Hello {{First name|Predictable Revenue community}},

Today is another anniversary of my entrepreneurial freedom day. The day I quit my job and started working for myself.

I wrote about the first 13 years last year, so instead of rehashing old ground, I want to use this one to look back on just the last 12 months.

They were strange months. It felt like the whole startup world was on a treadmill and some cruel trainer kept leaning on the "must go faster" button. I sat with founders as they shut their companies down. I watched others finally crack product market fit after years of grinding. And I felt the ground move under my own feet while I tried to build something new on top of it.

I learned a lot this year. But the lesson that actually stuck with me has nothing to do with this year. It's something I've been circling for 14 years and only recently said out loud.

I like small.

Let me back up, because that sounds simple and it wasn't.

I remember when Predictable Revenue hit 10 employees and the company finally felt real. Like an actual thing, not a thing I was pretending into existence. At 20 it felt hectic but exciting, the good kind of chaos. Then somewhere after 30, something quietly changed. There was a layer between me and the people on the frontline now. I didn't have the hours in the day to really know everyone anymore. I told myself that was just what growth felt like and I should be grateful for it.

At 50, I didn't like it. At 85, I was miserable.

It felt like someone was driving the company and nobody knew who. No matter what I did, we reacted too slowly. The message I thought I'd made obvious never quite reached the edges. I'd find two teams rowing in opposite directions and only catch it weeks after it mattered. I spent my days managing the company instead of building it, and I wasn't even good at the managing part.

Some of that was my own inexperience, and I won't pretend otherwise. Some of it is just what happens when any company gets bigger. And some of it is the gap nobody warns you about, the long stretch between $1m and $10m where you have the needs of a $10m company and the resources of a $1m one. That gap sits on your chest the entire climb. People tell me it lifts once you cross $10m. I wouldn't know. We made it to $5m ARR before the wheels came off.

Here's the thing I couldn't see at the time. I wasn't failing at being big. I just didn't want to be big.

I like knowing everyone. I like having a real connection to the people I work with, no matter what their job is. I like a flattish org where everyone's opinion gets respected, but not so respected that nothing ever gets decided. There's something about a small team doing big things that's just plain fun, and for years I treated that preference like a weakness I was supposed to grow out of. Real founders scale. Real founders hire. Real founders build the org chart. So I kept building it, right up until it broke me.

Which brings me to the one part of this year that genuinely feels new.

In 14 years, I've never had tools like the ones I have now. I can build a working prototype myself, badly, but working. I can run a customer development loop in days instead of months. The kind of work that used to require hiring two or three people now takes an afternoon and a clear head. I'm not exaggerating when I say I'm more productive today, alone, than I was with a team of ten a decade ago.

I used to assume the big companies would win the AI era. They have the data, the budgets, the distribution. And maybe they still will. But this year I watched up close how slowly the big ones actually move, and it isn't because the people inside them are slow. Most of them are sharp and they see it coming. It's the bureaucracy. The layers. The same layers that made me miserable at 85 people, except multiplied by a thousand. By the time a Salesforce or a HubSpot fully reorients around AI, a small team will have already figured out what the next version of the software even looks like.

That's the window. It won't stay open forever. But it'll be open long enough to matter.

So the optimist in me has started thinking about these tools differently. Not as a way to grow headcount faster, but as a way to stay small and still act big. To get the reach of a 50-person company without rebuilding the exact machine that wore me down the first time.

I want to be clear that this isn't a money thing. It isn't about maximizing profit per employee or squeezing more out of fewer people. It's about design. I spent 14 years, and more energy than I'd care to admit, just to earn the right to work for myself. It would be a little silly to do all of that and then not be intentional about the kind of company I actually want to work inside of.

Constraints breed creativity. Staying small is a constraint I'm choosing on purpose this time, instead of stumbling into it and then resenting it for five years.

Fourteen years in, I think that's the real shift. Not the tools, not the market, not even the hard lessons. Just finally knowing what I'm building, and why, and being honest about what I actually want it to feel like.

So here's what I'd ask you, wherever you are on your own roller coaster. Are you growing because you want to, or because you assume you're supposed to?

Collin

The Terrifying Art of Finding Customers is the playbook for founders who never planned to do sales but have to figure it out anyway. It pulls together 13+ years of building software startups, building outbound systems for hundreds of B2B startups, and more failed experiments than I'd care to admit, into a practical guide for finding your first 10, 100, and 1,000 customers.

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