The Bootstrapped Operator podcast artwork

PODCAST · business

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.

  1. 13

    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/

  2. 12

    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. 

  3. 11

    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/

  4. 10

    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

  5. 9

    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. 8

    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/

  7. 7

    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.

  8. 6

    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.

  9. 5

    EOS in Real Life: Right People, Right Seats

    🔗 Let’s connect on LinkedIn:If you're an operator building something real — without the noise — I'd love to meet you.DM me, share your thoughts, or tell me what resonated with this episode.👉 Connect with Justin on LinkedIn

  10. 4

    The Ideal Team Player: What Every COO Needs to Know to Build a Great Team

    💬 Let’s connect and swap notes — especially if you’re building a SaaS team without outside funding.I’m looking to meet more COOs and calm operators.👉 Chat with me on LinkedIn

  11. 3

    Deep Work: Your Secret Weapon as a Bootstrapped COO

    👋 Are you a bootstrapped COO or calm SaaS operator?I’m building a private peer group for serious operators who value systems, execution, and deep work — not noise.If you’re into EOS, traction, and scaling without chaos...Let’s connect and compare notes.👉 Message me hereNo fluff. Just real ops talk.

  12. 2

    Rocks That Actually Roll: EOS + Deep Work For Bootstrapped COO's

    🎯 Want to compare notes on running lean, EOS-driven SaaS ops?I’m building a private peer group for calm, bootstrapped operators. If you’re serious about the work — let’s connect.👉 Message me on LinkedInNo fluff. No hype. Just real execution talk.

  13. 1

    The Quiet COO’s Guide to Better Conversations

    If this episode resonated — or you’re a fellow operator navigating the chaos of bootstrapped SaaS — I’d love to connect.Shoot me a message or just say hey on LinkedIn:👉 linkedin.com/in/justin-comstock-450a82a4Let’s trade notes. No fluff. Just real ops.

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ABOUT THIS SHOW

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.

HOSTED BY

Justin Comstock

Frequently Asked Questions

How many episodes does The Bootstrapped Operator have?

The Bootstrapped Operator currently has 13 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is The Bootstrapped Operator 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,...

How often does The Bootstrapped Operator release new episodes?

The Bootstrapped Operator has 13 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to The Bootstrapped Operator?

You can listen to The Bootstrapped Operator on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts The Bootstrapped Operator?

The Bootstrapped Operator is created and hosted by Justin Comstock.
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