Innovator Stories
Through a varied career, Cairn Cross has always let his interests lead the way.
“I want to create things, but I’m not your normal ‘creator’ type,” he said. “Over time, I realized what I enjoy most are these oddball, special projects that allow me the latitude to create and learn.”
Cross is probably best known as the co-founder of FreshTracks Capital, based in Shelburne, Vt., which has catalyzed more than $500 million in investments to high-growth Vermont companies since it was founded in 2000. He and co-founder Charlie Kireker have helped foster an investment ecosystem in Vermont and Northern New England that has continued to grow, inspiring other firms, investors, and entrepreneurs in the process.
Innovator Stories
Meet Cairn Cross
Through a varied career, Cairn Cross has always let his interests lead the way.
“I want to create things, but I’m not your normal ‘creator’ type,” he said. “Over time, I realized what I enjoy most are these oddball, special projects that allow me the latitude to create and learn.”
Cross is probably best known as the co-founder of FreshTracks Capital, based in Shelburne, Vt., which has catalyzed more than $500 million in investments to high-growth Vermont companies since it was founded in 2000. He and co-founder Charlie Kireker have helped foster an investment ecosystem in Vermont and Northern New England that has continued to grow, inspiring other firms, investors, and entrepreneurs in the process.
“We worked hard to help foster a climate of entrepreneurship in the state,” Cross said. “We were the place to go for early stage capital investment for a long time, and now there are other investors, which means the whole ecosystem has grown.”
Cross grew up in North Adams, Mass., and now lives in northern Vermont. He followed his love of skiing to Montana State University-Bozeman, where he competed on the college team, then spent a few years working in the ski business after college. He ended up enjoying the business side of skiing, too, and earned an MBA in finance from Southern New Hampshire University, leading him home to a role as a commercial lender at Vermont National Bank.
In banking, Cross became known for his ability to manage challenging, unconventional projects. “I had a lot of fun with that,” he said. “I became the person who would take on assignments the other reasonable bankers I worked with didn’t want to take on.”
“He’s that unusual guy who loved to do the screwball deals,” Kireker said. “He loved the deals other bankers thought were too messy—too many quirks, too risky. They intrigued Cairn, and he wanted to see if there was some nugget there.”
One of those assignments was managing the accounts of a limited partnership the bank entered with Green Mountain Capital, in which the bank had made an investment. Cross was unfamiliar with venture capital but took on the challenge. Not long after he delved in, “It felt like, ‘oh, this is really what I should be doing,’” he said. Eventually, he left banking and became an assistant manager at Green Mountain Capital.
GMC was founded during the Howard Dean administration as a Vermont Small Business Investment Company, and provided $13 million in financing for around 30 businesses in Vermont and New England. Cross loved the creative problem-solving aspect but wanted to do the work on a larger scale, creating an investment fund that could help early-stage companies with high growth potential find the capital they needed. “The lightbulb went on,” he said.
Cross and Kireker, who had helped found GMC, created FreshTracks with a new approach, aiming their expertise at different types of companies than GMC was working with. With complementary experience and professional networks, “We were a good match,” Cross said.
They ended up raising $11 million for the first FreshTracks fund. When it was founded in 2000, it was the largest VC fund that had ever been created in Vermont.
“He was always the best partner,” Kireker said of Cross. “He’s unassuming. He doesn’t act like he’s a big deal. He’s a classic, middle-class, rural American guy with ambitions, but without any pedigree or resources behind him to do what he has accomplished.”
In those early days, it was common to see just one or two companies in Vermont getting VC funding in a given year. In 2021, there were 38 VC transactions statewide, with 34 companies receiving funds. Venture capital has enabled new Vermont entrepreneurs to scale their companies and helped diversify a local economy traditionally tied to family-owned enterprises with capital to invest in new projects.
FreshTracks has invested in a remarkably diverse mix of companies. Those include the EatingWell Media Group, still based in Vermont and now a leading national source of diet and wellness information. Freshtracks’ early investments in SunCommon led it to help 8,000 homeowners go solar and expand to serve customers in New York’s Hudson Valley; it’s now a subsidiary of the publicly traded iSun, another solar company that employs Vermonters while working on sustainable energy solutions.
To Cross and his partners, this kind of growth proves that strong companies—and strong networks—can thrive in rural areas. “Places with intellectual capital, young people, and good ideas can create flourishing businesses,” said Kireker.
“Now, there’s a culture of startup companies in Vermont,” Cross said.
That culture has spurred other funds, new investors, new partnerships, and new entrepreneurs with new ideas. “There’s so much more going on here than outsiders think,” said Sam Roach-Gerber, vice president of VCET, which has offered mentorship and capital to early-stage businesses since 2005. “People like Cairn have seen it and believed it and made it happen for so many years. We have thriving cybersecurity and biotech and aerospace…we’re finally getting a spotlight.”
Growing a culture means making space for others, and Cross has a reputation for being honest, inclusive, and earnest. “He’s good at collaborating with lots of people in lots of different backgrounds,” said Kireker. “He’s the type of personality with no rough edges.”
Cairn is also known for helping others contribute to the Vermont economy. “Part of the reason Cairn means so much to me is he’s always been one of the people that advocates for me and makes me feel like I belong in the room,” said Roach-Gerber. “As a young woman in VC, that’s really important, and really affirming. He creates space for folks like myself. I had no experience when I started and didn’t know anyone in Vermont.”
