I had the body. I had the brain. I could control my state.

And I still felt hollow.

This volume is about what the optimization crowd skips: play, connection, service, gratitude, reading, and learning. The things that make all the effort worth it.

Blog Post:

Magic Pills, Volume Four: Beyond

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Shift to TRUST

Passing Notes to Strangers

Chapters:

My first book ended with a simple idea: once you really see something, you can't stop seeing it. It shows up everywhere.

In this Q&A, I explain why “little deposits of trust” only get you so far, why some of my consulting clients weren’t particularly trustworthy themselves, and what Little League baseball has to do with any of it. Shift to TRUST is available now.

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⁠Bookshop⁠⁠Audible⁠

⁠Spotify⁠

Blog Post:

⁠My New Book: Shift to TRUST⁠

Landing Page:

⁠Shift to TRUST⁠

Playlist:

⁠Shift to TRUST Playlist⁠

Chapters:

"Why the hell should I trust you?"

At twenty-two, I didn't have an answer. And the heart of the question didn't become clear for two decades. Covey's bank account? Brown's marble jar? Harvard's Trust Triangle? They didn't quite do it for me.

Shift to TRUST is a framework that works: five shifts that will show you how to build your trusted tribe in a transactional world.

Available today!

Amazon

Apple Books

Bookshop
Audible

Spotify

Blog Post:

My New Book: Shift to TRUST

Landing Page:

Shift to TRUST

Playlist:

Shift to TRUST Playlist

Chapters:

00:00 - Dave Flynn Launches "Shift to Trust" Book

02:07 - Wells Fargo, Sergeant Slaughter, and the Trust Question

07:29 - The RV Loan: An Ethical Dilemma, Deeper Trust

10:45 - Trust Theories: Marble Jars, Triangles, and Madoff

15:07 - Oxytocin, Psychological Safety, and the 5 Shifts Framework

Why the hell should anyone trust you?

That’s the question that opens Shift to TRUST, and it’s the one I’ve been trying to answer for twenty years.

As the book’s release gets closer, people keep asking what it’s about—what's the big idea. So here are five that stand out to me: why every business is in the trust business, why trust is built on evidence instead of emotion, why transparency beats mystery, why reputation travels farther than relationships, and why the ultimate goal is to move from transactions to tribe.

I hope readers are still thinking about long after they finish.

eBook pre-orders are open now:

⁠Amazon⁠

⁠Apple⁠

Print and audio on October 19th, 2026

Blog Post:

What’s the Big Idea?

Books:

⁠Shift to TRUST⁠

⁠⁠⁠⁠⁠⁠⁠⁠Passing Notes to Strangers⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠31 Easy™⁠⁠⁠⁠⁠⁠⁠⁠

Chapters:

The hard part wasn't getting people to trust me. The hard part was becoming a person worthy of trust.

That's the whole book—and the reason it took me 30 months to write.

eBook pre-orders are open now:

Amazon

Apple

Print and audio on October 19th, 2026

Blog Post:

Why TRUST?

Sponsors:

Shift to TRUST

⁠⁠⁠⁠⁠⁠⁠Passing Notes to Strangers⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠31 Easy™⁠⁠⁠⁠⁠⁠⁠

Chapters:

You can’t lose a coin flip on purpose. Trust me. I've tried.

And it turns out, that’s a useful way to think about luck and skill. A golf professional needs to be able to reproduce the bad shots as well as the good ones. A poker player can lose on purpose. Most of the time. A basketball player can try to do the same.

Then we tell ourselves what happened. That’s when things get twisted.

We turn luck into skill, failure into excuses, and a streak of coin flips into evidence of genius.

Can we reproduce the result? Reverse it? Make it fail on command?

Maybe that’s where skill really starts.

Blog Post:

Luck and Skill and Stories

Sponsors:

⁠⁠⁠⁠⁠⁠Passing Notes to Strangers⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠31 Easy™⁠⁠⁠⁠⁠⁠

Chapters:

00:00 - Unpacking Luck and Skill: The Stories We Tell

02:24 - The Golf Professional's Challenge: Making All the Shots

06:22 - Manu Ginobili and the Art of Failing on Purpose

08:35 - Annie Duke's Test: Can You Intentionally Lose?

12:51 - How Our Narrator Creates Self-Serving Bias

18:33 -From Coin Flips to Flight: The 'Lucky and Good' Principle

24:08 - Embracing Humility: When to Call It Luck

“What would Dave do?”

It’s a question I hear from friends, family, and my dozens of readers. And while I appreciate the vote of confidence, I have concerns.

People love tips. They look like shortcuts. But a tip is only useful if you understand why it works and whether it applies to you. That gives you the conviction to stick with it when things get uncomfortable.

From Jim Cramer to Siskel and Ebert to Wall Street’s favorite stock pickers, the lesson is the same: ideas on loan don’t come with conviction.

Blog Post:

Tips Are for Waiters

Sponsors:

⁠⁠⁠⁠⁠Passing Notes to Strangers⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠31 Easy™⁠⁠⁠⁠⁠

Chapters: