Episode 839 | The Journey Growing Help Scout to $35M ARR

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