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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

18:48

A CEO One-on-One with Everyone

The Workaround by Bob Gilbreath Podcast ·

2025/11/19

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 to a CEO role at a fast-growing, venture-backed startup.And if there were just one tactic I wish everyone

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12:29

Dying to Live a Long-Game and Why This Idea Never Works

The Workaround by Bob Gilbreath Podcast ·

2025/11/12

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 Tools2. It’s a LONG GAME3. Dying to Live: The Lou Marchetti Story Relevant links:Yancey Strickler’s LONG GAME: https://substack.com/@ideaspace/note/c-170687378Entrepreneurship is a Marathon: https://theworkaround.substack.com/p/entrepreneurship-is-a-marathonEntrepreneurship Burns Your Ego:

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16:55

Want Good Government? Hit the Highway

The Workaround by Bob Gilbreath Podcast ·

2025/11/05

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 figure it out and end up with something that works for us. Until it doesn’t again.Perhaps one way to help us

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69:47

Lessons from +100 Founders with Dave Rubinstein

The Workaround by Bob Gilbreath Podcast ·

2025/10/29

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 met roaming the halls of our large mutual client, Procter & Gamble. Dave spent his early career in a range of

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26:50

It's Not F-You, It's F-Me

The Workaround by Bob Gilbreath Podcast ·

2025/10/22

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 crappy jobs. You know: “F-You, Money.”I think F-You is too negative. I’d rather focus on the more critical

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10:04

Lesser-Known Job Search Tips, Every Award is...

The Workaround by Bob Gilbreath Podcast ·

2025/10/15

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 Tips2. Every Award is Political3. A Leadership Lesson from HockeyRelevant links:Bob’s posts about job searching: https://theworkaround.substack.com/t/job-searchingWhen Patrick Roy traded himself during a game: https://www.youtube.com/watch?v=nLxmJrpMSh8Schedule Office Hours with Bob:

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80:56

Creating the Career of Your Dreams with Peter Williams

The Workaround by Bob Gilbreath Podcast ·

2025/10/08

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 hit on a bunch of interesting topics, including:- How he ended up becoming an entrepreneur-

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16:35

Artwork is Your Mirror

The Workaround by Bob Gilbreath Podcast ·

2025/10/01

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 additional bonus for Paid subscribers!Schedule Office Hours with Bob:

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26:16

When Purpose Becomes Prison

The Workaround by Bob Gilbreath Podcast ·

2025/09/24

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 money. Together, this could add up to a job that doesn’t have to be crazy and one that we could look back

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35:06

Our Conscience, What We Sell, and Who We Sell To

The Workaround by Bob Gilbreath Podcast ·

2025/09/17

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 this.Morals and ethics seem more like politics and religion today—topics that people don’t want to touch for

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22:57

Embracing Bad Bosses and B******t Jobs

The Workaround by Bob Gilbreath Podcast ·

2025/09/10

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 completely wrong.In this case: What if it’s all…right? What if bad bosses and b******t jobs have a purpose in

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21:56

Breaking Down "It's Just Business"

The Workaround by Bob Gilbreath Podcast ·

2025/09/03

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, and soul—they commit less.People are struggling everywhere in life—always have, always will. But when we

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24:05

Build Your Career with Turnarounds

The Workaround by Bob Gilbreath Podcast ·

2025/08/27

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.Why? Because turning around iconic brands almost always comes from simply running a playbook that has been

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29:50

Share this with your Job-Searching Kids

The Workaround by Bob Gilbreath Podcast ·

2025/08/21

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’ve taken her and others through.It’s tough out there, with more people applying for fewer entry-level

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81:09

The Trail Provides

The Workaround by Bob Gilbreath Podcast ·

2025/08/13

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 me for a fun and insightful conversation.Marty has seen and done a lot in life and touched many people in

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40:00

Following Glitches in the Matrix

The Workaround by Bob Gilbreath Podcast ·

2025/08/06

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 “normal reality” and found something more profound in life, through exploring my mind.My intent is for

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29:12

Pause Now or Pay Later

The Workaround by Bob Gilbreath Podcast ·

2025/07/30

“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 should have.It took me four years of grinding through the challenges of building that next startup

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78:28

Fatherhood and Startuphood

The Workaround by Bob Gilbreath Podcast ·

2025/07/23

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 children, the host of three podcasts, and the biggest fanboy of Andor you’ll ever meet.We first met as

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20:07

Stop Talking, Start Trying

The Workaround by Bob Gilbreath Podcast ·

2025/07/16

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 everyone is available again. Maybe by Q4.But in the other 1% of those meetings, an individual or small

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33:17

My Problem with Personality Tests

The Workaround by Bob Gilbreath Podcast ·

2025/07/09

We humans love personality tests.We keep doing these tests, searching for…something. We spend a significant amount of money on them and are increasingly subjecting our employees to them.But why? Is it working? Could there be a better path?I found something that works much better for me. It’s also free and represents a model that you can use to change your personality for the better.SelfStages ChatGPT assessment tool: https://chatgpt.com/g/g-686ae2a5255081919dc82bf761ae0ad6-selfstagesIntroduction to

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110 results

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