Hey! First, a quick primer since this is Issue #1.
I felt compelled to write this newsletter because 98% of business advice I read comes from 1 of 3 places:
Gurus who've never actually built anything real. They sell frameworks and courses based on theory they've never pressure-tested.
Executives who haven't gotten their hands dirty in years. They'll tell you what the org chart should look like but has no clue how AI has changed structure.
One-hit CEOs who scaled one company one time—and now tell everyone to do exactly what they did, regardless of market, industry, or timing.
What's missing is the operator perspective….
The Story Starts Here
Ten years ago, I left corporate America. I was Director of Marketing Strategy at a $5B company (annual revenue, not valuation). It was safe. Comfortable. Private jets. New company cars and credit card. Golden handcuffs. Going nowhere interesting. It was truly a good run.
I'm a masochist, so I left my 6-figure salary and relocated my family cross-country to take a job at a scrappy Austin startup doing $2M a year, working out of a closet at WeWork. A company that would eventually become a darling in the publishing industry, one of Austin's "Best Places to Work," and scale past $25M.
But that's not how it started.
It started with me as employee #12—their first marketing hire. Over 5 years, I became CMO and 1 of 4 executives running the company. Then I went on to be a CMO and COO and several other major, founder-led brands.
I’ve been in the room when founders made decisions that doubled revenue in a quarter. I’ve been in the room when they made decisions that nearly destroyed everything they built.
This newsletter is about both.
The wins and the disasters. The calls that worked and the ones that blew up. I’ll tell you what I saw, what I learned, and where I got it wrong too.
Let’s get into it.
Here's a pattern I've seen more times than I can count:
In the early days, the founder is the glue. They hold everything together. Every decision, every relationship, every system—it all runs through them. And it works. It has to work, because there's nobody else.
But here's what nobody tells you about glue: it's sticky in both directions.
The same thing that holds the company together starts holding everyone back. The team can't move without touching the founder first. People wait for approval instead of executing. Good hires leave because they're stuck—unable to actually do the job they were hired for.
The founder's response? "I can't find good people." Or: "My team can't execute without me."
But the team isn't the problem. The glue is.
The founder built the company by being indispensable. Now being indispensable is what's killing it. The only way forward is to unstick—to let the team operate without being bound to the founder on every decision.
Most founders can't do it. Their identity is fused to being the glue.
I watched this play out in real-time at Scribe Media.
Tucker Max—yes, that Tucker Max, the "I Hope They Serve Beer in Hell" guy—co-founded the company. Turns out the same guy who wrote about his drunk adventures could also spot a massive gap in the publishing industry. In the early days, he was exactly what the company needed: a visionary who could see a market gap, build something to fill it, and will it into existence through sheer force of personality.
The company took off. Revenue climbed. The team grew.
And Tucker started drowning.
He said it himself at a company offsite when someone asked what he was afraid of:
"I'm afraid I'm not the CEO this company needs. I'm afraid I'm not going to be good enough to lead this company where it can go."
Here's what was actually happening beneath the surface:
Tucker was a world-class founder. Incredible at seeing problems, finding solutions, getting a company off the ground. But founding a company and scaling a company require completely different skill sets.
He was being pushed beyond his level of competence. Instead of admitting it fully, he kept grinding. Kept trying to be the hero. Kept attaching his identity and worthiness to holding the CEO title.
The company didn't have a hiring problem or a team problem. It had a founder who couldn't let go of being the center of everything—not because he was selfish, but because his ego had fused with the role.
Here's where it gets interesting.
Tucker met JeVon McCormick, a seasoned executive who'd scaled companies before. JeVon started advising informally, and within weeks it was obvious—JeVon was the CEO the company needed.
But when JeVon offered to join, he gave Tucker an out:
"What if I came on as President and COO? You can stay CEO."
This was the moment of truth.
Tucker could have taken the title, let JeVon do the actual work, and preserved his ego. Nobody outside the company would have known.
But Tucker called it what it was: "a ridiculous fraud."
He stepped aside. Made JeVon the CEO and Tucker refocused entirely on what he was actually best at—marketing and culture.
What Actually Changed
The moment Tucker got out of the way, everything unlocked.
JeVon didn't just take over—he built the structure the company needed to scale. He hired a COO. He brought me on to run marketing. He brought in a finance lead who actually knew how to manage cash and margins.
For the first time, the company had real operators in real seats—people who could own their functions completely, without waiting for founder approval on every decision.
Tucker? He went back to what he was genuinely great at. He built the media machine. He shaped the culture. He became the face of the brand. And he stopped trying to be something he wasn't.
The result? In Tucker's words: "Almost immediately, everything in the company that was messed up turned around."
For a while.
Tucker made the right call stepping aside. But the story doesn't end there—and the lesson I learned about what happens when you start choosing your own ego over data (and your leadership team) almost broke me. That's a story for a future issue.
Here's what most founders get wrong when they finally admit they need help:
They don't actually let go.
They hire a COO or President. They keep the CEO title. They tell everyone they're "stepping back to focus on vision." And then they create a power vacuum where nobody can actually lead.
I've watched this play out multiple times. The founder brings in an operator—someone capable of running the whole thing—but keeps one hand on the wheel. They second-guess decisions. They override strategy in the name of "founder intuition." They say they've let go, but everyone in the company knows who's really in charge.
The operator can't operate. The team doesn't know who to follow. And the founder wonders why things aren't getting better.
What Tucker did was different.
He didn't hire someone to report to him. He gave up the title entirely. CEO, not COO, not President. Full reins—strategy, hiring, financials, everything. He got out of the way completely so the right people could do what they were hired to do.
That's the only way companies actually scale: right people in right seats, with real authority to execute.
Most founders can't make that call. Not because they're bad people, but because their identity is fused to the role. Letting go of the title feels like admitting they failed.
But holding on is what actually kills the company.
Right people in right seats—with real authority. That's it. That's the whole game.
Everything else is just founders convincing themselves they're indispensable.
How was this week’s issue?
What happens when you do let go—but hand the keys to the wrong person. See you next Sunday.
How Can I Help You?
Hit reply and let me know. This email list is still small (this is issue #1), so reply while I still can read and respond to every email.
Onward—
Chris Piper
The Growth Operator