Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More

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Ryan Holiday

Ryan Holiday (@RyanHoliday) is a strategist and writer. He dropped out of college at 19 to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written four previous books, including The Obstacle Is the Way, which has been translated into 17 languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. Ryan lives on a small ranch outside of Austin, Texas, and his latest book is Ego Is The Enemy.

Ryan and I cover a lot in this conversation, including:

  • Meltdowns and how Ryan handles them
  • Workaholics Anonymous — How it works, what worked for him, what didn’t
  • The tipping points for his last book, The Obstacle Is the Way
  • External versus internal obstacles
  • Sherman versus Grant leadership and “success”
  • Howard Hughes versus Elon Musk
  • Thinking of “first principles”

If you only have 5 minutes, listen to what Ryan believes is one of the biggest threats to your creativity.

Enjoy!

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Want to hear another podcast with Ryan Holiday? — In this episode, we discuss the “big three” stoics, how Stoicism applies to the modern world, and how to improve your decision-making when stakes are high (stream below or right-click here to download):



This podcast is brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service led by technologists from places like Apple. It has exploded in popularity in the last two years and now has more than $2.5B under management. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams.

Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you — for free — exactly the portfolio they’d put you in. If you want to just take their advice and do it yourself, you can. Well worth a few minutes to explore: wealthfront.com/tim.

This podcast is also brought to you by FreshBooks. FreshBooks is a bookkeeping software, which is used by a ton of the start-ups I advise and many of the contractors I work with. It is the easiest way to send invoices, get paid, track your time, and track your clients.

FreshBooks tells you when your clients have viewed your invoices, helps you customize your invoices, track your hours, automatically organize your receipts, have late payment reminders sent automatically and much more.

Right now you can get a free month of complete and unrestricted use. You do not need a credit card for the trial. To claim your free month, go to FreshBooks.com/Tim and enter “Tim” in the “how did you hear about us section.”

QUESTION OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

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The Canvas Strategy — What Ben Franklin and Bill Belichick Have in Common

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Photo credit: ©Dan Taylor/Heisenberg Media.

Photo credit: ©Dan Taylor/Heisenberg Media.

“The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.” – Ryan Holiday

My job is usually to deconstruct world-class performers from business, military, entertainment, politics, or athletics, and then to tease out the routines and habits you can use.

In this particular episode, I’m going to share an overarching strategy that has been used by many of the greats. That includes Ben Franklin, legendary NFL coach Bill Belichick, and many more. It is also how I built my network, how my first book hit the tipping point, how I became successful at angel investing, etc.

Of course, if you’re interested in the networking part of it, you can also read the blog post and listen to the episode, How to Build a World-Class Network in Record Time. But that is bonus credit.

The secret to all of the above is the “canvas strategy.”

And in this episode, Ryan Holiday, author of the new book, Ego Is the Enemy, will teach you how to apply canvas strategy to your life. (The book is also the newest addition to my book club, which can be found at audible.com/timsbooks.)

Please enjoy this excerpt with Ryan Holiday from Ego Is the Enemy!

TF-ItunesButtonTF-StitcherButton

Want to hear another podcast with Ryan Holiday? — In this episode, we discuss the “big three” stoics, how Stoicism applies to the modern world, and how to improve your decision-making when stakes are high (stream below or right-click here to download):



This podcast is brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service led by technologists from places like Apple. It has exploded in popularity in the last two years and now has more than $2.5B under management. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams.

Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you — for free — exactly the portfolio they’d put you in. If you want to just take their advice and do it yourself, you can. Well worth a few minutes to explore: wealthfront.com/tim.

This podcast is also brought to you by 99Designs, the world’s largest marketplace of graphic designers. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs.

I used them to rapid prototype the cover for The 4-Hour Body, and I’ve also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you’re happy with or your money back. Click this link and get a free $99 upgrade. Give it a test run.

QUESTION OF THE DAY: What was your favorite quote or lesson from this episode? Please let me know in the comments.

Scroll below for links and show notes…

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The Unusual Books That Shaped Billionaires, Mega-Bestselling Authors, and Other Prodigies

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Tim books

Who are the mentors to billionaires, chess prodigies, rockstars, and mega-bestselling authors?  Who teaches them to do what they do? To achieve the success they achieve? Oftentimes…it’s books.

