A Sunday Story - Data, Dinner and Golf With Friends

Good morning…

I am at the Apple Store in Naples as my trusted MacBook Pro is busted and I might have to buy a new one.

I am testing out the 16 inch MacBook Pro with this post/newdsletter at the store. I love the keyboard and form factor.

It has been a really busy and fun week.

I was in Miami with my partner Matt and Ethan our chief of staff for the Battlefin conference. Matt was seeing old friends from the business and we were catching up on all things financial data and meeting founders.

As I have talked about on the last few ‘Trends With Friends’ the tables may be turning on technology giants using our data as The New York Times sues Open AI and Reddit prepares to go public. As a founder of Stocktwits I have always knows our data was unique and interesting and now with 16 years of data, I am digging in on what it all means in the context of AI.

As luck would have it, my best buddies from Toronto were in Miami for some fun in the sun and I stayed an extra day (Ellen had to get home for work) to grab dinner.

We had dinner at Casadonna out back on the water which was excellent and a fun scene. Heidi Klum was next to us with her daughter doing a lot of photos, but my photobombs all sucked and not worth sharing.

Here are (from left) Adam, Rob, me and Steve (our waiter joined as well) - 200 years of friendship…

My newsletter works in mysterious and glorious ways and my buddy Jack was over in Naples, saw that I was in Miami from the newsletter and invited me to stay an extra day and play golf at the awesome Calusa Pines. I hopped in an Uber at 7 am Saturday and caught a glorious day of golf walking the course.

My game still sucks, here I am pushing a six iron into the water on their signature 16th hole…(yes those are skinny jeans from AG)

I have played there a few times, the last time wearing pants as well…a NO NO In the humidity.

The last time we played we saw a few alligators and this time one of the caddies warned me and told me what I thought was a ‘local legend’ type story of a member that had his finger bitten off by an alligator. I thought it was nonsense and did not bring it up with my buddy Jack…little did I know.

For dinner I asked Jack to set us up at a top fave steak place of mine called ‘Jimmy P’s Charred’. I love this place. Dinner was fantastic.

Jack invited a pal of his, an Orthopedic surgeon ( I do not want to share his name here), to join us and at the end of dinner Jack asked him to tell me about an alligator attack at the golf course that changed his life. Sure enough, my caddy was telling me a true story, and yes the alligator did attack him and I will spare you the gory photos but here he is showing off the middle digit…

I’ve locked down the documentary rights because this story is not over and it is weird, wild and not over. Our doctor pal is still practicing and a great surgeon here in town.

To end the night he took me for a fast ride in his Tesla Plaid which really is an insanely fast and cool car…

Fun week.

I am headed to Coronado to work this coming week.