Who is Robert Schlaff?

I’m a devoted father and husband to an awesome family and work at AIG as a digital product manager. For more information about me, please visit my LinkedIn profile or my Facebook page.


Rob’s Cool Tools

This is a website of my cool tools. A “cool tool” is anything that is tried and true to make your life better. Kevin Kelly coined the term on his Cool Tools website that is a more modern and digital version of the Whole Earth Catalog. The Whole Earth Catalog might have the best motto ever — Stay Hungry, Stay Foolish which Steve Jobs quoted in his famous Stanford Commencement Address.

Spaceman by Mike Massimino

“Every generation of astronauts need a storyteller — a person with wit, humor and passion, who has lived our collective dreams of space exploration and returned to tell us all about it. Mike Massimino is that person. He’s that astronaut. And this is his story.”

— Neil DeGrasse Tyson

Why do we send people to space? We do it to further the scientific mission of space exploration — right? But that’s only part of the story. It’s often cheaper to send unmanned probes. The other reason we send people into space is because we can. Massimino says, “The Russians got to the moon before we did. But no one cared because they didn’t put people up there.”  In fact, the budget for NASA didn’t really take off until Kennedy made it a race to put a man on the moon. Then the Apollo program became HUGE (peaking at over 4% of the federal budget). The book Spaceman by Mike Massimino (read by the author) does an excellent job of telling that story of exploration.

But in order for people to really care about space flight, astronauts need to tell their stories. Massimino does just that. Here are my big 3 takeaways from the book:

  1. It’s hard to become an astronaut. As with any expedition, the journey to become an astronaut is an extremely difficult one. Massimino wanted to be an astronaut since he was a six-year-old growing up on Long Island and dedicated his life to the goal. Focused on this, he got a graduate degree at MIT and worked at the Johnson Space Center with the hope that he could increase his chances. While doing this, he was rejected four times. The most serious issue was his unaided eyesight which was 20/350 vs. a required 20/200. He eventually overcame this hurdle as well, spending years going to vision therapy to improve his eyesight within the acceptable range.
  2. Astronauts are heroes. Heroes are people who take a huge personal risk in the pursuit of something greater. When astronauts go up into space, they know they might not make it back. He tells the story of how he dealt with the death of his friend Elon Ramon and the other shuttle astronauts that died in the Columbia disaster. I remember being shocked when the Columbia blew up, thinking “How could this happen?!” But the astronauts knew that they’ve got about a one in a hundred chance of exploding up in space. Their families know that this might be the last time they see them. Massimino talks about the process that NASA has for this. NASA makes sure that each family as an astronaut “family escort” when they go up in space. This is the person who ensures that if things do go wrong, there’s an astronaut taking care of the family and ushering them away. The most telling anecdote is that the family must pack all of their bags before a space flight — even though they’re coming back to the same hotel that night if all goes well.
  3. But that doesn’t mean that the expedition it can’t be fun. It’s fun for the reader when Massimino shares his stories about the Mets or John Glenn. But he also makes the astronaut training fun. For example, one of the big requirements of spaceflight is to spend 25 hours a month flying in a T-38 trainer. That’s the equivalent of 2 round trips from New York to LA each month. But Massimino shows how awesome that can be. You can go up and do acrobatic maneuvers and pretend that you’re in the movie Top Gun. Or you can just head to any airport in the US to grab some lunch. And you’re MANDATED to do it.

Overall it’s a really amazing book. It’s a compelling read/listen and I learned a whole lot. What else could you want in a book?


A Very Brief History of Mixed Reality and Disney

When we think about Augmented Reality or Mixed Reality, we’re tempted to think this is a very new thing. Take The Void for instance. You can walk through a space that’s literally “painted” with virtual reality textures. I experienced The Void at Madame Tussauds in Times Square last year and it was awesome!

But mixed reality has actually been with us for quite a while. Take a look at a typical Disney experience. Mickey Mouse literally opens the Magic Kingdom to guests each morning. Of course it’s a man (or woman) in a costume dancing around while the virtual voice is piped in through speakers. This lets you really be part of a Disney experience!

But this combination of real life and cartoons is nothing new for Disney. Take a look at this early Disney movie where a real life Alice is transported in a cartoon wonderland.

But it goes back even further in animation. I just came across the first mixed reality movie The Enchanted Drawing. Not only is it the first mixed reality movie, it’s also the first animated movie!

