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

I’m working on two of my own startups right now. And this morning I caught myself doing the exact thing I'd flag in about four seconds if a client did it.

With Predictable, I started charging almost from day one. With ReplyLoop, I'm charging nothing. Zero. And I'd told myself there was a good reason for the difference. There was a reason. It just wasn't the one I'd been telling myself.

Let me back up.

I spend most of my week coaching founders through the early stuff. Finding the first customer, the first ten, figuring out who actually wants the thing. Maybe ten of them at any given time. So I think about this question constantly, just usually about other people's companies. It's a lot easier to see clearly when it isn't your own.

On Tuesday I was on a call with a founder I'm coaching, and they're in a spot that made me wince a little. Their client rolled the software out to an entire engineering org. Not a pilot, not a team. The whole org, which is not small. Great news, on the surface. Except now my client is stuck doing the most uncomfortable dance in all of software. Do we ask for money? Do we not ask for money? How do we bring it up without it being weird?

They gave it away to prove the value. Now the value is sitting in front of a hundred-some engineers and the invoice is nowhere. And the longer it runs free, the harder that conversation gets, because asking now feels like changing the deal.

I got off that call and went back to my own two companies, and the contrast hit me.

Predictable AI is the younger of the two. But the value creation is obvious. You run it, you get a thing you clearly needed, the line from "used it" to "this was worth it" is short and straight. ReplyLoop is different. It's workflow software. The path to saving someone real time is genuinely there, I'm sure of it. But to get there, you have to adopt a new email program. That's a real ask. You're changing where someone lives all day.

So here's the story I told myself. I can't charge for ReplyLoop yet, because I can't prove the value yet, and it feels wrong to charge for something I haven't proven. Wait until it's obvious, then turn on pricing. Responsible. Patient. Founder-friendly. Everything you're supposed to do.

Then I looked at the usage.

Because here's the part that broke my own logic. At zero dollars, the usage isn't good either. If "can't prove value, so don't charge" were the real constraint, then free access should at least get people in the door using it. It doesn't. And I finally understood why.

Free doesn't hurt.

If the thing costs nothing, then not using it costs nothing. There's no pain in letting it sit in a tab you never open. Nobody on the team has to defend the line item, because there is no line item. The whole point of pricing isn't just that I collect money. It's that a price creates a small, healthy amount of pain that makes someone actually decide. Use it or stop paying for it. Free removes the decision entirely, and a thing nobody has to decide about is a thing nobody uses.

So the mistake I'm making with ReplyLoop, and the mistake I'm not making with Predictable, has almost nothing to do with pricing strategy. By not charging, I quietly removed the one force that gets a person to open the thing on a Tuesday when they're busy and tired and could just keep using their old inbox. I took away the cost of ignoring me.

Now, the honest part. I didn't arrive at charging for Predictable through some clean strategic insight. It started as necessity. Credits. I'm spending real money on the services running underneath that product, and I needed to be made whole. So I turned on pricing from the start because I had to, not because I'd figured anything out. I'm not quite breaking even yet, but I'm close. Maybe this month.

Two reasons I charged for Predictable, then. One was the obvious value. The other was that I simply could not afford not to.

But the accident buried in there is the actual lesson. Charging didn't wait for proof. Charging produced the behaviour that creates the proof. People who pay show up. They use it, they complain about it, they tell me what's broken, they tell me what they'd pay more for. That's the loop that proves value. Free never starts the loop.

Which brings me back to the founder on Tuesday, the one with a hundred engineers and no invoice. I don't think they have a pricing problem. I think they have a sequencing problem. The money conversation isn't awkward because asking for money is inherently hard. It's awkward because they waited until the value was fully delivered for free, and now the ask lands like a penalty instead of a price. You're not pricing a product anymore. You're taking something away.

Charge earlier and it's a completely different conversation. A price, asked early, is just a question. It asks the customer one thing. Is this worth it to you? And you want that answer while it's still cheap to act on, while you can still change the product, change the pitch, change who you're even selling to. You do not want to find out the answer is no after you've handed a hundred engineers a free habit.

I'm not saying charge for vapour. I'm not saying slap a price on something broken and call it discipline. ReplyLoop still has real work to do before I feel good about asking. But "I'll charge once I've proven it" turns out to be a trap, because free is the thing standing between me and the proof. The price is part of the experiment, not the reward at the end of it.

So I'm turning it on. Probably small, probably with the design partners first, probably awkwardly. But on.

If you've got something out there in the wild right now, sitting free in someone's account because you're waiting until you've earned the right to charge, here's the question I'd sit with. Are you protecting your customer from a price, or are you protecting yourself from the answer?

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.

It will help you build a repeatable way to find customers without losing your weekends (or your soul).

Order now and you'll unlock a stack of exclusive bonuses I actually use with my consulting clients: Email me the receipt and I’ll share the resources.

Email me your receipt and I’ll share the resources.