Jared Solomon - Co-Founder and CEO of Five Iron Golf

Colbert Cannon: Welcome to Season 10 of the HPScast. I’m your host, Colbert Cannon.

If you’re new to the pod, HPS is a global investment firm. We manage approximately $110 billion in assets for a broad range of institutional and retail investors. That capital is invested across private credit and public credit strategies. Each week, I sit down with key relationships to, partners of, and friends of the firm to learn from their experience, ask how that experience shapes their current roles, and give insights into HPS and how we operate.

So, with that, let’s bring in our guest. Our guest this week is the CEO of one of the most exciting concepts in sports entertainment. After undergrad at Hamilton and graduating Columbia Law School in 2011, this gent kept himself quite busy as an equities derivatives trader at several shops while also launching Flux Stables, a poker staking business investing in online and live poker players, globally.

In 2015, he founded Five Iron Golf – the business he runs today – which is a leading indoor golf simulator business focused in dense urban areas. Since its beginning as a single physical location in Manhattan. Five Iron has grown to over 20 locations across New York, Chicago, Philly, Boston, and the list goes on.

Along the way, they took on investment from Topgolf Callaway to help accelerate their growth, meaning this gent has the pleasure of working with former HPScast guest Artie Starrs, Topgolf’s CEO. Our guest is both a successful entrepreneur and executive, as well as a lovely and thoughtful individual, period. So, I’m a fan of both him personally and Topgolf. Full disclosure, I’m an avid consumer of the Five Iron offering.

So, without any further ado, I’m excited to welcome in this week’s HPScast guest, Jared Solomon, CEO and co-founder of Five Iron Golf. Jared, welcome to the pod.

Jared Solomon: Thank you for having me.

Colbert Cannon: It’s great to have you on, Jared.

I like to go all the way back. Where are you from originally? Where’d you grow up?

Jared Solomon: I am from Bucks County, Pennsylvania.

Colbert Cannon: Tell me about your golf game growing up. Did you grow up playing?

Jared Solomon: So, I didn’t play golf at all, which I think has been a key piece of the Five Iron story, honestly. I didn’t grow up around country clubs. I played a lot of racket sports, but no, I had no real golf experience or history. So, when it came to opening a golf place, I certainly didn’t have any of those preconceived notions about golf and maroons and browns and greens to get in the way.

Colbert Cannon: Fair enough. Alright, so you go to Hamilton undergrad. YoYouu study philosophy, tell me about that thought process.

Jared Solomon: So, honestly, the reason I picked Hamilton was there was a casino close by, and I knew that I needed to pay for college somehow. So, I was playing poker at the casino. I was also playing online back then. It was blowing up, which was a big part of the reason there.

Colbert Cannon: Let’s go down that path. So, you’re an avid poker player. Did you literally help pay for college through playing poker?

Jared Solomon: Yeah, my wife, Catherine, who is our Chief Legal Officer now, we went to Hamilton undergrad and Columbia Law School together. And yeah, I’m proud to say we paid for most of all of those educations through poker, poker coaching, and then starting a poker staking company, which was honestly, my first entrepreneurial thing that I really did.

Colbert Cannon: Amazing. All right. So, we’ll get there to talk about that business, but first, you end up going to Columbia Law School. Did you think you wanted to be a lawyer, or why was law school the right choice?

Jared Solomon: I went to Columbia Law School thinking that I wanted to be a sports agent without really understanding that everyone who goes to Columbia Law School ends up going into corporate law. It seems my wife, Catherine, went to be an environmental lawyer. She ended up in litigation. I ended up on Wall Street. So, we didn’t really have the background. We looked at different schools, and Columbia seemed like a good place to end up. I don’t even think I knew the difference between litigation and corporate law at that point. It was, sort of, we liked studying for the LSAT together, but you take some tests, and you, kind of, go to law school, and that’s how it started.

Colbert Cannon: Well, it all worked out. All right, so let’s talk about your early venture, Flux Stables, which, you mentioned, helped pay your way through law school. Flux Stables is in the business of poker staking. Tell me about that business.

