The History of the Dot Com Era

I graduated from college in 1997. While at college, the Netscape IPO, Yahoo IPO, eBay IPO, and Amazon IPO all happened. When I graduated, I couldn’t wait to go join this incredible time and be part of creating the next future of the internet. I moved to Seattle and joined a private company called Progressive Networks. It quickly changed its name to RealNetworks and went public in November of that year. (The one and only time I’ve worked at a company when it went IPO!) I lived the ups and downs of the Dot Com bubble — watching companies come on the radar, have white-hot IPOs, and then crash and burn even faster.

I have recently been talking to a number of founders and co-workers about this era and realizing that (a) I’m now old and (b) how few of them were in the industry, or even aware of what was going on then. One recently reminded me he was 4 years old in 2001.

It was such a fun and wild time. Companies like Lycos and TheGlobe.com became multi-billion dollar entities on hope, promise, and revenue from selling products to each other and back. As big as the tech / internet bubble was, the telecom bubble was even bigger with higher highs and higher lows, and much of the over-investment in capacity has been utilized time and again since then (and got really cheap for a few years in between too).

Most things that felt like hype back then, are realized today. Technology and the internet are truly mainstream. Billions of people have connected to the internet in the past hour. Instead of it just being about potential, there are now many trillion-dollar and multi-hundred-billion dollar companies that we depend on almost like core infrastructure now.

But, what’s similar is the belief in the future being much bigger than today, and people around us making gobs of money. In some ways crypto feels the most similar to the dot com hype era — where we talk a lot more about the potential, even if the usage isn’t quite there yet. I do wonder what are the Amazon, Yahoo, eBay, and Google in the crypto world today. And this applies to other really important future areas like space, autonomous vehicles, and more.

I wanted to see if there were any great books or movies to dive in deeper so I asked on Twitter and assembled the results below:

Books:

Non Fiction Overviews:

• How the Internet Happened by Brian McCullough — a great overview on the development of the internet and what the Dot Com era accelerated

Non Fiction Collections of Stories:

• F’d Companies by Philip Kaplan — Philip’s website FuckedCompany.com had all the gossip and stories in that era
• The New New Thing by Michael Lewis — focused on James Clark and a few related stories
• Nudist on the Late Shift by Po Bronson — a collection of iconic stories from the era
• Once You’re Lucky, Twice You’re Good by Sarah Lacy — a collection of stories from Web 2.0 founders who came out of the bubble

Non Fiction Focused Stories:

• There Must Be a Pony in Here Somewhere: The AOL Time Warner Debacle and the Quest for a Digital Future by Kara Swisher
• eBoys by Randall Stross — the story of Benchmark and the VC industry
• How to Castrate a Bull: Unexpected Lessons on Risk, Growth, and Success in Business by Dave Hitz — the story of NetApp and more
• Boo Hoo: A Dot Com Story — how Boo.com burned $135M in one year

Fiction:

• Bleeding Edge by Thomas Pynchon
• Moral Hazard by Kate Jennings

Blog Posts:

• Tren Griffin on the Dot Com Boom and Bust
• Tren Griffin on the Telecom Bubble

Movies & Documentaries:

Overviews:

• What Happened - 2001 Documentary — shared by Mark Cuban

Stories of Specific Companies:

• Startup.com — the story of GovWorks (pay your government bills online!)
• E-Dreams — the story of Kozmo.com (just like Doordash today)
• Riot On! — the story of Riot Entertainment (an early mobile phone)

One thing that surprises me a bit is there aren’t more iconic books or movies made about that era. One reason I suspect is that while the dot com peak was hit in March 2000 and it started falling hard from there, it wasn’t until the tragic events of 9/11 that the era really felt closed. That was such a transformational event I think there have been a lot more content created about that instead. That day still was the most transformational moment of my lifetime until the COVID pandemic.