Casey Neistat

Casey Neistat (@CaseyNeistat) joined Tim Ferriss (@TFerriss) to talk about YouTube, creativity, and the value of scarcity.

I started to follow Neistat after this interview posted and dig through his archives. It felt weird kinda weird. It seems like a lot of his fans are teens, tweens, and being weaned. They’re really young. It reminded me of what Judd Apatow said about a Taylor Swift concert. You can’t seem to disinterested or too interested. You have to find the median of watching with respect.

That’s how I felt about Neistat. His videos are cool. Some are instructions (I’m watching this to learn about that I told myself). Some are less so. Some seem like too much information. I didn’t know how to feel.

Then I realized it didn’t matter. The more I thought about this, the less I cared. Neistat (like everyone else on this blog) speaks about being human. Though each person is different, their stories are largely the same.

Patrick O’Shaughnessy pointed this out in his recent (monthly and recommended) newsletter on books.

“One of Schopenhauer’s main points is that way too many authors simply summarize/synthesize what has already been written on a subject. Given the amount that I read I see this all the time. Even some books that seem very original are not at all! For example, I thought Thiel’s Zero to One was incredibly original until I read de Bono, who in turn I thought was incredibly original until I read Koestler (I’ve yet to find Koestler’s antecedent or superior). For the record I still like Thiel and de Bono, just not as much as I like Koestler.”

That’s almost exactly what this blog is! None of these stories are original. They’re all part of the same story.

It’s like music. Everyone sings in the song of life, but different people can hear different keys. Neistat resonates with people because his story is one that people can hear. Another “key for the song of life,” are the Stoics. Quotes like this resonate with me. 

1-woman_mountain

It doesn’t matter who Casey Neistat’s fans are. Gary Vaynerchuk said that when a new app comes out don’t look at the foolish ways people use it (in this case he was talking about sexting). Instead, think about how you can use it well. It’s the same for the influences in your life.

If Neistat says something that resonates with me, that’s all I need to hear. So what did he say that was impactful? The importance of finding your lane, how not to not be huge on YouTube, who is successful, 2 free video creation tools, when to filter your life, a business idea, and books and movies to enjoy.

One word or warning, this post is a monster. You may want a snack. 

Ready?

Find your lane. For Neistat it was a bike lane.

The start of the interview is about Neistat’s history and early career. There’s not much to point out here except that Neistat had a hard life. “I grew up in the poor part of Connecticut,” Neistat says. He ran away from home, dropped out of high school, and had a son when he was 17.

Things changed when he found filmmaking. His brother showed him an iMac and Neistat bought one too. Then things really took off when people started paying him for his work. Asking for $5,000 for a job he would do for $100 was a big moment for him.

Success – in relative terms – continued when Neistat made the video Bike Lanes. (Here’s the first of many YouTube videos on this post.)

Ferriss asks how Neistat was inspired and Casey says, “whatever I care about I make a movie about.” This, we should note.

arcreactorIf we care about something so much that we act on it, we’ve found something important. We’ve found an energy source. It’s like Arc Reactor in Iron Man.

Wayne Dyer compared it to a burning flame inside us. Gary Vaynerchuk calls it hustle. Ramit Sethi sees a positive feedback system where passion feeds skill which feeds passion and so on.

Everyone who succeeds greatly says; your passion must fuel furious work.

That’s what Neistat has done. He points this out many times in the interview with Ferriss and on his YouTube Channel. Making movies, he says, is not about the gear. He started to make films with the simplest equipment and the most basic software. Those are the surface parts of storytelling, the tip of the iceberg. To make something great you need the deeper understanding. 

Look at Hollywood movies, Neistat says. They have the talent, money, gear, time, experience, and connections. They have everything you need, but it doesn’t always work out. Why does one Matt Damon movie about space (The Martian) make more than twice as much money as another (Elysium)?

When Seth Godin said this, “Stories are never about the person telling the story, they are always about the person hearing it.” That’s the type of thing you have use your passion to learn. You don’t need fancy camera gear anymore than you need a fancy blog or book or narration by someone famous. What is paramount is story.

Neistat notes that because he never graduated from film school (much less high school), he learned things his own way.  School is good, Neistat says, because it teaches you to get from A –> B. If you don’t know how though, you need to figure out your own way, and it could be an advantage.  That’s what he did. (Watch this one minute sequence, 3:34-4:44)

Neistat developed the “craftsman mindset.” Coined by Cal Newport in his book, So Good They Can’t Ignore You, it’s the focus to build valuable skills. Valuable skills, Newport writes, are the only things that get you great jobs.

When Neistat made Make it Count for Nike, the video opens with this scrolling text:

“Nike asked me to make a movie about what it means to #makeitcount. Instead of making their movie I spent the entire budget traveling around the world with my friend Max. We’d keep going until the money ran out. It took 10 days.”

That sounds great. It’s rebellious. It smells like following your passion. But it hides a bit of the truth.  That video, Neistat points out to Ferriss, was the 3rd video in a series for Nike. He had already done two video for them and this one had the “budget of what Nike usually pays for snacks and drinks.”

On the surface it looks like “follow your passion,” but it’s deeper than that. Neistat was an expert filmmaker who had existing relationships and created career capital. Neistat’s career mimics Newport’s framework so much, he could have been a case study the book. Newport writes:

“Career capital theory argues that the traits that define great work are rare and valuable, and if you want these in your working life, you must first build up rare and valuable skills to offer in return.”

Neistat worked furiously to create these skills. He’s doing this again for his company – Beme. How? Just watch what Ferriss calls “a brutal schedule.”

You don’t need to do that. You probably shouldn’t do that. Why? Because you’re not Casey Neistat. That’s his lane. Ferriss, you, me – it doesn’t matter what we do, but we have to do something different. We have to find our own lane.  Arthur Samberg noted that we are our competitive advantage. No one does you better than you.

How can you do it on YouTube?

How to not not be huge on YouTube.

Neistat has no idea how to get an enormous audience on YouTube, but he does offer something helpful – how not to be huge. Let’s break down the framework (macro idea of answering questions) here before we talk about how to gain an audience (micro idea of YouTube followers).  

What Neistat has done is invert the question, and it’s a helpful tool. Tren Griffin noted that it’s easier to solve problems by looking forward and backwards at them. Instead of asking, “how do I get a better job?” Griffin might suggest you ask, “how do I get better for my job?”

Michael Lombardi said that The New England Patriots find NFL players this way. “Scouting’s not about finding players,” Lombardi says, “Scouting is about eliminating players.”

Ferriss’s question, how do you get YouTube subscribers is hard to answer. No one knows.  Neistat reverses the question and answers, how do you NOT get YouTube subscribers. 

This, Neistat says, is much easier:

“The biggest waste of energy and resources on YouTube is creators trying to copy and be exactly like someone else. The only thing that succeeds on YouTube are the people that think outside the box and do new things.”

If you want to not succeed, do what everyone else is doing. Find the lanes other people are in. 

This gives us something to work with. Knowing what not to do can be as helpful as knowing what to do. What to live a long time? Don’t smoke, drive motorcycles, or weigh more than you should. Those three don’t-dos are more helpful than any three do-do’s. 

“Trying to copy and be exactly like someone else,” almost never works. Peter Thiel notes the value of being different. Brett Steenbarger said, “you don’t find generic super-successful traders.” Lewis Howes played handball because it was different.

Being different is really important, but how do you actually do it?

Step 1: Stretch. Steven Kotler said that the best extreme athletes stretch themselves 4% past what they think is possible. These small changes add up. 

Step 2: Have wide inspirations. Neil Gaiman said that if you want to be the next Tolkien, don’t read Tolkien. 

Step 3: Remix. Austin Kleon said, “everything is a remix.” 

Step 4: Persist. Timing is impossible to nail. The only thing you can do is keeping doing it. Mark Cuban offered streaming music years too early. Trip Adler had the idea for ride sharing years too early. Neil Strauss released his book the same weekend as Hurricane Katrina. You have to survive.

Neistat has a suggestion too. The only way to find your own path is to start.” (click to tweet)

A perk of  being different is that you don’t have to be that good. When you find something new, there are fewer people doing it and it’s easier to stand out. Neistat says to start and to do it everyday. You need a lot of repetitions.  Malcolm Gladwell gave this same advice to people who want to write. Write for a newspaper, Gladwell says. It will force you to do many things, one of which is to get used to writing a huge volume of stuff.

Practice being the best version of you. And for pete’s sake, make sure you define success as something besides fame or money.

Who is successful?

“My grandmother,” Neistat says, “she loved tap dancing and didn’t stop until the day before she died.” Here again, Neistat inverts the question. Rather than think of success as the time spent doing what you enjoy, think of it as the time not spent doing what you dislike. Even the best of things won’t be perfect. 

I like this idea. Seth Rogen and Evan Goldberg both said that making movies isn’t all fun and games. It’s some fun and games, but there’s still work. They’ve applied Neistat’s idea of “less-suckiness” to work by creating a more relaxed work environment. 

Remember, a perfect job is a fallacy. Austin Kleon makes the art he wants to make, speaks across the country, and has written two best-selling books. When James Altucher suggested he was doing what he loved, Kleon stopped him. “I have to push back a little on that,” he said, “every job is still a job.” Jon Acuff had the same experience. Acuff quit the grind, but said he’s “doing a lot of stuff you wouldn’t consider dreamy.”

What success isn’t.

Success isn’t fame, or money. People don’t get this, Judd Apatow said. “It’s hard for people to understand what it’s like to give up all anonymity.”

Bill Murray added:

“I always want to say to people who want to be rich and famous: ‘try being rich first’. See if that doesn’t cover most of it. There’s not much downside to being rich, other than paying taxes and having your relatives ask you for money. But when you become famous, you end up with a 24-hour job.”

But then Murray stops short because it’s not about the money either. T. Harv Eker said that he thought money would make him happy. He got a lot of money, but wasn’t much happier. What is success?

