Matthew McCooe and the 200-mile investment thesis

A venture capitalist’s calendar usually measures distance in flights. Matthew McCooe’s had room for a bicycle. In September 2025, Connecticut Innovations took its third Tour de Connecticut from Stamford to Mystic: four days, about 200 miles, and a succession of stops where the people receiving investment could meet the people making it. There were founders, guest riders, company visits and meals. The itinerary even made room for a board meeting. Apparently, governance can survive a change of shoes.

McCooe, CI’s chief executive since 2015, had named the ride’s inspiration: Senator Chris Murphy’s walk across Connecticut. He wanted people to appreciate the state and the people working in it. A trip through back roads offered a way to see the place whose future his organization was financing. The destinations were close enough to connect by bike, yet varied enough to resist any tidy description of a startup scene.

For McCooe, the tour fits a larger preoccupation. An investor can make money from a company located almost anywhere. His employer has a particular address on its ambitions. Connecticut Innovations is the state’s venture capital arm, and the work carries two obligations: earn returns and help businesses take root in Connecticut. A profitable exit is welcome. What remains nearby matters, too.

The salesman before the investor

Before McCooe judged other people’s business plans, he had businesses to help build. After Boston College, he worked with the Jesuit Volunteer Corps and then co-founded a beverage startup. A later interview revisited the experience of selling Brazilian soft drinks. That is a useful detail in a career now described through funds and acquisitions: once, the product being sold was something a customer could drink.

The career moved through sales, marketing and product launches. In 1996, he became marketing manager for MCI’s startup joint venture in Mexico. His responsibilities included designing, positioning, branding and launching its business products. Those products generated more than $35 million in first-year revenue. These were commercial responsibilities with an immediate test: would customers buy?

He earned his Columbia MBA in 1998–1999. At Eureka Networks, which he co-founded, he became vice president of sales and marketing and general manager of the New York office. His remit included relationships with real estate partners, staff management and the deployment of networks inside buildings. The glamorous phrase would be telecommunications entrepreneurship. The actual job also involved making sure the network worked inside someone else’s property.

Eureka eventually sold for $110 million. Later, at Chart Venture Partners, McCooe’s investing included a return to operating work. He stepped in as CEO, and subsequently as sales and marketing vice president, during a turnaround at IntegriCo Composites. The progression makes his interest in the practical life of a company easier to understand. He had occupied the chair on the other side of the investment discussion.

A university idea needs a customer

Between Eureka and Chart came Columbia University’s Science and Technology Ventures. McCooe helped launch spinout businesses and deploy a seed fund. During his tenure, 11 companies went public or were bought by publicly traded companies. Research was the starting material. Building a company required another set of decisions.

The subject stayed with him. In 2004, he contributed a chapter called Achieving Proof of Concept to a book about building and investing in university spinouts. Even the chapter title is revealing. Proof of concept sits at the awkward junction between a promising idea and something another person can evaluate. It asks an inventor to make the promise visible.

By April 2022, he was discussing venture capital and Connecticut entrepreneurship with students at Yale’s Tsai CITY, alongside Josh Geballe. In 2024, at a discussion accompanying UConn’s innovation documentary, he emphasized the state’s knowledge workers and the role of universities and schools. He described his work as “trying to identify the next great entrepreneur.” The search could begin in a classroom long before it reached an investment committee.

“You gotta be bold.”

Matthew McCooe, on the advice he gives

Boldness, in this setting, has a practical companion: access. In 2016, Connecticut Innovations joined UConn and the federal Economic Development Administration in contributing $500,000 apiece to the Quiet Corner Innovation Cluster. The collaboration aimed to help smaller businesses in eastern Connecticut draw on university research and development resources. McCooe supported giving employers that assistance early. An established manufacturer could need a connection to research just as a new founder could need a first investor.

Two columns on the scorecard

McCooe took over CI in July 2015 after working as a managing partner and fund manager at Chart. The assignment drew on both halves of his background: venture investing and technology commercialization. It also added the obligations of a state-sponsored organization. Connecticut’s legislature had created CI in 1989 to encourage enterprise and job creation. Its decisions would be judged by more than the arithmetic familiar to a private fund.

