It was a cold Saturday about a month after I exited my company. I was working in the yard, lost in thought about how strange it was to have been so completely invested in something for so long, and then to have it all just—poof!—disappear.

Selling your company means you won, in a way, but the psychological “end” of the process doesn’t arrive quickly. I have no scientific data on this, but after talking to hundreds of entrepreneurs, CEOs, and owners who’ve successfully exited their businesses, I’d say it takes about six months to really unwind, calm down, step back, and become yourself again.

It had only been a month for me at that point, but I’d already had a big revelation in my journey towards the next arc of my career and life: I’d learned that I had a lot of “deal friends,” and that I needed some real ones.

Real friends matter. A lot.

This real friends versus deal friends concept comes from the book From Strength to Strength by Arthur C. Brooks.  As a hustler, striver, achiever, and people pleaser himself, Brooks discusses true happiness in a context we as business leaders understand, and explores what happens when you are what you do. You got yourself to where you are, and your strength comes from that position, power, and achievement. But where does your strength come from once that starts to decline, or when you are supposed to hand it to the next generation?

I always thought I wasn’t defined by my occupation or position. It only became clear how wrong I was once I’d worked my way out of a job.

As it turned out, I had no real friends. I discovered that fact as I reached out to former work colleagues about new business ideas, or just to grab lunch and catch up. It turned out that they were all really busy working on all the important stuff that you do when you are working. Without a platform to help each other do “deals,” that value of our “friendship” was diminished. I don’t write that as judgment, but truth.

We need deal friends. I love my deal friends. Where I went wrong was thinking they were my real friends.

So what is a real friend, anyway?

Brooks goes on to define friendships via a ladder developed by Aristotle (yes, we’re being ultra intelligencia today).


Deal Friends

At the bottom tier are friendships rooted in utility—transactional alliances where mutual benefit drives the relationship. While not inherently negative, such connections lack depth and enduring emotional bonds.


Joy-Centered Friends

This tier thrives on pleasure, established through shared enjoyment of qualities like humor, entertainment, attractiveness, or intelligence. While surpassing utility-based friendships, they still retain an instrumental essence.


Real Friends

At this level, bonds flourish in a shared appreciation for something virtuous and meaningful beyond individual interests. Whether fueled by a joint passion for a social cause or a shared religious belief, these connections transcend instrumentality, reflecting intrinsic value and a mutual commitment to each other's well-being.


Friendships can be a blend of all of these and move up and down the ladder with time.

What I was pondering while working on the yard that day was how I had a whole bucket full of deal friends, a handful of joy-centered friends and, if I’m being totally honest, no real friends outside my wife and family. Ug. I was lonely because of it.

What I wanted were some real friends. Someone to share the journey with, the burdens and rough spots, good and bad, expertise, experience, vision, and values.

It’s another reason why I locked arms with my partner, Drew, in Acumen. I figured out that deal friends can become real friends. I just didn’t have time or energy to figure out where or how. I’m a typical guy – those things don’t come easy. I needed more deals to get to the reals.

What about you? Do you have real friends? (Note: you can’t count your spouse or kids.)

As CEOs and owners of companies, it’s already lonely at the top. Your subordinates can’t be your real friends because you ultimately decide their fate. That doesn’t mean you don’t have authentic relationships at and through work, but you most likely aren’t going to call them late at night to lament an argument with your spouse or how you are struggling to balance keeping everything together at home and at the office.

Dude… who cares?!?!? I have my head down executing and growing my company. I don’t have time. I’ll have time for real friends once my kids leave the house and I’m ready to retire.

OK, you can do that. So tell me, how often do you feel that no one knows you?

Not feeling known is really lonely. I had the fortune to learn that early.

Without real friends, you will miss a giant piece of joy, happiness, connection, and health.

You work on your marriage and your business, so why not work on friendships?

Here’s your homework. Take 60 seconds right now and go through your friend lists. What circles do you roll in outside of work? How many real friends do you have? Whatever names you put down, text them right now and schedule a lunch. Get three coffees, lunches, dinners, pickleball or golf meet-ups scheduled with your REAL friends over the next quarter. They are worth working on.  

Don’t believe me on this? Watch this classic Ted Talk from Robert Waldinger on what makes a good life. And if you're looking for those real friends - hey, I know a pretty great community you can check out today.