Jared Solomon: I honestly got lucky. Like, I’m not some talented, savant poker player that people sometimes would like to think – at least my mom and dad would like to think – but I got in early. Poker was booming, and I had just played more online. I was sitting online, playing poker, honestly, for free way back in the day, and one thing leads to the other and then poker booms and all of a sudden I was just well-situated to take advantage of it.

Then, from there, I started coaching people and realized quickly that some of the people that I was coaching could end up being good players if they had the right amount of capital. So, then I started giving them capital, and then one thing leads to the other, and we brought on some other coaches and some other management. And then all of a sudden,  you have 200+ poker players across the world, all with individual contracts, all with individual wants and needs and whatnot. So, that was, kind of, a wild ride back in the day to get things started for me.

Colbert Cannon: So, to be clear, you’re giving them money to enter into a tournament, and you’re taking some split of the economics between you and them.

Jared Solomon: Correct. And it was so formative for me because every person was different. Everyone wanted something different. And it just made you work through some of the negotiations and understanding in a negotiation really what people want and what you can do for them. And that was really what it was all about, trying to get these people and make them happy and teach them to be better poker players.

Colbert Cannon: I would imagine that combined a passion of yours as well as you need legal perspectives to be able to get that, right? I mean, I imagine the law degree actually helped in all of that, yes?

Jared Solomon: Not really, I would say. I think that it helps in terms of problem-solving and thinking through things, but what helped was just doing it a bunch. Like, you talk to one kid who needs this and another one who needs that, and all of a sudden you’re just getting a lot of reps at it, which I think is something I feel strongly about, about many things in life. And then, by the time you were negotiating the deals for someone who was playing in the World Series of Poker, who was playing the highest limits games in the entire world, you had a feel for what you were doing.

Colbert Cannon: That’s right. There’s a learning curve there.

Okay, so, you know, not a lot of law school grads, in my experience, end up as equity derivatives traders. But you came from a poker background, so I think that probably tracks a little better. How did you end up in that line of work post school?

Jared Solomon: So, I go to Katten Muchin Rosenman for my Summer Associate gig, and I had a great mentor, this guy David Kravitz, who is a partner there today. And we were working on a deal actually for a casino in Vegas, and I just really liked being on the business side of it and not the legal side.

I talked to him. You know, he did the whole thing of: “You don’t want to be a lawyer.”

I reached out to some poker buddies who said, “Hey, my wall street firm is looking for options traders.” I had no idea what an option was. A call or put made no sense to me, but I took the chance, gave up the big first-year salary, and I just went to a small firm and started trading equity options on the market-making side. And that was really how I got into Wall Street from there.

Colbert Cannon: You mentioned that reps are what you need. How do you learn something you don’t know? Like, you didn’t know what a put and a call was. How do you figure that out on the job and get thrown in the deep end like that?

Jared Solomon: Well, the first couple months, I just played video games and went and got staples of New York food for the traders. And then that led to, hopefully, some late nights and some extra discussion about how it worked. A lot of practice. I, sort of, had the mind and it almost sounded silly to me that this Wall Street finance world could be so similar to what I was doing playing poker, which I felt like was a game. But I honestly can tell you it was exactly the same.

That being said, it took me a long time to learn. I take a long time to learn things in general. Once I do, I like to feel like I can use that to my advantage, and I feel like I’m pretty good at that. But there were certainly points where I questioned, man, was this the worst decision of my life?

Eventually it went well. I think I did a pretty good job. We ended up spinning off and starting our own firm with two people that I had worked with there and ran that all the way through COVID, honestly, before I left to go be the full-time CEO of Five Iron.

Colbert Cannon: And before we leave your poker experience, I would be remiss if I didn’t recommend for our listeners that we did a podcast with Annie Duke. And if you’re interested in behavioral decision-making and poker, there are few people on the planet who are more interesting to hear about all of that than her.

