Welcome to My Site!

About Me

I’m a devoted husband and father to an awesome family. For work, I’m a Product Manager who looks at the goals of the business and uses technology to deliver those business and customer goals. I’ve driven transformational change at Citi, AIG, and Amazon Web Services. For more information about what I do at work, please visit my LinkedIn profile.

My Writing

If you’re new here, check out my blog highlights. Also, take a look at my library.

My Blog

I collect stories. There are so many amazing things happening every day. I need to spend some time writing them down before they slip away. Some of these ideas are so powerful that they hit me like a bolt of lightning. It’s my job to capture that lighting and put it in a bottle to share it with you. I want to capture that feeling that Archimedes had when he had an insight sitting in the bathtub screamed “Eureka!” and ran naked down the street. I know that I’ll rarely if ever make it there, but that won’t keep me from trying!

My Virtual Library

I wanted a place to put all the stuff I think is awesome. Growing up, I always wanted to have a great library in my house. I remembered the excitement when I learned that I could buy the entire collection of The New Yorker in bound volumes and put them in my house. I’d imagined that I would collect great encyclopedias from the past to peruse whenever I pleased. They would live in mahogany bookcases that looked like they’d belonged to JP Morgan. Then I realized that a New York City apartment doesn’t have the space for a physical library. So I did the next best thing. I’ve created a virtual library that includes lots of the things I enjoy, like my favorite books, words, and humor. You can check it out on the menu at the top of the page.

Blog Highlights

My Time at Amazon

Product and Design

Technical Articles for My Mother-in-Law

Human Behavior

Things I’ve Built

My Adventures and Explorations

  • Taking the Red Pill of Art. Here’s my love letter to art. It’s a story about the red pill and the blue pill, opening your eyes, and what art means to me.
  • The Joy of the Hunt. While I haven’t been outside on any new adventures in the last few months, I wrote about some of my favorite adventures, from finding a hidden castle on top of a library to discovering an old historical text from one of Yale’s secret societies.
  • What a Wonderful Word. A story of untranslatable words from around the world.
  • Carpe Diem! How to Live Like an Emperor. I realized that no matter where I am or where I go, I can live like an Emperor by seizing every moment.
  • Capture Better Memories Without a Camera. How technology is preventing me from building great memories and some techniques I’ve come up with some ways to use my brain to capture special moments instead of my phone.

Life Lessons

Math and Logic


What We Really Need

Human beings want more of everything. We are on a hedonic treadmill that says, “What I have now is OK, but I really want more—more stuff, more money, and more friends. That would make me happy.” From a societal perspective, the hedonic treadmill has some benefits. It keeps us on our toes and moves society forward. It also gives lots of people jobs. If people didn’t want more Oreos, no one would have jobs selling Oreos at the grocery store, or stocking the Oreos on the shelf, or making new kinds of Oreos.


Taking the Red Pill of Art

I don’t know exactly when I took the red pill.(1)Red pill and blue pill: I’m referring to the red pill in the movie The Matrix. Neo takes the red pill to see the world for what it really is. He had a choice to take the red pill or the blue pill, which would have left him in blissful ignorance. It’s much easier to talk about a time when I’d taken the red pill and was talking to someone who hadn’t. I was at the Whitney Museum of Art with my friend. We saw the exhibit fruits, vegetables; fruit and vegetable salad.


1 Red pill and blue pill: I’m referring to the red pill in the movie The Matrix. Neo takes the red pill to see the world for what it really is. He had a choice to take the red pill or the blue pill, which would have left him in blissful ignorance.

My Ideal Retirement Plan

I know that money wouldn’t make me happy, but I still had dreams of being an early retiree. I dreamt of being that person who quit their job, moved to Hawaii, and sipped margaritas while I cashed my dividend checks. But as I got older, I realized that it’s not about the age of retirement but the quality of that retirement.


Guest Post: Blake Schlaff on Fortnite Friendships

Guest Post: My 10-year-old son Blake is an avid Fortnite player who often plays with his friends. I thought it would be good for him (with my help) to tell everyone about the world of social gaming. 

Fortnite is not just a game about fighting. Yes, there is a lot of shooting, collecting guns, and exploring the world. The most exciting part isn’t about fighting it’s about spending time with friends online. Even though my parents only let me play Fortnite with people that I know, playing Fortnite with them is different, and in some ways better, than playing with them in the real world. Playing Fortnite is a lot like being in a virtual world together with my friends, like the Oasis in Ready Player One.


Carpe Diem! How to Live Like an Emperor

I also presented this as the speech as How to Live Like an Emperor in the Age of Coronavirus

At the end of last year, Bubbie, my last living grandparent, was fading away. She couldn’t see, could barely walk, and her kidneys were failing. It was becoming clear that we needed to savor each moment with her. So we created some great memories — like the last time we had a steak dinner with her and needed to push her on her walker around the corner to the restaurant. Or the last time she came to our house and Ari asked if he could snuggle her because he really likes snuggling people. We spent those last months finding special moments with Bubbie. And it was exciting because Bubbie was always up for some good fun.

Life Lessons

Fiction is the Lie That Tells the Truth

When my Bubbie died in January, I wasn’t sure how to deal with it. People kept telling me that, “She lived a good long life” and “Her memory will live forever” but this wasn’t helpful. I know that she lived a great life and I know that I was very lucky to be 41 when my last grandparent died. But how should I deal with her death? What do I do now?

Ideas Life Lessons

How to be Happy — Yale’s Most Popular Class

This year Professor Laurie Santos created Yale’s most popular class of all time. The class is titled Psychology and the Good Life but it’s really a course on how to be happy both in the short and long term. I was excited to hear that Yale was offering the course but even more excited to see that the class is available online. She expanded on the class with her Happiness Lab Podcast. While there’s little I hadn’t heard before, it did a great job of focusing me on what’s important and helped me get into the practice of being happier.


