I Finally Lost My Virginity

This is a two-part Substack—a pre and post deep dive about this upcoming momentous occasion.

Part 1.   It’s a few days before my date, I will admit I am a little nervous and apprehensive, I mean, I really like and admire the guy.  I think he might be my idol.  OK, fine, it’s not sex, but I’ve been invited to Necker Island for a small gathering of CEO’s to discuss ideas which have planet changing consequences.  Other founders like John Mackey of Whole Foods, Shawn Nelson of LoveSac, Bit Coin to Aging issues are being planned. But let me address my obsession with my “man crush” on Richard Branson, Sir Richard Branson!!

As a young entrepreneur, and specifically, a person who is hustling in the music industry in the 1980’s, there are a few iconic titans of that era.   David Geffen, Ahmet Ertegun, Walter Yetnikoff, Chris Blackwell, Seymour Stein, etc.  I believe I shook all of their hands at some event or another and Seymour and I sang Yiddish Broadway hits in a bar in Austin at SXSW decades before he passed.  But Richard Branson was the dude who flew a balloon across the Atlantic, landed by parachute in the middle of London for a record store release and started a fucking airline to the Caribbean because he didn’t like the service he experienced on British Airlines.  He bought an Island in Virgin Islands and just flew into outer space—the man is the ultimate adventurer, an iconoclast, and someone I deeply respect.   

In 1998, 10 years after I started the Knitting Factory wanting to be a “Machur” (Yiddish for “big shot important dude”) in the industry just like Richard, he opened the Virgin Megastore in Union Square NY.  He was coming in to celebrate the opening of the store with a book signing of his latest book, “How I Lost My Virginity” (my rationale for playing with the titillating theme for the title of this piece), So I waited in line to get Richard to sign my copy of the book.  I might have nervously said to him, “I too am in the music biz”, but in the 5 seconds I had, someone next in line was already pushing forward, and he didn’t have a chance to hear my business plan and do a strategic deal or how…….  Moving on.  Next time….

On Sept 23, 2013, City Winery hosted the first Ocean Elders benefit dinner where Neil Young and Jackson Browne performed (two of my all-time favorites each with stories that will distract from this one).    The Ocean Elders are a collective of politicians, philanthropists, environmentalists, and artists dedicated to protecting the world’s oceans from pollution, over-fishing and other ecological threats.  Richard Branson was the main host at the event and I snuck in as the “owner of the venue”.   I got to schmooze with Ted Turner, Prince Albert, Queen Noor, James Cameron among others.  I tried to convince Ted Turner to buy some wine for his buffulo chain of restaurants, but he mentioned having bought several vineyards thinking the same pairing.  Ted understands how to scale!    But my sneaking into this party as the “owner” of the venue was primarily to spend a minute with Richard.  It had been 15 years since our last 5 second encounter and we were meant to be together……Well, it didn’t happen again, I have some level of respect and he was in his element. He had important opening remarks from the stage to take action on our environmental problems, to explain we are near a tipping point of irreparable harm to the ocean if we don’t make immediate changes.  Not time for me to schmooze him with comments about how much I admire him and find him inspiring.  Oh well.  I guess this just was not the right moment, I can wait til we are ready. 

Part 2.  So, now I get invited to Necker Island as part of a small group for a Conscious Capitalism thing called the Principle Summit. I had imagined we will all get there, but Richard will see through all these other leaders, wealth, and philanthropists and identify with me, the one fellow cool music dude who cares about environment, etc.  I psych myself up that at the first dinner, we will sit together and look into each other’s eyes talking about life, perhaps play some chess at one of the many chess boards I discover dotted on the island next to swing sets, giant tortoises, on the beach, or pool side.  Maybe he will pull me over the pickleball, ping pong or tennis court for some conversation while we volley the balls over the nets. 

It turns out, day one he wasn’t there and missed my presentation;  in fact, the conversation was excellent and John Mackey, who talked about his book The Whole Story, asked me several insightful questions and there was lovely smart banter, but where was Richard.  Am I being stood up?  Did he not know I was there, that this one-sided bromance meant so much to me?   

The next morning I woke with the sunrise.  It was beautiful by the reflection in the infinity pool outside my room, slightly romantic, I went down to the tennis court area, ran back up sweaty to the pool and hoovered outside hoping to accidently run into his Sir-ness.  The main house where the set-up for conversations was happening with about 35 people total was so open and comfortable.  The staff and place catering to our every needs.   When the lunch was served at the beach pool and it was a large floating boat of sushi with champagne, I almost forgot about my mission.  Talking about libertarianism while half naked in the pool eating sushi was very distracting and almost so hedonistic that it was ok that my man had yet to appear.  The special nectar of Necker was having its influence, or perhaps it was the sipping rums flowing from the bars everywhere, but the fact I seemed to be blown off by my date with losing my virginity was ok. Fine. I get it.  The photos in the main house coffee area with him with President Obama or Princess Diana hanging in this house, I guess those friends of his are more important.  Well fine, ladi dah dah…

It's now the last day, I’ve resigned the fact the pre-inscribed copy of my book I had for Richard would now need to be given to some staffer to find its way to his bedroom.   My fantasy of playing some tennis, walking on the beach, afternoon chess, and a sip of wine with my idol was coming to a close.  But I got up early again and there he was—my gray goateed man in a tee shirt.  As I was getting my first coffee, so was he.  Already sweaty from playing a few games of tennis shortly before, he was eager to talk to those around the table. I sat across from him, we traded a few thoughts.  He was very interested in what people were doing, where they were from, he had terrific energy.  I gave him my book and he seemed genuinely grateful.  About an hour later, we met again down by the pickleball area, he was finishing up a game there and now playing a set of tennis with a young female prodigy who was running my 74-old date all over the court.  Once that was finished, we then all went over to the large “alligator” dinning table overlooking another pool and the Caribbean Sea, had some lunch and I got to make him laugh when he handed me a napkin to wipe something off my nose, and I offered to hand it back to him, he politely said no thanks, and I said, “no I insist he take my napkin back with my possible bugger on it”.  He gave a big grin, laughed and I told him about our wine bottle exchange at Grand Central Terminal, how we are getting 60% return rate there.  He understood how something like this could impact the 32 billion single-use bottles being used a year by the wine industry.   We all stood, I took a selfie, and he found a way to shoved Shawn Nelson into the pool fully dressed.  It is an apparent on-going thing with him, my new pal, my new bestie, to throw people into pools.  Why not.  If you got pools all around you, may as well throw people in. 

So, OMG, I just hung out with him, talked, joked, and had some intimacy.  I lost my Virginity in the Virgin Islands with Richard Branson, finally.  It will be a lifelong memory for me.  For him, I am just another part of a harem of people he enjoys meeting. Faces, some names, which helps feed his soul.   He has so much stamina.  He gets this 20 times a day.  So damn impressive.   Will I ever get another chance, who knows.  But I feel satisfied enough.  Was it the cherry on top, perhaps.  But I need to learn to relish in what I got, it was a legit enough.  But like Richard, I  always want more.   It’s hard to be perfectly satisfied.  I guess the cherry is elusive on top.