Entrepreneur, Explorer, Angel.

Sometimes all at Once.

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 teach 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 - 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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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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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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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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01TH January 2018

Cuba - Entrepreneur - Family and Friends - Leadership - Parenting - Timeless - Uncategorized

An Entrepreneur’s Life

Honestly, it’s been hard to understand it [entrepreneurship] myself, let alone explain it to others.

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08TH December 2017

Cuba - Grand Central Tech - Havana Culture - Innovadores

How’s it going in Havana? See for yourself.

I’m asked a lot about Havana. I suppose my opinion has gone from rookie observations to a seasoned sophomore at this point- there are so many others here that have lived and learned so much more than me. But FWIW here’s what I see. Sonic attacks are at a bare minimum (haha). Whatever happened, whoever knew, wherever they got that thing… if it existed at all…it is safe to say that no-one here gives it any more credence than the sinking of the battleship Maine. While I can’t make any guarantees, I think it is safe to say the risk of danger from rum overload is probably greater than the danger from sonic attacks. The hotspots are still pretty hot. I once wrote about a list written on a napkin at 304 O’Reilly in […]

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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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