James Kline on Banking, PE, Pro Hockey, and Wedding Crashers (A Fireside Chat with Tom Matlack)

Inside the Boardroom: Fireside Chats with Tom Matlack – James Kline Interview

For a lot of Wesleyan student-athletes, the pressure to “figure it all out” early can feel overwhelming. In this fireside chat, I sit down with alum and former hockey player James Kline to talk about why his path into investment banking and private equity looked nothing like the standard playbook—and why that turned out to be a strength. James didn’t touch accounting or finance until late in his junior year, took three years off to play junior hockey, and still found his way into a boutique investment bank and then a sector-focused PE fund. Along the way, he learned that surrounding yourself with good people, being relentlessly coachable, and starting somewhere matter far more than having a perfect résumé. This conversation is especially geared toward freshmen and sophomores who are just starting to think about careers while juggling practice, classes, and everything else. What follows is a slightly edited transcript of our discussion.

This video is part of a summer interview series hosted by Tom Matlack for his Wesleyan University course, designed for freshman and sophomore college athletes exploring business and life beyond sports. Through real conversations with accomplished leaders, the series offers practical insight into entrepreneurship, leadership, and career discovery.

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Tom: Cool. So, I actually don’t even know how we were introduced. Do you remember?

James: Yes. It was through Will Mroy.

Tom: Oh right—okay. And how do you know him?

James: Not that well, actually. We have a mutual friend, and I met him at that guy’s wedding. I think you remember that I went to Wesleyan in ’22, right?

Tom: Cool. Yeah. So, I think I said in some of my messages that we’ve done probably a dozen of these, and they’re generally with my friends. I’m 60—class of ’86—so they’re all a bunch of old dudes. You’re the first relatively recent graduate. I’m sure the students will be psyched to be done with the nursing-home crowd and actually talk to someone they can relate to. So this is great.

I’d like to ask a couple big questions and then drill down on your story. One big question I always ask—and I know you’re only midway in your career—but so far, what are you most proud of?

James: I don’t know if my answer is career-focused as much as life-focused, but honestly: surrounding myself with good people. I was fortunate to grow up in a good family, have good friends, and keep myself around good folks. That’s led me to where I am today.

My path has been more unconventional than most—both in hockey, which was a big part of my life, and in my career. I’m proud of the people I’ve surrounded myself with; it’s helped get me here. Even the Will connection—right? I don’t know him that well, but if you meet good people and they connect you to good opportunities, that matters. I’m happy to be here today because of that.

Tom: So what’s one mistake you made—something you’d tell these guys not to do?

James: I thought a lot about that when you sent the question. Honestly, I don’t know. Every mistake leads you to where you are, and I’ve made plenty. More relevant are the ones on the job. My intent has always been good—I work hard, I want to do good work. Mistakes happen. You learn, you move on. It’s not the end of the world.

I’ve definitely done dumb things at work—answered a question wrong, mis-evaluated a company—but you take the feedback, get better on the next rep. As long as your intent is right, and you’re honest and willing to admit when you’re wrong, that’s what matters. Mistakes make us human.

Tom: Yeah. We’ve talked a lot about growth mindset in class—as athletes, as students, as potential businesspeople. We’re all trying to reach our potential, and mistakes are part of that. How you respond is the key.

James Totally. And to your point—this goes to some of the questions you asked—I didn’t know anything about accounting or finance until winter break of my junior year. The recruiting cycle for banking gets earlier every year. For me to get a banking internship, I kind of got lucky.

If I could go back and start networking earlier, sure, maybe I would have landed at a bulge bracket. But I don’t view it as a mistake—more a learning. The earlier you get in front of this stuff and learn it, the better.

I didn’t land my capstone internship until February or March of junior year—which is late for banking. But I’m happy with where I ended up.

Same with private equity. Most people hit the desk and immediately start interviewing for PE roles. For me, that didn’t make sense. I hadn’t learned anything yet—why start recruiting for a new job already? So I took my time, learned the concepts, understood the impact I was making. And when it was the right time, I made the jump.