Seven years into his tenure, that tension became the subject of a Yale School of Management case study. McCooe and his team had been working to bring private venture fund practices into an organization operating within state government. The case framed their position as a recurring management problem: when does a difference between a private investor and a public institution become an opportunity, and when does it become a hazard?

CoolIT Systems offers a concrete version of that problem. McCooe had backed the Canadian liquid-cooling company and described it as one of his career’s strong financial outcomes. Yet he also pointed out the limited number of Connecticut jobs it created. In his own account, the return left part of the assignment unfinished. That is an unusually demanding way to look at a successful investment: the cheque can clear while another column remains unsatisfactory.

The two-column approach also explains why CI might look overseas. Its 2019 VentureClash event in Tel Aviv offered Israeli startups a chance at investment and introduced them to Connecticut’s investors and business resources. The geography of the search could be international; the intended destination for a growing business remained specific. McCooe was selling a place to build, drawing on the experience of someone who had previously sold products.

The work between the cheques

There is a quieter measure of his approach in CI’s fiscal 2025 activity. Alongside investment, the organization supported 127 direct hires in its portfolio and introduced its first Talent Fair. Three hundred young professionals had an opportunity to meet Connecticut startups. A founder can have a promising product and money in the bank, then discover that the next constraint is finding the person who can do the work.

The bike tour made those relationships visible. In 2024, the team visited more than a dozen portfolio companies and connected with over 250 participants. McCooe rode with board chair Michael Cantor, chief marketing officer Lauren Carmody and colleagues. The names matter because this was a collective undertaking. A venture portfolio consists of separate companies, but a useful introduction can pass between them.

The following year’s route joined Stamford, New Haven, Hartford, Storrs and Mystic. Its schedule paired company visits with local stops: Athletic Brewing in Milford, P2 Science in Naugatuck, the Hartford Yard Goats’ ballpark and UConn. Those juxtapositions are part of the appeal. A state economy contains laboratories, factories, sports grounds and lunch counters. Seeing them in one trip makes an abstract investment mandate rather easier to picture.

A ten-word rule, and room to play

McCooe’s thoughts about management also come from home. Writing about what his children had taught him, he described a bargain: he would keep a message to ten words or fewer if they gave him their attention. He suggested carrying that economy into office announcements and meetings. Anyone who has sat through a meeting that outlived its purpose can appreciate the attraction.

Other lessons included listening before responding, asking experts for help, speaking directly and allowing disagreements to end. He described turning kitchen clean-up with his children into a shared activity with music, singing and dancing. Work, in that account, benefits from people enjoying each other’s company. The household example is modest, and more revealing than a polished leadership slogan.

His personal preferences have a similar lack of ceremony. He names Tod’s Point as a favourite place, likes reading a good book and declares an enthusiasm for games involving a round ball. These are recognizable pleasures for someone based in Old Greenwich. They give the investor a life beyond the investment vocabulary, without requiring a grand theory about how every hobby improves a portfolio.

What the next investment leaves behind

The financial scale has grown. For the fiscal year ending June 30, 2026, CI reported $59.3 million invested across 75 early-stage companies and venture funds. Those deals attracted another $1.2 billion in outside capital. Cash proceeds from portfolio exits reached $66.5 million; total proceeds across investment activities were $76.1 million. Those figures describe CI’s collective activity, rather than a personal tally for its chief executive.

Alongside that activity, CI has a dedicated AI/Q Fund, with Gwen Cheni directing its investment work in artificial intelligence and quantum technology. Giving a specialist responsibility for a field is a sensible extension of McCooe’s operating experience: an organization needs people who understand the work well enough to make decisions about it. Hiring and investment are closely connected here.

The harder question persists after any annual results announcement. Will a company keep building? Will the next employee find a reason to come to Connecticut? Will knowledge travel from a university into a business and then into another generation of founders? These are slower questions than a transaction headline allows. McCooe’s career has repeatedly taken him into the space where the answers have to be made practical.

A bicycle happens to be a good vehicle for that space. It makes distance tangible and company visits literal. The tour put investors on the roads between the places they were discussing, with time for conversation at the stops. For a chief executive whose assignment includes what stays behind, going out to meet people is a fairly direct place to start.