Episode 817 | Bootstrapping in the Age of AI with Jason Cohen

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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Topics we cover: 

• (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

Links from the Show: 

• 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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