What happens when a bootstrapper at heart raises $28 million and spends the next decade living with that decision? In this episode, Rob Walling sits down with Nick Francis, the co-founder of Help Scout, to walk through the full 15-year arc of building one of the most beloved support tools in SaaS. From the cramped Techstars apartment he shared with a co-founder, to the decision to become a public benefit corporation, to the bold pricing overhaul that ultimately became a turning point in his time as CEO, Nick holds nothing back. Topics we cover: (2:00) – Help Scout's origin story (4:30) – Techstars $18K for 6% equity (7:56) – Getting the first 50 customers (11:13) –  Raising a $12M Series A (13:37) – Would Nick raise again? (19:23) – Becoming a B Corp (22:27) – Help Scout's AI strategy (26:02) – Per-seat to per-contact pricing (32:03) – Stepping down as CEO Links from the show: MicroConf Europe┃Reykjavik, Iceland · Sept 21–23, 2026 MicroConf Connect TinySeed SaaS Institute TinySeed Mentors Discretion Capital  Help Scout  Foundry SavvyCal  Incorruptible by Eric Ries  Nick Francis Nick Francis | LinkedIn If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you! Subscribe & Review: iTunes | Spotify