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 - Halifax co-working scene and the accidental birth of Mindsea 06:38 - Collaborative consortiums, committed co-discovery, and lessons from trying to share work 07:48 - How SalesRight was born from an internal tool and got acquired by FastSpring 10:19 - What Pace Pricing does - end-to-end pricing strategy for B2B SaaS 11:31 - The most common pricing problem - flatline growth, churn math, and expansion revenue 13:46 - Why pricing confidence comes from conviction, not just data 14:40 - Four levels of pricing validation and how to get there scrappily 17:32 - Jobs to be done, customer interviews, and using AI to analyze them 22:43 - AI in hiring, irresponsible NOT to use AI, and democratizing knowledge 25:40 - AI native vs AI forward, human-led AI-assisted 27:51 - Starting a business in Spain in one afternoon with Claude and landing pages 33:01 - Committed co-discovery - 90 days, 50/50, and why stealth mode is dead 35:08 - Trust as the real moat in AI businesses 37:00 - Love them, help them, pay you - the three things that matter 38:01 - Lightning round: airport anxiety, business class, couch work, inbox zero Bill Wilson Links: LinkedIn:   / wdrwilson   Company: https://www.pacepricing.com Blog: https://www.pacepricing.com/blog Jack Tompkins Links: LinkedIn:   / jack-tompkins   Consulting: https://www.pineapplecf.com AI Analyst product: https://www.pineappleanalyst.ai/ YouTube:    / @pineappleconsultingfirm