It’s similar to my hockey path. I didn’t know I wanted to play junior hockey until late in my senior year of high school. I was planning on going straight to college. Then I ended up taking three years off, playing juniors, and came into Wesleyan as a 21-year-old freshman. If I’d gone to college right away my trajectory would’ve been completely different. If I’d thought about juniors earlier, that would’ve changed things too. All of those “mistakes” are just forks in the road that led to different opportunities.

Tom: These guys are all freshmen and sophomores, so hopefully we’re helping them get ahead of the ball a bit. But I agree—you don’t need to follow the route everyone else is taking. Go your own route, wherever that leads.

I didn’t know you played three years of juniors—geez, that’s a commitment. So you get to Wesleyan—what did you like most? What are your fondest memories?

James: Honestly? Hockey. Huge hockey player and still a huge fan—I still follow the team. That was a big part of my life. But it wasn’t even the games. It was the practices, the bus rides, the road trips. That’s where you get close to your teammates. A really tight-knit community.

For these guys—whatever their sport or club is—that’s where the memories come from. Looking back, it’s never “I wish I scored another goal.” It’s “Man, that was such a fun environment.”

And I worked hard, I studied hard, but I also went out and enjoyed myself—Fountain, wherever. Just having a normal college experience with good friends.

Tom: These guys are basketball, soccer, and rowing—we didn’t get hockey players this year. Maybe you can help us fix that for next year.

And yeah, I was a rower—class of ’86—and my best friends are still my rowing buddies, 40 years later. It’s crazy.

So—what did you learn at Wesleyan that’s been most applicable in your business career?

James: Good question. So I honestly didn’t have the accounting and finance background like I mentioned. There were probably one or two courses at Wes I took, but even those weren’t hugely applicable to my career. Helpful, yeah, but not game-changing.

What was really important was learning new concepts quickly and thinking critically. At Capstone I was an industry generalist, meaning I didn’t focus on any one area. I worked on deals for a healthcare products company, a marketing agency, an alcohol wholesaler—you name it. A bunch of random industries.

To understand what those companies actually do and what matters, you have to learn fast. The industry is pretty fast-paced, the job is fast-paced, and you’re constantly picking up new concepts.

At my current gig at Edgewater, we’re sector-specific investors—specialty chemicals, specialty industrials, advanced materials, life sciences. Those are all super complex industries. I didn’t know anything about them before I took the job. I’ve learned a ton on the job.

I think taking random courses at Wesleyan—electives, whatever—forced me to get smart quickly, figure out what matters, and focus on the critical few. That’s been really important in my career.

Tom: What was the Sabermetrics Club? What the hell was that?

James: Think Moneyball.

Tom: Oh, okay.

James: We competed in a competition at Columbia. I did it one year—junior or senior year. My roommate was actually the head of the club. Super smart guy. He works for an NHL team now and has been pretty successful pioneering a lot of that methodology and thinking in hockey.

Tom: Wow, that’s cool. What is Team Scotty?

James: That was an internship. Candidly, when I was playing hockey, I didn’t want to go buss tables or anything like that. My neighbor growing up—I’d been cutting his grass since like fifth grade—was also my Little League baseball coach. I knew he did something in sports, knew he did well for himself, but I didn’t know what.

When I was playing juniors, I reached out and said, “Hey, I’d love a job for the summer.” He’d obviously seen my work ethic and character growing up, hired me, and I was an intern there for four summers in a row.

They’re an insurance brokerage for Major League Baseball—both life and disability. Life is more on the minor-league side, but the disability side is the coolest. Players have big, guaranteed contracts in MLB. If someone gets hurt, ownership is out a lot of money. Team Scotty helps get coverage for certain players or certain parts of players if there’s an exclusion—basically to protect ownership.

Tom: That’s cool. So it wasn’t for the players, it was for the owners to protect their asset in the player.

James: Yep.

Tom: Very interesting. So you got this internship with Capstone super late. How did you end up getting it?

James: After Team Scotty, which was the summer after sophomore year, I had a conversation with my neighbor, the founder. I said, “Hey, I love it here. I want to come back. But I also feel like I’d be doing both of us a disservice if I didn’t go see what else is out there.”

