Entrepreneur, Explorer, Angel.

Sometimes all at Once.

16TH May 2016

Adventure - Choate - Entrepreneur - Family and Friends - Platforms - Timely

Start Up Choate Panel

Chloe and I hosted another Start Up Choate panel, this one at Alumni Weekend in Wallingford. I felt like I was home. The panel was really cool, and diverse. From first-timers to old timers. From old-school tech like Mobile (it’s ten years Alex!) to new stuff like trans-gender HR management (thanks for the heads up Natalie!). Here’s the whole panel: Jordan Bookey ’96, Co-Founder of Zoobean Jordan Lloyd Bookey is Chief Mom and co-founder of Zoobean. Her company’s flagship product, Beanstack, serves as a technology platform for public libraries’ reading programs across the country and in Canada. Formerly a teacher and Google’s Head of K-12 Education Outreach, Jordan is originally from Des Moines, Iowa, and now lives with her family in Washington, D.C. Natalie Egan ’96, Founder of trans.cafe Natalie is […]

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15TH April 2016

Choate - Geopolitical - Leadership - Timely - Uncategorized

Be True to your School… trust is earned daily

I received a letter from my school earlier this month: it was among my proudest moments as an alum. Choate has a long and storied history as boarding schools go, founded in the 1880’s on the British model, form (grade) meetings in Chapel, Blazers and dress code in the dining hall. Truckloads of homework, a rainbow of curriculum options, great admissions to college, and a unique bond that only boarding schools can create. Jack Kennedy nearly flunked out, ee cummings learned his punctuation, and Michael Douglas acted (up) in Wallingford. It’s a pressure cooker, an escalator that goes straight up and you can’t get off but to jump. At least it looks that way from the outside. From the inside, it’s actually a lot more fun for the students (was […]

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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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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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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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