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

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

WOODSTOCK — Let the best company win.

With $30,000 in seed capital, three Woodstock CEOs helped create Startup Woodstock, a pitch competition that will help launch a new company.

“The idea is that the closer the company is to solving a critical need within the community, the more that’s a huge plus,” said Cliff Johnson, one of the organizers and judges at Startup Woodstock.

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

Johnson organizes 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,” Niles said. “We’re going to do whatever we can to resolve some of these very obvious issues or barriers to opening a business.”

High downtown rents are contributing 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 refuted the latter, saying almost all business owners interviewed by the commission had positive experiences with local government.

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

“I always cringe when I think that we’re just a rich city,” he said, “because we’re made up of a lot of artisans 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 in recruiting potential applicants for the prize money. Individuals whose ideas may be in their infancy are invited to apply. This also applies to service companies such as electrical, landscaping and childcare companies.

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

The criteria of the competition requires the company to fill a gap in the community and hopefully create jobs with living wages or a sustainable owner-managed business.

Johnson said he hopes the competition, if successful, will “create a culture of entrepreneurship and allow people to create their own destiny.”

Johnson envisions this type of culture growing in Woodstock. He moved to Vermont to raise his family and enjoyed Woodstock’s school system, close community, and access to the great outdoors. He works remotely and sees the Windsor County vacation destination as a magnet for more remote workers like him.

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

This year, the city government launched a program that pays landlords to convert short-term rentals into long-term rentals. The program aims to alleviate the city’s housing shortage, which has been exacerbated by the village’s tourist attraction. Homeowners received $3,000 when they agreed a one-year lease with a tenant and $7,000 for a two-year lease.

Johnson acknowledged that “concerns arise when a community gets more vacation rentals,” including about Vacasa, adding that short-term rents may be a “minor factor in housing affordability.”

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

Although it’s a new idea, startup Woodstock could grow if it proves successful, according to organizers. Applicants have until December 1st to apply, after which a jury to be announced will narrow down the field to a group of finalists by December 15th. These finalists will present their ideas in February and a winner will be selected soon thereafter.

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