Have you ever pushed so hard on an idea that you missed the signal to change direction?

In this solo episode, Rob Walling covers a wide range of topics and dives into three areas every founder should master: how to develop an editorial eye (or “taste”), the difference between persistence and obstinance, and why focus, not diversification remains the hardest, most valuable entrepreneurial skill.

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• (1:55) – How to develop an “editorial eye” (and why it matters for founders)
• (7:03) – When to get out of the way and let true experts lead
• (8:07) – Why your product must start with a real problem (not just an idea)
• (9:11) – Paul Graham’s The Right Kind of Stubborn: persistence vs. obstinance
• (12:03) – Are you attached to your goal or just your first idea?
• (13:44) – How great founders adapt to new data without losing momentum
• (14:44) – Sam Parr on why “constant switching will kill you”
• (16:30) – Focus as a founder’s hardest and most valuable skill
• (16:49) – Why “Triple, Triple, Double, Double” isn’t dead (despite VC takes)
• (18:34) – The problem with clickbait startup advice

• MicroConf Europe 2026 – Join us in Reykjavík, Iceland (Sept 21–23) - Promo Code: ROB50
• The Mom Test by Rob Fitzpatrick
• Paul Graham: “The Right Kind of Stubborn”
• Sam Parr (@thesamparr) | X
• Harry Stebbings (@HarryStebbings) | X
• Rob Walling YouTube Channel
• The SaaS Playbook

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 | <...

Can your 9-to-5 job secretly prepare you to be a founder?

In this solo episode, Rob Walling shares 11 unexpected lessons from his own day jobs, from courier to electrician to engineering manager, and how each role quietly taught him skills that shaped his success as a SaaS founder. He dives into the value of curiosity, self-education, and learning to lead before you ever start a company.

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• (2:03) – Why every day job can teach entrepreneurial skills
• (4:44) – Lesson #1: Figuring things out when instructions are unclear
• (7:27) – Lesson #2: Learning to respect other people’s time
• (9:05) – Lesson #3: How early self-education compounds over time
• (11:33) – Lesson #4: Embracing hard, unglamorous work
• (14:09) – Lesson #5: Why experience always beats credentials
• (16:42) – Lesson #6: Letting the buck stop with you
• (17:44) – Lesson #7: Knowing when to cut corners (and when not to)
• (20:11) – Lesson #8: Finding the right people to work with
• (21:33) – Lesson #9: Managing and motivating people as a learned skill
• (23:53) – Lesson #10: Turning hiring and firing into Founder superpowers
• (26:11) – Lesson #11: The value of exposure to well-run systems

• MicroConf Mastermind Matching – Apply before January 16th
• The SaaS Playbook by Rob Walling
• Good to Great by Jim Collins
• Seven Habits of Highly Effective People by Stephen R. Covey
• Think and Grow Rich by Napoleon Hill
• MicroConf
• 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!

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What’s it take for a bootstrapped SaaS to beat a competitor with $10M in venture funding?

In this episode, Rob Walling talks with Laura Roeder, founder of Paperbell, about how her lean, fully-bootstrapped team outlasted and outperformed a VC-funded rival. They discuss what the venture-backed company got wrong, how Paperbell focused on the right customers, and why efficiency still beats funding.

• (3:52) – Competing against a $10M-funded startup
• (8:45) – Why “self-serve SaaS on hard mode” was worth it
• (14:36) – How over-investing in engineering killed their competitor
• (19:04) – The real problem with under-investing in marketing
• (21:19) – Why some SaaS markets can’t scale upmarket
• (24:13) – Why some markets are perfect for bootstrappers
• (28:42) – How big funding rounds create false signals
• (30:24) – The behind-the-scenes of a potential acquisition deal
• (33:26) – How Paperbell became the market leader

• MicroConf Mastermind Matching
• The SaaS Playbook by Rob Walling
• Paperbell
• Laura Roeder (@lkr) | 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