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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• (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

• 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!

Subscribe & Review: iTunes | Spotify

Could your business structure quietly cost you millions when you sell?

In this solo episode, Rob Walling answers listener questions about when QSBS might justify a C Corp (vs. staying an S Corp or LLC), why SaaS exits are often discussed in ARR multiples rather than EBITDA, and how the profitability/growth tradeoff impacts valuation. He also shares thoughts on GMV-based pricing and where developers can learn practical, non-fluffy marketing skills.

Episode Sponsors:

This episode is brought to you by Mercury

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• (3:30) – How the QSBS tax benefit can save you millions
• (7:40) – C Corp vs. S Corp: which structure makes sense for founders
• (9:39) – Why ARR multiples matter more than EBITDA in SaaS
• (13:13) – Profitability as a drain on growth
• (17:48) – Should co-founders join the same mastermind?
• (19:16) – How to leverage GMV-based pricing in SaaS
• (22:48) – The best way for developers to learn real marketing skills
• (31:28) – Why every founder should master sales and marketing early

• TinySeed Applications Live Q&A - February 11th, 10:00 AM EST
• Apply to TinySeed - Applications are until Feb 17th, 2026
• The SaaS Playbook by Rob Walling
• MicroConf - Community for SaaS Founders
• Conversion Factory
• TinySeed Mentors
• Rob Walling on X (@robwalling)

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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Is perfectionism quietly sabotaging your career or startup dreams?

In this episode, Rob Walling talks with his brother, Russ Walling, about the mindset and habits that shape long-term success from overcoming perfectionism to building resilience and learning to make tough calls without all the answers.

They discuss how growing up with a shared emphasis on hard work, sports, and achievement created both strengths and struggles and how lessons learned in construction, poker, and entrepreneurship still apply to building great companies today.

Episode Sponsor:

Hiring engineers shouldn’t feel like sorting through AI-polished resumes.

G2i cuts through all of that. They’ve pre-vetted over 8,000 engineers, all with 5+ years of real experience, and they run live, human-led technical interviews to verify actual skills.

No time wasters. No guesswork. Just solid developers who can deliver.

G2i is trusted by companies like Meta, Microsoft, and countless bootstrapped founders who need to move fast without making expensive mistakes.

Get a 7-day free trial and $1,500 off when you mention Startups for the Rest of Us at https://www.g2i.co/rob

• (04:10) – How early lessons in hard work and sports shaped mindset
• (07:46) – Learning to be comfortable being uncomfortable
• (12:03) – The dark side of perfectionism
• (16:51) – Overcoming fear of failure and learning to take risks
• (19:04) – What poker taught Russ about risk and decision-making
• (21:52) – The Armageddon Beer story
• (28:53) – Why both brothers chose entrepreneurship
• (31:08) – Redefining leadership: collaboration over fear
• (35:24) – The three traits that drive lasting success
• (43:45) – Why hard work is still the ultimate differentiator

• Discretion Capital M&A Advisory for SaaS Founders doing $2-25M
• The SaaS Playbook by Rob Walling
• Rob Walling (@robwalling) | X

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