So I started researching what might be interesting. My brother works in finance—different side of finance—but I talked to him. I’m pretty similar to him, I like to think. I started learning about finance and what that would entail, threw my hat in a bunch of different rings, and junior year I hit the books hard in terms of self-study.

I got a callback from Capstone. The founder of Capstone is a Wes alum—don’t know what class. So that was good networking. And one of the guys on the baseball team a year or two above me, who I was acquaintances with, came across my résumé and said, “Hey, we’ll give this kid a first round.” I landed the internship from there.

Having that connection probably helped, honestly. But once I was in the process, I nailed the technicals, and there are a lot of soft skills too. I’d hammer that home for the guys on the call: it’s not just how smart you are. Everyone at Wesleyan is smart. The question is: do I want to work with this person? Do I want to be in the trenches with them? Do I want to see this guy nine to five—or longer?

The intangibles are huge. You can learn the technicals. Having a good attitude and positivity in the workplace is critical.

And honestly, since everyone on this call is an athlete, I’d say that environment is invaluable. Growing up in a locker room or on a team, some of the stuff athletes take for granted—like, “Of course I’m going to put the team first”—not everyone has that. I don’t think I fully appreciated that until I joined the workforce. That mentality is really important and has been pretty key to where I am today.

Tom: Yeah, one thing we… So we actually spend a big chunk of the course on public speaking and communication, just to get across those soft skills.

I keep telling the guys: if someone comes on campus and they’ve got ten back-to-back interviews, here’s how it goes. One person is a rocket scientist—too smart for the job and will annoy the hell out of everyone. Half of them probably aren’t qualified. So you throw those out. Then you’ve got a handful left, and it’s just: who do I like the most? That’s it. Which one do I want to hang out with?

So your job is to be likable, connect with the interviewer, tell good stories about yourself, have a positive attitude, and connect. The last digit of your GPA doesn’t matter. It’s that intangible part.

So what does Capstone do? I’m not really that familiar.

James: Tom, one more point on that. I led recruiting at Capstone toward the end of my time there, and now I help with recruiting at Edgewater, and you’re 100% right.

Yeah, I look at the checklist—GPA, school, whatever—and that’s important. But at the end of the day, you either vibe with someone or you don’t. If someone has a higher GPA but a bad attitude, it’s not worth it. You’re hiring someone indefinitely. It’s not worth the investment to train them if you don’t want to be around them.

So yes, GPA and technicals matter, and you should hit them. But if you’re likable and can connect, that’s even more important.

Tom: And those communication skills are like a muscle. You have to get a lot of reps in. Out of the box, you’re going to be nervous and not come off great, which is why we’re spending a ton of time on it.

So what is Capstone? I’m not that familiar.

James: Very small boutique investment bank. I worked on the sell-side M&A team—typical investment banking role. Generalist firm, a bunch of different groups.

When I joined as an intern, the firm was about 50 people, based in Boston. Ten-week internship program. I came back full-time. Right when I came back, they were acquiring Headwaters MB, another investment bank. The firm went from 50 to 250 people within my first 6–12 months. Then they were acquired by Huntington probably two years ago.

It was a typical investment banking stint in the lower middle market—the opposite of a bulge bracket—but I liked it better. I still work with similarly sized businesses today: typically owner-operators. Your neighbor could be the one owning it.

As a generalist, you’re engaged when that owner is at a point where they want to retire, take some chips off the table, or find a partner to help supercharge growth. At Capstone, I was involved in the full deal process: pitching to win business all the way through closing deals. You sell, then move on to the next.

Another point: at Capstone you might be working on six or seven deals at a time. The transferable skill there is multitasking. It’s not that different from being a student-athlete: class, homework, gym, social life, practice, competing—that’s a full day.

The job is different—you’re at a computer more—but you guys are already busy, grinding from 8 or 9 in the morning to late at night. That got hammered into me in college without me even realizing it.

Tom: So Capstone… happy to answer their questions. Was your analyst experience similar to a bulge bracket, or different? How much training did you get?

