The Outsiders

One of my favorite childhood books was SE Hinton's The Outsiders.  For whatever reason, I always related to this tough group of teenagers who felt like societal outcasts just because they were born on the wrong side of town.

I was reminded of the book the other day when attending the Unconference.  The Unconference is a Boston-based technology conference put on by the MassTLC that has no agenda.  Instead, the agenda is created dynamically the day of the conference by the attendees.  Sessions are created on the fly, led by whoever wants to lead a session.

At many conferences, there is a sense of "insiders" and "outsiders".  Insiders have attended the conference in past years, speak on panels, walk around with great confidence and poise because they "know everyone" and are sought after during the course of the conference.  They are the popular kids at the conference.  Outsiders come to the conference knowing no one else, are often lingering awkwardly on the periphery during networking time and struggle to gracefully secure air time with the very people they came to the conference to meet.

The Uncoference tries to break this paradigm with a more dynamic sesssion format alongside structured one on one sessions between well-known insiders with eager outsiders.  I try to sign up for these one on ones every year, which are essentially an extension of the offce hours concept that many VCs (including Flybridge) have been championing as a way to provide more accessibility and transparency between insiders and outsiders.  A few years ago, I was matched with a very tall, eager entrepreneur who shared with me his passion for private coaches for sports.  His name was Jordan Fliegel and, although his 6 foot 7 inches frame stood out amongst the crowd of nerds and middle aged investors, he was an anonymous outsider that day.

Since then, Jordan's company, CoachUp, has secured venture capital funding from a local big name firm (General Catalyst) and grown into a local success story.  In a few short years, Jordan has become the definition of an insider – he's now one of the best known figures at any conference and has even started an angel fund, Bridge Boys, with one of his childhood friends.

A few years ago, I met a student during office hours at HBS, who was embarking on a new company.  He was new to Boston, having grown up in Iowa, attended Brown and then worked in Chicago.  I was with him at a lunch at a conference and, sensing his discomfort as an outsider, started to introduce him around – endorsing him with the insiders around me, like reporter Scott Kirsner and serial entrepreneur Walt Doyle.  Before long, Brent Grinna (CEO/founder of EverTrue), blossomed into one of the local innovation community's strongest leaders and insiders, sought after as a mentor by others for his success with the company (backed by big time, insider firm Bain Capital) and within the community.  Brent reminded me of this story with this recent tweet.

Francis Ford Coppola turned SE Hinton's book into a move, released in 1983.  The movie starred a slew of young Hollywood outsiders – a remarkable number of whom became the ultimate Hollywood insiders, including Tom Cruise, Rob Lowe, Patrick Swayze, Emilio Estevez and Ralph Macchio.  That's the magic of a dyanmic, entrepreneurial environment – today's outsiders can become tomorrow's insiders.  That's why immigrants, students and other outsiders are such valuable members of the entrepreneurial ecosystem – and why we should be doing everything we can to encourage and support them.

5 thoughts on “The Outsiders

  1. Great post Jeff. We all need to be open. It is not a zero sum game – every talented individual that joins our ecosystem helps the whole community grow.


  2. @bussgang I remember leaving my Corp gig & being a Toronto Startup Community outsider. Events like #LeanCoffeeTO @StartupDrinksTO opened the door for me to come inside.


  3. @Brent – couldn’t have said it better. Jeff, you are a shining example of all that is right in the VC world. Your work to support students, young entrepreneurs, important causes and politicians who fight for them, and the Boston startup ecosystem is exactly what we need from top VCs in the community. And while “outsiders” may not see how that activity may directly impact the bottom line for your firm and LPs, as an “insider” I have no doubt that your efforts will come back to you many fold. You have well earned your great reputation. Keep it up!


  4. well said, jeff! it’s easy to forget the outsized impact “insiders” can have on “outsiders” like myself, especially in the earliest days of getting off the ground. what if you hadn’t introduced me to walt and scott? i think about that quite often. it was such a simple thing for you to do, but it would have been just as easy for you to *not* make those introductions. but as i mentioned in the podcast, those relationships have had profound ripple effects on our business. i can trace early customers (like walt’s high school, middlesex), early team members (we have many WHERE/PayPal alumni on our team) and early investors (TechStars and associated angels) back to your introduction.
    insiders should remember that the seemingly smallest introductions and connections go a long way. and investors like yourself happen to be some of the most well-connected people in the world. so even if the founders you meet aren’t always a fit for your financial capital, i’m hopeful more of your peers in the venture community will follow your lead in generously investing relationship capital. because the compound effects of that investment are more powerful than money. thanks for your continued support along the way. it looks like it’s time for me to watch “the outsiders”.


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