Jeff Stevens on Discovering Your Why: A Fireside Chat with Tom Matlack

As part of his ongoing series of fireside chats for Intro to Business, Finance, and Life at Wesleyan University, Tom Matlack sat down with Jeff Stevens—an operator-turned-investor and one of the pioneers in the search fund world—for a wide-ranging and deeply personal conversation.

Speaking to a group of freshman and sophomore athletes, Jeff reflected on everything from running the Stanford Band to blowing out his ankle training for an Ironman, and from losing $50 million in equity to ultimately building one of the most respected investment firms in the search space. What made this discussion resonate was Jeff’s candor about failure, resilience, and the power of alignment—not just in business, but in life. Whether talking about building teams, staying grounded in your “why,” or mentoring young CEOs through tough times, Jeff’s insights were a masterclass in responsible leadership.

Interview transcript edited slightly for clarity.

Tom Matlack:
Awesome—welcome, Jeff. It’s great to have you. I’m going to start with a couple of easy questions, then take us into the deep end—sometimes that’s easier.

Tom Matlack (icebreaker):
Who is your favorite athlete and why?

Jeff Stevens:
I grew up in Southern California, and my favorite athlete is Magic Johnson. Those Lakers teams were insane, but even more than that, the passion and joy he brought to the game—and how much better he made those around him—was remarkable. I don’t think any athlete has ever embodied his persona on the court quite like him.

Tom Matlack:
We’ve got some soccer, basketball and rowing fans on the call. As a Reggie Miller fan, I’ll forgive you!. Best sports rivalry ever?

Jeff Stevens:
Lakers–Celtics, hands down.

Tom Matlack:
What’s your recollection of where we first met?

Jeff Stevens:
I can’t remember the exact moment, but I recall seeing your LinkedIn posts—talking about search and entrepreneurship. You weren’t part of that ecosystem, and I thought, “Who is this guy?” Then I remember meeting you at an HBS conference or on campus. Our conversation surprised me—I thought you were super thoughtful. Since then, sitting on boards together, I’ve appreciated how aligned our perspectives are, even though our styles differ.

Tom Matlack:
That tracks. We were outside a session at HBS, maybe discussing a deal where you were an investor and I was on the board—we may not recall exactly. Fifteen-plus years ago, I’d guess!

Deep Dive

Tom Matlack:
Looking back on your career, what are you most proud of?

Jeff Stevens:
Honestly, it’s the relationships I’ve built—and fulfilling my commitments to them. You might hear that a lot, but for me, it’s real. For instance:

My second company: we bought four businesses in two years with $150M (50 equity, 100 debt), and ultimately lost that equity.
Yet 25 years later, 80% of the capital from that deal is still tied up in AnaKappa. Through that tough time, I maintained relationships and credibility. Now those bonds are deeper than ever.

Tom Matlack:
Watching my son, Cole, row taught me that as a parent—and in business—you learn more from losses than wins. You have to show up when things go poorly.

Jeff Stevens:
Totally. I have three kids (24, 22, 21). My greatest joy was watching them in sports—not necessarily elite level, but emotionally, even more intense. No control, all nerves—but unforgettable.

Tom Matlack:
What’s been your most fun—or “best”—day in your career?

Jeff Stevens:
“Fun” comes from alignment—when everyone’s rowing together toward a goal. For example:

We bought a service company tied to oil & gas. Thirty days later, oil dropped from $100 to $50/barrel, wiping out 75% of volume. We faced layoffs, raised prices in a downturn, and lived week-to-week. It was brutal—but alignment prevailed. We bought it for $25M and sold it for $210M four years later. That teamwork made it all.

Tom Matlack:
Your company requires team members to list their strengths/weaknesses. How do you view your own?

Jeff Stevens:
It’s paradoxical—I’m a rule‑follower and methodical, but I take personal risks. I’m clear-headed and not confrontational, but not gregarious—I’d rather talk deeply with a few people than small-talk a room. I’m not creative, so I need creative partners. I’m strong on resilience and structure, but can be closed to new ideas at times.

Tom Matlack:
That explains why our styles complement so well—you’re orderly and steady; I’m chaotic and creative.

Early Life & Stanford Band

Tom Matlack:
Tell us about running the Stanford Band.

Jeff Stevens:
I was a lifelong musician—piano, trumpet, orchestra, jazz—all of it. At Stanford, I auditioned for the student-run band, made it, and eventually led it. I (lightly) joke that it helped me get into Stanford GSB. My job was to push the boundaries—to empower creativity while knowing where the line was. It taught me a lot about leadership, energy and structure on the fly.

Triathlon Era

Tom Matlack:
How did you get into triathlons?

Jeff Stevens:
I’d been athletic since youth—track, basketball, even walked onto Stanford’s football team. Later, I came back to running to clear my head. Then I discovered triathlons—it combined swimming, cycling, running, and added mental challenge. I trained full-time 5–6 hours a day for about 18 months pre-B‑School. I was preparing for an Ironman in Canada—but blew out my ankle playing pickup basketball, tore ligaments, and spent summer in a cast. That ended that chapter.

Early Career Guidance

Tom Matlack:
What do you think about consulting and investment banking as entry‑level roles?

