Branching Out by Bonsai | Caleb Sewell on Leadership and FC Tulsa

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Matt Butler: Welcome back to Branching Out. This episode, we finally get to talk to Caleb. He's a great footballer, as you know. He's currently leading FC Tulsa as their General Manager. Of course, I'm talking about Caleb Sewell. He's the former goalkeeper for the New York Red Bulls, FC Toronto, and many other clubs across his long professional goalkeeping career.

We talk a lot about his recent success with this Tulsa team, things he's thinking about doing next year, including winning the USL Cup and championship. And then also just how all this experience from playing to leading teams relates to opportunities in business, in leadership, in management, and honestly in parenting and many other realms. Caleb is a really great guy to talk to. Really happy he stopped by.

If you are liking the Branching Out series, please do us a favor. Go ahead and like the videos, subscribe to Branching Out, or to the Bonsai channel on YouTube, and check us out on your favorite podcast tool, whether that's Spotify, RSS, or many other platforms. We hope you had a wonderful holiday and looking forward to our next conversation.

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Matt: Awesome. Thank you for coming out to our office.

Caleb Sewell: Thanks for having me.

Matt: Happy holidays, Merry Christmas. Hope you're enjoying our minus 5-degree day here in Chicago. But I know you're not unfamiliar with the weather we have here given the fact that you were up in Toronto for many years. Is that right?

Caleb: I was there going on three years as a player and then later on as a player-coach, and then that's where retirement happened as well. They equally had their snow and the big city feel. So, it's cool to see this here today.

Matt: Well, Caleb, thanks. I think that's a great jumping-off point. I know we'll talk a lot about your team, FC Tulsa, and where you see that going in a few minutes, but before you ran teams, you were a player yourself. Could you tell me a little bit about your exciting career?

Caleb: Half Australian, so that's where you get the weird accent. I grew up in Australia, my dad's American, mom's Australian. I played a lot of cricket growing up and then pivoted to having to choose between soccer and cricket. I went the soccer route and that took me to England. It took me to Italy, took me to many different places. Portugal, where I met my wife. I went there speaking no Portuguese and am now being somewhat fluent.

I played in the MLS for a number of years. I played in Europe as I mentioned for a number of years and then decided to retire and take this crazy job. It's been a ride.

Matt: Goalkeeper turned executive. Was there any part of that playing experience that got you thinking, "Hey, maybe I should be running these teams?"

Caleb: It's funny because when you work your way up the ladder as a player, you go through many different experiences. You'll get really well-run clubs. You'll get clubs that are budget-conscious. You'll get clubs that just want a promotion, so they're trying to figure out how to compete but stay alive and stay afloat.

As time went on, I thought I wanted to go into the coaching route. That was natural progression in terms of wanting to help people. You can't play anymore, but you can be close to it, you can be competitive. Once you're away from actually playing it, what's the next best thing? I think that's coaching perhaps.

But really, we owned businesses away from the field. As time went on, it really got me thinking: is it coaching that really interests me, or is it being the connector of that coaching piece of those business decisions and sitting in between the technical and that business side? I think that's where my skill sets lie. It's one that I enjoy wrestling with—building things. You want to construct it from the ground up and have a vision. That resonated with me and that's where I find myself right now.

Matt: That's awesome. I had a not nearly as long and successful career as you had, but I do remember the period of life moving from playing and then figuring out what you do after playing. When you play, that's your life. It's so immersive. I was lucky enough to dabble a little bit in coaching. I was maybe 23 or 24 when I was doing this, but you learn pretty quickly if you didn't already know, coaching is very different than playing. In many respects, it calls on all different things. You really have to have a separate calling or passion for it.

Caleb: 100%. Just loving the sport is important, but it's not the only thing that matters.

Matt: And I would imagine it's probably the same running a team.

Caleb: When you're a player, you wake up, you go to training, you go home. It's very individualistic. I do my job and that's it. On this side, when you come through, you realize it's so different. There is such different decision-making coming not just from me as the individual player. You now start thinking about the whole setup, the coaches, the staff, the ownership, your budgets, and all these things. I think it's completely different from a playing perspective. I have a newfound respect for the coaches and general managers and people that I've played for before because you never really understood. Now you get that on the flip side.

With any genre of work, if you don't have a passion for it, ultimately you're not going to be as successful as what you may want to be. There are times where I'm at work and it's 8:00 and my wife's calling asking, "Are you not planning on coming home today?" But genuinely, I enjoy what I'm doing. That comes to the passion, but also the struggle of trying to build something and create something. That's really interesting for me.

