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. 3D AGO

    Retiring Early with Scott Aaron

    Scott Aaron recently wrapped up a long career focused on market research and strategic insights. He has worked at a combination of BigCo, agency, scaling startup, and his own consultancy. We bumped into each other randomly for 20 years, then began sitting down for quarterly coffees. We talk business, guitars, and especially our shift away from full-time careers as 50-somethings. Some might even call this “early retirement.” Scott stepped away from his job last year, and I finally had the chance to drag him in front of a mic to share his story of making the move. Here are a few things we discuss: ·      What goes into making the decision to punch out (early) ·      It takes time to unwind ·      Self-work becomes the work ·      We need a new name for this stage While our conversation will be especially relevant for people nearing the precipice of hanging it up, I think there’s much more value here for those who are earlier in their careers. They have the chance to make small changes today to put themselves in a perfect position far down the line. Relevant Links: Scott Aaron on LinkedIn: https://www.linkedin.com/in/scott-aaron-b30a271/ 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

    1h 10m

  2. APR 8

    Revealing My Alter Ego: The Sign Avenger

    There are some pretty obscure superheroes in the Marvel Universe. ForgetMeNot has the power to make people forget he exists the moment they stop looking at him. He’s been a member of the X-Men for years, but no one remembers. Gin Genie creates seismic vibrations, but only when drunk. Bailey Hoskins has the power to explode…once. You might remember him from X-Men: Worst X-Man Ever. But there is a hero even Marvel forgot to cover: The Sign Avenger. By day, he’s Bob, a mild-mannered advertising industry executive. But on the weekends, he fights evil-doers by using his powers to spot illegally placed advertisements and remove them. For years, only his wife, children, and a handful of close friends knew of my alter ego. But now is the time to reveal all. This is my origin story…and an invitation for you to join my cause. Relevant links: Maryland’s Sign Avenger: https://dbknews.com/0999/12/31/arc-j6khb6dx2vdqfk2ibciiaincr4/ The Next Evolution of Marketing: Connect with Your Customers by Marketing with Meaning: https://a.co/d/0j38tpMv 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

    16 min

  3. APR 1

    Know Your Non-financial Motivators

    There are two topics that routinely trigger my attention and ire: 1.     When consultants claim to know things the rest of us don’t. 2.     When business leaders still don’t understand how to properly manage humans. McKinsey’s State of Organizations 2026 report hits on both. It suggests leaders don’t know how to build culture or motivate their employees, despite many of them spending billions with consultants like McKinsey. The company has made billions per year advising these kinds of companies—their clients—on how to restructure business units and culture, yet none of this work has delivered meaningful improvement. I dug into the report. And what I found surprised me: An insight that McKinsey’s own researchers and analysts missed. It may be the secret to motivation that we’ve been waiting for, and you don’t have to hire a consultant to start practicing it today. 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

    25 min

  4. MAR 25

    A Commission Cap is a Growth Cap

    There are some things you learn in business that are so utterly basic—such absolute no-brainers—that you figure the whole world understands it by now. But every few weeks, someone reminds me that there are a lot of simple mistakes being made out there. It’s stuff you shouldn’t have to learn through a $100k MBA or $10k leadership retreat. Common sense is free. But something bigger and more common gets in the way: Our Egos. This is the story of a classic business blunder, and a signal for when it’s time to escape.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

    14 min

  5. MAR 18

    What Your Biography Says About Me

    Have you ever thought about what the things you read say about you? Like everything else we do or say, our choices are mirrors. The other day, I realized that almost every piece of long-form content I consume now is biographical. Substacks that focus on personal stories. Autobiographical books. And podcasts with hosts and guests that share life experiences. I suddenly wondered why I turned this way, and came up with a few insights. Here’s why delving into biographies might be the next to-do for you, too. Relevant links: There are too many content links to list here, so head back to the Substack post for ‘em: https://theworkaround.substack.com/ 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

    16 min

  6. MAR 11

    Who is They? This is Us

    How would you like to read people’s minds? As a business leader, wouldn’t you love to know if your employees are happy or disgruntled? If they are concerned or focused? Locked in for the long haul—or interviewing for a new gig? It’s possible. Right now. This doesn’t require an AI bot to surf CRM activity. It’s not some kind of SaaS tool that checks employees’ LinkedIn latest connections for warning signals. And you don’t have to hire an in-house medium. But it does involve the use and observation of certain magic words…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

    11 min

  7. MAR 4

    Buying from Friends, Read Speed, and Marker Management

    It’s another Bob’s Bites, where every couple of weeks, I share a handful of short stories and lessons…Today: 1.     “I’m only working with friends from now on”—a Heard on the Street trend? 2.     The Need for Read Speed—a cool demo to see for yourself what speed reading can do 3.     Magic Marker Management—Bob’s Whiteboard Etiquette   Relevant links: Speed Reading Demo: https://substack.com/@jameslucasit/note/c-202186114 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

  8. FEB 25

    I Crashed an Annual Offsite

    Nearly two years ago, I announced the launch of A2 Influence, a reboot of the startup we sold in 2020, aimed at bringing our dream team back together and delivering click-worthy custom content and influencer campaigns. A big difference in this reboot, and a first for me in founding startups: I’m not the CEO. It was a bit surreal to be a participant in the company’s annual offsite. But it gave me the chance to observe some old and new ways a company can get off to a strong start in both financial and personal growth. I think these are worth sharing with leaders who are interested in building better. (Hint: That’s you!) Relevant links: Grow Bigger with Smaller Teams: https://theworkaround.substack.com/p/grow-bigger-with-smaller-teams 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

    16 min
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Ratings & Reviews

5
out of 5
7 Ratings

About

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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