Episode 820 | When to Quit Your Day Job, A.I. Feasibility Risk, and More Listener Questions (Rob Solo)

2026-02-17

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When do you finally quit your day job and go all-in on your startup? In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also breaks down how to treat a low-priced, high-churn plan as “cheapium,” when to kill it, and how to test freemium without making a decision you can’t undo. Want to get your question answered? Drop it here...

When do you finally quit your day job and go all-in on your startup?

In this solo episode, Rob Walling answers listener questions about when it’s worth taking funding to speed up your path to full-time, how to think about equity when a co-founder joins late, and whether A.I. is shifting startup risk from market risk to feasibility risk. He also breaks down how to treat a low-priced, high-churn plan as “cheapium,” when to kill it, and how to test freemium without making a decision you can’t undo.

Want to get your question answered? Drop it here.

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Topics we cover:

(2:48) – When is it time to quit your day job, and should you raise funding to do it faster?
(4:35) – The “emotional runway” problem (and why bootstrappers burn out)
(10:06) – Equity splits: when to talk about it, and what actually matters
(13:57) – Late co-founder vs. business partner: how traction changes the %
(18:34) – Is A.I. increasing feasibility risk (aka tech risk) for startups?
(25:01) – Should a cheap, high-churn plan be treated like a marketing channel?
(26:19) – “Cheapium” pricing: when to keep it, kill it, or test freemium

Links from the Show:

Apply to TinySeed - Applications are until Feb 17th, 2026
The SaaS Playbook by Rob Walling
MicroConf - Community for SaaS Founders
Slicing Pie by Mike Moyer
Die With Zero by Bill Perkins
Dharmesh Shah

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!

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