Matt: I would love to hear a little bit more about FC Tulsa. I know there's been a ton of exciting achievements this year. Those successes probably didn't happen overnight. Tell me about your journey leading FC this year and all that led up to it.

Caleb: It was a roller coaster. I took the job probably this time last year in December. The biggest thing for me was understanding the club hadn't been successful for the previous few years. They hadn't been in the playoffs at all. They hadn't won anything. For me, it was people asking, "Why do you think you can win there?"

But that was the beauty. I met with the ownership group. They were very invested. They wanted to win. I think if you have that backing, you've got a chance. Coming in and having a clean slate was my biggest non-negotiable—having the ability to come in and really affect change. We've got to set standards. We've got to build this thing from the ground up and have a really solid foundation. Equally, getting ownership to understand we're going to have ebbs and flows, but we need to maintain course.

We did that this year. We started with a new coach, a new assistant coach, a new sports performance director. We had a new athletic trainer. More than 50% roster turnover. We got a new groundsman. You name it, we did it. From that standpoint, some would say that's somewhat risky because there's no continuity. My viewpoint was it hasn't worked for the previous three or four years. So, it's a little bit the definition of insanity to just keep doing the same thing.

We went for it. We were backed fully. We stayed the course. We went on to win the club's first trophy, which is the Western Conference. That was really cool. We lost in the final in shootouts, which is disappointing, but at the end of the year, there were a few times where you get a little bit emotional up in the box watching everything that went around. I remember the semi-final and final when the anthem was playing. If you go back and look at all the work you've done and how the crowds came—we were sold out. There were no more tickets left. The whole city got into it. We saw more jerseys than you could poke a stick at and the city really backed us. That was a moment where you reflect and say, regardless if we win—of course, the competitor wants to win—we've made a difference and the decisions we've made throughout the year, this is a consequence of that. Lucky for us, it was on the right side of good.

Matt: Congratulations. That's meteoric in terms of success and rise. I have two things I want to get back to before I forget. I'm only a casual football fan, but I know you're a goalkeeper. What's your take on shootouts?

Caleb: Well, this year I hate them because we lost. But look, that was something that I enjoyed. You can do homework on it. Trying to put that into another American sport... maybe baseball. I'm sure there are some data points for high-pressure moments—what's his go-to ball. For us, we look for patterns. You'll see players write that on their water bottles. I used to look for patterns and figure out: you're a big-game player, you might want to change it up. Or he's a rookie, he's not changing it up, he's going with what's comfortable.

I came out probably more on the good side than bad in a shootout. I think some people just have a knack. You can't really coach it. You kind of smell which way and you end up going that way. That worked out for the most part for me. But for the club this year, we lost two penalty shootouts throughout the year. So, that was not fun. You just got to be lucky.

Matt: Knowing your track record with shootouts, it's no surprise you have a strong track record with taking on challenging situations and coming out on top. It's just a crazy amount of pressure though, given that you play all that time and now it's basically you and one guy and that's it.

Caleb: I think the fans enjoy it. The players and staff say it's a terrible way to lose. I agree in the sense that I'd rather just lose straight up and I can accept that. But on the day, we didn't concede a goal the whole playoffs and yet we lost the final. That's life. Someone had to do it. Unfortunately, it was our turn this year.

Matt: It isn't always fair but it is what it is. Two of the other thoughts as you describe that process of taking FC Tulsa to the championship stage resonate with me and what we're working on and hoping to solve at Bonsai.

You mentioned the ownership wanting to win and that being really critical as you made a bunch of changes. I think before we got into this aggressively at Bonsai, I took for granted the idea that if you're running a company, you must want to achieve your goals, to succeed, to win. I wouldn't say people don't like success, but I have a bigger appreciation for the difference between a team or company that is looking to just keep the lights on versus that mentality of saying, "We don't need to keep not winning championships here. Let's look at what we need to change."

The businesses that work with us, if you are working with our platform and our team, you're likely doing something very differently than you used to do it. That paired with someone who is making change with a goal in mind of overachieving or succeeding works really well. What we're doing is probably not a great fit for people where achievement at that higher level isn't something they're really passionate about and they're not willing to make those hard decisions.

I imagine the things that you wanted to do and then saw success with... you had the backing of ownership. But it wasn't like you came in, made changes, and saw an undefeated season from the very beginning. There had to have been periods where you asked, "Caleb, how do I know this is working?" Once you had buy-in from those stakeholders, how did you approach or what did you look for as measures that you were on the right track?

