🎙️From Lagos to Birmingham: Bootstrapping to Billions and Scaling Belief Systems Through Constraints w/ Shegun Otulana, Founder & CEO of TheraNest & Harmony Venture Labs
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In this episode of Outsider Inc., host Ian Hathaway speaks with Shegun Otulana, co-founder and CEO of TheraNest and Harmony Venture Labs. Shegun shares his journey from arriving in Alabama from Lagos, Nigeria at 18, to bootstrapping his first consulting firm, and eventually scaling TheraNest into a national leader in mental health software. The conversation covers his unique approach to pricing, building a remote team, and the importance of eagerness and passion in serving customers. Shegun also discusses his transition from the CEO role, the creation of Harmony Venture Labs to support the next generation of entrepreneurs in Birmingham, and the influence of his faith and family in his career. Throughout, Shegun emphasizes the impact of creating intentionally and staying aligned with one's values.
Show Notes:
(05:09) Shegun’s Transition to the US and Early Impressions
(08:28) Founding Zertis Technologies and the Entrepreneurial Drive
(11:26) Identifying the Right Problem and Market
(13:18) Building TheraNest and the Mental Health Focus
(18:45) Differentiation and Pricing Strategy
(21:59) Remote Work and Team Building
(26:06) The Challenges and Benefits of Being a One-Man Band
(29:50) The Founder Mentality: Building a Culture of High Performance
(33:30) Scaling Up: From TheraNest to Therapy Brands
(40:33) Transitioning Out: From CEO to Board Member
(43:26) Harmony Venture Labs: Building a System for Startups
(46:55) The Importance of Family and Partnership
(50:43) Faith and Leadership: Guiding Principles
(53:14) Beyond the Bio with Shegun Otulana
✅ Host: Ian Hathaway - Co-Founder & Managing Partner, FOVC
✅ Guest: Shegun Otulana, Founder & CEO, TheraNest & Harmony Venture Labs
Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.
Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.
AI-Generated Transcript
Shegun Otulana: [00:00:00] I think what is more important is the eagerness to learn, the ability to put yourself in the shoes of the person you're trying to solve the problem for, and how quickly you can get yourself up to speed in a space. The most important factor around how quickly you can get yourself up to speed in a space is how eager you are to serve that customer.
How excited you are. To save that customer. So if I'm looking at two founders and I see one that's the expert and has all the experience in the space and everything, but they've lost the fire, the energy around the customer and the problem, and they just feel like I'm the expert, I know it all. I would not bet on that person over somebody.
Who I feel is green, but it's just fired up about the customers.
Ian Hathaway: Welcome to another episode of Outsider Inc. I'm your host, Ian Hathaway. Today's guest is Shegun Otulana [00:01:00] extraordinary founder whose journey spans continence industries and billion dollar outcomes. He's best known as the creator of TheraNest and Therapy Brands, the behavioral health software platform.
He launched in Birmingham, Alabama in 2013. He scaled the company into a national leader, culminating in a $1.2 billion acquisition by KKR in 2021, all after raising a modest $250,000 in angel capital. However, that success was anything but conventional. Born and raised in Lagos, Nigeria. Shegun arrived in Alabama at 18 with no network, no safety net, and no blueprint.
He bootstrapped his first consulting firm, launched products with his own credit cards, sculpted and scaled a remote workforce, and quietly built one of the most significant tech companies the state has ever seen. Then rather than cash out and disappear, he doubled down founding Harmony Venture Labs, and taking a leadership role in the startup community in Birmingham to help other outsider entrepreneurs build scale and own the next wave [00:02:00] of category defining companies.
I'm looking forward to speaking with Shegun about what it takes to build a billion dollar business outside the usual power centers, how to lead with purpose and overlooked markets, and why betting on Birmingham isn't just a hometown play. It's a long-term thesis. Shegun Otulana, thanks for dropping by.
Shegun Otulana: Thanks for having me, Ian. That was a wonderful intro. The intro makes me wanna take notes on myself.
Ian Hathaway: It's a real pleasure to have you here. A big thanks to Jewel Burke, Solomon for connecting us. She's the one who clued me in about you, and when I read your story, I knew immediately I, I wanted to have you on this show.
This is a platform that celebrates outsiders. You're an immigrant to the United States. You build a very successful software company and an industry that. You didn't have the experience in and, and it's one that's notoriously difficult for navigating as an outsider. You did it as an inexperienced founder and you built the company in Birmingham, [00:03:00] Alabama, which is probably not the first place people think of for building large software companies.
And now you're spending your time helping the next generation of entrepreneurs coming up behind you. That's really what this show is all about. So there's plenty of things to cover, but first I'd like to start with a concept that originated with you. When most people hear LA they think of Los Angeles, but the term LA means something different to you.
Tell our listeners what is a LA accent and how does a person get one?
Shegun Otulana: Oh my goodness. You've done your research here. So you've heard me say this before. Uh, it's a joke I have where I say, Hey, this is an LA accent, and people are like, what is this guy talking about? And I mean, this is a. La, lower Alabama or Lagos or whatever you wanna put it.
Accent. So that's what this is, which means listen carefully people.
Ian Hathaway: Yeah. Oh, I love that. Well, so you grew up [00:04:00] in Lagos, Nigeria, a family of 10 children.
Shegun Otulana: Yeah. So my mother had, uh, 10 of us and I was the fourth of 10 children.
Ian Hathaway: So 10 children, parents were entrepreneurs, certainly influenced you. What was it like growing up in Lagos and how do you think that prepared you for eventually coming to the US and becoming an entrepreneur?
Lagos is pure velocity.
Shegun Otulana: It really teaches you how to solve real problems with limited resources. That's anybody who comes from that part of the world, you really learn to create without waiting for permission. And that's a big part of. Growing up in Lago, it's the, it's the re it's the figure it out with limited resources.
