The Most Dangerous Stage in Business.

Hey hey.

Happy Friday.

Right now, I’m sending this from the middle of a field in Tennessee.

It’s year ten of Bonnaroo with my brother and some of our best friends, a trip we’ve made every summer since before CROSSNET, before The Founders Club, before all of it. A few days of the best music (King Gizzard!), camping in the mud, and memories with some of my favorite people in the world. And yes, if you’ve been following along on socials, you’d know that I did find my matcha. (If you haven’t been, @chrismeade on IG, follow along for the ride.)

Bonnaroo is one of my favorite places on Earth. And every time I’m here, it reminds me how important it is to build things you can step away from, and how lucky I am to get to come back to work I genuinely care about.

Before I dive back into the chaos of a 4-day music festival, I wanted to send you this: 

A real take on the most dangerous stage I’ve ever seen in business: the one that doesn’t look like danger at all. When things feel “fine.” Revenue’s steady. Team’s stable. Growth is good-enough.

And yet, something’s off. Let’s talk about it, and more importantly, how to fix it.

What “Fine” Looks Like (and Why It’s So Dangerous)

Let’s be clear. “Fine” doesn’t mean your business is failing. It means:

  • You’re profitable, but plateaued.

  • Team’s executing but not innovating.

  • Revenue is solid, but stale.

  • There’s no crisis, but also no clarity on what’s next.

The danger of “fine” is that it tricks your brain into thinking you can coast. You get reactive, not proactive. You optimize for today, not for scale.And most dangerously? You stop asking the kind of questions that create real leverage.

This is when founders start:

  • Delegating without context

  • Avoiding hard re-orgs or pivots

  • Overweighting what worked last year

  • Sleeping on strategy because ops are “under control”

And all of that leads to a slow, silent plateau. Not because of lack of talent, but because of lack of tension.

How to Spot When You’re Stuck in “Fine”

Here’s the thing: “Fine” is a feeling before it’s a fact. So if you’re wondering whether you’re in the danger zone, ask yourself:

  • Am I still thinking critically about how this scales, or just repeating what worked?

  • Do I have clarity on what the next version of this company looks like?

  • Are my best people being stretched and challenged, or just managed?

  • Am I avoiding the uncomfortable move, the hire, the fire, the price raise, because things are “okay”?

  • Am I innovating on the business or just in the weeds of the business?

If you’re nodding to more than one, you’re likely drifting into maintenance mode.

Why “Fine” Happens, Even to Great Founders

This stage usually shows up right after your first big wins. Maybe you hit $2M, $10M, or even $50M.

You’ve hired a team. Maybe raised capital. You’re not “figuring it out” anymore. That early pain is gone, but so is the urgency.

And here’s where it gets dangerous: You start optimizing for peace instead of performance.

And I get it. I’ve been there.

After CROSSNET started scaling, I found myself slowly pulling off the gas. Not intentionally, but because it felt good not to be in survival mode.

But here’s what I realized:

The companies that break out aren’t the ones that play it safe when things settle. They’re the ones who keep tension high even when things are stable.

That’s what separates your average founders from the high-performers.

How to Break Out of the “Fine” Trap

Build Friction Into Your Character

Create space every month to review what’s no longer working. Not what’s broken, but what’s stagnant.

Ask:

  • What used to be a growth engine that’s now just noise?

  • What are we maintaining that’s no longer mission-critical?

  • What do we assume is working, but haven’t measured?

Pressure Test Your Org Chart

One of the clearest signs of a “fine” business is a bloated org chart. Too many doers, not enough owners. Too much middle management. Too many yes-men.

Ask:

  • Who here is innovating, not just executing?

  • Who would I hire again today?

  • Where am I tolerating B+ performance out of loyalty?

Audit the Energy, Not Just the Output

This one’s personal. When things feel fine, founders tend to detach. Meetings are efficient, but uninspired. Projects are “moving,” but no one’s leading them.

Ask:

  • What’s actually exciting us right now?

  • What problems feel energizing?

  • Are we saying “yes” to stay busy or to stay bold?

Re-draw the Vision Map

Fine = foggy. Most founders hit this stage when the original vision is achieved, but no one has updated the playbook. 

At the beginning of the year, the Founders Club leadership sat down with a Big A** Calendar and mapped out the entirety of 2025. So crucial. Sessions like this are where you re-ask:

  • What does the next level look like?

  • What do I want this company to make possible, for me, my team, our customers?

  • Who’s already doing it? How are they thinking differently?

The Founders Who Beat “Fine” All Do This One Thing

They stay in rooms where the standard is higher than their comfort zone. Inside TFC, I’ve watched 7-9 figure founders light a fire under each other just by asking sharper questions.

Things like:

“What would you do differently if you started your company tomorrow?”
“What’s your biggest bottleneck, and are you the one reinforcing it?”
“If your team only worked 4 days/week, would anything break?”

The point? The founders who escape “fine” aren’t necessarily smarter. They’re just surrounded by higher standards, better questions, and faster feedback.

That’s what Founders Club was built for.

What to Do Next (Audit Your Business)

If you’re reading this and feeling that quiet anxiety, like maybe you’ve been in “fine” mode too long, good.

It means you care enough to fix it. Here’s what to do:

  • Block 90 minutes next week to audit where you’re coasting

  • Ask 3 key team members what they’d kill, keep, or change

  • Pick ONE friction point to lean into (pricing, ops, brand, etc.)

  • Set a “discomfort goal” for Q3 (something bold enough that it scares you a little)

  • Book a call with someone ahead of you to shortcut the guesswork

Optional, but game-changing:
Get around a group where the standard is higher than your own.

Final Thought

The goal of entrepreneurship isn’t “fine.” It’s not “coasting.” It’s not “managing well.” It’s building something that pulls the future toward you faster than anyone expects.

But that can’t happen if you’re asleep at the wheel. So if you’re feeling the drift?

Wake up. Lean back in. And ask the questions “fine” founders avoid.

Because good businesses don’t die from chaos. They die from comfort.

And you weren’t built to stay comfortable.

Have a great weekend,

Chris