James: A little different. I’d say more accountability, from what I understand. I’ve got friends in bulge brackets, so I’m familiar with their experience.

I got training, but there was also a steep learning curve when I hit the desk. I think I started two weeks after graduating. As a full-time analyst, you’re actually running pieces of deals. That can be anything from administrative tasks to more substantive stuff. How you handle that dictates how you grow. If you dominate the “easy” tasks—organized, detail-oriented—you get more responsibility.

That was my experience: growing in responsibility, having a proactive mentality, saying, “Yeah, I’ll take that on, I’ll take that off your plate,” to the people above me.

So: pretty typical analyst experience. Bulge brackets are a bit different: they may work on fewer, larger projects and can be more siloed. I got a more all-encompassing experience—did a bit of everything, even talking to potential buyers, which you don’t always get at a bulge bracket.

Tom: Was your lifestyle as miserable as theirs, or more manageable?

James: The way I categorize it: I had some long weeks. That’s part of the gig; it’s what you sign up for. I went in expecting it to be worse than it was. But I definitely had some very, very long weeks and nights.

What people don’t talk about enough is that it ebbs and flows. Some nights or weekends you’re fine and hanging out; others you’re really grinding. I didn’t do the bulge bracket thing, so I can’t compare directly. But at Capstone, I worked really hard. It ebbed and flowed, and I had my share of crazy weeks.

Tom: You were there almost four years. What was the most important thing you learned, and what did you hate the most?

James: Most important: be proactive and work hard. I came into the job thinking I needed to know everything—all the technical accounting, finance, LBOs. Meanwhile, some people already knew that stuff and I didn’t.

But honestly, I just worked hard and learned. Everyone in your class is smart and hard-working—that’s what it takes. Be detail-oriented, proactive, good work ethic, positive. Ask questions. People are willing to teach you if you’re likable and curious. I’ve never worked somewhere where the attitude was “You should already know that.” Everyone starts with a knowledge base of zero.

Getting comfortable asking questions and working hard was huge. Also, taking advantage of opportunities: “Hey, you’re the only analyst on this, no associate above you.” Okay, give it to me. Talking to your MD after a deal: “What can I do to improve?” That mentality is straight out of sports. Your coach gives you feedback, you use it to get better. Same in business.

What I didn’t like: I’ve had messups along the way. I’m not perfect. You make dumb errors—wrong email, spelling mistake, numbers off. It happens, you’re moving quickly.

Having thick skin is important. Sometimes you’ll get harsh feedback: “This memo is terrible, redo it, this is burning my eyes.” That sucks to hear, especially when you’re exhausted. But having the resilience to take that, stay up the extra hour, fix it, and show them you’re tough—that matters. It signals, “You’re not going to break me. I’ll keep moving.”

Tom: What motivated you to think about moving over to private equity, and how did that transition work?

James: I touched on this earlier. I wasn’t ready to start interviewing for PE a month into my job at Capstone. It didn’t feel right. Other analysts were doing it, and I give them credit, but it wasn’t for me. I followed my own timeline.

I got promoted after two years. Around mid-2019, I started feeling like it was a lot of rinse-and-repeat. I knew how the job worked. There was more to learn, but I wanted something new. I wanted to learn the other side. You hear a lot about private equity and the buy side.

Also, a lot of my fellow analysts had already moved on—to PE or out of the industry—and I thought, “Okay, now it’s my time.” I also knew PE interviews are technical, and I didn’t want to waste bullets going in unprepared.

Then COVID hit. Obviously terrible in general, but it allowed me to work from home and focus a bit on recruiting without sneaking out for interviews. I got in touch with recruiters, updated my résumé, prepped for PE technicals, talked to some people in the Wesleyan network.

Eventually I got an email from a recruiter: Cleveland-based, sector-specific investing. I thought, “Okay, why not?” My approach is: open as many doors as you can; you can always close them later.

Would I have told you growing up that I’d move to Cleveland? Probably not. It’s not on most people’s list. But I’m from Pittsburgh originally—it’s about a two-hour drive. I wanted to be closer to family.