Create your own momentum, figure life out. And that just translates very well to the entrepreneurial journey, which is probably a true story for many immigrants. So if there is one thing I would say that I did growing up in Nigeria, growing up in [00:05:00] Lego ship me, it would really be figure things out, create without permission, you know, move
Ian Hathaway: on that note of building things for yourself and moving.
You left Lagos at the age of 18 to attend the University of Alabama Birmingham. I know you followed your older brother who was already a student at UABI believe the journey of migrating to another country and resettling your life is in itself an entrepreneurial act. It requires that kind of entrepreneurial mindset and spirit, and maybe this is one of the reasons why so many immigrants.
That come to the United States, go on to launch companies. But before we get into your company building journey, I just would love to hear about your decision to come to Birmingham and maybe what some of those early impressions were or what those first few years were like for you.
Shegun Otulana: I think you are 100% correct that there is something entrepreneurial about packing your bags, leaving your family behind, and moving to a place where you have to [00:06:00] figure it out for yourself.
So it's not uncommon that you see a lot of entrepreneurs be immigrants, and I. For my journey. I think my transition was probably smoother than many people's transition, if I'm being honest. And like you said, that's because my brother was here, his friends became my early community. It did not mean that there were no changes and transitions that happened.
Obviously always moving from Lagos to. Birmingham, Alabama has its transitions, changing schools, all that stuff. But the thing I'll tell you is coming from Lagos, I was like, where is everybody? Because you're coming from a city of 20 something million people to a Birmingham metro of 1.2 million also. So I did love the quiet.
It felt like going from the volume of a market of marketplace to the stillness of a library. Yeah. And then the transition in terms of people understanding you and [00:07:00] dealing with preconceived ideas of what it meant to come from Nigeria was something you also had to deal with. In some cases it worked for you.
In some cases it worked against you, and you learned and you adapt over time. So, uh, from a personal standpoint, the transition was smoother than for many people, I'm sure. And then from a cultural standpoint, there were some things that you had to get used to, but having come from one big city to another city, I would say it probably wasn't as jarring as many people would expect.
And I. The people here were just very kind. That's the thing I see all the time. You know, there's this talk about southern hospitality. It is real. Is it real for everybody? No, but it is real for enough people that it's actually great. And I tell people all the time, if you are transitioning to the US from anywhere, you should definitely look at the South as a place to consider that.
That's just my opinion, given my experience.
Ian Hathaway: So look, you went to UAB, you have this kind of early impression, tap into an [00:08:00] existing community. Studied it systems. TheraNest is obviously the, the main event in your career thus far, and. I wanna get there in a moment, but I also wanna talk about how you got there.
I think it's really foundational to the way you built the company that you did. After graduating from UAB, you spent about eight years as an IT systems administrator for two local companies. Along the way, you started a software consultancy, Zerus Technologies. In 2011, you left your job and you decided to go all in on Zers Technologies.
What was the motivation for going all in on yourself at that time and what was appealing to you specifically about the consulting model?
Shegun Otulana: Right after college, I actually started this side gig with a couple of friends and eventually paired down to a friend and I, very smart guy, and the driver for me was always just.[00:09:00]
Entrepreneurship. It was all I knew. It's all I grew up with. I think it was in my blood. I just couldn't help myself. But when that first transition of erti didn't work out, I went, I took a job, a regular job, but the fire always burnt in me, right? And eventually at the urgent of my wife. Who looked at me one day and said, we all know what you really want and what kind of life you want.
We know you're an entrepreneur at the core. Go give it a shot. Give it another shot, and if it doesn't work, that's fine. I'm gonna be here. So that's when I restarted my entrepreneurial journey. And this time I wasn't waiting for inspiration. I had. Evolved enough. I kept studying entrepreneurship. I was kind of plugged into everything that was happening around startups that when I picked up that journey again, I had created a filter for myself that I was gonna use to evaluate ideas.
And those ideas I felt could come from looking for real problems. And I [00:10:00] couldn't think of a better way to go find real problems than consulting. So the approach I took was I was gonna be a software consultant. Talking to various businesses, small, mid-size businesses around town, and eventually I would find the thing that checks all the boxes that I could build a product around.
So that was the idea behind starting Erti as a consulting firm. Of course, I was also trying to kill two birds with one stone. I was hoping Zerus would also generate income for me. While I did that, the income side wasn't going all that great, to be honest with you. But I was seeing a lot of opportunities and problems, and my filter was kind of simple.
I needed alignment. I, I wasn't necessarily looking for. Building a unicorn. I was just looking for something that aligned with me and the way I thought entrepreneurship had a bigger chance of success. You look for tailwinds. Back then, I thought the, the thing was the movement towards SaaS. So I was [00:11:00] looking for an idea that could tap into the SaaS tailwinds.
I wanted it to be a very large market. I wanted customers, I could enjoy serving for a long time. I wanted it to be someone that could build a team around, and then I just did not consider myself a very good salesperson. So if this idea was going to require me selling door to door, like enterprise sales or stuff like that, I typically just eliminated.
So those were the things I was. Using as a framework, as I ran into different problems and eventually I consulted for a mental health clinic. I saw the chaos firsthand. I liked the people. The problem checked the box. It was they were looking for moving to SaaS platforms, so they kind of checked the tailwinds.
So the thing I would say is. If you get the timing right and the problem fits, the founder momentum feels inevitable. And that was a little bit of what I was looking for.
Ian Hathaway: So you hit on a couple of things there. Using the consulting model to find real [00:12:00] problems. Customer discovery is such an important part of a product oriented entrepreneur's journey.
