Entrepreneur, Explorer, Angel.

Sometimes all at Once.

18TH April 2019

Angel Investor - Business Tricks - Family and Friends - Timeless - Uncategorized

Busy is often BS

We’ve been talking an awful lot about work norms. Goldman Sachs no longer requires suits. IBM allows flex time. MasterCard permits video attendance at weekly touch base calls. This is all terribly progressive, and probably helps with attracting, retaining, and motivating A Players. But one thing remains a fallacy; the common safe place called “being busy”. Maybe it’s the old puritan work ethic. Maybe it’s from back in the days when people- most- billed by the hour. Those warriors who worked on weekends. Brought files along on vacations. Always had a conference call, or a reason to burn the midnight oil. How impressive. What a workhorse. Such a team player. An animal. We gave you a pass because you were full on, all day. Frantically moving from one thing to […]

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05TH April 2019

Angel Investor - Incubator - Leftovers - Social - Timeless - Uncategorized

Happy Collisions are actually a Developers Mantra

I don’t write about real estate much- I don’t invest there. But I wanted to write about Clay Fowler and Spinnaker, who have another project going up, along the I-95 corridor in Norwalk- you can’t miss it. I completely love his philosophy of design and space, where he goes out of his way to encourage interesting, curious people from different walks of life to have space for “happy collisions” on a regular basis. I’ve lived and done business in his buildings- which have done a lot to make Sono the cool place it has been for… 20+ years. And each time I return there, I find something new and different. A bakery inspired by Martha’s kitchen. A pool table in the lobby of an office building. A rooftop with community […]

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07TH March 2019

Angel Investor - Family Office - Leftovers - Social - Timely - Uncategorized

Update on the Devils Lettuce

The NY Times had a recent feature on the family behind Charlotte’s Web. Yes, a family story, about the family business. It’s truly amazing how legitimized the industry is becoming, while Opioids have become the pain management whipping boy – this Samantha Bee takedown is epic, and hilarious. I’ve watched from a distance as the cannabis market has growth it’s way across the US and Canada. Well, actually, Canada is totally covered at this point. And it looks like the states are smelling the tax revenue. (I have one CBD investment I manage, and no relationship with the substance in question). I’m not sure where all the health concerns, gateway arguments, and the like pan out, but I’m fascinated by the history of cannabis and the US. I’ also rewarded […]

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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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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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