I threw my hat in the ring. The more I talked to the people, the more it clicked. At Edgewater we talk about “Midwestern values,” but it’s true: they cared about me, my family, my friends. The team is lean, similar structurally to Capstone. Not a huge organization.

I was most nervous about the industries—specialty chemicals, etc. I hadn’t taken chemistry in like 10 years. That worried me. But I knew I had the financial and accounting chops. I met the team, really liked them, went golfing with some of my partners before taking the job, and took the leap.

I’d already taken leaps: three cities in juniors, moved to Boston knowing mostly just the Wesleyan community. So I thought, “I can move to Cleveland. Worst case, it’s close to home, more affordable, and I’ll figure it out.”

Along the way I realized: learning these industries actually gives us an edge. There are thousands of PE funds in North America. Differentiating via industry focus and having real expertise gives you an advantage. I’m grateful I’m not a generalist anymore.

I also didn’t love the idea of a strict “two-and-out” PE model—two years then you must go to business school. I liked that Edgewater offered real upward mobility without necessarily having to do that. So far, that’s held true.

Tom: How big is the firm? How much capital?

James: We have a $330 million committed fund.

Tom: That’s a pretty good size. What’s been the best day on the job so far?

James: Closing a deal is always fun. Our job is to deploy capital and do it the right way. I’ve closed a few and exited one since I’ve been here. Those are exciting days.

But another big reason I wanted to move to PE was getting to work with management teams. On the sell side, you get to the closing and then you’re done. If the deal doesn’t trade, it’s out of your control.

At Edgewater, that’s when the fun starts—when you buy something. Then it’s: “Okay, what did I buy? Where are the skeletons? How do I grow this? How do I operate this company?”

I’m not an operator; I’ve never been an operator. Seeing the inner workings and the levers my partners and operating partners pull to grow these businesses is fascinating.

Edgewater is what I call “the good private equity.” We put more resources in, help grow and scale, and try to do it the right way. Being part of that, learning how to run a business—that’s probably the most fun. Not one single day, but a lot of really good experiences.

Tom: In general, we’ve got student-athletes here who are just beginning to figure themselves out—freshmen and sophomores. What specific things would you tell them to do in the next 12 months to get their act together?

James: Start somewhere.

I’m not going to pretend I never procrastinate. I definitely used to say, “I’ll get to updating my résumé later,” or, “I’ll make a list of people to reach out to at Wesley later.” Just get the ball rolling.

You can keep pushing it off, but then you’ll be kicking yourself. Go have a conversation. Go meet with the career center. Even if it feels useless, who cares? You checked the box, you know what it’s about, and it didn’t hurt anyone.

Open as many doors as you can, then close them later. The Wesleyan network is exceptionally strong. I remember junior or senior year talking to a group, and I was pushed through rounds just because I was a Wes kid who expressed interest and had a good conversation. I had a 45-minute call with a guy at Bank of America. At the end he said, “If you’re really interested, I’ll just move you to the final round. Are you free later this afternoon?” I didn’t think that still happened, but it did.

Moral of the story: the Wes network is strong. We all kind of get it. So just start. Staying still won’t help you.

Also, don’t be intimidated by other schools. You’ll be up against Wharton or Harvard grads—that’s fine. They have a different background. If a firm wants to hire a Wharton kid, they’re going to hire a Wharton kid; that’s not about you. You’re an athlete at a really good school. If they’re looking for that type of person and character, you might be the one they pick over the kid from Amherst.

Focus on what you can control. Don’t obsess over someone else’s head start—five summers of finance courses, dad is an MD somewhere. You’re smart, you have a different skill set, and I honestly think you have an advantage sometimes. In my opinion, accountants can be a little close-minded.

You can learn the technical stuff. Just make sure that when you do get an interview, you’re prepared and you nail it. If you keep the ball rolling, you’ll get opportunities—talks with people at big firms, bulge brackets, smaller firms, consulting, whatever. And for consulting—McKinsey, Bain, etc.—I’m sure the Wes network is strong too. Start reaching out, talk, have normal conversations. Everyone’s pretty normal at the end of the day.