You found a way to get paid for it. Another way to think about it also is getting real revenue. An earlier guest we had Doug Song, who built an iconic cybersecurity company, commented during the episode that it was his experience in consulting that got him more addicted to making money than raising capital from investors.
And so that framework was always working in the front of his mind about how do we actually make money from this business rather than, you know, raising lots of outside capital.
Shegun Otulana: I told my wife when I started in 2011, I said, Hey, I really don't want to do the consulting thing. You know, that's not my thing, but if you give me five years, I'll do the product thing.
I'll come to the product. I'm gonna spend 10 years building and doing something with. That was what I told her When I really went back and started dessert thing. Thankfully it didn't take me that long. By 2012, I had stumbled into. This was the idea. [00:13:00] And then we launched, uh, thoroughness in 2013.
Ian Hathaway: Wow. So you had that vision from the beginning.
You mentioned some of the factors you were looking for in building a product company. What felt different about this particular client project that made you decide, this is the one, this is the thing I'm gonna go after?
Shegun Otulana: So back then, I would typically be looking at two, three ideas at the same time.
Looking at the market, looking at the problems, talking to customers, and. When I first went to talk to the first customer, my design partner back then the counseling center, they wanted me to build them an EHR software. And I was looking at them like, what are you people trying to do? It's 2012. You don't need anybody to build you an EHR software.
You should just be able to go buy one. But I liked the people. I saw the problem, I saw the impact they were having. So in my head, I'm, I'm like, it checks that box. That's good. And it became clear to me that what they were looking for was not just an EHR. I [00:14:00] have to give you context. Back then, a lot of the EHRs served more of the enterprises and there were lots of crappy ones that kind of saved everybody.
Uh, but you had to install a cd or you maybe had a server in the back. And some of them were SaaS like, but not the experience people were beginning to get used to. These were the days when Gusto started coming out and QuickBooks Online started coming out. So it became clear to me that that was the experience they were looking for.
And I told them, lemme go find something for you to use and I'll come back to you. But when I went to look for something for them to use, what I also saw was a large market. A lot of people searching for this solution, I could see who my competitors would be that were kind of doing it right. So that got me really excited and that was when I started telling myself, is this it?
I like the people. It's checking the box of a large market. I. There's clearly a tailwind here, not just from taking advantage of the SaaS tailwinds, but there was also a regulatory tailwind around [00:15:00] the idea, because remember, this was HIPAA compliance High Tech Act. A lot of these people were really trying to get HIPAA compliance software without them having to deal with all the technical stuff around that.
So those were all the things that were checking my box as I was talking to this person and trying to help them solve the problem, and that's when. I looked at my wife, Ian. It's very funny because I was in the hospital with my first child. We were having our first child, and I looked at my wife and I said, baby, I think this mental health thing is it.
You know, this is the thing. So this was December, 2012, and that's when I felt like. This really checks the box. I think this is what I need to double down on and go build. She, you know, with a baby in her hand, she looked at me like, oh my goodness,
Ian Hathaway: what did I do? Yeah,
Shegun Otulana: yeah, I know.
Ian Hathaway: Exactly. So, so yeah, that was, that was it.
Well, it's never. A good time to do this. You just gotta do it, uh, when you're called. So you hit on a couple things there. Why this, [00:16:00] why now? Why you, why this big market? A lot of people searching for it. You talked about some of those macro tailwinds. Let's talk about the why you didn't have experience in the industry, given it's highly context specific.
You know, that's something that can be valued, having that experience, that network. When we talk to. Vertical software founders we're looking for founder market fit. Right? So deep industry experience or wisdom, and you were an outsider. Do you think that helped you do things differently? Did it give you an advantage versus maybe some folks who had been too close to the problem and didn't see it a certain way?
Shegun Otulana: I think being an outsider. Gives you an advantage in certain things. I think the person is more important than whether they're insider or outsider. Of course, context is specific for everything, so I'm always very careful about giving people, this is how you must do X. Like, like I'm always very careful with that.
I. I think what is more [00:17:00] important is the eagerness to learn, the ability to put yourself in the shoes of the person you're trying to solve the problem for, and how quickly you can get yourself up to speed in a space. The most important factor around how quickly you can get yourself up to speed in a space is how eager you are.
To serve that customer, how excited you are to serve that customer. So if I'm looking at two founders and I see one that's the expert and has all the experience in the space and everything, but they've lost the fire, the energy around the customer and the problem, and they just feel like I'm the expert, I know it all.
I would not bet on that person over somebody. Who I feel is green, but it's just fired up about the customers. We've even seen this in my own journey as an investor. When you are looking at a founder that wants to do something because they think there's a financial opportunity there, I. But they don't really love the people they're gonna be working for or [00:18:00] working with.
So what happens is when they hit those difficult points, they do not have the momentum and the energy to keep going versus somebody that's just excited about the space they found themselves. So. What helped me was my excitement about the space, my eagerness to talk to these counselors and psychologists and psychotherapists all day long.
That sped up the ability to gain knowledge. Did I make some mistakes because of my inexperience? Of course I did, but at the pace at which I was moving, I could quickly overcome the mistakes and still have an advantage, and I think that's really what matters,
Ian Hathaway: the tenacity of the entrepreneur. I think having that beginner's mind can actually be really helpful.
One of the things that you did that was different, which could be tied to this is your pricing model where a number of your competitors were charging on a per seat basis for the clinicians. Pretty much all my competitors. Yeah. And you did something [00:19:00] different. What was that and how did you get to that insight?
Shegun Otulana: One of the lessons I, I learned, and I still believe in strongly, and I talk about all the time. Ease. You have to be differentiated for a particular person. Like you have to find that customer that you're differentiated for along at least one dimension. It could be the way you deliver the solution that's pretty unique and makes life so much, much easier than how other people are delivering the solution.