What success is.

Success is loving the process. 

Chris Hadfield calls this creating win-win situations. For Hadfield it was about trying to get to space, but knowing the odds were slim. In his book, An Astronaut’s Guide to Life on Earth he writes:

“It’s probably not going to happen but I should do things that keep me moving in the right direction, just in case – and I should be sure those things interest me, so that whatever happens, I’m happy.”

Those things were the process. Hadfield literally aim for the moon, but enjoyed the work that he did on earth. That’s how to succeed. One a more practical level, Neistat shares 2 free tools anyone can use.

2 free tools.

No, this still isn’t about the right camera. There is no right camera. There are however, two free tools that anyone can use in life: good friends and some scarcity.

“I always try to surround myself with people smarter than I am,” Neistat says. Simon Rich did this too. When it was time to make his television show Man Seeking Woman, he hired people from all his favorite show like The Simpsons and The Office. “I want to feel like I’m barely keeping up,” Rich said.

It can be hard to ask for help. Amanda Palmer spoke (and wrote a book) about this. “If I learned anything from the surprising resonance of my TED Talk it was this: Everybody struggles with asking.”

But allies are out there and you need to find them. Nicholas Megalis found them for his Vines. Brian Koppelman has David Levien to write with.

The second free tool to use is scarcity. I was going to write a lack of money, but that would be conceited. Poverty as a muse sounds romantic. It’s insulting.

In her Harvard commencement speech J.K. Rowling addresses this better than I:

“They (Rowling’s parents) had been poor themselves, and I have since been poor, and I quite agree with them that it is not an ennobling experience. Poverty entails fear, and stress, and sometimes depression; it means a thousand petty humiliations and hardships. Climbing out of poverty by your own efforts, that is indeed something on which to pride yourself, but poverty itself is romanticised only by fools.”

But, there is something here. There’s something in scarcity, in bottoms, in failure. Rowling continued:

“So why do I talk about the benefits of failure? Simply because failure meant a stripping away of the inessential. I stopped pretending to myself that I was anything other than what I was, and began to direct all my energy into finishing the only work that mattered to me. Had I really succeeded at anything else, I might never have found the determination to succeed in the one arena I believed I truly belonged. I was set free, because my greatest fear had been realised, and I was still alive, and I still had a daughter whom I adored, and I had an old typewriter and a big idea. And so rock bottom became the solid foundation on which I rebuilt my life.”

The greatest living author had nothing. Just an old typewriter, a napkin, and a dream. She’s not the only one who tells this story. Scarcity forces people to be creative.

Kevin Kelly said “the lack of money is often an asset because it forces you to innovate. People with money will try to buy a solution, but because you don’t have money, you are forced to invent a solution.”

David Levien said the clipped train ride to work help him to write a better novel.

Tim O’Reilly said that they launched O’Reilly publishing because they didn’t have enough consulting work.

Dick Yuengling said that the brewer adapted because of prohibition.

Neistat says, “don’t blame it on the gear or the lack of resources because it’s never the resources that determine your success. It’s how you use what you have.”

This applies to time too. Austin Kleon and James Altucher both said they’ve seen many people who think that if they only had more time they could do the thing they dream of. It’s not true. Look at Andy Weir.

Weir was a software developer who found himself laid off from work. Between his severance package and savings he could take 3 years off and try to become a professional author. Did he succeed? No. Weir failed.

Out of money, he returned to work. Then the itch came again and he started writing again – all on the side. He wrote a book no one saw. Then the next began as a series of blog posts. People asked him for a format for reading it all at once, so he put it on the Kindle store. A few months later it over 30,000 copies were sold. After than Crown Publishing bought the rights. Then came the movie deal. Andy Weir had good friends that helped him write the book when it was blog posts and he had scarce time to write in. Good friends you’ll have to find on your own. Scarce time though, we have a tip for. It has to do with good signals, Van Halen, and candy.

Signals (what Neistat has in common with Van Halen).

“Everything is given one filter,” Neistat tells Ferriss, “is this good for me and my technology company (Beme), and if the answer is no it gets a pass.” Neistat’s signal is the question, “does this help Beme?”

These one-time filters are everywhere once you look for them:

Richard Feynman got so tired of choosing a dessert, that he resolved to always order chocolate ice cream. That was his dessert filter.

Barry Ritholtz said that he looks at the prices of classic cars as a signal for bull and bear markets, or if people say “ugh” to his trading ideas.

Ramit Sethi said that he looks for specific words when people interview with him.

Stephen Dubner called this, “teaching your garden to weed itself,” and wrote an entire book chapter about it.

Some banks figured out how to filter out dangerous marijuana growers.

The most famous of the signals might come from Van Halen.

The story goes, that when Van Halen was touring they had the latest and greatest light and sound rigs. There was just one problem. Each venue had a different person set them up. The guy who set things up in New York wasn’t the same guy that set things up in Charlotte. So, according to David Lee Roth, Van Halen introduced a wrinkle to their rider.

They said that among the other rock star accoutrements, they wanted a bowl of M&M candy with the brown ones picked out. Some people looked at this as divas being divas, but maybe not. Roth said they did this to see how closely a promoter read the rider. If they removed the brown M&M candy, they probably set up the equipment correctly.

Good signals save people decisions.

A business idea.

Sam Shank founder of Hotels Tonight said that all good business solve two things, time or money (ideally both). Neistat and Ferris both need help to save time interacting with people.

Someone could make a service that queued up responses over multiple channels (YouTube, Twitter, Facebook, Quora, etc.)  optimized for relevancy.

For example, if Neistat posted a video, the service would combine the video comments from YouTube and the Twitter comments into one timeline for Casey to respond to. Further, it would  prioritize by some metric; how long the person followed Neistat, how long they’ve been active on YouTube, how recently they had a question answered, etc. The service could filter out trolls and four letter words as well. 

Then when Neistat or Ferriss had time, they would go to that service and quickly respond to more fans.

Media suggestions.

Neistat say that his two favorite books are The Autobiography of Malcolm X and The Second World War by Keegan. He also recommends The Life and Death Colonel Blimp and Little Dieter Needs to Fly as videos to watch. Ferriss suggests people watch this clip from Miracle for inspiration to work harder.

Neistat suggests podcast listeners check out Make it Count and Draw my Life on YouTube. He says  Ben Brown and Fun for Louis are other good vloggers. Also, listen to Jonny Famous on Spotify.

Parting ways.

Neistat tells Ferriss that he would want a billboard that tells people to “be nice.” Adding, “being nice is really hard work.”

Thanks for reading. Really, thank you. This post was 3300 words. I’m a freelance writer and if you’d like to say “thank” via a $2 donation, you can donate here.

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Judah Friedlander

Judah Friedlander (@JudahWorldChamp) joined Brian Koppelman (@BrianKoppelman) on The Moment podcast. The duo talk about Friedlander’s new book, If the Raindrops United, but cover a lot of other ground too. By the end of the interview I empathized with Friedlander. He’s just a person, who tries hard, and faces challenges. Like everyone else. So many people, from Judd Apatow to Tom Shadyac say that life isn’t about fame or money. It’s about more than that. It sounds like Friedlander has lived this. He’s still unsure of himself (and has good company, check out the Apatow link). He still fails. He’s still looking for more. Here’s hoping he finds it.

There’s more good stuff here. Our route includes, comedy as an advanced thinking technique, starting out, crazy like a fox (but not one bit more), the craftsman mindset, and why you need to start right now.

Ready?

Comedy as an advanced thinking technique.

Koppelman notes that some of the jokes from Friedlander’s book have a deeper message in them. “Yeah they do,” Friedlander says. Judah explains that as he became more popular as a comedian, he started to tour more. More touring meant more places. More places meant new places. There, he began to notice things about America.

Not bad things, but different things. “I started to see how other people lived,” Friedlander said.  Hence the new book, and the book might be the catalyst for Friedlander’s next success.

Phil Rosenthal suggested that people write in different mediums. Friedlander said that stand-up is his “home base,” but because he wrote for 30 Rock, has written other books, his standup is probably better. Judd Apatow said that different forms awaken different neurons. Brian Koppelman writes music for the same effect.

Comedy writers especially need those other neurons to be awake, because comedy requires deep understanding. Jason Zweig challeged himself to write The Devil’s Financial Dictionary to see if he knew what he was talking about. Judd Apatow also said that  comedy requires a deep understanding.

But, we’ve gotten the cart in front of the horse here. Before we become great, we need to start.

Starting out.

“I never realized being a comedian was a thing you could do,” Friedlander says. It wasn’t until he saw stand-up on TV and hte post routine banter that he realized it could be a job. After a set, the show host went up to talk to the comedian, and they would plug wherever they were performing.

lightbulb

This was a lightbulb moment for Friedlander. “I was like, ‘whoa’ You can do this?” he says.  “When I was sixteen, I realized I wanted to do standup.”

A generation earlier Phil Rosenthal missed this. Rosenthal (also on Koppelman’s show) said that he saw actors on television, but that was it. He wanted to do that, but didn’t know what that was.

Seeing may not be part of believing, but it may be part of achieving. In his book, The Talent Code, Dan Coyle noted that many people succeeded in “hotbeds.” His book begins with the story of a Russian Tennis club that graduated a single player to the professional tour. Then four. Then six. Coyle looked around and found that seeing helps achieving in other areas too. 

Malcolm Gladwell worked at a newspaper that challenged him with how much he could write. Later on he wrote Jamacian sprinter are so good for part of the same reason. 

Simon Rich said he wants to be the dumbest one at the writing table.

Austin Kleon suggested people find a group. Nicholas Megalis noted that the internet has made this easier than ever.

In whatever group you start with, make sure you do things a little differently. Try to be crazy like a fox.

Crazy like a fox – but not more.

Projects succeed most when they are different. Naveen Jain had a different internet company. Nearly all of Peter Thiel’s book, Zero to One is about being different:

“All happy companies are different: each one earns a monopoly by solving a unique problem. All failed companies are the same: they failed to escape competition.”

