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PODCAST

The Workaround by Bob Gilbreath Podcast

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

technology

All Episodes

19:16

How I Pick Leaders to Invest In

The Workaround by Bob Gilbreath Podcast ·

2025/07/02

Smart public investors seek uncommon insights about the CEOs of companies to make better buy, hold, and sell decisions.Even smarter public investors look for diverse insights on what makes a great leader from other people who assess leaders for a living, such as executive recruiters, pro sports psychologists, and startup founders like me! My friends Pip and Brynne recently invited me on their podcast to share a few things I’ve learned the hard way, and I’m taking this opportunity to outline my

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16:18

It's OK to Meet Local Friends at Faraway Conferences

The Workaround by Bob Gilbreath Podcast ·

2025/06/25

“Funny how we have to come all the way out here to meet.”That’s what my friend, Jack, says as we sit down for breakfast on a beautiful, sunny morning at an outdoor cafe across from the ocean.His observation is one that we’ve all heard a hundred times in conferences around the world. It never gets old to hear this self-owning joke because it’s so true and so strange. But no one goes past the observation to break down why we meet out here more often and what that means.This time I observed, and now I

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61:10

Business Media is All in the Mind

The Workaround by Bob Gilbreath Podcast ·

2025/06/18

I’m excited to share the next podcast episode in my series of conversations with interesting people on topics where business and life intersect.My discussion partner this week, Joe Hovde, is a data scientist who has worked in retail media, the venture capital industry, and now the podcast+broadcast business at Spotify.We worked at the same company for a few months years ago, but never met until I became addicted to his Substack, Residual Thoughts. Over there, Joe shares “short, data-centric

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19:14

The Fall of a Young Founder

The Workaround by Bob Gilbreath Podcast ·

2025/06/11

Recently, a brilliant young founder came to me with a startup idea. In this case, “young” = high school. Junior year.Instead of judging his idea or spouting off a lifetime of advice, I told him the cautionary tale of another young founder who rose to great heights with potential, yet eventually lost it all.I followed this story for over a decade, and I’m still learning from it. Now it’s your turn.Adam Mastrioanni’s “The Bluetooth Test and other keyholes to the soul.”

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19:35

How to Kill Your Ideas

The Workaround by Bob Gilbreath Podcast ·

2025/06/04

One of the interesting things about being an entrepreneur is discovering how many other people would like to follow in your footsteps—and are hungry for advice.Years ago, I would fill a half-hour conversation with my assessment of the idea, keys to success, and watchouts.However, I’ve finally realized that my evaluation of an idea is essentially meaningless. I’ve seen so many “great ideas” of my own die an ugly death, and frequently been surprised when products I thought were dumb ended up as

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15:45

The Work Advice that Changed My Life

The Workaround by Bob Gilbreath Podcast ·

2025/05/28

Twenty-seven years ago this month, one of my first managers, Ann, shared something with me that changed my career and life for the better…In coaching me on how to work with my agency, she said: “They don’t work for you, you work for them.”It blew my mind at the time, but eventually it made sense. I used it to great success and continued to find new ways to be a servant leader throughout my career.I’ll bet you can similarly rattle off a phrase or two that made a big difference in your work+life. But

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17:23

Trust the Process, Be the Butterfly

The Workaround by Bob Gilbreath Podcast ·

2025/05/21

I wasn’t planning on posting this week. The long Memorial Day weekend is coming up in the U.S., and I know from previous years that open, listen, watch, and engagement rates plummet starting now.But about ten different synchronicities—including from people close to me—suggest that people are really struggling out there.Welcome to the challenge of our generations.It sucks, it’s not fair, it’s been going on too long, and it feels like we’re sacrificing our children to some golem of change—with no

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18:43

What's Your "Real" Business?

The Workaround by Bob Gilbreath Podcast ·

2025/05/15

Do you know why people buy your company’s brand and category? Are you really sure?Often we’re fooling ourselves…or at least not digging deep enough to understand how these crazy people called “customers” actually make decisions.It takes lots of curiosity—and usually getting personally embedded in a business—to see how things really work.Here I share the lesson I first learned from my friends on Downy—the product that’s really Love in a Bottle—then went on to practice myself on Mr. Clean Magic Eraser

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19:49

Why Do Good People Keep Bad Company?

The Workaround by Bob Gilbreath Podcast ·

2025/05/07

Why do good people work for raging a-holes? Several friends of mine still work for a CEO known in the industry as The Monster.There are a lot of CEO monsters out there. I have spent many hours wondering why people suffer under their abusive ways.This episode is an exploration of the reasons, a lot of warnings, and, of course, a turn of the mirror back on myself. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit

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29:13

Why an IPO is often DOA

The Workaround by Bob Gilbreath Podcast ·

2025/05/01

Is there anything in the business world more celebrated than an IPO?After many years of skill, luck, and grinding, your company name goes up in lights—with its own ticker symbol—and people worldwide can own a piece of the magic you and your team made.1Of course, a lot of cash comes along with it, too. Some access it before others, of course…An IPO is a game-changer for a company’s founders, investors, employees, and countless stakeholders who helped them get there.But the game of company-building

