Life's Big Mistakes

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Josh Baylin was working at Bloomberg News as a reporter in 2003 when he decided to leave to join Legg Mason as an equity analyst.

He was summoned to a meeting with the head of editorial for the Americas. He was told that “leaving Bloomberg was the biggest mistake he would ever make in his life.”

Josh says the comment fired him up to prove that guy wrong. He took the Legg Mason job and then landed an even bigger one with Steve Cohen’s SAC Capital that changed his life.

That manager — the one who told Josh he was ruining his life, the one who pressured him to stay — was me.

This wee, twenty-one years later. we met up for coffee in San Diego.

One of the joys of getting older is reconnecting with people you knew years or even decades before to laugh about things you said or did and marvel at how it all worked out.

Josh did so well at SAC that he could afford to take off a few years snowboarding in Colorado. He launched and ran several startups and started his own quant fund for which he bought two $60,000 Nvidia-powered supercomputers. He regrets not just buying the stock.

These days he manages the Baylin Family Office from Cardiff, just north of San Diego and spends a lot of time golfing, thinking about golfing and building a golf analytics business.

Josh layered an ontological map over directories of physical courses and then leveraged AI to generate detailed descriptions for each hole. His web site — allgolfholes.com — is often the first that comes up when people search Google for specific holes, something golfers do surprisingly often.

Applying AI to detailed data sets can generate amazing insights. For example, Josh said AI can surface and assess which holes golfers struggle with and suggest ways for the club professionals to work with members to improve.

We have become accustomed to a blizzard of data in professional football and basketball games. Now imagine that applied to our own endeavors. We have seen hints of how data collected by Oura rings and Peloton can change our behavior. This will be much bigger.

Josh’s golfing business is an illustration of how generative AI will radically transform our lives by making easily available an unbelievable depth of information.

Josh says he’s been helped in his career by the network of people he met at SAC, an incredibly talented global network.

It’s something that would never have happened had he listened to that manager at Bloomberg.
 

BRIEF OBSERVATIONS

CONTENT MARKETING: The new content marketing is writing original, authentic, accessible, personal stories on social media, especially LinkedIn.

WE KNOW NOTHING: The more you read about animal studies to more you realize we have barely studied animals at all. They are way more complex than we imagine.

THE PERFECT SHOWER: I’ve been waiting for years, and finally I found the most perfectly designed shower. Note the handle on the right side to turn on the water without getting in and getting wet. Why has it taken so long?

PUMPKINS: The size of everything in America is getting bigger.

SAN DIEGO: I was in San Diego this week for a conference. The weather is perfect. The people were nice. The vibes were chill. How lucky are people who get to live here.