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Replay: free users, flimsy pilots, and the fantasy of readiness

Startups don’t fail because they build the wrong thing—they fail because they launch too late, believe every soft “yes,” and can’t tell the difference between pull and push. Let’s fix that.

Hey friends 👋

Let’s talk about launch lies, pricing panic, and what to do when “interested” customers suddenly ghost you.

Substack Office Hours Recap

Cam had a conflict, so I took this one solo.

I kicked things off with one of the most deceptively simple startup questions:

How do I know when I’m ready to launch?

And the answer? You’re not. Not in the way you think.

There’s no such thing as “launch readiness”—only readiness to run an experiment. Launch isn’t a finish line. It’s a hypothesis test:

Can I get this group to do that thing if I put this offer in front of them?

You’re not launching the product—you’re launching a conversion hypothesis. And the faster you test it, the faster you learn what’s broken (your offer, your audience, or your ego).

Other spicy moments included:

  • EHR integration trap: When three clinics say “I’ll buy it if…” but every “if” is a different EHR, do you build one, build all, or walk away? (Hint: chase logos, not hallucinations)

  • The $19 CRM no one will buy: If your pricing is low and they still say “not yet,” the problem isn’t price—it’s priority. You’re solving problem #7, not #1.

  • Stalled growth and morale: Revenue is a lagging indicator. Momentum comes from learning velocity. If you’re still learning, you’re still moving.

LinkedIn Live Recap

Over on LinkedIn, Cam and I tackled:

  • The pilot purgatory problem: Investors keep asking for a pilot. Then they want it to be paid. Then they want ten of them. If they keep moving the yardstick, it’s not guidance—it’s a slow “no.”

  • B2G delusion: Thinking a great interview turns into a quick government pilot is like thinking a first date leads to a mortgage. Learn the procurement process—or get ghosted.

▶️ Watch the replay on LinkedIn →

Instagram Live Recap

The IG stream was a bit of a chaos experiment (shoutout to Restream quirks), but the content was 🔥:

  • Push vs Pull: If you’re trying to “convince” users to pay, you’re already losing. You need pull—users with pain so sharp they reach for your product like it’s Advil.

  • Cold start, warm signal: If your marketplace has vendors but no customers, you don’t need more supply—you need one tight use case that creates instant liquidity.

  • Feature chaos: When every user wants something different, it means you’re solving nothing well. Go narrower, not broader.

▶️ Watch the replay on Instagram →


Wanna join the next one?

Office hours are live every week on Substack (Tuesdays @ 9am PT), Instagram (Thursdays @ 9:30am PT), and LinkedIn (Fridays @ 12pm PT).

You can see the schedule and drop your questions here: jdm.bio/calendar

Let’s stop guessing. Let’s get traction.

—jdm

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