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That Time I was Catfished by a Robot Secretary

Catfish: To trick someone into a relationship online using a fictional persona and/or photographs.

I was trying to set up a meeting with one of my friends. He has his own venture-capital firm so he runs a lean shop. Also, as a venture capitalist, he likes to leverage new forms of technology.

I sent an email and said, “Hey, let’s meet up.“

He writes me back, “That sounds great! Clara, can you set something up?” and CCed his secretary Clara.

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Cloud Banking 101: Technology Exists to Support the Business

Summary: In the beginning, computers were expensive and complicated machines and needed a cadre of high priests to cater to their every beck and call. However, as computers have become cheaper and more ubiquitous in business, technology processes need to become business processes. While many businesses know they have to do this, old habits and processes die hard. In order to be successful, technology needs to be fully integrated into the business, like any other function.  

In the early days of enterprise computing, computers were giant, room-sized machines. They spoke an arcane language and ate specially formulated punchcards. They were complicated and finicky, broke frequently and needed an army of technicians to keep them running.

The Monolith from 2001: A Space Odyssey

Computing power was the most scarce resource in the company. A mistake in a punchcard could cause the business to waste thousands of dollars in lost processing time. In order to run these machines at peak efficiency, a cadre of high priests of computing grew up to tend to their every need. Much like ancient gods, these priests’ main goal is to make sure that the machines were kept happy with their daily supply of punchcards.

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When a Book Gets Caught Up in the Story. The Art of the Book in the Digital Age

When I was in college, David Foster Wallace (DFW as he was affectionately referred to) was a literary powerhouse. He was the author that all of the literature fanatics loved to read (or at least said that they loved to read). He wrote books like the thousand-page tour-de-force Infinite Jest that were too long and complicated for science geeks like me. DFW gave exactly one talk about his philosophy on life, addressing the graduating class of Kenyan College in 2005. The talk was titled This is Water.

After he died, that speech became a holy relic to the worshippers of DFW. But how do you take that speech and make it into something more, both as a homage to DFW and a way of preserving and extending the insights of the author? You create a book.

I loved the speech and was curious about how it could be transformed into a book. The speech is only 25 minutes long, so it needed to be something special. When I was in college, there was a room in the library for special books called The Art of the Book. It displayed books for their craft and construction, not just their content. The book This Is Water: Some Thoughts, Delivered on a Significant Occasion, about Living a Compassionate Life reminds me of the books in that room. It is a beautiful little volume with DFW’s speech split up over pages, complementing the cadence to the author’s writing.(1)I enjoy reading the book while listening to the audio at the same time and follow along for a multi-sensory experience.

Footnotes

Footnotes
1 I enjoy reading the book while listening to the audio at the same time and follow along for a multi-sensory experience.
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Capture Better Memories Without a Camera

I’m always looking to better capture the special moments of my kids growing up. While having an iPhone in my pocket at all times lets me document these experiences, I feel like I’m not capturing the essence of those moments. I started thinking that technology was part of the problem, and if technology was causing the problem, more technology won’t fix it.

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When Millions of Eyes at Amazon Were Wrong

Disclaimer: I worked at Amazon Web Services as the Head of Banking Business Development. This writing does not represent the views of Amazon and opinions written here are strictly my own. Also, I’ll admit that this post wouldn’t be very interesting if it wasn’t about Amazon; however, it does highlight some key things about the company: 1) Amazon, like every other company, makes mistakes 2) Unlike many other companies, Amazon doesn’t view itself as infallible 3) When mistakes are discovered, the company quickly fixes them.

Amazon has a very strong culture. At other places I’ve worked, culture is an aspiration at the senior level but took a back seat to more pressing concerns like making as much money as possible. Amazon embeds its culture in its 14 Leadership Principles. This is a common language and framework that forms the basis of everything the company does, from interviews to everyday decisions.

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My Old Welcome Page!

Who is Robert Schlaff?

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.

About This Site

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. Madeleine L’Engle said that every writer needs to keep an honest, unpublishable journal that nobody reads, nobody but you. But some of this stuff is too good to keep to myself. So I’m sharing it with you.

