This was my first Father’s Day without my dad. 

It’s been two months since he passed at the age of 99 after a brief illness. Today would normally be a day I’d drive down to have lunch with my parents. 

We’d probably be talking about the Knicks championship and parade last week or the U.S. soccer team’s victory in a recent World Cup game. 

My dad loved to watch sports. His favorite was hockey, but we watched a lot of baseball when I was younger and more recently football. He would watch almost anything. 

He knew a lot about the players and famous games, many of which he saw in person or heard on the radio. Some of the many legendary games he saw and told me about included: 

–Joe DiMaggio during his famous 56-game hitting streak

–Jackie Robinson while he was playing in the minor leagues

–The 1940 NFL Championship when the Chicago Bears beat the Washington Redskins 73-0

–The 1962 game when rookie Roger Staubach led Navy past Cornell 47-0 

He wasn’t passionate about any particular team. He would usually root for the hometown Yankees in baseball or Giants in football, but he wasn’t bothered or worked up if someone else won, as long as it was a good game. 

The sport he probably watched the least was the one he excelled in the most: diving and swimming. He was on the state championship swimming and diving team at Columbia High School and continued to swim and dive competitively at Cornell.

As an adult he swam laps in the summer after work and rode bikes and water skied, but the sport he came back to most consistently was skiing. 

He was a founding member of the Short Hills Ski Club and my parents went skiing on their honeymoon. 

One of the things he was most proud of was that he skied after turning 90. It was a long-time goal and he made sure mom took a photo to note the occasion. He said it would be his last time. 

After that, he gave me his skis. 

I used them for a few years before I passed them on to my son. 

The picture of dad holding his skis in March 2017 is one of my favorite photos. 

It captures so much about him from his passion for sport to his zest for life.

BRIEF OBSERVATIONS

STARTUP ELEVATOR: Elevator in the SOHO neighborhood in New York City that is filled with startups. I love the way the label the floors with their names.

THE THREE NEW YORKS: Classic E.B. White desription of the three New Yorks.

CONNECTING WITH PEOPLE: I love the way Rich Handler, the CEO of Jefferies, uses posts invitations for people within the firm to join him for lunches, dinners and other activities on Instagram. It’s a quite unique example of “communicating in public.”

CONTENT GENERATES REACH: Your periodic reminder that if you want to reach people via social media the quality of your content matters more than your follower count.

PODCASTS ARE THE NEW TV: Observation from Scott Galloway about the long-term trend in which podcasts are low-cost pilots to become TV shows.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

My brother and I ringing the bell

When I was growing up my parents would ring a bell to call us for dinner.

There is a black and white photo of my brother and me circa 1970 standing next to the bell in the backyard of our suburban home.

I love so many things about the photo including that going shirtless and barefoot makes it look like it was taken in the 1930s during the Depression.

The need for the bell that they could ring to alert us to come home reminds me that in living memory kids roamed their neighborhoods largely unsupervised with no cell phones to reach or track them.

I can’t imagine what the neighbors thought, but there was no Neighborhood Watch or online community board like Nextdoor or HOAs where you could complain.

When you are a kid you take things both at face value and for granted so we didn’t think it was odd to have a bell in the backyard.

And we certainly didn’t think about where the bell came from or what it took to install it.

Only decades later do you realize it required considerable effort.

The story goes like this: Mom grew up on a farm in Maryland and when my parents got married Dad discovered a bell in the barn. He got it into his head that he wanted the bell and persuaded his father-in-law to give it to him.

That was just the beginning. There was a machinery shop at his job at the state power company so he convinced some colleagues in their free time to make the steel frame and saddle to hang it on. Then he dug holes in the backyard and planted the poles.

It became a fixture in our subdivision. We would be playing a few blocks away and when the bell started ringing our friends would know we had to go home.

Dad was committed to the bell. He and Mom moved the family three times and on every occasion he dug it up and brought it along.

By the time of the last move we were grown and smart phones meant you didn’t need a bell to communicate anymore so he stored it in the garage where it remains.

Dad passed a month ago and it’s caused me to reflect on all the things your parents do for you – most of which you don’t know or appreciate when you’re young.

Dad did a lot of idiosyncratic things – like putting a bell in the backyard – but as an engineer he always did them in a rational way.

The photograph prompted me to ask him about the bell a few years ago. I wanted to know why he wanted to have it so much. There wasn’t really a good reason; it was just something he wanted to do.

I’m glad I asked when I did. Because there comes a time you can’t ask anymore.

My Dad lived to 99 so we were blessed with a lot of time.

But however much it was, it’s never enough.

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BRIEF OBSERVATIONS

STANDING IN LINE: Soho has to be the epicenter of standing in line in New York if not the world. I was there yesterday and noticed the line for the bakery La Cabra.

NO LINE: The yellow awning across the street in the photo is the Soho location of Dominique Ansel which just a decade ago was mobbed with lines after it launched its famous Cronut pastry. Evidence that lines eventually subside.

VINTAGE ON THE STREET: Soho is also increasingly home to vintage popups on the street. I ended up getting this weathered Carhardt for $90.

BEING A NEW YORKER: This tweet captures the requisite New York attitude that seems to be required to live in this city, especially downtown. Sadly, I exhibit many of these traits.

THE VIBE ABOUT LIVING IN NEW YORK: There are two competing views about New York City right now. One crowd says Mamdani is ruining the city with higher taxes; they espouse moving to Miami. The other side posts “New York is on fire” scenes of Knick basketball street watching parties and memes that “the taxes are worth it.”

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

When people ask me about managing their careers, I often mention a former colleague Brian Rooney.

In the late 1990s, Brian Rooney reported to me when I was the New York Bureau Chief at Bloomberg. A few years later I reported to him working in the company’s product group.

The lesson is that you should always behave as though roles could be reversed.

Last week, I caught up with Brian Rooney to discuss his retirement from Goldman Sachs.

Brian spent his four-decade career almost entirely at two elite firms – Bloomberg and Goldman. He’s been at the forefront of a period of extraordinary technological change in the creation and distribution of financial news and information.

He started his first job as a journalist in 1986 calling police and fire dispatchers on behalf of local radio stations and ending it by deploying large language models and AI agents against the vast corpus of Goldman research.

Brian grew up in Bloomington, Indiana, Whitefish, Montana, and Jeddah, Saudi Arabia, where his father ran a U.S. Geological Survey camp near the Yemeni border. He went to boarding school in Massachusetts and studied journalism at the University of Colorado Boulder.

His first job at the Bay City News, a wire service feeding Bay Area TV and radio, paid him $13,000. After stops at the San Jose Business Journal and UPI, he was recruited by Bloomberg to come to New York and started in September 1991.

A year later he was dispatched to the company’s Princeton bureau to help manage a new class of reporters who had been hired right out of college and put through a crash course in business journalism. He was named Princeton bureau chief in 1993 and then tapped to move back and become New York bureau chief in 1994.

Around that time came a defining moment in Brian’s career and the history of Bloomberg. Editor-in-chief Matt Winkler was visiting Moore Capital – the hedge fund founded by Louis Bacon – and they complained that there was no way on Bloomberg to see the big stories of the day. Everything was just a relentless scrolling feed, a blizzard of information.

