It Takes Two Years

Collin Stewart
November 28, 2025

Hello Predictable Revenue community,

Book update: A huge thank you to Jason, Rick, Sean, Adam, Peter, and Hayk for leaving Amazon/Audible reviews this week. If you've read the book and found it helpful, a review makes a real difference. Get your copy of The Terrifying Art of Finding Customers today.

On to the newsletter…

I spent most of this week pissed off at myself.

Not because anything was going wrong, exactly. The book has sold over 350 copies in its first month. The reviews have been heartwarming and encouraging. The newsletter keeps growing. I’m making good progress on VC List.

But I caught myself doing that stupid founder thing where you know better but can't help yourself anyway: comparing my timeline to someone else's highlight reel and wondering why I'm not already there.

Then I watched Parker Conrad on Sequoia's The Long Strange Trip, and he said something that stopped me cold.

With Zenefits, they ground away for two full years with zero traction. Nothing. Then one day, something clicked, and suddenly they had a rocket ship. But those two years? Pure despair. Working your ass off and getting nothing back.

He was basically saying: don't start a company unless you're wired to enjoy that kind of punishment. Because two years of struggle is the minimum buy-in, not the exception.

That hit me because this newsletter is coming up on two years. And I just now, just now, feel like I've figured out the rhythm of how to produce something I’m not embarrassed by every week.

When I started Founder's Edition, I had no idea what I was doing. I just knew I wanted to document what I was learning, both for myself and for the founders I work with. I hoped it would help me sell books but I had no idea how.

So let me answer the question honestly: has it been worth it?

Is it a good use of my time? Absolutely yes.

This newsletter has become my business journal. Every week, I'm forced to process what I'm seeing in client calls, what I'm struggling with internally, and what ideas are connecting in new ways. It's made me sharper, more organized, and better at explaining concepts that used to just live as vague intuitions in my head.

Even if you took away every dollar it's generated, every client it's brought in, every book it’s helped sell, I'd still write it. The clarity alone is worth the time.

Has it brought revenue? Yes, kind of.

The newsletter was the biggest driver of book presales and it has indirectly brought in a few founder coaching clients. It's earned me podcast invitations and speaking opportunities. If I had to estimate, it's probably generated $100k in coaching revenue and maybe $10K in book sales.

Is that incredible? No. But if this were a go-to-market channel I was evaluating, would I keep investing in it? Probably. It's good enough to be worth doing.

Have I figured out the process? Finally, yes.

It took almost two years, but I've landed on a system that works. I keep Post-it notes all over my desk. Anytime I'm in a client call and struggling with something, or a new idea connects, I write it down. Same thing when I'm reading or listening to something and it sparks a thought.

From there, I've evolved through a few different writing methods:

Version 1: Sit down with a blank page and write every word myself. This took four hours per post and I'd get stuck constantly on phrasing.

Version 2: Write the crappy first draft, then use ChatGPT to help rephrase clunky sentences. This was faster but still fully manual.

Version 3 (current): Use transcripts from client calls where I've explained something in a new way or just a transcript of me talking to myself (like today), have ChatGPT write a summary, then pass the transcript and summary to Claude to write a first draft. From here I edit it manually, clean things up, and add in details or stories.

Funny side note, when I ran this through Claude, it deleted the mention of ChatGPT in my process 😂.

The final product is about 50% my words and 50% LLM phrasing, but 100% of the ideas and source content are mine. Usually this process takes 90 minutes. Sometimes it takes four hours because the AI slot machine gives me nothing useful and I have to write it manually. It’s not perfect, but it works.

Reality Check

Which brings me to the book.

Launching a book is almost identical to launching a startup. You need three things:

A gap in the market that actually exists
The ability to execute well on filling that gap
A way to get your creation in front of the people who need it most

All three have to be driven by the founder.

I tell every founder building an SDR team the same timeline: six months before you see anything real, 12 months before it's consistent, 24 months before it's worth it.

So why have I spent this week whining to myself about the book not exploding in popularity?

I know better. I teach this stuff. But the ego slips in anyway.

Here's the truth I had to remind myself of: outputs are a direct reflection of inputs.

When I step on the scale in the morning, I weigh exactly what I should given the food I've eaten and the exercise I've done. I can't complain about the number. I have to change the inputs.

Same with the book. Same with the newsletter. Same with VC List. Same with every new project.

And on expectations: jumping from unknown author to bestseller in a month is as realistic as expecting to lose 100 pounds in a day. But knowing that doesn't always stop the frustration.

What Actually Matters

The funny thing is, when I step back from the noise, the book is doing exactly what I hoped it would.

I've heard from a bunch of you who are reading it. You've shared stories about how something I screwed up helped you avoid the same mistake. That's been the most rewarding part, more than the money, more than the vanity metrics, more than getting invited to speak.

Knowing that my failures can help you make new mistakes instead of the same old ones? That feels like a real contribution.

But I still spent most of this week unhappy about sales numbers, review counts, and the fact that VC List isn’t farther along. Classic founder behaviour.

The Reminder You (and I) Needed

So here's what I'm taking away from this week:

The minimum buy-in for anything meaningful is two years of struggle. Not two years until success. Two years until you even know what you're doing. If you’re not willing to make that investment, don’t bother.

Focus on the inputs. If you want different outputs, change what you're putting in.

Manage your expectations. Progress is slower than you want and faster than you think, but only if you stay committed through the messy middle.

And if you're frustrated with where you are right now? You're not alone. I'm right there with you.

Collin

P.S. After reading this draft back, I couldn't help but notice the parallels to Stoicism. Seneca summed up the core tenets in his Moral Letters to Lucilius: control your perceptions, direct your actions accordingly, and willingly accept what is outside your control. Two thousand years later, still the best framework for staying sane as a founder.

P.P.S. There's another insight from the Parker Conrad interview worth sharing. Around the 23-minute mark, he talks about how he doesn't hire experts and abdicate responsibility. He needs to understand every core function at Rippling from first principles. I've tried the "hire an expert and let them run it" approach. It's never worked. Turns out it's not about delegation. It's about needing deep understanding before you can lead effectively. Here's the full interview if you want to watch.

P.P.P.S. Last one I promise. Here are the other book reviews from this week, if you’ve read the book and have a review, I’d love to hear from you. Pick up your copy today if you haven’t already.

Adam’s