an inside look at how veterans find their life’s work, their purpose in their post-military lives.

Welcome to another edition of The Veterans Business Podcast. I’m Aaron Spatz. Thank you so much for tuning in. I’d love to hear from you. If you have any feedback for the show, feel free to drop me a line at podcast@boldmedia.us. Just really, the heart of the podcasts, the heart of all this is sharing stories that are going to be helpful to you, encouraging, inspiring, and helping you get kind of a behind-the-scenes look at the way other veterans in business have been able to go through their careers. So this week, Greg Coleman joins the show. Greg is a graduate of the US Air Force academy, went on to a 20-year career in the Air Force, retiring as a colonel. He’s an MBA graduate of Wharton and he’s had a very varied career since retiring from the Air Force. We’ll dig all into that here in just a few minutes. He’s a co-founder and CEO of Sworkit, a digital wellness and fitness company. Greg, I just want to thank you so much, sir, for joining the show.

Greg  01:26
Well, thank you for having me, Aaron. I appreciate it.

Aaron  01:28
Yeah. Just real quick, let’s just go ahead and dive in. So what compelled you to join the Air Force? What was your upbringing like? Take us a little bit on that journey with you.

Greg  01:41
Yeah, sure thing. So, yeah, so I’ll kind of go back to the “hey, it all started when” conversation. So I grew up on the south side of Chicago. I’m a kid of the 70s and 80s, grew up in that time. I grew up with the military as kind of part of our lives. So my parents were divorced, but my father was a graduate of the Naval Academy. And then he went on to serve as a helicopter pilot on active duty. He was on active duty in the years immediately after Vietnam. And so I was kind of had been exposed to the idea of a service academy, the idea of serving, the idea of the military. And coincidentally, my grandfather on my mother’s side, so my mother’s father, was a retired Army colonel and he was a Tuskegee Airman. So he was one of the first black pilots back during World War II.

So on both sides of my family, we had this service aspect – one side, Army, the other side, Navy, both of them aviators. And it was just one of those things where I kind of grew up kind of around flying. My mother was a flight attendant and had a private pilot’s license. And so, for me, very young I decided I wanted to be an Air Force pilot. My dad used to tease me. He wanted me to go to the Naval Academy and I was like, “Look, Dad, I’m not really a fan of water. So I think I’m going to go do the do the Air Force side and land on national runways instead of aircraft carriers.”

But that said, so when I graduated from high school, I went off to the Air Force Academy because I wanted to fly. And at the time, it was right after the Gulf War, the first Gulf War, and there was a big drawdown happening. And it got to a point where if you want it to fly, the best path was by going to one of the service academies because to pipeline for ROTC and OTS were shrinking up considerably. So if there was ever any doubt about whether or not I wanted to go to a regular school and maybe do like an ROTC scholarship or go to the academy, the timing really settled me in on heading down the Air Force path.

And so then, from a story standpoint, I went to the Air Force Academy, came out of there four years later with a degree in electrical engineering and then went off to a flight school at Vance Air Force Base as a newly commissioned a second lieutenant. Went through that program there over the year, had to make a decision. At one point I decided, I thought I wanted to go to be a fighter pilot and then I started thinking more about the lifestyle implications and what would actually be more fun to me long-term. And so I was one of the guys in my class who had the opportunity to pick one or the other.

So I was kind of like, okay, do I want to go do fighters and pull G’s all the time and basically deploy and be at home station or do I want to go the heavy route and really go see the world and just have the opportunity to really just kind of go all over the world and just see everything it has to offer. And I chose the heavy path. And went that way, flew on active duty for nine and a half years. I started out flying KC-10s then I flew Gulfstream Vs, which are the VIP airplanes. We call them C-37s in the military. Did that then I left active duty and went to the DC Air National Guard where I flew C-40s and C-38s then spent a little time as a Force Support Squadron commander and then some time at the headquarters and director of staff.