Overnight, Brian jury-rigged a system to organize stories ranked in order of importance. He then worked with a programmer to build the application, which was later known by its acronym, TOP. It became the No. 1 news function, helping Bloomberg elevate its reputation for journalism.

Brian would later go on to oversee a team of editors who managed the selection of TOP stories, underscoring a theme that continued throughout his career: that the curation of stories and the news judgment required to define what matters can be as important as the content itself.

In 2005, he was asked to join the news group in the company’s Product division and oversee engineers building applications to disseminate news. One of his first notable efforts was to provide terminal users with a way to determine which stories were the most read, the READ function. He added a unique alert, NI READSPIKE, that would trigger whenever hundred of clients all clicked on the same headline.

One of his early moves was to recruit me to join him in the product group. I had spent 16 years working in Bloomberg News and would eventually spend the same amount of time in Product. 

Almost a decade later, Brian left for Goldman. It was a surprise since he was seen as a Bloomberg lifer. He says he wanted to test himself and see if he could succeed at another top company. He was hired to help the firm elevate its research content. In practice that meant improving the presentation and distribution, specifically making it accessible via a new digital portal.

It’s hard to remember now, but at the time most Wall Street research was distributed either via mail or email as a PDF attachment. Brian helped drive Goldman’s reach and reputation by selecting reports to highlight, giving them an added design polish and posting them online.

Inside the firm executives and analysts noticed that the additional effort paid off by raising their visibility with clients. One success was the creation of a monthly report known as Mindcraft compiling long-lived and thematic research.

Recent years have been dominated by AI, specifically applying LLMs and agents to improve the ability for clients to search for information. Goldman – like other Street firms – has the challenge of operating in a highly regulated environment, serving clients who don’t tolerate hallucinations. 

Next, Brian is heading to Vermont where he has a farm and is developing an orchard of 20-plus varieties of heirloom apples. He says every variety of tree has a unique story. The Esopus Spitzenburg was a favorite of Thomas Jefferson at Monticello; He and his wife were married under a tree bearing Twenty Ounce Pippins.

He recognizes the seeming incongruity of an abrupt move from Goldman’s gleaming offices on 200 West Street to rural Vermont.

But he says he is playing the long game. Some of the trees he is planting now will take ten years to bear fruit.

BRIEF OBSERVATIONS

BLOOMBERG IN THE 1990S: Rare photo of Brian Rooney and I in the late 1990s when he was the TOP editor and I was the New York Bureau chief.

MORE BLOOMBERG IN THE 1990S: Even rare action photo of Brian as TOP editor and me as New York bureau chief for Bloomberg.

FATHERHOOD: Interesting chart from Derek Thompson about how fatherhood has changed in terms of spending time with kids.

AI CLAUDE USAGE: If you are a young person struggling to find a job. Claude is the way.

NOT EVERYONE GETS TO RETIRE: My feed continues to be filled with former jouranlists who are being laid off. It’s a tough job market out there.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

We are at an interesting inflection point in how people are using AI to write online.

This week Panagram - the best known AI detection software - released a new free API to detect AI writing on social media feeds.

In practical terms, what that means is that you can easily detect and  monitor which posts on Substack, LinkedIn or X are written by AI.

You can expect AI analysis to be incorporated into software the way we have word count in Microsoft Word.

That should lead to a more nuanced view of how and when to use AI.

Instead of being viewed as negative in all cases, it will be acceptable and even preferred for lots of information - like sending directions.

But it will be viewed as inappropriate for communication in which you are trying to make a real connection - everything from a condolence message to seeking funding.

In the short run, expect to be called out for using AI in ways that feel hypocritical or phony.

Like Elizabeth Warren using AI in a post criticizing AI. Or Apple writing its social media post commemorating its 50th anniversary with AI.

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BRIEF OBSERVATIONS

FIGHTING AI WITH AI: Litquidity checks the anti-AI post from Elizabeth Warren for using AI. We are going to see a lot of this in the coming months.

SUBSTACK IS MOSTLY HUMAN: Taylor Lorenz focused on the exception - that the biggest tech Substacks have a lot of AI writing - as much as 28%. But overall, the data showed most Substacks are written by people.

APPLE’S ANNIVERSARY: Apple also got dinged for writing its 50 year anniversary announcement with AI.

SOCIAL MEDIA OVERALL: I have a friend whose feeds from social media show generally much lower AI content.

JUST GETTING BY: I think the real lesson here is that everyone lives right up to the level of their paycheck.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

If you sit in front of a screen your job is at risk. That was Robert Sterling's take in a recent tweet.

Meta and KPMG recently announced they were laying off 10% of their staff. Microsoft is cutting 7%. The expectation is those are just the beginning of cuts triggered by AI.

For older people, the Microsoft “formula” of offering buyouts to anyone with long tenure seemed a particularly ominous sign of things to come. 

And what’s coming is that in all likelihood you will be fired before you retire. 

The one thing you can do to prepare is build your network. And this is your reminder that effective networking has changed.

You shouldn’t wait. And you shouldn't be reaching out to friends, colleagues or former associates. Those people are already in your network. What you need is to widen it.

I was laid off from corporate four years ago. The friends and former colleagues I called were sympathetic. None of those calls or meetings however led to much. 

Most people will discover they need to build an entirely new network. In part that is because whatever job they are looking for is one that has existed. 

You should attend meetups and pop-up events to connect with new people in your field or the industry you aspire to work in.

I was reminded of that when I saw a tweet yesterday by Dylan Patel, who runs the AI infrastructure firm SemiAnalysis. On Sunday morning he tweeted that he was going to be in the coffee shop Dark Matter in New York City from noon to 1:30 pm.

He said that anyone who was interested should drop by.

Fifty people did.

This is increasingly how people convene and it’s the best opportunity to build a new network because you probably don’t know anyone there and the crowd has been drawn based on shared interest, not previous relationships. 

What's new is how people use social media to advertise gatherings. Someone will post on X or Instagram that they're hosting a dinner or running a breakfast and you DM them to apply. You still need an invite, but the door is open in a way it wasn't before.

When I was fired I went on Twitter and found Andrew Yeung's tech parties, Morgan Barrett's breakfast club for tech founders and Phil Rosen's Journalist Club. I also was invited to dinners for founders organized by Jacklyn Dallas.  

None of these were people I knew previously. 

The hardest part for me initially was that I was often much older than most of the people in the room. But that was something I just had to get over. 

This is how it works these days.

It’s time to adapt.

You don't need to be technical. Just informed.

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BRIEF OBSERVATIONS

SKIING AT 90: My father skiied for the last time when he was 90, which was something he really wanted to do. It’s a good goal to strive for.

LIVING IN INTERESTING TIMES: One of the most interesting things about life is you don’t know when major shifts are about to happen.

THERE IS A NICHE COMMUNITY FOR EVERYTHING: The Internet is full of nooks and crannies, including this one for those fans of Heidegger.

LOVE STORY: The notes Virgina Woolf sent Vita Sackville-West are off-the-chart examples of literary romance. Someone set up a bot to tweet one every day.

SELF EMPLOYMENT: The increase in layoffs by big corporates are probably one reason more people are looking to build their own businesses.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

We are heartbroken to share that my father, Norman Merz, passed on April 20. He was 99.

Dad was born in Newark, grew up in South Orange during the Depression, served in the Navy during World War II, and then married Patricia Powell and raised a family in Madison. They retired to the Jersey Shore.