On The Tim Ferriss Show (iTunes, SoundCloud), I dissect world-class performers to find the tools and tricks you can use.  Here’s a full list of guests.  One of the questions I always ask is:

“What book have you gifted most often to others, and why?”  

Below is a list of answers from people like billionaire investor Peter Thiel, Tony Robbins, Pixar co-founder Ed Catmull, chess prodigy Josh Waitzkin, etc.. (And here are my own current answers, if you’re interested.)

You’ll see several books that appear more than once. Can you guess which they are?

The Ultimate To-Read Book List

Kevin Kelly is the founding editor of WIRED magazine, real-life Dos Equis “Most Interesting Man In The World.”

Favorite book(s):

Full Conversation:


Peter Thiel, billionaire investor (first outside investor in Facebook) and co-founder of PayPal, Palantir… Read More

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The Obstacle Is The Way — The Tim Ferriss Book Club, Book #4

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The_Obstacle_Is_the_Way__The_Timeless_Art_of_Turning_Trials_into_Triumph__Ryan_Holiday__9781591846352__Amazon_com__Books

This post is about the fourth book in the Tim Ferriss Book Club, which is limited to books that have dramatically impacted my life. All previous selections can be found here. Enjoy!

“Would you have a great empire? Rule over yourself.” — PUBLILIUS SYRUS

The last two weeks have been disaster after disaster for me:

  • A dear friend died unexpectedly, only miles from my home. (RIP, Seth Roberts)
  • A seven-figure business deal fell apart at the last minute.
  • Only days ago, Turner Broadcasting let me know that the May 27th digital launch of The Tim Ferriss Experiment has been canceled. Some (not all) of the higher-ups want to try selling it to traditional outlets. (Sidenote: If you bought an iTunes season pass, definitely request a refund)

Over the last 14 days, I have carried one book in my backpack to cope, all day and every day: The Obstacle Is The Way.

It has helped me to turn problems upside-down, become the calm within the storm, and even uncover unique opportunities.

“Philosophy” gets a bad rap.

Most of us know a turtleneck-wearing pseudo-intellectual who’s spent countless hours studying obscure details of Freud or post-structural lesbian feminism.  These same people sometimes purport to be “philosophical.” And for what? More often than not, to posture as a holier-than-thou jerk off. To argue over semantics that don’t matter.

Fortunately, there are a few philosophical systems that produce dramatic real-world results…without the nonsense. In other words, all substance instead of smoke.

The Obstacle Is The Way, penned by Ryan Holiday, is a collection of stories and principles about Stoicism, which I consider to be the ultimate personal “operating system” for entrepreneurs…or anyone who wants high performance under high stress.

Ryan became Director of Marketing at American Apparel at age 21 (!). He gets more heat, makes more high-stakes decisions, and take more risks in a given week than most people experience in any given quarter. He also happens to be a die-hard Stoic and incredible at putting the principles into practice.

If you want to be “anti-fragile” like Thomas Jefferson, Marcus Aurelius, and many of most dominant soldiers and investors in history, Stoicism offers the playbook.  If you want to make better decisions, if you want to smile when other people cower, it offers real tools.

To quote Andy Grove, former CEO of Intel, “Bad companies are destroyed by crisis. Good companies survive them. Great companies are improved by them.”

What if you could be a person who is improved by crisis? That would give you opportunities no one else can see, let alone grasp.

It will also make you a happier human being.

Check out The Obstacle Is The Way today:

I’m not the only one who loves it. Here are just a few of many:

“Follow these precepts and you will revolutionize your life. Read this book!”
—Steven Pressfield, author of The War of Art and Gates of Fire

“A book for the bedside of every future–and current–leader in the world.”
—Robert Greene, author of The 48 Laws of Power and Mastery

“Ryan Holiday has written a brilliant and engaging book, well beyond his years…It is invaluable.”
—Honorable Frederic Block, Judge, U.S. District Court

Seriously, check out the book.

If you’d like to hear more of Ryan’s ideas, you might enjoy the podcast interview I recorded with him recently, which has gone nuts on social media:

Question of the day: What philosophies, guiding tenets, or quotes have you found most helpful in your own life? Please share in the comments!

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The Tim Ferriss Podcast, Episode 4: Ryan Holiday

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“The impediment to action advances action. What stands in the way becomes the way.” — Marcus Aurelius

This post includes:
– Sponsor intro (please visit them)
– Episode description
– Quick favor
– Show notes and tons of useful links, including mentioned books and documentaries

This episode of The Tim Ferriss Show is sponsored by HipDial, which I’ve been a fan of for ages.

