Bold Go-To-Market Tactics: Just Evil Enough to Win with Alistair Croll

What if the biggest risk in your business isn’t building the product but realizing no one wants it? In this Unlearn episode, I’m joined by Alistair Croll, technologist, entrepreneur, and bestselling author of Lean Analytics, for a candid and clever conversation on rethinking product development, marketing, and demand generation.

Alistair’s work focuses on data-driven innovation and human behavior. He co-authored Just Evil Enough: The Subversive Marketing Handbook, a playbook for bending the rules to win in the attention economy. He has chaired global tech conferences like O’Reilly’s Strata and currently leads Startupfest, where he helps founders turn clever ideas into competitive advantage.

Known for blending insight with humor, Alistair unpacks why subversive creativity, not perfection, often wins. From the “fluency equation” to Burger King’s clever customer acquisition tactics, he reveals how unconventional strategies generate meaningful traction. This episode explores the science of subversive marketing, reframes how we think about product launch risk, and dives into the mindset shifts leaders need to stay relevant in the AI era.

Key Takeaways

• Start with Attention, Not Execution: The first job is proving demand, not building features.
• The Fluency Equation: Adoption is driven by desire, but also requires lowering inexperience, complexity, and perceived consequence.
• Redefine Product-Market Fit: Medium fit — how people find, try, and pay — is just as important as what you offer.
• Reverse Your GTM Strategy: Work backward from demand instead of forward from the product.

Additional Insights

• Test Before You Build: Demand validation should come before development or scaling.
• Have a Disagreement with the World: Bold startups are born from challenging norms, not just meeting expectations.
• Use Familiar Behaviors to Drive Adoption: Anchoring new tools to existing habits lowers friction and boosts engagement.
• Practice Ethical Persuasion: Subversive tactics work best when they respect users and build long-term trust.

Episode Highlights:

00:00 – Episode Recap

Alistair reframes startup risk with a clever hand-raising test: building isn’t the danger, indifference is.

03:16 – The Beach-Read Business Book

Why Just Evil Enough was built to entertain and educate, and how surprise fuels learning.

07:30 – The Real Startup Risk

Most teams focus on building because it feels safe. But the real risk is customer indifference.

08:41 – Subversive Marketing in Action

The Whopper Detour: How Burger King used playful tactics to achieve strategic goals.

13:20 – The Fluency Equation Explained

A new way to understand user hesitation and remove behavioral friction.

19:14 – AI, Fluency, and Leadership Gaps

Why executives aren’t using AI, even when they know they should.

26:00 – Decision-Making Matrix for Innovation

A two-by-two framework to help teams run smarter experiments with lower risk.

31:01 – The Fourth Miscapitalization

Why companies are still over-investing in engineering in an AI-native...