To My Greatest Business and Life Partner

Founder Lost and Self Found

Sometimes, the best way to find yourself is to get a little lost. We can choose to let go of what’s comfortable, leave the map of expectations behind, and walk into the darkness—trusting that we can handle this. I’ve recently returned from such a trip. Traveling alone across six cities in two weeks, I found parts of me that had been hiding for 50 years. Among many revelations, I gained insights into what really, really drove me to become an entrepreneur, and why selling my startup hit me so hard. It took joining the company of strangers in a strange land, ego naked and afraid, to uncover and encounter fears that were holding me back. This post is going beyond my usual business stories. I’m taking a leap of faith that, by sharing who I am and how I’ve changed, I might inspire a few of you to uncover something new about yourself, too.   Relevant links: Meghan French Dunbar on Joy Trips: https://meghanfrenchdunbar.substack.com/p/i-just-want-to-remember-what-it-feels [https://meghanfrenchdunbar.substack.com/p/i-just-want-to-remember-what-it-feels] Douglas Rushkoff’s Retreat: https://rushkoff.substack.com/p/just-die [https://rushkoff.substack.com/p/just-die] Heather Havrilesky on Attuning to Social Cues: https://www.ask-polly.com/p/attuning-to-social-cues-can-be-empowering [https://www.ask-polly.com/p/attuning-to-social-cues-can-be-empowering] Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours [https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours] Fleet: https://fleetholdingco.com/ [https://fleetholdingco.com/] 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 [https://theworkaround.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

A Higher Meaning of Company Vision

I think one of the challenges of building company culture is that it feels so “big”. It’s not the stuff we’re taught in business school, and not what we practice enough for the muscle memory it takes to feel confident. Consultants must be brought in, and while they can be helpful, culture building mostly happens when they’ve left the building. But it doesn’t have to be as hard as we make it out to be. Sometimes, just one silly idea, practiced with an open heart, can break the ice that freezes the flow between employees. And it’s the employees who create the culture, mostly when the CEO is not around [https://hbr.org/2012/05/culture-takes-over-when-the-ce]. This is the story of one little practice that worked for me, and later revealed something fundamental about human connection in my life. Relevant links: Tim Freke on Substack: https://www.youtube.com/user/timfreke [https://www.youtube.com/user/timfreke] Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours [https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours] Fleet: https://fleetholdingco.com/ [https://fleetholdingco.com/] 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 [https://theworkaround.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Sell Your Shares, See Your Clients, Stop Buying Stuff?

It’s another Bob’s Bites, where every couple of weeks, I share a handful of short stories and lessons…Today: 1. Sell Your Shares—separating your money from your mind 2. “Clients went feral after COVID”—is this why client success has gotten harder? 3. What Happens When People Don’t Want More Stuff?—a preview of life to come?   Relevant links: Netflix Co-founder on why to sell your shares: https://marcrandolph.substack.com/p/betting-everything-on-your-company [https://marcrandolph.substack.com/p/betting-everything-on-your-company] Why Japanese People Don't "Want" Things Anymore”: https://substack.com/@jameslucasit/note/c-202186114 [https://substack.com/@jameslucasit/note/c-202186114] Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours [https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours] Fleet: https://fleetholdingco.com/ [https://fleetholdingco.com/] 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 [https://theworkaround.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

To My Greatest Business and Life Partner

I’ve got a list of hundreds of “true business stories with a life lesson” from my career. I think now’s a good time to tell a really special one. After all, it’s our 30th anniversary in a few days. Not long after I met Steph, I wanted her to be my life partner. I didn’t know I would be getting a priceless business partner in the process. This is the story of how her belief in me helped me believe in myself and go on to have the career of my dreams. Relevant links: Bob’s Substack: https://theworkaround.substack.com/ [https://theworkaround.substack.com/] Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours [https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours] Fleet: https://fleetholdingco.com/ [https://fleetholdingco.com/] 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 [https://theworkaround.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Name the Change You're Making

Businesses spend nearly $1 trillion each year on advertising their brands, taglines, and other handfuls of words in hopes that their customers remember something pleasant about them when it’s time to buy. Words are portable thoughts, after all. And the more memorable the words, the more likely the thoughts are to spread and stick. While advertising has been a well-known tool for millennia, very few leaders similarly understand the power of their words within their businesses. By carefully crafting and promoting the words that communicate your strategic choices and areas of focus among employees, you can lead thousands of them to harmonize in ways that drive remarkable success. Relevant links: Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours [https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours] Fleet: https://fleetholdingco.com/ [https://fleetholdingco.com/] 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 [https://theworkaround.substack.com?utm_medium=podcast&utm_campaign=CTA_1]