Episode 826 | How to Find, Hire, and Work with Owner-Level Thinkers

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9 • 819 Ratings

🗓️ 31 March 2026

⏱️ 32 minutes

🔗️ Recording | iTunes | RSS

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Summary

How do you find someone who thinks like an owner, not just a task-doer? In this episode, Rob digs into a batch of listener questions about task level, project level, and owner level thinkers. He covers how to identify them, what they cost, where to find them, and why building a team of exceptional people creates a virtuous cycle that lifts everyone up. Topics we cover: (4:13) – Defining task, project, and owner level thinkers (7:32) – Are owner level thinkers born or built? (10:16) – Compensation ranges for owner level thinkers (11:53) – W2 vs. contractor for senior hires (15:53) – Do you actually need owner level thinkers? (17:36) – Where to find project and owner level thinkers (20:16) – How long to integrate them into your company (24:40) – How to identify them in job interviews (29:38) – Why you won't always get hires right Links from the show: Rob Walling's Essays Rob Walling’s Newsletter Rob Walling YouTube The SaaS Playbook Remote First Recruiting MicroConf TinySeed SaaS Institute Discretion Capital If you have questions about starting or scaling a software business that you'd like for us to cover, please submit your question for an upcoming episode. We'd love to hear from you! Subscribe & Review: iTunes |Spotify

Transcript

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0:00.0	When I first started my career, I was a task level thinker.
0:03.0	I just couldn't do multiple things at once.
0:04.0	I couldn't prioritize. I couldn't manage it. I couldn't keep all the plates spinning. And then over the course of the first five-ish, six-ish years, I remember getting at the point where I was really comfortable running projects, and I think I became a solid project-level thinker point. And then as I dip my toe into becoming
0:21.7	an entrepreneur, I wasn't an owner level thinker because I needed too much certainty. I couldn't
0:25.8	make hard decisions with incomplete information. I didn't know how to do that. And then it took me
0:30.0	another five to eight years to really feel into it and to be confident in my own ability to
0:35.9	trust my founder gut and to develop my founder
0:37.6	gut to the point where I was making good decisions because that's what being an owner-level
0:42.2	thinker requires.
1:01.6	Thank you. Welcome back to another episode, start up to the rest of us.
1:06.8	I'm your host, Rob Walling, and in this episode, I'm going to dive into themed listener questions.
1:15.6	So if you don't know, I've recently started writing again, publishing essays, for the first time really since about 2011. And I'm doing that over at rob walling.com.
1:18.6	If you enter your name and email in any of the forms on that site, you can start receiving a weekly thought from me.
1:26.6	And some of these are mental models, their
1:30.0	frameworks, their questions that I'm often asked by founders, whether that's from Tiny
1:36.2	Seed on this podcast, in the microcomf community direct via email. And most of these are concepts
1:42.8	that I have not covered in a prior book. Some of them are
1:46.3	concepts that I've developed here on this podcast or am developing on the podcast. And I realize
1:52.0	that I'm putting out a ton of audio content every year, a ton of video content on YouTube.com
1:57.9	slash at Rob Walling, but I haven't really done serialized written content in
2:04.1	quite a long time. And I decided that I wanted to double down on that modality this year
2:10.7	because I feel like there are a lot of folks who maybe don't want to listen to audio or video
	...

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