I Did 200 Podcasts With My Heroes. This is What I Learned…

podcasts with my heroes

I didn’t even want to do a podcast. Too much work!

And I’m too shy to ask guests to come on.

And I get so nervous I hope each podcast will get cancelled. Or a natural disaster will happen.

But I wanted an excuse to ask people how they made their lives better. Maybe I could do it also.

I would read a book and think to myself: I wish I could ask Judy Blume / Peter Thiel / Coolio / Tim Ferriss / Jewel / Mark Cuban / etc MORE about what they just said.

But if I just called them, would they return the call?

Definitely not. I needed a front. A lame excuse. I’d pick up the phone… “I have a podcast.

It’s been three years and now 200 interviews later. I’ve had close to 50 million downloads overall. More when I include other podcasts I’ve been involved in.

The podcast has saved my life. I’ve spoken to so many of my heroes. People who I would never have expected to have a conversation with.

Having Judy Blume, my favorite author as a child, give me relationship advice – might be the highlight of my life.

Or Brian Grazer, producer of many of my favorite movies and TV shows, give me advice about creativity.

Talking to Wayne Dyer, Coolio, Steven Pressfield, Seth Godin, Tim Ferriss, Judy Blume, Cheryl Strayed, Amanda Palmer, and on and on, has taught me so much about the world.

I hope I remember them. I hope I live what I learned. I try to.


I could sit here and write 200 things: one from each podcast. But I will write the things that stood out most for me.

You can’t change 200 things in your life. But you can file a few things away and pull them out as necessary.

I learned about creativity, nutrition, persistence, peak performance, happiness.

– Vision.

Have a philosophy of life. Are you a good, honest person. Make sure all of your actions align with that.

Do you want to be creative? Do you want to help people? Why.

Once you have a vision, every day will move you a little more forwards to achieving it.

Coolio wrote lyrics every day for 17 years before his first major hit.

Cheryl Strayed wrote for years before having a bestselling book. She knew the important thing was writing every day.

Terry George wanted to communicate the horrors of war through the medium of movies. So he made “Hotel Rwanda”.

Michael Singer gave up everything and “Surrendered”. And that was the first step towards making a billion dollar company.

Jewel turned down a million dollar offer when she was homeless because she had a vision for the direction her music would take her.

– Nutrition.

I’ve talked to people about the benefits of “meat”, “no meat”, “vegetarian”, “vegan”, “fats”, “no fats”, “fruits”, “fruits are sugar”, and on and on.

No one diet works.

Here’s what I’ve learned after talking to many people who have made nutrition a priority in their lives.

a. Good nutrition leads to higher quality of life and longer life.

b. Processed sugars are bad.

c. Eat as many vegetables as you want whenever you want.

d. Sleep eight hours.

e. Have friends.

It’s basically that simple.

– Plus, minus, equal.

I’ve heard this in various forms from many guests.

All of these guests have reached some sort of peak performance in their lives. I wanted to learn how. How do I start from nothing and learn something new?

Plus – find someone to teach you

Equal – find people to challenge you.

Minus – find people you can teach, to solidify the learning.

And, by the way, this term specifically came from a podcast I did with Ryan Holiday who interviewed MMA instructor Frank Shamrock about the concept of plus, minus, equal.

Basically all 200 of my guests went from being no good and no talent to being the best in the world at something.

– No Excuses.

When I see what these people went through I can say there is simply “NO EXCUSES”. Each one of the people had many excuses:

a. They had to support family.

b. They were scared to leave their safe jobs.

c. They didn’t have the right education.

d. They failed the first 5-50 times they tried to succeed.

e. They switched paths repeatedly and always had to start from scratch.

f. They didn’t have the money they thought they needed to start.

g. It would take too long to get good.

h. People hated them at first.

Excuses are the bricks that build the walls of your comfort zone. It’s easy to bounce off an excuse and say, “Ok, I’ll stay in the comfort zone.”

You have to smash through the bricks to get bigger than the life you could have dreamed of.

– Learning.

I spend a lot of my time trying to understand how these people learn to be the best.

Anders Ericsson, the developer of the “10,000 hour rule” which states that people , on average, need 10,000 hours to be in the best in the world at something reminded me that the 10,000 hours has to be with “deliberate practice.”

Robert Greene, another guest, discusses this in “Mastery.” Josh Foer, former US Memory Champion and another guest, discusses this in “Moonwalking with Einstein.”

Deliberate practice is:

– Find a mentor.

– DO a lot of what you want to get better at (e.g. make a lot of golf swings)

– Get feedback as quickly as possible.

