At its peak, Craigslist was generating over $1 billion a year with around 30 employees — outperforming Google and Facebook on revenue per employee by a factor of 10 to 20. Founder Craig Newmark turned down VC billions, refused to run ads, and demoted himself to head of customer service. Then the company lost more than 70% of its revenue. This is the rise and fall of Craigslist.
Monday, October 26, 2026
Wednesday, October 21, 2026
The Rise and Fall of MSN Messenger, the Chat App That Defined Online Life Before Social Media
MSN Messenger once defined online communication for an entire generation. From instant messages, custom statuses, emojis, and nudges to its eventual decline, this video explores how Microsoft’s iconic messenger rose to global popularity—and why it ultimately disappeared.
Friday, October 16, 2026
Yahoo!: The $125B Company That Burned Itself to the Ground
In the year 2000 Yahoo was worth $125 billion and was the front door to the entire internet. By 2016 it sold its core business for $4.83 billion — less than four cents on the dollar. Then the real story came out. A data breach affecting three billion accounts that the company had hidden for two years. A $35 million SEC fine. A deal price cut. And a Verizon rebrand that lasted exactly as long as it took for them to sell it again. This is the full story of how the company that could have bought Google for $1 million and Facebook for $1 billion spent twenty years refusing to answer one simple question — what is Yahoo? — until the market answered it for them.
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