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

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Jan 27, 2026

Jason Cohen, founder of WP Engine and SmartBear and author of Hidden Multipliers, shares sharp startup frameworks in plain language. He explains small, systematic changes that create outsized impact. He talks about writing to clarify ideas, niching to de-risk growth, winning against funded rivals through execution, and practical ways founders should approach AI today.

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INSIGHT

Small Changes, Big Returns

Hidden multipliers are small, systematic changes that create outsized results within existing teams and budgets.
Jason defines them as often-hidden improvements you can implement without massive new investment.

INSIGHT

Writing As Thinking

Writing helps Jason think and refine ideas by forcing clarity and iteration.
He drafts many ideas and only publishes those that survive reflection and practice.

ADVICE

De-Risk The Weakest Link First

Tackle your weakest startup assumption first to de-risk the business quickly.
If you can't answer how a weakness becomes acceptable, treat it as a potential deal breaker.

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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.

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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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