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In this episode of our series World’s Most Interesting People, I sat down with Ryan Holiday. 

Ryan is the bestselling author of Trust Me, I’m Lying: Confessions of a Media Manipulator Perennial Seller: The Art of Making and Marketing Work that Lasts; Ego Is the Enemy and more. Ryan sat down with me to discuss his people hacks and how to get buy-in on ideas. 

How to Find Your Audience Circles

Do you have a method or framework for dealing with people?

As a writer, Ryan thinks about the other side and asks himself who’s on the other side of his work. Ryan says that many authors only write about what they’re passionate about and rarely think about the goals and mindset of their readers. He says it’s not just about empathy—it’s a more calculated and thoughtful decision and about finding the answer to “Who am I making this for? What is their life like? And how is this delivering value to them?”

Ryan took advice from Robert Greene, who encourages authors to have diversity in their examples and writing. It’s more than just inclusion of race and gender. It’s about developing your reader personas—be it soccer mom, corporate executive or 17-year-old trying to figure out life. As Ryan is writing, he thinks about how his words may be interpreted from all these different perspectives and develops examples to match each persona.

I’m trying to think of diversity of examples, eras, timeframes… by really thinking about who’s on the other side. I’m making sure it does resonate with those people.

Ryan Holiday

Do you have different people or personas for every book?

Ryan thinks about his audiences like concentric circles. In the center is your ideal reader, and as the circles grow, the audience possibilities grow with them. Ryan maintains the core reader never is alienated, while also writing to members of the outer circles. Samantha from Sex and the City says it best: “First come the gays, then the girls, then… the industry.” It’s important for authors to think through how their different audiences influence each other.

When you meet someone, are you thinking about what circle they may fall into?

Ryan tells us that when he’s writing, he often can think of someone (a family member, colleague or even his past self) that needs the book he’s writing, that he can help them with his message. He also warns against writing for everyone—authors need at least one ideal reader.

Action Step: Find your ideal reader, client or customer.

Get Your Influencers to Read, Respond and Act

How do you connect with influencers so they will trust you?

Ryan tells us that many influencers want to share your awesome thing and are usually already fans of your type of work or product. However, being a fan doesn’t necessarily mean that your thing fits into their business.

“The ask is less important than the match.” –Ryan Holiday

For example, Captivate is about human behavior and decoding the people around you. It wouldn’t make sense for us to reach out to a medieval historian to promote the book to his or her audience because there isn’t a clearly defined interest match.

Action Step: Just like you have to get to know your audience and ideal reader, you also must define your media and influencer pool.

What are some of the best or worst pitches you’ve received?

Ryan shares one of the worst pitches he received. Someone he didn’t know sent him a calendar invitation to chat—without ever having a conversation to confirm. Ryan’s other pitching pet peeve? When someone sends one email followed by dozens of others. He tells us that he’s noticing these types, but they aren’t making a good first impression.

One way to make a memorable (and positive) first impression when pitching is to do the pitching yourself. If it comes from someone else or someone on your team, the pitch’s authenticity is lost, and your influencer is less likely to say yes to your ask.

Acton Step: Break through the noise in a different way. Tell your influencer how your content or product matches what they do as well as how your work stands out from the crowd.

A Special Note for Introverts

Do you consider yourself an introvert, extrovert or ambivert?

Ryan is a self-proclaimed super introvert.

“The reason I’m good at writing is because I was frustrated in an extroverted world.” –Ryan Holiday

Do you have any tips for introverts on conversation or how to survive?

Competence is key for introverts. Ryan used to fear public speaking until he realized he knew more about his speaking topics than anyone in his audience. The way he saw it, they couldn’t prove him wrong even if they wanted to! Ryan has abandoned any lingering impostor syndrome by believing in his work and reminding himself that this is what he does and this is his message to share with the world.

Action Step: Stay in your lane and confidence will come naturally. Rather than fighting what the world is telling you, embrace it. For introverts especially, check out Ryan’s book The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph and remember, find your strengths and find your people.

Check out more of Ryan’s work: 

Daily Stoic Blog 

How to Deal with Difficult People at Work

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