Cross has also offered his insight across borders. As a Lever board member, he’s been able to see a similar approach work in his old hometown. “What Lever has done right as it’s expanded is said, ‘what is the actual economic ecosystem of where we live?’ It stretches over the Pioneer Valley, the Capital Region, in Southern Vermont, or broader. That makes Lever’s work flexible and powerful,” he said.
“What I liked right away about what Lever was doing was it reminded me of why we started FreshTracks,” he said. “Economic geography doesn’t end at state borders. The close proximity to Vermont, New York, and Massachusetts allows an economic development organization to have the best of both worlds. You want to cooperate with everybody. You want to bring people together and convene people. That’s the way we thought about FreshTracks. And now, Lever is in a place where it’s got a bit of a flywheel. It’s been able to pivot into a number of different areas.”
“We worked hard to help foster a climate of entrepreneurship in the state,” Cross said. “We were the place to go for early stage capital investment for a long time, and now there are other investors, which means the whole ecosystem has grown.”
Cross grew up in North Adams, Mass., and now lives in northern Vermont. He followed his love of skiing to Montana State University-Bozeman, where he competed on the college team, then spent a few years working in the ski business after college. He ended up enjoying the business side of skiing, too, and earned an MBA in finance from Southern New Hampshire University, leading him home to a role as a commercial lender at Vermont National Bank.
In banking, Cross became known for his ability to manage challenging, unconventional projects. “I had a lot of fun with that,” he said. “I became the person who would take on assignments the other reasonable bankers I worked with didn’t want to take on.”
“He’s that unusual guy who loved to do the screwball deals,” Kireker said. “He loved the deals other bankers thought were too messy—too many quirks, too risky. They intrigued Cairn, and he wanted to see if there was some nugget there.”
One of those assignments was managing the accounts of a limited partnership the bank entered with Green Mountain Capital, in which the bank had made an investment. Cross was unfamiliar with venture capital but took on the challenge. Not long after he delved in, “It felt like, ‘oh, this is really what I should be doing,’” he said. Eventually, he left banking and became an assistant manager at Green Mountain Capital.
GMC was founded during the Howard Dean administration as a Vermont Small Business Investment Company, and provided $13 million in financing for around 30 businesses in Vermont and New England. Cross loved the creative problem-solving aspect but wanted to do the work on a larger scale, creating an investment fund that could help early-stage companies with high growth potential find the capital they needed. “The lightbulb went on,” he said.
Cross and Kireker, who had helped found GMC, created FreshTracks with a new approach, aiming their expertise at different types of companies that GMC was working with. With complementary experience and professional networks, “We were a good match,” Cross said.
They ended up raising $11 million for the first FreshTracks fund. When it was founded in 2000, it was the largest VC fund that had ever been created in Vermont.
“He was always the best partner,” Kireker said of Cross. “He’s unassuming. He doesn’t act like he’s a big deal. He’s a classic, middle-class, rural American guy with ambitions, but without any pedigree or resources behind him to do what he has accomplished.”
In those early days, it was common to see just one or two companies in Vermont getting VC funding in a given year. In 2021, there were 38 VC transactions statewide, with 34 companies receiving funds. Venture capital has enabled new Vermont entrepreneurs to scale their companies and helped diversify a local economy traditionally tied to family-owned enterprises with capital to invest in new projects.
FreshTracks has invested in a remarkably diverse mix of companies. Those include the EatingWell Media Group, still based in Vermont and now a leading national source of diet and wellness information. Freshtracks’ early investments in SunCommon led it to help 8,000 homeowners go solar and expand to serve customers in New York’s Hudson Valley; it’s now a subsidiary of the publicly traded iSun, another solar company that employs Vermonters while working on sustainable energy solutions.
To Cross and his partners, this kind of growth proves that strong companies—and strong networks—can thrive in rural areas. “Places with intellectual capital, young people, and good ideas can create flourishing businesses,” said Kireker.
“Now, there’s a culture of startup companies in Vermont,” Cross said.
That culture has spurred other funds, new investors, new partnerships, and new entrepreneurs with new ideas. “There’s so much more going on here than outsiders think,” said Sam Roach-Gerber, vice president of VCET, which has offered mentorship and capital to early-stage businesses since 2005. “People like Cairn have seen it and believed it and made it happen for so many years. We have thriving cybersecurity and biotech and aerospace…we’re finally getting a spotlight.”
Growing a culture means making space for others, and Cross has a reputation for being honest, inclusive, and earnest. “He’s good at collaborating with lots of people in lots of different backgrounds,” said Kireker. “He’s the type of personality with no rough edges.”
Cairn is also known for helping others contribute to the Vermont economy. “Part of the reason Cairn means so much to me is he’s always been one of the people that advocates for me and makes me feel like I belong in the room,” said Roach-Gerber. “As a young woman in VC, that’s really important, and really affirming. He creates space for folks like myself. I had no experience when I started and didn’t know anyone in Vermont.”
Cross has also offered his insight across borders. As a Lever board member, he’s been able to see a similar approach work in his old hometown. “What Lever has done right as it’s expanded is said, ‘what is the actual economic ecosystem of where we live?’ It stretches over the Pioneer Valley, the Capital Region, in Southern Vermont, or broader. That makes Lever’s work flexible and powerful,” he said.
“What I liked right away about what Lever was doing was it reminded me of why we started FreshTracks,” he said. “Economic geography doesn’t end at state borders. The close proximity to Vermont, New York, and Massachusetts allows an economic development organization to have the best of both worlds. You want to cooperate with everybody. You want to bring people together and convene people. That’s the way we thought about FreshTracks. And now, Lever is in a place where it’s got a bit of a flywheel. It’s been able to pivot into a number of different areas.”