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

WOODSTOCK — Let the best business win.

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

“The idea is, the closer the company is to solving some critical need within the community, that’s a big plus,” said Cliff Johnson, one of the founders 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 organized the Woodstock contest with Jon Spector and Larry Niles, both members of the city’s Economic Development Commission, focusing on issues such as housing, child care and downtown revitalization. The commission provided $10,000 for the competition, and an additional $20,000 from private donors.

“We really want people to come here,” Niles said. “We will do everything to solve some of these very obvious problems, or obstacles, to opening a business.”

High rents downtown contribute to the barriers, Niles said, along with the perception that Woodstock has a difficult-to-navigate bureaucracy for prospective business owners. While the former may be true, he dismissed the latter, saying that nearly all business owners surveyed by the commission reported having positive experiences with local government.

Niles also dismissed the idea that Woodstock caters to just one clientele.

“I always get nervous thinking that we’re just a rich town,” he said, “because we’re made up of a lot of business people and a lot of people who have lived here their whole lives.”

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

“A $30,000 grant can help someone launch a new child care business very quickly,” Johnson said.

Competitive standards require business to fill an unmet need in the community and, hopefully, create gainful employment 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 thought that kind of culture could grow at Woodstock. He moved to Vermont to raise his family, enjoying Woodstock’s school system, tight-knit community and access to the outdoors. He works remotely, and sees the vacation destination of Windsor County as a draw for many 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 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 into long-term rentals. The program aims to alleviate the town’s housing shortage, which has been exacerbated by the village’s attraction to tourists. Property owners receive $3,000 if they agree to a one-year lease with a tenant, and $7,000 for a two-year lease.

Johnson acknowledged the “concerns that come up when a community gets a lot of vacation rentals coming in,” including through Vacasa, adding that short-term rentals can be a ” little factor in housing affordability.”

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

Although it is a new idea, Startup Woodstock can grow if it proves successful, according to the organizers. Applicants can apply until December 1, at which point a panel of judges will be notified to narrow the field to a group of finalists on December 15. Those finalists will present their ideas in February, and a winner will be chosen shortly thereafter.

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