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  1. The Best One Yet
  2. 🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters
🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet · Nov 10, 2025

Expedia's travel boom defies economic gloom, Duolingo's stock tumbles as its owl gets tame, and the corporate vest's surprising history.

The corporate vest's popularity stems from a psychological need to signal professional belonging

The vest has become a uniform in finance and tech because it's one of the few items of clothing that can be acceptably branded in a corporate setting. It acts as a "wearable business card," silently communicating one's company, industry, and status, fulfilling a deep-seated human desire to belong to a tribe.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago

Financial regulations limiting client gifts to $100 inadvertently fueled the corporate vest trend

A key driver of the corporate vest's popularity in finance was a regulation capping client gifts at $100. A high-quality, branded vest priced just under this limit (e.g., $95) became the perfect compliant, yet desirable, corporate gift, accelerating its adoption as an industry status symbol.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago

Sweetgreen sells its core robot tech, shifting from owner to client of its own innovation

Sweetgreen sold its core robotic salad-making technology, the "Infinite Kitchen," to another company for a significant profit. Sweetgreen will now be a customer of the technology it created and sold. This strategic move allows it to focus on its core restaurant business while benefiting from a specialist company scaling the automation.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago

Absurd AI, like a dog-hosted podcast, gains faster adoption than human-mimicking AI

People are wary when AI replaces or pretends to be human. However, when AI is used for something obviously non-human and fun, like AI dogs hosting a podcast, it's embraced. This strategy led to significant user growth for the "Dog Pack" app, showing that absurdity can be a feature, not a bug.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago

Duolingo's slowing user growth proves its social media team is its most valuable asset

When Duolingo paused its "unhinged" owl mascot social media strategy, daily active user growth saw its smallest increase in years. This direct correlation demonstrates that for some consumer apps, the social media team can be as crucial for growth as the engineering team, justifying top-tier compensation.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago

A CEO's internal AI memo can create public backlash that tanks key user metrics

Duolingo CEO's internal memo prioritizing AI over hiring sparked a public backlash. The company then paused its popular social media to cool down, which directly led to a slowdown in daily active user growth. This shows how internal corporate communications, when leaked, can directly damage external consumer-facing metrics.

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters thumbnail

🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

The Best One Yet·3 months ago