The Workaround by Bob Gilbreath Podcast

Bob Gilbreath
  • 5.0 (7)
  • TECHNOLOGY
  • UPDATED WEEKLY

I will help you find shortcuts to business success and personal growth by sharing my stories of ups and downs on my journey through corporate innovation and software startups. Join thousands of entrepreneurs and innovators who read each week. theworkaround.substack.com

  1. 2D AGO

    Seeing through Silence, Foaling Around, and What Would You Do?

    It’s another Bob’s Bites, where every couple of weeks, I share a handful of short stories and lessons…Today: 1. What Would You Do?—a tricky sharing situation 2. Seeing Through Silence—another trick that people play on us Relevant links: Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    10 min

  2. FEB 4

    Don't Serve the Sh*t Sandwich

    Last week, I wrote about a wonderful leader from my P&G years, with whom I had repeated interactions. Regular listeners might know about his opposite: “George”, my three-up manager at the company, who taught me how not to inspire others. These kinds of reverse role models can be useful to learn from, too. George was the guy who taught me the art of making a Sh*t Sandwich. And I’m here to try and stop you from using it.   Relevant links: Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    12 min

  3. JAN 28

    True Leadership is Treating Others

    I’ll bet you’ve had a few brushes with greatness in your life. But we’re not talking selfies with celebrities here. I mean those rare moments when people in high leadership positions glide down to meet us at our junior ranks as peers rather than superiors. These encounters produce lifelong memories that we enjoy sharing with others. John Pepper is one of these special people. Today I’m sharing a few short stories about how he became part of my life, along with thoughts on why people like him are so darn rare. Relevant links: P&G Alumni Podcast with Raman Sehgal and John Pepper: https://podcasts.apple.com/us/podcast/john-pepper-100-books-that-shaped-my-life/id1509346585?i=1000741162141 100 Books That Shaped My Life: https://a.co/d/64gkbi6 Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    23 min

  4. JAN 21

    Smile Through Pain and Why VCs Rarely Make Intros

    It’s another Bob’s Bites, where every couple of weeks, I share a handful of short stories and lessons…Today: 1.     Why VCs Rarely Make Intros—get into their shoes and out of your head 2.     Smile When It Hurts—how to turn a tough conversation positive 3.     The Coin of Complaint—a little client service lesson that might save you $ millions   Relevant links: Choosing Sides on the Coin of Complaint: https://theworkaround.substack.com/p/choosing-sides-on-the-coin-of-complaint Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    12 min
  5. Choosing Sides on the Coin of Complaint

    JAN 19

    Choosing Sides on the Coin of Complaint

    When you serve clients, screw-ups are inevitable. But how you react can make it worse, or turn it positive.A few years ago, I came across an analogy that brought this lesson home perfectly. I call it the Coin of Complaint. There are two sides to this coin: “No Big Deal” and “Very Big Deal.” When a service issue occurs, the Customer or the Server picks one side of the coin, and the other party gets the other side.This little coin might save you millions of dollars.Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    11 min

  6. JAN 14

    AI Predictions are Projections

    At the end of 2025, it was time to tally the results from a bunch of big predictions about what AI would bring us…Nearly every one of them was wrong. I came up with my own AI prediction for the year ahead. It got me pretty riled up. I started to draft it here, but then realized it wasn’t really a prediction; it was a projection of a shadow lurking inside me. This turned into a story of how AI is unearthing the shadow sides of ourselves. AI can do a lot, and much more is to come in the long term. But perhaps its most important role—right now—is showing us who we are inside, both individually and collectively. Cal Newport Looks at AI Predictions: https://youtu.be/gJ8pa9NiWm4?si=tEkww-4ArTcQRG32 Joe Hovde—What are people actually using LLMs for?: https://residualthoughts.substack.com/p/what-are-people-actually-using-llms Albert Cory--Who are the Social Media Sites For?: https://albertcory50.substack.com/p/who-are-the-social-media-sites-for Following Glitches in the Matrix: https://theworkaround.substack.com/p/following-glitches-in-the-matrix What if We’re Already in Hell?: https://theworkaround.substack.com/p/what-if-were-already-in-hell Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    45 min

  7. JAN 7

    No Comparisons, New Lessons from Old Shirts, and the Corporate Empire Strikes Back

    It’s another Bob’s Bites, where every couple of weeks, I share a handful of short stories and lessons…Today: 1.     There is No Comparison—life lesson from a pro golf coach 2.     Old Shirt, New Lesson—remembering a dumb thing I did as a leader 3.     Prediction for 2006—the Corporate Empire Strikes Back…   Relevant links: Coburn Ventures podcast with Morris Pickens: https://creators.spotify.com/pod/profile/coburn-ventures/episodes/245-Dr--Morris-Pickens-on-Comparison----Reviews-Duo-2025-e38mui3/a-ac65mmk Podcast interview of Peter Williams: https://theworkaround.substack.com/p/creating-the-career-of-your-dreams Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    12 min

  8. JAN 1

    How I'm Meeting People Now

    At the end of 2023 and 2024, I looked back at my calendar and measured the years by the people I met. Today I share the results of 2025 in meetings… This year was about quality over quantity, as I worked on being a much better meeting partner with the people who grabbed time on my calendar. If you’re shopping for a meaningful New Year’s Resolution, I’ve got a few tips that might make it an excellent year for you and the people you spend time with. Warning: This is not the kind of stuff you’ll see in MBA courses or corporate training classes. And you might see new things in yourself as you become more present for others.   Relevant links: On Becoming a Person by Carl Rogers: https://www.amazon.com/dp/B00AD9YL6C Podcast discussion with Meredith Meyer: https://theworkaround.substack.com/p/lessons-on-coaching-people Podcast discussion with Alice Turner: https://theworkaround.substack.com/p/building-a-business-on-youtube-with Uncool by Cameron Crowe: https://a.co/d/bqat6yO Bowie & Crowe interview from Feb 1976: https://www.rollingstone.com/music/music-news/david-bowie-ground-control-to-davy-jones-77059/   Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours Fleet: https://fleetholdingco.com/ This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theworkaround.substack.com

    30 min
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I will help you find shortcuts to business success and personal growth by sharing my stories of ups and downs on my journey through corporate innovation and software startups. Join thousands of entrepreneurs and innovators who read each week. theworkaround.substack.com

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