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Get Advice, Then Ask For Money: Motorcycling Business Leaders Advise Entrepreneurs At 'Road Pitch'

Outside a barn in Lowell are a bunch of motorcycles as part of Road Pitch.
Hilary Niles
Niles Media
Local organizers host each "Road Pitch" session in a unique venue. In Lowell, Steve Mason and Trish Sears make use of their farmhouse's barn.

"There’s not enough funding in Vermont to help businesses get off the ground and grow" is a common refrain among startup and expanding businesses seeking investment capital to fuel their growth. But one unique Vermont event aims to teach entrepreneurs that, before they ask for money, they may want to first ask for advice.

On a Monday morning, the Green Mountain Harley-Davidson dealership in Essex Junction is closed, but the parking lot is crammed with motorcycles of every make. Inside, about four dozen investors, entrepreneurs and business leaders have come to get “pitched” by local entrepreneurs looking for money and advice.

Among today's pitchers, there’s Dick Vaughn, owner of Perky Planet; Jamie Northrup and Eric Smith, co-founders of PairedIQ; Chelsea Camarata, who founded Kayden Apparel; and Kerri Tracy, founder of Cubby Spaces.

This is the first of eight pitch sessions to be held across Vermont this week as part of a four-day event called “Road Pitch,” so-named because all the business experts on this trip also happen to be motorcycle riders. The entourage travels between venues on two wheels.

Motorcyle riders as part of Road Pitch drive on a Vermont road.
Credit Hilary Niles / Niles Media
Niles Media
About four dozen riders attend Road Pitch each day, but usually split off into smaller groups to ride from one venue to the next.

Now in its fifth year, most of the riders are regulars who've returned year after year. Some of the pitchers, too, come back for an encore — like Lex Osler. He co-founded QOR360 with his father, a company that makes and sells a new style of ergonomic chair.

“Last year I came to you with an idea, and this year I come to you with a business,” Osler opened in his presentation. “Our mission is to change the way the world sits, and I’m here to ask for $1 million to help us do that.”

Road Pitch founder Cairn Cross said businesses are encouraged to hone their pitches and try again the following year.

“One mistake that entrepreneurs make is thinking that they know everything,” Cross said. “And making a whole bunch of mistakes that if they had solicited some advice, they would have been steered away from that.”

Lex Osler stands next to Cairn Cross at a Road Pitch event.
Credit Road Pitch, courtesy
Lex Osler, left, who's pitch for QOR360 won the pitch contest in Essex Junction on Monday, stands with Road Pitch founder Cairn Cross, right. The prize is $500, a Vermont Teddy Bear dressed up like a biker, and the chance to compete for $5,000 against other local winners in October.

Cross, who also co-founded FreshTracks Capital, a Vermont-focused venture capital firm, conceived of Road Pitch to help put fledgling entrepreneurs in touch with successful ones.

Unlike the reality-TV show Shark Tank, the vast majority of people pitching at Road Pitch don’t walk away with any financial commitments from the riders. A lot of these businesses, the riders say, aren’t ready for funding.

For example last year, rider and business consultant Eric Egeland reached out to Dominic Spillane about his pitch for a business called Theater Engine. It’s an online platform designed to help community theaters promote their shows and connect with audiences.

Egeland recalled what Spillane originally asked for in his pitch: “I think they just said a million 'cause it’s a nice round number, if I remember correctly.”

But really, Egeland said, Spillane hadn’t actually known what he needed. He worked with Spillane as a client, helping to focus and tighten Theater Engine’s business plan and financial projections.

Jennifer Cohen makes her case for Calypso Consulting to riders convened at the The Mint makerspace in Rutland Wednesday morning.
Credit Hilary Niles / Niles Media
Niles Media
Jennifer Cohen makes her case for Calypso Consulting to riders convened at the The Mint makerspace in Rutland Wednesday morning. Calypso offers steel drum workshops for team building and to corporate clients and at retirement communities.

“They can’t be like, ‘I don’t know that yet, I’ll figure that out.’ No, you need to nail your market. You need to nail it all down. It’s a painful, horrifying process for most entrepreneurs because they just want to — they just wanna do a Theater Engine!” Egeland laughed.

“They want to have fun," he added. "And so we come in and go, ‘Nope! Gotta nail all this down.’”

Freshly armed with answers to questions Spillane hadn’t known to ask, he soon realized: He doesn’t even need capital investment in order to grow. He can “bootstrap it” without selling equity in his creation, Egeland said.

This is one example of why Cross, the Road Pitch organizer, believes it’s crucial for entrepreneurs to solicit a variety of opinions as they hone their business ideas. But this can be challenging in a rural state like Vermont, he said, where so few people have experience with companies that have scaled up.

One such rarity is Alan Newman, who founded Magic Hat Brewing Company and the cleaning products producer Seventh Generation. Last winter, Newman raised $600,000 in private equity funding to help a husband-and-wife team grow their business after they presented at Road Pitch two years before.

Gov. Phil Scott on a 1998 Harley-Davidson Fatboy bike in Hyde Park, Vt.
Credit Hilary Niles / Niles Media
Niles Media
Gov. Phil Scott joined Road Pitch for presentations in Hyde Park on Monday. He rode away on his "trusty" 1998 Harley-Davidson Fatboy.

Cross pointed to that as Road Pitch’s most glowing achievement to date: “That is the story that really becomes why something like this can be successful.”

It’s hard-earned success, though. Cross’ own venture capital firm has yet to invest in any of the businesses that have presented in four years of his organizing Road Pitch on his firm’s behalf.

“Sooner or later, we have to fund a company in order to make it more palatable ... to our firm,” Cross said.

In the meantime, he feels good about the connections and learning Road Pitch is facilitating. And he and the other riders are having a lot of fun doing it.

Disclosure: VPR board member Charlie Kireker is a co-founder of FreshTracks Capital, and QOR360 is a VPR underwriter.

Hilary is an independent investigative reporter, data journalism consultant and researcher based in Montpelier. She specializes in telling stories of how public policy shapes people's daily lives.
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