I use HipDial for conference calls: no stupid PIN numbers, no hitting #, and you get a text when people join, so you don’t have to wait. It’s rocks–try it for a free month, and you’ll never go back.

Now, on to the main event…

My guest is Ryan Holiday, who became Director of Marketing at American Apparel at age 21 (!). He’s a beast.

Since dropping out of college at 19 to apprentice under strategist Robert Greene (author of The 48 Laws of Power), Ryan has advised many New York Times bestselling authors and mega-multi-platinum musicians. He is a master of the media, and he knows how to build massive buzz while responding to unexpected crises. He can compete or counterpunch with the best.

I hired Ryan to help with the launches of The 4-Hour Body and The 4-Hour Chef. His unorthodox approaches always impress me.

I loved his new book (The Obstacle Is The Way) so much that I bought the audiobook format and produced it with him. It is the newest addition to The Tim Ferriss Book Club.

In this episode, we discuss dozens of topics, including the real-world strategies he uses to thrive (not just survive) when the world is exploding around him.

And…want to win some cool stuff today? Tweet out your favorite quote or line from this episode, using the following format, and I’ll pick a few of my favorites for prizes:

“[Insert quote]” More: https://itunes.apple.com/us/podcast/the-tim-ferriss-show/id863897795?mt=2 #TFS”

To encourage other people to retweet, try and keep your entire tweet to 125 characters or fewer. The iTunes link above will be automatically shortened.

Deadline is 8:30pm PST.

QUICK FAVOR — If you haven’t already, can you pretty please:

1) Leave a review of the podcast on iTunes here?
2) Vote as “helpful” the reviews you most agree with? Here’s the link. The vast majority are 5 stars (290 out of 333), but there’s some wild Haterade, too, if that’s your thing.

Show Notes for Episodes 4 (Thanks, Ian!)

  • The surprising story of how Ryan was introduced to stoicism by Dr. Drew
  • What makes a “quake book”?
  • How Marcus Aurelius helped Ryan survive a tough breakup
  • About esoteric philosophical ideas that are excellent tools in the modern world
  • Deconstructing the “Big 3” stoics – Seneca | Epictetus | Aurelius
  • Is stoicism compatible with material or financial success, or are they completely at odds with one another?
  • Tim’s strategy for developing connections in Silicon Valley
  • Cultivating advantageous mentorships with peak performers
  • The story of Benjamin Franklin’s lending library…

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The 5 Top-Performing American Apparel Ads, and How They Get PR for Free (NSFW)

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Above and below are five American Apparel ad campaigns that ran for less than $1,500 each. Designed to get attention and create controversy, they were covered in AdWeek, The Hollywood Reporter, Daily Mail, NBC, Gawker, and dozens of other outlets and blogs.

Despite this minuscule budget, they did millions of earned media impressions all over the world. People are still talking about them today. Click on each for more context (or, in one case, an uncensored Sasha Grey).

The real question this raises is: how do you craft an message, ad, or story that people talk about years from now?

We’ll aim to answer that in this post… Read More

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Stoicism 101: A Practical Guide for Entrepreneurs

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Stoicism was born on the porch of Zeno, but it can be used in the concrete jungle.
(Photo: Blue Cinderella)

“There is nothing the busy man is less busied with than living; there is nothing harder to learn.”
-Seneca

Few of us would consider ourselves philosophers.

Most of us can recall at least one turtleneck-wearing intellectual in college who dedicated countless hours of study to the most obscure philosophical points of Marx or post-structural lesbian feminism. For what? Too often, to posture as a superior intellect at meal time or over drinks.

Fortunately, there are a few philosophical systems designed to produce dramatic real-world effects without the nonsense. Unfortunately, they get punished because they lack the ambiguity required for weeks of lectures and expensive textbooks.

In the last three years, I’ve begun to explore one philosophical system in particular: Stoicism. Though my preferred Stoic writer, Lucius Seneca, I’ve found it to be a simple and immensely practical set of rules for better results with less effort.

Ryan Holiday is 21 years old and works directly with Dov Charney as his online strategist for American Apparel. He gets more heat, makes more high-stakes decisions, and take more risks in a given week than most people experience in any given quarter. He also happens to be a die-hard Stoic and incredible at putting the principles into practice… Read More

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