Dave Flynn on the Radio

On my 45th birthday, I decided to take stock—not with resolutions or advice, but with notes I’ve been quietly keeping for years. What started as a private “Note to Self” has grown into a list of lessons about work, attention, friendship, courage, and choosing what matters. Some are practical, some philosophical, all earned the slow way. This is a snapshot of what I believe right now—shaped by mist...

It started with a photo, a little extra weight, and a decision to do something hard. A marathon seemed simple enough—until it wasn’t. One race left me full. The next left me empty. In between were injuries, early mornings, quiet negotiations with pain, and strangers ringing cowbells for anyone still moving. This piece isn’t really about running. It’s about what goals leave behind once the medal’s...

Once a year, I publish the Recommengine: a curated list of the books, videos, podcasts, ideas, and strange little discoveries that stuck with me over the past twelve months. These are the things I’ve recommended to friends, family, coworkers, and now you—because they made me laugh, think, argue, or see the world a little more clearly. It’s long. It’s opinionated. It wanders. And if you follow ever...

This week’s blogcast starts with Billy Mack, detours through Dickens and Yvon Chouinard, and ends up right where every creator eventually lands: staring down the temptation to make solid gold shit. The shiny thing that charts well, trends well, sells well—and leaves you feeling nothing. Instead, I make the case for building the weird, specific thing you’d rip open on your own Christmas morning. A...

The final trap isn’t money or status—it’s the rice in the monkey trap: sunk costs, identity, and the illusion of meaning. In Part III, we explore why people stay in environments they’ve long outgrown, clutching rewards they can’t use and identities they didn’t choose. Freedom requires value elasticity, the courage to reprice what mattered yesterday against what matters now. Letting go feels like l...

When money stops motivating, companies don’t lose power—they just switch currencies. Titles, recognition, access, belonging: these are the subtler, more potent levers that keep people striving long after their paychecks stop mattering. From Cheers to President’s Club to “Emerging Leaders,” Part II shows how status and affiliation infiltrate our identity, how they blur the line between reward and m...

We like to think we choose our jobs, but much of the time our jobs choose us. From billion-dollar pay packages to corporate KPIs, the game isn’t about money—it’s about control. Value rigidity keeps even the richest and most powerful people locked into systems they can’t leave, and we’re no different. We learn to love the rope the longer we’re tied to it. Part I unpacks the hidden strings companies...

We all do it—round up a story, polish an answer, hide the rough edges. Not to deceive, but to belong. From Chris Rock and Ice Cube to Seinfeld and a writer named Vicky Ball, You Ain’t Gotta Lie Ta Kick It looks at how performance and authenticity overlap until even honesty becomes an act. What happens when we see the performance for what it is? Can we ever be truly real—or just more aware of the m...

Even the most talented players struggle against their own nature. When Julio Rodríguez struck out to end the Mariners’ season, it wasn’t just bad luck—it was a lesson in the cost of chasing the wrong pitch. From Ted Williams’ disciplined strike-zone approach to Josh Waitzkin’s “power of empty space” in chess, and even Roy McAvoy’s aggressive mindset in Tin Cup, success often comes from making fewe...

Why doesn’t the best product always win? Because we confuse solicitation with solutions. Elizabeth Holmes sold billionaires on promises of revolutionary blood testing that never worked. Even Apple stumbled, hyping AI features that didn’t exist. Meanwhile, Palantir bets on building software that actually solves problems. The difference? Solicitation creates “trust-lite”—influence masquerading as cr...

We talk about what’s “better” like it’s obvious. But better for whom? In Better, How?, a lesson in music, memory, and movies reveals that context and audience matter as much as product. Blog Post: Better, How?

Seth Godin has shaped my thinking more than almost anyone else. This week's post dives into the lessons that have transformed how I approach work, creativity, and life. The biggest insight? Flying too low is just as dangerous as flying too high. We've been conditioned to fear standing out so much that we've guaranteed ourselves less than we're capable of. "Being safe is risky," as Godin puts it. I...

Bill Simmons coined irrational confidence to describe players who believe they’re stars—and sometimes play like it. But it’s not just for athletes. It’s the force that drives us toward impossible catches, unlikely dreams, and bold moves in life. This piece explores where irrational confidence comes from—and why passing it on might be the greatest play we can make. Blog Post: Irrational Confidence...

Cerulean Blue and Country Music Too: What We Miss When We Dismiss. I thought country music was beneath me. Then Chris Stapleton and The Devil Wears Prada exposed the blind spots in my taste—and what I was really protecting. Blog Post: Cerulean Blue and Country Music Too

Meet Adam Zahn, the master of small deceptions. From dating apps to burger ads, Adam bends the truth to fit his needs. Know anyone like that? Blog Post: Meet Adam Zahn

Why did Jobs succeed when Ballmer failed? The Pirate and the Thief reveal the psychological principle most leaders miss: the reputation you keep with yourself becomes the ceiling for the reputation others will keep of you. Self-perception shapes everything. Blog Post: The Pirate and the Thief The Steve Ballmer Interview on Acquired Podcast

Think Different: Steve Jobs’ masterclass in reputation transformation. How self-perception becomes your company’s ceiling. Full Blog Post: Think Different

A strong reputation starts from within. The Reputation You Keep: How internal congruence shapes external perception. Full Blog Post: The Reputation You Keep

We Make Rock and Roll: How AC/DC, Jerry Seinfeld, and Mariano Rivera mastered success through consistency. Full Blog Post: We Make Rock and Roll