Ryan Holiday: How to Create Work That Lasts

Ryan Holiday is an author and media strategist. His career in marketing started at age 19, where he dropped out of college to work with Robert Green. He soon found his way as the director of marketing for American Apparel, then went on to start his own creative agency, Brass Check, who advises the likes of Google, Tim Ferriss, and Tony Robbins. He’s quite the writer, making the New York Times bestseller list with multiple of the 6 books he’s released in the last 5 years.

Ryan is a master marketer and what you’ll find at the core of his marketing principles are his personal principles. He applies a Stoic philosophy to everything he does and this episode is overflowing with philosophies, self directed questions, and stories that has helped him make work that stands the test of time, and will help you do the same.

In today’s episode:

Good marketing isn’t taking pictures or writing copy that sell shoes anymore. It’s just as much about making work that starts a discussion.
You’re going to get a little crash course on Stoic philosophy and how to use your own mindset to propel your creative endeavors in three simple but challenging steps. Control your perception, take action, and look forward to the transformation that hardship brings.
The two questions you should be asking yourself before starting any creative project are “who is this for?” and “what does this do for them?” If you think long term about the impact that you want to make, it will help you persevere when the going gets tough.

Enjoy!

Nobody cares what you’re thinking about doing. Talk about your ideas after you’ve started them and then show people what you’ve done.

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Some Questions I Ask:

How did you go from an LA and New York City boy to living the country life in Austin Texas? [1:40]
How did you get into the marketing world and how did you get where you are today? [5:20]
Give us the backstory on how and why you thrust Stoic philosophy into the limelight. [12:47]
How can creatives and entrepreneurs use stoic philosophy? [17:20]
Is it like awareness practice where you’re asking yourself “what does this mean?” [20:32]
Talk to me about steps two and three. [21:29]
Let’s talk about Ego Is the Enemy. What role does ego play in the success and problems for so many? [27:42]
How do you talk to people about choosing their craft? [34:30]
Walk us through the concept behind Perennial Seller and what was the “aha” for you that made you decide to make the book. [36:14]
Talk to me about your process and what are the habits of the people who make great work? [46:35]
Talk to me about what I call “the other 50%”. [50:50]
What does having one’s shit together mean? [54:55]
How do you think about hacking? [57:30]
Give us a couple of helpful frameworks from Perennial Seller. [1:00:30]
What are some things that are applicable to modern leadership? [1:05:20]
Do you think that leaders are wildly deficient in leading by story? [1:07:50]
What role does creativity and innovation play inside the companies that you’re speaking at? [1:10:20]
What role does inspiration play? [1:12:00]
What’s the best way to stay in touch with you? [1:19:56]

In This Episode, You Will Learn:

How Ryan uses a rural lifestyle to find balance, stay humble, and keep his mind and calendar free from distractions. [1:55]
Ryan thought he was going to light his marketing career on fire by releasing his first book, Trust Me I’m Lying, but he found that going against the grain launched his career and love for writing [5:25]
If you’ve ever woken up upset about the news, but you don’t really know why, you might want to learn about fake news marketing techniques. [7:30]
How leaning into the quick spread of information was a key element in my commercial success. [9:49]
The new world of marketing is about starting conversations. [11:02]
How Adidas has usurped Jordan as the number two shoe brand by tapping into cultural icons. [12:40]
What Ryan finds most interesting and applicable about Stoic philosophy is that it’s just so darned practical. It guides you through real life moments. [14:46]
Stoicism lesson #1: Perception is everything. There is no good or bad, there’s just how you look at things. [18:01]
Check out Marcus Aurelius’ book, Meditations, where the philosopher used journaling as a way to keep perspective. [20:46]
The second step of Stoicism; What do you do with this information? [21:35]
Nobody cares what you’re thinking about doing. Talk about your ideas after you’ve started them and then show people what you’ve done. [24:02]
The third discipline: how do you deal with those moments in life that kick your ass. Thomas Edison’s building was burning down and he famously said “Go get your mother. She’s never going to see a fire like this again.” [24:46]
The fact that things are challenging often times means they are worth something. If the things that you wanted to accomplish were easy, everyone would do it and there’d be no value in them. [26:29]
The difference between ego and confidence is evidence. [28:38]
How social media makes people assholes. [29:30]
Austin Kleon – “You can’t be the noun without doing the verb.” [33:00]
If you’re stuck between choosing between two opportunities, ask yourself which one you’ll learn more from. [35:05]
Seinfeld has made $3 billion since the show went off the air. [42:07]
How to think about creating perennial sellers. This is a blank that does blank for blank. [43:00]
Your thing isn’t going to last if it’s based on things that won’t last. [45:25]
Why you need a network you can trust. Because it’s near impossible for you to see your own work objectively! [50:00]
Being great at your craft is crucial, but if you want to be successful, you’ve got to get great at the other 50%; marketing, positioning, networking, etc. [50:50]
The world isn’t asking for more amazing stuff. It’s asking why it should choose your amazing stuff over the rest of the amazing stuff. [54:20]
Books have covers to judge them by. What does your cover say about you? [55:10]
Why Ryan chooses to prioritize principles over formulas, hacks, and shortcuts. [59:10]
Why you need to ask yourself “who is this for?” and “what does this do?” every time you start a new creative project. [1:01:10]
Why you should be giving your work away (not to be confused with working for free). [1:03:10]
Why speaking and leading in terms of narrative and stories may be your best bet for getting your point across. Check out the book by Peter Guber, Tell to Win. [1:06:20]
The role of the leader. [1:09:00]
Check out Ryan’s book, The Daily Stoic, and sign up for the Daily Stoic newsletter. [1:14:55]

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