And just to actually even provide a little more context, I just retired at the beginning of the month. And so I was this hybrid, right? So I’ve got 25 years of the total service of which 20 were active. And so for the last seven years, I’ve been running the company full-time and then periodically going back on orders and I was able to put together a full 20-year active duty career within this 25-year of total service timeframe. So I’m now a part of the blue card club and still kind of – not that there was really an adjustment to make because I’ve been out of uniform on an everyday basis now for seven years, right? But it’s still now starting to hit me that, oh, you know that part of my life is actually over. And it’s been fun and it’s also been interesting to now kind of look at the world through a slightly different lens.

Aaron  06:05
Well, no, I mean, a fascinating, fascinating story and background. So I find it interesting that your entire family, just that entire background that you have is all aviation centered. And so it’s a very natural progression for you just going that route. And so, I mean, shoot, you’ve almost got all the branches of the military covered then within your family.

Greg  06:33
Yeah, absolutely. And it was one of those things where, you know, there’s something about the Air Force that just really appealed to me. Again, even though I came of age during like the years of Top Gun, there’s still just the Air Force aspect of it was much more interesting to me. And it’s funny, there are also some interesting points of connection, family connection, as well too. Because my grandfather, after he spent part of his career in the active duty Army, he was a guardsman as well. So he was a member of the Illinois National Guard and he retired there as a colonel. And then, however many years later, I retired as a colonel out of the district of Columbia National Guard. And so there’s some really interesting parallels.

Aaron  07:11
Yeah, no, that’s crazy. Well, I mean, one, thank you for your long career. And two, I had no idea that that was that recent that you punched out. And I think it’s really cool, though, because it’s kind of given you an opportunity to kind of do this whole transition thing over the course of several years. So you can kind of get a feel for what civilian full-time life is like and then now it’s all gone.

Greg  07:40
Yeah. Well, I think that’s one of the beauties of the guard. I mean, it’s one of those things where had I known about the National Guard and really understood what you can do and what it was about, I probably would have made the transition much earlier. I may even have started out on that path.

Aaron  07:55
Wow.

Greg  07:55
But the thing that’s been amazing about the guard is my ability to, I mean, we have this thing where we talk about the citizen-soldier or the citizens of the Americans and it really is remarkable. It is a true statement, right? You can have a civilian career and civilian life and also have this military career and you can kind of flow in and out of each one. So while I was full-time guardsman, that’s when I went to the Wharton School and got my MBA. So I was a full-time student at Wharton and then also a full-time guardsman.

Aaron  08:26
How the heck did you pull that off? So, I mean, were you actually attending on campus or was it remote?

Greg  08:37
Yeah, yeah. So it was like one day, one hour at a time. I so I went to the executive program at Wharton. And the thing I really liked about that program is that it was a one for one matching. I went for one for one match with the full-time program. So a lot of the other schools, the executive program is a slightly different program than what we what call the on-campus Wharton students go through. And so for that program, it was in fact on-campus. It’s just instead of being in class from Monday through Thursday, we were there every other weekend. So we would show up and start classes at 9:30 in the morning on Friday, go to class until about 7:00 at night, get up the next morning, and then in class again from nine to four on Saturday, then go home and then come back two weeks later and do the same thing all over again.

Aaron  09:27
Wow.

Greg  09:27
And so when you do that, combined with a couple two weeks sprints and then not taking a summer off for an internship, we were still able to start to program. So we started in May where the Monday through Thursday group started in August, but we all graduated and walked a stage together two years later.

Aaron  09:47
Holy cow. That’s cool. Yeah. And that was actually one of my questions I have. I was curious about the whole Wharton experience. So was that when you’re on the – I think you’ve mentioned a second ago, but you had already transitioned to the guard at that point, right?

Greg  10:07
Yeah. At that point, I was full-time guard. I was a a pilot. I was still flying. I was flying C-38s and C-40s. I was actually a dual qualified pilot at the time. And I mean, it was busy. I mean, you were working a full-time job and going to school full-time. Oh, and also literally a week before my first microeconomics midterm, my first child was born. So my wife and I was just gluttons for punishment there. And my wife works as well, too. So, you know, it’s always been kind of busy and chaotic in the Coleman house.