Tom: Yeah, that’s a big part of this course. We’re forcing a lot of reps in that area.

Okay, we’ve got a couple of our brighter students here. I’ll let them ask a couple questions and then I’ll finish with a few.

James: I don’t think it’s a secret—my brother told me this. They’re going to ask you the same questions. How do you value a business? Walk me through a DCF. Those technicals.

Study those for a weekend and nail them cold. At some point in an investment banking interview, you’re going to get asked, “Walk me through a DCF.” I’ve interviewed people who had no idea, like they were shocked I asked it. You know that’s coming—be prepared.

On the other side, be ready to explain how you’re different. Really emphasize the student-athlete angle. I probably had a bias toward student-athletes when I was interviewing candidates because I know what that day-to-day looks like.

Emphasize: “I’m busy, I’m working my ass off, I’m balancing priorities, I’m showing interest in your firm, I’ve got good grades, and I’m likable.” Show you’re well-balanced, can multitask, and can nail the technicals. That’s what you have to do.

Find your “in” too. Tom mentioned reps—but honestly, if you just cold apply to JP Morgan, unless you’re the “perfect” résumé, you might not stand a chance. They may hire some well-connected kid. But if you know someone at JP Morgan—even in a different group—they can put you in touch with the right person, and your résumé goes to the top of the stack.

For Capstone, I don’t know if I would’ve even gotten an interview without the baseball guy. We weren’t best friends. We were just friendly when we saw each other in Freeman or on Fountain. We were normal dudes. That got me a first-round shot. That’s what networking buys you: a shot. After that, it’s on you to sell yourself.

I’d also say: selling yourself is a skill. I like to think I’m pretty humble, but you need to work on explaining what makes you better than the next person. Not cockiness—confidence. You’re selling you. Put it in their court whether they like it or not, but you are who you are.

Tom: Yeah, a couple things to emphasize—for the guys who’ll watch this back—we talk a lot about your personal brand. What’s your story? That’s not bragging; it’s just talking about what’s unique about you. If you have a story that’s actually interesting, even better. Some interviewer is going to be bored stiff. That’s how you connect: a funny story, an interesting story—whatever.

And on banking: I never was a banker long-term—I worked at Goldman Sachs briefly and quit because I couldn’t take it—but all my friends in banking say the same thing: if you don’t have some kind of anchor network into it, you have no chance. So if you’re going after banking, you have to find a way to get to the top of the stack. Perfect résumé with no network? You’re just not going to get a shot.

James: Yeah. There are 30 others like you. It shouldn’t be that way, but it is.

And guys, I’d tell you this too: if you pull up my résumé, most of my interviews have been about junior hockey. “What is that? How does it work?” People want to talk about something different than the standard list of boring questions. Once they realize you’re normal, they relax.

I always made sure hockey came up at some point—organically if possible, or I’d just slip it in and see if they took the bait. Talk a bit about that, and to Tom’s point, likability is a really good quality.

Tom: Oh, if I were interviewing you, I’d be talking about hockey the whole time. That’s what I’d want to talk about, not spreadsheets.

James: Good question—I had the Capstone internship for ten weeks. Going into that, I was actually sold on trying to play pro afterwards. It literally came down to: do I sign this full-time job offer, or do I go try to play semi-pro hockey? I decided I’d probably already lost enough teeth, so I was kind of done.

But on opening doors: I had the Team Scotty thing locked in. I knew if I wanted, I could call my neighbor and get hired in a heartbeat. So I had that safety net.

I took the Capstone internship thinking, “I never thought I’d be an investment banker. Earlier in college I was like, that’s not for me—100-hour weeks, money is everything.” Somehow I ended up landing an internship in the industry.

I told myself: worst case, I’ve got ten weeks to figure out if I like this. If it’s miserable, I can suck it up for ten weeks. I went for it. I took it.

