Elm City Entrepreneurship with Collab’s Margaret Lee and Caroline Smith

Jacob Bendicksen
Apr 8, 2018 · 17 min read
Collab’s winter incubator cohort (photo courtesy Collab)

Collab is a community-focused startup incubator based in New Haven. Founded by Margaret Lee and Caroline Smith (both Yale ‘14), Collab has pioneered a uniquely founder-centric incubator model that aims to use entrepreneurship as an engine of local economic development. Along with Origami, Collab is a part of the Elm City Innovation Collaborative (ECIC) grant, and we’re thrilled to be able to work alongside them.

I had the chance to sit down with Margaret and Caroline to discuss what makes Collab special, the New Haven startup community, and how entrepreneurship and activism can combine with powerful results.

Interview lightly edited for clarity.

“Our core mission is to make sure that entrepreneurship is accessible in Connecticut.”

Jacob Bendicksen: Tell me the story of Collab — why did you start it, and what have you learned along the way?

Margaret Lee: I think we can go way back! We were both Yale 2014, but before that — it’s funny, we’re very similar. We’re both from Kentucky: I’m from Louisville, she’s from Lexington, I’m full Korean, she’s half Korean, and we both went to Yale in the same year. We didn’t really meet — we knew of each other — and after we graduated, we met and started talking about how to bring the Yale and New Haven ecosystems together and how to create community between the Yale entrepreneurial ecosystem and the New Haven tech scene, startup scene, and entrepreneurs.

I was working at the Yale Entrepreneurial Institute, which is now the Tsai Center for Innovative Thinking at Yale, and Caroline was a community organizer working at a tech company called SeeClickFix. We started brainstorming, and the first thing that we landed on was an event series. This was back in 2015, and we said ‘let’s create an event series that brings together Yale students and New Haven residents,’ everyone from a freshman to people who have lived here for their entire lives in the same room.

In front of that room, we recruited an organization to talk about their mission and three challenges that they were running into, and those three challenges served as the design challenges in a human-centered design exercise that we ran with the room. We didn’t call it human-centered design, but that’s what we were doing. We were really interested in the ideas that were coming out of these sessions that would help the organizations, and more importantly, we were interested in the relationships that were being formed: people working in small groups for two hours on a problem that they mutually bought into. Knowing each other’s names, looking each other in the eye, that was an important part of the work that we wanted to do.

When you think about City Hall and Yale’s administration, it gets a little intimidating, but we knew that there was a desire for connectivity at the bottom. We did that for about a year — tons of people came out, and we noticed two things: there are incredible ideas in New Haven that can stand on their own, not just for the organizations, but ideas and products and potential businesses and nonprofits and things like that; and there are incredible people coming back to these sessions, building capacity and confidence and asking for more.

We were faced with the question of how to support these ideas and these people, and based on both of our experiences (venture incubation on my end and community organizing on Caroline’s), we came up with an idea for an incubator that supports early-stage entrepreneurs in New Haven and in Connecticut.

Caroline Smith: We do two main things. One, we run a bunch of events highlighting the stories of New Haven and Connecticut entrepreneurs that are doing things that matter to them, things like women and mothers in entrepreneurship, faith in entrepreneurship, youth in entrepreneurship. We’re working on an event with Junta and the Fair Haven Library for immigrants in entrepreneurship.

Two, we have our incubator program, which is a six-week program for six to seven teams of early-stage entrepreneurs. They get a bit of funding, a mentor, coworking space, all the different things that an incubator typically provides. Additionally, we provide childcare and transportation and interpretation services so that a single mother can go through the program and be successful, even if she just came here a month ago, she can go through the program and be successful — our core mission is to make sure that entrepreneurship is accessible in Connecticut.

“We want to say that every person, from every single neighborhood, can be an entrepreneur.”

J: What do you see as Collab’s role in the bigger New Haven community, and how do you see that changing in the next five years?