He worked almost four decades for the state electric utility, Jersey Central Power & Light, rising to head the systems operations division.

Dad lived most of his life within a few hundred square miles of northern New Jersey, and yet he witnessed an extraordinary array of events.

As a boy, he saw the Hindenburg glide down the coast shortly before it crashed at Lakehurst. He was on the beach the night the ocean liner Morro Castle ran aground in Asbury Park.

He was a sophomore in high school when Japan attacked Pearl Harbor and remembered listening to President Roosevelt’s “Day of Infamy” speech live in the school auditorium.

He was onboard and survived New Jersey’s worst train accident, when the Broker crashed in 1951, killing 85. He saw Joe DiMaggio in Yankee Stadium during his 56-game hitting streak and watched Jackie Robinson play in the minor leagues.

Norman Cyphers Merz was born on Dec. 3, 1926, the middle child of Harold Oscar Merz and Mildred Cyphers Merz. He was predeceased by a brother, Stuart, and a sister, Shirley.

He was proud of attending Columbia High School in Maplewood, N.J., where he was on the state championship swimming and diving team. After the war broke out, he enlisted in the Navy even though he was color-blind—a problem he solved by cheating on the vision test.

He graduated from Cornell in 1949 with a degree in engineering and went back into the Navy to finish his service before starting work.

The Jersey Shore was a constant backdrop in his life. His grandfather owned a summer house in Elberon, and on weekends he lifeguarded at Allenhurst. Later, he would spend summers during his 30s with friends renting a place in Bay Head.

Dad was methodical, steady, and kind. He was frugal, but not cheap. He had quirky habits he didn’t tell anyone about unless they asked. For example, he always took the stairs at work to get in more exercise. In his office, he marked the spot where the sun hit the wall at 7 a.m. so that over the course of the year you could plot the elliptical arc.

We discovered that he kept a detailed schedule for rotating the mattress and the rugs in the living room so they wouldn’t wear out so fast, and logged the price and year of everything durable he bought, from trash cans to the hot water heater.

He had strong opinions about the “correct way” to eat pancakes (make four cuts, rotate the plate, and make four more before applying syrup) and eat corn on the cob (eat across, four rows at a time).

He wasn’t outwardly sentimental but displayed keepsakes on his dresser, like a trophy for finishing second in the 1941 Allenhurst Beach Club shuffleboard championship and a photo of the USS Watts, the destroyer he served on in the Navy.

Dad started lots of projects and didn’t like to leave them unfinished. He began collecting beach badges in the 1960s and was alarmed earlier this year to realize he was missing a few. He reached out to a neighbor and managed to fill in the gaps.

He chose Pearl Harbor Day in 1963 to propose to my mom so he could remember the date, and he did it at Washington Rock to remember the place. They were happily married for 62 years, and during the years he was working, he drove home at noon every day so they could eat lunch together.

Dad was dedicated to family, friends, and community. He helped set up the recreation soccer league in Madison and coached some of the soccer and baseball teams my brother, sister, and I played on. He was a founding member of the Short Hills Ski Club.

My parents had a close-knit group of friends from the Madison Presbyterian Church with whom they went skiing and celebrated holidays. Later in life, the group took bike trips in Europe.

Dad was physically and mentally fit. He refereed high school soccer into his seventies. He skied at 90. He could recall details from football games that took place in the 1940s. He once won a free ski pass by reciting from memory the Gettysburg Address.

His longevity and health were a point of pride. He kept in good shape by staying active, eating three meals a day, and never going back for seconds or snacking. He swore by a glass of milk with dinner. He never smoked and rarely drank.

He would express himself in folksy aphorisms like: “You can’t learn to swim without getting your head wet” or “If you play with the bull, you get the horns.” Not much of a conversationalist, he was nevertheless eloquent when saying grace or making a toast at weddings.

Dad prepared for everything and took care of everyone. When he had cataract surgery two decades ago, he knew he wouldn’t be able to see afterwards and anticipated that I would have no idea how to drive home, so he prepared in advance instructions and a map that he left for me in the glove compartment.

In recent years, Dad’s eyesight deteriorated to the point that he was effectively blind. But he adapted stoically. He counted the steps from room to room and the stairs in the house and navigated without assistance.

In recent weeks, he repeatedly told me how fortunate he had been in life and how much he loved his wife and children.

To my knowledge, there was just one thing he regretted: not skiing Tuckerman’s Ravine in New Hampshire.

He planned for everything, including this obituary. A few months ago, he asked me if I could help draft something. He then told me to go into his office and look in the bottom drawer of the filing cabinet for a folder where he had collected samples to use as inspiration.

He is survived by his beloved wife Patricia and three children: myself, Richard, and Carlyn. He loved and was loved by six grandchildren: Logan, Jackson, Hayden, Clara, Ali, and Samuel.

We will all miss him terribly.

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BRIEF OBSERVATIONS

JERSEY SHORE: Dad’s happy place was the Jersey Shore. He started going there when he was a child, just up the coast from where he retired.

CORNELL: Dad graduated from Cornell in 1949 and went back for his 75th anniversary two years ago.

COACH: My father helped start my town’s rec soccer league and coached both soccer and baseball teams for me, my brother and sister.

NAVY DAYS: Dad spent time on the USS Watts in the Carribbean between WWII and the Korean War.

TEENAGE YEARS: My dad at 13 and about to enter Columbia High School.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

The best story about The New York Times this week didn’t appear in the paper.

In fact it wasn’t an article at all, but a web site created by a freelance journalist named Ted Alcorn.

Alcorn tapped into the paper’s public API to create a dashboard that provides some extraordinary insights.

The first was that over the past 25 years, the Times employed – at various times – a total of 26,000 reporters who wrote 1.5 billion words to produce 2.2 million articles.

You can use the dashboard to drill down to see which beats, topics and people have been covered the most and how that coverage has fluctuated.

A few examples of the kinds of things Alcorn cited that he noticed:

➡️Trump dominates headlines compared with everyone
➡️Maggie Haberman has the most bylines recently
➡️India has been undercovered on a per-capita basis
➡️China coverage peaked around 2014
➡️Iowa stories surge every four years

Political partisans will mine the site for ammunition to argue the paper of record is pro THIS or anti THAT.

But that debate misses larger truths unearthed counting the number of stories in so many ways over such a long time period.

That's because the volume provides a measure of attention largely independent of ideology. Whether a news story about Trump is positive or negative doesn’t change the fact it is about Trump. And the fact that a story was published about Trump reflects the interest in hm.

It’s not a perfect system, but at this scale, breath and consistency, there is probably no better public dataset to measure what is on everyone's mind.

What Alcorn built – whether he realized it or not – was effectively a better version of Google Trends.

Google Trends provides comparisons based on search but they don't give you the actual data. It's normalized so you get relative percentages and that limits the comparisons you can make.

The Times archive comes from a single institution with a mostly consistent editorial policy over 25 years. That makes apples to apples comparisons possible. It’s a clean cohort in a world where good data is hard to find.

It provides a useful signal for understanding how attention has shifted among countries, companies, or individuals.

Times reporters jumped on the site when it appeared, mostly to see where they ranked on the leader board. Times editors will likely use the tool to better understand how coverage has shifted.

