Boom or Bust

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.

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.

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.  

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 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.

Discover how Jeff Bezos turned a garage startup into a global empire. From selling books online to dominating cloud computing, retail, and even space, this episode explores Amazon’s bold vision, relentless innovation, and the lessons behind its meteoric rise.

In 1985, Coca-Cola changed its iconic formula—and sparked nationwide outrage. This episode unpacks the bold move, the backlash, and the powerful lessons in brand loyalty, customer trust, and the danger of messing with a classic.

From college dropout to billionaire, Melanie Perkins defied the odds to build Canva — the design platform that took on Adobe and won. Discover how a simple idea born in a living room became a $40B global tool used by millions. Grit, vision, and purpose turned frustration into innovation. This is the story of Canva — and the woman who gave design to everyone.

Elizabeth Holmes promised to revolutionize healthcare with Theranos—a device that could run hundreds of tests from a single drop of blood. Investors poured in millions. But the tech didn’t work. In this episode, we unpack the rise, deception, and downfall of Theranos, and the critical lessons in governance, ethics, and startup culture. A cautionary tale for founders, investors, and dreamers alike.

Blockbuster ruled the video rental world—until Netflix came along. In this episode, we break down how Blockbuster’s failure to adapt led to its $6 billion collapse. From ignoring Netflix to clinging to outdated models, discover the lessons every business should learn from its fall.