C: I think we’re really interested in a few different kinds of culture shifts. One, who does entrepreneurship belong to? Right now, when you see different entrepreneurship spaces, those are often occupied by a certain kind of individual, and there isn’t often a collective vision across multiple neighborhoods of what economic development and entrepreneurship and innovation should look like in the city.

For us, through Collab, we want to say that every person, from every single neighborhood, can be an entrepreneur and can use entrepreneurship to contribute to their livelihood if they want to. We want that route to be accessible.

The second culture shift we’re interested in is how incubators and accelerators think about economic development and the role of the individual in economic development. Incubators and accelerators are often interested in the venture and the venture’s success, sometimes to the detriment of the actual individual’s livelihood, and for us, we’re very interested in starting with the individual. If we can empower the individual, if we can make them be heart-powered, strength-centered leaders themselves, that’s the best way to produce the best ventures and resilient individuals and therefore contribute to economic development that’s wider, broader, and truer as a result. This will contribute to a more resilient and stronger Connecticut and a more resilient and stronger New Haven.

M: The only thing I’d add to that is about the next five years. We just wrote a grant application talking about how we believe that Connecticut is going to go through a big transformation in the innovation economy in the next five to ten years. You look at stories like Silicon Valley, Austin, Boston, and all of these different cities that have gone through these transformations in the past twenty years, and you see these great cities that are often missing something — we hear that a lot, from a lot of different people, even people who live there, who love it. We’re really interested in being part of the conversation as Connecticut matures, and making sure that we create our own space, that we don’t become the next Austin, that we try to create economic development and entrepreneurship support systems that include everyone and lift up the people who have called this place their home for years and deserve to be a part of development.

We want to focus on that piece as well as the catchphrase of talent attraction and talent retention. We love that — let’s bring everyone here, let’s keep Yale students here — we’re totally down for that, and we’re also interested in what it means to lift up the people that live here. This is their home and has been for a long time, and we think that if we can do that, the transformation that Connecticut will be going through will be sustainable, and it will be a shining example for different parts of the country for how it can be done and how we can take everyone with us. That’s something that we’re interested in being a part of, being a small voice in pushing it in that direction.

“We’re interested in entrepreneurship as a way of scaling the stuff that’s already happening in New Haven.”

J: Does the focus on the founders and the people who are building these companies — do you think that’s something that New Haven is especially positioned to focus on? Is that a function of the city, timing with Connecticut’s becoming an innovation hub, is it something unique, or is it just something that should happen?

C: I think that New Haven is uniquely positioned to do that because it’s doing it in other sectors. Right now, there are programs like the Neighborhood Leadership Program out of the Community Foundation or the Community Leadership Program out of the Graustein Foundation that are taking a particular focus on these heart-powered, strength-centered leaders. There’s already investment in that, but that hasn’t, in the state of Connecticut, crossed over into the entrepreneur and innovation space, and for us, we’re very interested in that being a part of entrepreneurship resources and entrepreneurship support, because that’s a way that kind of leadership can scale.

If an individual founder is approaching their work in that way, it’s going to change the way they hire, the way they treat their cofounder, the way they treat their team, and the product they actually produce in the world. We’re interested in entrepreneurship as a way of scaling the stuff that’s already happening in New Haven.

M: The first thing that came to mind for me is that it’s already happening here, and there’s already a culture of that focus on individuals in New Haven. I think we — you kind of alluded to this — we think this should be everywhere, we don’t think it’s unique to New Haven. We think thinking about individual entrepreneurs, their passions and values and joy, is an important part of the venture incubation process. That’s our big hypothesis — we think it’s applicable everywhere, and we think Connecticut is a great place to test it out because it is an emerging economy and there’s already a culture. It’s a perfect storm of ‘let’s see if we can make it work here,’ but we think it should be everywhere.

“Genius and brilliance happen at intersections.”

J: What are you excited about right now in New Haven and more broadly?

