A Fit Check That Hit Home

One Insight

This week, something special happened.

For the first time, we brought all of our leadership teams together in one room. Black Kanyon. Our portfolio companies. People who are normally scattered across states, buildings, and businesses, sitting side by side, working on the same problems, pushing toward the same future.

As you’re reading this, many of us are probably traveling home, so this feels like the right moment to share something that’s been on my heart.

Six or so months ago, Peyton and I started having an uncomfortable conversation about my seat at Black Kanyon. Not about whether I belonged here, but about where I actually create the most value long term.

COO or CFO.

That might sound like a simple title discussion. It wasn’t.

I love the COO role.
I love the people.
I love the relationships.
I love being in the middle of the mess with leaders, helping them grow, coaching through hard moments, building trust, and pushing teams forward.

Those relationships matter deeply to me. They always will.

Real relationships aren’t clean or easy. We say the wrong things sometimes. We disappoint each other. We have hard conversations. But that friction is what forges something stronger. That’s what makes it real, and real relationships are one of the things I value most.

At the same time, I love the CFO role for a completely different reason.

It is where I’m most naturally myself.

The strategy.

The numbers. The deal structure. The analysis.

That work doesn’t drain me, it focuses me. It’s where my mind locks in and where I can see three, five, ten moves ahead. It’s where I can best protect and grow the future of everything we’re building.

So what do you do when you love two things equally?

You get honest about why.

And when I really did that, something became clear.

A big part of why I wanted to stay in the COO seat wasn’t actually about what was best for Black Kanyon.

It was about me.

It was about the challenge pushing me.
It was about the relationships I didn’t want to let go of.
It was about the identity of being responsible for most of the people.
It was about the quiet validation that comes with being at the center.

It’s okay to care about those things. Leadership is knowing when to let them go.

Because leadership is not about holding onto the seat you love.
Leadership is about putting the right person in the right seat, even when that decision affects you personally.

And that is exactly what happened here.

We now have someone stepping into this role who is exactly what this company, and all our companies, need to move to the next level. I am deeply confident in that. Watching who he is, how he leads, and how he connects with people made it clear to me that this was the right decision for Black Kanyon and for our portfolio companies. The right decision for the people and those relationships I value so deeply.

That clarity changed everything. It also reminded me of something important.

Change like this can feel unsettling. Keeping things the way they are feels safe. Even when we know a better version exists, the unknown can make us hesitate. That’s normal.

But leadership isn’t about eliminating uncertainty. It’s about being willing to step into it, one day at a time, and figure it out as we go.

If staying in the COO role meant holding these organizations back from what they could become, that wouldn’t fair to the people who work here. And it doesn’t align with what we say we believe.

My responsibility is to be in the seat where I create the most value so that others can be in the seats where they create the most value. That’s how strong companies are built.

That’s the real Fit Check.

Not “What do I enjoy?”
Not “Where do I feel important?”

But “Am I doing what is best for the mission, even when it’s uncomfortable?”

As we head home from this summit, I hope this story sticks with you. Not as a message about titles or org charts, but as a reminder of what we’re really trying to build here.

A place where we put the mission first.
A place where we trust each other enough to make hard calls.
A place where we keep choosing what will make us all better, not just what keeps us comfortable.

That’s how we will build something exceptional together.

-EJ Drake

One Story

Early in Amazon’s history, Jeff Bezos was involved in everything.

Every decision ran through him.

Every hire mattered.

Every problem landed on his desk.

That level of control was part of why Amazon survived. But it was also what would have eventually limited it.

As the company began to grow, Bezos realized something uncomfortable. Amazon didn’t need him to be the best operator in the room anymore. It needed him to build a system that could scale beyond him.

So he started doing something that was personally difficult.

He hired people who were better than him at running things.

He gave away control of fulfillment, finance, and operations to leaders who could take those functions further than he ever could. That meant fewer decisions, less visibility, and less day-to-day influence. It also meant Amazon could become something far bigger than any one person.

Years later, Bezos said the hardest part wasn’t the complexity of the business. It was learning to let go.

Growth almost always requires trade. Letting go of what you’re good at, letting go of what feels safe, and trusting the right people to take something you love further than you could on your own.

One Question

Strong teams are built when people understand how they’re wired and choose to lead from that place with honesty and intention. When we do that, we create space for others to do their best work too.

So take a moment to reflect:

How might leaning into your strengths and owning your weaknesses help your team win next?