Phil Rosenthal said that he had to make Raymond, not Seinfeld. If he tried to make something like Seinfeld, it would fail. Penn Jillette said not to imitate the Rolling Stones if you like the Rolling Stones. Those guys already nailed that, Jillette says, instead do something different.

How can you be different?

“You can’t be too crazy,” Friedlander warns, “if you get too crazy you’re not functional.” His book is different. That’s good. Friedlander can’t write the book that Jim Gaffigan or B.J. Novak or Tina Fey wrote. Those have been done. He had to do something different than them, and that meant he had to be crazy, crazy like a fox.

How to be crazy like a fox:

Step 1: Stretch. Steven Kotler said that the best extreme athletes stretch themselves 4% past what they think is posible. Do that and you’ll find something new.

Step 2: Have wide inspirations. You need to take ideas from many areas. Neil Gaiman said that if you want to be the next Tolkien, don’t read Tolkien. Jillette said that Guns n Roses idolized the Rolling Stones, but knew they couldn’t imitate them. So they did something different.

Step 3: Remix. “Everything is a remix,” Austin Kleon said. Even the Thiel quote above about being different is a remix of Tolstoy.

Step 4: Persist. Timing is impossible to nail. The only thing you can do is keeping doing it. Mark Cuban offered streaming music years too early. Trip Adler had the idea for ride sharing years too early. Neil Strauss released his book the same weekend as Hurricane Katrina.

Timing something just right is impossible. It’s not like a cruise missile. Instead, you need to persist with your new idea. Oh, and  one more thing.

The craftsman mindset.

“Most people aren’t doing a job well,” Friedlander says. People need the right mindset. Penn Jillette said that he and Teller worked on part of their act for six years. Not a new act. Not even half an act. Two minutes. They spent six years of work for two minutes of material. That’s what makes us great, Jillette said. “The most important thing,” he continued, “is everything.”

This can be lonely work. David Levien said, “it seems brutal when you are toiling away in obscurity.” But you have to focus on getting better.

Cal Newport termed “craftsman mindset” in his book, So Good They Can’t Ignore You. The book title comes from the Steve Martin quote that nobody wants to hear:

“Nobody ever takes note of [my advice], because it’s not the answer they wanted to hear,” Martin said. “What they want to hear is ‘Here’s how you get an agent, here’s how you write a script,’…but I always say, ‘Be so good they can’t ignore you.’”

You have to do the work and get great at something. Let’s have one more example.

If you watched Seinfeld you probably remember Tim Whatley, the dentist who pretended to be Jewish so he could tell Jewish jokes. The actor who played that character was in five episodes of Seinfeld from 1994-1997 but also had 35 other roles during that same time period. Those other shows included the television movie Extreme Blue and the show Teknoman.

One of the writers on Seinfeld remarked that he was constantly auditioning for roles, and when she asked him about what he had been working on, he told her he forgot. He did so many auditions that he couldn’t keep track of them. He was, in Newport’s words, building career capital.

In 2000 that actor was cast as a lead on a network show and he worked on bigger shows like The King of Queens and Family Guy.  But not until 2008 did he reach the upper echelons of his field and win an Emmy Award for playing Walter White on Breaking Bad.

Bryan Cranston is a great example of building up the career capital. It shows in his IMDB profile too, those 35 roles during his time on Seinfeld were for TV movies and shows you’ve probably never heard of. Then his choice of roles became fewer and more selective on shows like The X-Files and Chicago Hope until he was cast in Malcolm in the Middle.

Need more? Check out Gary Vaynerchuk on being an overnight success:

A final note.

It’s time. For whatever you’re doing, it’s time. This was so clear in the Friedlander interview. Judah needs to go for it. That’s easy for me to write, (so easy), but it’s worth pointing out.

There’s no perfect time for anything. Now is the time for Judah to do a stand-up special. Now is the time for you to start something. Now is the only time we have.

In honor of Koppelman, we’ll end on this this.

.

Thanks for reading. Thanks for reading, I’m @mikedariano on Twitter. Wow, you made it to the end of the post. A solid 1600+ words. That’s pretty long online. If you found a few things valuable, you can [donate $2]

Wow, you made it to the end of the post. A solid __ words. That’s like __ pages in a book (and forever online). If you found a few things valuable, you can donate $2.

Judd Apatow

Judd Apatow (@JuddApatow) joined Bill Simmons (@BillSimmons) for a new podcast called, two white dads who sit on the couch and complain. Just kidding. While there is a bit of whining from Simmons (who admits it), it’s very small – and the other parts are quite good. Apatow is funny, humane, and sounds like a great guy to hang out with. 

He’s is on to promote, nothing really. His most recent book is Sick in the Head came out in June 2015 and he produced Trainwreck which is a digital download at the end of 2015. Right now he’s doing some stand-up and he talks about that with Simmons. Here’s a bit of his routine:

What I really wanted from this interview was to hear about how Apatow works, and we get some of that. Seth Rogen and Evan Goldberg both praised Apatow when they talked with Tim Ferriss. It feels like Apatow knows something about living well. Which seems weird. This is the man who created The 40-Year-Old-Virgin, but maybe that’s the point. Maybe the person who created The 40-Year-Old-Virgin is exactly the person who knows a thing or two about life.

A few of the other big ideas; lifestyles of the rich and famous, what stand-up does to the brain, the future of entertainment, and comedy as true understanding.

Ready?

Lifestyles of the rich and famous.

The podcast starts as Apatow and Simmons discuss how people promote their work. It surprises Apatow when people dismiss or knock what other people do. “We’re all trying,” he tells Simmons. It’s not like anyone tries to make an awful movie.

Part of that is being rich and famous. “I love when people talk about some of the difficulties with being famous,” Simmons says, referencing the Apatow and Rock email conversation. “It’s hard for people to understand what it’s like to give up all anonymity,” Apatow says.

Tom Shadyac gave up everything and was happier. Jim Carrey said “I wish everyone could be rich and famous to realize it ain’t it.” Bill Murray added:

“I always want to say to people who want to be rich and famous: ‘try being rich first’. See if that doesn’t cover most of it. There’s not much downside to being rich, other than paying taxes and having your relatives ask you for money. But when you become famous, you end up with a 24-hour job.”

Fame is fickle and is a weak base for life. Naveen Jain noted that if you attach your happiness to something external – whether it’s as grand as fame or simple as kids – you give up control. It’s letting them drive the car. When Phil Rosenthal spoke with Brian Koppelman he was so contemplative about his contentment. Rosenthal wore the Jewish song – Dayenu – like a cloak. Any milestone, like just writing a pilot, would have been enough.

A consistent conclusion for a truly rich life is to look internally. Apatow does this. He’s smitten with his family. Evan Goldberg said his brother’s happy life was how he viewed success. Phil Rosenthal did it. Ryan Holiday wrote a book about how he did it with stoicism. T. Harv Eker saw that a great business wasn’t going to solve this problem. Tom Rath spoke about this too. 

It’s not about being rich and famous, or rich, or famous. Those things are external. They change quickly. It would be like attaching your happiness to the weather – which some people do. Most of those people long for something else. It’s finding something internal. Part of that could be work. 

The 47-year-old comedian.

Why in the world isn’t Apatow making another rom-com? A stoner movie? Why doesn’t he write hilarious television shows? He hears these questions. “When you stretch,” Apatow says, “there are always some people that are so thrilled you are pushing yourself and then there’s always the people who are like, why aren’t you doing the thing you always do?”

Apatow is still making movies and shows, but says he had to do stand-up one last time. “This is the moment,” Apatow says, “where you’ll never do it again. I felt like it was unfinished business.”

Like this unfinished business?

No, not that.

Though Apatow is a famous comedian, there are two parts about his return to stand-up which we should note. 

First, be around good people.

Brian Koppelman used stand-up comedy to unblock his writing. Part of it was being around funny people. That’s key. Koppelman says that those other comedians helped him think differently, they encouraged him, and they failed together. 

If you want to be great at something, Dan Coyle said, you need to be around other people. Coyle calls them “hotbeds.” Austin Kleon calls them a “scenius.” Simon Rich said he wants to feel like he’s barely keeping up. Malcolm Gladwell wrote that part of the reason Jamaican sprinters are so good is because the peer effect is really strong.

Each of these things points you to be around good people.

Second, sharpen your tools.

Apatow echoes Phil Rosenthal, who urged writers to write in different forms. Rosenthal said that if you write for movies, TV, and plays, it’s going to help you be creative in other areas. Koppelman gets this effect when he writes songs. Apatow noted that stand-up, “wakes up some neurons in your head.” It’s true for not just for Hollywood types.

Physicist Richard Feynman writes about this in his book, Surely You’re Joking, Mr. Feynman. Feynman worked in a biology lab. He sat with people from other disciplines at lunch. He studied around the world. He writes, “I got a great reputation for doing integrals, only because my box of tools was different from everybody else’s.” Feynman’s box of tools was bigger than everyone else’s because he learned other things with other people. 

These two things; be around good people and sharpen your tools are not panaceas. “I  always used to think, ‘who cares what you have to say’,” Apatow tells Simmons. It doesn’t matter who cares. What matters is that you tell your story.

Neil Gaiman advocates for people the same way, “There are lots of artists in the world, but there’s only one you. And the only person who has your point of view, is you. If you decide not to make things, all you’ve done is deprive the world of all the stuff that only you could have brought to it.”

Apatow said it took decades to feel this way. He admits to being in a funk for fifteen years after Freaks and Geeks finished. Don’t doubt your story. It’s your competitive advantage said Arthur Samberg. There’s no one that can be Judd Apatow better than Judd Apatow. 

What you do with that is up to you. But, let me make one quick prediction.

A prediction on the future of entertainment.

