Entrepreneur, Explorer, Angel.

Sometimes all at Once.

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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28TH June 2018

Angel Investor - Geopolitical - Mobile - Parenting - Race to the Bottom - Timely

Ding. Look at me.

Digital addiction has gripped society in less than a decade. The smartphone era dates from Apple’s introduction of the iPhone in 2007… before that, the closest thing to a digital pavlovian response was hearing AOL’s goofy “You’ve got Mail”. Either way, it is a nanosecond in human evolution. No matter what we think we know now, we simply don’t know what the long-term effects of digital devices/smartphones are or will be, any more than generations past could glean the effects of all of those earlier technologies on moods, relationships, and cognitive development. Americans check their devices 80 times per day, which is more often than men think about sex (34.2 times according to Psych Today… I promise). Why? The secret is in the glowing notifications, likes and shares. Psychologists at […]

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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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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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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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13TH January 2017

Angel Investor - culture - Entrepreneur - Fashion Snoops - Food - Leadership - Mobile - Race to the Bottom - Timely - Uncategorized

Looking out, at the world.

“Love does not consist of gazing at each other, but in looking outward together in the same direction.” ― Antoine de Saint-Exupéry, Airman’s Odyssey Exupery has long been one of my favorite authors, and this is one of my favorite quotes. Amazingly, it took me a pair of Spectacles by the soon-to-be-public Snap, Inc. to reconnect with the thought. I think this is a tremendously exciting product, arriving at a moment we actually need a bit of a reset on perspective. Here’s the why: our look-at-me world is a race to the bottom. And the race to the bottom feeds upon the instant gratification that has taken hold of our world. No-one is really to blame. It’s just that hit of Dopamine that has become so addictive in segments of our society: […]

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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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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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19TH May 2014

Business Tricks - Choate - culture - Entrepreneur - Family Office - Leadership - Mojiva - Timeless - Trust Cloud - Uncategorized - Venture Capital

Next Stop: Grand Central

My Mom used to answer the phone at our house : GRAND CENTRAL !@#$%^ STATION. It was nuts with activity; cats sleeping with dogs, kids not sleeping at all, random neighbors, dangerous art projects, three legged bunnies, ninja turtles- with real num-chucks, 1,000 ping pong balls, 60 foot tree swings, snakes in sleeping bags and ill-advised science experiments. It was an incubator of sorts, but all she was able to raise was a bunch of crazy kids and a few Estes Rockets (with pet mice aboard no doubt). The fact that four of us survived to adulthood was testament to her unique no-helicopter policies ( I am not sure how many she started with). To cry about anything short of a compound fracture was simply bad form. Cuts without stitches […]

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