Repeat the above as much as possible.

Ryan Holiday spoke about the Plus. Minus, Equal

Tony Robbins told me about “moving the target closer.” He has to teach a group of marines how to shoot better. He had never taught a class about shooting guns.

He brought the target really close. They all shot bullseyes. Then he moved it further away. Then later…further away.

His class scored the best in Marines history.

For whatever you want to learn, take it in small steps. Bring the target closer. Work with a mentor. Repeat a lot. Get feedback. Combine with other areas of interest.

And finally, as Coolio told me, “Stick with it. Persistence.”

Persistence + Love = Abundance.

– Creativity.

I’ve interviewed artists, musicians, writers, entrepreneurs, teachers, athletes, and realized that creativity is infused into every corner of their lives.

Someone asked me just yesterday, “Isn’t creativity about art?”

No, creativity is about everything.

it’s about all we can do to break out of the routine of every day life. To make an exceptional life.

It’s how someone makes a driverless car. Another person predicts “the next trillion dollar opportunity is VR”, another woman writes books that sell 200 million copies, an athlete escapes the ghetto to become one of the best basketball players ever, an entrepreneur changes his life in a month in the most unique way I’ve ever seen.

Creativity comes up in every single podcast I do. Here is some of what I’ve learned:

a. Every day. Be creative every day. Creativity is like sex. The more you do it, the better you get.

b. Do a “dare a day” Something that frees your brain from the routine and that takes you into the secret alternative reality where creation lives.

c. Idea Sex. I write about this everywhere. But take one idea, combine it with another, and now you maybe have created a brand new idea.

– Controlled Risk.

Every great endeavor involves risk.

Why did Elon Musk think, without any background at all, he could create a spaceship and have it fly to space?

Why did a kid from the ghetto think he can be the biggest musician on the planet?

Why did a writer who wrote a lousy first novel, couldn’t get any publisher, self-published, think he could write one of the most popular novels and movies ever?

Why did Mark Cuban think people would listen to bad audio on the slow Internet?

Why did a guy working in a cubicle for a phone company think he could become one of the most popular cartoonists on the planet?

Why did a woman in a loveless marriage, tied to her kids and housework, think she could sell 300 million copies of her books that she had yet to write?

Why did a guy with a permanent tenured professor job, quit his job, put 1000 copies of his self-published book in the trunk of his beat up car, and travel the country – selling 100s of millions of books within the next 30 years?

Peter Thiel eliminated risk by having enough money in the bank before starting PayPal, finding a small niche where he can try to be a monopoly, and then merging with his competition to eliminate competition.

Hugh Howey covered his expenses while he wrote 11 novels that flopped before his huge success (millions of copies) with “WOOL”.

Brian Koppelman spent three years studying the movie business before he left his job and then he and David Levien wrote “Rounders” and then “Ocean’s 13”.

Why and why and why?

It’s not because they took risk. It’s because they spent every day getting rid of risk.

I didn’t know how to do this.

I took too many risks and lost it all repeatedly.

So I wanted to learn what these people did. I asked them.

100% of them focused on risk rather than return.

– Hacking the ‘10,000 Hour Rule’

Every great idea in history is the bastard child of two mediocre ideas.

Wizards + Unpopular kid at school = Harry Potter

Internet + Video = YouTube

Social Media + Confirmed Identity = Facebook

Dystopia + “The Lottery” = The Hunger Games

Arc of the Hero + Taoism + Space Epic = Star Wars

Melody + Gangster Rap = “Gangster’s Paradise”

Blues + Rock = Rolling Stones, Led Zeppelin

Skiffle + Elvis Presley = The Beatles

1950s Advertising + Art = Andy Warhol’s Pop Art

And on and on.

Scott Adams put it best in podcast #200. He called it, “The talent stack.”

It’s really really hard to get to be the best in the world at any one thing.

But it’s easy to get pretty good at TWO things and then combine them. Then you are in the top 1% of the intersection.

This reduces the “10,000 hour rule” to the “Maybe 300 hours rule”.

His suggestion: get pretty good at anything. then get pretty good at public speaking.

You’ll be better than all the competition who are GREAT at the first thing. Because you will know how to present your ideas in a charismatic and visionary fashion.

This is critical for any success.

Every one of the 200 people I’ve interviewed are nuclear idea machines. They constantly come up with ideas and then combine them.

They are idea sexaholics.

10 ideas a day for six months turns you into an idea machine.

– Writing.

I’ve interviewed a ton of authors. I love writing. I love the mechanics of it.