The old man on the porch role is played by Simmons, and he admits to it during the interview. What happens, he asks, if kids just tweet or gram (is gramming a verb, as in instagramming?). Will that satiate their need to be creative? Simmons wonders what will happen if kids don’t sit down to write a poem or short story. At this point I did wonder how old Simmons was (he’s 46).

But the future never looks like the past. Not only that, it won’t look like the present. Naveen Jain is building a rocket to the moon without any specific plans on what to use it for. Is he worried? Not really. We’ll figure it out along the way, we always do. Kevin Kelly noted that the things we’ll use in twenty five years haven’t even been invented yet. The iPhone only turned 8 in 2015.

Apatow is adapting faster than Simmons. He says that the show he’s doing for Netflix was designed this way. “We are making it with the assumption,” Apatow says, “that people will watch it in two sittings.” The show was created with binge watching in mind. That sounded crazy when I first heard it and then it totally made sense. 

How then do we predict the future?

The only sure prediction is that the future will be different. That said, there is hope. Naveen Jain said that we don’t need to take wild guesses, there are suggestions about what will come next. Like a Hansel and Gretel fairytale (the children who left a trail of crumbs to find their way home), the future does give us clues. A huge clue might be found in comedy.

What comedy says about true understanding.

Simmons asks Apatow what he thought about the backlash to Rogen’s movie, The Interview. “It did do something important.” Apatow says. “We should remind the world that there are people suffering and being murdered. That’s the point of comedy and satire.”

Jason Zweig felt this way too, and it’s why he wrote The Devil’s Financial Dictionary. “The ability to define a term in such a way to be cynical or funny is a measure of your own skepticism,” said Zweig. If you can make a good joke about something, it’s a signal for deep understanding.

When Gary Vaynerchuk said that he had “high emotional intelligence,” it’s along the same lines. And knowing something deeply is important.

When Taylor Pearson projected what he thought jobs would look like, he noted the value of deep understanding. All the successes in Pearson’s new economic landscape, have done 2-3 things really well. Comedians have known this a long time.

Carol Leifer may be the best example of this because of her longevity. She’s found humor in things for decades. This is the future. The people who learn something well and understand human nature will succeed.

Whatever arena you’re in, you need to figure out the details. Ramit Sethi said you have to know the important numbers for your business. Jason Calacanis said that you have to know your product, your competitors, and your industry. Dan Coyle calls this the “construction” part of talent. Brett Steenbarger terms it analyze. Each of these people uses different terms, but speaks to the same idea.

If you want to be funny, you have to know the thing you’re talking about. Apatow displays this in the podcast. He talks about going to a Taylor Swift concert. He talks about his movies. He explains the process of working with Gary Shandling (which was absolutely fantastic but I didn’t know how to include it in this post. It’s at about the 31:00 mark, go listen to it.)

Thanks for reading, I’m @mikedariano on Twitter. Wow, you made it to the end of the post. A solid 1700 words. These posts take about 5 hours in all to write. If you liked it enough to say thanks, you can donate $2.

Is Bill Simmons a Superforecaster?

Bill Simmons is a great entertainer, but is Bill Simmons a superforecaster?

Serendipity struck when I listened to Bill Simmons and Joe House forecast their NBA Eastern Conference  over/under win totals podcast the same day I finished Philip Tetlock’s Superforecasting. That night, I wondered: Is Bill Simmons a good forecaster?

Simmons is a great podcaster. He knows a lot about NBA, he wrote a book about it. He talks a lot about gambling, so he may be good at that as well. These things seem to indicate that he’s a good forecaster, but is he really?

But before we answer that, I have to confess a near miss. 

I almost answered the wrong question.  Philip Tetlock, the author of Superforecasting, warns readers to be careful they don’t switch one question for another. Tetlock writes:

“Formally, it’s called attribute substitution, but I call it bait and switch: when faced with a hard question, we often surreptitiously replace it with an easy one. “Should I worry about the shadow in the long grass?” is a hard question. Without more data, it may be unanswerable. So we substitute an easier question: “Can I easily recall a lion attacking someone from the long grass?””

When I started thinking about Simmons and forecasting I nearly fell for this. I replaced, is Bill Simmons a good forecaster with is Bill Simmons an entertaining forecaster. The answer to the second question is yes. When I checked the iTunes store on 10/27/15, three of the top five podcasts were Simmons’.

What I needed was a scorecard. Something that would keep me focused on the right things and the right question. Something like this:

superforecastingcommandments1
One of my notes from the book.

Tetlock’s book concludes with 11 commandments for aspiring forecasters. These act as a snapshot of the book. It’s just a glimpse. In the same way you wouldn’t confuse a vacation brochure (do these still exists? maybe today it’s a vacation twitter account?) for an actual vacation, you shouldn’t confuse these commandments for a thorough explanation of forecasting. 

Our plan: List each of the 11 commandments and see what Simmons or House says about the idea. The bold parts will be commandments from the book, quotes will be from the podcast, and my notes are whatever is left.

One final note: The line is the number of games the odds makers in Las Vegas say a team will win. If it’s a number like, 34.5, a bettor can choose the over (35 and above) or the under (34 wins and below).

Ready?

1 – Triage, focus on where your work will pay off. Simmons and House both name certain bets as “locks.” The guys recognize that betting on all the NBA teams is a lot harder than betting on some of them. Some of the Vegas win totals are very close to their initial guesses, while others are much farther away. Some are more enticing than others. 

When Jason Zweig added comments to The Intelligent Investor, both Zweig and Graham were quick to point out that a good company may not be a good investment. The best investments were in companies that returned the most value to their shareholders. It’s an important nuance.

House and Simmons look for this in the NBA. One example is the Atlanta Hawks, who Simmons thinks will be not-quite-as-good as last year. The Hawks might have overachieved, and them being a bit worse (mean reversion, see this Nick Murray post for more ) makes sense. That’s an easier case than figuring out if the Knicks will be better with many new players.

2 – Break intractable problems into tractable sub-problems. It’s hard to figure out if the Cleveland Cavaliers will win more than 57 of the 82 games they play. There are a lot of variables that in that problem. To make it easier, Simmons and House create a sub-problem that’s easier to figure out — will Lebron James (the best player on the team) play a lot?

Current thinking in the NBA is to not push the best players during the regular season so they will be healthy for the playoffs. Simmons and House guess the Cavaliers will do just that. Will Lebron play all 82 games? Certainly not.

Last year he played 69 games and the team won 50 of them. Now he’s a year older, has a greater chance of injury, and maybe he’s not as good as last year. But, this doesn’t answer our question. We need to avoid the bait and switch I almost fell for.

Once you break hard problems into solvable pieces, you need to put everything back together again. A smart bettor will sum the solvable sub-problems to get a cumulative answer to the intractable one.

3 – Strike the right balance between inside and outside views. Simmons is both a “Boston homer” and, well-connected analyst. House is a fan. This episode features mostly an outside view of the league.

This can be good. There are lots of cases where a team believes they will be good, but they aren’t. Teams and fans that think “this is our year,” fall into an outside view trap. Aside from when they talk about their favorite teams (Boston and Washington), House and Simmons have an impartial view on the league.  

On the other hand there’s the inside view. Inside views are ones with the most specific information, but it’s often not enough. When the Titanic shipped off, there weren’t enough lifeboats for everyone on board. The inside view (from the shipmaker) was that the ship was unsinkable, therefore they didn’t need that many boats. The outside view would have been to ask a third class passenger what they thought about not having access to a lifeboat.

The best way to forecast sports is also an illegal way. Pete Rose is banned from baseball because he used the inside view. The key is to find balance, like when buying a house. You literally should go into the house for the inside view, but also look at the school district, previous sales, etc. for an outside perspective. 

We don’t want to be the hammer that sees everything as a nail. Instead, we should use multiple views like we would multiple tools.

4 – Strike the right balance between overreacting and underreacting to evidence. A lot of the talk on the podcast is about players on new teams. For good reason. Steve Kerr is credited as the needed upgrade for the Golden State Warriors to win the title last season. Lebron won once he teamed up with Dwyane Wade. The challenge for a forecaster is to find the Goldilocks zone of information, what’s just right?

Tetlock might suggest we pay attention and not answer the wrong question. Let’s use the Boston Celtics as our example. Simmons is a huge Boston fan, as you can gather from his positivity on the team:

 “They were 20-10 last year, they were an above .500 team once they got Isiah Thomas, their biggest issue was they had bad big guys and they brought in David Lee and Amir Johnson. They’ll be better defensively. They have a lot of depth… I think Marcus Smart is going to be a lot better this year…they’re built for a 47-48 win type of season.”

Okay, a lot of new evidence. The key to superforecasting is to separate how much of this matters and how much doesn’t. Simmons weaves numerate – “they were an above .500 team” – and literate – “they have a lot of depth” – examples into his case. How do you figure out what matters?

The best forecasters, Tetlock found in his research, are ones who start with a good forecast and  make small changes. It’s like a chef who switches oil for butter in a recipe, not a chef who makes lasagna without noodles.

A good starting point (see this Michael Mauboussin post for more on base rates)  is to ask how many games the Celtics won last year (40). The over-under for this year is 43 ½.

Now, is the evidence clear enough that the team will win four more games? Simmons thinks so.

5 – Look for clashing causal forces at work. “Synthesis is an art,” Tetlock writes, “that requires reconciling irreducibly subjective judgments.” Huh? Let’s explain it in basketball terms

When Simmons and House talk about the NBA Eastern Conference, they pause at a few spots to get their bearings.

Simmons points out that not all the teams can go over the win totals. They can all improve, but they can’t all win more games. It’s the same thing if everyone became a better driver, some people would still be below average. 

When talking about the Toronto Raptors, the guys are somewhat at odds. House is confident that they’ll win more than the projected number, Simmons less so. He invokes this bit of thinking:

“It feels weird to go under, because then you have to point to at least two other teams in this division that are going to win more than you think. We know one of them, but then you’re basically saying the Knicks are going to win 40 games and I don’t feel good about saying that.”