C: Something that I think has been increasing but should happen more is the intersection and collision spaces of entrepreneurship and activism and different forms of public service. There’s more connective tissue and more collaborating happening with those kinds of organizations. I think that’s really interesting — genius and brilliance happen at intersections, and with the Yale-New Haven collisions, there’s brilliance there, neighborhoods working together. The particular one that I’m excited by is activism and entrepreneurship joining hands and using more common language to work towards similar goals. That’s one of the assets that New Haven has, an incredible activist culture, and if they can help support entrepreneurship culture and change it, that would be amazing.

M: There’s so much happening. Working with Matt, you’ve probably experienced a lot of this — Origami is one example, District’s coming up, newhaven.io is the local tech community and they’re doing events that are just exploding. There’s something happening right now, and it’s the rumblings of startups and innovation and entrepreneurship, and it’s not mature yet, but if you talk to anyone in the space, they’ll tell you the same thing.

We have a lot of challenges, but I think those challenges also present opportunities for us — I think what we talked to you about, how we can steer those in a direction that’s sustainable and good for all different kinds of people. I think that’s exciting because there’s so much happening, so much activity all over New Haven, and there’s so much opportunity to take that and create something different, a different story.

Connecticut’s story is something that we talk about a lot — we’re an underdog story right now, as you probably know, and there aren’t that many good stories coming out of Connecticut — or so it seems. We’re seeing more and more amazing stories on the ground, and we’re excited to see where that could go and how we can nudge or push it to be something that really feels good for us and the people that we love.

“There’s so much power in combining business models with activism-like goals, and we’ve seen that with some social ventures that have come through our program.”

J: To combine what both of you said, are there stories that you’re super excited about in entrepreneurship and activism right now that are worth mentioning?

C: The first thing off the top of my head is the work that we’ve been able to do — the best events that we’ve run have been deeply in partnership with others. It’s not that when we run an event on our own it’s sad, but there’s something that changes when you work with other groups. We’ve been able to partner with Dwight Hall and this group called The Table Underground on a food entrepreneurship meetup, there’s an event called Meeting of Soup where we’re partnering with the guy who runs Atticus and the Grove. I think those things are exciting, and that particular event — one of its goals is to activate storefronts in New Haven’s Ninth Square that are closed down, since there have been quite a few retail stores in the Ninth Square that have closed down. Things like that are very interesting to me, especially when they’re done well.

M: What comes to mind for me are social ventures. Social entrepreneurship is interesting to me and always has been — it’s what I was drawn to the most when I was working at Yale, and there’s so much power in combining business models with activism-like goals, and we’ve seen that with some social ventures that have come through our program. There are organizations trying to achieve some social good or some social goal using non-profit and increasingly for-profit models, so there’s some interesting overlap there between activism and entrepreneurship that I’ve always been intrigued by.

Based on New Haven’s culture of activism and community development, there’s a lot of good, fertile ground for that, so as we grow as an innovation economy, I can see that being a big part, because it’s something that a lot of people can relate to and do and feel compelled to do.

“What’s interesting about entrepreneurship is that it provides people a really unique opportunity to make an impact without necessarily having to go through the grass tops.”

J: Do you see entrepreneurs focusing mostly on community-based activism or more in government with alders or state representatives? Are people working top-down or bottom-up?

C: You’re asking whether entrepreneurs work more with the grass tops or the grass bottoms?

J: Yeah.

C: I’m thinking about our ventures, and there’s definitely some blending. Two of our founders, Ron Coleman and Dan Hicks, was trying to start something called New Haven Counts, which is basically a version of New Haven Reads, but for math, in order to improve the next generation of student mathematicians and entrepreneurs. I’m thinking about Ron — he’s the program director at New Haven’s Teach for America, and he knows tons and tons of kids. He goes to the Hillhouse basketball games to support them, and he also knows Jason Bartlett at the Youth Department at City Hall, and his mom is the woman at the schools who’s able to schedule how the schools are used over the summer. I’m thinking about him as a blend, as someone who’s able to talk to the grass tops and talk to the grass bottoms.

