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

Cliff Johnson, left, and Larry Niles, two of the organizers of Startup Woodstock, hope to encourage new businesses. Photo by Ethan Weinstein/VTDigger

Woodstock – May the best business win.

With $30,000, three Woodstock business leaders helped create Startup Woodstock, a pitch competition that helps start new businesses.

“The idea is that the company is closer to solving some critical need within the community, which is a huge advantage,” said Cliff Johnson, one of the organizers and judges of Startup Woodstock.

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 co-organizing the Woodstock contest 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 allocated $10,000 for the contest, and an additional $20,000 came from private donors.

“We really want people to come here,” Niles said. “We’re doing everything we can to address some of these challenges or barriers to opening a business.”

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Niles said high rents downtown contribute to barriers, along with the perception that Woodstock has a difficult bureaucracy to navigate for prospective business owners. While the first statement is true, he dismissed the latter, saying that almost all of the entrepreneurs interviewed by the commission reported positive experiences with local government.

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

“I always think 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 in attracting potential applicants for the prize money. People whose ideas are still in their infancy are invited. There are also service businesses such as electric companies, landscaping and babysitting.

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

The competition criteria requires the business to fill an unmet void in the community and hopefully create living income 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 destiny.

Johnson imagines that kind of culture could grow in Woodstock. He moved to Vermont to raise his family, enjoying the Woodstock school system, close-knit community and access to the outdoors. He works remotely and sees the resort of Windsor as a draw for remote workers like him.

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

This year, the city government created a program that pays landlords to convert short-term rentals to long-term rentals. The aim of the program is to reduce the housing shortage in the city, which is exacerbated by the tourist attraction in the countryside. Property owners received $3,000 for a one-year lease and $7,000 for a two-year lease.

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

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

Although it’s a new idea, according to organizers, Startup Woodstock could grow if it succeeds. Applicants can apply until December 1st, at which time a panel of judges will narrow the field to a group of finalists by December 15th. then.

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