I realized I loved the challenge. The day went really fast. At other internships, you look at the clock and it’s like, “It’s only 10 a.m.?” At Capstone it was, “Wow, it’s already six or seven.” Even now, most of my days fly by. I’m intellectually stimulated, I love learning about new businesses, I like the business owners we work with—they’re normal people. I’ve really liked what I do.

So I’d say: I liked banking, and I really love what I do now. Consulting, I think, is also a really good foundational background for understanding how a business works.

My thought was: if I can understand how a business works, I can do pretty much anything afterwards. Get a job at a business, go into corp dev, whatever. When I took the full-time gig, I thought, “If I work six months and hate it, I can go do corp dev somewhere. I can pivot.”

Consulting can be a great start too, depending on the firm. Venture capital is hard to break into out of school, but if you can get in early, it seems really interesting. I’m less familiar with it.

I’d probably steer away from accounting personally. I find accounting boring. I have two siblings who did audit—one still does—and I don’t know how they do it without going nuts.

Do something that genuinely interests you and that you think will stay interesting. My nightmare was realizing I was bored nine to five. Then weeks would crawl and I’d just be waiting for the weekend.

If you’re someone who just wants a paycheck to enjoy weekends, fine. If you’re someone who wants a job you’re actually engaged by and challenged by, go after that—even if you don’t know exactly what it is at 19. I wanted to play hockey, that’s all I knew. Banking opened a lot of doors for me; that’s why I went that route.

Tom: All right, cool. I’ve got two final questions. What’s your favorite movie?

James: A little older than some of the guys, but I’d go with two: Happy Gilmore or Wedding Crashers.

Tom: Wedding Crashers—I’ll give you props. Very good movie. I love the whole “Mom, the meatloaf!” thing… whatever he says.

James: “Ma, the meatloaf!” Correct, you got it.

Tom: And if you want to leave these guys with one word, what would the word be?

James: Generic response, but the word would be: enjoy.

Enjoy your time. If you have the right character, the rest will come. Yes, you’ve got to check the boxes I mentioned—that’s part of the grind. But truly: enjoy your time at Wesleyan, enjoy your time around your teammates. It’s an incredible place. Some of my best friends today are still from there.

Don’t worry too much about the next step. I never thought I’d put off college for three years to play juniors. I never thought I’d end up in investment banking for almost four years. I never thought I’d move to Cleveland, and I’ve been here four and a half.

I probably thought I’d end up in New York City after school doing something. Instead I ended up in Boston, then Cleveland. Things kept coming and I kept saying, “Okay, let’s take it for a spin.” That’s how I got here. It’s less conventional than a straight path through banking and PE, but I’m happy. I’ve experienced a lot.

I don’t look back and think those three years of juniors “set me back.” Those were awesome years. At the time you’re worried about scholarships and what’s next. Looking back, I’d say: relax, go take a nap, hang out with your buddies, enjoy it. Keep working hard, and it’ll come.

Not to be too lax about the future, but if you have the right mentality and you’re putting in the effort, good things will happen.

Tom: Cool. We’ll leave it there. Thanks a lot. Like I said, this is probably more relevant than some of the other guys we’ve talked to, and it was a lot of fun. Thanks for the time, and we’ll be in touch.

James: Thanks so much, Tom. Thanks, guys.

Tom: All right.

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Other Fireside Chats on The Good Men Project include:

David Kohan on Being Inspired by the Mediocrity of Others

Gregg Stone on Relentless Optimism in VC and Olympics

Kalil Diaz on How to Break Through Limiting Beliefs

Jeff Stevens on Discovering Your Why

Will Thorndike on the Power of Compounding in Investments, Relationships and in Life

Juan de Dios Aguilar on How to Lead, Who to Trust, and Why to Love

Ian MacGregor on Pro Bike Racing, the Secret Drink Mix, Going All In, and Founding Scratch Labs

Tom Macejko on Hunting, Banking, Private Equity, Pulp Fiction and Fulfillment

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You can find the full series on YouTube here:
@FiresideChatsWithTom

Watch for future episodes featuring more leaders from across industries. They all have their own compelling stories and are happy to give advice to the next generation of students, athletes and future business leaders.

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