People pay more than you think to fix a problem

My first version of Underway's message was built entirely around a moment: don't miss day one, imagine watching Jeff Bezos build Amazon from the actual footage, not a documentary made twenty years later from photos and memory. Nearly everyone I spoke to understood it and said it hit right. The trouble was it only worked on someone who happened to be standing at the very start of a new project, at the exact second they were thinking about it. That is a rare moment to catch someone in, and most people who saw the ads were not in it.

A business owner called Ryan signed up because the message hit at exactly the right second, he was starting an animation project. But then he asked me something that told me everything: could he also use it for his other, more mature business? That question should never have needed asking. If the positioning only speaks to day one, everyone with an existing business quietly assumes it is not for them, even when it obviously is.

So the pain point I was selling against was situational, not constant. People feel "I might miss recording the start of something new" only occasionally. They feel "I've put off documenting this for years and I regret it" almost permanently, every single day they do not film.

I rewrote the whole positioning around a pain point people feel always, not just on day one. The new message is roughly: you've missed it for the past five years, so start now, and Underway is the thing that does all the content work for you, you just have to sit there. It is a minor-sounding change in wording but a completely different emotional trigger, loss and regret you are already carrying, rather than a window you might be about to miss.

The effect was immediate. Sign up, sign up, sign up came in way quicker than before. I know this is my bread and butter, sales and marketing, but it still surprised me how much faster people moved once the message matched a pain they already felt every day, rather than one they had to be standing in the right moment to notice.

Two things changed together, and I think both mattered. Before, I was running a 14-day free trial at $29.99, the cheapest tier. I changed this to a 7-day free trial at $129.99, a hundred dollars more and half the time to decide.

You would be surprised what people will pay to solve their issue. I still think $129.99 a month is cheap for what Underway actually does now, I am not blowing my own trumpet, it is a genuinely good product. Shortening the trial to seven days puts real pressure on the decision instead of letting it drift, and the price increase filters for people who are serious rather than just curious.

I would not recommend making both changes if you are not also changing the message. On their own, a shorter trial and a higher price usually just lose you signups. It only worked here because the new positioning gave people a stronger reason to commit before they even hit the paywall.

Alongside the positioning and pricing change, I crafted new ads that fit the new message, and I will go through those properly in another episode. What I can say now is the number of signups went up and the amount I paid to get each one of those people to sign up went down, by a meaningful margin. Cheaper signups and more of them is the combination you actually want, not one without the other.

This is the part that made me believe the change was right rather than lucky. If signups had gone up but cost per signup had also gone up, I would have assumed the ads were just working temporarily, a novelty effect. Instead both moved the right way at once, which is a much stronger signal that the message itself, not just the creative, was doing the work.

Once you have a run of signups behind a consistent message, you can finally start forming your cost to acquire a customer, the CAC, and look properly at margins. Before this change I did not have enough signal to do that honestly, the numbers were too thin and too noisy.

I will be straight about this: I got a bill from Anthropic the other day and was a bit scared, thinking okay, we need to start making money. That is the blunt reality of running AI infrastructure under a SaaS, the model costs do not wait for you to find product-market fit. But after these last few signups, working out the monthly recurring revenue and annual recurring revenue, I am genuinely pleased, mostly because I now look at this as a long-term thing rather than a scramble.

If you are in the stage where a single infrastructure bill can rattle you, that is a sign to run this exercise now rather than later: list what each signup actually costs you to acquire, set it against what the new price brings in, and be honest about whether the gap is widening or closing.

I see this as a long-term thing now rather than a scramble for the next few signups. If I consistently keep doing what I am doing, in a year's time I want this to be a fully fledged business where I can make hires and bring in people who are the best at what they do, because I am not the best at everything myself.

What is even more exciting to me than the business side is how much better Underway itself will be in a year, the tech is improving rapidly and there is a lot still to show. Positioning and pricing get you the signups to find out whether the thing works; the product improving under them is what makes the long game worth playing.

Changing positioning, trial length and price together suits you if you already have some signal, you have spoken to real people, you have a product that genuinely does more than it used to, and you can afford a short dip while you test the new combination. It does not suit you if you have no existing read on who your customer is, because you will not be able to tell which of the three changes is doing the work.

It also does not suit a product that has not actually improved. The price jump only held because the thing underneath it had grown, it really does the job now. Raising price on a message change alone, without the product catching up, is how you lose trust with the exact people you have just attracted.