But the thing I really liked about going through that program is that it allowed me to kind of re-cage my thoughts and my thinking about business, right? I had always had a desire and an interest in becoming an entrepreneur, right? I didn’t know when I was going to do it and I wasn’t sure what the path was going to be. In fact, I went to Wharton thinking I was going to maybe spend some time in finance first, maybe as an investment banker or maybe trying to get into private equity or venture capital. But while we were in our second year on our international trip, we’re sitting in Moscow, watching Lehman collapsed on the television and then thinking, okay, maybe a career in finance is not in the cards right now. And so that’s why I made a pivot and a guy I met there ended up becoming my business partner and that’s when we decided to start the business about a year after graduation.

But the thing that was really great about business school is, you know, going through the military, you don’t understand the leadership piece, right? You understand the team building piece, you understand the working with people piece, you understand the leading people, you understand the operational aspects of it. You understand even the project management aspects, like just actually getting things done and getting a mission done and just leading people in teams. But what that program did for me was really start to shore up the other things I would need to be an effective business leader, right? So understanding the accounting, understanding the marketing, understanding not just how to problem solve, but how to structure your problem solving and to take these big, ambiguous situations and try to make sense out of them in some sort of coherent manner.

So school did a lot of that, just helping me understand the finance. And so by the time I graduated, it was changing the way I was looking at business, changing the way I was looking at an entrepreneurship. And also, it kind of gave me another sort of – not another direction, but what it did was it changed the narrative when I was meeting and talking with people, right? So instead of when I was pitching venture capitalists on our business or pitching investors on our business, it wasn’t like, oh, hey, yeah, you’re the Air Force pilot trying to play entrepreneur now. The conversation is more like, okay, hey, you’re a Wharton MBA. So I’m not going to question your business quantifiers or whether or not you’re actually qualified to do what it is you’re talking about doing. So one, it shored up my knowledge, and then two, it really helped to kind of solidify how the world is calling me from the outside looking.

Aaron  13:27
Wow. No, I mean, that’s incredible insight. And I always kind of getting underneath the hood here on just a couple of these topics and I appreciate you sharing that. I think it definitely gave you a rare opportunity to – one, you’ll network with a lot of really great people, but two, you’re kind of in the middle of two worlds between military and business and so it gives you this opportunity to taste both kind of at the same time. So then you mentioned you met your business partner there about a year later after graduation then that’s when you all launched Sworkit. So take us through that journey. What was that like?

Greg  14:10
Yeah. So Sworkit is how we’re known, right? And that’s our lead product. That’s how the world sees us. The company behind us is called Nexercise, next generation exercise or nutrition plus exercise, right? While we were in school, what we found is that, hey, listen, we were full-time students, we had full-time jobs, we were husbands, and we were fathers of young children. And so as a result, it just became increasingly difficult to try to find time to just take care of ourselves, try to find time to work out, time to get to the gym. You’re in different places, you’re traveling, you’re studying. There are all kinds of demands on your time. And we just found that it was just becoming much more difficult for us to just take care of ourselves physically.

And the thought was, well, hey, listen, if we’re having this problem and we’re motivated, I mean, holy cow, what is it like just for everybody else? And then we thought, hey, listen, is there a way that maybe we can use technology to solve this problem? So we came up with this concept called – yeah, we call Nexercise. And we used our time at Wharton to actually work on and flesh out this business plan. So we actually worked on an early version of the company as a business school project that I think took us through three different classes. So it was cool just kind of getting ideas, getting perspectives from some of our classmates, getting their input. But when we graduated, it wasn’t quite ready for prime time. So we kind of put it on the shelf and kept moving.

But while we were there is when the very first iPhone was announced and launched. And then shortly after, that came the first Android phone. And I remember we were probably about six months after graduation, I was hanging out with my business partner, Ben, and he had a Motorola Droid that he was playing with. And he was looking and thinking about the accelerometers. He’s a tech guy by nature. And he’s like, “You know what? There might be some interesting things we can do with technology here.”

