Every founder's pitching freemium right now — but Dropbox and Spotify are both "freemium," and only one of them can actually afford it. This episode breaks down five conditions that separate freemium businesses built to last from the ones quietly bleeding out: who you're really targeting, what a free user costs you, why they'd ever convert, what they give you before they do, and whether you can survive long enough to find out if any of it works.

A strategy lesson from Wix on why the best growth adjacencies often emerge by following the customer’s next problem—not the company’s existing capabilities.

Why the careers page nobody trusts matters less than the reputation nobody controls — a HubSpot case study on employer brand vs. employer reputation, and why the gap between them is now a business strategy problem.

Most workplace perks don't fix bad jobs — they just make them easier to tolerate. A short, sharp look at the difference between culture initiatives that improve the work and ones that just numb it.

This episode unpacks why leaders keep getting self-disruption wrong — treating it as a test of courage when it's actually a test of readiness. It walks through the core paradox.

A metric that once measured what customers wanted can quietly stop meaning anything — this episode unpacks the one question that reveals whether your pricing model is still tracking value, or just tracking effort.

Why doing the wrong thing brilliantly is more dangerous than doing it badly — and the one-line test that catches it before it's expensive.

Every strategy starts as a bet — testable, revisable, disposable. Then, if it works long enough, something quiet happens: it stops being a bet and becomes who the company is. From HubSpot's INBOUND-to-UNBOUND rename to Kodak's buried digital camera, this episode looks at the moment a winning strategy turns into a cage — and why success, not failure, is what locks the door.