Okay. So you’re working. You’ve got your equity of derivatives gig. I know the story a little bit, but let’s go back to 2015. How did the idea to launch Five Iron come about?

Jared Solomon: So, this is post law school. My wife is clerking for a judge in upstate New York, in Rochester. I am in New York trading options. So, for two years, I’m seeing her every other weekend at best, honestly. So, I started playing ping pong at this place called Spin. I loved it. So, I spent a lot of time there, and I started taking lessons with this guy Mike Doyle in the back of a men’s clothing store.

I was taking golf lessons from Mike, and I was also taking table tennis lessons at Spin. But I was seeing the team-building and the corporate events and everything that was happening at Spin, and that, sort of, “eatertainemt” word was getting into the back of my mind. And I was falling in love with golf. And back to the poker and learning that way. I like the data and the analytics. And I was learning golf on a simulator, and that was just such an exciting way for me to learn the sport that I fell in love with it.

So, that was when we got the idea to, kind of like, let’s go do something together.

Colbert Cannon: When you’re sketching that out on a napkin, what was the early plan, Jared?

Jared Solomon: So, Mike and I both liked eating and drinking and going out in the city. We both, kind of, have a love for hospitality, as crazy as it sounds, and customer service. And I was also seeing what was happening with people not wanting to go to bars, and even from the trading days, I was tired of brokers saying, “Let’s go to a steak restaurant.”

Mike was still busy teaching lessons, and he had other students as well who wanted to practice. So, the original idea was that we wanted something that could serve as a place to practice, but also, we really love this hospitality, food and beverage element of it. And to this day, that really has remained pretty true, where we focus a ton on the serious golfer as well as the entertainment, the vibe, the design.

Then we realized we needed someone to go actually figure out if this idea could work. You have to go look at real estate, you have to figure out permitting, zoning, and all of the million things to actually start a business. And that’s where Katherine, my wife, said, “Hey, my friend Nora – her husband’s in business school at Darden. She’s looking for some things to do. She loves this idea.”

Nora comes on and really is our everything at the beginning. So, it’s me, Mike, and Nora, who’s the only, sort of, full-time person working on this. And then Katherine, at this point, is working at Paul Hastings as a lawyer. That’s the founding four who start the company, and it all, kind of, snowballs from there.

Colbert Cannon: Jared, what was your first location? Where was it?

Jared Solomon: So, Flatiron. Our name, Five Iron, is from the “Five” for Fifth Avenue, Iron from the Flatiron District, and our first location is on 19th and 5th in the Flatiron District. We had four simulators. And you’ve been there. It’s not the Ritz Carlton when you go up there, but at the time, it really was pretty revolutionary for what we were doing.

Colbert Cannon: Let’s unpack that because your hospitality point, I think, is a really important one. I know plenty of golf pros that are really good teachers but don’t get the other aspect of it. And there’s plenty of places where you can go swing a golf club, but there’s nothing else, sort of, around it.

How did you guys marry those two? Because, I think if you think about a special sauce for your business, I do think it’s around the combination there, right?

Jared Solomon: It was just something that we both felt so strongly about, and I think that’s because we both wanted it, right? And this was before the time of Grow the Game or even Topgolf blowing up. It’s not like we had a mission, vision, or values. We really just wanted good food, and we had talked to our customers, right?

Even back then, we knew it was important to talk to our customers. So, we had talked to all these people that Mike was teaching and asked them, “Would you come hang with your buddies?”

I’m like, wait, that sounds like the greatest thing in the world. So, enough people say that, and you, kind of, put your chips in and say, “Let’s take a chance!”

Colbert Cannon: Every entrepreneur I know tells me you learn more from your mistakes than from your successes, in particular early on. What were some mistakes you made early that you carry the lessons with you on forward to today?

