Good judgment is rare. Like good taste.

Fast judgment beats fast data.

Today, I want to tell you a story about judgment.

On my podcast Life Sciences Today, I recently hosted Loren Larsen, CEO of Videra Health.

We talked about how their AI platform helps patients make better mental health decisions—at scale, 24/7, without judgment, without fatigue.

But beneath the tech, I found something deeper.
Something more human. More foundational.

Judgment changes everything.

You can’t automate it with agents.
You can’t outsource it to McKinsey.
And when the moment comes—you either have it, or you don’t.

Hear how Videra Health is using AI to support better mental health decisions Creating Value with Videra Health – Life Sciences Today Podcast Episode 8

Read my story of 3 brothers; the man who ran from the mob, the man who built a manufacturing empire, the man who made jewelry on Park Avenue.

From New York to San Diego, the hard way

One built stability. One built systems. One ran for his life—into a new one.

They started in the Jewish tenements of 1930s Brooklyn and ended up in Forest Hills, North Jersey, and Chula Vista.

It’s a story about how our lives flip on moments of judgment.

The present

Bob is an engineer in Silicon Valley. His younger sister Maddie is a professional art-restorator in Boston.

25 years ago

Their grandfather Dave had 2 brothers, Al and Richard. Dave, Al and Richard grew up in Brownsville. It was a tough, poor, mostly Jewish-Eastern European immigrant neighborhood in Brooklyn. Jewish social and political organizations, labor unions and socialist groups like the Bund, flourished.

There was a wedding of a cousin in NYC.

They flew over from the West Coast. The entire family was together for the first time.

Sunday before the wedding, Bob and his sister Maddie found themselves alone with their grandpa Dave and Uncle Al.

Everyone else was out shopping.

Richard didn’t come in for the wedding from San Diego.

Al cooked breakfast for them.

The 4 of them were sitting around the kitchen table in Al and Rosie’s apartment in Forest Hills eating scrambled eggs, bagels and lox with tomatoes sliced very thin. Chocolate milk and orange juice on the table.

Bob, “Uncle Dave and Al. Maddie and I want to hear the story of Richard.

We live in LA and all we know is that Richard lives in Chula Vista. It’s a 4 hour drive from LA, but we’ve never been down there”.

Dave looked at Al. Al looked back at Dave.

Dave, “Al, you should tell our story. You’re the oldest brother. You know the history”.

Maddie, “Uncle Dave, what history”?

Dave, “Ahah Maddie, there is a lot of history and a lot of mystery. Al will tell you the story from the beginning”.

Al, “OK, I’ll tell you our story. Maybe you’ll understand why Richard didn’t come in for your cousin’s wedding”.

Al, “It was the 1930s in New York. The Great Depression.

After 6th grade, we started working to help put bread on the table for our family.

At age 13, I was an apprentice to a jeweler. By the time I was 33, I had my own store on Park Avenue. I moved with your Aunt Rosie to Forest Hills. Your cousins moved out to Jersey and sent their kids to private schools.

At age 13, Dave became an apprentice in a shmata business.

By the time Dave was 21, he was production manager in the factory on 6th Avenue and 34th St.

The factory made women’s shirtwaist dresses. Their dresses became an iconic brand, with the mix of practicality and femininity that defined American women's fashion in the 1940s and 1950s.

The company built distribution channels throughout the US from Macy’s in NYC to Weinstock in Sacramento.

By the early 50s, the company was struggling to manage its production and distribution with index cards.

Dave commandeered a wall in the 36th Street warehouse. Dave painted the wall black, and then painted a matrix of white lines. He made the wall into a spreadsheet with rows for products and columns for retail customers. The cells had planned and actual deliveries. Dave updated the cells every day with white chalk. After 3 months, the company achieved JIT - just in time delivery to the department stores across the country.

Dave was an ambitious kind of guy.

He wrote a patent application for a novel system for JIT production planning and control. The patent was granted and a year later, Dave sold it to IBM.

Being an ambitious kind of guy, he divorced his Brooklyn wife and married Dorothy, a textile designer who worked for Norman Norell. Dorothy brought innovative fabrics and textures into Norell designs including the famous Norell mermaid gowns. She was a class act. I remember. She still is a class act.

With the money from IBM, Dave bought a 50 acre farm in North Jersey. They built a big house in Bergen County with a studio for Dorothy. Her textiles became part of the work of many top fashion designers, interior decorators, and architects such as Frank Lloyd Wright.