The Speed of Technology OR Forget Being Thankful for Your iPhone, Be Thankful For the Elimination of Cholera

I just came back from a technology conference. I felt like it was mandatory for each speaker to talk about the speed of technology. The problem is that most people tell this story in a highly boring way.  Some use high level markers like the industrial revolution, the discovery of the telephone, the first TV broadcast, etc. Other people just say things like “Remember, just 10 years ago the iPhone was created.”

A few years ago, when I gave a speech, I found some great data in a project by the National Academy of Sciences  Greatest Engineering Achievements of the 20th Century National Academy of Engineering. As part of the book, they showed what things were like before major inventions changed our lives. Some of my favorite examples:

  • Health: At the turn of the last century, indoor plumbing was not common. Raw sewage was often dumped directly into streets and open gutters which went straight into rivers and lakes, many of which were sources of drinking water. Waterborne diseases were the 3rd leading cause of death.

  • Household Appliances: In 1930 a popular women’s magazine asked readers “How many times have you wished you could push a button and have all your household chores performed for you?” This was decades before modern conveniences like dishwashers and microwaves were possible.
  • Cars: In 1904 there were a grand total of 141 miles of paved roads outside of cities. The first crossing of the continent by car, in 1903, required 44 days of hard driving.
  • Telecom: Telephones were initially sold in pairs. The first customer, a Boston banker, leased a pair for his office and home and needed to purchase a private line to join them.

If you like this sort of thing, Tim Hartford has a fascinating podcast called 50 Things that Made the Modern Economy.

When AI Get’s Personal OR You’re Not Supposed to Talk About That!

A few months ago Microsoft released Seeing AI. This is a tool created by a blind product manager to help blind people. It’s trying to using computer vision to replace lost sight.

The most interesting piece is the person functionality. This is a fairly transparent implementation of Microsoft’s Face API. The Face API has a number characteristics that it can determine including hair color,  emotion,  glasses, facial hair, makeup, smiling, gender, and age. Computer geeks, take a look at Face API, it’s pretty awesome. Here’s an example of the person functionality from Seeing.ai showing off Face API.

It’s a great party trick to show your friends how AI can figure out all this stuff. The most interesting characteristic is age. Microsoft thinks so too and created an entire website called how-old.net.

It’s a great party trick so I started bringing it out at parties. But there was the problem. People who skewed older than they really were started saying “Hey, that’s not cool.” I started to realize that the app didn’t have a lot of tact.

It was like a little kid saying, “Mommy, that lady looks 45.”

And the woman saying back, “My Lord! Don’t you have any manners!”

This is similar to a scene in the Netflix series Atypical about Sam, a character with Autism Spectrum Disorder (formerly called Aspergers Syndrome). Sam doesn’t read emotions very well and is often too honest — not taking into account other people’s feelings.
At one point Sam made a list of the Pro’s and Con’s of Paige, his prospective girlfriend. Paige found an imprint of the list and used a pencil to read it.
Paige with Sam’s list of Pro’s and Cons about her.
To paraphrase their conversation:
“Why would you do that? You called me bossy and said I’m always interrupting people,” said Paige.
“But I also said that you had very clean shoes and had a nice neutral smell. So there were some good things in there,” said Sam.
“Ugh. You’re just not supposed to write that stuff down. It’s rude.”
And that’s the inherant problem with the way Face API displays people’s age. Making these things too transparent is just rude.
From all this, I’ve learned 3 things.
  1. It’s kind of creepy how AI can take things from the real world and “know” things about you.
  2. When building a computer program, features like “age” are useful in doing things like matching or making predictions but should generally be hidden from the end user.
  3. It’s much better to use this data for a different purpose, like figuring out which piece of artwork you look like.


Questions from a Reader

Hi Everyone!

In this email, I’m answering some questions from a reader.


I really like what you put on this site. I’ve tried to blog myself but could use your advice on the following topics:

  1. Why write about something when you know that there’s bound to be someone on the internet that has written the same thing – likely better than you? Wouldn’t it make more sense to just link to that?
  2. How do you decide what to write about?
  3. How can I do what you do? Whenever I sit down to write something, I find that I want to write a treatise and I never get finished with it.
  4. How do I subscribe to your blog?


I’ll answer these questions one at a time.

Why write about something when you know that there’s bound to be someone on the internet that has written the same thing – likely better than you? Wouldn’t it make more sense to just link to that?

