Podcast Overview

I’ve been a guest on hundreds of podcasts over the years. Some go places I didn’t expect. Here are conversations organized by what you might be wrestling with right now. All research and writing by Claude, fingers crossed.

IF YOU’RE STUCK AND CAN’T START

Imposter Syndrome, Getting Unstuck and The Practice — Chase Jarvis LIVE
On the two voices in your head—the one that’s talking and the one that’s listening—and why imposter syndrome might be a sign you’re doing something right.

The Practice: Creativity Has No Guarantees — MarieTV
“Do what you love” is for amateurs. “Love what you do” is the mantra for professionals. On showing up even when you don’t feel like it.

On Creativity, Embracing Failure & Spreading Big Ideas — Rich Roll Podcast
A wide-ranging conversation about creative block, the fear of being seen, and why perfectionism is just a fancy word for hiding.

The Practice — Tim Ferriss Show
Deep dive into why quality can be a trap, why we need to separate the creative act from the business act, and what it means to be a professional.

Put Yourself on the Hook — Afford Anything
On the freelancer’s trap of staying safe vs. doing work that matters. And why putting yourself on the hook is actually less risky.

Shipping Creative Work — EntreLeadership
You don’t feel like something and then do it. You do something and then you feel it. If you want to be a runner, you don’t wait to feel like a runner.

IF YOU’RE TRYING TO FIGURE OUT YOUR AUDIENCE

How to Think Small to Go Big — Tim Ferriss Show
We pick “everyone” because infinity feels safe. But the smallest viable audience is where the leverage actually lives.

Effective Fundraising and Power Partner Principles — What the Fundraising
For nonprofits: no one donates $100 unless it’s worth $200 to them. Understanding that changes everything about how you ask.

Get Your Work Seen — Creative Pep Talk
For artists and creatives specifically—why the goal isn’t to reach everyone, it’s to matter to someone.

The Emotional Journey of Shipping Creative Work — Unmistakable Creative
Why the market doesn’t care how hard you worked. And why that’s actually liberating once you accept it.

Tactics for Building Remarkable Products — Lenny’s Newsletter
Product strategy and why most products are built for the wrong audience.

IF YOU’RE THINKING ABOUT STRATEGY

Strategy and More Humane Decisions — Six Pixels of Separation
On the Jaguar rebrand disaster, why empathy isn’t just kindness—it’s a strategic tool, and why CMOs keep getting fired every 18 months.

Creating Your Best Strategy — Something You Should Know
Strategy is the hard work we do before we do the hard work. On systems, empathy, and games worth playing.

Why Strategy Always Beats Talent — Chase Jarvis LIVE
In 1999, Walmart had a banner: “We can’t out-Amazon Amazon.” They understood strategy. Most people confuse it with tactics.

The Knowledge Project — Farnam Street
Deep conversation about decision-making, strategy, and how to think about problems worth solving.

IF YOU’RE LEADING PEOPLE (OR TRYING TO)

The Song of Significance — MarieTV
From The Song of Significance: why work isn’t working anymore, the death of the factory model, and what could replace it.

Creating Significance at Work — Coaching for Leaders
The 14 characteristics of great workplaces. And why most organizations accidentally optimize for the opposite.

Leadership, Ego, and Saying No — Techstars
Why enrollment beats compliance. What real leaders do differently.

On Culture — CultureLab
Building culture intentionally. Why “that’s just how we do things here” is both the problem and the opportunity.

IF YOU’RE WRESTLING WITH EDUCATION

Stop Stealing Dreams — Transformative Principal
We don’t teach kids to love baseball by giving them tests on statistics. So why do we teach everything else that way?

What Is School For? — Anette on Education
The only question that matters. And why most schools are still optimized for the industrial age.

The Systems That Shape Us — Alliance for Decision Education
On teaching decision-making and why schools rarely do it.

PERSONAL STORIES THAT WENT SOMEWHERE UNEXPECTED

Design Matters with Debbie Millman
Debbie asks the questions most interviewers don’t. On the earliest influences, the work before the work, and the long arc.

Big Questions with Cal Fussman
Cal brings a journalist’s eye. We ended up talking about things I rarely discuss publicly.

The Moment with Brian Koppelman
Brian and I have done many of these together. He has a point of view, and these conversations often turn into something closer to creative sparring.

Tim Ferriss (Early Episode)
One of the earlier conversations with Tim. On roasting your own coffee beans, saying no, and the origins of the work.

ON CLIMATE AND THE CARBON ALMANAC

Can Marketing Save the Planet?
Facts without intimidation. How to talk about climate without losing people in the first sentence.

Climate Change Is a Marketing Problem — Climate Changers
Community action at the smallest scale. One parent organizing five families can change more than you think.

Climate Change — Ultimate Health Podcast
Climate change as a health issue. Why this framing might reach people the environmental framing doesn’t.

Systems Change and the Carbon Almanac — Invested in Climate
How the Carbon Almanac came together: 300 volunteers from 40 countries, all working without me telling anyone what to do.

FOR ENTREPRENEURS SPECIFICALLY

Entrepreneurs on Fire
The light bulb story: I made a deal with a Hungarian factory, sold door-to-door to high school bands, and failed completely. What I learned.

On Tribes — Foundr
Building movements, not just businesses. Why the tribe is the point, not the product.

$100 MBA
Practical business advice for people building something without a safety net.