M: What’s interesting about entrepreneurship is that it provides people a really unique opportunity to make an impact without necessarily having to go through the grass tops. That’s the unique opportunity that gritty skills give you — the opportunity to impact a lot of people’s lives and create an organization with a business model or structure that helps sustain it without having to rely on the government. A lot of entrepreneurs like Ron rely on the government because they have to or they can, but what’s unique about what we’re seeing is that it’s not just grassroots activism, it’s grassroots something, organization-building and impact-having that isn’t reliant on the government. I think this is something personal to me — I love seeing this stuff, and I think I pick up on that a little bit when I think about entrepreneurship and the power of it.

C: I think that’s inherent in a for-profit, since they have to talk to grass tops in order to license a building, but at the end of the day who’s feeding them? It’s their consumers, their customers, the community. Tikkaway over there intentionally hired, out of forty people who applied, the seven people who walk to work, and that was a very intentional decision on their part, and a lot of people who go eat there see the employees walking around because they live there, and that matters. That’s who they’re held accountable to, the people eating there, not the grass tops. Inherent in a for-profit organization are the constituents that are purchasing their stuff.

M: Social ventures especially, because they’re trying to have a social effect very related to, but not always about that transaction. For that explosive social impact, they don’t need the government, and the government’s only adding to it and facilitating by creating the structure overall that allows these things to happen.

“I just wanted to be a part of it because it was exciting.”

J: Where did the idea for the Friday Fund come from, and what’s surprised you about who’s gotten funding?

C: Basically what happened was that I was on a run — I listen to a bunch of different podcasts, and follow a bunch of tech bros on Twitter, since they inspire me and give me a lot of energy. There’s this one guy, Ryan Hoover, from Product Hunt, who I think is so exciting — I just love all the content he puts out, and he started this thing called Weekend Fund that’s a VC, and the whole idea is that it’s for people who are building stuff on nights and weekends. I just loved the name, it just made me happy, I just wanted to be a part of it because it was exciting.

With a lot of the things that make me excited with Collab, I love the branding or how we message ourselves, and I was thinking about how Collab can incorporate names or language that we’ve always wanted to lose. When I was on the run, I got the name Friday Fund in my head, and it just stuck. For us, we support early-stage entrepreneurs, and Friday Fund has that two-pronged goal of being able to support early-stage entrepreneurship with a tiny bit of funding to be able to do a community event because we also love New Haven. We hang out in New Haven on Friday nights, getting ice cream and doing other stuff, and we thought that Friday nights could always use more events and activities, and we imagined an intersection there of entrepreneurs gaining information and meeting customers, and just contributing to an incredible Friday night in New Haven.

J: And it all started with the name?

C: It all started with the name — honestly, just Ryan Hoover. We’re currently working with this entrepreneur Ivy Low, who’s the first recipient of the Friday Fund. She’s really fascinating — her dream is to create a gift shop specifically for visitors from China or students who are from China so they can receive local goods, whether it’s chocolates or Yale or Connecticut or New Haven memorabilia to bring back to China, since she sees that as a huge potential need. She also creates these really delicious egg rolls. Another need that she sees is all of these individuals all over Connecticut that are creating local goods — she wants to be a central place for people to get local stuff. Right now, she’s going to do a tiny version of this at the next CitySeed farmers’ market, the next one that’s open when the summer hours start, and she’ll have a table with her stuff but also a couple of other local foods to sell to see if people are interested. Friday Fund, though — it all started with Ryan Hoover. Maybe that should’ve been our origin story for Collab: Ryan Hoover.

“She’s just a young artist who wants people to be proud of being here in Connecticut, and we’re really amped to be able to support her.”

J: I know you’ve mentioned various projects here and there, but are there any that we haven’t talked about that you’re psyched about right now?