2022 Review


I wanted to give you all a meaningful holiday gift. This is difficult during normal times, and even more difficult during the pandemic.

I’ve always admired people who can give holiday gifts that are truly unique. I’m inspired by some of the great holiday gifts of the past,  like those Thomas Heatherwick’s Christmas Cards or Improv Everywhere’s Holiday Videos. There’s also Aaron Sorkin’s Sports Night holiday gift where he included the names of the backstage cast on the show.

But alas, I’m not a designer or a YouTube creator. I’m a writer but I’m not Aaron Sorkin. So this is my holiday gift to you.


We choose to go to the Moon in this decade and do the other things, not because they are easy, but because they are hard; because that goal will serve to organize and measure the best of our energies and skills, because that challenge is one that we are willing to accept, one we are unwilling to postpone, and one we intend to win, and the others, too.

John F. Kennedy Moon Speech – Rice Stadium”. NASA. September 12, 1962.

Before the pandemic, if I told you that you didn’t have to travel to work and could avoid all of the annoying parties you didn’t want to go to, you might have thought you were getting a good deal.

However, if I’ve learned anything over the past couple of years it’s that there’s a real value in doing things that are hard. Getting dressed up and going to the office puts me in a better headspace to work. Making a trip across the country for a wedding or bar mitzvah means that I’m investing in that experience and therefore getting a better payoff. In short, I get out what I put in.

This year, there’s a wonderful discomfort in New York during the holidays. The streets are clogged and you can’t get into the popular restaurants without reserving a month in advance. But while these things are annoying, it reminds me that the city is coming back to life. And that if I want to live in the greatest city in the world, I need to accept that many other people want to come here as well.


There’s something transcendent about a person who gets to live forever by writing the final chapter of their life. Randy Pausch did this in The Last Lecture, one of the best lectures ever given, where he gave a 90-minute lecture summarizing his life right before he died. 

Jonathan Larson managed to do this with Tick, Tick, Boom, collaborating on his autobiography even though he died in 1996. Tick, Tick, Boom is about Larson’s battle against time. As he was turning 30, he was worried that the professional writer in him was going to die—that, in his words, he was going to “stop being a writer who waits tables and become a waiter with a hobby.” But then the real-life story of Jonathan Larson took a tragic turn. A few years later, his musical Rent would become a huge success, but Larson wouldn’t see that success. He died of an aortic aneurism the day before previews started. Rent inspired an entire generation of creators on Broadway who were never able to collaborate with him. Lin Manuel Miranda, the creator of Hamilton, and one of Larson’s biggest fans made his directorial debut with the movie version of Tick Tick Boom saying, “If they only let me make one movie, I’m glad it was this one.”

And don’t feel you can only love only big “important” things. Take a look at this serious review of a timeless children’s book, How a Book About Grover Revealed to Me the Wide World of Literature. Also, it’s hard to appreciate how good a truly great meal is unless you’ve never had one before. Here’s one of the best food reviews ever: I’m common as muck and spent £150 in a Michelin-star restaurant to see if it was worth it.

And I’ve also got some of my favorite inspirations from previous years here.


For many years I’ve been looking for technologies and techniques to better manage my life and escape from the many digital distractions I face each day. My favorite techniques used to be Getting Things Done and The 7 Habits of Highly Effective People. In my New Years’ Email from 2017, I wrote about some ways people can use technology to disconnect. 

While there are many cool new tools to make life simpler, technology can only take us so far. I think Dave Pell had it right when he said relying on technology to solve your technology problems is like using heroin to kick your methadone habit. I could buy a bucolic vacation home, a fancy VR headset, or an expensive “soundscape” machine. But I’ve found that simple analog tools work great. A cheap pair of earplugs and an eyemask can do wonders when I’m looking for a quiet nap on a Saturday afternoon.

My favorite analog tool is the Bullet Journal. I’ve been using the Bullet Journal for the last year. It’s a simple way to transform my notebook into a journal, a task manager, and a self-improvement tool. While you can use any notebook, I use the Bullet Journal notebook and the companion app. Here are some of the things I like best about The Bullet Journal:

  • Decluttering My Mind. Like Getting Things Done, it takes things out of my head and puts them on paper. Putting these things all out on a piece of paper makes it easier for me to see what’s on my mind and understand what I need to do. Sitting down and having a ritual to stop, think, and plan at regular points helps me clear out my mind and separate planning from doing. It lets me see what’s most important, where I can focus my time, and where I can improve. 
  • The Beauty of Analog. Digital planning tools are helpful but they can be too helpful. They let me have an infinitely long list of things to do but that’s often overwhelming. Putting my Bullet Journal items on paper means that each day, month, week, and year is its own thing. As part of the Bullet Journal process, I review and prioritize things at a regular cadence. Because I need to rewrite things that I want to move forward, things naturally fall off the list.
  • Open Source. Getting started with a Bullet Journal just takes a fresh notebook. I got started with some quick YouTube videos and learned a lot more from the book/audiobook. Then I modified it to suit my day, using it to log my day, set goals, take notes, track improvements, and whatever else I need.


Great humor is about taking a look at the world and saying “Why are things this way? and “What can we do to make them better?” It’s about doing it in a clever and thoughtful rebellious way rather than a full-on attack. Even when kings wielded absolute power, they had the licensed fool or court jester to provide them with the truth in a humorous way. There are some wonderful ways that humor has been used to show the differences in American life like Dave Chapelle’s Chip and Dave and Chris Rock’s Who Wants to Change Places? 

I never thought someone could take over a country through humor, but that’s what Volodymr Zelinsky, the President of Ukraine did. Before becoming President, Zelensky starred in the television show Servant of the People where he played a schoolteacher who became the unlikely president of Ukraine. It’s in Russian with English subtitles on Netflix but you can watch this clip dubbed in English. In the New Yorker, Zelensky says, “I started out making fun of politicians, parodying them, and, in doing so, showing what kind of Ukraine I would like to see.”