And then we were also looking at not just a tech in the iPhone, the motion tracking, but also seeing what was happening at the time with all of the gamification of everything and a lot of daily deals sites like your Living Socials and your Groupons and things like that. I said, “Huh. Is it possible to use this technology and game mechanics together to try to drive behavior to get people to exercise more consistently and log that exercise?” And so that was the original company and that our first product was called Nexercise.

So we had that. We were growing that business, doing well with that. But then what we started to realize is that people were looking for content as well. It was one thing just to kind of track at what people were doing, but a lot of people were wondering, hey, listen, I don’t know what to do. Hey, listen, I have these limitations or I have limits and whatever, my time and kind of my space. Maybe I have an injury. So what can I do that’s going to help me stay healthy?

So we started thinking about, okay, do we build this ourselves? Or do we maybe find something, maybe some diamond in the rough out in the market and bring that product, that team company, whoever on board, in our own company, and then build it from there, just take what’s already been created. And so long story short, we ended up connecting with coincidentally another veteran, Ryan Hanna, who’s now our VP of Product. And he had developed this this app called Sworkit, which he built it for himself to help him pass the Army fitness test. He was an Army reservist at the time. And so he’s done some really cool things. He’s getting some cool traction. So we said, “Hey, Ryan, listen, would you ever be interested in selling your company to us and then joining our team full-time?” And then Ryan says, “Okay. Well, make me an offer.” So we made him an offer and he said, “Okay, I’ll take that offer.” And so we ended up acquiring his company back in 2014.

We took the product as it was, completely deconstructed it, and then rebuilt using our design philosophy and put it back on the market as kind like a version of Sworkit that’s recognizable today. And then we just watched it just kind of take off, and to the point we’re like, huh, we’ve got this product out here just going up, where at the same time we’re grinding and pounding away on not quite as steep of a growth trajectory with the other app. You know what, this is the opportunity. Let’s actually focus all of our attention on Sworkit. And so over 2015, that’s when we executed a pivot to focus exclusively on Sworkit and we’ve been building it and growing it ever since.

Aaron  18:40
Wow. No, I’m like sitting here, just like tell me more, man. I love it. I love it. I love the story. No, that’s cool. So you covered a lot of things in short order so I’m trying to go back and unpack some of these things that you just talked about. So you were developing one idea, one concept at the beginning, and then you’re starting to kind of think about, well, what if we went this direction? You went and found someone who was doing it, and then you do an acquisition right off the bat and grabbed that company. You obviously made them a good offer because then he was like, yup. sounds good. And then you just continued to develop that, watched it launch, and then decide. I guess then that was kind of a big decision point for you guys was then there’s a point at which you determined, like you just said, do we just shut this one down and just go all-in on this one product? And it sounds like that’s kind of like there’s definitely some discussions that had to have happened.

Greg  19:41
Oh, absolutely. Yeah. I remember we were actually at a trade show in in San Francisco where we were really taking that Nexercise product and we’re looking at positioning it as like a corporate wellness tool, like a game mechanics, the gamification tool that could be used in companies. And I mean, we were getting some traction, but it wasn’t anything great. And when we had an impromptu board meeting – because our other board member happened to be in San Francisco that same week. And so we just ended up having an impromptu board meeting in a restaurant. And sitting there and that restaurant was where we made the decision to pivot the effort of the company. So it is kind of funny how these things happen and then that’s when we went all-in on that direction and started just jamming away.

Aaron  20:31
That’s cool. So then this may end up being the same answer, but what I’d love just to kind of get further understanding was, you know, what’s a major challenge that you guys have had overcome as a company? It could be recent. It could have been back early the day. And then the second part of that question then is going to be at what point do you feel like it took – how long did it take for the company to kind of get its feet under itself and start to really grow?

