In this week´s episode Stewart Gandolf joins me to talk through what it actually takes to niche down, build a sustainable agency, and scale without losing your sanity or soul. Stewart’s been in the healthcare marketing game for over two decades, and his experience building Healthcare Success into one of the top firms in the space is loaded with tactical insight.
We talk about the trap of project-based work, how to structure your agency around recurring revenue, and why most agencies screw up their first few sales hires.
🕒 Timestamps & Topics
- 00:00 — How Stewart got his start and why he doubled down on healthcare
- 03:15 — Direct mail, seminars, and the early version of inbound
- 06:40 — NLP and the psychology behind language that converts
- 11:20 — What drove their early growth (hint: it wasn’t salespeople)
- 13:40 — Why project work is a trap and how to transition to retainers
- 16:00 — Right-sized clients vs. resource-sucking whales
- 18:20 — Inbound vs. outbound: nets, spears, and the bullseye metaphor
- 21:20 — Stewart’s playbook if he were starting from scratch today
- 25:00 — Authority assets: reports, seminars, and content that build trust
- 29:10 — The daisy metaphor and avoiding entrepreneurial distraction
- 31:45 — What most agencies get wrong with their first sales hire
- 37:10 — Traits of a great agency salesperson (and why most don’t have them)
- 40:00 — When to stop being your own best salesperson
- 44:15 — Strategic partnerships and the next wave of AI opportunity
- 47:45 — Final thoughts on staying relevant when the cheese moves
A few things we covered.
- Most agency salespeople fail, not because they’re bad, but because there’s no clear positioning to sell.
Links & Resources:
