Issue #61: The Seasons of Scaling

Behind every neat growth curve is a messier reality worth talking about.

From the outside, it always looks smooth.

The charts in board decks slope neatly up and to the right. Milestones get packaged into tidy press releases. The narrative is clean: “We’re scaling.”

Inside, it feels a lot different. Building a company isn’t a straight climb. It’s potholes, detours, days where you feel unstoppable, and days where you’re quietly wondering if you’re steering into a ditch.

That tension — between the story the outside world sees and the reality on the inside — is something I’ve been thinking about a lot lately. And the more time I spend in founder mode, the more I realize: smooth scaling is a myth. What actually happens is seasonal.

Scaling Is Messy by Design

There’s this collective desire for startups to look predictable:

• Investors want clean curves.

• Teams want clarity.

• Customers want to believe the product is always one step ahead.

• And founders (myself included) want to believe we’re in control.

But growth doesn’t show up neatly packaged. Every win comes bundled with new headaches.

You land a big customer, and your contracts grind through weeks of redlines.

You ship a new product, and the backlog of “plumbing work” jumps out immediately.

You expand the network, and suddenly you have to rethink coverage city-by-city.

Scaling doesn’t mean eliminating the mess. It means choosing the right mess.

The Work Nobody Celebrates

Some of the most important work we’ve done this year hasn’t been sexy.

Cleaning up billing systems and Stripe integrations.

Standardizing contracts so sales cycles don’t stall out.

Tightening expense policies so every dollar of burn actually extends runway.

Nobody outside the company claps for those things. But if you don’t fix them, they pile up. They become the kind of problems that eat you alive when you’re trying to grow.

The paradox is that from the outside, scaling looks like speed. From the inside, it often feels like slowing down to clean up the foundation. But that’s exactly what creates compounding later.

Startups Have Seasons

I used to think every month needed to feel like summer — full speed, nonstop momentum.

But that’s not how it works. Companies move in seasons:

• Spring: planting seeds, experimenting, optimism running high.

• Summer: sprinting, long days, maximizing momentum.

• Fall: harvesting wins — contracts, adoption, cultural breakthroughs.

• Winter: slower, quieter, sometimes uncomfortable — but essential for cleanup and recalibration.

You don’t get to skip winter. You don’t get to grow without resetting the soil.

And this applies to customers too. Not every broker is our ICP today. Some aren’t ready yet. Eventually they will be — the market’s heading that way. But right now, the smart thing is to focus on the ones who are. The ones already building cross-border into Mexico and Canada. That’s where the compounding starts.

Founder Energy Is Seasonal Too

What I didn’t expect is that my own energy mirrors these cycles.

There are stretches where I’m in sprint mode — carrying a ton of weight, pushing hard, setting the pace. And there are stretches where I need to pull back, regroup, and reset.

Earlier in my career, I thought the only answer was to push harder every single day. But when you treat every month like summer, you eventually burn out. Worse, the team burns out too.

Now I manage my energy more intentionally: carving out thinking time, leaning on my team during heavy cycles, and using the slower periods for reflection instead of chasing fake momentum.

Because founder energy sets the temperature. If I’m frantic, the team feels frantic. If I’m steady, the team feels steady.

Blitzscaling (and Why It’s Not Always the Answer)

I’ve heard a lot of people reference blitzscaling again lately. And look — I get it. There are moments when moving fast and setting fire to the playbook makes sense.

But deployed in the wrong season? Blitzscaling is a recipe for disaster.

If you haven’t cleaned up the fundamentals — billing, contracts, focus on the right customers — scaling faster just means your problems multiply faster. It’s like flooring the gas pedal when your tires are bald. You’re not speeding toward growth, you’re hydroplaning.

The right size team, serving the right customers, in the right season — that’s what lets you scale sustainably. Then when the timing’s right, you can step on the gas and know the wheels won’t fall off.

Steering Through the Messy Middle

The myth says if you grind hard enough, the line will eventually be perfectly up and to the right.

The reality is scaling feels like turbulence. Some days are smooth, some days are shaky. The only guarantee is that the ride won’t be steady.

The founder’s job isn’t to make the turbulence disappear. It’s to steer through it. To keep the company pointed in the right direction, with the right people and the right customers, even when the line wiggles.

Closing: Playing the Long Game

Smooth scaling is a myth. The reality is seasonal. Some seasons are fast and exciting. Some are slower and uncomfortable. All of them matter.

Building in public doesn’t mean sharing every detail. It means being honest about the mindset you need to survive the grind.

If you’re in a winter right now — cleaning up systems, sharpening focus, right-sizing your team — don’t mistake it for failure. It’s just one of the seasons of scaling.

And the real job? Making sure you still have enough energy left when spring comes. Because that’s when the next harvest is made possible.