SpecBite: an honest postmortem

SpecBite was a software-requirements SaaS — a tool to help product managers specify what they actually wanted before engineers built the wrong thing. I co-founded it, built it, took it through an accelerator, and shut it down about a year later. The engineering shipped. The business didn’t. This is the difference, written down so I don’t pretend otherwise.

I’m leaving the unflattering parts in, because a postmortem that only lists external causes isn’t a postmortem — it’s a press release.

The idea, and why I believed it

The premise was real: most software waste happens upstream of code, in the gap between “what the business meant” and “what the ticket said.” SpecBite tried to close that gap — structured requirements, acceptance criteria that doubled as test scaffolding, a shared language between PM and engineer. I’d lived the pain. That made me trust the idea more than the evidence justified.

That’s mistake one, and it’s the founder’s classic: I validated the problem and assumed the product. Everyone agreed the problem was real. Far fewer agreed that this was the thing they’d pay for, and I didn’t push hard enough on that distinction early.

What we built

A genuinely good piece of software, which is exactly the trap. Next.js front to back, strict types, a clean domain model for specs and their relationships, AI assistance for turning loose prose into structured requirements. It was fast, it was pleasant, it didn’t fall over.

I’m proud of the engineering and I’d build it the same way again. But “I’d build it the same way again” is a sentence about craft, not about whether anyone needed it. I optimized the part I was good at and comfortable with.

What went right

• The engineering held. No production fires, no data loss, types that meant what they said. The discipline I write about elsewhere started here.
• Founder Institute sharpened the non-engineering muscles — business plans, traction thinking, recruiting advisors, pitching. Uncomfortable on purpose, and worth it.
• I learned to ship a whole product, not a feature — auth, billing, onboarding, the unglamorous 80%.

What went wrong

• I built before I sold. The honest order is: get someone to pay, then build the thing they paid for. I did it backwards because building is where I feel competent and selling is where I feel exposed.
• The wedge was too wide. “Better requirements for everyone” is not a wedge; it’s a category. I never narrowed to one team, one workflow, one undeniable before/after.
• AI was a feature, not a moat. What felt novel in 2022 became a commodity faster than I could turn it into distribution.
• I confused activity with progress. A changelog full of commits felt like momentum. Momentum is paying users, and I let the dashboard I controlled (the repo) stand in for the one I didn’t (revenue).

The product was a B+. The business was an F. I spent my energy raising the grade that was already passing.

What I’d do differently

Sell first. Talk to ten people who feel the pain acutely enough to have already hacked together a spreadsheet for it, and build for them specifically. Treat “no” as data, not rejection. Spend the first month doing the thing that scares me (charging money) instead of the thing that soothes me (refactoring).

And I’d kill it sooner. Holding on past the point of honest signal isn’t grit; it’s an aversion to admitting the answer. The shutdown was the right call — I just made it a quarter or two late.

What it taught me

The clearest lesson is the one that now shows up in everything I build: reason about the failure mode first. SpecBite’s failure mode wasn’t technical, and I never modeled it, because I was busy modeling the parts that couldn’t hurt me. These days I do payments infrastructure, where ignoring the failure case is how you lose money — and I think part of why that fits is that I learned, expensively, what it costs to look away from it.

I’d do another startup. I’d just spend the first month terrified and selling, instead of comfortable and building.

Filed under startups. Killed something of your own? I’d genuinely like to hear it.