Recently, I had the chance to join John Warrillow on his podcast, Built to Sell. He’s the best in the business at pulling stories and success tips from sellers.

In preparing for my discussion with John, I wondered what I could bring to the table that would be different than the other 479 guests he has spoken with.

But I kept thinking back to a surprising consistency I’ve heard in John’s interviews:

Most earnouts don’t work out—and that’s a shame.

I’ve been fortunate on the other side. Nothing was easy, and we got lucky as hell. But each time I hear of others’ struggles, I wish I had a chance to share my experience with them beforehand.

So I sat down and tried to distill what I learned and screwed up in going through this twice.

Whether you hope to sell your company someday, are an employee at a company that goes through this, or are just curious, come with me for a peek behind the curtain at an interesting, under-reported corner of the business world…

I’ll bet there’s a German or Japanese word for the sudden pop of a long-forgotten, meaningful memory that suddenly comes back like a strike of lightning.

I had one of those “memory pops” last week when reading Paul Fisher’s post, “You Can Learn Anything from Anyone.” In it, Paul shares the story of a steelworker who was proud to point at a skyscraper and tell his children that he was responsible for placing the beam on the 45th floor.

It reminded me of going into marketing many years ago, in part for the chance to see the product of my work on thousands of store shelves.

Meaning is important, but it is different for everyone. Try a bunch of things until you find yours.

“Proof of impact” has been special for me. Maybe it can be for you, too.

Listen for more on how to make meaning this way.

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 partners for years, so I was curious to hear his impressions after completing his first year as CEO—and share some of my own memories in the process.

Whether you’ve been a CEO for years or aspire to be in that role someday, I’m sure you’ll uncover some valuable lessons—and enjoy a few laughs with us along the way.

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 check.

Neither case was “Rest and Vest”—we had to work our butts off to get those checks.

However, I learned that a painful journey can bring a reward more valuable than what hits your bank account. Here’s how…

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 peril…

“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 entrepreneurial path tempts them, and they could easily return to a traditional job if the leap doesn’t work out, but a voice in their heads blocks them.

Choosing the career path of an entrepreneur has forced me to understand and overcome my Ego. It has been a wild ride of two steps forward and one-and-a-half steps back.

You might choose to start a company someday. Or you may have no choice—forced into a freelance or contract assignment in a corporate environment that increasingly drives us to fend for ourselves. Either way, I’d like to share what your Ego is in for.

Despite the risk of making entrepreneurship seem an even scarier proposition, I hope to share an under-reported payoff that is more valuable than any financial windfall that may result.

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 can take advantage of all the information available at our fingertips without falling for the non-wisdom of the crowd—and driving ourselves crazy in the process.

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 lessons top-of-mind for ourselves?

Yes, it is great. I know because I did it. It helped turn our team around. I’m going to tell you the story of company storytelling and how you can start benefitting the same way today.

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 lead more often, and smiled more than ever.

I hope we get on each others’ dance cards in 2025!

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 process as a Partner at Upsourced Accounting, a group of future-focused financial strategists who provide digital accounting and CFO services to the creative industry.