When I’m writing, I picture having a conversation with some of the world’s smartest and most interesting people — you, my readers. I picture us all sitting around a table telling stories and having fun. I’d like to think we’re a digital version of the Algonquin Round Table. Throughout the 1920s, some friends would meet daily for lunch at the Algonquin Hotel in New York. They included the founding editor of the New Yorker Harold Ross, the playwright George S. Kaufmann and the writer Dorothy Parker. This group, called The Algonquin Round Table,  would meet to tell stories and share quips in a bustling city that was finding its place on the world stage. They were the original raconteurs of New York, getting together to share stories that would enlighten and entertain. In an age when we no longer have two-martini lunches, I wanted to humbly bring that sensibility online.

Highlights

Life Lessons

Product and Design

Art and Writing

Technical

Human Behavior

Math and Logic

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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.

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No Pain, No Gain at Amazon

Disclaimer: I work at Amazon but this writing does not represent Amazon in any way. Opinions written here are strictly my own.

Starting at Amazon was hard. It’s not that anyone hazed me—the people were really nice. And it’s not like I was working crazy hours—I’ve worked much longer hours in consulting. It was hard because I was out of shape.

When I started, I was amazed at the people around me. They were able to get so much done! Amazon hires great people but it’s more than that. Amazon teaches people how to continually improve and learn. Starting at Amazon means getting into “learning shape.”

I wasn’t used to this. Most people aren’t. At my previous jobs, the goal was to get my job done, follow the process, and meet my annual targets. At Amazon, I needed to do all of this, but I also needed to continually improve myself. It’s like going to the gym. My boss even told me that working at Amazon is about building up your muscles.

When you go to the gym, it hurts. You’re breaking down your muscles at each workout and they come back stronger. When you’re out of shape, the pain you feel the first days is the worst. At Amazon, it’s not a workout for your body but a workout for your mind.

At Amazon, we’re obsessed at meeting the needs of our customers. We know that our customers will never be satisfied; therefore, everyone needs to continuously improve and learn new things.

“This is a phenomenal thing!” you might say. I want to keep learning. I LOVE learning. But when was the last time you really “did learning.” Maybe in college? But you’ve probably forgotten how hard it is to learn. Learning is about getting B’s and C’s before you get an A. At most companies you’re supposed to get an A on every presentation that you do. But learning is about making mistakes. Learning hurts. In The Last Lecture, Randy Pausch summed it up well, saying, “Experience is what you get when you don’t get what you wanted.” It’s not fun but it’s true.

Professor Carol Dweck has a good model for the way Amazon differs from other companies. She describes two mindsets, the growth mindset (which is similar to Amazon) and the fixed mindset (similar to most companies).

The Growth (Amazon) Mindset

In a growth mindset, people believe that their most basic abilities can be developed through dedication and hard work—brains and talent are just the starting point. You’re always learning, getting better and adapting to the changing world. Failure is something to learn from, not a judgment of your capabilities or worth as a human being.

People with a growth mindset know that life provides you with many opportunities to improve. They know that it’s not worth worrying about the past and hoping they can fix it. Instead, they focus on learning from experiences (and even seeking experiences) where they don’t perform perfectly.

This all sounds great in theory but it’s a bit scary in practice. Take Jeff and MacKenzie Bezos’s approach to raising their kids. They wanted to make sure that their kids can create and learn as much as possible so they give their kids access to the best tools. This means letting their kids use sharp knives at age 4 and certain power tools at 7 or 8. Why? MacKenzie said, “I’d much rather have a kid with 9 fingers than a resourceless kid.”

Fixed (Typical Company) Mindset

People with a fixed Mindset assume that they are born with a fixed set of capabilities (e.g., intelligence, creativity, artistic ability) at birth. Because these qualities are carved in stone, life is a series of tests to see how strong these capabilities really are. People with a fixed mindset think that you can’t work to achieve something you’re not born with. For example, they might think that the only “real” coders are those with computer science degrees. In the story of The Tortoise and the Hare, they would hire the naturally talented hare, not the hardworking tortoise.

People (and companies) with a fixed mindset are afraid to fail. Failure is a mark against you, showing that you are less capable than before. These companies say, “Why will we promote the person who fails? We only want successful people here!”

For those of you that like pictures, there’s a great summary of the two mindsets, but I like this tweeted cartoon the best:

At Amazon, we call the growth mindset “Day 1.” In his 2016 letter to shareholders, Jeff Bezos talked a lot about the Day 1 (growth) mindset at Amazon and what happens when you move away from that and into a Day 2 (fixed) mindset.

