Eeke de Milliano

Eeke de Milliano built product at Stripe, one of the most admired companies for pricing strategy, and later at Retool. His perspective on pricing reversibility comes from watching two companies that experimented relentlessly with their own business models. Their core argument: Stop overthinking -- pricing is not a trapdoor decision, so pick a model and iterate. The evidence is specific: Stripe: Classified pricing as a two-way door, allowing rapid iteration; classified titles as a trapdoor, requiring deliberation. Furthermore, retool: Experimented with pricing tiers and packaging without treating each change as existential. In Eeke de Milliano's own words: "A lot of people, for example, think pricing is a trapdoor decision. But actually, it's really easy to grandfather your existing users into some existing pricing model and change pricing for future users." (Explaining the one-way-door vs. two-way-door framework applied to pricing.)

Having worked at Stripe during its formative years — a company famous for both pricing innovation and rigorous decision-making — de Milliano has firsthand experience with how the world's most respected fintech operationalized the trapdoor vs. two-way-door framework for pricing decisions. Their core argument: Pricing is reversible — don't agonize, experiment quickly. The evidence is specific: Stripe's title system — famously giving almost everyone the title 'product manager' because titles are a true trapdoor decision that can't be reversed. Furthermore, stripe's writing culture where business reviews, strategy memos, and product reviews were all written documents, cultivating clear thinking. The Amazon one-way/two-way door framework that Stripe operationalized — being rigorous about identifying which decisions truly are irreversible. In Eeke de Milliano's own words: "A lot of people, for example, think pricing is a trapdoor decision. But actually, it's really easy to grandfather your existing users into some existing pricing model and change pricing for future users." (On the reversibility of pricing decisions.)