The Dot Com Bubble Boys

The Dot Com Bubble Boys
2/3/25, 5:00 PM
In which I wish I had founded an internet platform company when I was two years old
Folks in my age bracket often joke that we should have bought houses when we were twelve years old. This would have been back when housing prices were depressed following the 2008 market crash. I can do them one better: I have deep regrets that I didn’t start an internet platform company when I was two.
In 1996, I was brought into the world teary eyed and mad. In retrospect, no wonder I was crying so much: I needed to get to the office, stat. The Dot Com bubble started in 1995, meaning I was already a year behind. All those tantrums I threw? My parents should have dropped me off in a cubicle in San Fransisco where I could have put my attitude to good use.
Right around the year I was born, Jeff Bezos was getting ready for Amazon’s IPO in May 1997. By 1998, Peter Thiel and Elon Musk had established PayPal and Larry Page and Sergey Brin had founded Google. PayPal’s sale to eBay in 2002 subsequently created the “PayPal Mafia” of Silicon Valley leaders who went on to found or fund other internet based companies, including Netflix, YouTube, and AirBnb.
Collectively, these twelve or so people have created trillions of dollars in market capitalization through the companies they've founded, led, or funded. Most of this success occurred between the year I stopped wearing diapers and the year where I could first do long division (jokes on you, I still can’t do long division).
Even at a regional level in Ohio, many of the investors I interact with today built their wealth through internet based software and innovations. They’ve permeated through the tech landscape, touting on LinkedIn and on Podcast after Podcast that they were, “early at SpaceX” or did, “ten years at Google.” And I think there is something about this moment that is enabling these particular types of bros - and they are mostly bros - to have outsized voices in policy, industry and venture capital today.
First, the stock market has been on a rampage. Anyone who built equity in tech stocks in the early 2000s is now sitting on generational wealth. And wealth breeds more wealth. It also breeds influence: people gravitate toward success, whether it’s deserved or not.
Even more important to this particular moment in time is what these founders learned about exponential growth during their early careers. The SaaS (Software as a Service) model emerged as an internet-enabled business structure, as the internet allowed for low cost distribution, viral adoption and scalability in ways that hadn’t existed previously. In any other industry at any other time, business owners were limited by barriers to scalability: the need for built infrastructure, inventory, or costly in-person marketing. In the SaaS universe, these challenges largely evaporate. Once a software is built, it can be sold to any number of people, with far reduced costs per unit.
Why does experience in exponential growth business matter now? Easy answer: AI. The wide scale adoption of artificial intelligence is occurring at breathtaking speed in the United States. To survive, existing companies and new companies alike are needing to innovate, disrupt and reinvent at a rate that hasn’t been seen since turn of the millennium. The highly competitive, fast paced nature of this moment present opportunities for the Dot Com Bubble Boys to flex their wealth and experiences. As a result: omnipresent opining from this cabal of tech executives about what the future can and should look like. And lots and lots of people are listening.
The Dot Com Boom made a handful of people staggeringly rich, but it also left us with a society where a small circle of technocrats now pick our presidents, dictate the economy, and crush competition under mountains of capital. Their success has granted them not just wealth, but the perception that they are uniquely suited to solve humanity’s biggest problems. And maybe they are good at scaling software. But running a company, even a trillion-dollar one, is not the same as running a democracy.
We are undeniably in the middle of an AI bubble. Much like the Dot Com era, there will be winners and losers, and when the dust settles, we’ll be left with the AI Autocrats: unaccountable, ultra-wealthy individuals who treat politicians like collectible action figures.
And it’s already happening.
Just last week, Elon Musk’s team walked into the Treasury Department and walked out with classified information, including the personal data of millions. On whose authority? His own, mostly, with a little help from the 119th Congress, who are either too enthralled or too spineless to push back.
The kind of power Musk is consolidating isn’t like Trump’s—it’s something far more entrenched, far less theatrical. It’s the kind of power no one gives up without a fight. And with AI poised to generate unprecedented wealth, we are barreling toward a new Gilded Age, where money—and therefore power—is concentrated at historic levels.
This consolidation of technological, political, and economic power in the hands of individuals like Elon Musk poses significant challenges to democracy and our social fabric. With no end in sight to the ascension of Musk’s corporate fascism, I can’t help but to believe that the AI Autocrats are already here.
The type of power Elon Musk is consolidating around himself today is not the same as the power gained by Donald Trump. It's the type of power that one does not give up without a fight.
Without a tax structure in place to account for the existing and soon to worsen wealth boom, concentration of money and therefore power in the United States is set to, very soon, reach an all time high. And without legislative and judicial checks and balances in place to curb the corrupting influence of absolutely power, I see no sane way for the madness to end.
This essay was not written by ChatGPT.