That’s a good point Dave. Here are a few reasons why I write rather than link:

  1. It’s not worth comparing myself to others. There’s always someone in the world who’s doing something better than me. But if I’m writing about something personal that means something to me, hopefully, I can bring something new to the conversation.
  2. Some people (like you) seem to be interested in what I write.
  3. To paraphrase Maria Popova from Brain Pickings, “I’m writing for myself. If other people want to read this that’s great. But I’m writing for me and not them.”
  4. It’s fun to write.
  5. The best way to become a better writer is to write more. Jeff Atwood, co-founder of Stack Exchange, has some great advice on how to be a great blogger. He says “If you can demonstrate a willingness to write, and a desire to keep continually improving your writing, you will eventually be successful.”
  6. Having a blog becomes a personal record of your thoughts and ideas. It becomes a record of who you are – hopefully of your best self.
  7. Think about your readers. If you look at my first posts I had a lot of links and quoted a lot of sources. This makes it difficult for your readers who just don’t have a lot of time. Paradoxically, by writing a little more, you’re having your readers read a lot less.
  8. You need to be confident in yourself that you have something useful to say. But you need to have your own ideas – not just parrot the ideas of others.

How do you decide what to write about?

I don’t decide what to write about as much as it finds me. I know it sounds corny but it’s true. I have a post a few weeks ago about the process I’m using.

I keep a prioritized list of ideas. When I look at the top of that list, I find a few things that are really exciting and fun to write about. I generally say, “Wow, that’s a really fun idea I’ve put on my list.”

How can I do what you do? Whenever I sit down to write something, I find that I want to write a treatise and I never get finished with it.

Going back to my previous post about writing, I’ll pick a topic that seems pretty exciting and try to figure out how I can get it across in the shortest amount possible. That keeps the boring stuff a minimum and lets me get done with pieces faster. Then I only write about things while they are still interesting. That’s what keeps it fun.

Another way to think about this is the Feynman Method of understanding:

  1. Describe the topic on one sheet of paper
  2. Simplify it so that it can be read by a non-specialist reader
  3. Repeat until you have gotten it simple enough

By the way, there’s a pretty cool and short video about Feynman’s view on what it really means to understand something.

Can I get notifications of your latest posts?

Yes you can! Just go to the bottom of the right column (on a desktop) or the bottom of the page (on mobile).

Thanks for your questions!

How to Avoid Losing Things at the Airport

I was travelling today, having a quick breakfast in Charlotte, NC, before heading into to work. When I left the hotel room, I had a roller bag with me. I finished breakfast and started heading to work. A minute later my phone rang.

“You forgot your bag at breakfast,” said the super nice Charlotte woman. I went back the 50 feet and picked up my bag.

This reminded me of the most useful travel tip that I know:

  1. Always make sure that your luggage tag has your cell phone on it.
  2. Stick a business card onto your laptop (with your cell phone on it). This is mainly for security at the airport. It’s easy to forget that you’ve taken your laptop out of your bag when you’re in a rush to catch a flight. And if you do remember, it’s easy to accidentally pick up someone else’s laptop.

Bonus trivia of the day! On an airplane, I always hear them talking about “Putting your rollerboard bags in the overhead compartment.” I just learned that the pilot is saying “roll aboard” not “rollerboard.” Now that makes much more sense.

Technology Through the Generations OR What Do You Mean by “Film?”

Alan Kay said, “Technology is anything invented after you were born.” While that makes sense intuitively, it’s hard to see in real life. To make this more tangible let me take you back 8 years.

It was early 2010 and we were in Key West for Jeff and Debbie Katersky‘s wedding. Debbie’s niece Carly was about 8 at the time and was given a single use film camera to take pictures at the wedding. This was her first experience with a film camera.

“How do I know what I’m taking a picture of?” Carly asked, pointing to the back of the screen.

“You look through this viewfinder right here,” I said.

“OK…” said Carly, squinting to look through the viewfinder. “But how do I see the pictures once I’ve taken them?”

“You won’t be able to see the pictures. They’re stored inside the camera,” I said.

“Oh, so they get emailed automatically?” she says, excited that she’s starting to understand things.

“No. They don’t get emailed. They stay on the film in the camera. Then between each picture, you have to turn the knob at the top to wind the film.”

“Why do you have to do that?” she asked, thoroughly puzzled.

“Because all the pictures are stored on film, which then needs to be developed. Because of the film you need to be very careful not to open up the back or all the pictures will be destroyed,” I said.

“So that means they get deleted?” she says as she starts opening the camera.

“No! Don’t do that!” I yelled, running to stop her. “They won’t get deleted. If you open up the back all the pictures will be ruined!”

Carly made it through the wedding taking her pictures. And like all photographers with film cameras, she got 1 or 2 good shots on her roll of 24.

Be Careful with Your Assumptions OR Who Would Have Thought That Would Happen

How to Cheat at Hangman

When I was at Yale, I remember taking our most famous computer science class, CS223, with Professor Stanley Eisenstat.

