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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

61:45

What Fatherhood and Founderhood Have in Common

The Workaround by Bob Gilbreath Podcast ·

2024/09/25

This is a guest post by my friend Paul Koop, a father who recently founded his first software startup.What started with a text exchange led to Paul taking me up on the idea of sharing his early impressions of the startup journey—and its similarity with early parenthood.A key theme: You’re never really “ready.”Check out Paul’s post. As a bonus, in this podcast version, we have a sit-down conversation that I’m sure you’ll enjoy. This is a public episode. If you would like to discuss this with other

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15:56

Only Invest in Character

The Workaround by Bob Gilbreath Podcast ·

2024/09/18

As a startup founder, advisor, mentor, and investor, I’ve seen thousands of early-stage pitch decks. Sometimes, there is a slide listing the team members, usually at the end.But any decent investor knows that the quality of the founding team is what you’re betting on with the first few checks.What’s missing is, by far, the more important: character.In this post, I share how investors of time and money—all of us—can better evaluate the character of the people we work with.With better assessment, we

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35:44

The Doors that Close Open Others

The Workaround by Bob Gilbreath Podcast ·

2024/09/11

I challenge you to think up a good outcome in your life that didn’t happen after a failure.That’s the story of Jess Shuman and her decision to launch Revelin, a Revenue Operations consultancy.I’m thrilled to announce our backing of Jess within Fleet and share how she got started.After reading the post, Jess joined me to discuss the story behind it. I know you’ll find her inspiring! This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes,

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16:02

Thank the Champions

The Workaround by Bob Gilbreath Podcast ·

2024/09/04

We don’t celebrate business success enough today, and we certainly don’t give enough thanks to the heroes who face headwinds and take arrows in the back by leading change within the enterprise.Books about innovation call them Innovators and Early Adopters, but those aren’t strong enough words. They are Champions—because it takes a heroic, even illogical, drive to make things happen within corporate processes that block them at every turn.Today, I share the story of one of many Champions who have

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17:07

Chasing Happiness Kills Company Culture

The Workaround by Bob Gilbreath Podcast ·

2024/08/28

“They created monsters”My new friend “Nate” said that when he described the giant tech company that bought his startup.In a culture of massive entitlement, it’s hard to get people to do productive work together without begging or bribing them.Most of us work outside the Big Tech world, but many of us have friends there. And when you get them to open up, they’ll admit that a sickness is pervading their corporate campuses.Too much junk food—or too much easy money and lavish benefits—can make companies

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16:21

How a Company Motto Affects Change

The Workaround by Bob Gilbreath Podcast ·

2024/08/21

Company mottos tend to get a bad rap today. We may think of Google’s “Don’t be evil” or Facebook’s “Move fast and break things.” The former has done a lot of evil lately. The latter officially quashed this motto once it had a billion members and quarterly profit numbers to hit.However, a motto can have tremendous value when these words are a natural extension of a focused, motivating business strategy. And it might make your life more joyful.My pod today is the proof. I tell the story of Bridge

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17:51

Don't Follow Mentors, Seek Signposts

The Workaround by Bob Gilbreath Podcast ·

2024/08/14

I’ve never “followed a mentor.” But there are countless people, living and dead, who have shared a scrap of useful advice that helped me at the moment and has stuck with me over time. Their words literally have reshaped my mind and made me what I am today.Here, I share one example—from a professor who first taught me that a handful of words can change your life. You’ll see his words and impact still living through me, his daughter, and the countless people we both have been signposts for in our own

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17:31

The Question is the Answer

The Workaround by Bob Gilbreath Podcast ·

2024/08/07

Last week I was a guest speaker at my friend Drew’s sales team offsite.I had to come up with a novel angle to share since I’ve never been a full-time commission-earning salesperson before!But I have one secret: I love to study people.This interest led me to marketing and then startups. Throughout, I’ve kept a keen curiosity about people. This curiosity helps me understand what is valuable to customers, which ultimately helps me close the sale.This week, I share some stories and question examples

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19:40

Work Around Dumb Rules

The Workaround by Bob Gilbreath Podcast ·

2024/07/31

Life hacking, time hacking, attention hacking, marketing hacking, and kitchen hacking. It seems we’re all hackers now.But there’s not enough talk of Bureaucracy Hacking, which I’ll define here as “How to be successful in your job when your company puts up unnecessary barriers.”In today’s piece, I tell stories from both Star Trek and my job with the Tide brand to make the point that some rules are made to be broken.In the process of breaking them, you learn a lot about yourself, which ultimately

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17:26

Diversify Your Mental Portfolio

The Workaround by Bob Gilbreath Podcast ·

2024/07/24

You can have enormous success in life and still be unfulfilled.You can build tremendous personal wealth and still be unfulfilled.Successful, wealthy people can struggle—like the rest of us—when they fill up on just one thing: Their careers.This is a lesson from Devin Martin, an executive coach who helps hard-charging business leaders discover lifestyle integrity. I recently found his work through the Talking Billions podcast.Several of Devin’s clients are investors. Ironically, these investors know