Caleb: I think you hit it—the word you used there a lot was "change." I think what you'll find in organizations—companies, sport, can be anything—is that very few people are comfortable with change. Everything is a resistance to change. That's why they've got a bazillion different change models.

Change without a purpose or a "why" is even more difficult for your employees to get involved with. First, understanding what the change is and why we're doing it, and communicating that is key. In my case, it's illustrating that to an ownership group and then I went back down into a technical staff and said, "This is why we're doing something. Here's what we need to be doing." Equally, giving the staff a voice to be part of that process. Allowing the employees to have a voice creates that buy-in and wanting to win those challenges.

That for me was really key as an immediate measuring stick. Who's going to get on board? Who wants to be successful and who's happy just doing what you've always done? If you're just happy doing what you've always done, the results have spoken for themselves. I don't want to be associated with average. I want to be associated with excellence and setting standards. But I need a team that wants to do that with me.

Then we moved into what that's going to look like from a front office standpoint. What is the vision? Where do we want to be in three or four years? I think a lot of people just bring someone else in to fix it. You can't just figure that out; you need to know where you're going. That's where strong leadership comes in when things aren't going well. How do we maintain the course?

In Memphis at a previous club, we lost five games in a row to start the season. I remember the coach coming in going, "You're probably going to have to move me on at a certain moment." I said, "That hasn't crossed my mind. Have you looked at the data?" He said, "Yeah." I said, "Well, all the data points that we care about... we were overwhelmingly winning those battles from a data viewpoint on the field."

Thinking long term, that's who we want to be. That's what we set out to do. We are achieving that. The results aren't speaking to that today, but over time with consistency, the data says we're going to be successful. Instead of just changing because "well, that didn't work," which means you don't have an identity, that data was a clear indicator that we were going the right way. We just needed to stay the course. This year we had similar. We use XG and XGA (Expected Goals and Expected Goals Against).

Basically, it's the differentiator—the ability to score more goals and concede fewer goals. Very basic, not overcomplicating things. We won those battles on a weekly basis more often than not. That was a metric that we thought would take us somewhere towards a championship and evidently, that was correct. But you have to build to that over time.

Matt: Could have been maybe an example from Memphis or Tulsa... Were there any periods that stand out to you as inflection points where you saw people really started to get what you're preaching?

Caleb: The biggest thing we tried to do was establish non-negotiables in our DNA and how we're going to work. In the front office, it was: don't be that guy going down the stairs at 4:45 waiting in the car park. If you got work to do, let's do it. Let's be awesome and let's set a standard. If you've done your work and you can get out of here earlier, go and do that. But I put on a PowerPoint early in the year: Ask yourself, is this my best work? If the answer is no, then you're not doing yourself any good and you're definitely not going to be part of a winning team.

Downstairs we said to the guys, our culture is going to be work rate. We got to start with work rate and we got to start with honesty and taking on direct feedback. Our group was phenomenal. When we saw the levels of training and them beating down your door for feedback... when you listen to them say, "Hey, I can't wait for the 60th minute in the game because we're going to crush them," that's a byproduct of how we're training. Those culture pieces are equally as important as our data points. When we hear that, we knew we had buy-in from the company. It snowballed week on week. In the end, I don't think the boys cared about any data points as much as we did. They just felt as though we're all in the same boat going the right direction. Change at that point was not really a conversation.

Matt: The thing I take the most from playing sports into trying to do anything of value with our work has always been that idea of working towards something that's really hard. When you're working on something really hard, it's defined by the fact that you're not going to succeed all the time. If everything you did was just always great, everybody would do it. It's easy.

We can't want to do really important, amazing, hard things and then always succeed all the time. In sports, people who really succeed start to turn that corner of being okay with the journey. The feedback might feel like I'm failing, but I'm getting better all the time. That's such a powerful mentality.

It's one of the hardest things we do in the technical work at Bonsai. What we're doing very differently with these organizations is helping expose through data that there's quite a bit of "not great" going on. How fast can you get okay with that? This doesn't mean we're all fired. This is an opportunity.

You mentioned the culture being as critical as the metrics. When we see the culture come along, it's wild. Suddenly all these things get better and people find it fun and appealing to actually go after being best as opposed to where they were before.

Caleb: When you're talking about having the change within the organizations, I think naturally when you're spelling that out for people, saying "this is where we feel like the gaps are," if you say "this is where we failed," people get defensive. We say there's an opportunity for further success here in this area. How are we going to do that together? When you illustrate that and people drop their guard and aren't resistant to change, you can do that.

