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

Follow up tool update: I’m almost there. The tool is working but the quality of the opportunities it’s surfacing isn’t good enough to share yet. Stay tuned.

Internal prospecting tool: I use Clay a lot and found that I was doing the same things over and over again in it, which I find tedious and boring. So I built an internal tool for myself that gives me 80% of the power of Clay in 1% of the time. It’s not quite as good, but it’s soooo much faster. Ping me back if you’re interested and if enough people raise their hand, I’ll work on making it something others can use.

Onto the newsletter…

Picture this. You've been working with a customer for six weeks. They've onboarded their team to your product. They've given you feedback. They've sent you bug reports at 11pm. You've been on weekly calls. You've shipped fixes. Things are going great.

And then you have to bring up money.

It's like you've been dating for two months, you've already slept together, and now you're trying to figure out if you're, you know, a thing.

This is a common founder mistake that I see. You get so excited that someone is using your product that you forget to talk about pricing. You tell yourself you'll bring it up later, when the time feels right. You don't want to mess up the vibe.

The longer you wait, the weirder it gets. And by week six, you're stuck. Asking for money now feels like a bait and switch. Not asking for money means you're running a free service. Either way, you lose.

The fix is to seed the pricing conversation early. Like, on the very first call after they've seen the product. And the way you do it is something I call the pricing sensitivity bookend.

No judgement if you’re here. When I was bootstrapping Carb (selling the service based on the future tool) I had 10 customers that were all supposed to be paying me around $2k a month and I didn’t notice that I had forgot to ask them to pay until my accountant asked where all our money was… I had told them pricing, they signed the contract, but I never sent an invoice/payment link. Genius move right there.

Before you ask anything, you need to give the person permission to give you honest feedback. So you start with this:

"Hey, can I pick your brain on pricing? We haven't nailed down what we're going to charge yet, but I want to ask you a couple of questions, and I want you to know upfront that these aren't the actual prices. I just want your gut reaction."

That little preamble does a lot of work. You're not asking them to pay anything. You're not committing yourself to a number. You're just inviting them into the conversation. Most people are flattered to be asked.

If they're a current customer or someone you're already friendly with, add one more line: "And just so you know, I'm not going to use this against you later. I'm just trying to figure out where the market is."

That's the disarming part. They can be honest without worrying that you're going to come back and quote their answer at them.

Now you start with a price that's intentionally too high.

"If I told you this was a hundred bucks per user per month, would you hit me in the head with a hammer?"

Yes, the hammer thing is silly. That's the point. The silly framing keeps it from feeling like an actual offer. You're letting them know this is a thought experiment, not a quote.

Watch their face. This is the most important part of the whole exercise.

If they laugh and immediately say "yeah, no way," that's a snap rejection. They have a strong gut feel that the price is too high. Move on.

If they pause and make a slightly pained face, that's gold. That means they're actually thinking about it. They're running the math. They're imagining what it would have to do to be worth that. That's the look you want.

I'll give you an example from a long time ago. I was doing this exercise for Carb, and I had one prospect literally hang up the phone on me when I floated a high anchor. He thought I was actually trying to charge him that much. Lesson learned. Always make the question feel like a question, not an offer. The hammer joke exists for a reason.

Now you go the other way.

"Okay, what if I told you it was ten bucks per user per month? Would that feel cheap?"

You're checking the floor. If they say "yeah, that seems fine," ask why. Sometimes a price that's too low actually scares people. They wonder what they're getting for ten bucks. They worry it's not real software.

I had this exact conversation with a founder recently. He told me that ten bucks felt fine, but then said it might not set up the relationship well if we ever wanted to raise the price. That's incredibly useful information. It means twenty isn't just acceptable. It's smarter, because it leaves room.

Now, and only now, you tell them what you're actually thinking.

"What we're considering is twenty bucks per user per month. How does that sit with you?"

Watch the face again. If you've done the bookending right, twenty feels reasonable to them because they just told themselves a hundred was too high and ten was suspicious. You've built the goalposts, and now you're putting the ball right in the middle.

Once you've got their reaction, ask the follow-up question that turns this into a real conversation:

"What do we need to build for you to feel good about paying twenty bucks a month for this?"

This is the question that prints money. They'll either tell you the product is already there, in which case you've just qualified them. Or they'll tell you exactly what's missing, in which case you have a roadmap.

If you're talking to someone who's going to be one of your first ten customers, do not charge them full price. Give them a deal. Tell them you're giving them a deal. And tell them why.

"Hey, we know we're early. We know there's going to be some jank. We want you to be a part of shaping this thing, so we're going to take care of you on price. But the real number is going to be X."

This does two things. It sets the price expectation for later, when you raise it on them. And it gives them an accusation audit, which is a thing from Chris Voss in Never Split the Difference. You're acknowledging up front that the product isn't perfect, which makes it impossible for them to be surprised by it later. They walk in expecting dragons. When the dragons show up, they're not mad. They're just nodding along.

The trick is to make the deal contingent on something. A case study. A referral. Weekly feedback calls. You're not just being generous. You're trading.

A case study from a recognizable logo is worth a hundred grand to you in your next sales cycle. The two grand a year you're discounting them is a rounding error.

The pricing sensitivity bookend is not about getting the answer right on the first try. It's about making sure you're never six weeks deep into a relationship before you've talked about money. It's about making the awkward conversation small and early instead of big and late.

When was the last time you brought up pricing on a first call? Try it, you might just find it makes everything easier.

Collin

PS - here comes an ad for my book, I stole the idea from Sahil. It felt like the right thing to add to the end of each newsletter.

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