September in New England is all about Fall, football, and at least for the last 4 years, philanthropy. On September 23rd, 2010, venture capitalists, entrepreneurs and professional services providers celebrated the 4th consecutive year putting this tournament on.

The goals?

1) Sweat doing one of my favorite sports on one of its most challenging surfaces--

chasing a white ball around a grass lawn where the verb "to bounce" is used only in a relative sense. Imagine a super-high gravity environment where what goes down, stays down. A bit more like dropping a plate, versus bouncing a ball.

2) Compete in teams, with venture capitalists comprising one team, pitted against entrepreneurs, the other team. This brings together the two key stakeholders in the business ecosystem in which our firm operates. OK, so the entrepreneurs always get a bit feisty because they often feel the perceived chafe of the unspoken universal order, "those who have the gold make the rules." But in this format, spicy works. Feisty is good. For further flavor, see video mash-up of the tournament highlights below.

3) Give to charity, and create a collaborative giving engine that may at some point outstrip at least this author's individual efforts.

The supplemental benefits of combining these three above?

1) Sweating couldn't be in a lovelier setting. The Longwood Cricket Club is just a spectacular venue, and again this year we were graced with perfect early Fall weather--blue sky highlighted by brilliant reds of the autumn maple trees ringing the club house and the courts. Sweating somehow is also a whole lot more fun on a tennis court if you play barefoot. Don't try this on hard courts or clay folks. But at Longwood, all 40+ players doffed their togs and got back to nature (photos and video for up close and personals).

2) Competing with VC and entrepreneur teams brings out... well... a prime opportunity for trash talking in the safety of numbers let us say. It's great to get both sides out in a friendly face off, united at the end for a good cause.

3) Giving to charity is something that seems easier the more perceived value is generated (for the altruist), or we receive (for those solipsists). This year's charity was again the Tenacity program, founded by Ned Eames. We heard from some of the at-risk urban middle school children who have found Tenacity a backbone for discipline and achievement in an often keelless school environment. Hearing some of their stories made us all reflect on our paths to relative success, and how those challenges compared to what these children face. The goal was to raise $5,000 or more, and although the P&L is still being cyphered, we either met or came close to the target.

Who won this year? Technically, the Entrepreneurs won when toting up the total games score. However, the VCs took it in a hotly contested 10-game pro set finals match [see score card below]

The VC team was represented by Michael Balmuth of Edison Ventures and Michael Quinn of sponsor Silicon Valley Bank. This fearsome duo faced off against entrepreneurs Bill Stone, co-founder of OutsideGC and Dean Bogdanovic of CounterPath .

No doubt however that all players won in the larger sense what with the weather, the setting, and the collegiality.

Attributions:

To Sung Park who-- as the poster-child for entrepreneurial ideation-- decided years ago to innovate the fundraising process for his son's school. To do this, he cooked up the first VC vs. Entrepreneurs golf tournament we took part in some 6 or more years ago. I asked him if he had the IP locked up on the idea or could I port the concept to the tennis court, and being the philanthropist that he is, he said heck no, it was "open source." Thanks Sung.

To Longwood Cricket Club, who has been a supporter of the event from the beginning, and Larry, the head tennis pro, who makes it a pleasure to orchestrate.

Tenacity's Ned Eames, who's vision and personal tenacity has grown a philanthropic organization that touches thousands of inner-city youth with a caring and purpose driven mission. See www.tenacity.org for more.

To our corporate underwriters without whom the event would not achieve its goals-- Silicon Valley Bank, XConomy, Version 2.0 Communications, the Boston Lobsters, and Microsoft.

To the captains of each team, who were elected in a rigorous vetting process operating under the game principle of "tag, your it!"

And of course, our guests/the players. Getting ~40 or so players to set prioritize their time and money during a weekday afternoon is definitely worthy of acknowledge and appreciation.

And Cristina, no doubt all of us thank you for all you did in helping to pull the event together yet another year!