December 30, 2013
Bridge Boys - From Cambridge Little League Champs to One of the Most Unique Seed Funds in Boston

Here's a story for you.

Two "Big Dreamers" meet as kids in Cambridge. They grow up together. Each achieves his own success within the same industry, but they constantly fall back on one another for career advice and support. They realize that they could create something really special together, they join forces, and they make an impact in ways they could never have imagined while running from the blackcourts to the playing fields of "The 'Bridge".

You're probably thinking, that's the story of Ben Affleck, Matt Damon, and Good Will Hunting, of course.


It's the tale that is currently unfolding in the Boston tech community with Jordan Fliegel and Jeremy Levine, the "Bridge Boys", and the Seed Stage investment fund that they have been running since 2012, but are announcing today.

Jordan Fliegel and Jeremy Levine have known each other for a long time. As far as they can recall, they met playing for (they were adamant that they were correctly titled and still seemed very proud of being) "The 1995 Cambridge City Little League Champions". (Levine says they met on the bench; Fliegel, vouching for Levine's baseball skills, said he doesn't remember Levine ever 'being on the bench'.) Since then, they have been best friends. Both went off to their various college adventures; Levine to Syracuse to learn entrepreneurship, Fliegel to Bowdoin to continue his successful basketball career.

Levine came back to Cambridge to found StarStreet in 2009, the real money fantasy games site and Techstars company that has raised $2.1M. Fliegel, played pro hoops in Israel, got his MBA, and then started CoachUp, another Techstars company that connects coaches to young athletes and has raised $9.4M since last fall.

All the while, the two have remained tight and have helped each other with the other's own endeavor.

As Levine explained the story behind Bridge Boys, last summer they were hanging out and doing some work when Jordan popped up from his computer and said, "Hey, I think we could raise some money and start angel investing. Should we do it?"

Levine's response, "Uhh, YES!"

The first difficult decision they had to make was what to call the fund, but very quickly decided on Bridge Boys, what they had called themselves while playing sports in Cambridge growing up.

About a week later, they had the fund and started writing checks.

So what are the investment principles behind the Bridge Boys?

They invest small amounts of money, between $10-25K, in early stage startups. Their belief is that it is vital for many young companies to have some funds to help with the various expenses that arise early on for startups. Fliegel and Levine are especially proud of the fact that they were the first check for seven of the companies in their portfolio.

More than providing money, Levine and Fliegel believe that Bridge Boys brings a little something more to the table for the companies they are backing. They are young (both are 27) and are still smack in the middle of scaling their companies. In that regard, they can bring their experiences, that they are both living through, to the table when they advise some of the companies they have backed.

The reasoning behind this component of Bridge Boys has a lot to do with how Fliegel and Levine have complemented each other with their own projects. They have worked together and advised each other with CoachUp and StarStreet, sometimes even sharing talent. The growth of their relationship as their friendship has carried over to the startup world is something that they have found a ton of value in and want to replicate for others.

"If we could do this fund with small investments, deliberately keeping investments small, and really focus on helping peer founders," Fliegel said, "we could extend the special relationship that we have had-how helpful, supportive, and more enjoyable it is to have that support-to a wider community."

Levine added, "I found, that really some of the most helpful people for me were founders who were at the same stage or a little bit ahead." He mentioned Matt Lauzon and Jason Jacobs, among others, as key mentors/advisors when he was starting StarStreet.

Thus far, the Bridge Boys have funded (mostly the Seed Rounds) for StarStreet, CoachUp, Fashion Project, Freight Farms, Wymsee, Dashbell, Crowdly, ZappRx, Blank Label, Wefunder, Pistol Lake, Narvii, CommandIQ TripReactor, Crave Labs, Tracksmith, Revv, Mobee, and Ovuline. (They had confirmed a twentieth portfolio company, which they aren't ready to talk publicly about yet, a few minutes before we spoke.)

The Bridge Boys track record so far is pretty impressive. The companies in their portfolio are some of the most buzzed about and up-and-coming startups from Boston and as well as the West Coast. Recently, the BBJ came out with its list of the thirteen key Seed deals of the year, and Bridge Boys' portfolio companies made up five of the companies picked for the list.

What do the Bridge Boys look for in possible investments?

As Fliegel said, "One, we are looking for founders who are passionate about what they are doing; they are passionate about changing the world in some way. Two, that they are doing things that are cool, interesting, that will add value; that they have a real product that is simple to understand. And three, founders who we want to build long-term relationships with."

The last quality that Fliegel spoke about gave some insight into the depth and breadth of the Bridge Boys own long-term plans. "We're going to be doing companies together for a long time, and we want to build relationships with young founders for many years to come," he said.

The vision is being transferred to the portfolio companies as was obvious in talking to Crowdly's Dan Sullivan, who was backed early on by the Bridge Boys and shares space with Fliegel's CoachUp.

Sullivan said, "There are a lot of good investors [who were once founders] who have had their exits and are out of the trenches who have good advice on exit strategy and all the rest of it. But when I've got questions like what are you guys doing around how to structure bonuses, or HR policy, or time off, or what are you finding that really works around solidifying things from a company culture perspective, the type of stuff that should come from a more respected peer relationship, I can turn to [Jordan and Jeremy]."

The Bridge Boys are quiet unique, and, as things seem to be trending upward with a lot of their portfolio companies, they could also be quite successful. They certainly have a huge vision.

"There are very few examples of founder-led organizations supporting each other in a real meaningful way that has an impact," Fliegel said, "Not just grabbing drinks, but adding real value." "We hope to start a conversation about how early stage founders can be helpful and supportive of each other in a real way," he added.

"I'm not sure of any other young founders, who haven't had a liquidity event, who are leading a fund to invest small checks in other founders. I think what we are doing is pretty original and pretty unique and we'd love to see more of it in one way or another."

Dennis Keohane is the Senior Writer for VentureFizz. You can follow Dennis on Twitter (@DBKeohane) by clicking here.