EPISODE 41

After forty episodes, Founder Mode pauses to look at the decisions founders actually struggle with once the playbooks stop working. This episode stitches together clips across healthcare, AI, pricing, capital, aviation, and personal health to show how judgment forms under pressure. You hear why go-live is the start of real work, how trust gets broken when tools ship before problems are understood, why usage outlasts any value narrative, and how busyness becomes a substitute for thinking. Across every domain, the pattern is consistent: systems fail quietly, discipline erodes downstream, and founders are forced to make calls without clean data, perfect timing, or consensus.

CHAPTERS

00:00 – Why the same founder problems keep repeating

01:01 – Go live is not the finish line

01:42 – Teaching interpersonal skills too late

02:34 – Adding AI before earning user trust

03:17 – When users reject AI and features get rolled back

03:57 – Why pricing complexity grows with mature markets

04:34 – Busyness as avoidance for founders

05:14 – Protecting thinking time before the business outgrows you

05:55 – Turning user complaints into learning fast

06:33 – Building a personal board of directors for health

07:27 – AI as a problem-solving lever, not a starting point

08:20 – Governance as the unlock for enterprise AI adoption

08:20 – When “magic” becomes table stakes for customers

09:10 – Why software being cheaper doesn’t make it easier

09:59 – Hybrid aviation as a trust bridge to electrification

10:51 – Measuring whether conference presence actually works

11:38 – Why AI scribes exploded in healthcare adoption

12:28 – Defaulting to venture capital and silent dilution

12:28 – Designing products that force focus and community

13:06 – Stress, judgment, and risk in aviation

13:43 – Unlimited pricing as a math problem

13:43 – Learning faster by removing safety nets

14:31 – Making decisions when there is no right answer

LINKS

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