I think that goes across all businesses. I love these types of conversations where it's not just sport. Most places fail because they don't have an identity. Their culture is not very strong or really enforced. Therefore, all these technical metrics that we're setting and trying to achieve... I call them fluff because you really don't have the group behind that to go and achieve those goals.

Matt: You mentioned also the process and the amount of time it takes to see those end results. Are there any watch-outs or mistakes that teams that you compete with make that we should all avoid?

Caleb: Money. People feel that money can just fix it. "I just throw money at the same thing that I'm doing. It's got to get better." If I just keep going down the same track and I keep putting money, eventually I'm going to buy my way to something successful. I go back and say: is it money well spent?

If you don't have a system, a structure, a way of working, or the DNA—it ultimately comes back to the culture piece again—you're just sticking band-aids on the cracks. Who are we? Who are we going to be? What is it going to take to get there? And then remaining consistent.

I think a lot of people think for a season ahead, 12 months ahead. I think ultimately you need to be looking three, four years down the line. What are the trends? What is likely to change? Are we factoring that in? And then working to achieve those results throughout. If I just keep doing more of the same, eventually I might get lucky. We can all go to the casino; if we play long enough, we're probably going to win, but that doesn't mean we haven't lost a million dollars beforehand.

You've got to have a little bit more foresight. Make sure everybody in your organization is on the same page. Otherwise, if people just want immediate success today and they don't understand what you're building, then you start losing traction. You just spin your wheels and you're in this cycle of people doing their own things. We're not winning, we're not making success, and we're just spending a ton more money. Ultimately that leads to people out the door.

Matt: Now that you've taken FC Tulsa to a championship-caliber place, are the long-term goals and short-term goals changing at all? How are you messaging those to your team in 2026?

Caleb: It's a really good question. I reached out to a friend that played in the Premier League about a week ago. I wanted to pick his brain on: when you won at the highest level and you come back next year for that all-team meeting, what was different?

He asked me what I thought. For me, it was: you've got to have a new way of adding to your strengths. But your DNA and your culture, if you get that right, that's your foundation. As we build moving forward, we're obviously going to go to ownership to see how we can help make better decisions—whether that be through data platforms, player budget, or infrastructure.

That's always a challenge: once you've had success, how do you build on that? But I'm a big proponent of being consistent and staying true to who we want to be. For us, that's building over three to four years to be a perennial contender. Not having the biggest budget, ideally not the lowest budget. Making sound decisions while understanding our identity. That makes the clarity piece come through a lot easier. We know who we are. We'll wait for the right moment. We'll get better at what we're good at and we'll try to make sure that our weaknesses come up a level.

Matt: I love that answer. That foundation, the process that got you here, that's going to be the thing that takes you to hold up the trophy the next time.

I have one question I feel like I got to ask. The other area where sports and what we do intersect almost perfectly is the competitive nature. Your league and many others are hyper-competitive. But not everyone can win the championship. There are consequences for leaders that happen fast when your teams don't win. Coaches are sacked, organizations change entire staffs.

In business, the Chief Marketing Officer (CMO)... I believe it's the shortest average tenure of any C-level across broader companies. I've heard estimates as little as 18 months. It is as hard a job with often as few resources as any C-level job.

Do you have any advice for this group? The CMOs at large. They're in a very competitive game. Is there anything you'd tell them to take into 2026?

Caleb: The biggest thing for me is those executives have to understand you need to build a really driven team. That will ultimately help you outlast those 18 months or two years. It's the same in our industry. Coaches are at 18 months to two years before they're sacked. My roles are around about two to three years before you're sacked. We get judged on results on a weekly basis.

The number one thing is communication. Make sure that when you have your team, you're clearly articulating what it is that you're trying to achieve. And who are the stakeholders that need to come to the table so that you can make sure that the first time you're failing isn't the first time they're hearing about it?

I think a lot of people in executive roles don't want to stick their hand up and ask for help because that could be a sign of weakness. I believe the complete opposite. Get your team together, get around the table. You guys together will come up with a plan that is way more compelling than just any individual.

Then when it comes to your success in getting results for a customer or for an organization, they need to be communicated to effectively and on a regular basis. Where are we at in this process? Where are we going? Would you like a voice in this conversation? Otherwise, it gets back to: "I don't know the struggles, I don't know what you're going through, I don't know what you need. So, out with that guy, in with a new guy."

Matt: You brought up encouraging people to bring their voice to that conversation. Do you feel like that builds trust?