Zelensky knows that politicians are really just actors playing for the cameras but he wonders why they aren’t better actors. He says, “I look at things like a producer. I would often watch a scene on the monitor, and the director and I would yell, ‘Stop, no more, this is unwatchable! No one will believe this.'”If politicians are actors, why don’t they create an inspiring epic? That’s what he has done.

Zelensky is currently playing the role of valiant president of Ukraine, inspiring his people to fight in the most important war of our time. The Russians planned for him to leave the country soon after the initial invasion. He surprised them, and the rest of the world, by staying in Kyiv, in green camouflage and leading the resistance. This is our hero comedian. Plus, he’s Jewish. For a more serious take on Zelensky, check out: An Unlikely Hero (Nytimes), Volodymyr Zelenskyy, explained in 8 moments (especially his speech to the European Parliament where the translator is holding back tears).

And now, on the lighter side, some very funny things this year:


Here’s my favorite prompt from ChatGPT (Slightly edited but based on this).

Prompt: Write a letter to my daughter, Sally, from Santa Claus telling her that he isn’t real and that we make up these stories out of love.

Dear Sally,

I hope this letter finds you well. I know you are excited about Christmas and I am too! But I have a secret to tell you. I know that you have always believed in me, Santa Claus, and the magic of Christmas. Today I have to tell you that I am not real, but a character that your parents have told you stories about out of love. 

As you grow older and become more curious about the world around you, you may start to question the existence of Santa Claus and other magical beings. So it’s important to me that you know that I’m not a real person who lives at the North Pole and delivers presents to good boys and girls on Christmas Eve.

Your parents have told you the stories about me and my elves to bring joy and magic into your childhood. They wanted to believe in the spirit and magic of the holiday season.

I want you to know that the love that your parents have for you is real. They have created special memories and traditions to make your childhood special. But the real magic of Christmas is not in the gifts or the stories, it is in the love and warmth that we share with each other. The love that your family has for you is real and true, and that is what truly makes the holiday season special.

As you continue to grow and learn, remember to always believe in the magic of love and kindness. And always remember that even though I’m not a real person, the spirit of Santa Claus lives on in the hearts of those that believe in the holiday season.

Merry Christmas.

Santa Claus



How to Succeed in Business

When we think about being successful at work, we all know that it takes a lot of hard work. But even with that work, success is elusive. That’s because we don’t have a good sense of what it means to be truly great at a job, even for seemingly obvious jobs, like being a doctor. I provide a simple framework on how you can be the best at any job.

“What would you do if I punched you in the face right now?”

That’s the question that Mark Craney, former Operating Partner at Andreessen Horowitz, says is the best sales interview question he’s ever received.

Product Management

How New York City is Acting Like a Tech Company

NYC’s new OMNY MetroCard shows how the city is creating products that better meet customer needs, just like tech giants like Amazon do.

While it’s easy to get sucked into discussions on “important” topics like COVID or politics, sometimes it’s fun to focus on the little things in life. These little things can be incredibly frustrating. Other times they can lead to wonderfully delightful surprises.

Before COVID,(1)This is less of an issue these days, now that I use a Citi Bike for work. one of my minor frustrations was deciding whether or not to buy an unlimited ride subway card or a pay-per-ride card. I’d used to take the subway 5 days a week and a little on weekends. An unlimited ride monthly was normally the right choice. It paid for itself plus a got juiced up that I could ride the subway for free to explore the city. The unlimited ride ticket helped me feel more connected to the city. But what if I went on vacation? What if I had work travel? I would feel cheated if the pay-per-ride card was cheaper that month.

I wanted someone or something to just choose the best card for me. I wanted a card that acts like a pay-per-ride card when I needed it and an unlimited one when I needed it. This is what the new OMNY MetroCard is doing. It’s a card that works like a pay-per-ride card on weeks when you don’t use it a lot and then unlimited weekly on the weeks when you do. It’s literally a card that transforms itself. That’s not the way that it’s being marketed though.

An OMNY ad for this new pricing scheme.

Here’s how it works. New York City has a new(ish) pay-by-phone system called OMNY (you’ve got to love the wordplay). Instead of getting a MetroCard, all you have to do is take out your phone and swipe it against the turnstile reader. With an iPhone, you don’t even need to unlock your phone.

Recently, OMNY created a new kind of subway card. It’s being marketed as an improvement over the pay-per-ride card. You ride 12 times starting on a Monday and every ride after that is free. But here’s the kicker. 12 rides is the same cost as paying for a weekly pass(2)A single ride is $2.75 and a weekly is $33.. So with every ride that you’re purchasing with OMNY you’re also getting one-twelfth of a weekly pass that expires at the end of the week.

Amazon offers a product with similar transformational properties through Amazon Prime Video. When looking to buy a season of a TV show, I have the option of buying the whole season or individual episodes, with the whole season costing more in total but less per episode. But with Amazon Prime Video, I can purchase a single episode, and then, later on, I can use that purchase price toward the whole season. So I’m purchasing the episode but also part of the season. Eventually, as I buy more episodes, I get the whole season for free once I reach the price of the season. It’s two products in one!(3)Correction: Previously, I’d made a much stronger claim which turns out to be false. I thought that each time you rent the movie you get credit towards buying the movie. The credit you get toward purchasing the movie is the amount you pay for the rental. So when you rent the movie, you aren’t just renting it, but also buying a piece of it too. If this were true, there’s no reason to buy a video anymore.

