Dave Flynn

Dave Flynn on the Radio

Business EN ↓ 44 episodes

The #1 blogcast on the internet. Dave Flynn reads his weekly essays on business, creativity, and personal development so you don't have to. New episodes every Monday at WinWithFlynn.com.

Author

Dave Flynn

Category

Business

Podcast website

winwithflynn.com

Latest episode

Jul 6, 2026

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Episodes

#44 | The Plus: Part 3, Keep Diverging [blogcast] 06.07.2026

The nine-dot puzzle has been around for decades. Connect all nine with four straight lines…without lifting your pen. In the control group, nobody solves it. Then researchers temporarily suppress the rule-following part of the brain with electrical stimulation. Forty percent crack it. The puzzle didn't change. The rules didn't change. The frame did. This is Part 3 of The Plus. We get into c...

#43 | The Plus: Part 2, The Atrophy Problem [blogcast] 29.06.2026

In April, the Artemis II splashed down after a ten day trip around the moon. Three of the four astronauts couldn't walk off the deck. Ten days. From able-bodied to not. Your brain works the same way. This is Part 2 of The Plus. We look at the atrophy problem—what happens when you let AI do the cognitive lift, and what an MIT study found when they wired up 54 essay writers with EEG headsets. We...

#42 | The Plus: Part 1, Working With the Robots [blogcast] 22.06.2026

In late 2024, AI-generated articles passed human-written ones. Twelve months later, AI took the lead online. Then the volume plateaued. Not because the robots stopped writing. Because nobody was reading. This is Part 1 of The Plus, a five-part series on working with the robots. We start with the Super Mid Plateau—the strange ceiling AI content has hit and why writing is the medium where humans sti...

#41 | Is This Thing On? [blogcast] 15.06.2026

In 1951, a comedian named Jack Roy walked away from the stage. Twelve years later he came back as someone else. And I think about Jack a lot lately A piece about writing into the void, what the kids are watching, and finding the difference between asking the room if it's working and telling them what's really going on. Blog Post: ⁠ Is This Thing On? Sponsors: Passing Notes to Strangers Cha...

#40 | Winning and The Wave [blogcast] 08.06.2026

At the 2003 U.S. Open, on center court, Pete Sampras emerged wearing a dark suit, open collar, surrounded by legends. He is retiring, and before he says a word, he’s overcome. He can’t get through it. Then Agassi appears on the screen—prerecorded, because he's still playing. "If I'd beaten Pete more often, or if he'd come along in a different generation, I'd have a better reco...

#39 | Anchors Aweigh! [blogcast] 01.06.2026

You've heard a guy at a barbecue call his wife "the old ball and chain." It's a joke. It's also a lie. The real ball and chain travels with you everywhere you go. And most people spend their whole lives hacking at the wrong ones. This week's post is about two kinds of anchors — the ones that hold you in place, and the ones that pull you forward. The trick is telling them...

#38 | I Know, Right!?! [blogcast] 25.05.2026

We all say it. “I know, right?!?” It rolls off the tongue so easily that we don’t even notice we’re doing it. But that little reflex might be costing you more than you think. It closes doors, shuts down conversations, and worst of all, it fools you into thinking that having heard something is the same as truly knowing it. Spoiler: it’s not. So what if the real flex isn’t “I know” at all? Blog Post...

#37 | Let's Be Honest [blogcast] 18.05.2026

Why are we quicker to tell someone they have spinach in their teeth than to tell them they look great? A.J. Jacobs called it radical positive honesty—if you think something good and keep it quiet, you're lying by omission. Sylvester Stallone's entire career exists because one Harvard professor told him the truth at the right time. Not when his talent was undeniable. When it was still formi...

#36 | The Brain Bucket [blogcast] 11.05.2026

How the hell do you post every week? That's the question I get more than any other. People assume the answer is discipline, or time management, or some freakish typing speed. It's none of those things. The answer is a catchall folder in Apple Notes called the Brain Bucket. Every idea, quote, and observation goes in. Most of them just sit there. But every once in a while, one new note lands...

#35 | Cheers From A Stranger [blogcast] 04.05.2026

I remember the pain of those final miles. Heavy legs, every step negotiated. But somewhere in that last straightaway, I heard cowbells and cheering. Strangers—families waiting for their own runners, neighbors with too many mimosas—were cheering for me. My eyes welled up. I've found the same is true with writing. The more distant the person, the more the encouragement means. Your inner circle l...

#34 | Magic Pills, Volume Two: The Brain [blogcast] 27.04.2026

I jumped into a freezing pool by accident and came out changed. That’s been my approach to these magic pills: try it, jump in, keep what works, and discard the rest. This volume covers the few mental performance tools that earned a permanent spot—morning sunlight, creatine, cold exposure, high-EPA fish oil, and fermented foods. No hype, no gimmicks. Just protocols with real effect sizes: depressio...

#33 | The Editors [blogcast] 20.04.2026

I went looking for a developmental editor and accidentally ran a live experiment on trust. Dozens of polished proposals came in—impressive, credentialed, and completely generic. Not one engaged with the actual work. Then one editor did something simple: he read it. What followed was specific, thoughtful, and honest feedback that immediately stood apart. It clarified something I’ve been circling fo...