M: Our ventures, I mean, we’re excited about all of them. A few that come to mind: Lotusleaf Therapeutics, she’s a prenatal masseuse who has talked with thousands of pregnant women who can’t sleep at night because they’re so uncomfortable, but as soon as they lie on her table, they’re like ‘oh, I wish I had this at home.’ She created a pillow that she wants to sell, and she’s sold 200 of them — she was a part of our program, and she has just incredible vision for what kind of company she wants to build and how she wants to serve pregnant women. We love the idea of women serving women and mothers serving mothers, and there’s something so inspiring about the depth of knowledge that she has about the pain, both personal and from her customers. We could literally go through all six — there’s a section on our website with all of our ventures, and you should look at that. We love all of them.

C: Another one that pops up that’s aligned to the theme of this conversation is Sheneta. She’s an entrepreneur out of Bridgeport who’s creating the My City Initiative. It’s basically a merchandising brand aimed at helping instill pride in Connecticut — she’s an artist, really young, and all of her friends who are also artists want to move to New York or Boston because that’s where they feel like they can be artists. She’s like ‘no, stay here, let’s build a culture in Connecticut,’ so she’s made these hats that have the MTA stop logo on them, like New Haven, Bridgeport, all the train stops, as well as sweatshirts. She’s sold a lot, 150 maybe, and they’re just cool. She’s really good at making stuff that makes you look really good and just really cool — it’s dad hats and big sweatshirts, she’s probably going to create a line of denim jackets with the little stickers. She’s just a young artist who wants people to be proud of being here in Connecticut, and we’re really amped to be able to support her.

M: Other community things like the Grove where we’re at — it’s been around for a long time and continues to be an anchor, the library is building Ives Squared, which is going to change entrepreneurship in New Haven, District I’m sure you’ve heard of — who knows what that place is going to look like, and we’re really excited to see what it can be for the community as well as for the startup community.

C: Tsai CITY at Yale has been increasingly prioritizing and focusing on Yale-New Haven connectivity in as many ways as they can — they’ve been one of our great partners, and I think it’s really cool to see a soon-to-be institution of Yale that has tons of financial backing making that a priority and making it so accessible and permeable. That’s awesome, and it’s just exciting to see, as the years progress, how that goes.

M: Urban Collective is a black-owned coworking space, and we love them. They have a really cute space right near where I live, so I love that place, love Randi.

C: ConnCAT is creating this thing called Conncorp, which is buying up properties along Dixwell Plaza to bring some energy and entrepreneurial life there. There’s tons of stuff that’s exciting, and overall, there’s a lot of connectivity among all the projects. That’s in part thanks to the support of the grant that we were part of, the ECIC (Elm City Innovation Collaborative) that you guys are a part of — it helps to create connective tissue, but a lot of us are just friends. We know about each other, we’re pipelines for each other, and that’s been cool to see.

“These are the people who are in the back, creating the structure for a lot of things to happen, and they deserve recognition, for sure.”

J: With all that’s happening, who are the unsung heroes of New Haven startups and activism who make it all happen?

M: There are so many! Every one of the individual entrepreneurs who have been here, who are continuing to be here, who are emerging here, they’re the lifeblood of all of this. We exist to support them, so they are quite literally the unsung heroes — everyone we meet with every single day for hours and hours.

Another thing, going back to the ECIC that’s managing this grant that’s coming from the state for New Haven. There are a few people who work on that grant, sort of backstage, that work really hard and maybe don’t get the recognition that the project gets. The Economic Development Corporation’s CEO, Ginny Kozlowski, put in tons of work to make it happen, Michael Harris at Mayor Harp’s office — he’s the special assistant to Mayor Harp and chair of the ECIC, he put in tons of work to make this grant happen and implement it right. Elinor Slomba is the supervisor for ECIC, she works really hard. Slate Ballard, who’s the owner of the Grove and helped put together the grant in the beginning, he really led the charge with getting all the projects and having everyone get the proposal and applications together, he put a lot into it. These are the people who are in the back, creating the structure for a lot of things to happen, and they deserve recognition, for sure.

Thanks to Margaret and Caroline for taking the time to chat! Don’t forget to check out the wonderful work that Collab does on their website, and feel free to reach out to us at Origami if you‘re interested in getting involved.