Fiction, Non-fiction, Songwriting, TV writers, Comedy writers, Movie writers, and all the genres in-between (dirty realism fiction, narrative non-fiction, which borrows elements from fiction to create nonfiction and vice versa).

What I’ve learned:

a. Write every day. Else you get stale.

b. Don’t worry about writing bad stuff. As Mac Lethal told me, “People will only remember your good stuff anyway.”

c. There’s material everywhere. I used to think I could only write about the horrible things in my life. From my guests I realized that you can put your unique perspective on any situation and make it your own when you write about it.

d. Read a lot. The best writers are our best teachers. Warren Buffett reads for five hours a day.

e. Compassion. I re-read Cheryl Strayed’s books (or re-listen to that podcast) whenever I want to be reminded that compassion is the topic we can all relate to.

You must have compassion for what you write about. Else ego distorts the writing and it’s no good.

Happiness is Not About Metrics

No metric for success is good. Because you are unhappy until you get it, then you are unhappy when you get it because it’s never what you thought.

Everyone wants to have some happiness in their lives. Many of my podcast guests have spent part of their lives studying happiness. Seth Godin, Gretchen Rubin, Susan David, Tim Ferriss, Tom Shadyac, Dan Harris, etc

a. Don’t have external goals.

Tom Shadyac (mega movie director) told me, “happiness comes from the world happenstance – something outside of ourselves. It no longer works for me.”

A goal outside of ourselves is often out of our control.

b. Bring goals internal.

Don’t say, “I need to lose 50 lbs in a year. Say…I need to eat healthy today.” Or.. “I need to have a bestseller to be happy.” Instead..”Write today.” Or…(and I am guilty of this) “I need a million dollars today”. Instead, “How can I improve my business or my ability to generate more income today.”

Scott Adams calls this living by “systems” instead of “goals”.

c. Reduce expectations.

Happiness = Reality / Expecations.

You can change reality, but slowly. Expectations I can change in a second.

Do I need a ten million dollar house before I’m happy? Or a book that sells 2 million copies?

That I can’t change. But I can say, “I can live in almost any conditions and be happy.” Or, “I can write the best book I can” and be happy.

– Antifragility

Nassim Taleb is one of my favorite guests.

His point is that as a society, we are very fragile. If something hurts us (an economic crisis) it sends us into a death spiral of panic.

It’s not even good enough to be resilient (i.e. bounce back). It’s better to be “antifragile” – what hurts us, makes us stronger.

He writes about the economy but I ask him about my personal life (many of my podcasts are like therapy sessions for me).

He showed me how often mild discomforts, or even extreme ones, can be great ways to learn how to bounce back stronger and become more antifragile. Practice being uncomfortable every day.

Even spend time visualizing the worst case scenario so you can bounce back fast when or if bad things happen.

The antifragile person is the one who succeeds because it’s not that failure happens but LIFE happens.

– Reinvention.

100% of my guests started in one career, and changed at least three times minimum.

I studied hundreds of examples of reinvention and the result is my recent book.

But the key to reinvention is to be constantly learning and combining.

Learn new ideas, combine with old. Repeat. The results don’t add up.

They multiply.

– Influence.

Scott Adams, Robert Cialdini (author of “Influence”), Chris Voss (20 year veteran hostage negotiator for the FBI, and Dan Ariely (author of “Payoff”), Sally Hogshead (“Fascinate”) were among many guests who taught me the secrets of persuasion.

I learned enough to fill a book.

Perhaps several most important things: 

  • To be motivating, you need meaning in your life. Something you strongly believe in. This becomes infectious.
  • Always address objections. This establishes trust.
  • Likability. People will agree with you not because you make a rational argument but because they like you. Find common ground with the people you meet. Build from there.
  • People are irrational. Using rational arguments are not the key to winning people over.
  • Ask dumb questions. Gives people a false sense of power.
  • Focus on their needs, not yours.
  • Be as specific as possible.
  • Give a sense of urgency.
  • Don’t be afraid to go silent in a negotiation.

But even more important: these episodes about motivation and persuasion are my most popular episodes of all time.

People basically want to learn how to communicate (manipulate?) the people around them more than they want to learn anything else.

The skills of persuasion are perhaps the most important skills in the coming years. The 5-6 podcasts I’ve done on the topic are like a course on persuasion.

– Don’t Kill Yourself For a Job.

“The point is to make a LIVING, not a KILLING,” Derek Sivers told me.

He also told me the best way to make a living to do a lot of favors for people. Eventually you can start charging. And more and more people will come to you for your services.

He also trusted his instincts. He loved music. But he wanted to sell his music. So he built his own website to sell his music.

