Scott Bailey / Board Member Spotlight

In this Q&A, Scott Bailey recounts his journey from Larchmont, New York, to finding a welcoming community at the University of Vermont (UVM). He discusses his role in starting UVM’s entrepreneurship program, his work with MassChallenge, and founding his company, Bequall. Scott also highlights the supportive nature of Vermont and his passion for building sustainable communities.

Blaise: Where did you grow up and what led you to choose UVM?

Scott: I grew up just outside of New York City, in the small town of Larchmont. I was looking at a lot of schools, but I fell in love with [UVM’s] campus. I thought everyone was nice and welcoming. I remember walking around, lost, and people just came up to me and offered help. I thought to myself, ‘This is different from New York.’ And then I was excited about the business school in particular –– I met some of the professors and thought it was an exciting place.

Blaise: How did you involve yourself at UVM?

Scott: When I went to pick an academic minor, there wasn’t an entrepreneurship program, so I ended up building one with [former Dean] Rocki-Lee Dewitt. They have formalized a lot more of this programming since I graduated. I co-founded the first business plan competition and entrepreneurship club at UVM. As well as the club basketball team.

Blaise: How did you get introduced to MassChallenge?

Scott: I was working at VCET when I had an idea for a statewide [entrepreneurship] competition in Vermont. But there wasn’t enough funding. It was 2009, I was young and naive, and I needed somewhere to really learn. At the time, MassChallenge had just started accepting applications, it was their first year. And Ty Danco, a mentor and entrepreneur around VCET, said, ‘Scott, you need to go check out these two guys from Bain and Company who started [MassChallenge] and just soak up as much as you can.’ And so I did – I dropped everything and ended up going to MassChallenge. I ended up working there for ten years, spending most of my time in fundraising, building programs, and public-private partnerships.

Blaise: Did you encounter any Vermont companies when you were working at MassChallenge? 

Scott: I was proactively pitching to Vermont companies! But at the time, it was a nascent vibe [in Vermont]. It’s not like it is now; there were a lot of [Vermont] companies, but they were smaller. We primarily sourced from schools: Harvard, MIT, Boston University, Boston College.

Blaise: Since leaving Vermont, you have created an Alumni Advisory at UVM and participated in LaunchVT. What’s been driving you to push entrepreneurship in the state?

Scott: I thought Vermont gave me a shot when no one else would. Vermont supports the underdogs and gives people an at-bat. It’s a highly collaborative place. People are building great businesses with strong missions and values. I also love it, it’s beautiful. I stayed there all my summers [at UVM], which I thought was the best time despite snowboarding too many days a year at Stowe. 

Blaise: Why did you found your company, Bequall?

Scott: It started with my own issue: housing in Boston. As I became the manager of the [MassChallenge] Boston program, housing seemed to be the number one thing that challenged everyone. So it was just front and center in my brain. I was also working to secure free office spaces for MassChallenge and I started to meet with these mixed-use developers that were building housing, commercial spaces, and retail. And I was really inspired by what building a community could look like and the space that people wanted to be in. My first vision was a startup village in the Boston Seaport and that basically started a six-year journey to where I am now. 

Blaise: Tell me more about your product. What does Bequall sell?

Scott: The thesis back then was small, efficient spaces should provide access and opportunity to those looking to live close to work and opportunity. Today, Bequall is a strategic partner for investors and developers focused on Accessory Dwelling Unit (ADU) and infill developments. Specializing in volumetric modular construction. We deliver purpose-built products that maximize home value while enhancing resident experience. We act as an Owner’s Representative, and streamlines the entire development process—optimizing zoning, embracing off-site manufacturing, and reducing time-to-market—ensuring projects meet both financial objectives and community goals.

Blaise: What are some lessons you’ve learned as a founder?

Scott: People want to say yes, you just have to make it easy for them to do so. So follow up: half the reason we raised money was from sending follow up emails. People ask, ‘How do you fundraise?’ I raised money for MassChallenge because I just kept following up. I circled people with people. I was incessant in that pursuit. And that’s what it really takes: You have to be really persistent. You can’t drop things, you have to follow through. Be shameless, but create value at the same time. You don’t know if you don’t ask.

Blaise: Why do you enjoy serving on VCET’s board?

Scott: The thing I find most rewarding is working with David and the team to hone opportunities and maximize the impact of the organization. I think the other board members are incredibly smart too. It’s a stacked crew and shows you that Vermont’s got a lot of firepower. And I think that’s a really good sign for entrepreneurs who are trying to start [in Vermont], but maybe have an impression that they need to be in Boston or the Bay Area or other markets. I think when you see an organization that has a lot of depth, access, and expertise, you say, ‘I could be here and still access a lot of resources and markets.’ 

Blaise: What’s an ideal Vermont day for you?

Scott: Going for a bike ride along the water, then heading to the Skinny Pancake for a crepe. Next, it’s out to Bolton potholes for a swim. Come back, and either hang out on the lake, or end the night somewhere on Church Street.

This interview has been edited for brevity and clarity. 
Find Scott on LinkedIn here. You can also learn more about his startup, Bequall, here.