Greg  21:00
Well, it’s one of those things where I think there’s always a challenge, right? There’s always some mountain that you’re having to climb. And just the nature of the of the mountain changes from day to day, week to week, month to month. Not unlike if you’re doing an operation in the military, right? And I also would not say that there’s any necessarily one moment. A lot of entrepreneurs, you know, and maybe it makes for nice conversations, but they’re talking about, “Hey, listen, there was this magical moment.” I personally never experienced that magical moment nor do I know anyone who can share with me candidly what that magical moment was.

But there’s always challenges, right? So the challenge could be, hey, listen, how do I get the company property capitalized to do what we need to do and what we need to get done, right? That’s what we’ve been there, right? Another one we’ve been is, hey, we’ve got a lot of product bugs right now and we need the engineering team to really step up their game and to get it off so that we’re not messing up the consumer experience. So that’s another kind of challenge that they have to solve. Another one that could be, which kind of goes back to the pivot, is just like, all right, is the path we’re on the right path? And just to problem solving around that, just doing the analysis or trying to figure out what does that path look like, right?

And then on a smaller scale, there are other little points along the way. We used to have ads in the app, right? But then we made a decision, listen, we’re not a media company. Why are we serving up ads? We’re a fitness company. So let’s build a fitness solution and not try to optimize around eyeballs or ad impressions or ad clicks. And so there’s just a lot of little decisions that you kind of make along the way. Some decisions are more impactful than others one way or another, either in a positive or a negative manner. But it’s more of, hey, listen, what is the challenge of the day? What is the challenge at a month? What is the challenge of the moment, right? And then just kind of figuring out what that is. One, identifying it, naming it, and then figuring out strategy to tackle it.

Aaron  23:13
I love that. No, I appreciate your sharing that. And no, I think it’s funny because yeah, I’ve interviewed a number of people now. I’ve also had the privilege of consulting with a number of companies and I would have to agree with you. There’s been maybe a couple one-offs where I think people will point to maybe – it’s like it’s never what you think it is. It’s never this, hey, we had this major contract come through, and all of a sudden, we just went like this. And it seems more likely more often than not. And so it sounds like your experience is the same. It’s like there is some event or there some decision that was made and it kind of altered the course of the company. And you can always point back to maybe one of those decisions that kind of altered the way that things went after that point. But it wasn’t like this monumental get a phone call and get a $50 million contract just out of thin air.

Greg  24:13
Yeah, yeah, yeah, yeah, yeah. There’s a lot grinding that goes on for those little inflection points that you see, right? There’s a lot going on behind the scenes.

Aaron  24:19
For sure. And then, just real quick. So was the company – did you guys bootstrap it? Did you take capital? What did that look like for you?

Greg  24:32
Yeah, we’re taking some capital. So we went through the Techstars Accelerator with the previous product, right? So when we’re just Nexercise with a Nexercise product. So in 2013, we went through the Techstars Accelerator, which was an amazing experience. It was awesome for our company. If anybody was ever contemplating, that program has my highest endorsement. And coming out of the internet, we raised a little bit of cash going in just to kind of keep the lights on and maybe hire a couple of people.

Coming out of that, we ended up closing our seed round. So we did like our first million-dollar round back then. And then in 2015, when we decided to execute the pivot, we just raised like a little bit of follow on of another million dollars back in 2015, but we’ve been running a very cash efficient business since this. We’ve not had to raise any outside capital since 2015 and we’ve been able to grow organically. I mean, in fact, 97% of our growth to date has been organic.

Although now, we’re working on trying to figure out, okay, listen, what are going to be the key things that are going to help us be able to, really, again, how do we get to another inflection point where we can then start to accelerate it? And that may be capital, that may be organic. These are the types of things that we’re evaluating right now. It’s like, okay, listen, what do we need in order to take it to the next level? And can we do that with revenue or do we need to go get some outside funding in order to make that happen? So these are the types of things that we’re thinking about now, but we haven’t raised any outside money in about five years.

