The Workaround by Bob Gilbreath Podcast

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 V...

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...

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 un...

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 in...

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...

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 sto...

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 th...

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-lev...

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 busine...

“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 thin...

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...

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...

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 conve...

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 theworkaround.substack.com

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 le...

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. A...

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 convers...

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 a...

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 pu...

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 corpor...

“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 pervadin...

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 str...

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 st...

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 cu...

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 a...