The Workaround by Bob Gilbreath Podcast

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/...

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 excelle...

There’s a song from Sesame Street that I think of around this time of year. You know it, too, so sing it with me: Oh, who are the people in your neighborhood? In your neighborhood? In your neighborhood? Why do I think of this song this time of year? Because it’s the holidays, when our Postal and other Delivery People are very busy, and we see them daily in our neighborhoods. It’s a reminder to tha...

My conversations with friends increasingly include a disturbing topic: What are we going to do when s**t goes down? You know, like, when whatever disaster we expect to happen finally hits. I once felt this stress, and I know how insidious it is. And they are in good company. Many people in our country and in the world live daily in fear of disaster. I feel for the pain that my friends and so many...

It’s another Bob’s Bites , where every couple of weeks, I share a handful of quick stories and lessons that have been on my mind lately…Today: 1.     Choosing a Vendor? Pick a slate instead of a single winner 2.     Saving your next holiday dinner discussion by first re-stating another person’s position 3.     Two Founders, Two Bobs, One Podcast   Relevant links: Technocratic podcast with Bobby Ta...

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, Alice Turner, is a highly experienced Doula and Lamaze-certified childbirth educator who has supported more than 300 births. She has helped both women and men make childbirth a positive experience. She’s also a certified s...

None of us knows what to do when we become a CEO for the first time. We’ve got to learn these skills on our own. It’s a scary process! Unfortunately, these fears tend to swing leaders either into micromanaging or hiding themselves behind layers of management. We can do better than this. I write here each week to share real-life stories of what worked and didn’t from my career, which eventually led...

Welcome to another Bob’s Bites . Every couple of weeks, I share a handful of quick stories and lessons that have been on my mind lately…Today: 1.     Why Hasn’t It Worked?: Business Referral Tools 2.     It’s a LONG GAME 3.     Dying to Live: The Lou Marchetti Story   Relevant links: Yancey Strickler’s LONG GAME: https://substack.com/@ideaspace/note/c-170687378 Entrepreneurship is a Marathon: http...

It’s government shutdown season in the U.S. once again. Whatever side we’re on, we’re united in agreement that democracy doesn’t seem to be working for us. We deserve better. We’ve done better. This is not meant to be a political post. I refuse to whine, blame, or take sides. Democracy is the worst form of government— except for all the others . One way or another, I’m confident we’ll eventually f...

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, Dave Rubinstein , is the brains and energy behind 100 Founders , a new project aimed to help ensure Founders survive, thrive, and transition from Founder-led sales. Dave and I first collaborated twenty years ago, when we m...

A few billion people are trapped in some level of workplace hell. I mean, they must be trapped—or why would they stay in these jobs? The traps sure are elaborate: Paychecks, health insurance, stock options, annual bonuses, non-competes, peer pressure, economic worries, and fancy titles. But the potential for freedom is out there! Mostly, we long for a financial nest egg that would let us quit our...

A new idea is born: Bob’s Bites . Every couple of weeks, I’ll share a handful of quick stories and lessons that have been on my mind lately…Today: 1. Lesser-Known Job Search Tips 2. Every Award is Political 3. A Leadership Lesson from Hockey R elevant links: Bob’s posts about job searching: https://theworkaround.substack.com/t/job-searching When Patrick Roy traded himself during a game: https://ww...

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, Peter Williams , is the founder and CEO of Designerds, a creative-led agency based in the Bay Area, and Luna Park, a “skunk works” product development shop with some exciting consumer products now hitting the market. We hi...

It took me +50 years to realize that a piece of art hanging on a wall is not really about the colors, shapes, characters, or whoever’s signature is on it. It’s really about the artwork that each human subject creates in response to the object before them. This essay explores how everything in our lives can serve as a mirror of self-understanding. I’m also sharing an original song I created as an a...

Looking to escape bad bosses and soul-crushing companies? One common strategy is to seek mental safety and personal growth in a company with a mission—perhaps a nonprofit pursuing a noble cause, or a startup working to improve the environment or provide affordable education. Maybe a more meaningful company would attract like-minded believers, led by a progressive founder who cares about more than...

I’m pretty sure everyone reading these words has been part of a company that sells something. But have you ever thought about the ethics or morals of what you sell and who you sell to? Where is your line? How did you set it? What have you turned down and feel proud of? What have you done that still sits like a splinter in the back of your conscience? Oh, but we prefer not to discuss things like th...

Last week, I went on a rant about bad bosses and the rising gap between the commitment they demand and the commitment they are willing to make. It felt good to get it out…for about a day. Then something bothered me about what I wrote. So I started scratching at that itch… I pulled out an approach I use from time to time to examine beliefs—especially my own. I consider how this belief might be comp...

Twice in the past week, I heard the phrase “It’s just business” when telling their employees about layoffs. I now look forward to the day when AI takes over leadership roles in companies. Because not even a robot would use language this awful in telling a human being they are no longer wanted at their place of employment. As these leaders ask for more —not merely hours, but more of our mind, heart...

The world’s biggest brands can’t get a break lately. Late last year, both Nike and Starbucks brought in new CEOs after experiencing declines in share price and product sales. Panera did the same in January. Intel did it in March. Subway followed in July. Target is the latest iconic brand to show its CEO the door. While the challenges are massive, I would love to be one of these replacement CEOs. W...

Every month or so, a friend asks if I would be willing to meet with their son or daughter who is very early in their career in hopes that I might offer some helpful advice. This summer, my daughter asked the same, and I ended up putting together a “class” from what I’ve learned through hiring hundreds of people in my companies and running a recruiting business. Today, I’m sharing a summary of what...

I’m excited to share the next episode in my series of conversations with interesting people on topics where business and life intersect. This week is a double-double bonus…My good friend and entrepreneur, Marty Boyer, just finished the sale of his second company. He celebrated and reset himself by spending weeks alone on a hike. I persuaded him to share a guest post about his experience and join m...

Last week, I shared my story of learning the hard way—through five pivots in four years—that it was time to release the role of startup founder, stop wrestling with the universe, and figure out a new way of going with the flow. Nobody in the business world ever told me the kinds of stuff I’m going to share here, as directly as I’m going to share it. This is about how I peeked behind the curtain of...

“Don’t do anything for at least a year.” This is the most common advice that post-exit entrepreneurs share when they write their books or appear as guests on podcasts. They caution that there is a natural tendency to want to get back on the horse, to build something bigger and better, and keep the dream team working together. It’s the advice I give, too. The only problem? I didn’t follow it when I...

I’m excited to share the next episode in my series of conversations with interesting people on topics where business and life intersect. My discussion partner this week, Raman Sehgal , is a man of many interests. By day, he is the SVP, Head of Marketing for EDO , a leading, scaling platform measuring predictive behaviors driven by Convergent TV advertising. By night, he is the father of two young...

As you read these words, tens of millions of people are sitting in conference rooms or on Zoom calls discussing whether to do one thing or another. They work in startups, corporate gigs, not-for-profits, and government jobs. And 99% of these meetings will end with indecision. A task force will look at it. Consultants will be called. And, of course, a follow-up meeting will be scheduled as soon as...