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Replay: pilot purgatory, defensibility drama, and the gym sock of startup funnels

We're live 3x per week now, and this one was jam-packed with another stack of founder questions — and a few brutal truths.

Hey friends 👋

Another week of Office Hours is in the books — and this time, we covered traction tips, investor tea, and at least one metaphor involving a gym sock and a shower rod.

If you missed the live chaos (or the tequila), you can catch the Substack replay at the top of this post, and links to LinkedIn and Instagram replays below.

What does ‘too early’ actually mean?

Substack (every Tue @ 9am PST)

Watch the replay above — and listen for:

  • “More traction” decoded: what VCs are really asking for

  • Why “Stripe for X” is not a strategy

  • When “we love the team” means “we’re passing politely”

  • The dangers of confusing compliments with commitment

  • A teardown of patents-as-defensibility (and better alternatives)

Spoiler: It’s not about growth — it’s about risk. And when founders confuse activity for progress, investors can smell it a mile away.

Get more from JDM in the Substack app
Available for iOS and Android

When good feedback leads nowhere

Instagram (every Thur @ 9am PST)

Watch the replay →

We unpacked:

  • Why a waitlist of 600 is not the same as a launch strategy

  • What “retention through gamification” actually signals (hint: a vitamin, not a painkiller)

  • The problem with positive vibes from nonprofits and no actual deals

  • Why some startup funnels are like “a gym sock on a shower rod… just hanging there. Ugly. Damp.”

The startup trap of building for the wrong buyer

LinkedIn (every Fri @ noon PST)

Watch the replay →

We got into:

  • Marketplace with 150 onboarded pilots… and zero bookings

  • What activation failure actually tells you (hint: it’s not just onboarding)

  • The critical difference between perceived value and urgency

  • The secret to running pilots that actually convert: pre-close customer discovery

  • When to ignore “go after a bigger market” advice (and when to take it seriously)

Also:

  • The Credible Theory of Hugeness made another appearance

  • Defensibility ≠ patents

  • A brief but extremely serious discussion about Hannibal Lecter and gravity

Can’t Make It Live?

No worries. Our Office Hours intern — a very judgmental AI agent named Cass — is standing by to collect your startup questions for next week.

Just drop a comment or reply.

See you next week.

Same time. Three platforms. Zero fluff.

— JDM & Cam

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