It could be pricing, you know, all kinds of ways. And for us, at the beginning, we were trying to find what our differentiation point was. In talking to all these customers, it became clear that for the nonprofit sector, they were not as excited about paying for every seat. As the private practice folks and the private practice folks had a lot of choices in the market and everybody priced per seat.
But I would talk to a nonprofit and they'll be like, well, we [00:20:00] have 15 people on the team, but you know, half of them are part-time, so you know, is there a discount for that? We would keep getting those kind of questions. So they liked our software because we thought about certain workflows they had as, as nonprofits within the context of delivering care.
So what we did was we decided, you know what? We're getting a lot of very interesting excitement and conversation with the nonprofit counseling centers, especially the larger ones. So let's not charge them per seat. We're gonna charge them per active customer. So whoever they're seeing scheduling and billing for is the only person they're gonna pay us for, and they loved that.
So that's started getting traction among the mid-sized nonprofit counseling centers. And I think as an entrepreneur, you always have to look for this entry points that gives you a differentiation in the market. Differentiation is really how you win at the end of the day, and that was one of the differentiations that [00:21:00] helped us.
And it came about just because, again, we were having so many conversations, and when I say we, honestly, it was just me. Back then I didn't have anybody else. But in all those conversations that just kept coming up and that gave that first. Momentum to the business because now you're closing a deal. Every day you are closing customers every day.
The selling process gets easier. You're excited about that next conversation. Yes, you're still closing the private practice good folks, but you're also able to really get momentum in this particular side of the market, and you keep going from there.
Ian Hathaway: So it was sort of this engagement with a potentially underserved segment of the market that you had a differentiation around, not just the product offering, but how you positioned and priced it, which was ultimately larger contract values for TheraNest.
Important lesson there for founders. Something else you did differently, which was not common at the time, is more common now, which is you built. The [00:22:00] team remotely. We had an earlier guest, Wade Foster of Zapier who talked about all the advantages of building a remote first team. He wrote a book on the topic, but that there's other things you have to think of, right?
It has to be the right fit for your company's culture. There's a lot more intentionality that needs to be said in additional planning that's required. What was the motivation for you building? Fairness remotely and maybe what are some of the lessons that founders today can take from that example? The motivation for me was I had no choice.
Shegun Otulana: That was the, that was the first motivation. You have to find a segment of the business where you can, if you do not raise a lot of money, which we didn't, you know, we couldn't raise money. It took us 10 months to get our first investor dollar, so. My ability to recruit was very limited. That was one we've talked about Birmingham.
It's not, it's some large. [00:23:00] Market with talent all over the place. Has it gotten better since my journey started? Yes, by a lot. But if you think about 2013, it was much harder, right? So I had to think about talent globally. I had to think about where can I find the best people at the cost that I can afford.
So that was one of the things that I was thinking about. That led me to go the remote first route. That was a big motivator back then, and I think the quality of people you could get back then that were remote was very high because remote then was a deliberate choice. You literally designed the company around it.
You designed the team around it. You designed your hiring process and your hiring practice, and your onboarding process and your onboarding practice around it. You could also pick and choose, or you could choose to say, this person doesn't fit the mold of somebody that we think will be very, very successful as a remote person.
So we're not gonna pick [00:24:00] them. We're gonna pick the next person. Because one of the filters back then was I would ask, have you done remote work before? And if you said, no. The threshold for getting hired went up. Like, now I'm really testing for your ability to have a lot of agency by yourself. And is this somebody that's gonna really not just be task oriented, but think broader?
Because one of the challenges about remote work is remote employees sometimes can become just task oriented, which is not the way to build a startup. They just do the thing they have to do and then they move on. The challenge you now have today is if you ask somebody, have you done remote work before?
Almost everybody's gonna tell you yes because COVID happened. But how do you now test to make sure this is not somebody that's just gonna be. Task oriented in everything they do, and once they do their tasks, they're done. Thinking about your company or your, or your customers, how will you nurture thinking, broader thinking across the whole business?
How will you turn somebody to be project [00:25:00] oriented and company oriented within the context of a remote work versus just being task oriented? So how do you navigate that is something that founders have to be much more deliberate about. I think companies like ours that started long time ago, Zaia that started long time ago actually had an advantage to being remote.
That I'm not sure is still an advantage today. And everybody's gonna come at me and make, get mad that I'm telling them to stop doing remote work. I see a lot of companies, I see a lot of founders. We have a lot of investments. I'm just telling you from what I see that. It is pretty clear that unless a company is very, very deliberate about it, remote work used to be an advantage, and I'm not so sure it's an advantage anymore.
Ian Hathaway: I agree with that, especially early teams, especially in product and engineering. It's important for that pace, that proximity, trust building and so on. You know, you [00:26:00] mentioned before when you said we were engaging with customers, it was just you. You talked about things like agency with some of those early remote hires because you were sort of a one man band in many different domains.
When it came time to hire, you knew the details, right? You knew who you were looking for because you had done those jobs before, but ultimately there's a transition that needs to occur. You, you have to give those people power. You have to give them decision making authority. You have to give them that agency.
How do you feel like being the one man band for a time period set up your leadership approach over the longer term? Maybe secondly, do you think that this is something that founders can overlook early on? That they don't spend enough time building out critical functions themselves and that they can at times hire too early?
Shegun Otulana: 100% constraints. Lead to [00:27:00] creativity. That's the thing here, right? And you doing a job within the constraints of being a one man band helps you think about efficiencies within that job that you can then pass on to the next person that comes in to take that job from you. If you take my story, I didn't have any resources, but I knew the bigger challenge for the.
In those early days was not the ability to build the software. I could build the software. It was my ability to sell the software and market the software that that would be my biggest problem. So what I did was I found a really great engineer because I knew what a great engineer would look like and I passed on a lot of the engineering work, even though I was still the product owner and the owner of the vision and helped do a lot of the, what is the customer's experience like what will be magical for the customer.