The youngest of the 3 was Richard.

Richard dropped out of high school, and went to work as a sales trainee in the shmata business.

By the time he was 16, Richard decided that he wanted to move up in the world.

He knocked on the door of Abraham E. Lefcourt, who was big in developing the Garment District. Lefcourt, originally a newsboy from the Lower East Side, was a big real estate developer, building garment lofts in the area.

Richard told Lefcourt’s secretary that he wanted to work for Lefcourt selling real estate.

She wanted to blow him off, but for his chutzpah, she showed the boy into Lefcourt’s office.

Richard told Lefcourt that he wanted to work for him as a real estate salesman.

Lefcourt told him, “You wanna start working for me kid? You can’t start as a salesman. You start as a partner”.

Richard started the same day, selling lofts on commission.

By age 18, Richard was making $25,000/year, the equivalent of $500,000/year in today’s dollars.

He married Lucy.

Oh man, do I remember Lucy. She was a knockout. Classy clothing. Hats. Gloves. Every outfit is perfect.

They would come into my Park Ave store all the time to buy jewelry for Lucy.

The 2 of them were 19 and living the lush life.

After a year, they started fighting over money.

Richard wanted a divorce but Lucy had her own ideas on a divorce settlement.

Unfortunately for Richard, Lucy Fiorello came from a Mafia family.

Richard ran all the way to the West Coast with Lucy’s Mafioso brothers hot on his trail. They caught up with Richard in San Diego and made him an offer he could not refuse.

It was just after Pearl Harbor. Richard enlisted in the Navy and served 4 years in Naval Intelligence. No one in the family knows exactly what he did in Naval Intelligence.

After the war, Richard married Henrietta. The marriage lasted 6 months and they divorced in Reno.

Richard wanted to restart his life and taught himself art restoration.

He met Carol, a rich divorcee with a big house in Chula Vista. They became inseparable. Neither of them felt the need to get married and they lived together as common-law man and wife for 35 years.

December 21, 1988.

Carol was on Pan Am Flight 103 after visiting a girl friend in London on her way back to NYC and a connecting flight to San Diego. A Libyan terrorist bomb detonated on the plane over Lockerbie in Scotland. All 270 passengers and crew were killed. Including Carol.

Richard was devastated.

They had been together for 35 years.

In California, the man and wife in a common-law marriage inherit each other. Richard inherited Carol’s fortune.

Not that he needed it. Or wanted it. He was making crazy money doing art restoration for crazy rich people in La Jolla and Coronado.

But God was kind to Richard. He sent Sarah to Richard a few years ago and they got married. Sarah saved him from the hell of losing Carol and brought him back to the living.

Every so often, Rosie and I, Dave and Dorothy fly out to San Diego for a week and spend some time together.

We like the weather. It's a lot nicer than NYC.

Dorothy loves Richard because of his work in art restoration. They talk all the time on the phone. He’ll call Dorothy up and consult with her on materials.

Anyhow guys, that’s our story.

I guess that now, you can understand why Richard didn’t come. He’s happy in his own world and he won’t fly”.

In 1988, Bob was 5 years old. His sister Maddie was 4. They were in preschool in West LA. His parents never spoke much about his great-uncles. Dave and Al were on the East Coast and they almost never saw each other. They barely mentioned Richard. Just some vague stuff about a Mafia wife and being married a bunch of times.

Back in LA after the wedding.

Bob, “Dad, Maddie and I wanna go down to Chula Vista and spend a few days with Richard and Sarah. We’ll take the Amtrak and Richard will pick us up.

It’s summer break and we don’t have anything better to do”.

Mr Fogelman (Bob’s Dad), “OK Bob. Go for it. You’re a big boy. Just look after your sister”.

A week later, Maddie and Bob were in San Diego. Richard, in a Hawaiian aloha shirt, was waiting for them.

A big black Lincoln was waiting for them outside Santa Fe Depot train station. Sarah - a petite, jolly, blond-haired woman in her 70s, was at the wheel of the black Lincoln.

Back at the house in Chula Vista, Sarah and Richard fussed over them and got them set up in 2 guest bedrooms.

Richard, “Tomorrow, I have a client coming in. Interesting case. You guys will wanna hang out”.

10:00 AM the next morning in Richard’s art restoration workshop.

