Brand positioning: did I get it all wrong?
by Richard Lovatt · updated 21 October 2026
Not wrong, just expensive to buy on. My own positioning for Underway, don't miss day one, tests well in conversation but only converts someone the moment they are about to start a new project, which is rare to catch with ads. The fix I am testing is not a new product, it is leading with no editing and content handled for you, aimed at business owners with mature companies.
In short
- Messaging that everyone understands is not the same as messaging that converts, because it depends on catching someone at one exact moment
- Don't miss day one only lands if the person is about to start a project right now, which ads cannot reliably time
- A single real conversation, with Ryan, surfaced a positioning gap no amount of landing page views showed me
- The content-first pitch, we handle it for you, aims at business owners who already know they need content but find starting the process hard
- I am testing this, not replacing the old message outright, because one piece of feedback is data, not proof
Doubting the positioning
I'm wondering whether I got it all wrong. Not the product, the messaging. From everyone I've spoken to, and yes it could be biased, nearly everyone understands it and says it clicks. There needs to be something like this on the market, they get all of that. But I think it's an expensive way of getting customers to use it, and that's a different problem from the message being wrong.
The gap is between understanding and converting. People can hear don't miss day one, nod, think that's cool, and still not be the person who signs up today. Agreeing with a message and being moved to act on it are two different things, and I'd been treating them as the same.
Don't miss day one: why timing is the whole message
The advertising is about finding people in that moment, because it's hey, don't miss day one, you can't film today tomorrow. Imagine Jeff Bezos building Amazon, we want to see the start. Everyone gets that the messaging is right. But what I think happens is people think oh that's cool, let me have a look around, let me sign up, give my email, but they're not in. It's rare to be in that moment where they're about to start a project.
That's the structural weakness. It's not that the line is wrong, it's that it only works on a narrow window of people, those about to begin, and finding someone in that exact moment means being in front of so many people that the chances of them feeling it there and then are so much less than something aimed at a bigger, steadier group.
Catching people at the right moment: what Ryan's call showed me
I spoke to Ryan yesterday, who signed up. He's a successful business owner in California. It hit home because he's starting an animation project, and he realised he needed exactly that kind of thing. He was impressed, thought it was really cool. That opened the door for me, because I was thinking this is the kind of person I need, but to find someone in that moment at the right time is so much harder than something else.
I'm recording this because these are the thoughts that brand owners and business owners have and never say out loud. Ryan also gave me feedback that wasn't really feedback, more a question: he said he has another business, his more mature one, and asked could he use it for that too. I realised that was the gap. Him needing to ask whether he could use it was telling, because I think he knew he could, it just wasn't positioned that way.
Could I use it elsewhere: the question that exposed the gap
Ryan asked, do you think it's a good idea to use Underway for my other business when I'm doing X, Y and Z. That question should never have needed asking. If the positioning only calls out starting a project and not missing the beginning, then anyone with an existing, thriving business has to do the mental work themselves of deciding whether this still applies to them.
All business owners probably do go by this. No doubt they think, if I get a new project, this would be good for that. They're probably interested, they probably have a look. I've got a hell of a lot of landing page views. But it's the next bit, the conversion, that isn't happening, and Ryan's question is the clue as to why.
Landing page views, no conversion: what the numbers were telling me
They probably have a look, I've got a hell of a lot of landing page views, but it's that next bit, the conversion, that isn't happening. That's the pattern I keep landing on: interest without action. People recognise the problem, agree it's real, and still leave.
Running ads every day on Meta and X is costing money, and when you're losing money every day it's a hard situation to just keep going. If someone stays and pays every month for a while it works out, the lifetime value could be good, but the gap between views and paying customers is where the budget actually disappears.
A Trojan horse approach: leading with content, not with day one
I'm really thinking about whether I have to change my positioning, or go with a Trojan horse method to get people to use it. For me it's how could I attract business owners who have a thriving business and just want to start documenting and creating content. I think a lot of business owners know they need to be doing content, forget about documenting for now, they know they need to create it. It's just the process of thinking about that which is hard.
So instead of the positioning being hey, document from day one, it becomes hey, don't worry about content, we sit down, we've got it all for you, we edit it, we ask you questions, and we put it all together. I'm not saying one is better than the other, I'm saying I feel like I'm going to have to test that out to business owners.
Business owners and content: why I think this group converts easier
Business owners with mature businesses have more money, and they also set up new projects all the time. I feel like they're an easier group to get onto the platform, because I make their life easier to create content, and that then sets them up for starting new projects too. It's not either or, the content-first pitch can still lead back to the day-one promise once they're using it.
This is a hunch built from one conversation, not a tested result. I wouldn't have thought of it unless I'd run these ads, got that customer in, and had the chance to speak to him directly. That's the value of running ads that lose money daily, it's data and feedback, even when the number on the page is going the wrong way.
Ad spend losing money daily: the cost of testing this out loud
It's pretty hard running ads every day on Meta and X, and it's costing money. If someone stays with me and pays every month, lifetime value could be good, but when you're losing money every day it's a hard situation to keep going. That's the honest backdrop to all of this: the positioning question isn't academic, it's being paid for daily in ad spend.
As long as I'm moving forward I think it's good, but it is making me evaluate these things. I have to take the learning lesson. I wouldn't have known to question the day-one message without a customer telling me, in his own words, that he had to ask whether it applied to him.
Questions people ask
What does Underway's don't miss day one positioning actually mean
It's the idea that nobody filmed Jeff Bezos building Amazon from day one, so Underway exists to make sure founders starting something now don't miss recording the beginning. It tests well when people hear it, they say it clicks and that there's a real issue there, but it only moves someone to act if they happen to be starting a project at that exact moment.
Why doesn't a message everyone agrees with always convert
Agreement and action are different things. People can look at an ad, think that's cool, let me have a look, let me sign up, give my email, and still not be in the moment the message is aimed at. Landing page views can be high while conversion stays low, because the message only fires for people about to start something right now.
Is a content-first pitch better than a day-one pitch for business owners
It's being tested, not proven. The reasoning is that business owners with established companies already know they need to be creating content, so the hard part isn't convincing them of the value, it's removing the thinking involved in starting. Leading with we handle the content for you may suit that group better than leading with don't miss the beginning.
How do you know when your positioning is wrong versus just expensive
If people consistently say the message hits home and the problem is real, but landing page views don't turn into signups, that often points to timing rather than a wrong message. In this case the positioning only lands on someone at the rare moment they're about to start a new project, which makes it expensive to buy at scale through ads.
What should you do with one piece of customer feedback like Ryan's
Treat it as a lead to test, not a verdict. One conversation surfaced a real gap, that an existing business owner had to ask whether the product applied to his other, more mature business, but it's one data point against a lot of ad spend and page views. The right next step is to test the alternative message, not overhaul everything on one call.