Where Have All The Good Mentors Gone?

I confess to being a Shrek fan. My kids made me (well, sort of) buy the music CD to Shrek 2 and my favorite song on that CD is the Jennifer Saunders song – Holding Out For A Hero. When they were little we would play it over and over again in the car.

I had that song ringing in my head as I joined a few other start-up mavens at a recent gathering last week organized by Scott Kirsner at the Microsoft NERD Center in Kendall Square. One of the topics we discussed was: where have all the good mentors and angels gone from Boston? Unlike in Silicon Valley, where successful entrepreneurs seem to jump back into the fray start-up after start-up, Boston’s successful entrepreneurs seem to fade off into the sunset.

Two of the more successful companies in Boston in the 1980s were Lotus and Powersoft. Their founders — Mitch Kapor and Mitch Kertzman, respectively — are brilliant guys with an incredible amount to offer. Unfortunately, both moved off to California and are active investors and mentors for young start-ups out there.

I served as an executive team member of two companies in Web 1.0 era who were very successful in their day – Open Market (IPO 1996, peak market capitalization of $2.5 billion) and Upromise (acquired by Sallie Mae in 2006 for 9 figures and today has $21 billion assets under management in 529 college savings accounts and 12 million members). My two bosses, Gary Eichhorn (Open Market CEO) and Michael Bronner (Upromise founding CEO), were incredible mentors to me, but both are now retired and focused on non-profit activities and family.

Unfortunately, for the next generation of young entrepreneurs in Boston, there simply aren’t that many former founders/CEOs who built large, successful companies hanging around. I can’t blame them, but in order for this community to build the next wave of billion dollar companies, we need more senior talent mentoring and investing in our youth.

There are some signs that things are changing. For example, Bill Warner (founder of Avid) has invested a ton of energy in helping get TechStars off the ground. And it was good to read in last week’s news that Don Maclagan, Nicholas Negroponte and James Pilotta have stepped up and invest in music-intelligence start-up Echo Nest. I would love to see more of this going forward. We need the old heroes to stick around and teach the next generation!

“Where’s the street-wise Hercules to fight the rising odds?” – Jennifer Saunders.

Jeff is a partner with Boston-based VC firm Flybridge Capital Partners. Read his past peHUB posts, or follow him on Twitter at www.twitter.com/bussgang.