Entrepreneur, Explorer, Angel.

Sometimes all at Once.

23TH April 2020

Creative problem Solving - Entrepreneur - Family and Friends - Mobile - Parenting - Timely - Uncategorized

Hair, in the time of Corona.

We didn’t have a cure for Corona. But it sure had a cure for us. It’s like we were all swimming nicely in warm waters… when suddenly the tide went out, and all of humanity’s stark realities were there on display for most anyone to see. Startling. Hair; We like it more than we knew I probably didn’t think much about hair before Corona. My Dad and Grandfather passed a full head on to me, though Vitalis is no longer on the grooming essentials list. On a regular basis- monthly I’d say- most of us had some version of this routine (for men- women please add steps as you see fit). Call ahead to salon (or spa, or barber, whichever), to see how busy they are. Maybe book a time […]

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20TH June 2019

Entrepreneur - Social - Uncategorized

Is Shark Tank “Real” Enough

It’s been 20 years since I was in the studio for MoneyHunt; not a week passes without the same question… “is that like Shark Tank (previously, Dragon’s Den). I explain the similarities, and the differences, and conclude… all that is worth, like, one Chai Latte at Starbucks, give or take. On MoneyHunt, we were nuts enough to write the check on the air. No broken deals, no weaseling out of agreements on arcane terms. We considered it a cost of business, and didn’t expect much from the outcomes (our expectations were met!). But we did a whale of a job marketing our little VC fund, a seminal outperformer in the dot.com rush. So what people ask me about SharkTank is this: Do they really do what they say they do?  […]

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10TH May 2019

Angel Investor - Culture - Entrepreneur - Family Office - Leadership - Uncategorized

Introducing Incredulous… a little show about cultural shifts, discomfort and opportunity.

Over the past few months, I’ve worked with the best PR firm in the nation, Gregory FCA, to develop something we talk about at the dinner table each night. Incredulous is about culture, emerging trends, generational conflict… and some damn silly stuff we get upset about. Sometimes it’s an opportunity. Other times, it’s just something to laugh about. In this flight… For Boomers, the party never ends! Jimmy Buffett opening a Retirement Home Erasing History at Washington & Lee. Is that really what we want to do? Sign of the Times; Giuliani Gets Booed at Yankee Stadium Duh! English Teacher Corrects White House Letter Trumped; Social Media more powerful than White House visit. Teach your parents well. Mom Fired For Kid’s Instagram Antics FOMO built this. Beanie Babies Empire won’t […]

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30TH April 2019

Angel Investor - Business Tricks - Family and Friends - Geopolitical - Good Story - Incubator - Legends and tales - Social - Timeless

The Black Tulip…springtime flowers, trends & bubbles. Yeah!

Tulip futures, anyone? It’s tulip season around here; The New York Times had a wonderful story today on Rembrandt and dutch tulips. They’re pretty, but I love them for more than their looks… A very special person to me loves tulips. I do too, and I also love them as a reminder of bubbles- financial ones. Tulips are the first great bubble in modern recorded history, as detailed in the wonderful book called Extraordinary Popular Delusions and the Madness of Crowds. It’s an early study of crowd psychology by Scottish journalist Charles Mackay, first published in 1841. It’s still in print, and cited by financial wizards from Bernard Baruch to Michael Lewis. Tulips had quite a run in in the 17th century. As the flowers grew in popularity, professional growers paid […]

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13TH April 2019

Business Tricks - Entrepreneur - Timeless - Uncategorized

We are the Factory

I’ve spent the last two years super optimized on one platform- I can’t believe the increased efficiency, and the decreased anxiety of this move. I credit Don Dalrymple. First, about my work: I mentor startup founders, and I am quite active in that role. Which means I have to be able to plug and play into their systems seamlessly. I do not, hell I can not dictate which conference line to use, which product management tool, which crm, etc. I have to adapt, quickly, to whatever they choose. It used to be maddening, but I flipped that; now I enjoy the challenge of learning how they communicate by diving in quickly, so we can get to the real stuff. Which meant my stuff had to be super organized. It wasn’t. […]

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08TH April 2019

Business Tricks - Entrepreneur - Food - Good Story - Timeless - Uncategorized

Avocados also come with Values!

Entrepreneurs are mad for Avocados- in shakes, on toast, even guacamole. it’s perfect as protein, and even better as a value reminder. Yes, true! I caught Seth’s Godin mention the Avocado principle recently: it’s a well cited mantra in the Bay and especially at 500 where I learned so many incubator scale tricks. It goes something like this: If you wait until you really want an avocado, the market won’t have any ripe ones. You need to buy them in advance. But… If you eat an avocado that’s not quite ripe, you won’t enjoy it. AND, you won’t have a chance to enjoy it tomorrow, when it would have been perfect if you had only waited. If you live your life based on instant gratification and little planning, you’ll either never have […]

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05TH April 2019

Angel Investor - Incubator - 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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28TH March 2019

Entrepreneur - Family and Friends - Geopolitical - Incubator - Leadership - Timeless

Passion can be Painful

I wonder if founders appreciate that the origin of the word “passion” . It’s the Latin word for “suffer.” I didn’t know that until recently, on a Founder touch base call, where a very passionate argument was made and didn’t land. [It makes perfect sense; passion requires a commitment so pure that mere suffering would not deter i]t. I hear about- and see- Founders everyday that are bursting with passion about their product, the problem it solves, and the business they are building around it. Problem is, many forget the suffering that comes with it. So here are a few of the pain points each founder must learn to stomach; Suffer the humility of defeat; by this, I mean the realization that it is time to quit pressing the idea as […]

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03TH February 2019

Angel Investor - Entrepreneur - Leadership - sport - Timeless - Uncategorized

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

Angel Investor - Entrepreneur - Family Office - 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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