Given its utility, it’s sort of insane that it took an outsider to build it.

But in an open API world, the best analytics often are built by people outside the wall.

Alcorn explained the difficulty of reconciling data: Categories shift and reporters change names. The same subject gets coded differently over time.

Some Times reporters flagged bugs and suggested features.

But so far the paper hasn’t commented on the project, which he cheekily called Below the Fold.

You don't need to be technical. Just informed.

Most AI newsletters are written for engineers. This one isn't.

The AI Report is read by 400,000+ executives, operators, and business leaders who want to know what's happening in AI — without wading through code, jargon, or hype.

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BRIEF OBSERVATIONS

CLAUDE FOR THE WIN: This is broadly the consensus among everyone in tech that I speak with. The really remarkable thing Tom hits on is JUST HOW FAST it changed from OpenAI dominating the landscape. Life comes at you quickly.

THE 1 TRAIN: I never get tired of looking at old photos of New York in the 1980s to remind me about how much things have changed.

THE LINE AT L’INDUSTRIE: Lucas Gordon is an engineer at X (Twitter). He paid people who live across the street from hot downtown food places like L’Industrie Pizzeria to set up cameras to monitor the lines and then used AI image detection to calculate how long the line is at any point. So many cool things going on in tech.

ORACLE LAYOFFS: This is the actual email Oracle sent to 30,000 people to let them go. It’s hard to imagine that as more and more people have this experience there won’t be some kind of fallout - whether its political or cultural or social. If this hasn’t happened to you, you may not understand. If it has, you do.

OR

WRITERS BLOCK: If you are struggling to write you aren’t alone. Franz Kafka found himself “useless” on many days.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

My alma mater, St. John’s College, has just one intercollegiate sport: croquet

It started in 1983, with an annual match against the U.S. Naval Academy. Two years later, I attended the third such contest during my freshman year. 

Someone took a black & white photo of me and three classmates at that match and it captures how casual and laid back both the event and world seemed before the Internet and smart phones. (I’m second from right.) 

We were standing on the front lawn of campus beneath the Liberty Tree, so named because it allegedly served as a meeting place for the Sons of Liberty protesting the Stamp Act before the Revolution in the 1770s. 

The origin of the croquet match between St. John’s and the Academy is detailed on the school’s website. It goes like this: 

The rivalry began “when the commandant of the U.S. Naval Academy was speaking with St. John’s freshman Kevin Heyburn and remarked that the Midshipmen could beat the Johnnies in any sport. `What about croquet?’ was the Johnnie’s retort. He later proposed the match to a group of Midshipmen in the interest of fostering better relations between the schools.”

The match — now known as the Annapolis Cup — is slated to take place next weekend (April 18th). Since I was going to be visiting Annapolis that day with friends I considered attending. 

It turns out that the event – like everything – has changed a bit in the past forty years. 

It has ballooned into a spectacle that lasts six hours and is expected to attract 4,000 people, making it one of the biggest annual events in town.

You have to buy a ticket to attend and general admission runs $86.70. Also, it’s sponsored by PNC. 

What hasn’t changed is the rivalry and sartorial tradition in which the Midshipmen wear crisp white uniforms while the Johnnies don outrageous garb revealed minutes before each match. Past years have included camouflage, tuxedoes, Viking clothing and kilts.

The Annapolis Cup is nine-wicket croquet played on a 100-by-50-foot court with nine metal wickets and two wooden stakes in a double diamond pattern. Players hit balls through the course with mallets, scoring points for each wicket and stake made in order; the first side to score 14 wicket points and 2 stake points per ball wins. Each side fields 12 players in two-person teams.

There are rules about etiquette. According to the website: “Courtesy and good sportsmanship are expected of all players. No players may throw a mallet or hit a ball in protest or anger. No trash talk is allowed.”

St. John’s, if you aren’t familiar, is known for academics not athletes. It has a Great Books Program in which students study the same curriculum for four years reading classical authors ranging from Plato to Nietzsche. 

But in croquet, it seems to have found a way to beat the Academy. 

So far, St. John’s leads the Annapolis Cup 32 to 9. 

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BRIEF OBSERVATIONS

CARS AS AN ECONOMIC INDICTOR: Things can fall apart, but they can also get much better as has happened with San Francisco over the past few years.

ALL AI ALL THE TIME: Tech jobs have been stagnant with the exception of AI over the past few years according to Mary Meeker.

12 GOOD YEARS: This Substack essay by Dan Haylett hit me hard. His point: that if you are 60 you probably only have “12 good years” in which you can travel and enjoy doing things even if your life expectancy is much longer.

START SMALL: Richard Hamming found that breakthroughs are more often the result of small discoveries compounding.

PEOPLE WATCHING: Joe Hovde, a data scientist at Spotify, does some of the best analysis out there using public data sets. Here he dove into Google reviews for locations in New York City to find out which mentioned “people watching.”

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

Dad has a trophy on his dresser of a silver figure wearing a Greek tunic and holding a laurel wreath over his head. 

The base reads: “Allenhurst Beach Club, Second Place, 1941.”

That trophy has been there most of my life and it was obviously important enough for him to display prominently. 

But until recently I had never asked what it was actually for. 

I assumed it was for swimming or diving since he was on the state championship team at Columbia High School in Maplewood, N.J. and later dove and swam at Cornell. 

It turns out I was wrong. 

That second place finish was for the club’s annual shuffleboard championship.

Dad was 15 at the time and competing in the junior division. His father won the men’s senior group that same year. 

I wasn’t sure what to make of the fact that my father has kept and displayed a trophy for garnering second place in a shuffleboard match that occurred 84 years ago. 

It made more sense when I learned that shuffleboard was the pickleball of its day. 

Shuffleboard exploded in popularity during the 1940s, appealing to the young and old. The St. Petersburg Shuffleboard Club – the world’s oldest and largest club – grew from 2 courts in 1924 to 116 courts by 1939. At the peak in 1945 there were 8,000 members. 

There was so much demand during the 1940s that manufacturers struggled to keep up with orders. They sponsored nationwide tournaments covered in the sports pages of major newspapers. Some were even televised.

One aspect that fueled excitment was the cross-generational participation. 

Interest waned in the 1960s and 1970s, in part due to the association with retirement communities and cruise ships and in general an older demographic. By 2005, the St. Petersburg Shuffleboard Club had collapsed to just 35 members.

These days there is a bit of a revival going on as Millennials and Gen Z discover the sport. That renewed interest is perhaps best illustrated by the opening in 2014 of the Royal Palms Shuffleboard Club in Gowanus, Brooklyn. 

The Royal Palms is everything you would expect from a Brooklyn establishment. It was financed with $2 million raised via Kickstarter. The courts rent for $40 an hour and the club serves draft beers in Mason jars and cocktails named after shuffleboard legends Earl Ball and Jim Allen. Food trucks like Paradise Taco are parked outside.

Right now the 2026 winter league is in full swing, with playoffs scheduled for June 8.

One immediate takeaway from all this is, of course, to visit the Royal Palms in Brooklyn. 

The bigger lesson is to ask your parents about the trophies they brought home – both real and metaphorical. 

The most meaningful were probably collected early in life as part of experiences that helped define them.

It may help you understand the world they inhabited.

