Smart public investors seek uncommon insights about the CEOs of companies to make better buy, hold, and sell decisions.

Even smarter public investors look for diverse insights on what makes a great leader from other people who assess leaders for a living, such as executive recruiters, pro sports psychologists, and startup founders like me! 

My friends Pip and Brynne recently invited me on their podcast to share a few things I’ve learned the hard way, and I’m taking this opportunity to outline my approach more fully here.

Whether you're trying to beat the market, picking a new head of sales, or deciding to work for a new manager, these are some proven ways to better assess the potential of people to lead us through the storms ahead.Coburn Ventures Podcast with Bob: https://open.spotify.com/episode/6dJu0C8Jyz3QWGGfwW1q4B?si=UwiDefJiRWWBtzmitnD-Ug

Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours

Fleet: https://fleetholdingco.com/

Revelin: https://www.revelinsolutions.com/

A2 Influence: https://www.a2influence.com/

“Funny how we have to come all the way out here to meet.”

That’s what my friend, Jack, says as we sit down for breakfast on a beautiful, sunny morning at an outdoor cafe across from the ocean.

His observation is one that we’ve all heard a hundred times in conferences around the world. It never gets old to hear this self-owning joke because it’s so true and so strange. But no one goes past the observation to break down why we meet out here more often and what that means.

This time I observed, and now I know…This is my story on why we let our guards down on the road, and what happens when we do.

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, Joe Hovde, is a data scientist who has worked in retail media, the venture capital industry, and now the podcast+broadcast business at Spotify.

We worked at the same company for a few months years ago, but never met until I became addicted to his Substack, Residual Thoughts. Over there, Joe shares “short, data-centric observations about business, technology, and psychology.” Recent topics have ranged from an analysis of the fast salad industry to the use of first names in interviews to the optimal time to see a celebrity comedian at The Comedy Cellar.

What I love about Joe is that he plays the game of business well, but, more importantly, he’s very interested in watching how the game works and why it works the way it does.

For our discussion, I asked him to serve up a topic on his mind. And, true to form, he suggested a doozy…“Why Does Business Media Evolve Toward the Spiritual?”

Recently, a brilliant young founder came to me with a startup idea. In this case, “young” = high school. Junior year.

Instead of judging his idea or spouting off a lifetime of advice, I told him the cautionary tale of another young founder who rose to great heights with potential, yet eventually lost it all.

I followed this story for over a decade, and I’m still learning from it. Now it’s your turn.Adam Mastrioanni’s “The Bluetooth Test and other keyholes to the soul.” https://www.experimental-history.com/p/the-bluetooth-test-and-other-keyholes

Schedule Office Hours with Bob: https://calendly.com/bob-gilbreath/bob-gilbreath-office-hours

Fleet: https://fleetholdingco.com/

Revelin: https://www.revelinsolutions.com/

A2 Influence: https://www.a2influence.com/

One of the interesting things about being an entrepreneur is discovering how many other people would like to follow in your footsteps—and are hungry for advice.

Years ago, I would fill a half-hour conversation with my assessment of the idea, keys to success, and watchouts.

However, I’ve finally realized that my evaluation of an idea is essentially meaningless. I’ve seen so many “great ideas” of my own die an ugly death, and frequently been surprised when products I thought were dumb ended up as massive hits.

While I don’t know whether an idea will work or not, I do know what it’s like to be an entrepreneur—and an Idea Person. It’s a rare gift…that can turn into a curse.

I’ve wasted years of my life on bad ideas that once got me excited.

Now, when people bring an idea to me, I try to help them see themselves in the mirror. This is my little speech, and my story…

Twenty-seven years ago this month, one of my first managers, Ann, shared something with me that changed my career and life for the better…

In coaching me on how to work with my agency, she said: “They don’t work for you, you work for them.”

It blew my mind at the time, but eventually it made sense. I used it to great success and continued to find new ways to be a servant leader throughout my career.

I’ll bet you can similarly rattle off a phrase or two that made a big difference in your work+life. But only now do I understand why I was able to listen back then, and how wise words can take hold in us today.

When we let the walls of our ego—our defenses—come down, the most valuable truth eventually finds us.

I wasn’t planning on posting this week. The long Memorial Day weekend is coming up in the U.S., and I know from previous years that open, listen, watch, and engagement rates plummet starting now.

But about ten different synchronicities—including from people close to me—suggest that people are really struggling out there.

Welcome to the challenge of our generations.

It sucks, it’s not fair, it’s been going on too long, and it feels like we’re sacrificing our children to some golem of change—with no relief in sight.

We need something to believe in and something to do about it. I want to share what works for me. It might help you handle the stress, and maybe even convince you to be the tiny pair of butterfly wings that delivers positive change.

Do you know why people buy your company’s brand and category? Are you really sure?

Often we’re fooling ourselves…or at least not digging deep enough to understand how these crazy people called “customers” actually make decisions.

It takes lots of curiosity—and usually getting personally embedded in a business—to see how things really work.

Here I share the lesson I first learned from my friends on Downy—the product that’s really Love in a Bottle—then went on to practice myself on Mr. Clean Magic Eraser and in my advertising agency.

Digging into the real reasons people buy your product or service can unearth directions for innovation and differentiation. It can also highlight blind spots where customer retention is at risk.

And you just might use it to learn more about yourself along the way.

Is there anything in the business world more celebrated than an IPO?

After many years of skill, luck, and grinding, your company name goes up in lights—with its own ticker symbol—and people worldwide can own a piece of the magic you and your team made.1

Of course, a lot of cash comes along with it, too. Some access it before others, of course…

An IPO is a game-changer for a company’s founders, investors, employees, and countless stakeholders who helped them get there.

But the game of company-building changes dramatically the day after that bell rings. For most, it is the first day of the end of the success story.

I think it’s time to re-examine the actual value of going public, especially for founders who aim to build something that lasts.

This piece is the result of months of marinating, which made me see my ignorance and a need to confess my sins.

My discussion partner this week, Marc Stoiber, is a Founder, Consultant, and Strategist who (re)invents leading brands for a living.

I first got to work with Marc when he was Executive Creative Director for the Grey advertising agency. Together, our teams turned around the iconic Mr. Clean brand.

Marc told me he was building a one-person strategy+creative agency…with the help of an army of AIs. That stopped me in my tracks—and I just had to get the rest of the conversation on the record.

Click below to hear his story about using AI as a creative wingman, looking at the future of work through an augmentation lens, and embracing our inner cluelessness.