Bob Gilbreath

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

Author

Bob Gilbreath

Category

Technology

Podcast website

theworkaround.substack.com

Latest episode

Jul 8, 2026

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Episodes

Productive, But No Longer Paranoid 08.07.2026

Have you ever discovered that something you thought was a key to your success was actually wrong? Something that worked out in the end, but it took years to see how it created so much suffering along the way? An idea that you taught to many others, and maybe caused them pain and suffering? Well, I awoke to something like this in my own life last week. I realized a core “shortcut to success” I had...

The Best Brand Ethos You've Never Heard Of 01.07.2026

This is a short story about a word that touches millions of lives each day… Take a left instead of a right at the restrooms behind the sports bar at a certain vacation resort, and you will come across one of the most meaningful corporate messages I’ve ever seen: “We are all Heartists” Here’s why I love this—and why we all should create our own version for the companies we lead.   Relevant links: S...

Founder Lost and Self Found 24.06.2026

Sometimes, the best way to find yourself is to get a little lost. We can choose to let go of what’s comfortable, leave the map of expectations behind, and walk into the darkness—trusting that we can handle this. I’ve recently returned from such a trip. Traveling alone across six cities in two weeks, I found parts of me that had been hiding for 50 years. Among many revelations, I gained insights in...

A Higher Meaning of Company Vision 17.06.2026

I think one of the challenges of building company culture is that it feels so “big”. It’s not the stuff we’re taught in business school, and not what we practice enough for the muscle memory it takes to feel confident. Consultants must be brought in, and while they can be helpful, culture building mostly happens when they’ve left the building. But it doesn’t have to be as hard as we make it out to...

Sell Your Shares, See Your Clients, Stop Buying Stuff? 27.05.2026

It’s another Bob’s Bites , where every couple of weeks, I share a handful of short stories and lessons…Today: 1. Sell Your Shares—separating your money from your mind 2. “Clients went feral after COVID”—is this why client success has gotten harder? 3. What Happens When People Don’t Want More Stuff?—a preview of life to come?   Relevant links: Netflix Co-founder on why to sell your shares: https://...

To My Greatest Business and Life Partner 20.05.2026

I’ve got a list of hundreds of “true business stories with a life lesson” from my career. I think now’s a good time to tell a really special one. After all, it’s our 30th anniversary in a few days. Not long after I met Steph, I wanted her to be my life partner. I didn’t know I would be getting a priceless business partner in the process. This is the story of how her belief in me helped me believe...

Name the Change You're Making 13.05.2026

Businesses spend nearly $1 trillion each year on advertising their brands, taglines, and other handfuls of words in hopes that their customers remember something pleasant about them when it’s time to buy. Words are portable thoughts, after all. And the more memorable the words, the more likely the thoughts are to spread and stick. While advertising has been a well-known tool for millennia, very fe...

You're (No Longer) Dead to Me 06.05.2026

~Michael Prince was removed from the team. Alas, another sign of our times…^^^ Last week brought me two examples of someone leaving an organization and its leader pretending they never existed. No announcement. No clue what happened. Just a Teams message that they were removed. Of course, we all eventually figured it out by speaking with the person. Truth finds a way. This is one of the countless...

We Need More "Augusta Rules" 29.04.2026

Despite wars, inflation, and increasingly scarce jet fuel supplies, there will be another record year of travelers funneling into the world’s most wonderful places. These travelers are armed with their cell phones and determined to prove that they’ve been there, done that. If you insist on joining them, watch for sharp elbows and stay out of their selfie shot range. Oh, and expect the actual artwo...

The Social Norms That Build Business 22.04.2026

Please Be Kind, Rewind. It’s one of many phrases that define my Generation X. The request to rewind was meant to help the next customer get their returned tape faster and spare the poor worker the mind-numbing job of rewinding tapes all day. The kindness of strangers helped us secure a copy of Die Hard for the weekend. These memories came back as I noticed a more recent example of a company making...

Retiring Early with Scott Aaron 15.04.2026

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 ca...

Revealing My Alter Ego: The Sign Avenger 08.04.2026

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...

Know Your Non-financial Motivators 01.04.2026

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...

A Commission Cap is a Growth Cap 25.03.2026

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 g...

What Your Biography Says About Me 18.03.2026

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 w...

Who is They? This is Us 11.03.2026

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 warnin...

Buying from Friends, Read Speed, and Marker Management 04.03.2026

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/@jam...

I Crashed an Annual Offsite 25.02.2026

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...

Playing Business with Ryan Watson 18.02.2026

Ryan Watson has been my buddy in building startups since 2015. He’s also a partner at Upsourced Accounting, a financial advisory firm for over 100 creative agencies. In between, he’s a husband, father of three, and the most organized youth soccer coach in the Greater Dayton, Ohio region. I can’t think of anyone better to host on my 100th podcast episode! Every few months, Ryan and I have a private...

Seeing through Silence, Foaling Around, and What Would You Do? 11.02.2026

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...

Don't Serve the Sh*t Sandwich 04.02.2026

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 s...

True Leadership is Treating Others 28.01.2026

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 f...

Smile Through Pain and Why VCs Rarely Make Intros 21.01.2026

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 Compla...

Choosing Sides on the Coin of Complaint 19.01.2026

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 ge...

AI Predictions are Projections 14.01.2026

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 u...

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