Exploring the parallels between Dot-com era failures and the risk of today’s AI bubble — with an example of 5 Products that failed during the Dot-com bubble

Sushil
4 min readJun 20, 2023

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The parallels between the dot-com era and the current AI boom have sparked concerns about the potential risks of a bubble forming in the AI investment landscape. Just like in the dot-com era, where numerous companies emerged as pioneers of the internet age, the AI era has witnessed a surge in funding and valuations.

The craze that led to the dot-com bubble and the flood of capital that came with it resulted in many “back-of-the-napkin” business models becoming publicly traded companies almost overnight. Dot-com companies like Amazon.com Inc. (AMZN) and eBay Inc. (EBAY) adapted on the fly and survived the bust, but many others failed.

Let’s explore a few examples of companies that experienced remarkable valuations during the dot-com era but ultimately failed.

Pets .com

  • It was an online pet supply retailer that was founded in 1998 and received funding from big players including Amazon despite the Red flags of the company’s business model.
  • The company went public in February 2000 and raised $82.5 million in its IPO but filed for bankruptcy nine months later. The company appeared to have a flawed business model from the start, which included competition with pet stores and difficulty shipping large items, such as dog food bags.

Webvan

Webvan

  • Webvan was an online grocery delivery service that operated between mid-1999 and mid-2001. The company raised nearly a billion dollars from investors but went bankrupt after just two years of operations.
  • Webvan’s strategy of “growth at any cost” was characteristic of many failed Dotcom Bubble companies. The company lost over $800 million and shut down in June 2001, filing for bankruptcy and laying off 2,000 employees.
  • Webvan spent huge sums on high-tech warehouses that were designed to revolutionize distribution, but they turned out to be mostly a waste of money. The problem is that all the technology was meant to reduce labor costs, and labor is relatively cheap.

NorthPoint Communications

  • It was a competitive local exchange carrier focused on data transmission via digital subscriber lines. The company had relationships with Microsoft, Tandy Corporation, Intel, Verio, Cable & Wireless, Frontier Corporation, Concentric Network, ICG Communications, Enron, Network Plus, and Netopia.
  • In January 2001, NorthPoint filed for bankruptcy. Some internet service providers blamed the banks for failing to work out a deal to save the company.
  • In March 2001, AT&T Corporation acquired the assets of NorthPoint for $135 million in a liquidation

WorldCom

Worldcom

  • It was a telecommunications company that went bankrupt in 2002 after revealing an $11 billion accounting fraud that inflated its earnings and assets.
  • The fraud was initiated by its top executives, who faced criminal charges and prison sentences. The bankruptcy was the largest in U.S. history and shook the telecommunications industry.
  • WorldCom’s customers, including its MCI long-distance service, were not immediately affected by the bankruptcy. WorldCom settled with the SEC for $2.25 billion for civil fraud.

MP3.com

It was a music website that allowed users to download music for free. The company was founded in 1997 and went public in July 1999. The company was sued by several record labels for copyright infringement, which led to a settlement of $160 million. The company was later acquired by Vivendi Universal.

Boo.com

It was an online fashion retailer that was founded in 1998 and went bankrupt in May 2000. The company spent millions on advertising and marketing campaigns, but it failed to generate enough sales to cover its expenses.

boo.com

The dot-com bubble was a stock market bubble in the late 1990s that burst in 2000. The period coincided with massive growth in Internet adoption, a proliferation of available venture capital, and the rapid growth of valuations in new dot-com startups.

But, the AI boom is characterized by a focus on business fundamentals, with many AI companies already generating significant revenue and profits. Additionally, the AI market is more diverse than the dot-com market, with applications in a wide range of industries, from healthcare to finance to transportation.

However, some experts warn that the AI market is in a “baby bubble” and that a burst could occur if companies fail to prove their value proposition or if the Federal Reserve makes a policy mistake.

Overall, the AI boom is distinct from the dot-com era in its focus on business fundamentals and its potential to revolutionize industries.

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Thanks for reading :)

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Sushil
Sushil

Written by Sushil

I write Case studies or long stories on AI, Startups, & Tech.

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