Waymaker rocks AND Waymaker sucks: an honest review from the founder

Most founders write puff pieces about their own products. This isn't that.

I built Waymaker. I also use it every day, ship from it, and break it more than anyone else does. So I'm going to tell you what's genuinely working — and what still has rough edges I'm actively grinding down.

What rocks

Cofounder holds context across projects. This is the thing I'm most proud of. Most AI tools forget you the moment the chat ends. Cofounder remembers your goals, your constraints, your projects, your decisions. I forget what I said three weeks ago. It doesn't. That single difference changes what you can use it for — from “answer this one question” to “be the partner who already knows the plan.”

The 29 playbooks aren't templates. They're real shipping paths, built from projects that actually shipped. When you pick one, the Brain seeds and tasks auto-wire into your workspace so you're not staring at a blank file — you're at step 12 of a path that's already worked.

It's built for solo and small teams. When you don't have a PM, a designer, an engineer, and a security team, you have you and AI. Waymaker is the seats around you. The UX critique you'd get from a designer. The security scan you'd get from an engineer. The plan-holding you'd get from a chief of staff.

Operator-built, not VC-pitched. Every feature exists because I needed it Tuesday. Some of those are unusual choices. They're unusual because most software is designed by committee. Mine is designed by someone who shipped.

What sucks (today)

Onboarding is heavier than it should be. Too many concepts upfront. We're trimming. The right path is “show, don't explain” and we're not all the way there yet.

Cofounder occasionally ships the wrong recommendation with high confidence. This is the worst failure mode of LLM-backed advice. I'm working on the calibration loop — making it surface uncertainty rather than smoothing over it.

The LMS UX feels like 2.5 different apps in a trenchcoat. Courses, modules, lessons, certificates, and the coach marketplace all evolved separately. A unification pass is in progress. Until then, expect some seams.

Mobile is rough. Desktop-first is intentional for the building use case — you're not shipping a product from your phone. But the gap is wider than I'd like for the daily check-in / Brain capture flows. On the roadmap.

Documentation lags features by about 3 weeks. This is embarrassing and I own it. The platform is moving faster than the docs. We're catching up.

What I'm betting wins anyway

The AI tools market right now is saturated with prompt collections, chatbots, and “ChatGPT but for X.” That entire category will keep shipping faster, cheaper, and lower-margin until it commodifies.

Waymaker is a different bet. It's the operating layer above those tools. It doesn't compete with Claude, Cursor, or Lovable. It holds your plan, captures your patterns, and watches for the gaps that those tools — being focused on individual tasks — can't see.

That's not a feature anyone else is building. It's harder to demo. Harder to sell. And exactly what I keep needing.

If you're solo or small-team and tired of starting every project from zero, that's the bet I'm making for you.

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Where to start

If you want to see the rough edges yourself, two paths:

• Take the free 3-minute AI Skills Audit — it'll route you to the right entry point based on your builder type.
• Open a free Cofounder conversation — describe what you're working on and let it build a plan with you.

Either way, you'll see the parts that work and the parts that still need polish. I'd rather you see both than discover one later.