Why we picked it This is an operator being honest about the exact trap in your question: you win your first segment, then find the second one is far harder than it looked. Holdsworth built Hint inside direct primary care and openly admits that when they reached for adjacent segments like urgent care and specialty practices, the community trust and inbound engine that took years to build did not transfer. It is a good reality check that the moat that won segment one can make segment two slower, not faster.
Vertical SaaS: 80 Doctors to 1,000 Customers (Zak Holdsworth, Hint Health)
On The SaaS Podcast (SaaS Club) by Omer Khan (host), with Zak Holdsworth
- Founders underestimate how much of their first-segment success came from years of trust and referrals that do not copy over to a new segment
- Moving to a new segment often means rebuilding outbound sales from scratch because the inbound flywheel is segment-specific
- Frame the next segment as a deliberate critical-path bet, not a grab for extra revenue whenever a deal appears