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.

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• (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!

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How would a 2x unicorn founder build his next startup with AI?

In this episode, Rob Walling sits down with Jason Cohen, founder of SmartBear and WP Engine, to talk about building billion-dollar businesses, the future of AI for founders, and what makes small companies thrive even when the odds are stacked against them.

They dig into the early days of WP Engine, how Jason develops his frameworks, why execution beats ideas, and Jason’s framework for identifying “hidden multipliers” small, systematic changes that make an outsized impact.

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

• (03:45) – The core idea behind Hidden Multipliers
• (09:24) – Writing as a way of thinking
• (12:34) – Why sharing your frameworks matters
• (14:14) – The origin of “Designing the Ideal Bootstrap Business”
• (18:10) – The hidden weak links in every startup
• (21:25) – De-risking and niching down effectively
• (24:56) – Why narrowing your focus expands your reach
• (26:24) – Building WP Engine in a commodity market
• (29:37) – Out-executing funded competitors
• (31:52) – Finding product–market resonance through pricing
• (32:40) – How brand actually develops
• (37:54) – Building in the age of AI: pitfalls and opportunities
• (41:52) – The three categories of AI startups today
• (46:02) – Why 10x improvement is the new baseline for differentiation
• (49:19) – The real moat in the age of AI

• MicroConf US 2026 – Portland, April 14–16, 2026 Promo Code: Rob50 for $50 off
• The SaaS Playbook
• PREORDER Hidden Multipliers by Jason Cohen
• Designing the Ideal Bootstrapped Business with Jason Cohen
• A Smart Bear Blog
• Jason Cohen (@asmartbear) | 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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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.

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

• (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: iTune...