Aaron  26:00
Wow. That’s great. And then you’re just able to reinvest into the business and keep on trucking. So there’s a large percentage of this audience –  I mean, I guess it’s like saying there’s a large percentage of people, but it’s all people, right? It’s kind of obvious. It’s like who here lives somewhere? It’s like, okay. So part of our audience is people that are just in their professional journey. They’re either kind of stewing on different business ideas, kind of thinking about jumping out and going and doing something, whether it’s on the side or whether it’s just all-in. And then there’s people that are in the journey right now trying to develop something and trying to get it going. So knowing that context, what are some misconceptions or what are some things that you’ve kind of discovered along your own journey that you’re like, man, they don’t tell you about this?

Greg  27:07
Yeah. I think even beyond, they don’t say – well, here’s the thing they don’t tell you. Some people actually do. I tell you out of everything I’ve ever done, building a business has been the hardest thing I’ve ever done, right? Not the Air Force Academy, not flight school, not SERE, none of that. Building a business – not even war, right? Building a business has been the single most thing I’ve done in my life to date. So that will probably be the biggest thing. That said, it is still worth the journey, right? But you need to be very clear on what it is you’re getting into and what it is that you’re undertaking.

So there are some things that you will hear and you will hear a lot of people kind of like state as a truth that I don’t necessarily believe to be true. You mentioned that a lot of your people – so many people are doing it full-time, some people are doing it part-time. There’s a certain percentage of investors and successful entrepreneurs that take the stance of, well, you know what, you need to go a hundred percent all-in. You need to quit your day job. You need a mortgage your house and you need to do all that and do whatever it takes to go build this business, right?

I actually reject that singular thinking. I think it’s very situation specific and there are these things called responsibilities that people have, right? And that may work for a 22-year-old recent college graduate. But if you’re in your 30s, 40s, 50s, and you’ve got a family, a mortgage, tuition, bills, things like that, the idea of just burning the boats and quitting your job and just betting it all that you’re going to be able to figure it out six months may not be the best way to do it. I mean, you can start out building a business part-time.

I think probably the biggest way I heard described to me a long time ago that really resonates with me is this concept of, okay, you’re sitting on the shore as an entrepreneur and then there’s this island, right? So there’s this island here, which is – I’m sorry, you’re saying the shore as an aspiring entrepreneur and then there’s an island here, which is kind of like you’re full-time in the job, right? And there’s this body of water in between. So you got to figure out how to get from here to here. Well, you got to build a bridge, right?

And so my philosophy is, okay, listen, while you’re still have revenue, still have income, still have money coming in, work on a business. You’re going to have to make some sacrifices and probably give up everything else outside of earning money to figure out how do I build this bridge across, right? So you got to build that bridge. And then once you can get even just a little rinky-dink bridge, if you have a team, maybe one person can then go over to that bridge and plant a flag to start being full-time at a company. And then together, you’re building a bridge from both sides now to try and get to a point where then everybody else can then cross that bridge to get over onto this island where everyone is full-time and focused on business, which is really how we did it.

We all started part-time in a business in the beginning. I mean, again, we had kids, we had student loan debt, we had mortgages, all these types of things. And we couldn’t just quit our jobs to do that. But we did have different levels of risk tolerance. And so, as a result, we ended up getting to a place where my partner Ben was able to go full-time first. So he went full-time first, kind of like got there, planted the flag. And then together, we were able to build the rest of the bridge to get the rest of the team over to the island. And so that’s how I think about it. So I kind of reject this idea that you need to go all-in and you need to – I mean, you want to go all-in, but then you need to literally just commit financial suicide in order to do it.

Aaron  30:56
Man, I applaud you because that is definitely not the prevailing thought. And that’s actually something that I’ve pondered even myself, thinking, man, am I going crazy here to think that, you know, like you said, you said it so well. You got responsibilities, man. You got a house, kids, bills, and real life. And so it doesn’t have to be – these aren’t mutually exclusive decisions that have to be made. And I love that. I love that visual that you painted of building a bridge from here to there. And especially if you’re bringing a partner on or multiple people on, then you’ve got different avenues to make that happen. And then what I’ve had someone helped me was you do that until you reach a point where you owe it to your clients through or your startup, now it’s a detriment that you’re not there.

