Entrepreneur, Explorer, Angel.

Sometimes all at Once.

25TH July 2019

Family and Friends - Good Story - Legends and tales - Timeless - Uncategorized - Vision

Squaring the Curve – A Quality Life Right Through the Finish…

My father sold life insurance. Actually, people said they bought life insurance from Big Art. He didn’t so much sell it. He did this by asking questions and listening empathetically. How old are you today? Where do you work? Tell me about your family. Does your spouse work? How many kids? Where are they in school. What sports do they play? Do you play with them? What other activities interest you? How much does it cost you to live here? What do you want to be doing later in life? Do you want to retire someday? Where and how? What do you really love about life? And so on and so on. He insisted on doing it at the kitchen table, with life going on all around. That was the […]

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30TH April 2019

500 Start Ups - Angel Investor - Business Tricks - Family and Friends - Geopolitical - Good Story - Incubator - Legends and tales - Social - Timeless - Vision

The Black Tulip…springtime flowers, trends & bubbles. Yeah!

Tulip futures, anyone? It’s tulip season around here; The New York Times had a wonderful story today on Rembrandt and dutch tulips. They’re pretty, but I love them for more than their looks… A very special person to me loves tulips. I do too, and I also love them as a reminder of bubbles- financial ones. Tulips are the first great bubble in modern recorded history, as detailed in the wonderful book called Extraordinary Popular Delusions and the Madness of Crowds. It’s an early study of crowd psychology by Scottish journalist Charles Mackay, first published in 1841. It’s still in print, and cited by financial wizards from Bernard Baruch to Michael Lewis. Tulips had quite a run in in the 17th century. As the flowers grew in popularity, professional growers paid […]

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03TH February 2019

Angel Investor - Entrepreneur - Football - Leadership - sport - Timeless - Uncategorized - Vision

Communicating with teams in motion

I really enjoy mentoring start-up founders, and I’m happy to call that my avocation these days. Most, but not all, of these founders are young or younger (I took it as a compliment this week when one founder said “we could use some salt and pepper in our founder recipe”). And, with luck and hard work, some of them will grow teams in the hundreds in the coming years, though the majority will not. That’s why I was struck by this interview with LJ Spinnato, a prep school football coach who gives very few interviews, which seems counter-intuitive for a post about communication. But what LJ has done at Choate was inspiring to honing my craft, though most of my kids are a little older and wouldn’t know what “Double […]

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09TH May 2017

Cuba - Geopolitical - Havana Culture - Incubator - Innovadores - Innovadores Foundation - Uncategorized - Venture Capital - Vision

Innovadores and Family Office Association White Paper on Investing in Cuba

I’m proud to say that, two short years after Family Office Association put us together, John, Jono and I produced this sweeping historical overview and going-forward plan for investing in Cuba, which we called “Ready Set Go: Cuba!” . Anyone headed to Havana to discover business opportunities should read it. Those are Innovadores Interns Raynel Gonzalez (GCT Intern Class 2016) and Gabriel Garcia (GCT Intern Class 2015) on the cover. Enjoy the read, and hope to see you in Havana soon! Download the report here.      

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07TH February 2017

Football - Good Story - Leadership - Legends and tales - sport - Timely - Vision

Hold My Beer.

Ok, you are down 25 points in the third quarter. You need to score two touchdowns, two two point conversions, win a coin toss and engineer a touchdown drive to win the seminal event of your chosen profession. A profession from which you were suspended earlier in the year. Ok. Got it. So… Hold my beer. So said a man’s man in last night’s Super Bowl. And then he went out and completely ignored the probability chart. Tomas T. said it perfectly: The problem with predictive analysis like this is they never capture all the variables. They don’t account for great players like Tom Brady can increase their level of play, the emotional swing of a team building momentum, those moments when people enter what Csikszentmihalyi called Flow.  Brady and […]

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25TH December 2016

Angel investing - Creative problem Solving - Entrepreneur - Family Office - Grand Central Tech - Leadership - Mobile - Timeless - Timely - Uncategorized - Venture Capital - Vision

Learn, or give it up to the robots

That pretty much sums up most of the 2017 resolutions I have been seeing from my friends and business relationships. Except for my Buddy Mark, who wants me to do 81 reps of different calisthenics before January 31. In 1998, Kodak had 170,000 employees and sold 85 % of all photo paper worldwide.  Within just a few years, their business model disappeared and they went bankrupt.  What happened to Kodak will happen in a lot of industries in the next 10 years and, most people won’t see it coming. Did you think in 1998 that 3 years later you would never take pictures on film again? If you think of a niche you want to go in, ask yourself: “in the future, do you think we will have that?” and if […]

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02TH June 2016

Creative problem Solving - culture - Timely - Vision

My Buddies from the Future, Snoops

Ok, most of my jeans are cuffed and I often show off some hot socks or bare ankles, depending on the season. Where did that all come from? Well, I recently found out. I have often said, when asked what I do, “I try to visit the future, and build what’s missing”. This ends up just confusing most people. And the fact I am more often wrong than right, statistically, doesn’t help much. But recently, I was introduced to Lilly & the team at Fashion Snoops by a dear friend (I credit the connection to my two year old). I’m in heaven, up ’til now anyways. Snoops (it’s not just about fashion anymore- it’s cars, kids, sports, hotel lobbies) culls the inputs of hundreds of “snoops” spread across the globe, looking for trends […]

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25TH May 2016

Angel Investor - Creative problem Solving - Entrepreneur - Family Office - Leftovers - Timely - Uncategorized - Vision

Protected: Times are changing… so cue the Gummies

There is no excerpt because this is a protected post.

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20TH November 2014

Choate - Entrepreneur - Grand Central Tech - Leadership - Social - Timely - Venture Capital - Vision

Jesse Fink tonight at Start Up Choate

Tonight we host Jesse Fink, former COO of Priceline and Founder of Mission Point Capital, for the latest edition of our series of fireside chats. Jesse needs no introduction; his career arc was part of a plan, but by his own admission that “happened faster than expected”. This will be our first event in our “home away from Wallingford”, the super start-up nexus known as Grand Central Tech run by Chalie Bonello and Matt Harrigan. Matter of fact, because of the overflow, it has been moved from the 2nd floor incubator up to the 16th floor co-work space called “Grow Grand Central Tech”, where companies land after completing their times on 2. We’ve just sent one of our Vaux portfolio companies, Bell Family, upstairs. In the 18 months since inception, […]

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13TH March 2013

Adventure - Business Tricks - Creative problem Solving - Entrepreneur - Good Story - Leadership - Mobile - Mojiva - Timely - Venture Capital - Vision

Yahoo offers a Billion: WWYD?

Yes, Marissa Mayer is out there honing her strategy for a next move, and lots of buzz is around Mobile Ad-Tech. I’m quite keen to those developments, because of my activity in the space… you might say. But before her time, Yahoo made an offer that prompted one of the best “What Would you Do” conversations of our generation. I caught the gist of it at during Peter Thiel’s talk at SXSW, but Inc. does a better job of describing it here: …Facebook was just two years old. It was a college site with roughly eight or nine million people on it. And, though it was making $30 million in revenue, it was not profitable. “And we received an acquisition offer from Yahoo for $1 billion,” Thiel said.    “Both Briar […]

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