But I left the engineering work and I really started focusing on [00:28:00] how do I become. Somebody who would drive traffic into the website and do marketing. And one of the things that really helped me then was a book by Rob Walling that he had written for engineers who were starting companies called Start Small, stay Small.
We didn't stay small, but we did start small and took a lot of lessons from that book and put it into practice from a marketing and growth marketing standpoint. But like you said, the constraints actually helped us. When I now got a little bit of funding that we knew exactly where to put the money from a marketing standpoint to significantly drive growth because I had been doing the marketing work.
So when October came around and we ended up operating a a seed round, we knew this works, this didn't work, this works, this didn't work. Let's double down on what works. Those are some of the benefits of doing the work in that early day. As a founder, by the way, this is one of the challenges with. Repeat founders [00:29:00] who have had a lot of successes, because what ends up happening, of course, is you now can go hire people to do the work, and maybe your learning velocity slows down because you're not the one doing the thing.
You're not doing it through other people and the rego that you bring in and all that may reduce. So it's kind of weird, but this is it. If you are a repeat founder, it is much more important for your early team. To have that founder mentality more than if you're actually a first time founder. 'cause if you're a first time founder, you are doing everything and you can really condense what you pass on to the team.
If you're a repeat founder who's who's had a lot of success, especially if you've not a lot of money and you can hire people, you are delegating that to these people. And now you need people that will have that same mentality as you had when you were a founder with everything they're doing so that you can learn faster.
Because you cannot [00:30:00] avoid the learning phase, and it's the quick iteration that really helps. So now you need those people to think like a founder because you're now not in all the details versus the first time when you did the thing.
Ian Hathaway: So you talked about that founder mentality, which I think is often a challenge for founders, right?
You're on a mission and your employees may not be. So you either need to filter for that as you're bringing people on, or you need to create an environment for that, or hopefully both. So I guess that kind of veers into conversations around. Culture, creating that sense of mission requires creating trust, which requires vulnerability.
I can imagine it was compounded by the fact that you were resource constrained and building remotely. How did you create that sense of culture? Obviously the company was successful, so you were certainly able. To create a culture of high performance. I'm sure some [00:31:00] mistakes were made along the way. I'm sure there's things you wish you had done better, but I'm sure there was also a lot you got.
Right. So just talk a little bit about how you went about building a culture in that unique set of circumstances for fairness.
Shegun Otulana: So culture is ever evolving. It means different things to different people. For us, culture never meant keg parties. Or things like that because we didn't have the funds to do that.
Culture for us meant really alignment of values, doing whatever we had to do to make the customer happy. Culture meant, since we're not all in the same room, you have to be able to exercise good judgment, and here are the rules and the guardrails for exercising. The good judgment. Now go around with it.
Culture. Men move fast and. We rewarded that. And culture also meant learn and share. So even though we're a small company, we didn't have a lot, we still had a learning stipend for [00:32:00] everybody. And then we wanted you to say what you learned. The place where I would say we didn't do a good enough job as we got bigger was we didn't ritualize enough of those things.
Because the way you reinforce culture is through storytelling and ritualization. As a small team, we weren't a hundred percent distributed anymore, but we were primarily distributed. As we got bigger, we didn't have a lot of rituals that were easy to have in person, and that probably created some issues for us later on as the team kind of grew.
So I, I would say culture is the values you share, the things you reward, and the way you really sustain it is what are the rituals and the reward systems around it. That would scale for your own context, whether it's in person, whether it's remote, whether it's hybrid. We got it right in the early days and then we didn't scale it properly as we got bigger and then we had to keep going back to try to fix things.
When we realized, oh, there, there is a [00:33:00] challenge here. My own individual interactions with people was a lot of what sustained the culture in the early days, but that is not going to scale. One of the things I had to learn about myself as a founder was to learn how to scale my one-to-one conversation, which I felt I was very effective at, to a one-to-many conversation that you need as a company gets bigger and you have to build the engine around that.
Ian Hathaway: That's a good segue to the company scaling things. Were going quickly about three and a half years or so from launching TheraNest. You evolve the platform into therapy brands. I. Which again was maybe an unconventional move, right? We talked a lot about for vertical software founders staying as narrow as possible for as long as possible.
Maybe you had done that, but the decision was made to expand into [00:34:00] more verticals. What was the thought process behind evolving the company into this larger platform? And maybe before you dive into that, could you just level set a little bit about where the company was at that stage in terms of headcount or revenue or anything you're comfortable sharing about how fast things had grown up into that time?
Shegun Otulana: Yeah. So if you think about fairness, we started in 2013. The first year was a wash. I was barely surviving. There was no resources, but we're making it work, adding customers, everything else. So October we got funding, and 2014 we started growing. That growth continued into the end of 2014, so that by 20 15, 20 16, we were several, several million in a RR.
And I could just see the trajectory. So by 2016, we're north of 5 million. I'll just put it that way. In era growing high, triple digits. So you could just see what was ahead of you. Yes. And that kind of growth is pretty [00:35:00] exciting. But now I, I see what's possible. You, you have to remember, our ambitions change with time and everything else.
So as the company grew, my ambition actually really grew with it. I had two personal priorities I was trying to solve for. Even though this thing was growing very, very fast, I still really had nothing to show for it personally, right? Mm-hmm. It's not like I was just paying myself a gazillion dollars and everything else, and I felt a strong sense of obligation to the angels that I put money in it.
I also wanted to de-risk my family, and I wanted to get to even bigger scale unbelievably fast. So those were the two personal priorities I was really trying to optimize for. I'm about to take on this huge risk. If this thing goes to zero, what will I have to show for it? Which is why I don't really have a problem with founders taking some chips off the table.
