Bootstrapping to $10M ARR was easier than raising the first $20M.

This episode is a masterclass in founder decision-making: choosing (and parting with) co-founders, bootstrapping to real revenue, then raising at scale - without losing the plot. Expect frank takes on titles, burn, investor selection, and the moral weight of taking other people’s money.

Duncan Weatherston is the co-founder and CEO of Smile Digital Health, a leading healthcare data platform company. He and his team bootstrapped to ~$10M ARR before raising a $20M Series A, and are now well past $50M in ARR.

01:40 - Why start with co-founders vs going solo in healthcare SaaS
06:27 - How to vet co-founders: proof of execution over chemistry
06:58 - The #1 mistake: trusting claims without validating capability
09:39 - Early-stage stars rarely scale—how roles must evolve
12:25 - Title inflation trap: why early VP labels backfire later
12:47 - Be mercenary with misfits: fairness to the team > feelings
16:56 - Create IC ladders: don’t “promote” top engineers into management
18:27 - Founder vesting: avoid dead equity with 5–6 year schedules
19:46 - Why they bootstrapped first: expertise, low burn, paying customers
22:40 - Would he raise earlier today? Services-led product tradeoffs
25:47 - The $20M decision: buyouts, tailwinds, and scaling delivery
34:04 - Taking VC creates a moral obligation—here’s what that means
36:56 - 2021 mistake: “spend aggressively” and adapting too slowly
45:59 - The do-over: fix org design, roles, and accountability sooner
46:25 - Popular advice he rejects: don’t contort your playbook to fads
48:41 - PMF obsession: identify your repeatable sales unit before scaling
51:03 - Best investor advice: hire actual A-players, not just roles