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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.

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Check latest episodes from The Bootstrapped Operator podcast

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

2025/12/18

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/

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

2025/12/16

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.

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

2025/12/15

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

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

2025/12/14

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

The Five Practices Every Bootstrapped COO Needs to Lead Well

2025/12/13

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.

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

2025/12/12

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/

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

2025/12/11

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.

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

2025/12/10

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.

EOS in Real Life: Right People, Right Seats

2025/12/09

🔗 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

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

2025/12/08

💬 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

Deep Work: Your Secret Weapon as a Bootstrapped COO

2025/12/08

👋 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 here No fluff. Just real ops talk.

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

2025/12/07

🎯 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 LinkedIn No fluff. No hype. Just real execution talk.

The Quiet COO’s Guide to Better Conversations

2025/12/05

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-450a82a4 Let’s trade notes. No fluff. Just real ops.