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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

76:45

Lessons from First-Time CEOs

The Workaround by Bob Gilbreath Podcast ·

2025/02/12

There’s no certification course needed to become a CEO. One day, you find yourself in that position and must figure it out on your own. Everyone is waiting to see what you’ll do first.No pressure, of course…Everyone who has been in this role has a unique story to share. This week, I sat down with Rob Reinfeld, the Co-founder and CEO of A2 Influence, a content development agency that helps leading brands and retailers create and distribute authentic content at scale.We’ve been friends and business

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19:03

What are Eight Years of Your Life Worth?

The Workaround by Bob Gilbreath Podcast ·

2025/02/05

Lots of people I know are waiting for their exit.They don’t love their jobs and dream of doing something else with their lives. But the promise of life-changing money keeps them in their seats.Some are waiting for the IPO or their Private Equity owners to sell the company. Others wait for the options to vest or for the commission checks to be paid.I see and feel for their suffering—because I’ve been there. In total, across two acquisitions, I’ve spent eight years of my career waiting for a

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19:33

Five Phrases it Pays to Extinguish

The Workaround by Bob Gilbreath Podcast ·

2025/01/29

Life is full of little phrases that make us flinch…“We’re still waiting for our flight crew to arrive.”“Due to an accident overnight, the bridge is closed for repair until further notice.”“I saw something that concerns me, and I’d like to run more tests.”They bring immediate annoyance and the worrying prospect of more pain.Leading a business gives you many other opportunities to listen for and correct problems.It took me decades of work to compile the following list of phrases. Ignore them at your

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30:09

Entrepreneurship Burns Your Ego

The Workaround by Bob Gilbreath Podcast ·

2025/01/22

“I’d love to start a business, but I think my ego is holding me back from giving up my current position.”“I can’t share this idea until it’s perfect. My ego is getting in the way.”“I’m afraid this will fail, and I’ll look like an idiot in front of my peers. I guess it’s my ego again.”These quotes are a sample of what people said to me last month—just like the month before and the one before that.Each individual I spoke with is a strong, proven mid-career leader with a robust network. An

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63:47

Learning in an Era of Smartphones

The Workaround by Bob Gilbreath Podcast ·

2025/01/15

I’m excited to share the next podcast episode in my series of conversations with interesting people on topics where business and life intersect.Brynne Thompson is an investor, advisor, and all-around brilliant+kind person who helps startup founders and institutional investors figure out where the future is heading.We’ve had many such conversations over the years as fellow members of the Coburn Ventures community—so I knew she would deliver the good stuff.Our discussion topic revolves around how we

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19:27

The Art of Client Service: Your Company's Edition

The Workaround by Bob Gilbreath Podcast ·

2025/01/08

When we look back on a year, it’s hard to remember specific days. Meetings were attended, emails were sent, and clients were served. It’s all a big blur.But we do recall a handful of events—the big deal we sold, the massive problem we solved, the time the client yelled at us, and when our manager confided in us over drinks.We remember stories.Wouldn’t it be great if we could capture all of the meaningful stories from our work and put them down in writing—to share for others’ benefit and keep the

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15:44

The Dance of Meetings

The Workaround by Bob Gilbreath Podcast ·

2024/12/31

For the 2nd year, I reviewed my calendar to tally up the number of people I met. Survey says: 307 Meetings It’s down from 2023, when I was getting two new businesses off the ground. In 2024, I was a little more in-person and made more new friends than last year.But this was the year I began to see each meeting as a kind of dance—an opportunity to bond with another person and create something unique through conversation. As the year progressed, I dropped some awkwardness, let my partners take the

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85:06

5 Surprises from Startup Acquisitions

The Workaround by Bob Gilbreath Podcast ·

2024/12/18

Going through an acquisition comes with tons of pressure, fear, opportunity…and surprises.But making it through gives you more confidence for the next time and a desire to pay it forward for those who come after us.In that spirit, I sat down with my long-time business partner, Ryan Watson, to discuss the surprises we have experienced during M&A processes.Ryan and I led the acquisition of our influencer marketing company in 2018. Today, Ryan regularly advises his clients on both sides of the M&A

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18:44

My Seven Stages of Recovery From Betrayal

The Workaround by Bob Gilbreath Podcast ·

2024/12/11

If you’ve worked closely with people, pushing business boundaries long enough, you’ll have some drama, breakups, and maybe a betrayal. When you take your work seriously and own the business, everything about it is personal.My story today started with a close friendship, led to a close business partnership, and ended with a bombshell betrayal.There is much truth in recovery models, but they tend to lack specificity around betrayal and fail to detail what acceptance and integration look like over the

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18:23

Are you the Big Fish or Small Fry?