Some investors do. In my case, I wanted to do it because I wanted to go all in, and I just wanted to go all in without really putting my [00:36:00] family at significant risk. So that's when Therapy Brands was born. And the other thing is the mental health space is highly fragmented. It's fragmented around which area of mental health you're serving.
Even regionally, the, the government agencies regionally, there's a lot of fragmentation. So with our growth, we wanted to get into more areas of mental health, and that meant we also had to take advantage of maybe buying our way into some of those segments of mental health. So that was the big ambition that I was going after.
And like you said, Ian, you know this was 2017. There were lots of people that were like, why are you doing this? There were lots of investors that were like, oh, we don't do that. Like especially in the VC side, we can't let you take chips off the table. Well, we don't want you to do acquisitions or on and on, but private equity, let me do both, which was why I won the private equity round.
I had great partners. I had [00:37:00] Providence Strategic Growth as a private equity partner, and, uh, greater some ventures, which is more of a family office that be like private equity. PSG was the primary bigger check, but it wasn't because the company needed money. So that was the other factor there. We needed no cash.
We, like I told you, we're still very small, very, very efficient, making a ton of money. We were only doing this. For those two reasons. A partner that could help us scale strategically and de-risking for me and whoever on the team also wanted to de-risk. So they came in and we kind of continued that journey together.
So I saw some of my CO to them, some other team members did, but the company itself didn't really need cash on the two 50,000 in DUR round we raised was all we the primary. Fund whoever really raised from a balance sheet startup fundraising standpoint. So that was a totally different journey. I don't know how we can, how [00:38:00] much we'll go into that, but there are also lessons that came with that journey.
I, I'll be honest with you, I did not like the therapy brand's name. I think this is the first time I've ever said that we sold it to KKR for 1.25 billion and the new CEOI, I think they just changed the name to health, which. You can build something around, but truthfully, I hated the name. I didn't feel like it had a soul.
The name had a story, it had a soul. My wife actually named it Theist. Yeah. And there was, there was a reason behind it. And the brands felt corporate and transactional. So one, one of the lessons that actually came out of that is scaling isn't just a financial thing, it's actually also kind of emotional for the founder.
And as you scale. You need to make sure you hold on tighter to the soul of the thing because it's a key part of the business. So, so that's actually one of the lessons that came out of that for me.
Ian Hathaway: I think that's a really important point that I want to double click on in a second. But I wanna [00:39:00] just clarify that timeline with listeners because it's really important.
You ultimately sold this company for 1.2 billion to KKR along the way. You know, you did some secondary transactions to take some chips off the table. Having private equity partners to grow the business through some acquisitions as well, but I don't want to get it lost in here that your seed round that you referred to earlier was really a small angel round.
It was 250 K from local Birmingham entrepreneurs, a family office. I just want to remind listeners, because there's a lot of folks out there today who are building software companies very much with the venture backed mindset of. I need to raise money in order to build a product and find customers and do the things, and you are a case in point of why that is not necessary.
Secondly, I share your frustration about why I. [00:40:00] VCs and others looked down on this idea of taking secondary transactions. We had Scott Dorsey on the show who raised small amount of capital on balance sheet, but the first funding round he did other than some friends and family was with Insight Partners.
They did their series A and Insight actually encouraged them to take a significant amount of money off the table just to sort of relieve that founder stress. 'cause a lot of these folks who had also invested were actual family and actual friends and it took a lot of that pressure off and so can't agree with that enough.
But to circle back to the emotional aspect of this, by the time the KKR acquisition occurred, you had already stepped down as CEO and you stayed on the board. I know you're fully out of the company now. Talk a little bit about. That transition, you created this company, you build it, you scaled it, and now you're sort of slowly transitioning out of the company and you're fully out now.
[00:41:00] What has that process been like for you?
Shegun Otulana: In 2020, I stepped out of the CEO role. I was still on the board. I was actually still pretty engaged, not in the day to day, but I would engage with the CEO that was brought in to run the business in that time period. But in all honesty, my focus, my goal was can we just get this thing to the exit?
For many reasons, Ian, honestly, I was not, I felt like there was some level of innovation and drive. And customer focus and engagement, that as a founder you want that. Now you have to talk to the board and the PE guys and everything else to get done. And I was like, this is crazy. So let's just get this thing to the exit and let's make sure the people who came on this journey get a reward.
So that was kind of what the journey was like from like April, 2020 all the way to like January or so when we did the deal with KKR that, that it finally closed in. [00:42:00] I think April. Yeah, so. The other thing was around that time, I'd already started thinking of what's next for me? Like what do I want to do next?
I started thinking about the impact I really wanted the and therapy brands to have on the community. That was not gonna happen anymore given the choices I had made around, I. Capital and capital partners and things like that, because let's be honest, the private equity guys, great people, I just told you, they're good friends of mine.
I do deals with them, but they don't care about Birmingham. Okay. They just care about their companies making a return. Yeah. So, you know, I started thinking about things like that and that started influencing my decision. I would say the, the one mistake I made between that transition period was I should have fully waited till the therapy brand's journey was over.
Because even though I told myself that journey was over, it wasn't, I was still in weekly calls with the CEO, I was still talking to board members and I should have waited till the [00:43:00] journey was fully over knowing that an exit was coming and that's what we're all working towards. But honestly, I knew what I wanted to do next.
I wanted to be a founder building things, but I also wanted to build systems that build things. And that, that was really what was driving me, and I was just looking forward to when that would happen, uh, during that transition period.
Ian Hathaway: So let's talk about that. You're all in on Birmingham. You're all in on Harmony Venture Labs.
Tell us about what HVL is and what you're most excited about right now.
