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

WOODSTOCK – Let the best deal win.

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

“The idea is, 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 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 company, which he left in 2018.

Johnson co-hosts 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 urban 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 doing everything we can to solve some of these very obvious problems or barriers to opening a business.”

High rents in the city contribute to the barriers, Niles said, along with the perception that Woodstock has a difficult-to-navigate bureaucracy for potential business owners. While the former may be true, he refuted the latter, saying that almost all of the business owners surveyed by the commission reported positive experiences with local government.

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

“I always cringe at the thought 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 their whole lives.”

With that in mind, Niles and Johnson said the startup Woodstock 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 help someone start a new childcare business pretty easily,” Johnson said.

The competition’s criteria require that the business fill an unmet gap in the community and, hopefully, create living wage jobs or a sustainable owner-operated business.

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 Woodstock’s school system, close-knit community and access to the outdoors. He works remotely, and sees the Windsor County vacation destination as a draw for more remote workers like him.

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

This year, the city government created a program to pay landlords to convert short-term rentals to long-term rentals. The program aims to relieve the city’s housing shortage, which is made more acute due to the village’s attraction to tourists. Property owners received $3,000 if they agreed to one year’s rent with a tenant, and $7,000 for two years’ rent.

Johnson acknowledged that “concerns that come when a community gets more vacation rentals,” including through Vacasa, adding that short-term rentals can be a “smaller contributing factor to housing affordability.”

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

Although it’s a new idea, Startup Woodstock could grow if it proves successful, according to 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. These finalists will present their ideas in February, and a winner will be chosen soon. after that.

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