And then he started selling his friends’ music (doing favors). He charged for it (“Don’t be unreasonable in your favors”). Eventually he built a big business.

– Energy is your main asset, Don’t waste it.

Barbara Corcoran told me that fear, regret, negative people, bad situations will steal energy from you. Arianna Huffington told me that sleep builds up energy.

The more energy you have, the more likely you will be enter in to a state of “Flow” -as Steven Kotler told me – a state where you lose track of time and maximize productivity and creativity.

Doing things that give you meaning, that support your vision, will always give you energy.

– Finding your loves.

Chip Conley, Coolio, Judy Bume, Mark Cuban, Matthew Berry, Peter Thiel, Wayne Dyer, all had one thing in common (as did many of my guests).

They left behind the things that were making them unhappy (we only have one life) and they remembered what gave them joy and energy as a child.

Exercise: list the things you enjoyed at age 6, 10, 15, 18 and see how those things have “aged”, i.e. list ideas on how you can be involved in those interests even now as an adult.

Matthew Berry loved sports. He ended up being a top movie writer in Hollywood. But he hated it.

He quit, and for $100 a blog post started blogging about fantasy sports. Now he’s the ESPN anchor for Fantasy Sports and has built several companies in the industry.

He’s not a sports star, but he “aged” his interest to see how he can do it professionally as an adult.

Judy Blume loved storytelling a kid. But ended up with a life that did not satisfy her, in a place that did not satisfy her, in a relationship that did not satisfy her.

She quit it all and started writing again. 150 million copies later…

I did my first interview when I was in 6th grade. I interviewed the Chief Usher of the White House. And then he gave me my own personal tour. I did about 100 interviews that year of politicians. And then I stopped. Until this podcast.

– Scene, Community, Network.

Don’t try to be everything to everyone. Then you are nothing for nobody.

Find your scene – the people who share your loves and interests and you want to work with.

You learn from your scene and your community – the people who create with you and the people who love those creations.

And then network. Rather than spend a lot of ads to get people to like you – find the people in your network who love your work and spread it via word of mouth.

Daymond John could have spent millions advertising his FUBU clothing line. Instead, LL Cool J was in his network and started wearing the clothes. BOOM!

This is the fuel that can build multiple businesses and creations for you.

– Bigger is not better.

Peter Thiel told me, “Better to be a monopoly in a niche you are expert in, then a small company in a huge industry where competition will destroy you.”

Seth Godin told me, “Measure your success not by the number of “likes” but the impact you can have on someone.”

Derek Sivers turned down offers to get bigger. He wanted to stick to his indie roots and that’s how he built a $100 million revenues business.

Tony Robbins told me the story of how one of his conference attendees wanted “a billion dollars” and how that attendee thought it was good to “dream big”.

But Tony broke it down for him about what he wanted the billions dollars for. It turned out for less than 1% of that billion he could have everything he ever wanted and even that was probably too much.

– Experimentation.

AJ Jacobs creates his entire life by experimenting. It’s only a failure if you try something and you learn nothing from the result.

AJ takes what he learns, writes it in articles books, gives talks, creates opportunities, and uses what he learns to make his life better. Even if most of the experiment was a “failure”.

Tim Ferriss has a slightly different take. “Try many two week experiments.” See what works. Take the best.

Jesse Itzler hired a former SEAL to live in his house and train him for a month.

Daymond John made some hats and went to see if he could sell them in a day.

This podcast started as an experiment for me. So far, so good.

If you have something you want to try, try it. Don’t plan too far ahead.

Do a two week experiment.

– Play.

We often forget to play. I used to think I could relax once I hit some unknown goal. I didn’t even know what my goals were.

And so I never relaxed.

Ever since I had one of my initial podcasts with Charlie Hoehn (author of “Play”) I’ve tried to play every day.

Either basketball. Or a “mystery room” or chess or poker or backgammon. Yesterday I played air hockey. The day before: bowling.

Play unleashes the mind in new ways. Builds new pathways between neurons.

Jumpstarts creativity in ways you can’t expect. Makes all sorts of happy neurochemicals surge through the brain.

I remind myself at least once a day: a child laughs on average 300 times a day. An adult…five.

I try to always be somewhere in the middle.

Ugh. Too long. And this is maybe 1/100 of what I’ve learned.

Every day I think, “I’m going to quit this podcast. It’s too much work.”

But then I read a book. Or I see a person I’m curious about. And I think, “I need to know more about this.”

So I call them. I arrange to meet them. I pull out a recorder.

I start asking questions.

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