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

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

WOODSTOCK — May the best deal win.

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

“The idea is that the closer a company is to solving some critical need within the community, that’s a big plus,” 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 ten years ago, while working in Portland, Oregon, he founded Vacasa, an international vacation rental 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 secured $10,000 for the competition, and an additional $20,000 came from private donors.

“We really want people to come here,” Niles said. “We’re going to do everything we can to address some of these very obvious problems or barriers to starting a business.”

High rents downtown add to the barriers, Niles said, along with the perception that Woodstock has a red tape that makes it difficult for would-be business owners to navigate. While the former may be true, he refuted the latter, saying that nearly all business owners surveyed by the commission said they had positive experiences with local government.

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

“I always shudder to think that we’re just a rich town,” 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, Niles and Johnson said Startup Woodstock hopes to cast a wide net in recruiting potential candidates for the prize money. People whose ideas may be in their infancy are invited. As well as service-based businesses such as electricity, landscaping and childcare companies.

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

The competition criteria require the business to fill an unmet void in the community and hopefully create viable businesses or a sustainable owner-managed 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 such a culture could grow at Woodstock. He moved to Vermont to raise his family, enjoying Woodstock’s school system, close-knit community and access to nature. He works remotely and sees the Windsor County vacation destination as an attractive place for more remote workers like himself.

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 more than $1 million in grants to support events, physical infrastructure, marketing and other initiatives.

This year, the city administration created a program that pays landlords to convert short-term rentals into long-term rentals. The program aims to alleviate the shortage of housing in the city, which has become more acute due to the attractiveness of the countryside 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.

Johnson acknowledged that “the concern comes when the community gets more rental housing,” including through Vacasa, adding that short-term rentals may be “a minor contributing factor to housing affordability.”

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

Although it is a new idea, Startup Woodstock could grow if it proves successful, according to the organizers. Candidates can apply until December 1st, and then the yet-to-be-announced jury will narrow the field to a group of finalists by December 15th. Those finalists will present their ideas in February, and the winner will be chosen soon after.

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