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The 11th Nantucket Conference: The Good, The Bad, and The Ugly

Friday May 7, 2010 by Desmond Pieri - Interim CEO

Frankly, my first Nantucket Conference was mostly good.  But the one ‘bad/ugly’ was a surprise, given what emerged as the central theme of the three days.

Though not on the agenda, the question consistently asked was, “How does Boston promote innovation and entrepreneurship in competition with Silicon Valley?”  And the consistent answer was, “By people who have been successful in Boston ‘giving back’; of their money, of their energy, and of their time.” 

Two closely related sub-questions were, “How do we encourage startups to stay in Boston, and not move to the valley?” (Think Facebook.) And, “How do we encourage $100 million companies to grow to be $1 billion companies, vs. selling out?”  (Think Turbine recently selling to Warner Brothers.)

The top five ‘goods’ at Nantucket were:

  1. Bill Warner; walking the walk, talking the talk.  Bill spent every waking hour at Nantucket giving back.  I know Bill from his ambitious early nineties startup, Wildfire.  He took the speech recognition technology I sold him and created a brilliant, useful, way-ahead-of-its-time application for connecting people on their phones.  A few years later when I was at a startup, Bill ‘gave back’ by providing our team with sage advice, resulting in our successfully selling the company before we had to raise any outside capital. 

    At this year’s Nantucket, Bill worked tirelessly to encourage others to join him in such ‘give back’ efforts as the unConference held each fall, and the Angel Boot Camp, to be held on 1 June.  Over dinner, over lunch, or at the breaks, Bill would corral folks – VCs, angels, CEOs – and push for our thoughts on what needs to change so we get more entrepreneurship and innovation in Boston, so we can keep companies here, and so we can encourage founders to not cash out too early.  Of anyone at Nantucket, no one worked harder at this than Bill.

  2. Youngish CEOs.  Sadly, there was only one person at the entire conference under thirty.  Most were well over forty.  But there was a cadre of CEOs (many in their thirties) filled with excitement about the companies they have worked hard to create.  These CEOs were the breath of fresh air at Nantucket.  Like myself, many were paying the $2,500 to attend out of their own pocket; they were already starting to ‘give back.’

    At this year’s Nantucket, an extensive amount of time was allocated to networking so, given these CEOs’ willingness to engage in conversation, I enjoyed learning from Kwin Kramer of Oblong Industries, Paul Andre of MDinteractive, Bill Bither of Atalasoft, Karl Buttner of 170 Systems, Reed Sturtevant of The Awesome Foundation, Bill Shander of Beehive Media, and many others.  Ideally, there should be more like this next year.

  3. More quality time with those who DO ‘give back.’  One of the pluses of my being an interim CEO / COO – I’ve done 10 interim assignments during the last 10 years; 5 times filling a gap after a CEO has exited, and 5 times helping an existing CEO get through a rough patch – is that, between assignments, I get to meet many new people in the entrepreneur community.  These are people of all ages who have had success and who are willing to ‘give back’ of their time and of their contacts, (important to me because all 10 assignments have come via word-of-mouth referrals.)

    At this year’s Nantucket, I was able to spend significant ‘quality time’ with many of these people – some of whom I’ve known for over two decades, some for only two months.  In addition to Bill Warner, these included Don McLagan, Ashton Peery, Matt Pierson, Joe Caruso, Paul Zavracky, and many others. These people were working the crowd hard, introducing themselves to those youngish CEOs, spending much of the three days ‘giving back.’

  4. Jason Calacanis and his controversial views.  Throughout the conference, Bob Metcalfe  (who gave me my second interim assignment back in 2001) could be seen working on his questions / notes for his video call with Jason Calacanis, the last item on the three-day agenda.  Bob’s prep – combined with Jason’s passion – paid off; it was a great session.  Jason is an exciting speaker who clearly articulates his views – on the work ethics of Millennials, on the fundamental ethics of Mark Zuckerberg, on the need for Boston-based successful entrepreneurs to ‘give back,’ and on the problems with our country today.  Jason believes that much (most?) of what ails the US could be fixed through entrepreneurship, hard work, and capitalism.

    At this year’s Nantucket, many (most?) in attendance could be seen cringing at a number of the views Jason expressed.  Frankly I felt he was spot on (though I don’t have a strong view on this.)  It’ll never happen, but I’d love to have a pint with Jason to hear more.

  5. Under-thirties; wait until next year.  John Landry’s VC panel was, as in past years, one of the liveliest.  John is the same as a panel moderator as he is at dinner at home with a few friends; he’s not afraid to ask provocative questions and give provocative answers.  It was during this panel that someone asked for the show of hands that showed that only one person under thirty was in attendance at the conference.

    At this year’s Nantucket, someone suggested that this could be rectified next year if five VCs would donate a total of $10,000 for five ‘scholarships’ to be granted to ‘under-thirties’ for next year.  Four VCs (and HubSpot founder Dharmesh Shah) each agreed to kick in two grand.  I only hope that when the five under-thirties are selected, that preference is given to those who themselves have already demonstrated a propensity to ‘giving back.’  Top of my list in that category would be Jason Evanish, founder of Greenhorn Connect, Cort Johnson, founder of DartBoston, and Apollo Apolinaras Sinkevicius, founder of LeanStartups.

That’s five ‘goods.’  What about that one ‘bad/ugly?’ 

With a well-planned agenda, with plenty of time for networking, and with warm summer-like weather, there was little to complain about.  That said, I was disappointed to see a not-insignificant number of ‘people of power’ who were not ‘giving back.’  Yes, many people – Warner, McLagan, Peery, Pierson, Caruso, and Zavracky come immediately to mind – did spend every break introducing themselves to someone new, making sure they spoke with each of the first-year, youngish CEOs, etc.  Whether VC, angel, or whatever, each of these people was giving back. 

But at this year’s Nantucket, there were some folks – you know who you are, so I’ll not out you here – who remained insular, who did not work the crowd, and who kept to their small group of similar ‘people of power.’  Clearly, their behavior was not demonstrating the ‘giving back’ that everyone said is needed for Boston to compete with Silicon Valley.

Desmond Pieri is an interim CEO & COO for a variety of VC backed companies.  You can find additional posts on his blog called Change Agent.

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