Entrepreneur, Explorer, Angel.

Sometimes all at Once.

10TH May 2019

Angel Investor - culture - Entrepreneur - Entrepreneurs - Family Office - Incredulous - 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

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

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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18TH April 2019

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

Busy could, sometimes, just be 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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13TH April 2019

Business Tricks - Entrepreneur - Leftovers - Platforms - 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 - Incredulous - 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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28TH March 2019

Entrepreneur - Entrepreneurs - 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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07TH March 2019

AppTaris - Baseball - Creative problem Solving - Entrepreneurs - Family and Friends - Legends and tales - Uncategorized

Working from Home has its rewards.

Working from Home today… LOL I was working in Tampa last week, visiting a dear friend and successful founder (same guy). Naturally, we chose to meet at the Yankee game. Double bonus- I got to see my hometown Pirates play. Two things struck me as worth mentioning (the score was not one of them). It’s amazing to me how much Hope there is at the beginning. Spring training is a great example of that. Pitchers and catchers report in mid-March, fully expecting to make the team and to make a difference. Teams are there a week or two later, and scrimmages and spring games begin shortly after- probably too shortly thereafter. The weather is great, players smile and joke around. Veterans grab gloves and hats for rookies stranded at second and run them […]

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08TH February 2019

Creative problem Solving - Family and Friends - Good Story - Race to the Bottom - Social - Timeless - Uncategorized

QED and the Bottom Line

I really can’t tell this story any better, and if I did, I would ignore the lesson that the story teaches. So here it is: Near the end of the Eisenhower Administration, the speechwriter James C. Humes was asked to help the president write a short address. After submitting a draft, Humes was called to Eisenhower’s office to discuss. As soon as he stepped into the room, he could tell that Eisenhower had a problem with what he’d written. “What’s the QED* of this speech?” Eisenhower said to him with only a little patience. Humes was confused. “QED,” he said, “what’s that?” “Quod Erat Demonstrandum,” Eisenhower barked. “Don’t you remember your geometry? What’s the bottom line? In one sentence!” Eisenhower was a brilliant man, but a simple and a straightforward one […]

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08TH February 2019

Family and Friends - Leadership - Legends and tales - Timeless - Uncategorized

Prisoner AT War. Stoic lessons my Dad taught me.

My Father, aka Big Art, loved to teach us about perspective. He could take nearly any situation, and find some lesson, some thread of good in it. And usually a chance to learn and do better next time. He suffered hardships throughout his life, some by his own hand, but never lost that gift of self awareness and the thirst for improvement. The most extreme example he would give was about a man who would become Vice presidential Candidate under Ross Perot- James Stockdale– and the seven years he was held POW in Vietnam. AOM tels it well; Rear Admiral James Stockdale wasn’t a prisoner of war in that prison camp in North Vietnam. He was a prisoner at war. At war with his captors. At war with his own […]

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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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