The Box You’re Not Checking
Just because you can build it doesn’t mean you should.
Last week, I got a message from a stranger on the internet.
My favorite kind.
He wrote:
"We’re now at the point of discussing how to integrate AI into our product. We have calls internally where we disagree on the direction and how much emphasis to put on it given the marketing climate in CRE. Your article rang true for me — focusing on solving a major problem and using AI as a tool and possible solution to do it, instead of doing it just to say we did.”
He asked if I’d meet with his team to share my perspective. I said yes.
Because I love talking to smart people building new things — especially when they’re asking the right questions. And these folks were. They weren’t looking to slap “AI” on a landing page and call it innovation. They were stuck. They had something. But it wasn’t growing fast enough. And they thought maybe AI would be the thing to unlock it.
But ten minutes into our call, it was clear that AI wasn’t the issue.
Their problem wasn’t AI. Their problem was not knowing the problem.
I’ve seen this before. A lot.
I used to have that problem too.
I wanted to do everything, all at once.
My mom would walk into my room and find every piece of clothing I owned — shirts, pants, swimsuits, winter coats — all laid out on the floor. I wanted to wear them all. I wanted to be every version of me, at the same time.
Until I got a steno pad.
One of those elementary school checklist notebooks, with crisp columns and bubble spaces you’d fill in when you finished your work. It turned my chaos into clarity. One line. One task. One win at a time.
I was obsessed. I became the girl who turned in the neatest, most perfectly scripted steno. (My cursive was a 99 out of 100. The teacher didn’t believe in giving 100s. She said perfection was a myth. I said watch me.)
I even got asked to forge a classmate’s mom’s signature. (I said yes. Shame on me. But also — what a compliment!)
And as a former founder, I’ve been guilty as charged.
Founders think they need to build more. Add more. Expand the roadmap. Especially today with tools like Cursor, Replit, and other AI copilots at your fingertips, it feels like you should do it all.
But most of the great CRE tech companies started with one box on the checklist:
Juniper Square became the default investor portal by solving one pain point: LP communication. Now they handle fund administration, CRM, performance reporting — but they didn’t try to be Carta plus Investran plus Salesforce on day one. They just replaced the janky Excel + DocuSign + Dropbox routine sponsors used to send out distributions (and yes, I was one of those sponsors).
VTS started with lease tracking and pipeline management. Not asset management. Not marketing. Not tenant engagement. Just: replace the broker’s Excel sheet. Today, VTS has expanded into asset performance dashboards, market intelligence, and tenant experience platforms — but they earned the right to do that by nailing leasing first.
CompStak gave brokers a way to trade comps. That’s it. Now, they offer full CRE data analytics for lenders, appraisers, and investors — but only after they solved the “how do I get comp data without calling five people?” problem.
They didn’t launch as “end-to-end platforms.” They built trust by doing one thing well — and used that momentum to earn their next expansion.
Look, I get it: when every prospect says, “You know what would be great? If you could just add this one thing…” it’s hard not to listen.
But some of the best advice I ever got was this: take those comments with a rock of salt. Not a grain — a rock. Because most people don’t want to tell you the truth. They want to be polite. They want to avoid being the bad guy.
The Mom Test nails this: people will lie to avoid awkwardness. Especially when you’re asking for a purchase or even just for feedback. So when someone says, “I’d buy it if it just had XYZ feature,” ask yourself: did they commit to anything? Money, time, contract? If not, don’t build it.
Otherwise, you're not building a roadmap — you're chasing [future] ghosts.
The truth is, there’s real power in doing one thing well. You get clarity. Momentum. Traction. The kind of traction that earns you the right to build more later.
It’s tempting to skip ahead. To wear all the clothes at once. To build the everything app. Especially in real estate, where the problems are endless and interconnected and every client says, “You know what would be great? If you could just add this one thing…”
But the steno pad doesn’t let you skip steps. You fill in the bubble. One at a time.
And if you’re building something right now — AI or not — that’s the question to start with:
What’s the box you’re not checking?
👉 You subscribed? Great. That’s one box checked.
Jen’s Reading Corner
None this week, just catching up on other newsletters.
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Good article! Kindergarten strikes again! Steno check!