Head of School Henry Smyth commenced the 43rd annual H.K. Cotton Memorial Lecture on Wednesday, March 12, 2025, by introducing its speakers — two forward-thinking businessmen who share their affinity for Gilman, innovation, and making the world a better place.

The lecture is a tradition established by the late Henry K. Douglas Cotton, a prominent businessman in Baltimore, with several grandsons, and later great-grandsons, who attended Gilman. Through the named lecture, Mr. Cotton wanted “to instill in our students a better understanding of the world of business and economics.”

John Avirett ’01 is a partner and member of the private equity team at StepStone, focusing on venture capital and growth equity investments. He also serves on the Board of Trustees at Gilman, among other organizations. His previous company, Greenspring Associates, was purchased by StepStone in 2021. He has helped lead investments for companies like SpaceX, Roblox, and Chewy.

As he shared his professional journey, the audience learned that Avirett’s entrepreneurial spirit began during his time at Gilman, when he and his classmate started a summer business, J&J Light Hauling. Through guerilla marketing — putting up signs at Eddie’s and other local shops — they earned enough money taking other people’s junk to the dump in their pickup truck to fund their summer’s surf trips. “We didn’t think that this was actually a real business,” he said. Their perceived expectation at the time was that they should go to good colleges and get serious jobs in finance or engineering. So the pair took “boring internships” at established companies.

In college, Avirett shared the hauling-junk-as-a-business idea with a friend while studying abroad; this friend would go on to found Junk Luggers, which now has 150 franchises and was acquired by a private equity firm in 2022.

Avirett emphasized four reflections from his career:

1. If you have a great idea, go build a company.
2. “Utilize the Gilman network; it's incredibly powerful.” (Avirett mentioned how he did this several times over the course of his career.)
3. “Venture capital is one of the keys to fueling the innovation economy.”
4. Venture capitalists take major risks and often suffer losses. On the flip side, they get to change the world.

“It’s been an incredibly rewarding career for me,” he said.

Dr. Rushika Fernandopulle ’85 was the recipient of the William A. Fisher Medallion when he graduated from Gilman. He was also voted by his peers as “most likely to succeed” and “most in with the faculty” in the 1985 yearbook.

During his talk, he spoke highly of his Gilman education, noting that he appreciates it more and more as time goes by. “I learned how to write … and learned how to think … I got a taste of starting things … I warmed the bench in varsity soccer where I learned how to win and how to lose,” he said. “Most importantly, I learned how I can help change the world.”

As a third-year medical student, Fernandopulle realized that despite good intentions, the system of healthcare we had “was really awful” related to outcomes, patient experience, physician experience, and costs. “What we simply needed to do is start over,” he said.

In 2011, he co-founded Iora Health, a primary care company that did not follow the typical fee-for-service model but instead relied on a flat patient fee of $40 per month (more or less, depending on ability to pay) for care. Later, Iora secured contracts with organizations such as Dartmouth College and Zappos, which covered the monthly fee for their employees. 

Fernandopulle stayed on as Chief Innovation Officer when Iora Health was acquired by One Medical for $2.1 billion in 2021. When the company was sold to Amazon in 2023 for $3.9 billion, he decided it was time to move on. He shared that just two weeks ago, he launched another company, Liza, which works to help existing practices change models of care.

His parting advice for the Upper School students at the assembly:

1. “Don’t let other people put you in a box.” Someone else won’t create a job that’s perfect for you so create it yourself.
2. “Much of the value created in the world is created in the in-betweens.” Translation: Don’t be limited by labels or categories. You can be a scientist but also a businessman; you can work in policy but also technology.
3. “Figure out what upsets you about the world. If you focus on your purpose, the money will come.”
4. “Be willing to take risks.”
5. Borrowing from advice from his own Gilman advisor Edward Thompson from 40 years ago, “Don’t let people tell you what you can’t do.” That is only about what they can’t do.
6. Talking about the rise of AI, he said, “Focus on the human aspect. … In the past, jobs were about muscle. Today, they are about brains. In the future, they will be about heart.”

He concluded his talk with, “Enjoy the rest of your time at Gilman. I can’t wait to see how you all are going to change the world.”

Following the lecture, more than 25 students gathered in the Gilman Room to join the featured speakers for a question-and-answer session. Topics included finding purpose and opportunity, dealing with failure, adjusting the decision-making process for risk, the skills required for success in venture capital, and how AI will impact the future of entrepreneurship.

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John Avirett '01

Dr. Rushika Fernandopulle '85