The Bootstrapped Operator

Justin Comstock
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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.

  1. 18/12/2025

    Hiring for Fit: The 9 Interview Questions Every COO Should Ask

    Are you hiring for a small SaaS team? These 9 questions from The Ideal Team Player changed how I interview — and they help me avoid painful mis-hires. DM me and I’ll send the scorecard template I use. https://www.linkedin.com/in/justin-comstock-450a82a4/

    4 min

  2. 16/12/2025

    Slow is Smooth, Smooth is Fast: The COO’s Guide to Sustainable Productivity

    Thanks for listening to The Bootstrapped Operator. If this episode on Slow Productivity hit home — I’d love to connect. 👉 DM me on LinkedIn: https://www.linkedin.com/in/justin-comstock-450a82a4/ Let’s talk about how you’re leading, building, and working with more clarity — not more chaos. And if you’re interested in a small peer group of serious COOs, I’m building one — no fluff, just deep conversations and real execution.

    6 min

  3. 15/12/2025

    Crucial Conversations: The COO’s Superpower in Moments That Matter

    If you’re a SaaS operator on a similar path, let’s connect: https://www.linkedin.com/in/justin-comstock-450a82a4/

    7 min

  4. 14/12/2025

    The 5 Habits of Managers Who Don’t Micromanage (from EOS)

    DM me on LinkedIn if you want to join a small group of bootstrapped operators sharing real tools, challenges, and wins: 👉 https://www.linkedin.com/in/justin-comstock-450a82a4

    6 min

  5. 13/12/2025

    The Five Practices Every Bootstrapped COO Needs to Lead Well

    If this episode resonated, connect with me on LinkedIn. I’d love to hear how you’re applying these leadership practices in your business. 👉 https://www.linkedin.com/in/justin-comstock-450a82a4/ And hey — if you know another operator who needs to hear this, share it with them.

    6 min

  6. 12/12/2025

    Why Rocks Matter: The COO’s Guide to Real 90-Day Execution

    Want to connect with disciplined operators? I’d love to hear how you’re using EOS and Rocks to move your SaaS forward. Connect with me on LinkedIn and send a DM — always open to real conversations: 👉 https://www.linkedin.com/in/justin-comstock-450a82a4/

    6 min

  7. 11/12/2025

    Why Your Team Isn’t Working — and What To Do About It (Lessons from The Five Dysfunctions of a Team)

    If this episode hit home for you and you’re building a serious, profitable company without the chaos — I’d love to connect. 👋 DM me on LinkedIn: Justin Comstock. I’m gathering a peer group of serious operators who are in the trenches, doing the real work. If that’s you — let’s talk.

    7 min

  8. 10/12/2025

    The COO’s Discipline Advantage: Showing Up When It’s Hard

    If you’re a SaaS COO or serious operator building a bootstrapped company and this episode spoke to you — let’s connect. I’m building a private peer group for operators who are serious about execution, learning, and sharing the real stuff behind the scenes. 👉 Message me on LinkedIn — tell me what resonated, or just say hi.

    8 min
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About

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.

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