Woodstock competition offers $30,000 prize for best business idea

Cliff Johnson, left, and Larry Niles, two of Startup Woodstock’s organizers, hope to spur new business. Photo by Ethan Weinstein/VTDigger

WOODSTOCK – Let the best deal win.

With $30,000 in seed money, three Woodstock business leaders helped create Startup Woodstock, a pitch competition that will help launch a new business.

“The idea is that the closer the company is to solving some critical need in the community, this is a big plus,” said Cliff Johnson, one of Startup Woodstock’s organizers and judges.

Johnson moved with his family from Atlanta to Woodstock during the pandemic. More than a decade ago, while working in Portland, Oregon, he founded Vacasa, an international vacation rental management company, which he left in 2018.

Johnson is organizing the Woodstock competition with Jon Spector and Larry Niles, both members of the city’s Economic Development Commission, which focuses on issues such as housing, child care and downtown revitalization. The commission provided $10,000 for the competition, and the additional $20,000 came from private donors.

“We really want people to come here,” Nils said. “We will do everything we can to solve some of the very obvious problems, or barriers, to opening a business.”

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High rents downtown contribute to those barriers, Niles said, along with the perception that Woodstock has a difficult-to-navigate bureaucracy for prospective business owners. Although the former may be true, he refutes the latter, saying that almost all the business owners surveyed by the commission reported that they had positive experiences with local government.

Niles also rejects the idea that Woodstock is only a certain clientele.

“I always struggle with the idea that we’re just a rich city,” he said, “because we’re made up of a lot of merchants and a lot of people who have lived here all their lives.”

With that in mind, Nils and Johnson said startup Woodstock hopes to cast a wide net in recruiting potential applicants for the prize money. People whose ideas may only be in their infancy are invited to apply. So are service-based businesses such as electric, landscaping and child care companies.

“A $30,000 grant can help someone launch a new child care business,” Johnson said.

The competition’s criteria require the business to fill an unmet gap in the community and, hopefully, create living wage jobs or a sustainable owner-operated business.

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If successful, Johnson said he hopes the competition will create “a culture of entrepreneurship and (allow) people to create their own future.”

Johnson imagines that kind of culture could grow in Woodstock. He moved to Vermont to raise his family, relishing Woodstock’s school system, tight-knit community and access to the outdoors. He works remotely, and sees the Windsor County vacation destination as a draw for more remote workers than him.

For a town of only about 3,000 people, Woodstock devotes considerable resources to economic development. Since 2016, the city’s Economic Development Commission has awarded over $1 million in grants that support events, physical infrastructure, marketing and other initiatives.

This year, the city government created a program to pay landowners to convert short-term rent into long-term rent. The program aims to reduce the city’s housing shortage, made more acute because of the village’s attraction to tourists. Property owners received $3,000 if they agreed to a one-year lease with a tenant, and $7,000 for a two-year lease.

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Johnson acknowledged “concerns that come when a community brings in more vacation rentals,” including through Vacasa, adding that short-term rentals can be a “minor contributing factor to housing affordability.”

Still, he believes vacation rentals can be a “positive part of most communities” when they are licensed, taxed and follow local regulations.

Although it’s a new idea, Startup Woodstock could grow if it proves successful, according to organizers. Applicants can apply until December 1, at which point a to-be-announced panel of judges will narrow the field to a group of finalists by December 15. The finalists will present their ideas in February, and a winner will be chosen shortly thereafter.

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