The Emperor has no GTM

So often, when you come up with an idea or build something that scratches an itch, your next thought as a founder is that the only thing between you and success is everyone knowing about this.

It might be true, but not in the way you think.

You do need people to know about this, but not because they're one step away from signing up. You need their feedback on what you did wrong or why it's not everyone who needs to know about this, but a very particular slice of the market—one that may or may not be big enough to sustain a company

I'm experiencing this firsthand because I built something and just signed up my first customer. Somehow, despite the fact that I've been giving this advice to founders for 20 years, I was really surprised at how much I learned and how much my expectations needed adjusting after just two waves of email outreach to 25 customers each—outreach I thought was marketing, but now I realize is still due diligence.

Here's what I'd fixed:

I'm the board president of a 40-unit co-op in Park Slope. When our maintenance went up 9% last year, all of it taxes and insurance, I went through every line item we could control and found $3,000 a year going to BuildingLink, a resident portal that feels a bit like you’re using MS-DOS. Our super never logged into it to close out tickets and our residents had abandoned the clunky message board for a lively WhatsApp group.

We're a simple building that started out with a small management company and no full stack enterprise system underneath us. We didn't need a platform. We needed maintenance tickets the super could close by text, a way to reach everyone in an emergency, and the house rules in one place.

So I built it.

It's called OurBuilding. It's $79 a month, nobody has to install anything, and our residents and staff actually use it, which is more than I could say for the thing it replaced.

I even threw in a fancy home insurance checker powered by AI that helps our building manager speed up reviews of all the coverage details of each policy.

We launched it, tested it, I ironed out all the bugs, and the board voted to end our existing portal contract with BuildingLink. The building saved $2,000 a year.

That's a real customer and a real result.

Kind of.

Obviously I had something to do with that sale, but I’m inclined to think there’s lots more opportunity here. Everyone I know who lives in a building with BuildingLink thinks it sucks, and they’re all generally supportive of me.

On the other hand, none of them is the person who picks the software for a building. None of them could have told me what the other systems out there even were.

The signal I had wasn't zero. It was worse than zero, because it felt like validation. If you've started anything, you have a version of this. The people who love your first version are probably the people who already love you.

Here’s where I learned my lesson: In August, I pulled every co-op and condo in Park Slope between 30 and 99 units, found the managing agents on the city's registration records. I got 27 work emails into the first batch, and sent them a note. The list was targeted on two things: where the buildings were and how big they were. Nothing about who these people were, what systems they likely ran, or whether they could say yes.

Here's how my marketing turned due diligence went.

The subject line was "From the Board President at Plaza St West — How we saved $2000 annually." I thought the title carried credibility. I didn't even think about my email in the context of everything else they get in their inbox.

The first reply I got back:

"Please be advised I do not manage this building."

She thought I was trying to write to a board president on Plaza Street West because her first triage of any email is just, "Which building that I manage does this relate to?" Her inbox is just a flood of other people putting things on her todo list.

The credential I led with gave her a great signal to turn me down.

Not my circus. Not my monkees.

Next.

Even for the positive responses, I was underprepared. A couple of people wrote back and asked for marketing materials.

I didn't have any. Who needs more than an email and a link?

Someone who's going to pitch this to a board. That's who. They need a PDF. It's going to go into a board package at some point, or at least as an email attachment.

No one in the world likes email attachments more than property managers.

My first blast also accidently turned up a competitor: a property manager who had done the same thing, scratched their own itch, and was starting to use software In their own buildings. With better research, I probably could have avoided that by checking out their domain, or having Claude do it.

I went back to work and put together a marketing site that answered questions and I drafted what I thought was a better note.

My second pitch was stronger, but the list wasn’t filtered at all. I sorted the list by who managed the most buildings, because one yes at the top is forty buildings. The top of the list was a contact at a big firm attached to 182 buildings.

She turned out to be the person who files the registration paperwork. Nobody manages 182 buildings. Nobody manages more than fifteen or twenty. I learned that just because you're a customer doesn't mean you know enough about the orgs you’re selling into to score a contact list of leads.

I (Claude) retargeted to firms running five to thirty buildings, where the person on the paperwork is the person who signs, and sent the next 25. An hour later the CEO of a 12-building Brooklyn firm replied. The full text: "We use Buildium and Appfolio. Their pricing is on their websites."

My first read was that he hadn't understood why I was writing. My second read was that he understood perfectly that was what I asked in the email. I wanted to get on a call with anybody who was interested, and I made my call to action a bit of a throwaway line. I literally asked, "Would love to know what you're using and how much you're paying for it."

He just answered me.

I was just asking the wrong question.

Buildium and AppFolio are all-in-one platforms, accounting and resident portal in one place, and a firm standardized on one of those is not going to swap out a total solution for a point solution, no matter how good the text-message ticketing or insurance review is. I built a replacement for BuildingLink or anyone using a tangled mess of google groups, ClickPay, Monday, etc. He doesn't have BuildingLink. There was nothing to replace. When we went back and checked the websites of every firm I'd emailed, five were on AppFolio, one mentioned BuildingLink, and most of the rest had nothing on the resident side at all except a way to collect the maintenance.

I'd been describing the product as cheaper than what they had, to people who either had everything or who had nothing.

What I should have thought in August wasn't "everyone needs to get a look at this." It was "I need to find out who this is specifically not for, and who it's for.”

Next version of the e-mail did nothing but test and filter.

“Is this true for you?

1) No "one ring to rule them all"... Clickpay for payments, Buildinglink for maintenance and emergency notifications, maybe a Google Group in there somewhere... financial backend on something different like Yardi.

2) Your boards feel like they're paying too much for what you use.

3) Residents go around your app in favor of just texting, especially with the super.

4) Insurance certificates get read through (hopefully) by a person.”

It’s basically asking them to say, “No, your thing isn’t a thing.” You want to send a sales e-mail that gives you a strong negative signal—not one someone can’t say no to.

That's the uncomfortable version of customer discovery, especially if it means being open to the idea that it isn’t for anyone besides you.

This is also why so many founders think the thing standing between them and traction is funding, which means money for marketing. Money for marketing means reach, and reach is the thing you don't need yet. Two waves of emails cost me nothing and taught me more than spending budget would have. A budget would have told the wrong people about the product faster, probably with the wrong message.

When you think you have something, assume you don't.

Then go try to prove yourself right, not wrong.