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

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

Woodstock – Let the best business win.

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

“The idea is that the closer a company is to solving some critical need within the community, the bigger the advantage,” 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 that he left in 2018.

Johnson is organizing the Woodstock competition with John 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 contest, and an additional $20,000 came from private donors.

“We really want people to come here,” Nils said. “We will do our best to resolve these very obvious problems, or barriers, to business opening.”

High rents downtown contribute to the barriers, Niles said, along with the perception that Woodstock has a difficult bureaucracy for potential business owners to navigate. While the former may be true, he refutes the latter, noting that nearly all business owners surveyed by the commission said they had a positive experience with local government.

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Niles rejects the idea that Woodstock only caters to a certain clientele.

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

With that in mind, Niles and Johnson said Startup Woodstock hopes to cast a wide net to recruit potential applicants for the prize money. People whose ideas can only be in their childhood are invited to apply. So are service-based businesses such as electric, landscaping and childcare companies.

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

Competition standards require businesses to fill an unmet need in the community and, hopefully, create livelihood employment 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 destiny.”

Johnson envisions that kind of culture growing at Woodstock. He moved to Vermont to raise his family, savoring Woodstock’s school system, tight-knit community and access to the outdoors. He works remotely, and sees the Windsor County vacation destination as an attraction for many remote workers like him.

For a town with a population of about 3,000, Woodstock devotes considerable resources to economic development. Since 2016, the city’s Economic Development Commission has awarded more than $1 million in grants to support programs, physical infrastructure, marketing and other initiatives.

This year, the city government created a program to pay landlords to convert short-term rentals into long-term rentals. The program aims to alleviate the city’s housing shortage, which is exacerbated by the village’s attraction to tourists. Property owners received $3,000 if the tenant agreed to a one-year lease and $7,000 for a two-year lease.

Johnson acknowledged that “communities have concerns about more vacation rentals,” including that through Vacasa, short-term rentals can be a “small contributing factor to housing affordability.”

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

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

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