Entrepreneur, Explorer, Angel.

Sometimes all at Once.

08TH February 2019

Family and Friends - Leadership - Legends and tales - Timeless - Uncategorized

Prisoner AT War. Stoic lessons my Dad taught me.

My Father, aka Big Art, loved to teach us about perspective. He could take nearly any situation, and find some lesson, some thread of good in it. And usually a chance to learn and do better next time. He suffered hardships throughout his life, some by his own hand, but never lost that gift of self awareness and the thirst for improvement. The most extreme example he would give was about a man who would become Vice presidential Candidate under Ross Perot- James Stockdale– and the seven years he was held POW in Vietnam. AOM tels it well; Rear Admiral James Stockdale wasn’t a prisoner of war in that prison camp in North Vietnam. He was a prisoner at war. At war with his captors. At war with his own […]

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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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19TH February 2018

Cuba - Entrepreneurs - Family and Friends - Food - Havana Culture - Leadership - Timeless - Uncategorized

On Celebrations and Cigars

The most appreciated gift I bring home from Havana is cigars. Wrapped by the best hands in the business, they seem to imply… “party coming soon”. I’m told this by aficionados because I certainly am not one. Usually, the reason to celebrate this way is having a baby, closing a financing, manifesting an exit. Sometimes it’s a personal best that takes a lot of work and has a defined moment worth savoring. They also combine very well with Cuban rum, which isn’t a coincidence either. So here’s my offer: tell me about your recent financing, exit, acquisition, or similar entrepreneur or life triumph in 100 words or less, I’ll send you a box of the best Cohiba’s I have. I’ll do it just for the happy story.  

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06TH January 2018

Angel Investor - Cuba - Family and Friends - Family Office - Havana Culture - Incubator - Innovadores - Innovadores Foundation - Interns - Leadership - Parenting

Fire and Fury? Well, Havana’s safe as ever, guys. (IMHO)

I don’t know much about the current book dominating the headlines, except for how it applies to my personal experience in Cuba. Last year, much was made about travel to Cuba being suddenly suspect or dangerous. With nearly a year to look back now, I see a few main themes that may explain 2017: Roll back on any Obama initiative one can find. Lob an unprovable grenade as justification. Even though “Sonic Attacks” sounds more like “Remember the Maine” each day, it got the job – confusion- done well. Exert pressure on Havana citizens by closing the US Embassy and closing off visa applications. This isn’t much fun. Poke the Cuban Military by blacklisting hotels and travel business they control. Since the State Department published it’s “no-go” list in November, […]

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01TH January 2018

Cuba - Entrepreneur - Family and Friends - Leadership - Parenting - Timeless - Uncategorized

An Entrepreneur’s Life

Honestly, it’s been hard to understand it [entrepreneurship] myself, let alone explain it to others.

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20TH November 2017

Angel Investor - Business Tricks - Creative problem Solving - Entrepreneur - Family Office - Good Story - Leadership - Parenting - Portfolio - Timely - Uncategorized

Vaux Founder Profile- Theresa Claire of “Mixed Emotions”

Today, I couldn’t be happier to feature Theresa Claire, Founder of the Mixed Emotions Game. In her first pitch to me, even on the first slide, she told me all the reasons I should not get involved… I’m a solo entrepreneur- and Mom! I’m not the first mover. I don’t have a PhD. to my name. I need a side hustle to make this all work. To which I responded; so what. I tested the game with my kids, their friends, their parents, their teachers… and it totally rocked! Which is not the first reaction you would expect when discussing the subject of card games that teach kids emotional awareness. But here we are, launching a Kickstarter less than a month later and crushing it on social media. Because it […]

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13TH October 2017

culture - Geopolitical - Good Story - Leadership - Timeless - Timely

Hold my Beer- Jacques DeMolay

  On the way to dinner, with Cuban entrepreneurs no less, we got into a discussion of the hex of Friday the 13th, and no one knew the origin. It’s actually an 800-year-old entry in the “Hold my Beer” Series: the name is Jacques De Moulay, last of the Knights Templar. [French King] Philip wanted the Templars arrested and their possessions confiscated to incorporate their wealth into the Royal Treasury and to be free of the enormous debt he owed the Templar Order. Molay was in Paris on 12 October, where he was a pallbearer at the funeral of Catherine of Courtenay, wife of Count Charles of Valois, and sister-in-law of King Philip. In a dawn raid on Friday, 13 October 1307, Molay and sixty of his Templar brother knights were arrested. Philip then had the […]

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07TH August 2017

Angel Investor - AppTaris - Creative problem Solving - Family Office - Good Story - Leadership - Legends and tales - Portfolio - Timeless - Timely

Founder Profile #3 – Tom O’Reilly of Aptaris

(Tampa, FL) My sit-down with Lilly from Fashion Snoops was so much fun I decided to continue with more; it’s one of the most rewarding parts of my work because I believe the talent is in there, somewhere, and it’s just my job to ask questions that bring it to the surface. In the case of Tom O’Reilly, we have an epic story of a scrappy entrepreneur just figuring out how to literally rebuild an airplane while he was flying it. Literally, another story of “Hold my beer, I got this”. So how did it happen? Well, he stuck to the values he learned as a little boy; use the tools of the day to stay in close contact with your customers. Here are Tom’s 5 Questions Question #1; Where’s the DNA from? Miles: Tom, […]

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23TH March 2017

Baseball - Cuba - Havana Culture - Incubator - Innovadores - Innovadores Foundation - Leadership - Timely - Uncategorized

Back from Havana 

I got a memory reminder from Facebook- I generally hate them- but this at least helped me place a watershed moment in Cuban-American relations… the day I met John Caulfield. In the two years since, the Innovadores has blossomed under John and Jono’s efforts, and I have played a small part in assisting them. I’m back from Havana this time feeling so alive with optimism. Ok its measured, long term optimism, but optimism because of how many things progressed in two years. First, the mere fact that I did get a notification on Facebook means there was wifi, with increasing coverage. The fact that we had a dozen investors and entrepreneurs with us discovering ways to work in Cuba seemed unfathomable two years ago. Sitting in on a fabulous diplomatic […]

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07TH March 2017

Good Story - Leadership - Legends and tales - Timeless - Uncategorized

Gladiator is a love story

I like to write about being a man’s man, maybe because I think it’s a lost art today, and it shouldn’t be. Charlemagne had it. So did Bonaparte, despite his complex. Robert E. Lee makes the list. Winston Churchill for sure. But examples of this behavior are so singular today they deserve calling out, even if they only lived on a screen and 17 years ago at that. I remember seeing the movie in Ohio with a friend, and it was so impactful. Which is why today I write about Maximus… “My name is Maximus Decimus Meridius, Commander of the Armies of the North, General of the Felix Legions, loyal servant to the true emperor, Marcus Aurelius. Father to a murdered son, husband to a murdered wife… (you know the rest) […]

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