Simmons recognizes the Raptors can’t be worse in number of games won and other teams in their division not be better. And this is key: remember what question you are answering. This podcast is not about whether teams will be better, it’s about the number of games they win. There are only 16 divisional games in the NBA. If the other divisional teams aren’t going to be better, then the chances that Toronto will win most of the 16 divisional games is high.

6- Strive to distinguish some degrees of doubt. Tetlock found  that people who refined their guesses were often the most accurate. Superforecaters avoided, “granularity as bafflegab,” Tetlock writes.

House and Simmons do this too. When they make their NBA guesses, many were to very specific numbers. The Sixers “feel like an 18-62 team,” and Chicago “feels like 46-36 to me,” says Simmons.

This is a signal that Simmons and House think at the right level. It’s detailed enough. In his research, Tetlock noticed that forecasters who guessed to the nearest 10th of percent were less accurate than those who guessed to the nearest 5th who were less accurate than those who guessed to the nearest 1 percent.

7 – Balance under and over confidence, prudence and decisiveness. Confident arrogance and decision paralysis is a balance beam that all decision makers walk. Tetlock warns not be drawn to confidence and decisiveness just because that’s what people want. There are no absolute to-dos, but there’s one do-not-do; develop hubris. A parable will help.

There once was a hedge fund that made a lot of money – and that’s in hedge fund terms. The hedge fund was full of brilliant people. Some would later win a Nobel prize. Others were less accomplished, but only barely. 

In basketball terms it was like 8 of the best 20 players got together and formed their own team. Both teams, our real hedge fund and hypothetical basketballers, were better than everyone else. By a lot. Outsiders wanted in. Investors begged to have the fund manage more of their money. Executives, trainers, and ticket sellers begged to help the players.

But as the teams succeeded, their confidence grew. Their decisiveness bloated. Their prudence shrunk. We can do this on our own, both teams thought. So, the hedge fund managers fired their clients, “we have enough of our own money,” they told the investors, “we don’t need you anymore.” The basketball players did the same. They got rid of the trainers, medical staff, ticket sellers. When you’re so dominant, do you really need help from others? 

Yes, it turns out that you do. The hedge fund, Long Term Capital Management, hit a dry spell. In 1998 they needed 2B$ to weather a momentary liquidity snafu. No one threw them a lifeline. Only once the company was dead in the water did someone pull the body out. Ironically, the amount they needed was almost exactly the amount they told to leave the fund.

Our hypothetical basketball team suffered too. Two players collided in practice. One had an emotional breakdown. One was mad he didn’t play enough and he sulked on the bench. With barely enough players, the team wore down. There were no trainers to help them get better, no ticket sellers to dream up crazy promotions, no COO to manage the team.

It would be the norm for Simmons and House to wave their hands and shout. They would boldly declare why they were correct. They don’t.

8 – Look for errors behind your mistakes, check for hindsight bias. Our ability to look back and remember things accurately is wonderful. Wonderfully wrong. We weren’t really that wrong. It takes a lot of effort to look back and remember how you really felt at the time. 

The book has some wonderful stories from Tetlock’s history that I really enjoyed. We won’t rehash those here (buy the book if you want to read those). We need action. What can we do to avoid hindsight bias?

A decision journal is one way. Write down how and why you concluded one thing rather than another. However you do it, you need to note it. Tetlock quotes Bill Gates:

“I have been struck by how important measurement is to improving the human condition,” Bill Gates wrote. “You can achieve incredible progress if you set a clear goal and find a measure that will drive progress toward that goal…. This may seem basic, but it is amazing how often it is not done and how hard it is to get right.”

Simmons does not do this. “Last year we did okay,” Simmons says, “the year before we did amazing.” That’s not good evidence. Evidence is key because we want to gauge results against process.

Mark Cuban noted that the Dallas Mavericks do this. Adam Carolla does this for his projects. Tyler Cowen works this way.

9 – Bring out the best in others, let others bring out the best in you. The conversation between House and Simmons is a case for bringing out the best in others and letting others bring out the best in you. It works between House and Simmons because they are friends and know the rules of the game – have fun.

People can be even better forecasters if they work well with others, but this isn’t easy or immediate. Tetlock writes that after some people were placed on teams, they kind of clammed up. Some noticed the credentials of the people around them and thought, maybe I shouldn’t say anything.

In those groups, the superforecasters said there was a lot of dancing around and couching statements so not to step on someone else’s toes. The best situations had accepted leaders and norms. If you know who’s in charge and what to do, you’ll do better work.

Simmons and House are old friends, and the balance is clear. Simmons is the host, House the guest. Done.

10 – Learn by doing. There’s only so much you can learn by reading about forecasting, writes Tetlock.

“Just as you can’t learn to ride a bicycle by reading a physics textbook, you can’t become a superforecaster by reading training manuals. Learning requires doing, with good feedback that leaves no ambiguity about whether you are succeeding—“ I’m rolling along smoothly!”— or whether you are failing—“ crash!” “

Betting is a great way to learn by doing because the results are clean and immediate. Once the NBA season is over, there will be no doubt about whether some bets were right or wrong. The real world though is much more ambiguous.

11 – Be willing to break any of these commandments. One key point in Superforecasting is that forecasting is never done. “It ain’t over till it’s over,” quipped Yogi Berra. It’s good advice for forecasting too. The most successful forecasters were ones that constantly evolved.

For example, sometimes superforecasters found an inside view that was so complete it correctly guided them to the right answer.

When Simmons and House talk about the NBA, they do just this. There’s no reason to “strike the right balance between overreacting and underreacting to new information” if there’s no balance at stake. If a great player hurts his ankle, the bet changes, and not evenly.

Is Bill Simmons a good forecaster? It appears so. Simmons marches to the same rhythm of Tetlock’s research.

Wow, you made it to the end of the post. A solid 2500 words. That’s like 10 pages in a book (and forever online). If you found a few things valuable, you can donate $2.

Jason Zweig II

Jason Zweig (@JasonZweigWSJ) joined Shane Parrish (@FarnamStreet) to talk about his new book, The Devil’s Financial Dictionary. Much like Zweig’s conversation with Barry Ritholtz, this is much more than a book release publicity stop – though even the parts about the book are quite good.

What we’ll cover: a day in the life of Jason Zweig, the current state of journalism, how to write a book, 2 things the average investor should do, if Zweig were king for a day, and Macklemore.  

A day in the life of Jason Zweig.

Zweig says that his typical day is “kind of a mess.” If he’s lucky, he’ll arrive at work before seven and head to the gym. It’s a chance to “clear my head,” Zweig says. Scott Adams said the same thing about his morning routine when he talked to Tim Ferriss. Adams says that he reads the news while his coffee brews. Once he’s consumed enough, he tries to mentally flush and start fresh. Zweig too.

Zweig says that his job is to write the same thing over and over again without his editors or readers realizing it. “It’s harder and more challenging than it sounds,” Zweig says, “but it’s also more fun.” Work should be like this. Tyler Cowen noted that ambition could be as desirable as happiness. Seth Rogen and Evan Goldberg said that even their job has obstacles. Tim O’Reilly noted the importance of work. We like to solve problems. For Zweig that means figuring out what to write.

His model is to triangulate a story between financial markets, current events, and readers’ lives. Zweig will often pull ideas from areas beyond finance or business he says. He devotes the hours after work to non-business books. Something has to be really good, for him to read an industry book at night, Zweig says. Like Michael Mauboussin, he prefers physical books.

This exchange reminded me of the Richard Feynman story about desserts. Feynman began his career in the Northeast, suffering through the winters. One day he decided to get out, and an offer came from sunny California. But, soon after Feynman there was a day with awful smog.  “This is absolutely insane,” Feynman writes. Winters weren’t worse than this. He decides to go back. Then changes his mind again.

Tired of flip flopping, Feynman comes up with this solution.

“When you’re young, you have all these things to worry about – should you go there, what about your mother. And you worry, and try to decide, but then something else comes up. It’s much easier to just plain decide. Never mind – nothing is going to change your mind. I did that once when I was a student at MIT. I got sick and tired of having to decide what kind of dessert I was going to have at the restaurant, so I decided it would always be chocolate ice cream, and never worried about it again – I had the solution to that problem.”

Zweig has done this with what he reads, but it’s true for any area he notes. We can all make decisions ahead of time, that make our lives easier. “I think you can put policies and procedures into place,” says Zweig, “that can help you make rational decisions.” In fact, it’s just what the doctors ordered.

In Mean Genes, the authors write that there are two ways to counter immediate cravings; substitutions and preemption. Ride roller coasters instead of motorcycles and don’t walk past the tavern if you crave alcohol. For finance, you can play poker with your friends rather than the stock market or for entertainment you can read fiction instead of watching television.  Tadas Viskanta and James Osborne talked about how to do it with babies and investments.

The key is to decide ahead of time. “Structure your life so the things that tempt you into bad behavior don’t get surfaced in your stimuli,” says Zweig.

If his day is spent working on books, WSJ articles, tweets, and avoiding biases, Zweig’s nights are for broadening his horizons. He tries to read non-business and finance books.

This mix of working out, working hard, and working his way up has created a soup of success. One other ingredient, Zweig is quick to add, is luck. He says his career is built on it. His first job was working for a magazine about Africa, and from there he went to Time, and Forbes. “It was all serendipity,” Zweig says, “like everything in my career, if you took away the luck  there’s no plan. There might be nothing left.”

While we should be quick to credit luck, we shouldn’t over emphasize it. Zweig’s career is actually well put together. Malcolm Gladwell advised people to just write a lot. Zweig did that. Stephen King wrote that all writers must write and read a lot. Zweig did that. Tom Rath said that his research said that some people align their careers with a natural talent. Zweig may have done that. Robert Green said that maybe you don’t need 10,000 explicit hours to be great. Maybe small, not immediately relevant experiences add up too. Zweig did that when he wrote about Africa.

