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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
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
Creators and Guests
Host
Pascal Unger
Co-founder / Managing Partner at focal.vc We lead pre-seeds in North America with up to $1M: We exclusively back AI native software startups at the very start. Thereafter, we help them get off the ground better and faster, supported by a network > 200 GTM executives. That's our singular, unwavering focus.
What is focal podcast?
Pivotal early lessons of today's best startups.
Welcome to the focal podcast where we go deep with some of today's best founders and operators on ONE crucial lessons from their early days.
This podcast is not the usual "highlight reel" startup podcast that goes one inch deep across 20+ topics. Rather, we ask the questions you’d ask if you were sitting across from them. No fluff, just the real, actionable insights you’d get if these founders were mentoring you 1on1.
We cover topics including:
- What worked and why.
- Costly mistakes and how they fixed them.
- Frameworks that truly made a difference.
- Tactics to move faster.
- What they wish they’d known sooner.
- And much more!
"Only a fool learns from their own mistakes. The wise learn from the mistakes of others."