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](https://microconf.com/europe)┃Reykjavik, Iceland · Sept 21–23, 2026 - [MicroConf Connect](https://microconfconnect.com) - [TinySeed SaaS Institute](https://tinyseed.com/institute) - [TinySeed Mentors](https://tinyseed.com/mentors) - [Discretion Capital](https://discretioncapital.com/) - [Help Scout](https://www.helpscout.com/) - [Foundry](https://foundry.vc/) - [SavvyCal](https://savvycal.com/) - [Incorruptible by Eric Ries](https://incorruptible.co/) - [Nick Francis](https://nickfranc.is/) - [Nick Francis | LinkedIn](https://www.linkedin.com/in/nickfrancis1/) If you have questions about starting or scaling a software business that you'd like for us to cover, please[submit your question](https://www.startupsfortherestofus.com/contact) for an upcoming episode. We'd love to hear from you! Subscribe & Review:[iTunes](https://podcasts.apple.com/us/podcast/startups-for-the-rest-of-us/id366931951) |[Spotify](https://open.spotify.com/show/5089lJbLDOmXCvbcJzLZYj)