Whatever the path was, it’s led to a good day for Jason Zweig.

The current state of journalism.

When he spoke with Ritholtz , Zweig shared thoughts about the negative changes to journalism. We won’t cover that again, but Parrish asks an insightful follow-up question, “what is a reader to do?”

This, we can work with. Take the site you’re reading now. My site. It doesn’t have the same oomph of the Wall Street Journal or Farnam Street. Strike one.

Strike two is that we know people actively manipulate the news. Parrish mentions the Ryan Holiday book, Trust Me I’m Lying. Holiday wrote the book to show how companies could newsjack situations for additional coverage.

Strike three is the volume of work available. There’s more to read than we have time for reading. Seth Godin writes about this in regards to podcast: “As of now, there are more minutes produced by the podcasts I listen to each day than there is time to listen to them. I can’t listen to something new without not listening to something else. Which makes it challenging to find the energy to seek out new ones.”

I added the emphasis because Godin notes the two types of energy required; finding and consuming. If you spend too much on the former, you’ll have none for the latter.

Back to Parrish’s questions then, “what’s a reader to do?” Zweig suggests three things.

One, approach something with a doubtful until proven philosophy. “If you’re not a skeptical reader,” Zweig says, “you’re not really reading.” That doesn’t mean we have to do it all the time. I trust Zweig, Parrish, and other writers. When you find someone that leads you astray, you need to decide what to do. Naval Ravikant said that when he finds a discrepancy, he is immediately done.

Two, steer the world to journalism you want. Judge a site by the quality of links it uses. Then if you find something good, support it financially.  Donate to Parrish, or the wonderful Radiotopia studios.

Three, connect with history. Zweig says that he tries to write with “points of contact,” with history. We often discount the past and believe we know more. In some ways we do, but in other ways we don’t. Stoicism, says Naval Ravikant, has become popular in Silicon Valley. If it was true two-thousand years ago, and it’s true today, it’s probably true forever. Zweig’s new book, touches on this as well.  

How to write a book.

Zweig says that The Devil’s Financial Dictionary came from a series of events. First, he redesigned his website. Then, he needed to add new content to the site and he started coming up with these terms. Zweig was inspired by Ambrose Bierce’s (“one of my favorite writers,” he says) The Devil’s Dictionary.

It was an adventure, says Zweig. First he wanted to see if he could come up with words and definitions less than 150 words. Then 100 words. Then 50. Then even a single word. He did it!

One a larger scale, Zweig wanted to test himself. “The ability to define a term in such a way to be cynical or funny is a measure of your own skepticism.”

“Until you can do this,” says Zweig, “you don’t understand the weaknesses in what the person is telling you.” You are biased to ideas, one way or the other, figure out what you don’t know to get the full picture. Maybe it’ll even turn into a book.

Two things for the average investor to do? (or not do)

There are two questions the average investor should ask; should I do nothing and if I do act, what do I do? Learning from people smarter than us can help us answer these questions.

Should I do nothing? Yes. “Any recommendation to take action,” says Zweig, “has to be compelling enough to overcome the inherent intrinsic advantage of just sitting there.” Like in the board game, Risk, the advantage goes to the non-mover. Barry Ritholtz quips in his podcast, “don’t just do something, sit there.”

In his book, Getting Smarter, Seymour Schultz explains his “decision maker.” Take the status quo, and weigh all the components. If it’s buying a house, weigh the values of good schools, number of baths, proximity to work, and so on. Then, do the same for the option under consideration. Is the new house in a better school district? If so, it gets more points. Schultz said he only took the option for action if its total was twice that of staying the course.

Sometimes the best choice, is to do nothing. Other times we should act.

If I do act, what should I do? My daughter just started reading “choose your own adventure books” (fun fact: Tim Ferriss was a beta reader for them as a kid) Let’s use this as an analogy for our decisions in life. Much like the hero of a book will face the choice of entering the cave without a flashlight, or searching for one on the hillside – we too must make choices.

If it’s familiar, go with your gut.

If you’ve entered dark caves before, and your gut says this looks okay, then go ahead. Intuition is maximized with experience. In the book, Superforecasting, Magnus Carlsen is quoted:

“If I study a position for an hour then I am usually going in loops and I’m probably not going to come up with something useful. I usually know what I’m going to do after 10 seconds; the rest is double-checking.”

It’s the last part we should note! “The rest is double-checking.” It’s figuring out if you’ve overlooked something (maybe a bias) and then making sure your initial choice still fits.

Gary Vaynerchuk said that he looks for investments with his gut (intuition). Before he invested in Twitter, he recalls saying to himself, “wait a minute, I’ve seen this before.” If it’s familiar, go with your gut.

If it’s unfamiliar, proceed with thought.

First you check what the base rate it. Then you check the base rate. No really, check the base rate. This isn’t like going the dentist and her saying you should floss, and you thinking yeah.  This is liking going to the dentist and her saying you need to floss or die because you’re getting oral cancer. Check the base rate, it could save your life.

The problem with base rates is that they aren’t very much fun.

Will Uber go public? How much will Square be worth? Is Twitter in trouble? Those questions are fun. But, they also don’t really matter. Jeremy Siegel said that IPO returns are not any better than small cap funds. That’s a base rate that says “stay away unless speculating.”  Plus, IPOs are floated when the market is up. Buying an IPO is like buying a ski jacket at the ski lodge, it’s fun to pick out, but it’s not going to be cheap.

Base rates can even be found outside of investments. Ramit Sethi demanded you do this for business too. What are click rates? What are open rates? What is your conversion? These are all base rates to figure out.

After you figure out the base rate, ask why you are different. “Ask, what do I know that the other side doesn’t know, and why do I think I know more than they do?” says Zweig. Both of these need to be a strong answers if the base rate significantly moves toward the number you came up with. If there’s not a good reason, the base rate is the number you use.

In the choose your own adventure books I always entered the cave without a light and I always fell down a hole. But, going back in time is only a few pages away. In life, it’s impossible.

More important than the right answers is that you ask these questions. Zweig says, “temperament is the most important trait for success.” He notes that when Benjamin Graham wrote, The Intelligent Investor, he used the term enterprising as the term for who could benefit. There’s a reason. You don’t have to be smart, gifted, or brilliant. You just need a certain attitude of inquisition, humility, and thoughtfulness.

King for a day.

Parrish asks Zweig what he would do if he were king of the financial markets. His answer was brilliant. Rather than regulate, Zweig would nudge.

Nudging is wonderful. Richard Thaler wrote about nudging was born in Misbehaving and how it was applied in Nudge.

An example of a nudge is how Sanjay Bakshi begins to solve a question. He starts with, “part of the reason is this,” rather than “this is the reason.” In anything we do, there is a starting place. If we can tweak the place we start (a nudge), we can make better choices. When Bakshi says to start with “part of the reason,” that’s a nudge.

Zweig isn’t speaking about decision making, but retirement. In one study, participants were switched from needing to enroll in a retirement plan to automatic enrollment. The participation rate rose from 65% to 98% with almost no change in the dropout rate.

The one other thing Zweig would do, this one much bigger, is to reinforce the belief in a just world. From Wikipedia:

“The just-world hypothesis or just-world fallacy is the cognitive bias (or assumption) that a person’s actions are inherently inclined to bring morally fair and fitting consequences to that person, to the end of all noble actions being eventually rewarded and all evil actions eventually punished. In other words, the just-world hypothesis is the tendency to attribute consequences to—or expect consequences as the result of—a universal force that restores moral balance. This belief generally implies that in the existence of cosmic justice, destiny,divine providence, desert, stability, or order, and has high potential to result in fallacy, especially when used to rationalize people’s misfortune on the grounds that they “deserve” it.”

This was more philosophical than I expected Zweig to get, but I liked it. The point comes up after Zweig mentions this WSJ article about a million dollar parking spot.

Zweig’s concern is that we stop feeling this way, and he tells a lovely story from Where are the Customer’s Yachts. (You’ll need to listen to the podcast to get that part).

“You don’t need an Uber, you don’t need a cab, forget a bus pass, you got a moped man.”

Wait, were those Macklemore lyrics in a blog post about a Wall Street Journal reporter? Yes, yes they were. We’ll get to that connection in a moment.

Late in their conversation, Zweig and Parrish talk about private sector valuations. On the one hand, Zweig notes, it takes risky investments away from the public and into private hands. If tomorrow’s equivalent of Webvan.com blows up, the damage will be to people who knew that was an option (and fits within the just world philosophy). On the other hand, it feels bubbly. “It’s hard for outsiders to have a transparent view of what’s going on,” Zweig says. Here, he touches on our idea of layers.

The Phil Rosenthal post has the full idea of layers (see the “Idiots and Honesty” section). Briefly defined, the more layers between the current state and the ideal state, the worse something is. Private companies like Uber have lots of layers. They don’t share their finances. They have marketers who might be “newsjacking.” They have investors who might be charlatans. They have a new aura. They are over represented in the news. From Google Trends (October 2014).

Each thing is a layer that disguises the true thing. But this isn’t necessarily bad. Macklemore’s song Downtown (which the quote above is from) has many layers.

Tribute, mockery, history, a good beat, and so on. Just like Uber, this song is one thing as we see it and another thing if we examine it. The difference arrives here. We know what the parts of the song are, and that they are benign. We don’t know anything about Uber.

Thanks for reading, Thanks for reading, I’m @mikedariano on Twitter.

One part I didn’t get into with regards to intuition, is that situations should be familiar and stable. Football is a good example. It’s stable in the sense that the rules are the same, the players act in similar ways based on their positions, the plays that have been run are consistent. Contrast this with being a writer. That career is much less stable, and writers would be best served by relying less on their intuition. For more on this, read Kahneman’s Thinking Fast and Slow.

Dan Coyle

Dan Coyle (@DanielCoyle) joined Brian Johnson (@_Brian_Johnson) on the Optimize podcast to talk about talent. Coyle is the author of The Little Book of Talent and The Talent Code. In this episode the pair breaks down the different ways to grow talent (note, talent is grown, not genetic). As always, the entire interview is good, here is our table of contents.

