Why the Relationships You Invest in Matter More Than the One You Just Cashed Out Of (Transmission #347)
WRITTEN BY: BEN WRIGHT
Seeing the Friend’s Net Worth article stopped me mid-scroll. In the interview where Trevor Noah told Simon Sinek about being asked "what's your dream?" – Noah's answer wasn't about fame or money. It was this:
"I wish there was a top ten list for somebody who has a friend's net worth." Not the financial net worth of your friends. The richness of your friendships." - Trevor Noah
Drew Meyers took that idea and ran with it. He made the case that leaders with deep, strong friendships are better leaders than those without them. That professional relationships, no matter how valuable, are rarely raw and unfiltered. That as you get older, the circle of people who really know you gets smaller — and that's not a problem to solve. It's a feature. You don't need fifty surface-level connections. You need three to five people who've seen you at your worst and your best, and who tell you the truth anyway.
That article hit the same week I'd had dinner at my house with a group of post-exit founders. Ten of us around a table, no agenda, no pitch decks. And what happened was exactly what Drew was describing — but I'd never had language for it until I read his words.
I've Changed How I Think About Exits
A few weeks ago, I hosted a dinner for founders in the Post Exit Founders community here in Colorado. Some had sold their companies. Some were still figuring out what "after" looks like. One was three months past his exit and hadn't told most of his friends yet because he didn't know how to explain what he was feeling.
Nobody talked about deal terms. Nobody talked about valuations. The conversation went to the places that founders almost never go publicly — identity, loss, the strange grief of achieving something you worked toward for a decade and then waking up the next day with nothing on your calendar. The relief and the emptiness that show up at the same time.
It happened because we were there — in person, around a table, with nowhere else to be.
That's the part I keep coming back to. Forced presence. Forced in the way that the mountains force you to be present when you're at 11,000 feet and your lungs are burning. Forced in the way that sitting across from someone for three hours with no phones forces you to actually listen. Put yourself in situations where you can't escape, and something real happens.
Why Founders Are Uniquely Bad at Presence
Here's what I've noticed after 25 years of building companies and two exits of my own: founders are trained to sacrifice friendships. Not intentionally. But the math of startup life makes it almost inevitable.
You cancel on friends because a meeting came up. You skip the weekend trip because there's a product launch. You tell yourself you'll catch up later — after this round closes, after this quarter, after this exit. And the people who love you understand, because that's what good friends do. They give you grace. But grace without reciprocity eventually becomes distance.
Simon Sinek nailed this in his conversation with Trevor Noah. He pointed out that there are entire industries devoted to helping people with diet, exercise, and marriage — but not friendship. No one teaches you how to be a good friend. No one measures it. No one holds you accountable to it. And for founders, who are measured on literally everything else — revenue, growth rate, burn rate, NPS — the one thing that actually sustains you through the hard parts goes completely untracked.
Drew put it simply:
"It doesn't take thirty or fifty surface level friends to provide the support you need to navigate life's ups and downs. It takes three to five 'best' friends."
What Changes After an Exit
When you sell your company, something strange happens to your relationships. The professional connections that filled your calendar — your co-founders, your investors, your executive team — slowly recede. Not because anyone did anything wrong. Because the structure that held those relationships together is gone. The shared mission evaporated. You're no longer in the trenches together.
And you're left with whoever is still standing.
For a lot of founders I've talked to, that moment is clarifying in a painful way. They realize they spent a decade building a company and neglected the relationships that exist outside of it. Their spouse is exhausted. Their old friends have moved on. Their kids grew up while they were on calls.
But here's the other side of that: the founders who come through transitions well — the ones who find purpose again, who build something meaningful after the exit — almost always point to the same thing.
Not a framework. Not a coach. Not a book. A friend.
One person who looked them in the eye and said, "I see you. This is hard. And you're going to be okay."
Trevor Noah said something in that interview that has been rattling around in my head ever since: the abandoning or ignoring of friendships has affected romantic relationships, because people have shifted all the expectation, support, and love they once got from a community of friends onto one person. One spouse can't be your therapist, your co-founder, your best friend, your cheerleader, and your truth-teller all at once. That's not a marriage. That's a hostage situation.
Forced Presence: The Argument for Getting Away Together
The best conversations I've had in the last six months haven't happened on Zoom calls or at networking events. They've happened at altitude. On trails. Around fires. At my kitchen table with a bottle of wine and nowhere to be the next morning.
There's something about physical shared experience — actual effort, actual discomfort, actual beauty — that shortcuts the posturing and gets people to the real stuff faster. You can't maintain a persona when you're gasping for air on a switchback. You can't stay in "CEO mode" when you're watching the sun set over a valley and someone next to you quietly says, "I don't know who I am without my company."
Drew and I have been talking about this for a while now. He's seen it in GEM, where the most valuable moments happen not at conferences but at intimate gatherings where founders can be honest. I've seen it in my work with post-exit founders through Peak Adventures, where three days in the mountains produces more clarity than three months of journaling.
We're building something together this August — a Peer Passage Weekend for GEM 1500 founders in Northern California (or those willing to travel). Twelve founders, three days, and the explicit goal of doing what Drew described: creating the conditions where deep friendship can actually form. Not networking. Not "building your brand." Just being in a room — or on a trail — with people who get it.
Measuring Your Friend's Net Worth
I don't have a formula for this either. But I've been asking myself a version of the question Drew posed, and I think every founder should:
How many people in your life right now would drop everything if you called and said "I need you"?
Not "I need an introduction" or "I need advice on my cap table." Just: I need you.
If the answer is zero, that's not a personal failure. It's a design problem. You built a life that optimized for output and forgot to build the infrastructure for input. The good news is that friendships, like companies, can be built intentionally. But they require the same things that founders are often worst at: vulnerability, consistency, and showing up when there's no obvious ROI.
The founders I know who are thriving after their exits — truly thriving, not just “keeping busy” — have invested as deliberately in their friendships as they once invested in their cap tables. They've prioritized the people who knew them before the title, who will know them after it, and who care about them independent of what they're building.
That's your friend's net worth. And it might be the most important number you never track.
PS: If you're a founder navigating a transition and want to be in rooms where this kind of conversation happens, reach out to Drew or me.