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Head out on the highway, looking for investments

Published in The Boston Globe

By Hilary A. Niles

Don’t think “Shark Tank.” Compared to that venture capital reality TV show, Road Pitch is more like a “dolphin tank,” says Debby Pearson, co-owner of Green Mountain Harley Davidson in Essex Junction, Vt. Road Pitch is friendly and takes its time.


Liz Holtz, of Liz Lovely gluten-free cookies, pitches riders at the Vermont Granite Museum in Barre on Aug. 3. Holtz won for delivering this venue’s best pitch. She will go on to compete at a pitch-off in October for $4,000 in prize money and a year’s worth of mentorship from the Road Pitch Riders. (Photo by Hilary Niles.)

Pearson is one of about 45 entrepreneurs and investors who, for five days this August, are touring the state on motorcycles to get pitched by about 50 local startups. Now in its third year, Road Pitch is the brain child of Cairn Cross, cofounder and managing partner of Vermont-based venture capital firm Fresh Tracks Capital.

While financial investment is the ultimate goal of the trip for his business, Cross says it’s only one way Road Pitch fosters Vermont’s “entrepreneurial ecosystem.” Another is through feedback. Even if that means gently directing business owners back to the drawing board.

Rider and engineer Jeff Finkelstein says his peers on the trip try to be helpful, not aggressive. “You don’t want to dissuade someone from their passion. But on the other hand, you hate to have someone venture down a path that you think may be fruitless,” Finkelstein said.

The riders are brewers, solar innovators, educators, financial planners, software developers. Their collective net worth likely exceeds total wages in many of the cities and towns where they’ll stop: $112 million (Randolph), $27 million (Hyde Park), $2 million (Lowell). Some are looking to invest. Most offer suggestions. All come along to enjoy a good ride. One day, one of them may cut a check or join a company’s team of advisers.

Most Road Pitch events are followed by casual downtime, where pitchers and riders can mingle and network. (Photo by Hilary Niles)

Most Road Pitch events are followed by casual downtime, where pitchers and riders can mingle and network. Here, college students Max Robbins and Peter Silverman chat with a rider after their pitch at the Grand Isle County Courthouse. (Photo by Hilary Niles)

In the meantime, incremental progress and ripple effects signal to Cross that Road Pitch is working.

In Bennington, local organizer Brian McKenna said just the event of Road Pitch rolling into town has given his community something to prepare for, and that in itself creates meaningful traction.

McKenna and other volunteers helped aspiring entrepreneurs from the Bennington area hone their ideas, then chose five teams to pitch the riders Tuesday morning. He said one of the biggest success stories from the day was a company named Pool Shark H20, which developed a digital log book for companies to track pool maintenance. McKenna said owner Scott Trafton, like a lot of locals with potentially scalable businesses, came in knowing a lot about their respective fields, but not much about the business of business.

“Business models, pricing, client acquisition — these are things that a regular Joe who’s just trying to start a business doesn’t anticipate having to answer from a potential investor,” McKenna said. Using the same same feedback form riders would use during the pitch sessions, McKenna gave them a road map. And drawing on each other’s experiences (because some locals are seasoned) the group grew together. McKenna said in the course of one month, Trafton’s pitch underwent the kind of transformation Bennington needs more of.

That’s exactly the evolution Cross hopes to catalyze. After all, the more business acumen permeates the state, the more investment opportunities Road Pitch eventually will surface.