Greg  31:55
That’s right.

Aaron  31:55
And something like that, right?

Greg  31:57
Yeah, yeah, yeah. That resonates with me. Yeah. I believe that.

Aaron  32:01
Cool. Man, that’s awesome. And then, so one topic here that I always love getting people’s insight on this because I have zero experience on partnerships and so obviously you may want to be careful what you say if your partner is watching. But I would love to understand how does that whole thing go down. And because, I mean, it really is like a marriage.

Greg  32:33
It really is.

Aaron  32:33
And so how does that whole thing happen? What’s the dynamic like? How are you guys building your relationship and feeling like you’re covering down your assigned responsibilities and making the company work and doing it while not killing each other or resenting each other through that whole process?

Greg  32:55
Yeah. I would say a lot of it just depends on one, the nature of the relationship, and two, the nature of your relative strengths, right? And you have to be complementary, right? And I’ll come back to that in a moment. So the first part, the nature to relationships. So one thing that worked with Ben and I is so we were friends in business school, right? But the context under which we met was business, you know, as students, right? But it wasn’t just like old drinking buddies from my college who decided they wanted to go do something, right? So that kind of set up a foundation.

But that also kind of sets up – I won’t say boundaries, but it sets up a mentality around it. Even though I spend the most time with him, he and I don’t hang out together the same way I hang out with my buddies from the Air Force Academy, he hangs out with some of his fraternity brother, things like that. We still hang out and do things together. But the nature of the relationship is more centered around the business and the shared experience of the business versus the other shared experiences socially that we may have had. So in my case, that’s kind of how that worked.

The other thing that I think works very well is that we both respect each other and we respect what each other brings to the table and respect what is different about what that other person brings to the table. So he and I have different skill sets. We overlap in a lot of ways, but the areas where he’s strong are not my strengths, the areas where I’m strong are not his strengths. And so we end up being very complementary in our ability to work together versus two guys who think they have same answers to every single question. We will kind of defer to each other a little bit based on skillset, experience, and just sort of our personality types even.

Aaron  35:05
Yeah. I think that just kind of confirms it to me. Because I was just thinking, you know, I feel like some of the best sets of co-founders are people that just had to go into business together or they ended up being like, I mean, it’s not as dramatically Jekyll and Hyde, right? But one of you skews a little bit more one way, the other one skews a little bit more the other way. Obviously, there’s plenty of overlap there of course, but like you said, built on mutual respect and understanding.

Greg  35:50
I think that’s like a yin and yang type thing.

Aaron  35:43
Yeah, yeah. No, that’s exactly right. Yeah. And you know, one thing that you said that I thought was really interesting as you’re starting the relationship, and I think, for me, this is a takeaway, that the context, the foundation of the relationship from day one was centered around business. You guys were both students. You’re going through the same program. And so it lays the groundwork for that. As you said, you didn’t meet at some association or some neighborhood event or something like that. It was in that context specific.

Greg  36:20
Yeah, yeah. And I won’t go so far as to say that the other ones won’t work or that you can’t go into business with your best friend or even your spouse or significant other. It’s just from there, my hypothesis, anyway, is that it may be a little bit harder to define the lines and to not let the other aspects of your relationship creep into the business relationships. Because in that business relationship, there will be hard conversations and hard decisions that may not be popular, that would be very difficult to have with like your best friend, right? But within the walls of business, listen, you’re a fiduciary, right? You’ve got a fiduciary responsibility to not just yourself but any investors and your stockholders, your employees, all of the above, right?

Aaron  37:05
And then there was something that clicked in you that made you okay with not doing it a hundred percent ownership. You obviously saw something in him, he saw something in you, and you guys just instantly were able to shed any kind of a hundred percent self-centered ambition. You’re able to realize, hey, he’s got strengths, we’re better if we work together. And yes, that means I’m giving up half of my equity in the company, but that’s worth it to me.

