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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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04TH May 2016

Creative problem Solving - Cuba - Explorer - Havana Culture - Incubator - Innovadores - Innovadores Foundation - Interns

I’d like to see what $40k clothes look like…

…Said my favorite designer in Havana yesterday, poignantly nailing the depth of the gulf between Cuban and American cultures. Idania, founder of a Design shop named Clandestina, may have been thinking what I thought; that blouse is like…166 years average salary in Cuba. And she actually said it! Chanel rolled in to Havana yesterday, on the heels of Usher, the Stones, Obama, Conan, and of course the Innovadores. No word yet on Britney or the Kardashians. And while everyone is taking inspiration from Cuban colors and culture, precious few are making something of the same in a way that benefits the Cubans themselves. Obviously, the market for Chanel blouses is a bit thin in Havana, where the average salary is $20.  And while the world has declared Cuba hot hot hot, […]

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20TH November 2014

Choate - Entrepreneur - Grand Central Tech - Leadership - Social - Timely - Venture Capital - Vision

Jesse Fink tonight at Start Up Choate

Tonight we host Jesse Fink, former COO of Priceline and Founder of Mission Point Capital, for the latest edition of our series of fireside chats. Jesse needs no introduction; his career arc was part of a plan, but by his own admission that “happened faster than expected”. This will be our first event in our “home away from Wallingford”, the super start-up nexus known as Grand Central Tech run by Chalie Bonello and Matt Harrigan. Matter of fact, because of the overflow, it has been moved from the 2nd floor incubator up to the 16th floor co-work space called “Grow Grand Central Tech”, where companies land after completing their times on 2. We’ve just sent one of our Vaux portfolio companies, Bell Family, upstairs. In the 18 months since inception, […]

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17TH November 2013

Choate - Creative problem Solving - Leadership - Uncategorized

Chaos and Stability: StartUps need both.

I’m hosting another Start Up Choate event this week, at Applico’s space in New York. It will be the sixth of seven events this year that has united entrepreneurs, angels, and those aspiring to be. This post if for those aspiring to be. I sense a little hesitation from my fellow alumni, wondering if this is a good time to jump in. Many have graduated the best schools, with the best grades, and may be on a track (or have!) the best jobs in the nation. So why is everyone so excited about such a messy way of doing business? Is this just a bubble or is the world changing for real? Let me be clear: startups are chaos at every stage, inchoate to outcome. Everything takes twice as long, […]

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23TH September 2013

Business Tricks - Choate - Creative problem Solving - Mojiva - Social - Timely - Trust Cloud - Uncategorized - Vision

Start Up Choate/Fall ’13… Yes but Why

Note: Choate’s fledgeling Entrepreneur/Angel community begins its roadshow next week in LA and San Fran. To register (sorry: no Deerfield!) try this link.  And as I began planning for our Fall Roadshow this recent post in Wait but Why caught my eye (kudos Woody Marshall for his FB share). It maps out, in quite stark and occasionally hilarious terms, why Gen Y has trouble with happiness: out of whack expectations don’t mesh well with reality. I’ve written before about what I learned at Choate and how it helped me as an entrepreneur and angel. And so before jumping on planes to LA, SF, Boston and NYC for Choate’s Start Up program, I began to imagine what it would take to align expectations and happiness in the world of Start Ups. […]

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10TH July 2013

Angel investing - Timely - Uncategorized - Venture Capital

Angel investing for Family Offices: What if you knew ‘Zuck… back then.

After a few years of hanging around (and learning a lot), Angelo Robles from Family Office Association asked me to host a panel on angel investing. It was based on the Angel investing White-paper I wrote about for the FOA awhile back- still relevant btw! Here’ s a brief summary on who is on the panel, and how to participate. Our first question will certainly be… So here a brash college kid in front of you, a geek savant with zero social skills. Peddling a social network… Do you touch it? And just say you fronted the money; how many ways do you get a screwed along the way? Done right, angel is a beautiful thing. But every success you hear about has a dozen (or more) orphaned peers. <Note […]

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19TH June 2013

Business Tricks - Creative problem Solving - Good Story - Leadership - Mobile - Mojiva - Race to the Bottom - Timely - Trust Cloud - Uncategorized

I am shocked, shocked that there is big data going on in this Establishment

So, the NSA has been snooping the data at most of the big Silicon Valley tech titans, who snoop the data of most of the planet. The former is looking for bad guys, the latter are looking for customers. What’s the diff? What cracks me up is the outrage. It reminds me of Captain Renault’s great line outside Rick’s Cafe the night he shut it down. How did we get to this place? Data used to be such a hard and fast thing. Name, address, and social security was plenty to get a verification going. It worked well for high stakes actions like getting a mortgage, a car loan, a college education… and it still does. The titans of big data and credit have built tremendous businesses based primarily on […]

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