This is a fundamental shift in the way products are sold. Previously, companies would treat their customers as adversaries. For example, a company might sell a gift card with a provision that said something like, “If you don’t use this gift card in a year, we will start charging you a $2/month maintenance fee.” You’d pull out an unused gift card from a drawer only to find that it didn’t have money on it—with the company pocketing all the value. But a few customer-centric companies bucked this trend. I remember when I saw that Starbucks didn’t have an expiration on its gift cards. It made me feel very warm and fuzzy about the company and greatly encouraged me to buy a gift card. Over time, this loyalty toward customers drove Starbucks to one of the largest gift card businesses in the country.(4)In 2021, Starbucks accounted for 10% of all holiday gift card sales—$3B out of a total $28B

So why are we seeing this change to more consumer-friendly products? First, companies are playing catch up with tech giants like Amazon and Google. Tech companies are putting the customer first instead of profits and everyone else is playing catch-up. To paraphrase Ukranian President Volodymyr Zelensky from his television show Servant of the People,(5)In addition to being the name of his television show, Servant of the People is also the name of Zelinsky’s political party “We are here to serve the people. The people are not here to serve us.”

Technology has also allowed companies to create innovative and fungible products because they are no longer physical objects. In the old days, you had a subway token which was a physical metal object. A weekly or monthly ticket was a paper ticket. It’s very hard to transform a token into a paper ticket. But when both of these are on a phone, it becomes possible.

Getting back to the new OMNY card, it’s a great start but there are a few improvements that I would make:

Let me use tax-free money with OMNY. I get to buy my MetroCard with tax-free money using the TransitChek program but this doesn’t currently work with OMNY.

Make OMNY work as a monthly card rather than a weekly. Monthly cards are far more commonly used by locals. Weekly cards are only used by tourists. So make the OMNY card work for people that live here.

Change it from a “pay-per-use that turns into an unlimited when you use it a lot” to “an unlimited card that turns into a pay-per-use card (and gives you a discount) when you don’t use it.” This one is a little complicated. As we said, this card is a mix of a pay-per-ride card and an unlimited card. The current card starts with the pay-per-ride card and then transforms into an unlimited card for the week once you take more than 12 rides. I think it should be a monthly card that you pay for up front. At the beginning of the calendar month, you’d buy this new card at the price of a monthly. If the number of single rides in that month would be less than a monthly, you’d receive a discount for the difference. You’d only pay for the number of single rides you made. Below are some examples of how it would work (keep in mind that a single ride is $2.75 and a monthly card is $127 or about 46 rides):

Scenario 1 (Works as an unlimited card)

In January I take the subway 2 times a day every day including weekends. That’s $170.50 (31 days x 2 rides x $2.75) rides. But a monthly pass only costs $127 so I’d only pay $127 that month.

Result: 62 rides for $127 (the price of a monthly)

Scenario 2 (Works as a pay-per-use card)

In February, I went on vacation for a week. Also, I didn’t take any rides on the weekend. So 15 days at 2 rides a day is $82.50. I’d paid $127 in the beginning of the month so I’d get $44.50 back. I think this should be sold as a monthly subscription product so this value would be credited to my payment for next month’s card.

Result: 30 rides for $82.50 (the price of a pay-per-ride card)

Starting with a monthly card has a number of advantages:

  1. Customers only pay once a month so they don’t feel the pain of paying each time. This would encourage them to ride more.
  2. Customers always get some sort of a gift at the end of the month. If they don’t ride enough, they get a discount at the end of the month. If they ride more than the cost of a weekly, they see how much they saved by not paying for each additional ride. Both of these “gifts” build loyalty.
  3. It automatically gives people the best option between a monthly and a pay-per-use. Because they’re only paying for what you use, more customers would sign up for this card and not have to worry about how they were being charged.
  4. Customers feel like they already have a monthly so they will ride the subway as if they had a monthly because they would think of every ride as “free.”
  5. It sends the message, “We care about you as a New Yorker. Use the subway as you want to use it and we will give you the best price.” The subway becomes utility that you don’t need to think about.

Even though the current product still has areas for improvement, it’s a good start. The city is aligning the product with customer needs rather than just thinking about making a profit. It’s acting like a tech company! Tech companies understand that customers will always have a desire for improvement and that it’s the company’s job to meet that need. Amazon’s Jeff Bezos sums it up when he says, “Customers are always beautifully, wonderfully dissatisfied, even when they report being happy and business is great.”


1 This is less of an issue these days, now that I use a Citi Bike for work.
2 A single ride is $2.75 and a weekly is $33.
3 Correction: Previously, I’d made a much stronger claim which turns out to be false. I thought that each time you rent the movie you get credit towards buying the movie. The credit you get toward purchasing the movie is the amount you pay for the rental. So when you rent the movie, you aren’t just renting it, but also buying a piece of it too. If this were true, there’s no reason to buy a video anymore.
4 In 2021, Starbucks accounted for 10% of all holiday gift card sales—$3B out of a total $28B
5 In addition to being the name of his television show, Servant of the People is also the name of Zelinsky’s political party

When Experiences Are Better than Buying Things

The first time I experienced “Insane Mode” in a Tesla was in Knoxville Tennessee. We were outside cousin Greg’s house next to a beautiful lake. Blake was in the back seat while we rolled to an empty straight-away in front of his house. Then Greg said, “Do you want to see something cool? Make sure your seatbelts are buckled.” He brought the car to a stop and pressed a few buttons. “Ready?” he said. Then he stepped on the accelerator and sent us from zero to sixty in less than three seconds. We were immediately pinned back in our seats as the sides of our eyes and mouth reached for the backrest. After we got out, I thought, “I would love to buy this car.”(1)Here are some NSFW reactions of people with their first time with Insane mode.

But even if I bought the car, I wouldn’t be able to replicate that experience. The first time trying Insane Mode (or its newer cousins Ludacris Mode and Plaid Mode) can’t be duplicated. Companies try to convince you that you can do it—just purchase their products! This happens with kids’ toys all the time. A few years ago, I bought the Little Bits R2-D2. This is a nifty little kit for kids where kids build a remote-controlled R2-D2 that we built with some friends. We enjoyed building it that first time, but the box said, “Create. Play. Invent.” But after we followed the instructions and played with it, we never did create or invent, and R2-D2 went to hibernate in the closet.(2)It occurred to me that it would be better to rent toys like this rather than to buy them.

