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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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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08TH December 2017

Cuba - Grand Central Tech - Havana Culture - Innovadores

How’s it going in Havana? See for yourself.

I’m asked a lot about Havana. I suppose my opinion has gone from rookie observations to a seasoned sophomore at this point- there are so many others here that have lived and learned so much more than me. But FWIW here’s what I see. Sonic attacks are at a bare minimum (haha). Whatever happened, whoever knew, wherever they got that thing… if it existed at all…it is safe to say that no-one here gives it any more credence than the sinking of the battleship Maine. While I can’t make any guarantees, I think it is safe to say the risk of danger from rum overload is probably greater than the danger from sonic attacks. The hotspots are still pretty hot. I once wrote about a list written on a napkin at 304 O’Reilly in […]

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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

Cuba - culture - Geopolitical - Incubator - Innovadores - Innovadores Foundation - Timely - Uncategorized

Thank you, Donald 

POTUS, you made Havana mysterious again. (Havana, Cuba) Back in the day, Pan Am brought The Rat pack and friends to Havana for some of the best fun in the sun of the 20th century. Nothing since has come close, until Obama ended 55 years of Castro Curfew in 2015. Havana lit up, out of almost nowhere. Thanks to AirBnB, 497,000 Americans visited Cuba in the following year. Restaurants, music clubs, galleries, and tech began to flourish under the “small entrepreneur” permits. Flights were quick, regular, and cheap. Visas were easy to obtain. The path to progress looked pretty direct. Then, the US embassy staff in Havana was cut by half, Cubans were expelled from Washington, and warnings were made based on a mysterious sonic device. Everyone was totally confused at the […]

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01TH October 2017

Adventure - Cuba - Good Story - Incubator - Innovadores Foundation - Timely

What’s up with the Cuba Sonic Mystery?

(Washington, DC) I was at the WaterGate Hotel, the mecca of silly spycraft, just having a burger and catching up with John and Jono of Innovadores fame. The breadth of what their humanitarian accomplishments in two years is pretty amazing, as their regular updates will attest. It has been a breakneck sprint (relatively) since Obama loosened relations with Havana in 2015. The Foundation has sponsored three years of fantastic Cuban entrepreneurs to intern at Grand Central Tech, and everyone has returned to do good things in Cuba. Several have begun to launch businesses, and we stand ready to assist again. But recently, the US Embassy in Havana cut staff 60%, just two years after opening for the first time in 50+ years. Guidelines on doing business- mostly tourism– are expected to further curtail […]

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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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23TH June 2017

Creative problem Solving - Entrepreneur - Fashion Snoops - Timely - Uncategorized

Founder Profiles- Lilly B.- Fashion Snoops

As an angel/operator (new nomenclature, old practice) I (happily) spend a LOT of my time mentoring CEO’s in the Vaux portfolio; it is truly one of the most rewarding parts of my work. I often say the talent is in there, somewhere, and it’s just my job to ask questions that bring it to the surface. With Lilly Berelovich, the talent doesn’t hide much. I sat down with her recently to talk about the mega-trend in our industry, a/k/a “the retail apocalypse”. Because even as creative destruction wreaks havoc, it builds new leaders. Fashion Snoops is emerging as one of them. Here’s a great video of Lilly to explain all that, and here are my five questions for Lilly: Question #1: Is the educated consumer is now the scary-educated consumer? Miles: […]

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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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