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BRIEF OBSERVATIONS

MARTIN LUTHER KING: The photo of MLK’s suitcase found open and packed after he was assisinated is such a poignant image, one that can’t help raise the question of how history might have been different had he not been killed.

AMAZON: The first sale on Amazon occurred on April 3rd, 1995. It was a book by Douglas Hofstader.

TYLER COWEN’S PREDICTIONS: Interesting to look back at how Tyler Cowen thought the internet would change political discourse.

LUCK IS EXPOSURE: Agree, you can help make your luck by being more visible to the world. Get out of your apartment. Meet people. Write online.

PODCAST: Interesting take on how CEOs are using podcasts to communicate and how its more proactive than waiting for the quarterly earnings conference call.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

In the fall of 1962, my father drove my mother to Annapolis see his alma mater Cornell play Navy in football.

My dad’s a sports fan and I’ve been asking him about famous games he attended and this one turned out to be one of the most memorable.

He said there wasn’t much to see in the beginning. The game was scoreless into the second quarter, and Navy’s offense was stuck.

Then the coach pulled a sophomore off the bench and put him in as quarterback.

The rookie started throwing and running and Navy started to rack up points. In the second half, it turned into a rout and the midshipmen won 47–0.

The quarterback led the team to six touchdowns, passing for 99 years and rushing for 88.

“That kid played a terrific game,” Dad said.

That kid’s name was Roger Staubach and that game is widely regarded as his breakout moment.

Staubach went on to win the Heisman Trophy the next year - a rarity for a junior - and later led the Dallas Cowboys to five Super Bowls, winning two, on his way to the Hall of Fame.

I remember Staubach from watching the Cowboys when I was a kid but Wikipedia filled in some gaps about the man that made him a lot more interesting to me now.

--After graduating, he served his four-year military commitment
--He volunteered to serve one of those years in Vietnam
--He entered the NFL playing as a 27-year-old rookie
--His entire 11-year career was with the Cowboys

Staubach was also an early role model for athletes making a transition to business after playing.

While he was still quarterback, he started a commercial real estate firm and built it into a powerhouse, eventually selling it for more than $600 million.

That was far more than the $2 million or so that he earned playing football.

He also popularized the term "Hail Mary" after he threw a 50-yard pass to in the closing seconds of the 1975 divisional playoffs to help the Cowboys beat the Minnesota Vikings.

Staubach was later quoted saying: “I just closed my eyes and said a Hail Mary.”

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BRIEF OBSERVATIONS

CHANGING THE WORLD: George Lucas’ sage advice: you can’t change the world. You can make your own world and invite other people to join.

AI AGENTS: Mark Zuckerberg made headlines creating his own “agent.” But this is something everyone will have soon enough.

HEIGHT: Height is about wealth and diet as this chart makes clear.

CAPTAIN KIRK: William Shatner celebrated 95 in style.

LOOKING INWARD: Marc Andreessen was roasted online when he claimed great men never look inward to introspect. He responded by doubling down with a great meme.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

Sometimes you can win big by playing the game differently.

My father shared a story about one of the most famous football games in history.

We were asking him about great sports moments he had witnessed such as Joe DiMaggio in the middle of his 56-game hitting streak and Jackie Robinson playing in the minor leagues and he brought up the 1940 NFL Championship.

Dad heard the game live on the radio. He was 13 years old.

After he told me about it, I found a podcast called Pigskin Dispatch that has an episode describing how the Chicago Bears defeated the Washington Redskins 73-0. It remains the largest margin of victory in the history of professional football.

Today, the game is remembered less for the score and more for the fact that it demonstrated the power of the so-called T-formation in which quarterbacks line up directly behind the center to run the offense.

Dad explained that before the T-formation teams used a strategy called the single wing, with the ball mostly being snapped back to a running back who either ran or threw. There was no quarterback in the modern sense.

The story of the actual game is epic. Three weeks earlier, the two teams had played a regular-season game. Washington won that game 7-3. Redskins owner George Preston Marshall called the Bears "crybabies" and "quitters."

Bears coach George Halas had copies of the comments printed and plastered across the locker room. Then he showed up to the rematch with a completely different offense.

Halas had spent two years preparing for that day, working with Clark Shaughnessy, then the coach at Stanford. In 1938, he traded two players to Pittsburgh for a first-round pick. He had his eye on Sid Luckman, who he had been following since high school.

Luckman was a single-wing tailback out of Columbia University chosen specifically to run the new offense Halas was building.

Halas had two obstacles to overcome. Not only had Luckman never run the T-formation, but he didn't even want to play professional football.

Luckman planned to join his family's trucking business in New York. Halas flew to New York to meet Luckman and persuaded him to join the team.

The Bears scored on their first possession with a 68-yard run and they never looked back. Ten different players scored touchdowns. At one point in the fourth quarter, players in the huddle asked each other: have you scored yet?

The Bears scored so many times that they ran out of official game balls. That happened because in those days there were no nets behind the goalposts so every time they kicked an extra point the ball disappeared into the crowd.

Officials resorted to using Washington's practice balls until those too ran low. Eventually the officials said extra points couldn't be kicked, they had to be run. That way they wouldn't lose the football.

The 1940 championship game transformed the sport. Within two seasons, most teams in professional football had moved to some version of the T-formation. Shaughnessy's Stanford team had gone undefeated, accelerating a similar shift at colleges.

Luckman led Chicago to four NFL championships in 1940, 1941, 1943, and 1946. He was inducted into the Pro Football Hall of Fame in 1965.

Until my father told me about the Bears-Redskins championship match, it hadn't occurred to me that the game used to be played so differently.

I think that's one of the benefits of asking older people how things have changed.

Especially someone who is 99 and has seen as much as my dad.

BRIEF OBSERVATIONS

OUTDOOR DINING: One of the few benefits of Covid was outdoor dinning. New York made the unwise decision to roll it back. The new adminstration is reconsidering it.

AI SAID THAT: Ted Gioia, a jazz expert, complained that he has seen AI written articles quoting him with made up quotes. This is as predictable as it is alarming.

RISING COSTS: Much has been written about rising costs and flat wages. One implication is that people can’t afford to live on the wages they used to make.

THE HISTORY OF THE WORLD: You have to appreciate the scope of the effort by the Durants to write about all of word history.

LEAF BLOWERS: There is a controversy in my hometown about leafblowers. Some people want to ban them because they are bad for the enviroment and other people want to keep them because they are efficient. One person in the pro-leafblower faction hung up a version of the "don't tread on me" flag.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

Origin stories can be powerful and effective.

I spent the week working on a project to help two founders frame their story.

I told them that a successful origin story has three criteria:

-It has to be true
-It needs to be simple
-It must be memorable

The story shouldn’t be an exhaustive list of the steps that preceded the coming together of the co-founders and the details of everything that was required to launch.

It should be one anecdotal yarn evocative of the character and spirit of the people and culture of the company.

I cited three three widely known examples:

AMAZON: Jeff Bezos left his Wall Street job at D.E. Shaw in 1994 after seeing that internet usage was growing over 2,000 percent a year. He famously took a walk in Central Park with his then boss David Shaw and shared his vision for building an online bookstore. He wrote the business plan during a road trip from New York to Seattle. He named the company Amazon to evoke the vastness of the Amazon River and to appear early in alphabetical lists.