Caleb: 100%. Trust is kind of like the culture word. We talk about it, but we don't truly know what that means at times. For me, trust is: I can trust that person to come forward, good and bad. I can trust that the information I'm getting is proven because they can show me where that information is coming from. Ultimately, when you've got a leader that is open to different ways of working, I can believe that my staff brought me that idea and we're going to run with that because I feel like that's a better idea than I've got.

Matt: You're building that driven team. If you could only pick one thing, is there one trait you'd look for to tell like, "Hey, I think this person's driven?"

Caleb: Work rate. That's a non-negotiable. As an athlete, in a boardroom, whatever. You've built a business and you know that you've been doing hours of work where people don't see that you're in a room, your kids are asleep, and you're working away. That is what it takes to be successful.

There are so many people that want to paper over work rate. "It's a new platform or new this." There's no substitute for people that are going to turn up early and leave late and get the work done. Those employees are worth a bazillion dollars.

Matt: A lot of times even in technology, the thing that ends up changing your business might have been a product that took 10 minutes to code and launch. But what people don't know is that 10 minutes only happened because of the five years of failure or the 10 years of work together—the corpus of that work rate. That's what makes the magic moments. You don't get to just do those moments. You have to do the other things too.

Caleb: You get paid for the 95% of the job. The 5% of the job that you don't like is ultimately where your end is going to come through. The cute stuff, the proud moments, all that is a byproduct of the shitty work that people don't see that you're doing. I don't think there's any substitute for that, whether it be more investment or whatever. If you've just got poor work rate, ultimately you're going to fail as an organization.

I did have one question for Matt though. You were talking about when you go out to people and show them this is where your gap is, this is where you're not performing. How do you get them on board? Obviously, you could be speaking to an owner where he takes that personally. They don't want to hear that. How do you level that to those people that perhaps would take that as a personal shot?

Caleb: Great question. I'll give you two answers. One interesting thing in our world is that there are times when say the owner or the CEO is involved in that early conversation. What might be surprising is actually those are the easiest ones.

So you're onboarding our platform. It shows lots of things that need improvement. If it's the CEO, they definitely don't know what to do, but in their mind, they're like, "Hey, we've hit an inflection point. We have to make a change. I don't know where it hurts, but I feel like something hurts. Someone make it better." In many respects, you're almost that doctor giving a diagnosis. There's almost this excitement over the bad news.

The folks that have a far harder time hearing that news are the marketing team. Oftentimes it's more than one person, or their agencies. A lot of times it's not that they don't have a good strategy and that the CMO isn't smart. If their plan had been realized in practice, frankly, it would be working. It is unfortunately, through no one person's fault... essentially a data issue. In marketing, we have a lot of data that isn't even close to as good as XG. And it dresses up in many costumes. Many times that data has been on a scoreboard that people genuinely thought was right. They are getting an insight for the first time that it has one or more fundamental issues. That switch is very jarring because what you're telling people is, "Hey, the world you thought you were living in is a lie."

There's the whole "don't shoot the messenger" phrase. I joke about it as the "trough of disillusionment."

You typically bring Bonsai in, everyone is excited: "We need a change, we want to win." You get that first view and you hit that initial period of, "Oh my god, okay, there's a lot of bad here." Peers of Bonsai, both service providers and technologies, tell a fancy-sounding story. Clients genuinely think that part of the deal in measurement is that it's going to tell some rich rosy story.

Then they work with our product and there's no rosy story in the beginning. This is where it gets ugly. They think, "Man, this is not what we paid for." Can you get through that initial phase? Can you be like, "Remember why we started this? We all agreed we wanted to compete and win."

That was the hard news. We can get through it together if we trust each other. Can we convince them through our products and our team that even though we might bring bad news, we couldn't be more on your side of the aisle? This is not about "you're wrong." This is about "can we work together and pull this back where it needs to be because we believe in you."

When that happens, it's wild to watch. It can happen within weeks and months. I always joke, "Month three is going to be your hardest month because you're going to hate our team. But if you get to month four without killing us, I think you're going to really be excited."

Caleb: That's interesting.

Matt: Well, I learned a lot personally from this, Caleb. I appreciate you coming on our podcast and I hope folks found this insightful. Where can we find you guys next year? Tell us about the team.

Caleb: We kick off in March. We have our first match away in Sacramento. The games are broadcast on ESPN or CBS. Preseason starts January 15. So it's a short turnaround for us. But yeah, we're back at it and hopefully, we can go one goal further than we did this year and win a championship.

Matt: Cheers. Let's see a title in 2026.

Caleb: That's the idea. Appreciate it. Cheers.

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