Professor Eisenstat wrote out a game of hangman on the board with 3 letters filled out:


We had 8 guesses to get this right. The class started shouting out different possibilities. We started very confidently with will, kill, mill … this went on for quite a while as we gradually lost that confidence. Then Professor Eisenstat told us that there were many different words that this could be — far more than 8. Bill, Dill, Fill, Gill, Hill, Jill, Kill, Mill, Pill, Sill, Till, and Will. 12 words in fact. Here’s where the cheating comes in. Because Professor Eisenstat hadn’t committed to an answer beforehand, there was no way that we could win the game. When we chose a letter, he removed that word from the set of possible winners. He always had an option that we hadn’t chosen.

Professor Eisenstat Teaching How to Cheat at Hangman (pic via Twitter)

This was used as an example of an adversary that prevents a program from getting its job done. It also shows that what could be an easy problem is often far more difficult than it first appears.


Another interesting situation came up my freshman year. It was a beautiful day and we were sitting outside in a seminar called “Perspectives on Science.” As we were sitting on the lawn under a tree, one of my classmates was performing a demonstration of how probability works. If you flip a coin a large number of times, half of the time will be heads and the other half tails.

“Can someone give me a quarter?” she asked the group. My friend Christine Aidala excitedly reached into her pocket and grabbed a quarter. The first person flipped the coin.

“Heads,” they said.

“Heads,” the second said.







By this time the quarter came back to the leader who examined the coin. “Who walks around with a two headed quarter?!” she blurted out in surprise. As it turns out, Christine did. At the time, we were obsessed about Tom Stoppard’s Rosencrantz and Guildenstern are  Dead which includes a scene where the laws of probability are broken with a coin that continuously lands on heads. So Christine got one.

So remember, when you’re writing a program or a business proposal that it’s fine to make assumptions. But don’t be surprised if they go horribly awry.


Malcolm Gladwell’s Favorite Writers and Storytellers

Malcolm Gladwell is one of the best writers of our generation. That’s not to say he’s always right. As he likes to say, “I hope you find my work entertaining even when it’s wrong.” Gladwell has done some amazing stuff as a magazine writer, book writer, speaker, and even podcast host. If you want to watch some amazing talks, check out: The Spaghetti Sauce Talk and The Coke and Pepsi Talk. But who are the people that Malcolm Gladwell thinks are the best writers and speakers?

The Spaghetti Sauce Talk:

The Coke and Pepsi Talk:

On Great Writers

From the Longform Podcast interview with Malcolm Gladwell (starting at 28:18. Transcript provided by Longform)

My great hero as a writer is Michael Lewis. I just think Michael Lewis, believe it or not, is the most underrated writer of my generation. I think he is the one who will be read 50 years from now. And I think what he does is so extraordinary, from a kind of degree of difficulty standpoint. The Big Short is a gripping book, fascinating, utterly gripping book about derivatives. It blows me away how insanely hard that book was to do, and it’s brilliant. The Blind Side, I think, it might be the most perfect book I’ve read in 25 years. I don’t think there’s a single word in that that I would change. I just think it has everything. But he uses no science, right? Very little.

It’s all story. But he does more work in his stories, makes much more profound points than I do by dragging in all these sociologists and psychologists. He’s proved to me that, if you can tell a story properly, you don’t need this kind of scaffolding. You can just tell the story. And so, I’ve been trying, not entirely successfully, but trying to move in that direction over the last couple books.

I don’t think people realize how hard it is to do a single narrative book. That’s one of the things I admire about Michael Lewis. He seems to be able to do it effortlessly. I don’t even think I could pull it off. Maybe it’s because I’ve never found an individual whose story is rich enough. But, maybe I’m just not as good at developing a single story. I just think that’s kind of beyond me a little bit. … I would lose faith in my ability to keep the reader engaged. I’m much too nervous a writer. Whereas the amount of self-confidence you feel in Michael Lewis’s work, or Janet Malcolm’s work … she’s so extraordinarily sure of her gift, she’s not in any hurry to start and she knows you’ll stick with her because she knows she will deliver. To use a sports metaphor, Janet Malcolm and Michael Lewis are the people who are quite happy to take the last shot. I’m going to pass.

Apparently, Lewis and Gladwell are friends and appear together often.

In addition to being a compelling author, Gladwell also makes phenomenal speeches. My favorite Malcolm Gladwell speeches were given about 10 years ago: The Spaghetti Sauce Talk and The Coke and Pepsi Talk. Both of these are brilliant examples of storytelling and really show the difference between reading an article and giving a performance.