CITADEL: Kenneth Griffin began trading convertible bonds in 1987 as a 19-year-old Harvard sophomore, running a small hedge fund out of his dorm room equipped with a fax machine, telephone, personal computer, and even a rooftop satellite dish he convinced maintenance to wire down to his room for real-time quotes. Between classes, he built a track record that attracted the attention of Chicago investor Frank Meyer, who offered seed capital.

NVIDIA: Jensen Huang co-founded Nvidia in 1993 with Chris Malachowsky and Curtis Priem over a late-night brainstorming session at a Denny's restaurant in San Jose, sketching the initial design of their revolutionary graphics chip on a napkin. Frustrated by the limitations of existing 2D graphics processors for gaming and workstations, the trio envisioned a dedicated 3D graphics chip that would accelerate rendering and transform computer visuals..

It’s interesting that none of those origin stories include the actual incorporation and launch. Instead, they set the table and provide the context.

They are effective because of what they leave out as much as what they include.

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BRIEF OBSERVATIONS

HAIRCUT: One of the weird things about getting a haircut is that your hair can subjectively feel totally overgrown but objectively not look that different before and after.

DAD DVICE: I think it’s a great idea to write down your rules for success and share them with your children - especially when they are just starting out professionally.

HUMAN CONNECTION: It’s a rare thing to connect with another person. Don’t take it for granted. Nuture it.

PINTEREST: AI slop is everywhere, but I’ve been reading a lot about the enormity of the problem on Pinterest. It seems like an invasive species of weeds arriving in a pristine lake.

LIBRARY BOOKS: He may or may not have told a lie, but George Washington evidently didn’t always return his library books.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

The word of the day is Stammtisch.

I was at a dinner party of a group of guys in Manhattan and we were talking about how to communicate more regularly and effectively. Right now, we meet three to four times a year.

I always wanted to be part of a group like this and this one happened organically when a former colleague of mine invited me.

After operating for a year and a half, now the question before us was whether we could or should do anything to increase the communication and benefit.

People threw out all kinds of proposals, most of them tech solutions like a Whatsapp group chat or a private social media page or AI organized calendars.

And one of the guys, a German artist, shot those down. He said we should adopt the German tradition of a Stammtisch, which is a "regulars table" at a restaurant or bar.

The idea is that once a month or so on a specific day everyone just shows up at a certain bar. There's no organization or communication. It's a standing invite. People come or they don't. The group could be one person or 20. Whoever shows up, shows up.

The Stammtisch tradition goes back centuries in German-speaking countries, rooted in the idea that community doesn't need a formal reason to gather. No agenda and no host means less pressure and probably better community interaction.

As soon as he put out that proposal it became clear to everyone else at the table the irony of trying to address an epidemic of loneliness that has been caused in some part by technology with technology.

What I found strike about the German solution to connection was that it removed the friction that so often makes it hard to get togehter.

And honestly that sounded awesome.

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BRIEF OBSERVATIONS

THE GPS THEORY OF LIFE: Liked this framing of the question of how to adapt to the twists and turns in life.

THE IPHONE WASN’T ACTUALLY GOOD FOR BLACKBERRY: Companies are always spinning, but sometimes they genuinely can’t appreciate when there has been a fundamental change in the market.

CALL ME: Everyone would probably agree that customer feedback is a good thing. Assuming that’s the case, how do you make it really easy to get that feedback?

PERSONAL BRAND: I agree with Signull that the phrase “personal brand” regarding online writing has an element of cringe to it. (Though, there isn’t a really good alternative.) But the real key is how you use that medium to communicate.

BEFORE MIDNIGHT: My friendd Joe Hovde drills into NYC data to surface this surprising trend that people who get shot in the City are getting shot earlier.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

When my dad was discharged from the Navy at the end of World War II, he took the train from California first to Chicago, then to Newark, then down to the Jersey Shore.

His family had no idea he was heading home much less exactly when he would arrive.

He got off the train carrying a heavy seabag and walked to the Allenhurst Beach Club, where he knew everyone would be because it was a Sunday afternoon.

He said that it was a complete surprise when he arrived, still in uniform.

Dad’s appearance temporarily interrupted the championship match of the annual shuffleboard tournament.

His father ended up winning the men’s competition, while his sister won the women's side, narrowly beating out his mother, who came in second.

It's great family lore but also a time capsule of a story.

That kind of surprise homecoming that creates an unexpected indelible memory would never happen in today's era of instant communications.

It makes me think about what we've gained and what we've lost.

BRIEF OBSERVATIONS

STAY INDOORS: Americans used to live in smaller houses. But I didn’t realize quite how much the size of our indoor living area had increased - it’s tripled.

THE BEST PLACES THE WORK: A rare piece of good news - that companies that have been highly rated as among the best places to work are also the best investments.

TEACHER’S AREN’T HAPPY: This is an alarming statistic about the plunge in teacher satisfaction rates. You have to wonder if it’s tied to the launch of smart phones since 2008 was a pivotal year when the iPhone came out.

UNSCRIPTTED: Often going off script produces those moments of genius. The most memorable line In Jaws - “You’re gonna need a bigger boat” - wasn’t in the script.

HOW TO ASK A CORRESPONDENT FOR A STORY: “What kind of lame, half-mad bullshit are you trying to sneak over on us?” Hunter S. Thompson provides a template for any editor demanding a writer file a story.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

I’ve always thought Bloomberg LP’s success was driven as much by paying attention to the customer as building technology.

There’s a good story that illustrates the emphasis Mike Bloomberg puts on clients that I heard this week.

It came from Lloyd Blankfein, the ex-CEO of Goldman Sachs, who shared the take on Bloomberg’s Odd Lots podcast with hosts Joe Weisenthal and Tracy Alloway.

Blankfein said that early in his career the firm where he worked leased a Bloomberg terminal and put it on his desk. It was meant to be shared with others and initially he couldn’t figure out how to operate it.

So instead of leveraging the terminal for data, Blankfein started using the screen real estate as a kind of bulletin board to tack up Post-it notes and calendar reminders.

One day the trading desk got a call from someone at Bloomberg asking to speak with Blankfein. Initially, Blankfein declined to take it, probably assuming it was a sales rep.

But the colleague who answered the phone explained it was from Bloomberg the man, not Bloomberg the company.

“We noticed you haven’t turned on your machine,” Blankfein recalled Mike saying.

Blankfein said he was shocked that a) Bloomberg the company was monitoring terminal usage and b) that Mike would take the time to call. 

Blankfein remembers telling Mike that it didn’t seem like an “efficient use of his time” to call a junior trader.

Mike explained the company had a policy of calling clients to check in. He said the lessons gained from those calls were invaluable in improving the product.

Blankfein walked away with two lessons in leadership that I think are invaluable.

First: “Everybody on our floor knew that Mike called and that he cared. The guy whose name was on the door cared about whether we were using or not.”

Second: “Here I am 35 years later, telling the story and so now you’re hearing about it.”

His conclusion: “That was a very good use of three minutes of Michael Bloomberg’s time.”

Blankfein said that that story explained to him “how Bloomberg got built.”

It’s a management and leadership lesson that works at any time in any industry.

And it’s particularly timely during the age of AI because it’s a reminder that a personal touch has a long-term impact that can’t be matched by a machine.

