Meet The Team: Tom Gladden

Fairway Capital Management co-founder Tom Gladden is a people person. He’s easy to talk with, quick to crack a joke, and has a genuine interest in how and why people and systems behave. It’s no wonder many of the world’s most well-known private equity and venture capital managers pick up the phone when Tom calls and give him (and Fairway Capital Management) access to funds other boutique managers aren’t able to get into.
Curious to find out what makes Tom tick, we asked him to share some of his story. Among other things, he talked about how his academic background has shaped his investment style, why he is so passionate about private equity, what he values most about working for a small asset management firm, and why he spends part of every summer living and working out of an Airstream trailer.
How has your background as a history major at Dartmouth College with a master’s degree in computer science from the University of Chicago impacted the way you invest?

As a history major at Dartmouth, I learned about how civilizations, societies, and nations evolve over time.  I came to see that there are patterns to everything and that those patterns repeat themselves. As Mark Twain once said, “history doesn’t repeat itself, but it does often rhyme.” Like the history of humankind, the history of venture capital rhymes. Many of the most impactful companies are formed to commercialize, implement, and/or apply new technologies. There is no Ford without the internal combustion engine, no Apple without the computer chip, and no ChatGPT without AI. How venture capitalists (VCs) find great companies also hasn’t changed over the years. VCs today make money like they always have: by investing in some combination of great people, technologies, and markets. 


My master’s in computer science taught me about the technologies behind many of the innovations VCs are investing in. That background helps me find where opportunities to commercialize and apply new technologies might be. The combination of my knowledge of history and computer science led me to examine and analyze how VCs make money over technological cycles. Over time, I concluded that the opportunity set in venture is always evolving from new infrastructure to new applications of that infrastructure. Each time there is a technological leap (the mainframe, the PC, the Internet, cloud computing, mapping the genome, big data, AI), there is an opportunity to build and apply a new set of technologies. 


What experiences fed your passion for private equity investing?

From the moment I met with a VC firm for the first time while working for the Duke University Endowment, I have been captivated by the private equity industry. It is the most interesting industry in the world. I get to see how some of the smartest people are innovating in every segment of the economy all over the world. It is the ultimate job for someone with an insatiable curiosity about how the world works.


How would you describe your partnership with Fairway’s other four co-founders?

When I worked at Adams Street, four of my colleagues I was most aligned with in terms of investment philosophy were Kathy Wanner, Kevin Callahan, Laura Milligan, and Lauren Bozzelli. We share the belief that the right number of investments should be dictated by the number of good investments available—those with solid return potential. So, it’s no surprise that, years later, we reunited and co-founded Fairway. 


We agreed from the start that the best way to run the firm while having alignment with our investors was to prioritize investment performance over asset growth. So, we have a lower management fee and a greater carried interest than our peers. The better our performance, the better we all do together.


As a professional investor, you’ve had the opportunity to work for both small and large asset management firms. Does size matter?

When you take on a senior role in an asset management firm, you are forced to make the choice between continuing to do the work yourself or managing others to do it for you. The multiple layers in a large organization can cause a senior person to lose touch with some of their investments and the day-to-day machinations of the market. At smaller firms, senior people get to do the investments themselves rather than training and managing others to do them. For me, that's the fun part of this business. I've been meeting with general partners at VC and private equity firms for over 20 years and find the people, their strategies, and their companies very interesting. I want to keep doing that. 




Fairway is based in Chicago. What do you love most about living and working in the Windy City?

Our office is in a vibrant part of town, just kitty corner to the Civic Opera House and close to the theater district, a bunch of great restaurants, and Lake Michigan. It’s a great city and a sports fan’s paradise. Any sport you want to watch or play is here…and the fans are LOYAL!! 


Because of your family’s enthusiasm for sports, you live out of an Airstream for part of the summer. What’s the story behind that?  

With four children at home, my wife and I often “divide and conquer” with one of us “holding down the fort” while the other goes on a college visit or attends an event. Over the last few years, my two sons have played LOTS of travel baseball. So, during the summer, we travel all over the country to tournaments that can last as long as a week. When it is my turn to go to a tournament instead of staying home, and rather than fly and stay in a random hotel, I will drive with one of my boys and stay near the fields in an Airstream. On a hot summer day with a bunch of games, there is nothing like staying at the field in our air-conditioned Airstream with all the comforts of home. So, if you are on a Zoom call with me this summer, don’t be surprised if you see the silver-colored wall of an Airstream in the background.





To learn more about Fairway’s experienced team of PE/VC specialists and their shared investment philosophy, watch our recent webinar.
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