The Bootstrapped Operator is a podcast for SaaS COOs and operations leaders running lean, growing calm, and doing the real work behind the scenes.
We talk to the people holding the company together — not chasing headlines.
If you're operating under $15M ARR, managing margin, systems, churn, hiring, and all the chaos between, this is your room.
No VC fluff. No founder hype. Just grounded conversations with operators who build quietly — and think clearly.
All content for The Bootstrapped Operator is the property of Justin Comstock and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
The Bootstrapped Operator is a podcast for SaaS COOs and operations leaders running lean, growing calm, and doing the real work behind the scenes.
We talk to the people holding the company together — not chasing headlines.
If you're operating under $15M ARR, managing margin, systems, churn, hiring, and all the chaos between, this is your room.
No VC fluff. No founder hype. Just grounded conversations with operators who build quietly — and think clearly.
As an introverted COO, communication didn’t come naturally — but it became essential. In this episode, I share a simple, powerful 3-phase negotiation framework adapted from Chris Voss (Never Split the Difference) that helped one of our CSMs de-escalate a tough customer conversation and rebuild alignment.
You’ll learn how to use calm, emotionally intelligent tactics to move from chaos to clarity, whether you're negotiating with customers, managing team tension, or navigating internal conflicts.
This isn’t about flashy persuasion — it’s about clear operator communication that actually works.
The Bootstrapped Operator
The Bootstrapped Operator is a podcast for SaaS COOs and operations leaders running lean, growing calm, and doing the real work behind the scenes.
We talk to the people holding the company together — not chasing headlines.
If you're operating under $15M ARR, managing margin, systems, churn, hiring, and all the chaos between, this is your room.
No VC fluff. No founder hype. Just grounded conversations with operators who build quietly — and think clearly.