Jared Solomon: Oh man, I made so many mistakes, and I’m honestly happy that we didn’t know what we didn’t know back then. But, our first location, we didn’t check the zoning and the permitting the way that we would now, because you don’t even know that is a real thing. So, we knew we needed a TCO – a temporary certificate of occupancy. You need the TCO to get the liquor license, which is obviously a key part of our business. And, we thought, well, of course, we’re going to get the TCO. Well, we find out that is not true. So, we’re starting at the beginning thinking, oh my God, the thing that we wanted to do never even gets started. And this is with Katherine, who is a lawyer, and Nora, who is a type A personality.

The only way that it was resolved was because Nora and Katherine went down to the city buildings department, and they looked at what they call sandscript with a magnifying glass. Like, these two just would not give up, and they found this document. I kid you not, it was from 1825 or something like that, the OG of the city, that is enough to bring to this guy Bruno in the office department, who is completely dead inside and does not care about anything that we’re saying at all. And that’s how we end up getting the TCO, which gets us our liquor license.

Colbert Cannon: I do think that tenacity is needed. Like, every entrepreneur I know, you have to break through something early on, and that’s incredible. The business doesn’t really work if you can’t have a beer while you’re there.

Okay. Tell me about expansion. So, you have that first location. You decide then, obviously, you’re going to continue to grow. How do you pick a new location? What’s the right Five Iron spot regardless of what the city is?

Jared Solomon: It’s more of an art than it is a science. We have all the data now, and all of the history of 25+ locations. But the way it happened was – and remember, this is before I knew what private equity was, before I knew what EBITDA was or anything like that – so, we are sitting there, feeling like we’re on to something. It’s the same core four people. We’re sitting in the kitchen of our Flatiron location, which is extremely tiny. And I just, kind of, said to them, look, we have a pretty good, I don’t know about annuity, but something that we could just pay ourselves out on. And I feel like this is going to do well. Or do you guys want to do something big? Everyone unanimously said, like, screw it. Like, let’s do it. Like, let’s open a second location. And we open our second location in the financial district, I don’t know, a year later. It has 10 simulators that is pretty immediately successful.

But again, there was no magic to find it. We thought, I don’t know, it’s pretty far away from Flatiron. And I had worked on Wall Street, so I felt like people were down there and might want to hit some golf balls.

Colbert Cannon: So, you continue to ramp. You continue to grow. You took on investment from Topgolf Callaway.

So, for those less familiar, Topgolf is more of a suburban driving range offering, and Callaway is obviously the club manufacturer. They are one public company.

When you consider bringing in outside capital, what did you consider? What was important to you, and why were they the right partner?

Jared Solomon: So, I met Chip Brewer. CEO of Topgolf Callaway Brands, and he actually came to meet Nora and me. We toured our Philadelphia location. When someone like him comes calling, and you’re this scrappy startup, you just say yes and try to figure it out. The opportunity to be part of that ecosystem and learn was really important.

The capital is really important. We’ve gone through multiple rounds of private equity. We have a strategic investor. The core four people that started this company, that have, in some ways no business being here, myself included, as the CEO, are still here to this day.

I knew that I didn’t have the experience that other CEOs had. So, getting to leverage Chip or even someone like Artie Starrs, who is the CEO of Topgolf, has been incredibly important to me to go from entrepreneur to actually being a CEO. The roles similar, but, in some ways, wildly different and something that I have really prided myself on.

So, when Chip comes along and you get to leverage his experience and knowledge and being able to call him, it’s such a cheat code in terms of getting to those goals.

Colbert Cannon: That’s an interesting comment. Being an entrepreneur and being a CEO are different. Why? What’s different about that role?

Jared Solomon: I think, as an entrepreneur, you are just excited, and it’s go, go, go. And I would say what’s different is you don’t need a lot of inspiring at the beginning. Everyone there is inspired and wants to take chances and wants to AB test before you know what AB testing is because you’ve never read a book on business/ You’re just going for things and trying things because there’s not a lot to lose, and you don’t know what you don’t know.

