On episode thirty-nine of Mindful Warrior Radio, I host Aleca Hughes McPherson, Head of Portfolio and Platform at Highland. Aleca brings deep experience in strategy, operations, and leadership—supporting founders and scaling early-stage companies. She began her career at Catalant Technologies, rising from sales to a key role in strategic operations. A former captain of Yale’s Women’s Ice Hockey team, Aleca also founded the Mandy Schwartz Foundation, honoring her late teammate, and serves on the board of the Hockey Humanitarian Award—an honor she once received. In this episode, we dive into how Aleca helps build strong leaders, winning teams, and healthy, high-growth companies.

In our interview, Aleca shares the impact of sport on her career today. “Through sport, my parents taught us so many foundational life lessons. It’s such a big part of who I am—and who my brothers are. I imagine it’s the same for you with water polo. Within 10 seconds of being on the field, the ice, or in the pool, you know who someone is. Do they pass the puck? Do they backcheck? Are they excited when their teammate scores? I learned those lessons playing pickup hockey with my brothers, often with a bit of a chip on my shoulder—no one passed me the puck, so I had to go get it and make a name for myself. That mindset really propelled me forward.”

Aleca explains what Highland looks for in a founder. “At Highland, when we’re evaluating a founder, I think about how I show up to those conversations and what we’re really looking for. One of the key things we look for is strong founder–market fit. You often hear about product–market fit, which is of course important. But for us, founder–market fit is equally critical. Who is this individual? Why are they pursuing this particular problem or opportunity? What makes them so deeply passionate about it that they’re willing to go all in?”

Aleca shares one of Highland’s most frequently asked questions when evaluating a founder. “One of the first questions we ask ourselves when evaluating an opportunity is: Is this a founder I would work for? It’s really a question of ‘work with’ or ‘work for.’ Like—would you leave your current role to go work for this founder? I ask myself that, and so do our general partners, some of whom have been in the business for 25 or 30 years. We have a concentrated portfolio and make a very limited number of investments per fund, so this isn’t just a throwaway question—we take it very seriously.”

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