A well dressed woman in her early 30s came in.

“Hi I’m Vanessa Sterling, the insurance company gave me your name. I hope you can help me”.

It’s a hot summer day in San Diego. Maddie and Bob watch Vanessa as she walks in.

Vanessa Sterling has a chic and laid-back coastal look. She wears a lightweight, white linen sundress that falls just above her knees, perfect for staying cool in the heat. She’s wearing a pair of oversized designer sunglasses with gradient lenses. Stylish yet comfortable leather sandals, featuring subtle gold accents that catch the sunlight as she walks into the workshop.

Her jewelry is minimal but expensive, a pair of small diamond stud earrings, a thin gold bracelet, and a classic wristwatch with a leather strap.

Her hair is styled in loose waves, effortlessly tousled by the ocean breeze, and her makeup is light and natural, with just a hint of bronzer and a touch of coral lip gloss to accentuate her sun-kissed glow.

Richard, “I’m sure I can. This is my niece Maddie and my nephew Bob. They came down from LA yesterday to hang out with us for a few days”.

Maddie kicks Bob under the table and hisses into his ear, “Stop staring Bob!”.

Vanessa, “We had a fire last week. 7 expensive Japanese paintings were badly damaged by the smoke and water system. I was hoping you could help me”.

Richard, “Yes I can. Your insurance company sent me the information from the policy including the original hi-res photographs of the paintings. Fortunately, it’s mostly smoke damage”.

Vanessa, “I took pictures. You can see them on my phone here. The paintings are all black. I don’t see how you can save the paintings”.

Richard, “Actually I can. What I’ll do is this. I’ll take an infra-red photograph of each painting. I’ll lift up the paint from the charred silk backing and remount the picture on a brand-new silk backing after cleaning of the char”.

Vanessa, Bob and Maddie are looking at Richard. All thinking. This sounds like science fiction.

Richard, “This is a technique I’ve used before and it works very well”.

“Vanessa, have the paintings brought over here. The insurance company pays my expenses. You’ll have 7 paintings, good as new in 3 weeks”.

Vanessa says thank you so much.

She leaves a path of effortless chic behind her.

Over supper that evening, Sarah and Richard are very warm and hospitable with Maddie and Bob.

Bob and Maddie feel perfectly comfortable and at home.

The next day, they meet a few more clients. Richard asks them what their plans are after high school.

Bob, “I’d like to study engineering”.

Maddie, “I’d like to study art”.

Richard, “You know, your uncles and I all started out as apprentices. Sarah and I don’t have children of our own. What do you think about becoming my apprentices?

I’ll teach you everything I know about art restoration.

It’s a great profession. I work when I want to and it’s good money restoring art for crazy rich people like Vanessa. What do you say?”

Bob, “Uh, that’s an amazing offer, but I guess I’d really like to become a software engineer”.

Maddie, “This would be an amazing opportunity for me, if you would teach me”.

Richard, “It would be my honor and pleasure. You can live with us.

Today, after everything I’ve been through, I want to preserve my legacy.

Preserving my legacy is all I care about now”.

The Judgment Premium

Looking at the three brothers' lives reveals something profound about judgment.

• Al built stability through steady, incremental decisions

• Dave saw opportunities where others saw problems, reinventing himself through strategic risks

• Richard lived by instinct, making bold choices that sometimes saved him and sometimes sent him running

Their stories aren't about who was most successful, but how each brother owned his choices. Here's what I've learned about judgment:

Bad decisions can be fixed

Slips in judgment are how we learn

But a decision you don't make? That one owns you

When we defer choices, we surrender control. We become passengers in our own lives.

This applies everywhere: in business decisions about deals or hires, in product development, in personal relationships.

The people who move fastest aren't necessarily the smartest—they're the ones who've developed their judgment through practice.

In a world obsessed with data and certainty, we undervalue this rare asset.

Good judgment isn't about having perfect information. It's about knowing when to move with the information you have.

Better judgment doesn't just help you make better decisions—it accelerates everything else in your life and business. It's the difference between watching things happen and making them happen.

If you'd like to hear more about decision-making in healthcare, check out my conversation with Loren Larsen on "Creating Value with Videra Health" – Life Sciences Today Podcast Episode 8. Loren's insights on using AI to support better mental health decisions mirror what I've found in business: tools can help, but judgment remains irreplaceable.

What decision are you avoiding right now?

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