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  1. Startups For the Rest of Us
  2. Episode 817 | Bootstrapping in the Age of AI with Jason Cohen
Episode 817 | Bootstrapping in the Age of AI with Jason Cohen

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

Startups For the Rest of Us · Jan 27, 2026

Unicorn founder Jason Cohen on bootstrapping, niching to win, building brand through execution, and navigating the AI startup landscape.

Your Biggest Growth Levers Are 'Hidden Multipliers,' Not Big Budgets

Growth often comes from small, systematic changes that leverage how business or human nature works. These levers are 'hidden' not because they're unknown, but because their immense importance is underestimated or they aren't acted upon within existing teams and budgets.

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

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

Startups For the Rest of Us·24 days ago

Company Culture Can Be a Moat That Competitors Willfully Choose Not to Cross

WP Engine thrived in commodity hosting by emphasizing human support. This became a powerful moat because VC-backed competitors, culturally and financially focused on high software margins, would never copy a strategy that required expensive human capital, even if it worked.

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

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

Startups For the Rest of Us·24 days ago

In Crowded AI Markets, Win with Narrow Customer Focus, Not a Tech Moat

In a space like AI where everyone uses the same models and tech moats are rare, competing on technology is futile. The winning strategy is to ignore the competition, focus intensely on a narrow ideal customer, and build an amazing product vision tailored specifically to their needs.

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

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

Startups For the Rest of Us·24 days ago

De-Risk Your Startup by First Tackling Your Biggest Weakness, Not Your Strength

A startup's success depends on many factors working in concert. Founders often default to their strengths (e.g., an engineer building the product). The correct, de-risking approach is to first tackle the biggest uncertainty or personal weakness, such as customer acquisition.

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

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

Startups For the Rest of Us·24 days ago

Valuable Content Can Act as a 'Foil' to Help Readers Clarify Their Beliefs

The goal of thought leadership isn't just to be right. It's equally valuable to act as a 'foil,' presenting a clear viewpoint that helps others gain clarity on their own beliefs, even if—or especially if—they disagree with you. This solidifies their thinking and makes your content impactful.

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

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

Startups For the Rest of Us·24 days ago

Build AI Products for Experts Who Can Fix Its Flaws, Not for Novices

Since current AI is imperfect, building for novices is risky because they get stuck when the tool fails. The strategic sweet spot is building for experts who can use AI as a powerful but flawed assistant, correcting its mistakes and leveraging its strengths to achieve their goals.

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

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

Startups For the Rest of Us·24 days ago

A Brand Becomes a Moat Only When Customers Choose It Despite Negative Trade-Offs

A brand isn't just an identity; it becomes a competitive moat only when it directly influences purchase decisions. The true test is when a customer buys your product *because* of the brand, even if it's more expensive, has fewer features, or is otherwise inferior on paper.

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

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

Startups For the Rest of Us·24 days ago

Niching Down Attracts a Broader Market by Clarifying Your Product's Trade-Offs

Niching down doesn't limit your market; it clarifies your value proposition for an ideal customer. This extreme specificity about your product's strengths and weaknesses also appeals to a much larger adjacent audience, who can now confidently evaluate your trade-offs and decide to buy.

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

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

Startups For the Rest of Us·24 days ago

Position AI in Your Solution Space, Not the Customer's Problem Space

Founders often mistakenly market "AI" as the core offering. Customers don't buy AI; they buy solutions to their long-standing problems (e.g., more leads, better service). Frame your product around the problem it solves, using AI as the powerful new tool in your solution space that makes it possible.

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

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

Startups For the Rest of Us·24 days ago