Lesson #1 from NYC Hub... Heros, Leaders, and the NYC Generational Gap

After nextNY's Community Conversation on the NYC Startup Scene, I posted what I learned and promised to follow up in more detail.  I'm going to go out of order and slightly alter what I wrote:

"4. Our "heros" have their volume set too low.  We need to put a megaphone
in front of the charismatic personalities of NYC and get them out in
front of more people."

I think there's more to it than this.  There's a generation gap in the NYC tech community that seems to me a lot more pronounced than in the Valley.  Perhaps the big West Coast Venture funds propped up their failing bubble companies longer, carrying the community over the chasm created by the burst.  I was at the GM Pension Fund, an investor in many of these prominent funds, from '01-'05, and saw many funds throw lots of good money after bad in an attempt to return the capital invested from their Vintage '99 and '00 funds.  This allowed the Valley community a much softer landing than it seemed like the NYC companies had.

This really hit home for me because Jerry Colonna attended and really contributed a lot to the conference.  Jerry was a pillar of the tech community in NYC through the late 90's.  He had done a stint as the Editor of InformationWeek and helped co-found Flatiron Ventures with Fred Wilson.  He retired from full time venture investing a few years ago after Flatiron got rolled up into JP Morgan Partners and has spent more time on professional consulting and educational non-profit work.  I was lucky enough to get to know Jerry because he maintained an office at Union Square Ventures and shared our space... but most of the 20-somethings at the meeting had no idea who he was.  Same thing with a lot of the young entrepreneurs I've met through nextNY.  They don't necessarily know the Jason Devitt's, Fabrice Grinda's... people who built real stuff and exited in and around NYC.  I think the same thing when I talk to David Rose, who founded the New York Angels.  David's quite a character, and one of the most passionate people I know when it comes to getting excited about startups in NYC, but many of our members met him for the first time when we did Startup 101 last June. 

This isn't to knock these folks for not participating more in the community of future tech leaders...   Before recently, there hadn't been many opportunities to do so.  Now, we're seeing the growth of not only nextNY, but many tech focused Meetup groups as well.  The NY Tech Meetup has grown from 35 folks at Meetup's offices to 350 folks at the Great Hall at Cooper Union... and has spun off several niche groups as well. 

It is so important for future generations to learn from the experience of those who came before us.  Many young entreprenuers are asking... who are those people?  Are there more Kevin Ryan's out there and who are they?  How do we get them more involved in the community of young entrepreneurs?   

There's also something about NYC tech personalities...    they just don't act like big fish.  Maybe it's the size and scale of NYC that makes people feel like it's just not realistic to be a big fish... so they just go about their business, work hard, and don't worry if everyone knows them.  For example, I always think of the difference between Fred Wilson and Guy Kawasaki.  Fred's a great guy and I loved working for him, but he turns down more public speaking appearances than he accepts and I could never see him writing a book...   He's got all those blog readers in spite of himself and his modest personality.  He would certainly never call himself a guru of anything.   Guy's a very knowledgeable person, but he's a lot more skilled and interested in self promotion than Fred... and hey.. .that has led to success for him and certainly a big name, so more power to him.   It's just a difference of style.  I look at the USV portfolio companies as an example.  There are very few big and loud personalities among the group...  just a lot of smart, hardworking folks with great ideas.   That may be great for their businesses--less distraction--but sometimes, a little hype helps the community.  It gets the kids to stand up and notice that something is going on around them in the startup world and that maybe they don't all have to be Goldman Sachs investment bankers.   

I've met a lot of great NYC tech personalities in the last two years and I wish I could put a megaphone in front of all of them... one that can be heard in the financial strongholds of this city, the city government, the colleges, the high schools.... because right now, I feel like there isn't enough touting and not enough vocal leaders with experience to guide the ambitious young generation around me.