Greg  37:37
Yeah. Because the pie will be bigger.

Aaron  37:39
Right. Yeah. The whole analogy of a small slice of a large pie versus a versus the whole pie, which has nothing.

Greg  37:47
Yeah, exactly.

Aaron  37:48
Yeah. So awesome. Well, no, thanks for sharing that. I realize we’re actually starting to kind of wind down on our time here and I just want to make sure that I’m not missing anything. We already covered challenges. You covered a little bit of advice for those who are wanting to start businesses, which I think is phenomenal. I loved your perspective there. What other parting shots, you know, if you had anything else on your chest that you hadn’t had a chance to say yet, but are there any other bits of advice that you’d have for folks that are looking to start their business or they’re in the boat that you were in, right? They’re still on the island. They’re in the middle of building their bridge. Is there anything else that you’d to share?

Greg  38:37
Yeah. I would say two things, right? So one would be just commit. Commit to it and just say, hey, listen, this is what I’m going to do. And part of it is going to suck. But I mean, you know, you’re a former Marine, or actually, I guess, you’re never a former Marine, right? So you’re Marine, so it’s like, listen, embrace the suck, right? There are going to be parts of it that it is going to suck, right? Just embrace it, lean into that, and just acknowledge it. And that actually makes it much easier to tolerate and deal with the hard times, right?

And then there’s also some things that you need to kind of really think about. To pivot versus persevere, right? So there will come points in your business where it’s like, okay, this is really hard. Is my operating model flawed or is my execution flawed or is the idea flawed, right? And being able to maybe start to think through, I mean, I don’t know that you’re ever going to know for certain which one it is, right? But if you get to far to realize that the idea that you had is not viable, don’t be afraid to change it or to adapt to your environment. Again, we learned this in the military, right? When the environment changes, our approach needs to change, right?

But know the difference between that and when, hey, listen, if I just keep going, listen, the fundamentals here are still sound. And if I just keep putting one foot in front of the other and continue to execute it, eventually I’m going to break through and I’m going to get through, right? And then every now and then kind of check, okay, does the idea still make sense? Yes. Okay. Keep going, right? And knowing when it’s just a matter of just having some grit and perseverance versus when it’s time to actually change course. Those are the things that you maybe have to kind of fine-tune your senses.

Aaron  40:19
I feel like that’s the fundamental – I feel like what you just described, I think, is the essence of problem solving and it’s the essence of the entrepreneurial journey. There’s so much unknown. It’s always easier when you look back over the blazed trail and things become more obvious, but in the moment, you’re trying to make the best decision you can with the information that you have based on your education, your instincts, your various signals. I mean, that is phenomenal advice. So appreciate you sharing that. How can people get ahold of you? How can people follow Sworkit?

Greg  41:04
Absolutely, yeah. So, I mean, Sworkit, we’re all over social media. @sworkit on Twitter, Instagram. We’ve got Facebook. I mean, but you can very easily find us on the web, sworkit.com, LinkedIn. We’re all over social. We’re just about everywhere. So you can find us there and you can find me, my Twitter handle is @gregorybcoleman. That’s how you can find me. I haven’t been as active on Twitter as I like to be, but I’m actually starting to lean into that a little bit more too. I’m finding that fun to kind of get in and kind of interact with people a little bit more.

Aaron  41:36
Awesome. Awesome. Well, Greg, I just want to thank you so much. Thanks for spending so much time with me. Thanks for sharing some of your insight and some of your journey. Thanks for taking us along that journey with you.

Greg  41:48
Well, hey, thanks for having me, Aaron. I’ve really enjoyed it.

Aaron  41:51
What a phenomenal discussion. I so enjoyed getting to speak with Greg. It was just a really enlightening experience for me. So I really enjoyed it. I hope that you enjoyed it also. There’s just a lot of great nuggets there. And I like how he rejects a certain prevailing thought. So I thought that was interesting. Again, I just want to thank you for watching. Thank you for listening. And I can’t wait to see you next week. Take care.

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