Jeff, what does Day 2 look like?

That’s a question I just got at our most recent all-hands meeting. I’ve been reminding people that it’s Day 1 for a couple of decades. I work in an Amazon building named Day 1, and when I moved buildings, I took the name with me. I spend time thinking about this topic.

Day 2 is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day 1.

To be sure, this kind of decline would happen in extreme slow motion. An established company might harvest Day 2 for decades, but the final result would still come.

There’s No Compression Algorithm for Experience

The problem with the growth mindset is that it’s hard. You have to try your hardest and be willing to fail. Andy Jassy, CEO of Amazon Web Services says, “There is no compression algorithm for experience. You can’t learn certain lessons without going through the curve”. Because it’s hard, large companies try to take shortcuts.

In his 2016 letter to shareholders, Jeff talks about how big companies tend to use proxies instead of focusing on what’s really needed—meeting customer needs.

Good process serves you so you can serve customers. But if you’re not watchful, the process can become the thing. This can happen very easily in large organizations. The process becomes the proxy for the result you want. You stop looking at outcomes and just make sure you’re doing the process right. Gulp. It’s not that rare to hear a junior leader defend a bad outcome with something like, “Well, we followed the process.” A more experienced leader will use it as an opportunity to investigate and improve the process. The process is not the thing. It’s always worth asking, do we own the process or does the process own us? In a Day 2 company, you might find it’s the second.

Large companies might use these shortcuts rather than focusing on learning. One example is an innovation lab that spends tens of millions of dollars experimenting with technology so the company can say, “We are a very innovative company.“ However, these innovations rarely make it out of the lab to serve customers.

But the most insidious version of the shortcut cuts to the heart of the growth mindset. It’s the corporate view towards failure. In order to be successful, companies can’t be afraid to fail. Jeff talks about this a lot. However, a lot of companies use failure as a proxy for innovation and actually court it. I had a previous boss who said, “We should be failing a third of the time or we’re not trying hard enough.”

Failing is not an inherently good thing in a company. We should not be looking at failure as something that we want to do. However, we have to be looking at failure as an inherent aspect of growth. Real failure is painful. In order to grow, you need to try your hardest, get knocked down, and get up again. It’s hard but it’s the only way to grow.

How it Might Feel

If you don’t take the right perspective, it feels like you’re failing and you might even feel like a failure. At a regular job, if you get 90% of your job done you’re doing great. If you get 110% of your job done you’re amazing. But at Amazon, you have the ability to do 300% of what you’ve normally done. If you can get 70% of that done, you’re still at 210%. So the question is, do you want to feel good that you’ve accomplished 95% or get to that 210% (which feels like 70%).

But It’s Worth It

Working at Amazon is about being a leader—and being a leader is hard. Things are never finished. Once you’ve solved one customer need, you’ve immediately got another one to fix. But that doesn’t mean it isn’t fun and worthwhile. Just like at the gym, you come out of it stronger and more powerful. Leadership takes courage and a willingness to fail. Take it from Teddy Roosevelt who said:

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.

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You Think You’re Better Than Me?! An Open Letter to the Grammar Police

I was at my shul last week and got into an interesting argument with my friend Bill Schwartz. I said, “Bill, the reason you feel this way is that you’re older than me.”

“Than I,” he corrected me.

“No. I really think it’s ‘than me.’ It’s clearly the object of the sentence.”

“Let’s ask my wife Janet. She used to be an English teacher.”

“It’s ‘than I,'” said Janet.

“OK, I said. I’ll look it up and get back to you.”

“Great,” said Bill. “I love receiving email.”

So I looked it up and I found some interesting pieces. My favorite is this bit from Merriam-Webster:

Some people think they’re better than you because they say “better than I” instead of “better than me.”

They’re not, of course. They’re just among the select group of grammar enthusiasts who think that than can only be a conjunction. You, on the hand, recognize that it can also be a preposition.

That’s right: whether you say “better than me,” “taller than I,” or “more annoying than they” has to do with grammatical categories that we typically only consider when a teacher asks us to.