Jeff Stevens:
Consulting—especially—is a great place to learn breadth and skills. But you need to know why you’re doing it. Everything you do, for the next 10–40 years, needs meaning. Understand your motivation behind the decision, and the motivation of your mentors. Find mentors whose “why” you align with—and that matters more than the position or pay.

Mentors

Tom Matlack:
Who were your key mentors early on?

Jeff Stevens:
At Bane (Bain), I worked for Meg Whitman, Kent Taylor (Denny’s), Dick Boyce (Pepsi), Tom Tierney and John Dano at Bain. But the most important mentor by far is Irv Gross, who pioneered the search fund model and has mentored me for 35 years. On a personal level, my parents—high‑school teachers—taught me responsibility to others, and my wife is also one of my greatest influences.

Search & Acquisition

Tom Matlack:
What drew you to the search model?

Jeff Stevens:
At 26, I didn’t have money, network, idea or experience—but in Irv’s class, he said that entrepreneurship didn’t require those, but you needed to manage around the lack. Search is about building that framework, getting into the room, solving problems and improving businesses. My generation—like me, David Doddson, Jim Southern, Peter Kelly, Kevin Twile—were all operator-focused searchers, not zero-to-one founders, and nearly all found and ran companies multiple times.

First Acquisition

Tom Matlack:
What was your first business acquisition?

Jeff Stevens:
I researched extensively—SIC books in a library—to find sectors: business-record storage, home-delivered water, and cable TV. I picked cable and bought several small systems near the Bay Area for $12 M at six times EBITDA back in ’92. We grew the EBITDA to over $3M, then sold to TCI four years later at 10‑11×, achieving a 4× return for investors.

Founding AnaKappa

Tom Matlack:
Tell us about AnaKappa.

Jeff Stevens:
I ran four companies over 20 years (three via search, one startup food business). In 2010, I wanted to run one more company, and two colleagues suggested instead backing emerging CEOs. That led to founding AnaKappa, a private-equity-style firm focusing on the traditional search-fund model. We’ve raised:

Fund 1: $8M
Fund 2: ~$30M (with Ashley as partner)
Fund 3: $80M
Fund 4: $150M (70% deployed)—total $270M raised

We’ve backed over 200 searchers and invested in over 100 companies. Our LPs are high‑net‑worth individuals and family offices—no institutional investors.

Search Evolution

Tom Matlack:
How has the search model evolved?

Jeff Stevens:
In 1985–1995, there were ~10 active searches. By 2005, ~10. In 2010, ~20. Today, there are 250–300 in the U.S. and another 200 globally—~500 active searches.

Spread across geography and schools (not just Stanford/Harvard)
Variations on the model are emerging—some outside its original definition

We’ve doubled down on the classic model: disciplined, thoughtful, conservative. It’s tested by time and our results validate it. Though it means passing on new variations, it keeps our focus clear.

Market & Talent Dynamics

Tom Matlack:
Is there a risk of oversaturation or talent dilution?

Jeff Stevens:
We’re nowhere near deal saturation (150K+ eligible U.S. businesses), so no issue from numbers. But yes—there are more searchers with differing talents and motivations. It’s harder to execute now. Some come in expecting a fast path to CEO and money without the grit required on search and operating sides.

Building Teams

Tom Matlack:
What role does building teams play in your portfolio companies?

Jeff Stevens:
It’s mission-critical. Search funds often acquire founder-owner-operated companies—founders wear many hats. We need to build systems and infrastructure, hire high performers, and professionalize operations to drive growth. It’s hard—especially for first-time founders who’ve never hired or fired. We coach them to use structured approaches and onboarding programs, and help them engage deeply with candidates and new hires from day one.

Advice for Young Athletes

Tom Matlack:
Advice for freshman/sophomore athletes interested in business?

Jeff Stevens:
Figure out your why. At 19 or 20, you may not know exactly, and that’s OK—but awareness of your motivation matters more than seeking titles or money. Do things that get you excited every day, and success will follow.

Fan Q&A: Mentoring on team-building

Tom Matlack (facilitating):
Quinton asks: how do you guide young CEOs in team-building—especially if they’re struggling?

Jeff Stevens:
We put structure around it: job specs, best-fit assessments, onboarding plans, and we encourage use of systems like “Topgrading.” Most often, success in hiring is not just screening—it’s the front-end effort: defining roles, preparing, onboarding. We help increase success rates, but it remains a challenging, ongoing effort.

Final Fun Questions

Tom Matlack:
Favorite movie?

Jeff Stevens:

12 Angry Men—plays to my style: one person asking questions and moving a room
In the Heights—I love musicals, the energy, character dreams and relationships resonate deeply.

Tom Matlack (closing):
If you could leave them with one word, what would it be?

Jeff Stevens:
Responsibility—to yourself and to others. Arthur Brooks (Harvard professor who studies happiness) says true happiness comes from shared experiences, buying time back, and giving—three pillars tied to responsibility.

Tom Matlack (signing off):
That’s a great place to stop. It’s been an honor. We’ll slice and dice this for YouTube in the next 24 hours and share it with you.

Jeff Stevens:
Awesome. Great to meet you all—good luck and thanks!

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Other Fireside Chats on The Good Men Project include:

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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