Network News: The Punks & Pinstripes go to Tuscany

A trusted network is something no entrepreneur should be without

Mar 09, 2026

NYC → Mountains → Tuscany

When I (it’s Matthew here) was over in New York last November I met a guy called Greg Larkin1.

Greg came to the meal with 9others in NYC on the Monday and, chatting over vegan pizza, Greg shared what he was doing with Punks & Pinstripes…

Mountain #1

You see Greg used to be a pinstriped investor on Wall Street. He predicted (he says ‘got lucky’) the 2008 financial crisis before anyone else. And since then he’s worked with Fortune 500 companies including Uber, Google, Nestle and many more to launch new, and transform old, businesses. He’s lectured at Columbia Business School and Singularity University. He even wrote a book about how to do innovation and, probably, get yourself fired.

So he’s had some terrific success.

He calls that ‘climbing your first mountain’.

But, he wondered, if that’s done — mountain #1 has been climbed — what’s next? And are there other people in the same boat?

Mountain #2

Greg felt like he needed to get to know, and bring together, people who’d had that first mountain success too. But it turned out that most exec communities were built for people still climbing their first mountain.

Mountain #2 people are looking for different things than mountain #1 people. They’re chasing something, still climbing, but they want more purpose.

Greg created Punks & Pinstripes in early 2020 for people climbing that second mountain — the people who’ve done well (maybe even in pinstripes) but they still want more. These people have a rebellious sense of urgency to define success on their own terms. They’re punks.

And it’s working. The ‘salons’ attract amazing speakers, the ‘Un-parties’ are a blast, and the ‘feasts’ are incredibly helpful (I was a ‘Punk who needed help’ at one that week in November and I’ll never forget it).

To date all events have been in New York…

A retreat to reclaim your creativity

Now, Punks & Pinstripes is coming to Europe. Tuscany to be precise. A 1,030 hectare estate in the rolling Tuscan hills near Pisa.

From 28th June until 4th July 2026 Greg is running a retreat for leaders who want to carve out dedicate time to create in the community of other incredible people.

“We had to bury the writer, the artist, the maker and buy homes, pay for school, and save for retirement. But somehow, that creative fire won’t die. It stalks you when you hear the song, read the book, see the painting, and feel the spark say, ‘I’m still here’”.
— Greg Larkin, Punks & Pinstripes

If that sounds like something you need then you need to get in touch with Greg. His generosity in New York and the calibre of people I met at the Punks & Pinstripes feast were off-the-chart — I have no doubt that this will be an incredible week that will produce incredible results and stay with you for a long time to come.