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.

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• (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.

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

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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!

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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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