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66:49

Creating the Future of AI with Marc Stoiber

The Workaround by Bob Gilbreath Podcast ·

2025/04/23

My discussion partner this week, Marc Stoiber, is a Founder, Consultant, and Strategist who (re)invents leading brands for a living. I first got to work with Marc when he was Executive Creative Director for the Grey advertising agency. Together, our teams turned around the iconic Mr. Clean brand.Marc told me he was building a one-person strategy+creative agency…with the help of an army of AIs. That stopped me in my tracks—and I just had to get the rest of the conversation on the record.Click below

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21:07

Grow Bigger with Smaller Teams

The Workaround by Bob Gilbreath Podcast ·

2025/04/16

Re-orgs…Is there a more dreaded hyphenated word in business-speak?You’ve been there: The surprise all-hands meeting. The admission of challenges from within and without. The syrupy faux excitement for the future. The release of new org charts with fresh reporting relationships. And the inevitable departure of trusted colleagues.Businesses and organizations must evolve. But does it have to be this hard?I don’t think so. Years ago, my partners and I lucked into selecting an organizational structure

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34:55

Getting to Default Yes

The Workaround by Bob Gilbreath Podcast ·

2025/04/09

Last week, I wrote a fictional story for this newsletter. Aside from a few startup pitch decks with optimistic projections, this was my first fiction since high school.Writing fiction was hard. I couldn’t rely on historical happenings and real-world personalities to guide me. I worried that people would dislike my work. Visions of unsubscribes filled my head as I ploddingly invented characters and dialogue.But I had to go for it….because that’s what I do now. I listen to invitations from the

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25:03

When AI Joins Your ELT

The Workaround by Bob Gilbreath Podcast ·

2025/04/02

“I’ve gotta tell you about this AI experiment we tried…”My old friend, Dave, dropped this on me just as we sat down to catch up over drinks in Las Vegas last week.He proceeded to share a jaw-dropping story of what happened when he invited an AI tool into his Executive Leadership Team meeting.Thankfully he gave me permission to share the saga—with several disguises to protect his company and his job.It was a wild ride with a potential lesson for all of us: By showing us humans at our worst, AI might

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19:40

Don't Pick Brains with a Shovel

The Workaround by Bob Gilbreath Podcast ·

2025/03/26

I’ve met with +300 people in each of the past two years.Many of these meetings involved requests for advice…and one trend stands out: The more specific people are in the questions they ask, the better the perspective I can provide.It’s a lesson that my new friend Jodi exemplified when she used ChatGPT to get the basics before we met.Listen to get the full story, tips for diving deeper, and a potential best use case of combining Human and Artificial Intelligence… This is a public episode. If you

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75:19

Lessons on Coaching People

The Workaround by Bob Gilbreath Podcast ·

2025/03/19

I’m excited to share the next podcast episode in my series of conversations with interesting people on topics where business and life intersect.My discussion partner this week, Meredith Meyer, is CEO and Lead Consultant of Infinite Potential, LLC, where she provides strategy and talent consulting services. I first met Meredith over 20 years ago, when we were both assistant brand managers on Tide at Procter & Gamble.Since then, she has spent a career moving from marketing and brand roles to people

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18:02

Leaders Must Not Be Held Hostage

The Workaround by Bob Gilbreath Podcast ·

2025/03/12

Almost every company, of nearly any size, has at least one employee who makes life miserable for everyone around them.We all know they are a problem—up to and including the CEO—yet nothing is done about their behavior. It’s like we’re all being held hostage…I was one of those leaders who let such a problem fester.But I finally overcame my fears and did the right thing.I hope this story motivates you to move faster when the toxic employee arrives at your company…or are they already there, and you’re

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21:49

Don't Create Art Unless You Care

The Workaround by Bob Gilbreath Podcast ·

2025/03/05

“You should create content”This is becoming the go-to advice for college job seekers, small business owners, and mid-career layoff victims.But it’s not for everyone…And if you don’t love your work, it won’t be great and won’t lead to your heart’s desire.Read, listen, or watch if you dare to fall in love with the creative process. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit behearty.substack.com

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30:00

How to Max your Earnout

The Workaround by Bob Gilbreath Podcast ·

2025/02/26

Recently, I had the chance to join John Warrillow on his podcast, Built to Sell. He’s the best in the business at pulling stories and success tips from sellers.In preparing for my discussion with John, I wondered what I could bring to the table that would be different than the other 479 guests he has spoken with.But I kept thinking back to a surprising consistency I’ve heard in John’s interviews:Most earnouts don’t work out—and that’s a shame.I’ve been fortunate on the other side. Nothing was easy,

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13:17

What Have You Built that Lasts?

The Workaround by Bob Gilbreath Podcast ·

2025/02/19

I’ll bet there’s a German or Japanese word for the sudden pop of a long-forgotten, meaningful memory that suddenly comes back like a strike of lightning.I had one of those “memory pops” last week when reading Paul Fisher’s post, “You Can Learn Anything from Anyone.” In it, Paul shares the story of a steelworker who was proud to point at a skyscraper and tell his children that he was responsible for placing the beam on the 45th floor.It reminded me of going into marketing many years ago, in part for

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110 results

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