Boom or Bust

Booked & Built: How Airbnb Went from Air Mattresses to a Global Empire

Airbnb went from renting air mattresses to reshaping global travel. We unpack how a struggling startup battled trust issues, legal fights, and fierce competition — and came out on top. It’s a story of grit, reinvention, and the power of building not just a product, but a movement.

How KATSEYE’s GAP Ad Beat American Eagle

GAP’s viral “Better in Denim” ad featuring girl group KATSEYE took over TikTok, while American Eagle’s Sydney Sweeney campaign sparked backlash over its “great genes” tagline and unsettling historical echoes. In this episode of Boom or Bust, we break down the denim war of 2025, the controversy, and what it reveals about branding, culture, and timing.

Duolingo: How the Green Owl Lost Its Way

Once hailed as the king of language learning apps, Duolingo captured millions of users with its gamified lessons and iconic green owl mascot. But in recent years, cracks have started to show — from an aggressive freemium model to questionable AI-driven decisions that have many users concerned.

Yahoo: The Fall of the Internet Giant

Explore the dramatic rise and fall of Yahoo—once the internet’s gatekeeper. From missed billion-dollar acquisitions to strategic missteps, this episode unpacks how the tech titan lost its edge and what every business can learn from its decline.

Toys 'R' Us: The Fall of a Toy Empire

Toys "R" Us rose fast—and fell hard. From nostalgic glory to e-commerce missteps and financial collapse, discover the lessons behind one of the biggest brand failures in modern history.