Each time you use something, you get a new experience. The first experience is the most powerful, then each additional experience is less so. Eventually, you just take it for granted and don’t appreciate it anymore. This is why behavioral economists(3)Behavioral economists study the psychological side of economics. say that experiences are more valuable than things. When you purchase that experience, you are spending all of your money on that first experience. The joy from these later experiences are a lot less valuable.(4)In his play Rosencrantz and Guildenstern are Dead, Tom Stoppard tells a story about how a truly novel experience can become commonplace. Most interesting is that transition, at the second experience.

GUILDENSTERN: A man breaking his journey between one place and another at a third place of no name, character, population or significance, sees a unicorn cross his path and disappear. That in itself is startling, but there are precedents for mystical encounters of various kinds, or to be less extreme, a choice of persuasions to put it down to fancy; until – “My God,” says the second man, “I must be dreaming, I thought I saw a unicorn.” At which point, a dimension is added that makes the experience as alarming as it will ever be. A third witness, you understand, adds no further dimension but only spreads it thinner, and a fourth thinner still, and the more witnesses there are, the thinner it gets and the more reasonable it becomes until it is as thin as reality, the name we give to the common experience… “Look, look” recites the crowd. “A horse with an arrow in its forehead! It must have been mistaken for a deer.”

People become accustomed to almost everything, even something as wonderful as living in paradise. The Nobel Prize winner Daniel Kahnemann was offered a position at a California University after having spent years in Michigan. He thought that clearly, people were happier in California with all the great weather and good vibes. If he would be happier in California, that might tip the scales on whether to take the position. So he did a large study to figure out the difference between people’s happiness in Michigan and California. He learned that when people move to California they see an immediate uptick in their happiness. But over time, that fades and the people settle into the same level of happiness they had before the move. Kahnemann pointed out that it’s very hard to get answers to questions on happiness. When you ask people, “How happy does living in California make you?” you invariably get the answer to the question “How happy does living in California make you when you are thinking about the fact that you live in California?” This is an important distinction because rarely are people thinking about the weather and good vibes of California on an everyday basis.

When I was at Amazon, I wanted to see how experiences fade over time. The company had these beautifully designed badges you’d use to get into buildings. The designers spent a huge amount of time and money to get them perfectly right. They had this silky matte sheen that reflected the light perfectly. When I got the badge, it was immediately placed in a plastic sheath, providing it with a more gauche glossy protection.

Unable to decide whether to leave it exposed and attractive or protected and shiny, I decided to do an experiment. By default, I’d leave it in the plastic sheath for the night. When I got to work, I took it out of its plastic covering so I could appreciate it. At night I’d put it back. So each morning I’d have to take the action to unprotect the badge and make it prettier. For the first few months, I took it out and really admired the craftsmanship of the badge. After three months I realized that I didn’t care about the design anymore and left it in the protective case. The experience of appreciating the badge had worn off.

Experiences are also great because they create powerful shared moments.(5)The group Improv Everywhere creates amazing experiences between people. One of my favorite experiences in college didn’t cost any money—well, not any additional money. $2 bills have always been pretty rare. Back when people used to pay for everything with cash, I’d get one every few years. My grandfather Barney Liebman used to save all of his $2 bills in his desk drawer. But something strange happened in Harvard Square in 1995. I was at the Au Bon Pain, standing behind a young African American grad student waiting to pay. He bought a pastry and a coffee. He paid for his $8 purchase with one $5 bill and two $2 bills. Two $2 bills! One would have been unusual. Maybe he didn’t care about his $2 bill. But two?! How could this be?! I had to find out. After a thorough investigation, I learned that you can ask for $2 bills at the bank, just like any other money. So I got a bunch and started buying things with them. It would always put a smile on the cashier’s face, and it was free!(6)The one problem was that banks would only have a few $2 bills at any time. If you’re really serious about two-dollar bills, you can have your bank order you a stack from the Federal Reserve. It’s less relevant these days as no one pays with cash anymore.

Even though I know that experiences are more important than physical items, it still seems like physical items have more weight (no pun intended). There’s still the temptation to buy something “real” even when it’s less useful. Before the pandemic, Blake asked for virtual Fortnite presents for his birthday. These were outfits for his virtual characters.

Abigail said, “That’s such a waste. It’s just something that will live on his computer. He’ll use it once or twice and then forget about it.”

I replied, “Yes. It’s awesome. He gets a gift he really wants for his birthday and has a wonderful experience. And when he gets sick of it, we never have to throw it out!”

Note: For people that want a good compromise between renting and purchasing movies, Amazon’s Prime Video has an interesting solution. Each time you rent a movie, you are credited for the purchase of that movie. You can rent the movie as many times as you want but you are capped at the total cost of buying the movie.

Note: There’s a lot more about this in Chapter 5 of Jonathan Haidt’s The Happiness Hypothesis.


1 Here are some NSFW reactions of people with their first time with Insane mode.
2 It occurred to me that it would be better to rent toys like this rather than to buy them.
3 Behavioral economists study the psychological side of economics.
4 In his play Rosencrantz and Guildenstern are Dead, Tom Stoppard tells a story about how a truly novel experience can become commonplace. Most interesting is that transition, at the second experience.

