Latest / Scrappy but Successful [Consultant's Personalities When No One's Watching]
26. How B2B SaaS Companies Leave Money on the Table with Bill Wilson
Bill Wilson has built and sold two companies, helped dozens of B2B SaaS founders fix their pricing, and started a brand-new business while walking through a market in southern Spain. He joins Jack to break down why most pricing problems are actually positioning problems, what scrappy founders get wrong about churn math, and how to start a testable company in a single afternoon with AI.
Chapters:
00:00 - Intro and scrappy vs sophisticated
01:09 - Growing up across Canada and the entrepreneur in the family
02:40 - First company at 18, swearing off business, then getting pulled back in
04:35 -…
The skinny
The skinny isn't ready yet — notes appear once the transcript is processed.