The Workaround by Bob Gilbreath Podcast ·

2024/12/04

My brand promise in this newsletter is to provide shortcuts to success. And today, I’m sharing a juicy one that I’ve learned across thirty years of buying and selling professional services:Make sure your business is important to the service provider you hire. And almost always, the size of the check you write—compared to other clients—is the measure of importance.Over on Substack, I tell the story of how I learned this the hard way—repeatedly—at my agency and share some tips for service business

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9:08

We are surrounded by people who care

The Workaround by Bob Gilbreath Podcast ·

2024/11/27

I wasn’t planning to write this week. But a tiny nothingness struck me that made me feel something special.It was just this broken sign…that someone sprayed with orange paint to help pedestrians avoid its danger.It doesn’t matter who specifically did it.All that matters is We Did It.We care.Despite our many faults and broken internal algorithms, we have this going for us—which is nice.I’m thankful for all of the little things we do to help each other counter the entropy in the universe.That ugly,

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58:02

"If you're in the people business, you're in the...

The Workaround by Bob Gilbreath Podcast ·

2024/11/20

Today, I share my podcast conversation with Mark Mears—an author, consultant, and enlightened leader.After a career in senior marketing roles such as Pizza Hut, McDonald’s, and The Cheesecake Factory, Mark turned a major disappointment into an opportunity to fully follow his calling.He shares inspiring messages about the best behavior of team leaders and provides insights on his shift from C-level VIP to consulting solopreneur. This is a public episode. If you would like to discuss this with other

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23:56

When the Big Competitor Sued My Startup

The Workaround by Bob Gilbreath Podcast ·

2024/11/13

No one starts a company expecting to be sued by their biggest competitor. Maybe we should…Almost no one publicly shares what it’s like to go through it when it happens. But today, I’m opening the vault to share my experience defending against a punch below the belt.Just push play to hear the whole story…And if you have a moment, please share this post with an entrepreneur you know. Small business owners need all the help they can get against competitors lacking honor. My story might come in handy

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51:39

The Right Business is Personal

The Workaround by Bob Gilbreath Podcast ·

2024/11/06

“Allergies are a secret plague to millions of people. We deserve to breathe, and we founded Wyndly to help you.”It's a pretty darn good elevator speech.Today, I share my podcast conversation with Aakash Shah, a first-time founder who is building a startup in an enlightened way. There are at least three reasons why I think you’re going to enjoy this episode:If you’re early in your career or thinking about launching your own business, Aakash shares a journey and tips that might help you get a head

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12:07

You Are Significant

The Workaround by Bob Gilbreath Podcast ·

2024/10/30

I’ve been sitting on a couple of posts that I am particularly excited about—but I’m stopping everything to share a story from a friend that motivates the hell out of me.There are jerk bosses, and there are really awful, horrible bosses. This is about the latter.Business philosopher Naval describes our purpose in life: “To reverse local entropy.” That’s a short and fancy way of saying: “The world is always going to s**t, so grab a shovel and do your part to improve it while you’re here.”Jerk bosses

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13:02

A Coat of Paint Can Make a Big Difference

The Workaround by Bob Gilbreath Podcast ·

2024/10/23

The biennial BLINK light show returned to Cincinnati last weekend. It’s a time when our city literally shines, and we are united in a love for the town and its creativity.The event reminded me of the time my team took the initiative to boost our startup culture by painting our office walls during a dark time.Whether it’s a struggling company or a city with challenges, investing to spruce things up is not necessarily painting over problems.Problems cannot be solved overnight and are often out of our

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64:28

Modern Leadership is All in the Mind

The Workaround by Bob Gilbreath Podcast ·

2024/10/16

Today I've got a special treat: a discussion with Evan LaPointe, a 5x company founder who is on a mission to help us bring a better mental game to the workplace. His current company, CORE Sciences, is a modern, science-driven way of training and coaching your team to be their best. We had a wide-ranging and fast-moving discussion about a new mental model for leadership. Some teasers from our conversation:“I served a 3.5-year sentence at Adobe.”“You can be the best”“Modern leadership is

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13:45

"Nobody Knows What They're Doing"

The Workaround by Bob Gilbreath Podcast ·

2024/10/15

Don't let your assumptions about others' greatness kick you in the ass.My story of the Big Agency pitch and learning that everyone is making things up as they go along. 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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18:52

Try Doing the Opposite

The Workaround by Bob Gilbreath Podcast ·

2024/10/09

Ever heard of The Costanza Principle? It’s another piece of genius from Seinfeld. As you might recall, it’s the realization that when every decision you make fails, the right path might be to do the opposite.I learned this the hard way in my first startup experience.We did everything our investors, peers, and industry stars said we should do—and we completely sh*t the bed.This is my story of learning an even more profound lesson in the writing process—that my Fear prevented me from seeing reality

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11:33

Neither There Nor Back Again

The Workaround by Bob Gilbreath Podcast ·

2024/10/02

Yes, I am a nerd. But I also care about inspiring entrepreneurs.After watching a promising founder give up on their dream before giving it a try, I thought about the stories that will now never be told.And I wondered...Where would we be without stories of the Hero’s Journey?So, this is a short sort of fan fiction—an alternative story of The Hobbit in which Bilbo refuses the call to adventure.Apologies to JRR, but perhaps an inspiration for you. This is a public episode. If you would like to discuss

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110 results

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