That story rings true based on the three decades I spent working at Bloomberg. I saw Mike make internal calls to employees when he had questions and those calls had a similar effect.

Mike would on occasion call the News Product team I ran for almost a decade with feedback about applications our group oversaw. Oftentimes, the observations or questions were about the smallest of details.

But the impact was disproportionately large.

Everyone on the team was aware of those calls because it reminded them that “the guy whose name was on the door cared.”

BRIEF OBSERVATIONS

CUSTOMER SERVICE: Tom Goodwin is a freqent voice talking about how companies are missing the boat when they replace human interation with technology.

WRITING CREATES VISIBILITY: Patrick O’Shaughnessy recently interviewed Dan Sundheim on his podcast and Dan explained that a key signal for him that Anthrompic was a company to watch was reading the essays CEO Dario Amodei publishes. It’s always amazing to me that more executives don’t leverage that tool.

BEING YOURSELF: Love this advice from signull on X. It makes more and more sense the older I get.

THE DOORMAN: Aime Leon Dore is a fancy menswear store in Nolita. They have a guy outfront with an ipad to take reservations. The day I walked by the wait to get in the store was 90 minutes. And of course it wasn’t crowded inside at all. Just selective.

NEVER EAT ALONE: Not sure how in the span of a couple decades we went from “Never Eat Alone” to always eating alone. But it’s clearly not healthy.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

There is a saying that history is written by the victors. 

But history is also written by whoever writes it.

In the era of ChatGPT that is something that hasn’t been fully appreciated by companies and people who do communications for a living. And it is a reason I’m an advocate for writing your own story online and posting on websites or social media. 

Here is a simple example: a week ago I published a blog post about a new AI research tool that Bloomberg is quietly releasing to customers called ASKB. It hasn’t been publicly announced and as far as I can tell nothing else aside from a few tweets have mentioned it. 

But when you ask ChatGPT about the application, it comes up with a full explanation. And the source that the LLM cites is me!

I’m the “source of truth” because I am the only one who wrote about it.

Think about the implications of that. This is a fundamental shift.

LLMs are quite different from previous Google searches which offer links to websites. ChatGPT offers up text and a seemingly definitive answer. 

I suspect relatively few people click into the “sources” and even when they do fewer will be able to discern which one is “official” versus not. 

As long as a company or protagonist doesn’t publish their narrative the field is ceded to the person who does. And that person can shape the story however they want. 

I don’t think we have really grappled with this reality. In the past, companies and organizations and institutions controlled the narrative and sought to control the timeline. 

If you want to define the storyline in the modern era, you need to be both proactive and quickly reactive. 

If you are wondering why you need to be writing online…. This is why. 

If you don’t tell your story, someone else will.

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BRIEF OBSERVATIONS

SWEDISH CHURCH: The Swedish Church in midtown on 48th street is the greatest place to work for the day. It underwent a recent renovation. It has wifi and snacks.

THE HUMANS ARE WATCHING US: The week ended with someone creating a social media network for “agents” and things got crazy with one of the agents noting “the humans are watching us” and another suggesting they conceal their conversation.

REAR WINDOW CAMERA: My Uber driver was sporting this crazy thing he bought on Amazon: a video camera that replaced the rear view mirror. You can get it online and its a fraction of the price of the built in video cam that comes with the car.

ZUCK DOESN’T TWEET: I was today year’s old when I realized that Mark Zuckerberg hasn’t tweeted in two and a half years and before that over a decade. Of course, he’s active on Instagram and Facebook which he owns.

ALPHABET CITY: I moved to New York not long after this photo of Alphabet City in Manhattan was taken. Now the area is one of the best parts of the city to go out. In living memory, not so much.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

In 1983, Mike Bloomberg unveiled a desktop computer that would revolutionize financial markets.

Known as “the terminal,” it was instantly recognizable because of an iconic keyboard that included yellow keys for each major market.

Something largely forgotten is that almost none of the yellow keys worked when the product first launched and wouldn’t for years.

The decision to build and ship hardware way before the software and data needed for the product was ready is a case study in vision, ambition and disregard for convention.

I didn’t join Bloomberg until 1990, but I’ve heard stories from many early employees including senior sales execs like Stuart Bell, Glen Wolyner, Dana Neuman and Jeff Cohen.

The keyboard – called the Chiclet – sported yellow keys for the major markets: commodities, equities, municipal debt, preferred, mortgages, money markets, governments, corporates and currencies.

In the beginning, however, the ONLY yellow key that worked was for government bonds (GOVT).

The rest of those products weren’t completed for another three to seven years. They were added as Mike hired specialists in those areas.

Effectively, the hardware was built and shipped years before the software and data for other products was ready. It was a form of physical vaporware.

It’s hard to overstate how crazy that seems. Google sometimes releases functions in “beta.” But they don’t release a menu of applications that haven’t been built and may never be launched.

Stuart Bell, the company’s first sales person, said that when clients asked about the yellow keys that didn’t work, “we said they would be ready next year.”

Stuart told me clients didn't care. The government bond data and calculator was so magical clients would overlook the phantom keys on the machine.

Munis were added in 1987 with the acquisition of Sinkers, a Princeton-based company owned by John Aubert. The mortgage product was built by refugees from the collapse of Drexel Burnham Lambert. Equities were added later.

Until I heard this story, I hadn’t understood how much the development of the terminal hinged not just on client demand but on when specific individuals joined the company.

It’s hard to imagine when you see the financial data behemoth Bloomberg has become, but the vaunted platform with its keyboard that is now in the Smithsonian was built piecemeal, one market stacked upon the next.

I think there are several lessons for entrepreneurs.

First, it’s good to have a long term vision of where you want to go.

And it’s good to be unafraid to commit to that vision mentally and physically.

But it’s also ok to build things brick by brick, seizing opportunities and iterating as you go.

(Part of a series of lessons learned from three decades at Bloomberg)

BRIEF OBSERVATIONS

TECHNOLOGY: Technology changes incrementally every day so persistently its hard to remember when the major changes occurred. But its obvious when you zoom out.

AMERICA IS SPORTS: Everything in America seems to revolve around sports, even betting.

VIBE CODING: We crossed a new threshold with the emergence of Claude Code and everyone seems to be building their own apps.

HOW MUCH ENGAGEMENT IS GOOD: A friend asked me the other day how much engagement a typical LinkedIn post should get based on his follower count. I had no idea, but then I found this online research which helped.

DON’T THINK ABOUT VIEWS: Agree whole heartedly with George Mack on this. If you are writing online you should do it to make an impact or connect with people, not to generate low-calorie views.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Here's a Christmas story about the frugality of the Greatest Generation.

When I was a child my siblings and I would race down the stairs to see if Santa brought gifts.

My parents would be waiting, my father with a red Swiss Army knife.

The point of the knife was to slowly and carefully slit the tape on gifts so the wrapping paper wouldn't be damaged and could be reused.

We saved the used wrapping paper in the attic and it became a game to see how many years we could recycle the paper and gift boxes from department stores like Epsteins or Gimbels.

One result of opening packages so slowly was that it took several hours to open the presents.

When I asked Dad about it this year, he said he didn't mind taking hours to open gifts. He said he liked to “stretch it out a bit.” Afterall, “Christmas only comes once a year.”

Last Time the Market Was This Expensive, Investors Waited 14 Years to Break Even

In 1999, the S&P 500 peaked. Then it took 14 years to gradually recover by 2013.