  •  Community.
  •  Biology of it.
  •  Deep practice (with a bear).
  •  Lunchpail mentality.
  •  How Dan Coyle did it.
  •  Practical tips.

Community.

Coyle’s book, The Talent Code begins with a question, “How does a penniless Russian tennis club with one indoor court create more top-twenty women players than the entire United States?” That, is a good question.

Coyle went on to investigate what that club did that others didn’t. The details are many (some of which we’ll get into below) but one was the community.

These “talent hotbeds” aren’t atypical. Austin Kleon writes this in his book, Show Your Work:

“There’s a healthier way of thinking about creativity that the musician Brian Eno refers to as “scenius.” Under this model, great ideas are often birthed by a group of creative individuals—artists, curators, thinkers, theorists, and other tastemakers—who make up an “ecology of talent.” If you look back closely at history, many of the people who we think of as lone geniuses were actually part of “a whole scene of people who were supporting each other, looking at each other’s work, copying from each other, stealing ideas, and contributing ideas.” Scenius doesn’t take away from the achievements of those great individuals; it just acknowledges that good work isn’t created in a vacuum, and that creativity is always, in some sense, a collaboration, the result of a mind connected to other minds.”

Coyle’s theory is that people need to at least see what’s possible. He mentions the fall of the four minute mile. That is, once Roger Bannister ran a mile in less than four minutes, other people did it too. I’ve heard that story too, but there’s more to it than just that.

You see, mile times had been decreasing for a long time. It wasn’t that people suddenly realized they could be faster, they knew that.

 

What accelerated the change was that more people actually saw faster running. In the 1930’s and 40’s, videos of runners were shown in theaters and schools. Video’s like this one.

Coyle suggests that communities show other people what is possible. At the Russian tennis club, only 1 person succeeded. In the next cohort, 4 made it big time. Then 6. When tennis players in Russia saw one of their own succeed, they began to do it at a faster rate as well. Coyle calls this “filling your windshield.” It’s keeping the people you want to be like, in your view.

Malcolm Gladwell wrote about this vis-a-vis Jamaican sprinters.

“So why are the Jamaicans so good? There are many reasons, but the simplest is that the effect of peers on high performance are REALLY strong. In Jamaica, EVERYONE sprints. There are 20 heats in the 100-meter regional championships. And because everyone sprints, and the average quality of sprinting is so high, everyone’s expectations are raised accordingly. The psychological ceiling on elite performance if you are a high school sprinter in Kingston is, like, a foot higher than if you are a high school sprinter in America.”

Simon Rich said he wants to be around people smarter than him and feel like he’s barely keeping up. Tim Ferriss volunteered so that he could be around people smarter and more connected.

If you want to get better at something, you should probably be around people who will push you to be better – in Russia or anywhere else.

How this talent thing works, biologically speaking.

Talent, says Coyle, is the ability to do something.

Jump ahead to the 1:00 mark of this video. The question being answered is, “why do speeds increase for myelinated axon?”

Coyle describes myelin as “insulation around a wire that prevents the signal from leaking out.” Certain forms of practice build up myelin. More myelin, faster signal. Faster signal, better performance. For Coyle, this was demonstrated when he saw Tiger Woods do this – and Coyle wanted to too.

And he did it! After a few intense minutes a day for eight months I was able to finally do it,” Coyle says. To build these myelin superhighways, you have to practice the right way, and that means deeply.

Deep practice.

Okay, knowing the biology is good, but how do we actually get better at something? The key, is deep practice.

Coyle begins by noting that we should figure out what practice is. We say eat and that can mean a lot of different things. So too for practice.

The type of practice Coyle courages has a certain look.  “I’ve noticed that people in the sweet spot,” Coyle says, “have a facial expression that looks like Clint Eastwood.” But besides this guy, what should practice look like? Before we get into it, let’s apply a tool we learned form Joshua Foer. Foer noted (and wrote about) how we remember things. If we can attach a wild image to something, we’ll have a better chance of remembering it. Foer explains:

“The secret to success in the names-and-faces event—and to remembering people’s names in the real world—is simply to turn Bakers into bakers—or Foers into fours. Or Reagans into ray guns. It’s a simple trick, but highly effective.”

When he talks with James Altucher, Foer says that he images Altucher as “I’ll touch her” and him acting like a creep. We can do this too!

Our image for deep practice will be a bear slowly looking through a telescope. It works best if you come up with your own bear, but the internet – of course – has plenty of bears with telescopes.

The bear.

If you succeed more than 80% of the time, says Coyle, the task at hand is too easy. If you succeed less than 50% of the time, it’s too difficult. Like the story of Goldilocks and the three bears, there is a “just right” range of practice.

deeppracticespectrum

Steven Kotler said that we can think about improving in small steps. You don’t need to try something twice as hard, instead aim for a 4% improvement. Coyle compares it to a hockey player or figure skater who occasionally falls down. That’s the zone we want to be in.

Go slow.

Coyle mentions implicitly that deep practice is often slow practice. In one instance he talks about Claire learning the clarinet. She moves her fingers so slowly that she feels her mistakes Coyle explains. Later he references this video of Lebron James and Hakeem Olajuwon. This is the most boring video of two of the greatest basketball players ever made.

And for good reason! You have to move slowly to learn new movements.

It make sense that Steve Martin, our grandfather for deep practice, said that he would play a banjo record at a slower speed than normal so he could pick along.

Examine closely, and then widely.

Look at the basketball video again. First Lebron learns where to catch the ball (high/low, near/away from his core). Then where to step. Then dribble. Eventually he puts those sequences together. Then he does it with someone guarding him. People build talent the same way kids build Lego castles – one piece at a time.

Coyle uses the analogy of construction zone and arena zone work. In the construction phase you spend time building, in the arena zone you put it all together. Each of these parts, Coyle says, are important to get things right.

Brett Steenbarger suggested this same – zoomed in, zoomed out – approach to creativity. Steenbarger uses the terms analyze and synthesize. First you dive deep into an idea, then put together what you find. Our bear looks through the telescope at a single star, then lowers it to look at the a constellation.  

We can also think about the practice of practice. “These guys all approach learning as a craft, as a pattern, as a system,” Coyle says. That means that getting better at practice is important too. Something else that Coyle has noted as important; a lunchpail mentality.

Lunchpail mentality.

Coyle retweeted this:

Successful people work really hard, Coyle says. He quotes, Michelangelo, “If you knew how much work went into it, you would not call it genius.” It’s hard work.

Michelangelo, Coyle says, worked for stone masons early in his life. He learned how to work with a chisel before he could write. He apprenticed with artists. It was a slog.

“They’re not waiting for inspiration, that’s for the amateurs,”  Coyle says.

In Do The Work, Steven Pressfield writes:

“Stephen King has confessed that he works every day. Fourth of July, his birthday, Christmas. I love that. Particularly at this stage—what Seth Godin calls “thrashing” (a very evocative term)—momentum is everything. Keep it going. How much time can you spare each day?”

That’s not what it looks like though. There are more of highlight reels than practice sessions. But the reality is the opposite. There is a lot more practice, than there are highlights.

Carol Leifer spoke and wrote about bombing as a comedian. It happened a lot. You don’t get that when you look at her IMDB profile. It’s filled with credits for some of the greatest shows ever. That took work to get there.

Brian Koppelman said that he had to work on Solitary Man everyday. If he didn’t then it would feel to him like he wasn’t moving the project forward. Even if it was something small, he did it. (Koppelman went so far as to write on his shoes as a reminder).

How Dan Coyle did it.

Coyle is no stranger to the process. Starting out he wanted to be a sports writer, “so I would go to the games and I would come home and pretend I was on a deadline and write up the story on the game I just watched as if I worked for a paper.”

Malcolm Gladwell recently advised something similar. Gladwell said, work for a newspaper. It will force you to write (a lot!). It will force you to hit deadlines. It will develop your skills of asking question. Jason Zweig spoke about the tutelege and institutional memory at papers. Each of these things fits perfectly with the construction and arena example of how we can build skills.

Practical tips.

A lot of the talk of talent and success is abstract, but Johnson and Coyle end the interview with some practical tips.

Visualization

“The science of visualization is kind of all over the map, but anecdotally and instinctively it seems to make sense,” says Coyle. On this blog, we have a lower bar for science. We ask, “does this help me?”

Scott Adams took this approach with affirmations. If there’s something to this, Adams recalls telling himself, and I don’t use it that would be foolish. Dan Buettner and Dave Asprey thought the same thing about food.

Whatever it is, test it on yourself. If it works, you don’t need to worry about why.

Take a nap.

Sleeping is great, no one would argue that. Why though? Coyle says that professional athletes are great at sleeping. It makes sense for them, they’re up late to compete. What can you and I do?

Barbara Oakley explains in her book, A Mind for Numbers, that our brains need sleep to organize what we learned. Imagine what a store looks like after the first holiday rush or when college students return to town. It’s a mess. At night the store gets restocked, the second wave of toys is brought out, and the floors get cleaned. That’s what happens in our brains as well. Everything we learned gets put in a place.

Reframe repetitions

Our slow moving bear with a telescope needs a lot of practice. That can get boring, if you let it. Coyle says that you need to reframe repetitions. Rather than conjure up drudgery, says Coyle, take a moment to embrace the beauty in doing the same thing over and over.

Be patient while doing good work.

It takes time says Coyle. It took Stephen Dubner years to write a great book. It took Chris Hadfield years to become an astronaut. It took Gary Vaynerchuk years to create a business.

You have to know this, and at the same time do your best work. Your best work, Austin Kleon notes, will be far from the work of people you admire, and that’s okay.

Have a gardener and carpenter mentality says Coyle. Be patient like a gardener, who knows that seeds don’t sprout the next day. At the same time you should do your best work so that when the harvest comes, you have built something that will stand the test of time.

