Hey friends 🤘
You know the pattern: founders hear encouraging words, dodge the uncomfortable price conversation, and call it traction because everyone is smiling.
Cute. Also dangerous.
For episode 99, we put Office Hours on the podcast feed and took four founder questions that all circle the same problem: founders trying to avoid the signal that matters. Will customers pay more? Will free pilots convert? Should contractor software start narrow? Can two engineers enter healthcare without a regulatory sherpa?
We get into price increases, the danger of unpaid pilots, why “everyone does things differently” is usually a reason to narrow instead of broaden, and why HIPAA probably should not be the first scary thing you fight at idea stage.
Plus, frivolous thoughts include Blues Traveler harmonica heroics, aging Cards Against Humanity references, and the unsettling moment your family reveals exactly how dark they think your sense of humor is.
As always, thanks for listening.
—Cameron and JDM
Timestamps
00:00 - Introduction
02:15 - Low T and episode 99
05:30 - Raising prices without panicking
12:45 - Free pilots that never convert
25:00 - Narrowing contractors and healthcare fear
40:00 - Frivolous Thoughts