But the bigger issue is believing that there’s a “right grammar.” John McWhorter is a Professor at Columbia University who writes about how grammar is more a fashion than anything else. McWhorter writes:

An especially enlightening read is William Cobbett’s book-length lecture to his son called “A Grammar of the English Language.” Cobbett’s sense of what good English was in 1818 seems, in 2012, so bizarre we can scarcely imagine someone speaking in such a way and being taken seriously.

To Cobbett, the past tense forms awoke, blew,  built, burst, clung, dealt, dug, drew, froze, grew, hung, meant, spat, stung, swept, swam, threw and wove were all mistakes. The well-spoken person, Cobbett instructed, swimmed yesterday and builded a house last year. In Google’s handy Ngram viewer, using data from millions of books over several centuries, one can see that builded only started falling out of disuse around 1920. Not for any reason; no one discovered that builded was somehow elementally deficient. Fashion changed.

So why was Bill Schwartz so insistent on “better than I?” Let’s use Google Ngram to see the historical trends of these two phrases. You can click on the graphic to interact with it.

As you can see, when Bill was in school, “better than I” was the fashion. But don’t lose hope, “better than me” is coming on strong!

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My Blog as a Jewish Folk Tale

As I think about the sensibility that I have in this blog and the stories I tell, there’s a certain Jewishness to it. After reading the book A Treasury of Jewish Folklore, I can see it clearly. There’s an ironic wit of the underdog in Jewish storytelling that’s been passed down for generations. If you’re unfamiliar with the Jewish storyteller, take a look at Eddie Murphy playing “Old Jewish Man” from the end of the Movie Coming to America.

Jewish folk tales to a great job of explaining how I think about my blog. For example, my goal in this blog is to use stories from my life to make interesting points. But there’s a much better explanation through the following folk tale.

The Preacher of Dubno, Jacob Krantz, was once asked why parables have such persuasive power over people. The Preacher replied, “I will explain this by means of a parable.”

“It happened once that Truth walked about the streets as naked as his mother bore him. Naturally, people were scandalized and wouldn’t let him into their houses. Whoever saw him got frightened and ran away.

“And so as Truth wandered through the streets brooding over his troubles he met Parable. Parable was gaily decked out in fine clothes and was a sight to see. He asked, ‘Tell me, what is the meaning of all this? Why do you walk about naked and looking so woebegone?’

“Truth shook his head sadly and replied, ‘Everything is going downhill with me, brother. I’ve gotten so old and decrepit that everybody avoids me.’

“‘What you’re saying makes no sense,’ said Parable. “People are not giving you a wide berth because you are old. Take me, for instance, I am no younger than you. Nonetheless, the older I get the more attractive people find me. Just let me confide a secret to you about people. They don’t like things plain and bare but dressed up prettily and a little artificial. I’ll tell you what. I will lend you some fine clothes like mine and you’ll soon see how people will take to you.’

“Truth followed this advice and decked himself out in Parable’s gay clothes. And lo and behold! People no longer shunned him but welcomed him heartily. Since that time Truth and Parable are to be seen as inseparable companions, esteemed and loved by all.”

I also like to take examples and then write blog posts around them. The theory surrounding the example is subservient to the example itself. That’s an annoyingly complicated way of saying something better described in the following folk tale.

Once Rabbi Elijah, the Gaon of Vilna, said to his friend, the Preacher of Dubno, “Tell me, Jacob, how in the world do you happen to find the right parable to every subject?”

The Preacher of Dubno answered, “I will explain to you my parabolic method by means of a parable. Once there was a nobleman who entered his son in a military academy to learn the art of musketry. After five years the son learned all there was to be learned about shooting and, in proof of his excellence, was awarded a diploma and a gold medal.

“Upon his way home after graduation he halted at a village to rest his horses. In the courtyard he noticed on the wall of a stable a number of chalk circles and right in the center of each was a bullet hole.

“The young nobleman regarded the circles with astonishment. Who in the world could have been the wonderful marksman whose aim was so unerringly true? In what military academy could he have studied and what kind of medals had he received for his marksmanship!

“After considerable inquiry he found the sharpshooter. To his amazement,  it was a small Jewish boy, barefoot and in tatters.

“‘Who taught you to shoot so well?’ the young nobleman asked him.

“The boy explained, ‘First I shoot at the wall. Then I take a piece of chalk and draw circles around the holes.’

Though I hadn’t thought of it, I’ve been using some of the wisdom of the ages to craft this blog. I guess I wasn’t just messing around and having fun.