#169: Useful Lessons from Workaholics Anonymous, Corporate Implosions, and More

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" Enjoy! Show notes and links for this episode can be found at www.fourhourworkweek.com/podcast. 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.”  *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews! For show notes and past guests, please visit tim.blog/podcast. Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday. For transcripts of episodes, go to tim.blog/transcripts. Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form. Discover Tim’s books: tim.blog/books. Follow Tim: Twitter: twitter.com/tferriss  Instagram: instagram.com/timferriss Facebook: facebook.com/timferriss  YouTube: youtube.com/timferriss Past guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.