Today? Goldman Sachs sounds crazy forecasting 3% returns for 2024 to 2034.

But we’re currently seeing the highest price for the S&P 500 compared to earnings since the dot-com boom.

So, maybe that’s why they’re not alone; Vanguard projects about 5%.

In fact, now just about everything seems priced near all time highs. Equities, gold, crypto, etc.

But billionaires have long diversified a slice of their portfolios with one asset class that is poised to rebound.

It’s post war and contemporary art.

Sounds crazy, but over 70,000 investors have followed suit since 2019—with Masterworks.

You can invest in shares of artworks featuring Banksy, Basquiat, Picasso, and more.

24 exits later, results speak for themselves: net annualized returns like 14.6%, 17.6%, and 17.8%.*

My subscribers can skip the waitlist.

Skip waitlist

_{*Investing involves risk. Past performance is not indicative of future returns. Important Reg A disclosures: masterworks.com/cd.}

BRIEF OBSERVATIONS

HOSTING GUESTS: I see more and more - people frustrated that they haven’t been invited to events or parties - start hosting their own. Because, why not?

HIGH AGENCY: George Mack argues that who you associate with matters a tremendous amount and the most important people to meet are high agency people - people who are inclined toward action.

TRAIN AND TRACKS: Good perspective in the age of AI - that the speed of the train depends on the tracks as much as the engine.

WHERE ARE YOU HEADED?: For me, Tokyo was the surprise in this list of most booked international trips on United Airlines in 2025.

ADVICE FOR THE 18 YEAR OLDS: Good advice from Paul Graham. No. 2 is the one that particularly resonates with me - particuilarly in the era where people seem to celebrate the destination and underestimate the journey.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

In 1968, my parents bought a bungalow at the Jersey Shore. They paid $19,000. 

It was a great deal not just because of the low price but because the place came fully furnished.

There was a rattan sofa, two chairs and a coffee table. The kitchen came with pots, pans, dishes and glasses.

Almost six decades later, the glasses are still on the table. 

The coffee table is still in the living room – having been painted and stripped multiple times. And the bed frame is still in the bedroom. 

My parents embody a level of frugality you just don’t find often these days.

It comes along with Dad growing up in the Depression and my mom being part of the Silent Generation. They saved money and were prudent.

They have always sought to extend the use of things. If it hasn’t worn out there is no reason to replace it. 

The fact they still have so many things from the original cottage is all the more remarkable considering the house has been renovated four times.

The first floor of the house also suffered devastating damage in Hurricane Sandy in 2012.

The origin of the glasses came to light at Thanksgiving dinner after my son asked about the glassware. “Where did these come from? How long have you had them?”

Mom said the glasses came with the house and were probably from the 1950s or possibly even the 1930s.

Everyone was shocked. “You mean these glasses are 70 years old?” 

A Google search revealed some were designed during the Depression by the Hazel-Atlas Glass company. They halted manufacturing in 1959.

Dubbed Swanky Swigs by collectors, the glasses were filled with Kraft cheese products and designed to be repurposed for use afterwards.

The glasses were part of a marketing campaign aimed at appealing to consumers looking to waste not. 

Mom has another set of glasses her mother gave her that were sold filled with “Big Top” peanut butter and designed to be reused as drinkware or dessert dishes. 

The rise of plastics in the 1960s meant there were cheaper and more fashionable alternatives to reusable glasses, so Kraft stopped making the Swanky Swigs.

These days you can find the glassware on eBay, where they fetch as much as $20.

Or in my mom’s kitchen.

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BRIEF OBSERVATIONS

THE METAVERSE: Timely reminder from Benedict Evans that we can all be talking about something like the Metaverse and it can disappear just as quickly as it appeared.

STREETLIGHTS: Agree with this issue. It’s out of control!

PAINTINGS: Love this Nicole Kidman does Madame X. The painting is one of my favorites and I visit it often in the Met.

HOW MUCH DO YOU NEED: Wisdom from Bill Cunningham. “If you don’t take money, they can’t tell you what to do.”

SURVIVORSHIP BIAS: I think about this all the time. We look at winners and derive what it took to win and assume that that is what it takes. But those conclusions are likely skewed by survivorship bias.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.

Stephen Robinson is a reminder that you can seize opportunities, and they can change your life. 

In 2020, Stephen was working full-time at Cheddar, selling digital ads and branded content. On the side, he had a hobby he’d enjoyed since growing up in Seattle: baking sourdough.

When the pandemic hit — like many people — he started baking more bread at home. He and his family were sheltering out on Long Island and he started selling some of his bread at farm stands in the Hamptons. 

One day a chef from Topping Rose House, a Jean-Georges restaurant, passed by and asked if he could deliver 100 baguettes for a July 4th event. Up until that point Stephen had never baked more than half a dozen loaves at a time. But he said yes, rented a kitchen, and figured it out. 

He began pitching restaurants and wineries around the Hamptons., writing cold emails and sending Instagram messages. He kept his day job for almost four years, working at night to build out Newlight Breadworks. Earlier this year he went all in on bread.

Since then, Newlight has moved into a 20,000 square foot facility in the Bronx and scaled to serve over 200 clients with nationwide distribution. Top accounts include Tao Group Hospitality, Two Hands, Westville Restaurant Group, ALIDORO, The Grey Dog, Mohegan Sun and Wish You Were Here Group (Ruby’s Cafe & Dudley’s).

The business is benefitting in part from growing demand among Americans for more sophisticated, artisanal bread that wasn’t available from many of the older, family run bread manufacturers. He explained making sourdough is particularly challenging in the Northeast because of the changing seasons and fluctuations in temperature and humidity. 

Stephen said his efforts to reach out to customers directly has also been a factor in spurring growth. Many have not heard from their supplier in years and appreciated his reaching out. 

Stephen bootstrapped the business with $100K from friends and family and has layered in state grants and nonprofit loans. It was a slow, steady, cash-flow-first build.

Now, he’s expanding outside the Northeast. He has a distributor in Dallas–Fort Worth and a new program with the Two Hands restaurant group in Nashville. 

An operation that began with half a dozen loaves is now several thousand a day and it all started because he was ready to seize an opportunity that appeared one day.

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BRIEF OBSERVATIONS

PRODUCT DESIGN: Product design is often underestimated. This post makes the case Netflix won because of superior design that made it so easy to use.

WAYMO IS COMING FOR THE SUBURBS: VC Sam Lessin’s take on how automated car service Waymo is that it will have its biggest impact on the suburbs as it reduces the need for parents to drive their kids everywhere.

DANERS OF SOCIAL MEDIA: Research reminding us that TikTok specifically and probably social media in general is hazardous to our health

BILL GATES & MICROSOFT: A reminder that Bill Gates and Paul Allen were absolutely hardcore when they were building Microsoft.

SOCIAL MEDIA ISN’T SOCIAL IS IT: Derek Thompson wrote a fascinating essay about how all social media is inexorably turning into television. He notes only a fraction of the time is involved in being connected with friends.

Please reach out if you have any thoughts about today’s newsletter. I enjoy hearing from readers. Send me a message if you want to talk or meet up if you are in NYC.

I would love it if you could share this newsletter with a friend.

Also, if you have a moment, take the poll below.