04/19/2011 06:33 pm ET Updated Jun 19, 2011

Epic Summit With the Richard Pryor of Wine, Shark-Tagging & World-Changers All on One Boat!

One of my favorite movies growing up was "Jaws". I'm not sure if that's because I spent most of my summers growing up in West L.A. swimming in my buddy Ricky's pool or boogie boarding with my YMCA friends at Santa Monica Beach, constantly making the cheesy fake shark fin with my hands trying to swim underwater to scare the 12-year-old girl I had a crush on. Or just because it has the most memorable and erie and iconic theme music ever: Duuun-dun, duuun-dun, dun-dun, dun-dun doddila dooh AHHHH!!!

Either way "We're going to need a bigger boat" is one of the most memorable one-liners ever in movie history, and I was reminded of it recently and how it really applies to the success of the Summit Series.

Last week, I was fortunate enough to be among a group of about 1,000 entrepreneurs, non-profit leaders, Silicon Valley gurus, and other rock star types gathered together for Summit at Sea off the coast of the Bahamas. As usual, they had the big name folks attending like Sir Richard Branson (founder of Virgin), Russell Simmons (founder of Def Jam and Phat Farm), Peter Thiel (Facebook board member, early investor and co-founder of PayPal) and Tony Hsieh (CEO of Zappos). They were all wonderfully inspiring. But I want to tell you about the non name-brand folks I randomly ran into, who from my humble perspective were where the true magic of the trip occurred. Watching them do their thing was what reminded me of the "We're going to need a bigger boat" theme, which I'll return to later.

Warning: I may use the word "epic" a bit too much in this piece, but I'll blame it on the culture of the boat for this magical 72 hours. It's like when you hang with a friend who says "Dude" every three words and you return home doing the same thing and your friends are like: "Can you not? Please!"

But other than "Epic!" how else do you describe hanging with Richard Pryor reborn as wine connoisseur Gary Vaynerchuk -- the self-proclaimed future owner of the New York Jets who in the middle of his speech tells a story about challenging an unconvinced client on the ROI on social media by saying: "What's the ROI on your mother!?!" (If you were there you'd be LYAO like the rest of the audience was.)

Or how else do you describe hearing Richard Branson sharing a story about Queen Elizabeth jokingly telling Desmond Tutu he name drops too much? Or Russell Simmons participating in sunset yoga on the port side of a ship jam-packed with conference attendees, just chilling with the "regular" people, unlike a couple of the VIPs on the boat you saw a bit less frequently.

But what was most powerful and "epic" to me as a participant were the organic one-on-one interactions I had very randomly throughout the event -- not pre-arranged, not sought out, just serendipitous connections.

Of course, when I first got there I fingered through the conference attendee list and circled someone from Google I wanted to try to connect with, and someone else I'd probably never get to talk to given their clout, but as soon as we started cruising, the ocean vibe took over and I regressed to the beach culture zen that was my childhood nature -- even making the fake shark fins with my hands. I adopted that "whatever will be" attitude, and wow, did it ever happen!

We went shark tagging -- an important marine study exercise that helps us understand the oceans better and that changed my life! -- with Dr. Neil Hammerschlag from the University of Miami's RJ Dunlap Marine Conservation Program. When it became clear through the pristine translucent turquoise ocean waters that the 11-foot, 800-pound tiger shark was a bit above our novice tagging skills, Dr. Neil lamented it was "too big for the boat" and then did some Jedi Master tagging with the shark still in the water.

Like I said, epic. The rocket round of new and old ballers I got to chill with included Jamie & Chris Kantrowitz, a sister and brother duo who separately have started or led more organizations that I can name, but who are now rocking a new one together called Gobbler.

Or Tammy Camp, an inspiring fellow "Social Chameleon" (think Malcolm Gladwell style taxonomy). Unfortunately, there are very few women in the field of entrepreneurs and Silicon Valley movers-and-shakers, so when a rockstar like Tammy enters the scene, let's just say folks listen. Her latest venture of bridging the investment power of the Middle East with the innovation prowess of Silicon Valley is truly mind-blowing.

She graciously introduced me to another member of the PayPal mafia, co-founder Luke Nosek, who humbly went table to table at dinner one night just soaking up all the vibrant conversations like a sponge. He seemed to be wishing that the bandwidth of his computer like-brain could engage in all the conversations at every table simultaneously. Luckily it couldn't, and our table was lucky enough to draw him in. After chatting with Tammy we were pumped when he joined us and then amazed to see his facial expression was no less than a kid in a candy store trying to figure out where to jump in on the table's conversation.

Then there was the late night conversation with the two marines who were pitching the classy Alex Kerry (not realizing who she was) on their new concept for disaster response -- bridging the gap by uniting military veterans with medical professionals during times of catastrophe. I was floored when, in the middle of the conversation, she turned to me and whispered: "Do you think my Dad could be helpful... should we maybe loop him in?" (I'm guessing she knew the answer to that already but in her humility sought a second opinion.)

Then watching the hilarious "aha" moment the two marines had when they suddenly made the "connection" between Alex's nametag and the fact they had heard veteran and Purple Heart recipient Senator John Kerry's daughter was on the cruise.

Although the random five to 10-minute encounters I had were divine, the real "epic" times came during meals when we were grouped together to break bread at a slower pace. Be it the spiritual significance of that time, or just the fact that it takes at least an hour to have a proper meal, the deeper connections shared between attendees during meal time was extra special.

On the last night of the cruise I ended up at that table with Tammy and Luke, and a few others like Troy Carter (Lady Gaga's manager) and Shervin Pishevar (Founder of SGN). It may have been the best dinner conversation I've ever had, with topics ranging from why American Cheese is the color it is; to the cosmic crime of mandatory sentencing differences between crack and powder cocaine; to middle east culture, hip hop, the end of Freaknik, and why some people have TVs in every room of their homes while others don't own a TV or don't go to the movies -- with the no-movies piece causing the couple of us who live in L.A. serious heart-burn.

As someone whose career has evolved into being an entrepreneur within the philanthropic sector, constantly connecting dots for pro-social change, it was beyond inspiring to share a table and three hours of conversation together. When I'm mostly quiet in a setting like that I know I'm just trying to keep up with the high-powered intellect of this crew and man, I barely talked at all.

Almost two years ago as an aide to President Obama, I helped to host 30 or so Summiteers while serving as the business sector liaison for the White House Office of Public Engagement, so it was a special feeling to see it grow to 1,000-plus change-agents coming together on a three-day epic cruise.

Given all the folks who couldn't make it this year I'm guessing that "we're going to need a bigger boat" theme may be the top item on the agenda for planning the next Summit Series gathering.