Q&A with Tom Sperry ’91
Tom Sperry has never taken the conventional route. From an unexpected internship at Microsoft that launched his career to founding a venture capital firm dedicated to underrepresented entrepreneurs, Sperry has made bold moves both in business and life. He’s built start-up ecosystems across the country and internationally in the Middle East and North Africa. An ultramarathon runner who recharges by racing through deserts and extreme environments, Sperry is driven by integrity, purpose, and relentless curiosity. He’s reshaping what it means to succeed in today’s business world — one daring venture at a time.
Where did life take you after leaving the Hilltop?
After graduating from Pomfret, I traveled the world and moved to Seattle. I got an internship at Microsoft, where I was a part of the video game group. The company was so small at the time that the summer intern party was at Bill Gates’ house. I planned to go to college at the end of the summer, but they offered me a full-time job. I took it, and the whole trajectory of my life changed. I was an almost-twenty-year-old who was offered an apartment and car until I got established. I had a salary and stock options while most people my age were in college. It was an amazing place to work and grow up. My whole business career, work ethic, and how I approach each day were formulated during my time working at Microsoft.
How did you transition from the video game industry to investing?
Despite never earning my undergraduate degree, I was lucky enough to take some time off and work on my MBA. I was doing some postgraduate work, which involved a lot of international travel — specifically in Asia. While there, I saw the rise in mobile technology in Hong Kong, China, and Japan. Their interest was ahead of the curve compared to the United States and other parts of the world. I researched and discovered that all the venture capitalists (VC) interested in mobile technologies at the time were based out of Europe, so I contacted them and pitched myself. Instead of ending up on the VC side, I was offered the opportunity to be the CEO of a mobile technology company that ended up focusing on gaming. I was in that role for a long time, and I learned the ins and outs of being the CEO of a venture-backed company.
After working at another venture-backed video game company in China, I discovered what I didn’t like about being in the investing business and what it means to be a good investor. I then put together my own fund, which differed from the others.
In 2019, Sperry competed in the Atacama Crossing Race in Chile.
Your work must keep you very busy. What do you do to recharge?
I run ultramarathons. Initially, I ran marathons, but while working in Jerusalem, a colleague challenged me to run across the desert in Namibia. I did it and have since completed races all over the world. Preparing for these events requires a lot of training and is really strenuous. Still, I enjoy being in extreme environments for days at a time — completely disconnected from the business world. My next race will take me to Greece, where I’ll once again push my limits and find the clarity and renewal that these experiences bring. After completing a race, I always feel recharged and refreshed.
What sets your fund apart from others?
Rogue Venture Partners is focused on investing in disruptive entrepreneurs in undercapitalized regions across the United States. Fifteen years ago, Seattle, Austin, Providence, Nashville, and Portland, Oregon were still up-and-coming regions in the entrepreneurial and investor space. I was lucky to have the financial backing to invest in those areas.
What qualities do you seek in the people or companies you work with?
I seek to work with humble yet visionary people who prioritize integrity and are committed to solving meaningful problems. Success isn’t just about making money — it’s about making a difference. In this day and age, business and society have moved away from that belief. It has become much more zero-sum, and the idea is that if it's not good for me, it's not good for you. We need to redefine success. Success doesn't mean I just made a billion dollars, but I screwed over a lot of people in the process. That is of zero interest to me.
You have also invested in international start-ups. Tell us about that.
I have worked with the World Bank to develop an entrepreneur and investor ecosystem in Palestine. I have also worked with the global humanitarian aid NGO Mercy Corps to build the first start-up accelerator in the Gaza Strip. I just launched a fund for North Africa to help transition and digitalize traditional business in Africa. Our company is headquartered in Morocco and focused on North Africa, Francophone Africa, Egypt, Nigeria, and Kenya.
Sperry and members of the Women Fund team at an event in Newport.
What led to the establishment of the Rogue Women’s Fund?
I was invited to an event for female founders and CEOs. I was the only male among the hundred people who were there to invest. This eye-opening experience taught me that for every $100 invested, less than a dollar will go to a marginalized community.
How do you define success?
While defining success, you also have to consider how to define failure. When working with female CEOs who raised three million dollars of capital, but didn’t meet their goal of raising five or ten million dollars, they feel like they failed. But statistically, the chances of raising that amount of money are marginally and extremely low. A three-million-dollar achievement shouldn’t be seen as a failure.
You’ve helped so many people grow. How do you help yourself grow?
I have enrolled in Harvard’s Divinity School program to help redefine success and rethink how morals and ethics apply to the world of business and making a profit. I get to create my own program, take any classes I want, and spend time with thoughtful people who are not in the business world. The experience has helped me be more thoughtful about investing in people and companies. I have learned to become a better contributor to society.
Are there any lessons you learned while at Pomfret that still apply to your life today?
While at Pomfret, I pushed many boundaries and made many mistakes. I figured out who I wanted to be and who I didn’t want to be. While learning these lessons, I had a great advisor and mentor, Ian Tourney, who never gave up on me. Mr. Tourney’s mentorship and those of my mentors from my time at Microsoft inspire me to be a great mentor today.
What else inspires you?
I am inspired by the idea that "to whom much is given, much is expected." I’m grateful for the opportunities I’ve had and feel a strong responsibility to give back. My two daughters also inspire me daily, motivating me to reshape the business world so they can thrive in a more equitable environment.