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 inspire 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 the Woodstock startup, a pitch competition to help launch a new business.

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

Johnson moved 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 management company, which he left in 2018.

Johnson is organizing the Woodstock contest with Jon Spector and Larry Niles, both members of the town’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 want people to come here,” Niles said. “We will do everything we can to solve some of these very obvious problems or barriers to opening a business.”

High rents downtown add to the barriers, Niles said, as does the perception that Woodstock is a difficult bureaucracy to navigate for prospective business owners. While the former may be true, he dismissed the latter, saying that nearly every business owner surveyed by the commission reported having a positive experience with local government.

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

“I always claim that we are just a rich town,” he said, “because we have a lot of craftsmen and a lot of people who have lived here all their lives.”

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

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

The competition criteria requires 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 destiny.”

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

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

This year, the town government created a program that pays landlords to convert short-term rentals to long-term rentals. The program aims to alleviate the town’s housing shortage, which is exacerbated by the village’s appeal 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 “concerns come when a community gets more vacation rentals coming in,” including through Vacasa, adding that short-term rentals could be a “minor factor contributing to housing affordability.”

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

Although it is a new idea, the Woodstock Startup could grow if it is successful, according to the organizers. Applicants can apply until December 1st, at which point a panel of judges to be announced will narrow the field to a group of finalists by December 15th. Those contestants will present their ideas in February, and a winner will be chosen shortly. After that.

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