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January 10, 2010

Where Have All The Good Mentors Gone (from Boston)?


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 mainly 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.

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Nice post Jeff. I was at an event for women entrepreneurs hosted by TCN recently where this issue was brought up. In addition to the reasons you mentioned, we also talked about the need for role models who had built successful companies while achieving work-life balance and raising families. The good news is there is a group of women executives and CEOs who get together regularly to discuss these issues and support each other, and there was talk of escalating this to include aspiring entrepreneurs so they can be mentored effectively by those who have been there and done that. That was very encouraging to hear, and I am looking forward to finding out more when they are ready.

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Thanks for the comment, Shuba.  I think it
is indeed improving.


There are plenty of mentors available in Boston entrepreneurial scene. Angels are there too (they are just a lot more low-key, compared to the show-off style of CA folks).
Maybe young entrepreneurs need to focus a bit less on those with lofty pedigrees and seek out mentors who can get them to the next step (and that next step 99.99% of the time will not be $1B capitalization). Boston is full of experienced executives, professionals, and entrepreneurs willing to help the next generation. The new "crop" just needs to stop looking to connect with the black swans (those who got lucky to be at the right place and the right time) and rather look for someone who has done something they want to do before over and over again.
Heavy "scar-tissue" coupled with lasting power is what one should look for in a mentor.

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Thanks, Apollo. There are some who say
that being quiet and low-key is to the Boston
community’s detriment. Perhaps the old Puritan culture still remains?  Anyway,
I take your point and thanks for the feedback.


Hi Jeff,

I think there are plenty of examples of some other great folks from exactly the same companies that you've mention. While not the CEO - I'm sure that you'll agree that Shabbir, Andy Payne, Reggie Sommers, Joe Paratore all went on to build new companies, contribute and mentor future startups. Just to name a few, but there are many others from many other successful Boston startups.

Maybe the real point is that experienced, successful mentors are truely one of the rarest and most valuable assests in a startup; You can never have enough and it is super important to included them in the future. We also need mentors to be visible, external leaders.

Well said, Chip. There's no substitute to help accelerate a start-up than to have great people, particularly experienced mentors. There are many great ones in Boston, but we could use more, particularly those that are willing to invest real dollars and time.

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Personally, I look to SCORE for guidance, and I've been able to find some great online input from seasoned mentors -- but the best ones have actually be in the Boston area.

The CA scene makes me a bit leery, because it seems like everyone is so over-the-top enthusiastic and 1000% convinced that *we can make it work!* no matter what. But I also got burned pretty badly in CA high tech back in the early 90s before everyone else got dot-bombed, thanks to an overly optimistic (read, unrealistic) "can-do" attitude. I learned my lessons early, and I haven't forgotten.

Fortunately, I have never had a problem finding adequate mentoring in the Boston area. When you're clear on what you want to do and you ask around, people somehow appear who can help you. They don't have to be formal, official "mentors" in order to contribute valuable insights. Also, I tend to focus on results and people who not only did Big Things, but also aren't moving at a million miles an hour. Being able to stop and carefully consider options and choices is paramount to me. Go-go-go only gets you so far.

This slow-and-steady approach has paid off. I've been part of a very small team that's built a nationally syndicated public radio show from scratch, over the past 14 years. We're still going strong, bringing excellent independent music to over 100 markets nationwide (and internationally) each week. We don't have a huge budget and a huge staff, and our website is in desperate need of an overhaul, but we've got a loyal following, and every week of every year, we bring new music to people who might never otherwise get to hear it. Content really is king... or queen, if you will ;)

Along the way, we've gotten help from all over the place -- much of it from peers. Mentoring comes in all shapes and sizes -- and in some cases, the true value of it depends on the person seeking the guidance and advice.

What about Shikhar? Not only does he continue to be active with startups but he teaches future founders every day at HBS.

Yes - Shikhar has been an awesome mentor, angel investor and now professor. We need many more like him.


Just take a wander down to Waltham and the Clean Energy Fusion Center, where a bunch of CEO's and entrepreneurs who went thru the NE Clean Energy Fellowship are providing mentoring and guidance to this space.

There are a number of use out there trying to move the ball forward.


Its a double edge sword though. It seems everytime a "law" is passede we loose more of our rights!
Tracy K.

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