Entrepreneur, Explorer, Angel.

Sometimes all at Once.

24TH September 2018

Business Tricks - Creative problem Solving - Good Story - Parenting - Timeless - Uncategorized

The Sharpless Method: We suffer more in imagination than in reality

The title quote is from Seneca. I grew up with a different phrase, but it still worked for me: “80% of the sh*t we spend time worrying about never happen anyways” ~Herbert “Sharpless” Spencer And it’s not that these guys were fearless. Rather, they broke down those fears, those worries, those paralyzing doubts and categorized them in bite sized pieces. My grandfather was a rifleman in WW-I; life expectancy in the trench wasn’t too good. But he survived to marry, to have and to raise twelve kids, to send some to college, and to comb the hair of his grandchildren… which numbered like [33] by the time he passed away. This was his system for dealing with worry and anxiety: Name each fear that keeps you up in explicit terms: […]

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20TH September 2018

500 Start Ups - Angel Investor - Entrepreneur - Family Office - Football - Timeless - Uncategorized

Closing? Should be called Opening…

Closing is the most worst name in the financing dictionary. I know, it’s the day or week when money changes hands. Back in the day, Wall Street-ers would hold a dinner and, after the wire went out (or came it) at 4:31pm everyone would head to the bar to celebrate. But the world of start ups, and start up financing is so different! Funnel and Filter – for years, I have had the good fortune of a funnel of opportunities that keep coming my way, and I’m very grateful for every one. I’ve always followed the lead of [Bear Bryant from this epic post]- be nice, be helpful, and be quick about it. When it’s time to apply the filter, I stick to a couple of basic theses described on the […]

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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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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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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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11TH August 2017

Angel Investor - Creative problem Solving - Entrepreneur - Family Office - Platforms - Portfolio - The Way - Timeless - Uncategorized

Vaux Founder Profiles: Brandon DuFour of SHRPR

(Watertown, CT) Today I am talking with Brandon DuFour of SHRPR, fka Next Street, a tech platform for in-person learning driven by personal improvement and curiosity. He also invented the verb “decal-ing”… This is part of an ongoing series of rambling interviews loosely with Founders in the Vaux portfolio structured as five questions. Don’t miss Lilly B. from Fashion Snoops and Tom O’Reilly of Aptaris. Question #1; The Entrepreneur’s DNA Miles: So Brandon, I’m really interested in how you grew up as a kid in your formative years, and what DNA you had in your family or in your neighborhood that contributed to you wanting to be an entrepreneur. Brandon:  So it’s in my blood and in my DNA on both sides of my family. So on my father’s side, […]

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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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30TH April 2017

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

Oh Father, my Father… this is your success.

  I looked through some family pictures on my Birthday, and this one made me think of what my father has given me. He’s given me something more permanent than good hair, and more powerful than money. He’s given me values and meaning, though it took me years to discover that. And when I did, I was drawn to the story of what his father gave him. And the father before him, and the father before him, all the way back as far as Spencer legend will go. This is quite far when you are a Spencer, and you don’t let too many facts ruin a good story, which is the what is about to happen here…   It is was actually deSpenser to start, which means the steward or butler […]

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04TH April 2017

Baseball - Good Story - sport - Timeless - Uncategorized

As baseball begins… Respect

As baseball begins again, all teams have hope. At least for the day. What caught my eye this year was this NY Times story about a kid named Frazier.  Since George Steinbrenner bought the Yankees in 1973, players on the team have been prohibited from wearing beards and long sideburns, and have been required to keep their hair above the collar. In recent years, the policy has been adhered to largely at the insistence of Jennifer Steinbrenner, one of the four Steinbrenner children who now share in the ownership of the team. Call it the Yankee code. Call it old fashion. Call it out of touch with today’s society. But, if you do, keep on eye on the scoreboard: the Yankees’ clean cut locks have been as much a part […]

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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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