GUILDENSTERN: A man breaking his journey between one place and another at a third place of no name, character, population or significance, sees a unicorn cross his path and disappear. That in itself is startling, but there are precedents for mystical encounters of various kinds, or to be less extreme, a choice of persuasions to put it down to fancy; until – “My God,” says the second man, “I must be dreaming, I thought I saw a unicorn.” At which point, a dimension is added that makes the experience as alarming as it will ever be. A third witness, you understand, adds no further dimension but only spreads it thinner, and a fourth thinner still, and the more witnesses there are, the thinner it gets and the more reasonable it becomes until it is as thin as reality, the name we give to the common experience… “Look, look” recites the crowd. “A horse with an arrow in its forehead! It must have been mistaken for a deer.”

5 The group Improv Everywhere creates amazing experiences between people.
6 The one problem was that banks would only have a few $2 bills at any time. If you’re really serious about two-dollar bills, you can have your bank order you a stack from the Federal Reserve. It’s less relevant these days as no one pays with cash anymore.

Happy 2022!

I wanted to give you all a meaningful holiday gift. This is difficult during normal times, and even more difficult during the pandemic.

I’ve always admired people who can give holiday gifts that are truly unique. Designers do it best. Last year, I wrote about Thomas Heatherwick’s Christmas gifts. From 1994 to 2010, Heatherwick, creator of New York’s Vessel, created original, unique, and surprising Christmas cards. There was even a museum exhibit of these cards.

This year I wanted to start with a holiday gift from Improv Everywhere. During this time of year, they surprise people with wonderful holiday experiences like Giant Boombox, The Light Switch, and Light Up Someone’s Holiday. Since 2001, Improv Everywhere has been turning New York City into a communal space for positive pranks. You can find a quick summary of Improv Everywhere from CBS This Morning.

But alas, I’m not a designer or a YouTube creator. I’m a writer. So this is my holiday gift to you.


In 2020, I did a whole lot of writing. This year I have a more demanding job which has limited my quantity of blog posts. Also, my big writing project is my book which I’ve excerpted at the end of this email.

If you’d like to poke around through my thoughts, visit for blog posts or check out my library for other random thoughts. Here are some of my favorite recent writing:

  • Why We Love Camp Ramah. My essay on Camp Ramah, the Jewish Summer Camp we send the kids to each year. It’s about how we are trying to raise our kids with positive values and how we can use religion to help guide our family in that direction.
  • Zaid’s Unopened Hannukah Present. I letter to my grandfather and about how I’ll always remember him, even if I couldn’t do everything that I wanted with him.
  • Amelia Earharts’ 77-Year-Long Journey Around the World (video). My story about 2 Amelia Earharts—the one who started the journey around the world and the one who finished it.


This has been a hard year. It was different from last year. In a word, 2020 sucked. Plain and simple.




When 2020 was over, we expected things to get back to normal. Instead, 2021 was a year of waiting, partially frozen in time. It felt like we were in a chrysalis, that cocoon between being a caterpillar and being a butterfly. The chrysalis is a complete breakdown of the caterpillar into its foundational amino acids and reconstituting itself as a butterfly. That’s what this year was like—a complete breakdown of everything before and waiting to see what will happen when we emerge. While inside the cocoon I learned to appreciate the little things in life, like taking daily pictures for my virtual background while I worked from home.

In this section, I like to highlight the goodness of the world. This year I’ll start with Dave Pell’s piece I read more news than anyone. Trust me, people are better than we’re led to think. Dave writes the newsletter NextDraft, my favorite source of daily news.

I’ve also got a lot of happiness and inspiration links on my website. I’ve also written some pieces you might find inspiring in these difficult times. Here are some of my favorites:

  • Thank You for Being a Friend. Friendship is about being there for other people. Anyone can celebrate with you when it’s convenient. A true friend stands by you when it’s inconvenient.
  • The Best Vacation Ever. Thank God We Survived. This year reminds me of a vacation we took a few years ago. Everything was planned impeccably only to completely fall apart. It was an awesome trip in spite of (or maybe because of) all of these challenges.

And I’ve also got some of my favorite inspirations here.


My kids live in the future. Two years ago, Blake taught me about Fortnight and the Metaverse, well before Mark Zuckerberg renamed his company. This year I learned how YouTube is taking over the media landscape. If you don’t have tweenage boys, you may not know that being a YouTuber is the #1 dream profession, significantly ahead of old favorites like movie star or rock idol. Here’s a quick summary:


During COVID-19, everyone seemed to be having the same experiences at the same time. So our family had the same experiences as many people on YouTube. Our favorite online family is the Holderness Family. Here are our favorite videos that take us through 2021:


In the early part of the year, I found some fantastic podcasts about COVID-19.

  • This American Life Episode 727 had an interview with 4 of the scientists that did the basic research on the COVID-19 vaccine. All the research on the vaccine was done years ago, on MERS. Without that huge jump start, we would still be waiting for a vaccine.
  • The Great Vaccinator is about the most important scientist you’ve never heard of. Maurice Hilleman created the Mumps vaccine in 4 years and 8 of the 14 standard childhood vaccines.
  • Every Day is Ignaz Semmelweis Day is an homage to the discoverer of germs and the first proponent of hand washing. The medical community was not a fan of Semmelweis, annoyed by his guidance on hygiene. But why were they so against hand washing but so in favor of anesthesia which was discovered at the same time? Atul Gawande explains that you can see anesthesia working right away but don’t physically see the results of hygiene.
  • The Thing I’m Getting Over is a This American Life did a podcast on how recovering feels. spoiler alert: it’s not a fun process.


  • How to Transform Your Notebook. I’ve been looking at productivity tools for years. Recently I picked up The Bullet Journal. This is a ridiculously simple way of managing your notes and to-do list all in one place. I’m really enjoying the custom notebook and the companion app.
  • Under the Covers of Excel. Did you ever wonder how Excel works? Enter Joel Spolsky, the founder of Trello and Stack Overflow, who worked on Excel in the 1990s. I learned a lot from his entertaining talk, You Suck at Excel. My favorite part was how R1C1 notation explains how Excel’s “magic” of dragging cells works.
  • Fun with Alexa. Here are two lists of Alexa Easter Eggs. My favorites are “Alexa, open the pod bay doors,” “What’s the answer to life, the universe, and everything?” and “Up up down down left right left right B A start.”
  • “Fresh” Krispy Kreme Donuts at Home. There’s nothing better than a fresh-from-the-oven Krispy Kreme donut. They just don’t taste the same they’re not fresh. But I’ve learned that popping a cold one in the oven for 10 seconds brings back all that fresh-baked goodness.



