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Startups For the Rest of Us

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

31 min episode · 2 min read
·
Owner-level Thinkers

Episode

31 min

Read time

2 min

Topics

Career Growth, Remote Work, Investing

AI-Generated Summary

Key Takeaways

  • Compensation benchmarking: Owner level thinkers in North America command roughly $80,000–$90,000 when they are on the cusp of developing the skill, rising to low-to-mid six figures for proven operators. Bay Area-based senior individual contributors can reach $500,000 including equity, so geography dramatically shifts the budget required to hire at this level.
  • Sourcing strategy: Post on job boards, promote through owned email lists and social channels, and engage a specialist recruiter — Rob uses Remote First Recruiting by Dan and Ian — while simultaneously activating your network for warm referrals. Most owner level hires at TinySeed came through a combination of both channels, not exclusively one.
  • Identifying potential over proven track record: During interviews, ask candidates to detail specifically what they personally drove on past projects versus what their team delivered. Probe for budgetary authority, autonomous decision making, and six-to-twelve month forward planning. Former startup founders who applied to job postings are a strong signal worth prioritizing in screening.
  • Hiring for trajectory, not current level: Many strong hires start as project level thinkers and develop into owner level thinkers over one to three years when given responsibility and autonomy. Hiring someone on that cusp costs less upfront. The risk is that potential never materializes, so build in a sixty-day trial period to evaluate real day-to-day performance before full commitment.
  • Retention through compelling vision: Owner level thinkers can work anywhere, so founders must actively sell the role. Articulate a concrete two-to-five year company vision, highlight team quality, and consider equity as a retention mechanism. At Drip, remote work plus visible product traction made the company a sought-after employer before it could afford premium salaries.

What It Covers

Rob Walling defines three worker archetypes — task, project, and owner level thinkers — then answers listener questions about how to find, compensate, and evaluate owner level thinkers for small bootstrapped companies, drawing on his own hiring experiences at Drip, MicroConf, and TinySeed over six companies.

Key Questions Answered

  • Compensation benchmarking: Owner level thinkers in North America command roughly $80,000–$90,000 when they are on the cusp of developing the skill, rising to low-to-mid six figures for proven operators. Bay Area-based senior individual contributors can reach $500,000 including equity, so geography dramatically shifts the budget required to hire at this level.
  • Sourcing strategy: Post on job boards, promote through owned email lists and social channels, and engage a specialist recruiter — Rob uses Remote First Recruiting by Dan and Ian — while simultaneously activating your network for warm referrals. Most owner level hires at TinySeed came through a combination of both channels, not exclusively one.
  • Identifying potential over proven track record: During interviews, ask candidates to detail specifically what they personally drove on past projects versus what their team delivered. Probe for budgetary authority, autonomous decision making, and six-to-twelve month forward planning. Former startup founders who applied to job postings are a strong signal worth prioritizing in screening.
  • Hiring for trajectory, not current level: Many strong hires start as project level thinkers and develop into owner level thinkers over one to three years when given responsibility and autonomy. Hiring someone on that cusp costs less upfront. The risk is that potential never materializes, so build in a sixty-day trial period to evaluate real day-to-day performance before full commitment.
  • Retention through compelling vision: Owner level thinkers can work anywhere, so founders must actively sell the role. Articulate a concrete two-to-five year company vision, highlight team quality, and consider equity as a retention mechanism. At Drip, remote work plus visible product traction made the company a sought-after employer before it could afford premium salaries.

Notable Moment

Rob reveals that TinySeed and MicroConf — a nine full-time, two part-time person team — manages $60 million in assets, has invested in 210 companies, and runs multiple events and programs simultaneously, attributing this output entirely to hiring a small number of exceptionally skilled people rather than scaling headcount.

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Episode Transcript

When I first started my career, I was a task level thinker. I just couldn't do multiple things at once. 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 to the point where I was really comfortable running projects, and I think I became a a solid project level thinker at that point. And then as I dipped my toe into becoming an entrepreneur, I wasn't an owner level thinker because I needed too much certainty. I couldn't make hard decisions with incomplete information. I didn't know how to do that. And then it took me another five to eight years to really feel into it and to to be confident in my own ability to trust my founder gut and to develop my founder gut to the point where I was making good decisions because that's what being an owner level thinker requires. Welcome back to another episode, Startups with the Rest of Us. I'm your host, Rob Walling. And in this episode, I'm gonna dive into themed listener questions. 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 robwalling.com. If you enter your name and email in any of the forms on that site, you can start receiving a weekly thought from me. And some of these are mental models, they're frameworks, they're questions that I'm often asked by founders, whether that's from tiny seed on this podcast, in the micro comp community direct via email. And most of these are concepts that I have not covered in a prior book. Some of them are concepts that I've developed here on this podcast or am developing on the podcast. And I realized that I'm putting out a ton of audio content every year, a ton of video content on youtube.com/@robwalling, but I haven't really done serialized written content in quite a long time. And I decided that I wanted to double down on that modality this year because I feel like there are a lot of folks who maybe don't wanna listen to audio or video, and the way they learn best is through written content. So if you head to robwalling.com, you'll hear a new thought from me every week. As I've been doing this, though, it's been this great feedback loop because I'm sending out these emails and receiving a lot of questions about them. And when it's as easy as just hitting reply to an email and shooting me a question, I feel like I get a lot more questions about the topics. I'm also getting a lot of thanks, and I'm glad you're writing again, which makes me feel really motivated and, makes me feel grateful to have such an awesome community. But recently, I sent out an email about task level, project level, and owner …

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  • drawing on his own hiring experiences at Drip, MicroConf, and TinySeed over six companies
  • SPONSORS: Discretion Capital
  • engage a specialist recruiter — Rob uses Remote First Recruiting by Dan and Ian
  • drawing on his own hiring experiences at Drip, MicroConf, and TinySeed over six companies
  • drawing on his own hiring experiences at Drip, MicroConf, and TinySeed over six companies

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