Feel stupid.

“Don’t be afraid of feeling stupid,” says Coyle, “that’s where the good stuff happens.” Feeling stupid is part of stretching, of getting out of a bed that’s too soft and into one that’s just right. But you don’t need to walk around and aim to be stupid. Naveen Jain says that he reads widely so that he can ask second level questions. If you approach an expert, Jain says, they’ll probably dismiss you if you ask something elementary. But, if you ask something a bit above that, they’ll engage with you more. You can be stupid on that level, knowing that you stretched to get there.

Thanks for reading. I’m @mikedariano on Twitter.

Wow, you made it to the end of the post. A solid 2300 words. That’s like 10 pages in a book (and forever online). If you found a few things valuable, you can donate $2.

Malcolm Gladwell

Malcolm Gladwell (@Gladwell) joined William Channer (@WilliamChanner) on the Dorm Room Tycoon podcast to talk about writing.

There were two legs for the body of this podcast about writing; how Malcolm Gladwell writes and Malcolm Gladwell’s advice for writing. I found both fascinating. I remember reading Gladwell in college and it was enlightening. Not the actual book per se, but the type of book.  Wow, I thought, why can’t we read this in school? His books are wide, clear, and bring together an interdisciplinary approach that many people advocate.

Tren Griffin spoke about interdisciplinary models for business. Sanjay Bakshi spoke about  interdisciplinary models for finance. Phil Rosenthal spoke about  interdisciplinary  models for writing. All of these accomplished people implicitly advocate for Gladwell’s books. Big ideas should be understood as multifaceted. Gladwell shines a light that makes those gems sparkle. Enough about my admiration for Gladwell. Let’s get to the notes.

How Malcolm Gladwell works.

Stumble around

“I tend to start with a puzzle,” Gladwell says, “part of my job description is to be on the lookout for stuff that fuels this exploration.” Gladwell reads books “by the truckload,” and is a fan of the Jack Reacher series.

Gladwell, like many other people featured here, reads widely. His initial phase might mimic what  Maria Popova said about search and research. In an interview with Copyblogger, Popova said:

“I just had tea with someone – a writer whose book I’d written about and who reached out and wanted to connect – and that hour-long conversation gave me a dozen ideas to think about, to learn about, and thus to write about (including two books I already ordered based on our chat). Is that “research” in the sense that one deliberately sets out to find something already of interest? No. Is it “research” in terms of the unguided curiosity that lets one discover something previously unknown and succumb to the intellectual restlessness of wanting to learn everything about it? Absolutely.”

She continued:

“And I think that’s part of our challenge today, not just semantically but also practically – we tend to conflate “research” with search, which is always driven by looking for something you already know you’re interested in; but I think the richest “research” is driven by discovery, that intersection of curiosity and serendipity that lets you expand your intellectual and creative comfort zone beyond what you already knew you were looking for.”

Gladwell says there is, “lots of stumbling. I depend on the stumbling.” What Gladwell is hoping to find is patterns of things. In David and Goliath for example, Gladwell drew in examples from; girls youth basketball, dyslexic CEO’s, and World War Two bombings. Superficially those things have nothing to do with each other. When Gladwell reads about each he dives deep and starts to see common threads under the surface.

Research however you’re comfortable.

Besides “stumbling,” how else does Gladwell work? In one word, comfortably. Gladwell, like Michael Mauboussin enjoys physical books because of the tactile and emotional memories in them. Gladwell says he can walk along his bookshelf, and “each book represents a set of ideas and observations and I know what’s around it.”

That doesn’t mean his way is the only way. Sanjay Bakshi said that digital books work better for him. His purpose (teaching) is different from Gladwell’s (writing).

Fivethirtyeight had a great podcast about the Bloomberg Terminal. It costs $2K a month, and it’s worth it for some people, but I got the impression it wasn’t worth it for everyone. So why hasn’t it been usurped? Switching costs are too high. Even though a rival system may cost less, it’ll take too long to understand. That’s how Gladwell view his process.

What makes a good idea.

Ideas need an element of excitement says Gladwell. For example, why isn’t global warming a bigger deal? “No one has found a way,” says Gladwell, “to tell that story so it seizes your imagination.” Well, one person has. Global warming, says Seth Godin should be called “atmoshphere cancer.” Godin explains, “I’m not being facetious. If the problem were called “Atmosphere cancer” or “Pollution death” the entire conversation would be framed in a different way.

There should be some sort of artistry and flamboyance in an idea Gladwell says. Scott Adams says he noticed then when writing God’s Debris and Dilbert. How do I keep the reader interested, Adams wondered. He did this by using hypnosis. Certain words can engage people in different ways Adams notes. The word “yank” is funnier than “pull” he says. Through words, Adams creates appetizing works. Gladwell orchestrates ideas. Both entertain and connect with their readers.

Editing and drafts.

“I do many, many, many drafts,” Gladwell says. A 6,000 word New Yorker article might take six months and go through seven or eight major versions. And it never comes out right at first.

legoship“I have an expectation when I’m writing,” Gladwell says, “that it’s all going to change.” It’s like Legos Gladwell says. If you have kids, you know that making a Lego pirate ship isn’t enough. It needs to be a pirate ship with laser cannons and knights on horseback. Themes and ideas interlock easily with Legos. So too does Gladwell’s writing.

He says, “I think of writing as very modular.” Pieces can be put together or taken apart, and it’s no big deal. Except it was for Richard Thaler.

When Thaler was writing Misbehaving he had a problem. Much like Daniel Tvessky (who’s own biases about writing were outlined in the Jason Zweig post), Thaler had a problem. He didn’t want to edit his book.

He knew he had to, but he also knew he would be biased about what to take out. Any piece that he worked especially hard on, whether in research or writing, would probably have a sunk cost fallacy. That is, if Thaler devoted so much time to a certain section, he might be inclined to include it because of the investment rather than the merits. But, as a wily social scientist, Thaler had an idea.

Instead of cutting those sections, he moved them to a new document. They weren’t sections that were removed, but repurposed. It’s like when a kid brings home a Christmas art project from school and their parents delicately put it in with the other decorations. It’s being displayed, but only once a year. Good editing is best when you know thyself.

Know thyself.

Gladwell says that he doesn’t feel much pressure to write. “Everyday I’m running across something worthy of exploration,” he says. It echoes what Seth Rogen and Evan Goldberg and Anne Lamott said about writer’s block. It’s not a block so much as a gap. If you are exploring and thinking in new ways – if you are developing interdisciplinary approaches and mental models –  you’ll be stumped less.

Gladwell does this, but doesn’t think he needs to churn ideas into hits at the frequency a musician might. “My only test,” says Gladwell, “is, does this strike me as being novel and cool?”

Much like Chris Sacca, Gary Vaynerchuk, and Mark Cuban think about angel investing, Gladwell focuses on what interests him. When  Brett Steenbarger said, “figure out who you are when you are at your best,” this is what he was talking about. Gladwell knows what interests him and how to write about it. That said, he’s still trying to get better.

5 steps to be a better writer.

In this interview, Gladwell sounded aspirational. Not in a worried way, but in a I want to get better before I die way. Culled from different parts, here’s Gladwell’s advice.

1. Take risks. “I’m not sure the screenplay I wrote is any good,” Gladwell says, “but I am sure writing a screenplay made me a better writer.” Brian Koppelman said that he writes music for the same reason. Not because it’s good, but because it draws on something that makes him a better writer in other areas.

2. Make an existing skill better. Gladwell said that a few years ago he started taking narrative more seriously. He stopped what he was doing, and focused on improving one part of it. Astor and Danielle Teller did this when they wrote a book on marriage. They wanted one part of their life (marriage) to be better, so they deconstructed it.

3. Imitate. “I became very interested in the writing of Michael Lewis,” Gladwell says, “I would like to try his way and see what happens.” Gladwell’s capturing on the idea of imitation. He wants to write more like Lewis and see what happens. Jason Calacanis told Tim O’Reilly that he imitated everything he did to get started.

4. Work for a newspaper, but don’t stagnate. What? A dying form? Gladwell says that there is value in writing for a newspaper. It taught him to write quickly, to remove his ego, and to write a certain volume. “It used to take me ages to write,” says Gladwell, “then I worked at a newspaper for ten years and I was cured of that.” Gladwell practiced. Joshua Foer dove deep into practice, and deconstructed the crucial parts. But practice can’t stagnate, you need to move on. On Grantland Gladwell wrote:

“So why are the Jamaicans so good? There are many reasons, but the simplest is that the effect of peers on high performance are REALLY strong. In Jamaica, EVERYONE sprints. There are 20 heats in the 100-meter regional championships. And because everyone sprints, and the average quality of sprinting is so high, everyone’s expectations are raised accordingly. The psychological ceiling on elite performance if you are a high school sprinter in Kingston is, like, a foot higher than if you are a high school sprinter in America.”

Build your skills in a good place, but then move on to be around people who will make you better. Simon Rich said he wants to feel like he’s barely keeping up. Only then will he feel like the challenge level is right.

5. Learn to ask questions. Interviewing famous people can be hard. Gladwell said that when he interviewed Magnus Carlsen, he had to find the story. Even though Carlsen is the greatest chess player alive, the story still had to be chased down. “Know the first thing you want to know,” Gladwell says, but leave room for a conversation to flow.

Stephen King compared writing to digging up a fossil. King and Gladwell write at opposite ends of the spectrum of truth, but this part seems the same. King writes:

“Stories are relics, part of an undiscovered pre-existing world. The writer’s job is to use the tools in his or her toolbox to get as much of each one out of the ground intact as possible. Sometimes the fossil you uncover is small; a seashell. Sometimes it’s enormous, a Tyrannosaurus Rex with all those gigantic ribs and grinning teeth.”

Gladwell’s question suggestions is a method of of sweeping the fossil.

Thanks for reading, I’m @mikedariano on Twitter.