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18:26

Without Context, You’re Killing Us

The Workaround by Bob Gilbreath Podcast ·

2024/07/17

Great leaders are like artists.They pay attention to details and aim to move people through inspiration.While the artist must spend countless hours mastering a craft, you, dear leader, need only practice the Golden Rule.Let’s talk about context.I might seem to be making a big deal out of a little thing. But details are the tells of a leader’s true character. If we fail our people here, we are likely failing them—and our businesses—in much more significant ways.Today, I share a story about getting a

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15:48

BEST OF: Social Resolution-Only Positive Vibes

The Workaround by Bob Gilbreath Podcast ·

2024/07/10

Nearly four years ago, I resolved to share only “positive vibes” on social media. In this episode, I share how I’ve done.Many of us are re-evaluating our relationship with social media, and the big platforms continue to change their models and algorithms.Overall, social media is becoming, well, just media. I hope to bring this “positive vibe” mentality to all my real-life social interactions.Friends, please keep me on track! This is a public episode. If you would like to discuss this with other

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20:30

Mind on your Money, Time and Freedom

The Workaround by Bob Gilbreath Podcast ·

2024/07/03

Last week, I wrote about time management and better managing one's mind. But I left out a whole bunch of stuff...including The SECOND Rule of Fight Club.(this is one we can actually talk about)Here in Part Two, I will share ways to improve your life by making better daily decisions about time, money, and freedom.I start with the basic, tactical choices and ladder up to big-picture strategy with a personal story from my childhood that still drives me today… This is a public episode. If you would like

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21:21

Time Management is Mind Management

The Workaround by Bob Gilbreath Podcast ·

2024/06/26

If the “Time Management” meme were a stock, it would be neck and neck with Nvidia right now.Ironically, we have more free time than ever in recorded history, but it sure doesn’t feel that way.That’s because our minds still work with old programming that can’t compute the infinite options and infinitesimal threats.So, we’ve got to use better mind management for better time management.In this post, I share five ways I’ve reprogrammed myself to use time better and stress less. This is a public episode

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20:32

Fair Pay for CEOs

The Workaround by Bob Gilbreath Podcast ·

2024/06/19

CEO pay is in the news this week, and there's plenty of clickbait meant to shock you with the numbers.But no one talks about what it's like being a CEO negotiating compensation, especially in the startup world.So, I'm sharing my experience here.If you're a Founder/CEO, I hope my story can arm you to negotiate.And while you won't feel bad for public company CEOs pulling in millions, you might understand their perspective a bit more. This is a public episode. If you would like to discuss this with

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22:53

Business Leadership is a Call to Serve

The Workaround by Bob Gilbreath Podcast ·

2024/06/12

Despite all the posts and books on Leadership, many companies are led by people who don't get it.Maybe we need to go back 2,000 years to the writings of Stoicm, Christianity, Buddhism, and Judaism. Or we can study how the concepts of leaders and followers emerged as a key to our success as a species.I believe we need to consider Leadership as something "Holy" and "Awesome" in both the amazing and frightening meanings of these words.This week, I talk about the Call to Serve as a leader and suggest

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20:39

What's It REALLY Going to Take to Win?

The Workaround by Bob Gilbreath Podcast ·

2024/06/05

The more I learn about myself and the world, the more I realize that most learning from repeatedly getting kicked in the a**.Even when we are on the verge of success, an X-factor can keep us glued to the silver medal platform.Today, I share a story of leading Business Development at a creative agency and learning that playing to our strengths was the biggest barrier to winning.“What’s it going to take to win?” is a concept I’ve carried with me through multiple startups and countless client pitches

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14:55

Using Feedback Forcing Functions

The Workaround by Bob Gilbreath Podcast ·

2024/05/30

Let’s be honest. No one “loves” to give feedback…However, the need for feedback is high in small, high-growth startups. Our roles constantly change, so traditional job descriptions and performance measures are mostly meaningless.With more employees, forging relationships becomes harder. Remote work makes getting to know each other more challenging.So, the question was posed to me: How can we maintain the culture of feedback that is a strength today? My answer: You’ve got to force it with functions

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16:48

How to Quiet the Voice of Doubt

The Workaround by Bob Gilbreath Podcast ·

2024/05/23

“This voice in my head says I’m not good enough….”A friend told me this when we met for coffee last week. Her gut and heart were ready to make the leap, and she did the math to ensure her family finances weren’t at risk.Yet this little voice—inside her own head—decided to be a jerk.We all have these voices. They helped us stay alive in dangerous times, but today, they get in our way.So, I’m getting a little philosophical this week to share some insights on these voices and how to manage them.After

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14:06

In-Person is a 10x

The Workaround by Bob Gilbreath Podcast ·

2024/05/15

Last week, I attended a small conference in a beautiful setting. But I was THRILLED to spend most of the time in a small conference room.Thanks to Pip Coburn and his team, I had the opportunity to hang with fellow business and life geeks.Among many takeaways, it reminded me of the magic of being in person with people. I come away re-energized and just, well, happy.I’ll bet you feel the same.This week I share the story of this realization, and some tips for making the most of our limited but special

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