In his interview with Tim Ferris (starting at about 28 minutes), Gladwell talked about how difficult it is to give a great speech. It’s not about reading an article in front of a group, it takes a lot more work than that. Then Ferriss asks Gladwell, “Is there anyone in the world of speaking alive or dead who is the Michael Lewis for you.” Below is Gladwell’s answer. Note that I used YouTube’s transcript function  and tried editing it so it makes sense on the page:

I once went to a birthday party for an old friend of mine, Anne Applebaum, in England.  Now first of all the English are way better at giving speeches than we are. And secondly, we were talking about the creme de la creme of English speech givers.  Like serious Cambridge and Oxford debating society kind of people.

Niall Ferguson, the historian, gave a birthday toast which is just the best toast I’ve ever heard in my life. I mean it was like so much better than anything I had ever heard — like on another level. I was like oh my god that’s good. And part of what made it genius was he really gave you the impression he was making it up on the spot. Now he might actually have done that. He may be so good he could do that.

The conceit was that it was totally spontaneous. It was so cleverly done and so hilarious. And one of the ways it was so charming was the ways in which he was wrong. Part of the joke was he was going to make this elaborate hilarious argument about Anne who was turning fifty. And half of the stuff that he was going to say was not right. He spun a theory about the weekend and about her birthday and about her friends that was like hilarious because it was not accurate. And he did it with such panache. First of all that would never have occurred to me to make stuff up in such a dramatic way. But also I can’t do off-the-cuff. Ever since then I just worship the guy. I just think I think he walks on water.

I had Niall as a professor when I was at NYU for business school and he was just amazing. His books (like The Ascent of Money) and television programs (like The Ascent of Money) are really amazing. If you want to see him giving more of a speech like Malcolm mentioned, though a lot less funny, you can watch his speech at the Sydney Opera House.

What Makes a Great Consultant OR the Best Appliance Repairman Ever

What makes a great consultant? It’s someone who get’s the job done quickly,  teaches me instead of selling me and gives me the advice for the future. I’ve also got a great example of a bad consultant. The best consultant that I’ve met recently was the guy that fixed my refrigerator.

The Issue

Our Viking refrigerator was broken. The water filter was stuck. It was so badly stuck that in the act of trying to get it out, I broke the holder for the water filter. At this point, we needed to call in an expert before my “home improvement” project became a “buy another fridge” project.

Calling for help

So I called Len’s Appliance in Brooklyn (718) 238-3200. In the past, I’ve learned its useful for me to be there when the repairman comes rather than trying to rope someone else in. If it’s a bad repairman, I can avoid the damage. If it’s a good repairman, there’s a lot I can learn.


Get in Quick, Get It Done and Get Out

He came in and fixed the problem within 10 seconds. He grabbed the filter, disengaged it from the holder and twisted to remove the filter. The filter holder itself was made horribly. Not only is it very flimsy but it requires a lot of force in an awkward position to remove it. This is not a good combination. The force needed to take the filter out of the refrigerator stresses the holder so every time I change the filter, it’s always on the verge of breaking it. Once he removed the filter from its holder he could easily apply enough force to remove the filter. Wow that’s bad design.

Teach Me to Fish Rather Than Selling Me a Fish

Now remember, I called Len’s because of the broken filter holder.  After removing the filter he told me where I could go to buy a replacement. It was fairly easy to install myself and it wouldn’t be worth the $125 service call for him to reinstall it. Then he paused. “On second thought,” he said, “you don’t actually need this piece at all.” He explained that the poorly designed holder that made it difficult to remove the filter was only in use DURING the filter change process. So it actually wasn’t necessary at all.

Give Me Advice for the Future

Then he told me about the refrigerator itself. We’d bought this Viking fridge because we were under the impression that this fridge was unique in its size. This is a tiny Manhattan kitchen where space is a premium. He mentioned that the fridge was actually a standard size which is great! He also said that it’s out of production now and that spare parts are more expensive and will continue to go up in price.  Eventually, the parts will be impossible to buy.

Did you know that refrigerators are only meant to last 7 years? That’s what he told us. That big expensive kitchen appliance that you thought would last forever goes out of production every 7 years and you’ll need to buy a new one when it breaks. He told us that if the refrigerator breaks badly, it’s probably worth just buying a new one.   Oh, and from what he’s seen, the cheaper models like GE break less often than the Viking ones.

He felt bad that he was charging me $125 for the visit when he was only in my apartment for 15 minutes. But this was the best repair visit that I’d ever had.

Now read about a really bad consultant.