#32 | The Collison Installation [blogcast] 13.04.2026

Stripe is now worth over $100 billion, but it started with nine lines of code and a radically hands-on approach. When potential customers showed interest but hesitated to act, founders John and Patrick Collison didn't just send instructions—they asked for their laptops and installed the code themselves. This "Collison Installation" wasn't just about removing friction. By sitting...

#31 | The Broccoli Problem [blogcast] 06.04.2026

What if your incentive system is quietly sabotaging the very behavior you want? From broccoli and pudding to bonuses and beach trips, most rewards teach the wrong lesson. They signal that the work itself has no value—only the prize at the end does. Over time, that logic creates compliance machines, not committed people. In this sharp, story-driven essay, David Flynn unpacks the “Broccoli Problem”...

#30 | Choose Your Customers, Choose Your Future [blogcast] 30.03.2026

Every business makes a critical choice early on: Who will we serve? Most don't even realize they're making it—but that choice determines everything that follows. In the 1930s, Barnett Helzberg Sr. made a decision that seemed crazy: he would only sell "Certified Perfect" diamonds. His competitor Zales took a different path, serving middle America with accessible jewelry. Both star...

#29 | All-22 [blogcast] 23.03.2026

You’re in the match. Heart racing. Three seconds to decide. You make your move—and get pinned. Your coach says, “You had it the whole time.” The problem wasn’t effort. It was perspective. In football, teams use something called the All-22—a camera angle that shows every player on the field at once. It’s humbling. It reveals what really happened, not what you felt happened. What if you had that for...

#28 | Let Them Play [blogcast] 16.03.2026

At 21, Jack Smith looked at the mobile ad industry and said "these ads obviously suck"—then built a $750 million company proving it. The secret wasn't better video. It was the same insight that changed music retail, reshaped e-commerce, and sits behind every great return policy ever written: stop trying to convince people, and just remove the risk. This is the story of Vungle, playab...

#27 | The Man in the Mirror [blogcast] 09.03.2026

Wade Boggs ate chicken before every game. Jason Giambi had a lucky golden thong. Moises Alou peed on his hands. Baseball players negotiate with randomness the only way they know how—rituals, superstitions, anything to feel in control. This piece is about something different. The performers who figured out how to control the one thing that actually can be controlled: which version of themselves sho...

#26 | Junk Mail [blogcast] 02.03.2026

When Harvey Mudd College mailed envelopes labeled “JUNK MAIL,” they took a counterintuitive approach that worked. In a sea of glossy brochures and empty slogans, their humor and honesty stood out. They didn’t try to impress—they connected. From Harvey Mudd to Avis and Domino’s, brands that own the truth earn something flashier campaigns can’t buy: trust. This isn’t just a story about college recru...

#25 | Keep the Brush Moving [blogcast] 23.02.2026

Before he painted happy little trees, Bob Ross spent twenty years as Master Sergeant Robert Ross—the voice that corrected, inspected, and demanded perfection. This piece traces how he deliberately killed that voice and built a method designed to silence self-doubt by never stopping. Wet-on-wet painting wasn’t just a technique; it was a way to starve the inner critic of oxygen. Along the way, it be...

#24 | The B Rabbit Close [blogcast] 16.02.2026

Ever notice how some people can turn criticism into their secret weapon? That’s the B Rabbit Close, named after the climactic rap battle in 8 Mile. By owning your flaws before anyone else can, you disarm critics, earn trust, and even win over skeptics. Billionaire Bryan Johnson does it with his “Snake Oil” olive oil — poking fun at himself before others can. In this blogcast, we break down the psy...

#23 | Fourth Anniversary [blogcast] 09.02.2026

Last year, a post I barely thought about ended up driving two-thirds of my site’s traffic. Not my favorite, not my best work, just something I found interesting enough to put into the world. Then history rhymed, the moment shifted, and it exploded. This essay is about Black Swans, power laws, and why creative hits can’t be predicted—only discovered. It’s a reminder that effort, confidence, and per...

#22 | Segaville, USA [blogcast] 02.02.2026

Welcome to SEGAVILLE, USA—where SEGA finally got through to Walmart. When the world’s biggest retailer shut them out, SEGA didn’t argue harder in the boardroom—they listened harder in the real world. What followed was a guerrilla campaign built on empathy, not ego. Kids became the messengers, and the message was simple: fun wins. This is the story of how understanding outpaces persuasion, how trus...

#21 | Magic Pills, Volume One: The Body [blogcast] 26.01.2026

Everyone wants the one thing that changes everything. It doesn’t exist. But a handful of “almost unfair” body habits come close. This is the foundation—sleep, walking, strength, cardio, heat, and simple glucose control—stacked at the minimum effective dose. Not beach muscles. Not biohacking theatrics. Just practices that quietly compound: lower mortality, better mood, more energy, and resilience y...

#20 | The Jack Story [blogcast] 19.01.2026

Have you ever met a customer so frustrated you didn’t know where to start? Barnett Helzberg Jr.’s The Jack Story shows why it’s not always about the problem—they’re carrying the weight of their journey before they even reach your door. Post: The Jack Story Sponsor: Passing Notes to Strangers

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