Now, as a CEO, I think it’s more about how you instill entrepreneurial spirit on a group of people who might not have that natural instinct to be an entrepreneur. You’re managing a thousand people and systems and processes. So it’s just a wildly different experience. And then dealing with debt and investors and board meetings. There’s just so many different things that you’re dealing with that are just wildly different.

Colbert Cannon: And as you say, you know, the fact that your starting four are still there is a real testament to you guys all growing into those roles so well together.

Talk to me about the challenge of – when it’s the four of you in a room, everybody’s doing everything, and you’ve got a very tight control over it, to then having to delegate. You’re managing a really large organization now. Talk to me about that transition and how you make that switch over so you’re not doing everything yourself anymore. How do you manage that delegation?

Jared Solomon: Sure. So, for context, you go from closing at Flatiron, our first location, spending the entire day together. The four of us are eating McDonald’s, having a drink, trying to relax, just trying to come down from this battle of customer service. And you just know these people so well, and you just know that they have your back at every single moment. Then you have to figure out how you delegate.

I don’t know if I read this somewhere – someone said it – but it’s like, A people hire A people, and B people hire C people. I think that we got really lucky that our next set of people, which many of them are still at the company, were really, really good. And that gave us some faith that we could delegate and grind and be with them.

Colbert Cannon: Let’s talk about the future then, Jared. As you say, you’re up to 25 locations or so. What’s next? What’s the future for Five Iron that gets you fired up each day?

Jared Solomon: Yeah, so a couple of things. One, I like to remind people of this because sometimes people say, oh, you started this conservatively with these four simulators and Flatiron. At the time, putting graffiti on the walls and four simulators was actually a pretty big deal. And having food and beverage and the kitchen – no one did that. And I don’t want to lose that entrepreneurial spirit. And I want the next version and iteration of Five Iron to be that much better and that much more unique.

And then franchising is something that we’re really excited about and nervous about, too. We did it out of people saying like, please let me open a Five Iron. Now, we’re franchising domestically, we’re franchising internationally, and we’re still opening corporate stores as well.

We have a 17-simulator location that’s opening in Dubai that has three roof terraces and rooftop miniature golf. It’s going to have a gym. They’re taking what we always believe – we want to be the best place for the serious golfer and the entertainment customer – and they’re just taking it to the next level.

So, franchising is really exciting and, sort of, where Five Iron can go and be different 5-10 years from now.

Colbert Cannon: Are there lessons you can draw from the actual game of golf into your business life? Is there anything you take away from that?

Jared Solomon: I would say that I try to take everything in stride in golf. Like, there is variance and volatility. And there’s variance and volatility in poker. There’s variance and volatility Five Iron and in business. People like to think that they can control all these aspects, and if you just practice more or you just do this or that. And the truth is, you know, Chip Brewer calling is a little bit of luck. And yes, you can say we put ourselves into that position, but it’s a little bit of luck.

You do all the right things, and you could lose. And I think that’s in some ways true of golf, too. You could hit the best shot of your life and hit it on the screws, and then it’s in a bunker. And you’re getting a triple bogey and just not making a big deal about it. Because, if you do the right processing enough, hopefully the results are going to turn out in the long-run.

Colbert Cannon: Yeah, I do think there’s something there about being able to handle failure because anybody who golfs knows that you’re going to fail way more often than you will succeed.

Awesome, Jared. Well, listen, we’re excited to see what’s going to come from Five Iron.

Before we get to the last segment of the pod, I want to do a speed round of questions for you, Jared. I’m going to ask you some questions. Give me your simple answer. First thought, Best thought.

You ready?

Jared Solomon: Hit me.

Colbert Cannon: All right, Jared. Your favorite golf course to play?

Jared Solomon: Sleepy Hollow.

Colbert Cannon: There you go.

Hardest course you’ve ever played?

Jared Solomon: Oh man, Hudson National is sneaky hard, and I seem to score about 110 every time I play there.

Colbert Cannon: Yeah, and the topography gets you too.

All right, given your company’s name, how far do you hit your stock five iron?

Jared Solomon: About 205 yards.