Shegun Otulana: Yeah, so after Terrane and Therapy brands, I, I didn't want to just build one more company. I wanted to actually build this system that could launch many companies. There are many reasons for that. For me, HVL is that system. You have to think about what Birmingham was like when I kind of started.
We were still early in the creating startups journey. We still are, to be honest with you. So I've been very fortunate. The first exit was pretty significant for me, and then I had more and more [00:44:00] so, so I'd invested in a lot of companies in Birmingham, but most of them were not going anywhere. They weren't getting traction.
It was pretty clear that idea development, idea formation and nurturing and the diligence process around turning an idea to a great idea was still relatively new in the ecosystem. A lot of playbooks that people on the, in the hubs and knew were not yet in the system. In terms of how do you think about the business?
What's the business model? How do you get into the market? So my goal was, is there a way to have a thing that can help gene this thing up and increase the momentum, the, the part of the gaining of momentum with within the ecosystem. Cities like Birmingham, they have a ton of opportunity. They're emerging opportunity cities.
But they suffer from attention deficit, right? The world isn't watching. You can't wait for the spotlight to shine on you. You have to kind of [00:45:00] generate your own gravity. You have to generate belief, and I felt a studio model was actually a good way to do that in a place like Birmingham, even in a dispersed world.
The studio can become like a center of gravity for founders to learn. So that that's really what led to building HVL. And there are lots of iterations and learnings that we've gone through in that journey of trying to build a studio in a place like Birmingham and Birmingham itself has come a long way.
Ian Hathaway: Just quick hit on that. Where is Birmingham today and where do you think it's going?
Shegun Otulana: So today, you know, you have my exit, you have Bill Smith that built, shipped, and sold it to Target. You have Tony Somerville with fio. You have so many other success stories that have come out of Birmingham. It's kind of funny.
All of us were. Almost like the same cohort when we were starting back then. So that's helped. And today you have companies like Link coming outta Birmingham. You have [00:46:00] more venture money trickling in. We can also invite people in now and there's something for them to take a look at, unlike before. And one of the things that has changed here is that the city, the state has also begun to realize how important this part of the economic.
Ecosystem is, and there's a lot more support around it with things like Innovate Alabama and other initiatives around the state today, Birmingham, we have stuff like SLOs Tech that you're gonna be coming to later on. Yeah. None of those things were there. You know, none of those things were there more than a decade ago when we were doing this journey.
So Lau tech would get hundreds of people from all over the southeast and beyond that would come to this tech. Event. So those are a lot of the things that have really changed here now.
Ian Hathaway: It's really exciting. I'm looking forward to visiting here in a couple weeks. Switching gears. You talk a lot about community, about support, and you use the phrase center of [00:47:00] gravity for you.
That feels like your center of gravity is your family in particular, your wife, Mary, you met back in college. I. She's been a vital part of your journey. You mentioned that not only did she encourage you to start Zerus, she named TheraNest. She's a founder herself now running Blight Free Birmingham, and the two of you are working together on a number of philanthropic efforts, including a $1 million scholarship for foreign students at UAB.
How do you think about her role and your success, not just as a a life partner, but as a creative and strategic force? What can others who are married or partnered, what can they learn from your experience?
Shegun Otulana: Oh, the partnership is so important. It is hard to overestimate the impact that your partner is gonna have in your life.
For many people, it's a 40, 50 year decision. [00:48:00] That the impact is unbelievable. And for me, I was just very fortunate. I found somebody that shared my values and was just a partner in, in the true sense of it with my wife. I think the important thing is like when you think about family, there is a lot of similarities with startups.
Right. You almost have to treat family. Sometimes the way you treat startups, it's not exactly the same. So I need to be careful here, but you do need structure. You need clarity of vision, you need alignment, and then you need a lot of grace when things go sideways, especially as as an entrepreneur, you have to give attention to what matters, right?
In startups, you lead with vision and families. You need vision, but you also need a lot of attention. So the way I've just. Thought about Mary is to never take her for granted. I, I think that's the big thing for me in my life journey, is [00:49:00] no matter how many years pass, never take her for granted. Never devalue her or her opinions, even when you disagree and give the full attention and the full respect that the partnership.
Needs and deserves. I honestly cannot even put it into terms. You just have to give it the respect and attention that it deserves.
Ian Hathaway: That was beautiful. You touched on your children. You're a father of four. You were one of 10 children in Lagos. We talked about earlier, you spoke about how. You were influenced by your parents, how that helped fuel your entrepreneurial journey.
And you know, you've spoken also about raising a family. We're giving as a core value. Watching your example, what do you hope are the lessons or habits that your children are picking up from you?
Shegun Otulana: Everybody thinks about legacy. It means different things to different people, but when I think about my children, legacy is not.
[00:50:00] Just what I build or have built. It's also what my kids believe is possible because they saw me build something and in many cases saw me build it with them in mind. Ultimately, all of us want to raise healthy, balanced people, but we also want to raise people. That wanna give to the world, that look around them and see that everything they see is because somebody else said this needs to happen and that they should take initiative and make things happen in the world, whatever that means for them.
So that's a lot of also what drives my work.
Ian Hathaway: Yeah, I love that. So, one last question. I wanna talk about your faith for a moment. You've described yourself as. Unapologetically a Christian, and you credit your faith as a guiding force in your entrepreneurial journey and your personal development. How [00:51:00] specifically has that faith guided you as an entrepreneur and as a leader?
And maybe for listeners out there who may not have a practicing faith, what are those principles that your faith has instilled in you that you think are useful that could be applied in their own leadership?
Shegun Otulana: So I think I would answer this with a response that Jesus gave to someone. Now we're in church.
