▶️ Video

Replay: AI trust gaps, marketplace mismatches, and data paralysis

Quick hits on when "smart" recommendations backfire, why value propositions can't be forced, and the difference between data and actual decisions

Sep 22 •

and

32:06

▶️ Service traps, liquidity lies, and the "I wish this existed" fallacy

Founders building custom solutions for every customer, marketplaces connecting people who don't want to be connected, and why "I always wished this…

Sep 15 •

and

34:59

Replay: Sample sizes, ego splits, and the "everything is free" myth

Most founders are drawing big conclusions from laughably small data sets while avoiding the hard conversations that actually matter. This week: why your…

Sep 8 •

and

36:49

Replay: pricing experiments, waitlist reality, and investor ultimatums

Watch now | A recording from JDM's live video

Aug 25 •

30:19

Replay: global pivots, crypto curveballs, and fuzzy dice wisdom

When should you pivot for unexpected users, ignore investor “advice,” or admit your traction is just your friends? This week, we tackled founder FOMO…

Aug 11 •

27:56

Replay: UX fixes, dead leads, and the "Kramer throttle"

Some users need a tweak. Others need a fire. And sometimes, your LLM answers its own questions like a caffeinated improv actor. Let’s talk experiments…

Jul 28 •

and

30:19

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…

Jul 21 •

and

25:57

Replay: founder flakiness, feature overlap, and... a rock emoji?

Your co-founder vanishes, users ghost, and a competitor just shipped your roadmap — it’s been a week. We tackled the founder drama, market panic, and…

Jul 15 •

and

26:17

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.

Jul 7 •

and

25:58

Replay: Not all signals are worth following

Startups don’t die from a lack of effort — they die from false confidence. Let’s talk about how to stop tricking yourself and test what really matters.

Jun 21 •

and

58:24

Replay: how good signals mislead great startups

Early traction is dangerous if shallow. In this office hours, we talked about going beyond the surface, testing actual urgency, and staying grounded…

Jun 19 •

and

51:28

Office Hours: traction, demos, and the cold start trap

We unpacked the patterns behind early startup struggles — loyal users that don’t grow, demos that don’t convert, and platforms that attract one side of…

Jun 3 •

and

38:17

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