Colbert Cannon: Oh, Jesus. The man can hit.

Have you ever had a hole in one?

Jared Solomon: I have.

Colbert Cannon: How many?

Jared Solomon: I have one, and it was on the 16th hole of Sleepy Hollow in a tournament, and it was a very exciting moment. Decent hole to do it.

Colbert Cannon: I imagine. Your career low round?

Jared Solomon: 76, I believe.

Colbert Cannon: Amazing. Your favorite current club in your bag?

Jared Solomon: My favorite current club would be my new putter, which is a left-handed putter. It’s an Odyssey putter, obviously in the Callaway family, that I use.

Colbert Cannon: Love it.

If you had to recommend some buddy visit one Five Iron location, where do you send a buddy?

Jared Solomon: I would say, if you want the OG feel, go to Flatiron. Grand Central, our newest location, is an amazing spot. Go to Grand Central if you haven’t been there.

Colbert: What’s your favorite single food item on the Five Iron menu?

Jared Solomon: Oh man, anything pizza or flatbread related was the OG thing that we served – the first shareable thing – and to this day, it’s something that strikes a chord for me.

Colbert Cannon: I love it. I will endorse that. They’re quite good.

All right. With that, Jared, I want to move to the last segment of the podcast, something we like to call “Best Ideas.” We offer up something that’s added value in our lives, recently, called Best Ideas, because, as investors, we hope to expose ourselves to those.

Jared, you’re our guest. I’m going to ask you to go first this week. What’s your best idea?

Jared Solomon: So, it goes back to poker a little bit, but I think people conflate that, because a decision might be important, it justifies spending a whole lot of time thinking about it, as opposed to spending a bunch of time thinking about the decisions that you can actually find the right answer to. And even going back to my coaching of poker days, all the players would want to do is look at these really niche 50-50 decisions and just think about them over and over again. And that’s not really where the edge was. The human brain wants to look at these complicated decisions, and people joke with me – sometimes they’ll be like, let’s just flip a coin. At a certain point, you’ve done the diligence and, just need to make a decision and go and learn from it.

Colbert Cannon: I love it. That’s a great idea.

All right. Well then, for my best idea, as listeners know, I like to be inspired by the guest of the week. As you heard throughout this conversation, our guest went to liberal arts college, got a law degree at Columbia, And I was reminded from that set of facts of a biography I read once and loved that tells the truly insane story of a man with a similar background.

My best idea this week is the biography from Nicholas Dawidoff called “The Catcher Was a Spy,” which is the remarkable story of the professional baseball player Moe Berg, who amazingly moonlit as a spy for the U. S. during World War II.

Moe attended Princeton and then had a 16-year career mostly as a backup catcher for teams like the Dodgers and the Red Sox. A true renaissance man, he attended Columbia Law School while playing professional baseball, including one year missing some spring training during a stint with the White Sox given final exams.

He had a real gift for languages, and he spent time in Japan in the 1930s when baseball All-Stars from the U.S. and Japan faced off. And he was able to use that unusual access to film military facilities.

After he finished his playing career, he became involved with the OSS, which is the precursor to the CIA, and he literally traveled the globe during World War II as a US agent. It’s the kind of story that if you wrote it in a Hollywood movie, the studio would say, great stuff, but no one’s going to believe it. And it’s all completely true.

So, in honor of two gents who went to Columbia Law School but took very different paths for their chosen careers, let me recommend the biography, “The Catcher Was a Spy”, by Nicholas Dawidoff as my best idea this week.

Jared, any thoughts on Moe Berg? I don’t think he played for the Phillies, in fairness, but any thoughts on Moe Berg?

Jared Solomon: Phenomenal. Look, anyone that takes a different path and just tries things, I’m always a huge fan of.

Colbert Cannon: All right. With that, it’s time to say goodbye for the week. Jared, it was truly a pleasure to catch up. I look forward to an evening out with you at Five Iron soon.

Jared Solomon: Thank you so much.