The Startup Ouroboros
Step 1: Help them. Step 2: Sell them something. Step 3: Make it so confusing they hire someone else to explain it.
“Now they won’t even talk to us.”
That’s what he said. And he said it with the bewildered frustration of a man who once had full backstage access and now can’t even get through the velvet rope.
This founder—let’s call him Dave—eventually sold his startup. Not his first. Not even his flashiest. Just one more successful notch in the demo deck of his career. We were catching up, and he casually mentioned how much had changed since they startup.
Me: How’s the startup going? Any big movement?
Him: You know, it’s crazy. We went from being this small team that did some consulting—customers would hand us the keys to the castle—they’d show us everything. Process docs, org charts, internal Slack drama. One guy literally gave us all his passwords. Like, we didn’t even ask.
Me: And now?
Him: And now we’re selling a “product”. A clean, lovely, scalable product. And the same clients who used to overshare won’t tell us anything. They go full blackout. Everything’s now “proprietary.” They just want the thing to work without explaining how they work. We ask about their workflows and they say, “Don’t worry, it’s standard.” It’s NEVER standard!
The shift—from transparency to tactical redaction—happens quietly. At first, customers overshare because they see you as a helper. An outsider with no power and probably useful opinions. But once you have a real product, with a roadmap and an enterprise-level price tag, they stop confiding and start treating you like a vendor. Vendors get decks. They don’t get context.
It reminded me of another conversation, this one with a startup advisor. He was new to proptech, but deeply seasoned in the legacy enterprise software scene—think SAP, Oracle, or one of those capital-letter commandments that charge seven figures for the right to click “save.”
Me: What’s the biggest difference between big tech and proptech?
Him: In big tech, clients adapt to the software. In real estate, they expect the software to adapt to them.
Which... yes. But also… not quite.
Because both he and the founder are describing the same thing from different vantage points. It’s not about the industry. It’s about the stage.
When you’re early, you're not really selling software. You’re selling insight. You’re building while listening, asking questions under the guise of “discovery,” and getting access to things no vendor ever should—because you haven’t become a vendor yet. You're a smart person or team with a laptop and a promise.
But once you evolve into a true product company—features shipped, salespeople hired, pricing page polished—you stop being a trusted confidante and start being a procurement line item. Customers stop inviting you to strategy calls and start opening support tickets.
And here’s the twist: if you’re lucky—if you’re really, really lucky—you make it far enough around the spiral that you get to be a consultant again. Just not personally.
You become the thing people consult around.
Oracle did it. Salesforce did it. Even the PMS-that-shall-not-be-named, that grand poobah of Byzantine tech, built its fortune on licensing fees and a thriving priesthood of certified interpreters.
When does that turn happen?
You know you’ve made it when:
Your product becomes the process.
You’re no longer a tool. You’re infrastructure. Nobody questions the plumbing—they just hire someone to fix it when it breaks.Your buyer and user don’t speak the same language.
The VP signs the contract. The analyst implements it. Neither of them knows what “custom object” means.You require a translator.
Like many of the old PMSs, whose documentation might as well be printed on papyrus. If your software needs a Sherpa, congrats—you’ve achieved altitude.You’ve stopped pretending to be simple.
Early on, you market simplicity. Later, you market indispensability. One is delightful. The other is defensible.
So yes, the arc is real.
Call it the startup cycle of sin:
Consult → Codify → Complicate → Canonize.
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Jen’s Reading Corner
I’m currently reading Designing Your Life. It came highly recommended by a friend ages ago, and I’m excited to see what the workshopping will suggest I change in my life.
Anyone want to read it with me? Reply to this email, and we’ll start a little book club.
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