Dave Flynn on the Radio

Dave Flynn on the Radio

By Dave FlynnBusiness
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Dave Flynn on the Radio episodes

  • #26 | Junk Mail [blogcast]

    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 recruitment—it’s a reminder that transparency, when backed by real substance, isn’t a risk at all. It’s the ultimate competitive edge.


    Blog Post: Junk Mail

    Sponsor: Passing Notes to Strangers

    Chapters:

    00:00 - Unpacking Radical Transparency: The Ultimate Marketing Flex

    01:32 - How Harvey Mudd College Mastered 'Junk Mail' Marketing

    06:18 - Avis, Domino's, and the Power of Radical Honesty

    08:21 - The Competitive Edge of Honesty, Featuring Anna Kendrick

    11:25 - Thank You for Listening: Support the Show


    13 min
  • #25 | Keep the Brush Moving [blogcast]

    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 becomes a meditation on coaching, parenting, creativity, and growth—why constant correction backfires, why momentum matters, and why every meaningful leap requires risking temporary ruin.

    Keep the brush moving.

    Blog Post: Keep the Brush Moving

    Sponsor: 31 Easy™

    Chapters:

    00:00 - Recognizing the Inner Voice That Holds You Back

    01:34 - Bob Ross’s Journey from Military Discipline to Artistic Freedom

    03:37 - How Wet-on-Wet Painting Starves Self-Doubt of Oxygen

    05:50 - The Struggle to Avoid Over-Correction as a Parent and Coach

    08:37 - Guiding Intent and Allowing Self 2 to Figure It Out

    10:14 - Inspiring Others to Pick Up the Brush and Practice

    11:22 - The Bravery Test and Risking Temporary Ruin

    14:26 - Starving the Inner Critic and Keeping the Brush Moving

    15:22 - How to Support the Show


    17 min
  • #24 | The B Rabbit Close [blogcast]

    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 psychology behind self-disclosure, vulnerability, and authenticity, and show how you can use the same move in your own life or business.

    Post: The B Rabbit Close

    Sponsor: Passing Notes to Strangers

    Chapters:

    00:00 - The Ultimate Power Move: Owning Your Flaws Before Anyone Else Can

    02:20 - Eminem’s B Rabbit Close: Self-Disclosure and Trust Building Psychology

    04:31 - Experience the Climactic B Rabbit Rap Battle and Episode Wrap-Up


    8 min
  • #23 | Fourth Anniversary [blogcast]

    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 personal judgment have almost no correlation with what resonates. All you can do is keep swinging, keep publishing, and give luck a place to land.

    Post: Fourth Anniversary

    Sponsor: Passing Notes to Strangers


    7 min
  • #22 | Segaville, USA [blogcast]

    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 trust forms from connection, and how a company that played by different rules ended up changing the game for everyone.

    Post:

    Segaville, USA

    Sponsor:

    31 Easy

    Chapters:


    16 min
  • #21 | Magic Pills, Volume One: The Body [blogcast]

    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 you can feel.

    Get the body wrong and nothing sticks. Get it right and everything else works better. This is where the Magic Pills series starts—because it has to.

    Blog Post: Magic Pills, Volume One: Your Physical Foundation

    Sponsor: 31 Easy

    29 min
  • #20 | The Jack Story [blogcast]

    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

    10 min
  • #19 | Note to Self [blogcast]

    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 mistakes, experiments, and paying attention. Consider it unfinished. I do.

    Post: Note to Self

    Sponsor: 31 Easy


    20 min
  • #18 | What Remains [blogcast]

    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 in a drawer.

    Through ancient ships, lonely tunnels, and broken records, I explore three paths of work—and ask the only question that matters after the finish line: what remains?

    Post: What Remains

    Sponsors: 31 Easy

    20 min
  • #17 | Recommengine, 2025 [blogcast]

    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 every link, read every book, and watch every video, we may not see you again until next year. Worth it.


    Post: Recommengine, 2025

    Sponsors: 31 Easy

    44 min

About Dave Flynn on the Radio

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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.