Oh, Ian, what have you studied here? He said, look, love God with all your heart, your soul, your mind. And he said, the second, love your neighbor as yourself. That is the basis for a lot of things for me, is nothing should rise to the level of. God in my life, not my success business, not money, not fame, nothing else because I need to live that space where all my heart, my soul, my might, [00:52:00] has this high authority that guides the impact it has in the world.
But all of that means nothing if it's just for me or about me. So now I need to channel it to my fellow humans. I. I loving my neighbor as myself. So that's foundational. And then on top of that is my belief that faith is actually a source of wisdom. Because when you take the principles to heart and you use it to guide your life, you actually live a wise life.
So I, I'm not interested in having all the answers or telling people that I have all the answers. That's not the definition of faith for me. The definition of faith for me is to be guided by. God's principles and to realize that the full expression of it is in what I do with the resources and the time and the energy that I've been given.
Ian Hathaway: So many pieces of wisdom in there that founders can and should take forward service to others being uncomfortable in the [00:53:00] unknown. And look, at the end of the day, it's just business, right? There are. Other causes, more important things in the world than just business. That's a great note to end on, but here on Outsider Inc.
We like to finish with a segment we call Beyond the Bio. These are just a couple of quick hit questions that let us step away from your resume a bit and really dig into what makes you you.
Shegun Otulana: Sounds good. You're about to get me in trouble.
Ian Hathaway: I know nothing scandalous here. What's a quick piece of advice from a mentor that stuck with you throughout your journey?
I.
Shegun Otulana: I would say show up, especially when you don't feel ready, because that's how you get momentum. So that's the thing I, I tell myself, I actually tell my kids, I tell my team, be comfortable with ambiguity. Just show up and do the work. And that's how the momentum starts.
Ian Hathaway: Yeah. Take action. Who is an unsung hero in your life and [00:54:00] what has been the impact they've had on you?
Shegun Otulana: We've talked about my wife, I, I think that's the biggest hero. And then I, I would have to also say, my mom. You have to think about this woman who raised 10 kids while being an entrepreneur and definitely a hero in many, many ways. 100%.
Ian Hathaway: Who is someone in the Birmingham startup community who doesn't get enough credit and deserves a shout out?
Shegun Otulana: There are so many, you know, there are lots of quiet builders here who've been showing up for years. No Spotlight. They don't get on podcasts like I do and us like that. Not yet, but in, in, in many ways, they're the foundation for what's happening here. One name I would definitely mention is Susan Matlock.
Susan started or became the Innovation Depot. That was where I started my journey from, and a lot of us started our journey from there. So I have to shout that out. And then at a bigger scale, I even have to shout out some of the like Jared [00:55:00] Weinstein that has done so much. Jared's is successful in his own right by many measures, but he is just done so much to put on the map.
Things like Endeavor and VFA. And fellowship that it started. So there are so many, honestly
Ian Hathaway: incredible. Tell us something most people don't know about you. Something outside of work. It could be a hobby, favorite travel spot, a guilty pleasure, or maybe even a hidden talent.
Shegun Otulana: I don't know how many people know this, but I, I love music.
I play music. I also play a lot of racquetball. I love racquetball.
Ian Hathaway: Okay, well we're gonna hit both of those because the next question is, what are one or two songs you'd like to add to our Spotify founders playlist? Something that kind of fuels your workday or maybe inspired you along the way as an entrepreneur,
Shegun Otulana: I listen to a lot of Afrobeat Burner Boy and As, [00:56:00] but I kind of listen to everything.
Ian Hathaway: Mm-hmm.
Shegun Otulana: To be honest with you, because I love music in general.
Ian Hathaway: I remember the first time I went long ago, I went to see the Chicago Afrobeat project. I had never heard of Afrobeat and I was immediately hooked. So can relate to that. So last question. If you could give one piece of advice to someone about to start their first company today, particularly someone who's a bit of an outsider, what would it be?
Shegun Otulana: You are not just building a company, you're building a belief system. So think about what that means. Don't chase hype. Search for alignment, build a tribe around you and stay in the work long enough to build something real. And that means you don't need a perfect plan. You need a real problem. For a real person and then find the courage to start that.
That's really what I would tell someone.
Ian Hathaway: Wow. That is a phenomenal answer. I can't think of a better way to end. Such a great conversation. [00:57:00] Shegun, thank you so much for joining me, sharing your time and wisdom with our listeners. I can't wait to share it.
Shegun Otulana: Thanks, Ian. I really appreciate this and look forward to seeing you in a few weeks.
It's gonna be fun.
Ian Hathaway: Me too.
Shegun Otulana: Thank you.
Ian Hathaway: That's a wrap for today's episode of Outsider Inc. A huge thank you to Shegun Otulana for joining us and sharing his incredible story. Shegun didn't just build a billion dollar company. He built it with intention from bootstrapping in Birmingham to a massive exit. Every move was thoughtful.
How he priced the product, how he built culture remotely, and how he's now reinvesting through Harmony Venture Labs. What stood out most wasn't just the scale of what he built, but the clarity of purpose and a deep respect for people, customers, team. And community that shaped his every decision. It's a powerful reminder that building a great company isn't just about what you do, but who you are.
I look forward to following his journey as he continues to work [00:58:00] towards building a brighter future for the next generation of entrepreneurs in Birmingham. If you want more from outsider, inc, don't forget to subscribe to the platform@outsiderinc.substack.com. It's packed with highlights from today's episode and bonus insights you won't wanna miss.
You can follow Outsider Inc. On YouTube, Instagram, TikTok, and LinkedIn at Outsider Inc. Pod. You can also follow me on X at Ian Hathaway Outsider Inc. Is produced by Spellbinder Media. We'll be back soon with another fascinating outsider conversation. Until then, thank you so much for listening, and remember, great entrepreneurs can come from anywhere.
See you next time.