Thanks for sticking with me for long! For you intrepid readers, I have a special treat for you. This is the beginning of my leadership book based on Amazon’s culture, called Thinking Amazonian (Day 1). It’s what I learned from the company, and how other people can use Amazon’s best practices in their own lives. It’s in the early stages and I’m still looking for an editor to clean it up and an agent to help me sell it. If you have any thoughts, please email me. Here’s the beginning:


I had the privilege of working for one of the world’s biggest celebrities and now I’m writing a book about it. OK, that’s not exactly true but it’s close. I worked at Amazon as their head of cloud banking and I’m writing a book about how Amazon gave me a new framework for thinking about the world.

I was the Head of Banking for Amazon Web Services (AWS), responsible for AWS’s strategic initiatives for banks and lenders across the world. I worked with these organizations to transform their existing businesses and bring new, innovative solutions to market with AWS.

There are lots of great books and videos about Amazon, but this one is about being Amazonian. That’s what Amazon employees call themselves. It’s more than a book about Amazon. It’s about how to take the core of Amazon’s culture (called Leadership Principles) and apply them to your work and your life. While they often look like boring management principles, they offer insights into Amazon’s success. They also offer an avenue for deeper personal growth. For example, one of Amazon’s Leadership Principles is “Dive Deep.” The principle exemplifies Amazon’s focus on operational excellence, but it also highlights how you can appreciate the beauty of the everyday world.

Understanding Amazonian thinking is key to being successful with technology. I’ve seen companies try to be like Amazon and fail. They spend millions of dollars on an innovation center and gloat about how they’ve implemented design thinking. When companies try to be more like Silicon Valley, they wear hoodies and jeans to work without knowing why. They think that the casual dress code of Silicon Valley started with the hippie counterculture of Steve Jobs. But it has a much deeper and important meaning. Silicon Valley’s casual dress code started with the godfather of Silicon Valley, Robert Noyce.

Robert Noyce was born in Burlington Iowa into a deep Midwestern Congregationalist ethic. When he started Intel, the first modern tech company, he brought his Midwestern roots to the company. He believed that no one was better than anyone else. He had a casual dress code because he believed that the best ideas should win, not the ideas from the people with the best suits and the biggest offices. As other tech companies emerged in Silicon Valley, they imported their culture from Intel. Most companies don’t know this history and adopt the dress code without adopting this focus on the meritocracy of ideas, missing the point and most of the value.

Most books about Amazon and other tech companies treat the reader as a tourist visiting a new and mystical land. It’s kind of like watching the movie Charlie and the Chocolate Factory. The UK paper, The Register, even refers to Google as “The Chocolate Factory” because it’s as weird and wonderous as Willy Wonka’s candy factory. There are wonderful and amazing things about Amazon that I’ll share in the book, I want you to get more than that. What if you could get the mind of Agustus Gloop, the glutton who fell into Mr. Wonka’s chocolate river, and find out how the experience changed him. That’s the feeling I want to give you in this book. I want to take you inside Jeff’s peculiar company.

Throughout the book, I refer to Jeff Bezos as Jeff, not because I know him personally but because all Amazonians call him that. At each all-hands meeting, Jeff highlights a few of his favorite things posted on Amazon’s internal website. Once he pulled up a humorous quote from another Amazonian named Jeff that said something like:

I am the founder of the Amazon support group “Jeffs who are not Jeff.” We come together to support the “other Jeffs” at Amazon. We meet every Thursday at 8 PM between the groups “Fire Phone Owners Anonymous” and “Amazonians named Alexa.”

So what does it mean to be Amazonian? From the outside, Amazon looks like a holding company—a collection of businesses from a bookseller to a grocery store to a television production company. There’s even my part of the business, Amazon Web Services, the world’s largest cloud provider. But all of these pieces are held together by one thing—Amazon’s culture.

Amazon’s culture is centered around 16 Leadership Principles. These Leadership Principles are the core of Amazon’s interviews, promotions, and making everyday decisions. In this book, I’m going to take you through the 16 principles and show you how I’ve applied them and how you can use them in your personal and business life.

Let’s start with the first principle: Customer Obsession. This means providing the best possible experience for each customer. When Amazon was just selling books, it meant providing the best book-buying experience in the world, but things have gotten more complicated over time.

Customer Obsession applies to the whole firm, even unlikely areas like recruiting. Most companies treat their interviewees as vendors selling their services. They want to hire the best people and ignore those that they don’t need. But Amazon knows that virtually everyone that interviews is a customer, so it strives to give each interviewee a great experience. It doesn’t want to lose that retail customer and their friends because of a bad interview experience.

What does Customer Obsession mean for this book? Well, you, as my reader, are my customer. I want to give you an amazing experience reading this book. Having an exceptional experience is about looking beyond the ordinary and creating something new. Here’s an example of an exceptional experience.

In June of  2019, I went on my first visit to Japan when I spoke at the AWS Summit in Tokyo. This is a massive conference where over 10,000 Japanese coders streamed into the Makuhari Messe Conference Center in suburban Tokyo. I tried to find my way in the flood of attendees, where everything looked familiar but slightly off. Our Japanese hosts had t-shirts that said, “ASK ME! I’m with the AWS Summit!” but when I needed directions, he responded to me with all the English he knew, saying, “AWS. Yes. Yes. AWS.”

