Ryan Holiday: On Merging Creativity and Business


For The Curious,

It was perfect timing to meet best-selling author Ryan Holiday at the two12 conference.

Ryan Holiday.jpg

The name of this conference is symbolic. The concept behind two12 is to lift businesses to their boiling point. As you might’ve already realized, two12 is the temperature in Fahrenheit degrees where water begins to boil.

A single degree can make the difference between boiling and not boiling. Finding that last degree — between 211 and 212 — is what this conference is all about.

We were both invited to be mentors. I’d never mentored at a conference like this before, so I watched Ryan advise the entrepreneurs who’d come to lift their businesses, and I was quickly fascinated.

I knew Ryan as the best-selling author of The Obstacle Is The Way. I also knew he founded a creative agency called Brass Check that advises clients like Google and assists best-selling authors.

It’s one thing to know that. It’s another to watch Ryan at work.

Ryan was able to listen to an entrepreneur and immediately grasp exactly where her or his business was at and then guide them to where they needed to go — often with only a single question.

And that’s what my conversation on Big Questions is about. How Ryan managed to master both the writing and the positioning.

It was a great time to meet Ryan because I have to think about some business decisions of my own. My original deal for Big Questions has concluded and I’m now a free agent.

I may decide to bring in some new advertisers. I also noticed that Tim Ferriss asked his readers if they’d prefer that he shift from an ad-based model to a Patreon-based model, where listeners make monthly contributions for content and get other benefits and perks. This has me curious – because people have been asking for other benefits. And I’ve got some.

So I’m asking everyone who listens to Big Questions to take a survey at calfussman.com/survey so I can see what might appeal to you.

I’ve never done anything like this before. For decades, I’ve been the interviewer and writer. I’ve never been on the other side of the coin. But now I have to understand what you like. Thanks in advance for filling out that survey.

You don’t have to worry about any of your information being passed on. It’s simply to let me know what you’re thinking.

I’m very grateful to all of you for coming along on the journey. It feels like I have a whole lot of new friends.



Kevin Hekmat3 Comments