I was excited to experience everything Japanese. Familiar things like cheesecake took on a magical new meaning, both fluffier and sweeter than the American or Italian versions. 7-11 was a place to get high-quality food like beef teriyaki jerky or dried squid. While my hotel room had one tiny bed, the hotel also had five bathhouses. These bathhouses were traditional in Japanese hotels, and I had to try them. The signs said that there were absolutely no visible tattoos or bathing suits allowed. There were various different stations filled with cold water, like one where you were massaged by rollers and another where sitting one tub caused water to cascade into others. It was a novel and exciting theme park for nude cold plunges. At the same time, I was terrified that one of my business colleagues would come in and sit next to me. Luckily the bath was empty the whole time I was there. I was in a world of sensory overload where I constantly wanted more. If the 7-11 was this good, the best thing in Tokyo must be mind-blowing. When I asked my host, he told me the best thing in Tokyo is the Imperial Palace.

The Imperial Palace is the main residence of the Emporer of Japan. After crossing the moat that protected the palace from ancient invaders, I entered a history far older and more powerful than I imagined. I walked through a grassy lawn area where the Emperor housed his concubines and visited the base of the giant Tenshu tower that burned down in 1657. The rulers of Toyko were so powerful that they never felt the need to rebuild it.

But walking through The Palace, something was missing. I felt this when I was walking through the palace’s East Gardens. While the gardens were beautiful, they weren’t that different from the gardens of Central Park a few blocks from my apartment. While it sounds silly and pretentious, I wanted more from these trees and plants.

But how could I have a better experience at the East Gardens? The Emperor had done his part. In 1968, the Emperor opened the gardens to the public because he wanted to share this treasure with the people. People like me could walk around except on Mondays and Fridays when it was closed for the Emporer and the Imperial Family to stroll around.

I wondered what the Emporer did on those days in the garden. I bet I could do these things too. I could sit and meditate next to the Emporer’s iris garden, one of the most beautiful in the world. The irises were transplanted from the iris garden of Meiji Jingu, a shrine dedicated to Emperor Meiji, the great-great-grandfather of the current Emperor.




Approaching the Emperor’s Iris Garden

In the Emperor’s Iris Garden

As I sat there for an hour my perspective totally changed. Instead of demanding more and better experiences from everything, I was able to appreciate the best things in life. I felt a sublime calmness and happiness come over me. Strange and wonderful things started to happen as I let things unfold, like when a couple sat next to me with a Yankees cap. I learned that they were from Chile and were in Japan visiting a friend they met through an organization of international friendship created by Jimmy Carter. The Yankees cap came via one of their friends who lived a mile north of me, halfway around the world in New York.

When I left the garden, I felt like an Emperor. It wasn’t about the quantity of experience but its quality. I was able to take this experience and feeling with me when I went home. In this book, I want to give you that kind of experience, treating you like the special customer that you are.

You can also read more about the book and why it’s called Thinking Amazonian (Day 1) or check out some sample chapters:

Introductory Chapters

From Amazon’s Leadership Principles:


As I sign off from this email, I wanted to leave you with one of my cards. I wrote about the story behind these cards, but the message stands by itself. Thanks for being my friend. You’re Awesome. Let’s Talk.

My Card


P.S. If you’d like to read more of my writing check out If you want to get more articles by email you can subscribe here. If you want to unsubscribe from this annual letter you can do it here.


Everything as a Service

These days, all of these products are being sold as services. With Amazon Web Services we’re buying IT infrastructure and computing as a service. With Apple Music, we’re no longer buying music but streaming it over the internet for a monthly fee. We don’t even store our own pictures anymore, they stored in the cloud rather than on our own computers. With “Subscribe and Save” from Amazon, we can even get toilet paper as a service.


Why We Love Camp Ramah

You walk into the field and see a group of children huddled around a fire pit. They’re having fun, performing strange rituals, singing odd songs, and building a community. What do you call this? Summer camp. If the songs are in Hebrew and the rituals are thousands of years old, then you’d call it Camp Ramah.


Kids Do the Most Incredible Things

Summary: Kids do incredible things. Instead of trying to teach them as little adults, give them some tools and flexibility and see what they create. They may not do what you expect, but it’s fascinating (and funny) to see how they think.


When My Career Caught the Mail Truck

Intro: One of my friends told me that at 33, married with a baby, she’s doing some soul searching. She thought at some point that she’d be set and have figured out her career, but she’s realized that things never settle and it’s all journey. This makes her a little sad and confused. Here’s my response:

Willy Wonka: “Don’t forget what happened to the man who suddenly got everything he wanted.”

Charlie Bucket: “What happened?”

Willy Wonka: “He lived happily ever after.”

Charlie and the Chocolate Factory

I used to think that there was a way to win the game of life. I thought there was a general scheme to the world and if I just worked hard enough, things would work out awesomely. This worked for a while. If I worked hard at school, I would get into a great college. If I worked hard in college I would get a great job. I thought this is the way that life worked too.


The Future of the Hybrid Office

It’s time to go back to the office. Some of us are already there and others, like me, will be back sometime in 2021. A lot has changed since 2019. Now we all know what a fully remote workforce looks like and most of us know how to host a Zoom meeting (though it’s still surprising how many times I need to tell people to mute their phones).

In his annual letter to JP Morgan shareholders, Jamie Dimon says that he learned that “Performing jobs remotely is more successful when people know one another and already have a large body of existing work to do. It does not work as well when people don’t know one another.” I learned these lessons over years of working in hybrid environments. When I was at AIG, my entire team, including my boss and my teammates were all based in Charlotte North Carolina while I was based in New York. We learned that we needed to meet in person a few times a year to build trust and agree on what to do. These conversations were imperative to getting everyone on the same page. These were the times to have disagreements about what to focus on and what could be postponed. We left these meetings with a plan. Then we could all travel to our own locations and get our work done.