There was a brief window in the late ’90s and early 2000s that might have been the most exciting time in history to be wired for technology.
Not because the tools were better. Most of them were terrible.
Because the rules didn’t exist yet.
The internet wasn’t an established industry. It was an open frontier. Having a computer in your house made you “techy.” Knowing basic HTML practically made you a wizard. And if you were curious enough to start building, you weren’t entering some mature ecosystem with entrenched winners and established playbooks. You were helping invent the ecosystem itself.
We tend to remember this period through the dot-com bubble: ridiculous valuations, companies with no revenue, fortunes made overnight and then erased just as quickly. That happened. But focusing on the bubble misses what was actually remarkable about the era.
A relatively small group of people stumbled into uncharted territory and started constructing the digital world we now take for granted.
The websites, protocols, marketplaces, search engines, communication tools and basic habits of internet life were being figured out in real time. Nobody knew exactly what the internet was supposed to become. That was the opportunity.
And what made the period so powerful wasn’t what builders had. It was what they didn’t have.
No app stores. No AWS. No Stripe. No Shopify. No mature ad networks. No recommendation algorithms deciding whether anyone would see what you made. No platform owner sitting above you changing the rules.
Just raw internet.
That sounds inconvenient today, and it was. Building anything required substantially more technical effort. But the difficulty came with an extraordinary tradeoff: freedom.
If you built something genuinely useful, there was a chance you could simply own the category. There weren’t 20 clones appearing six months later because everyone had access to the same APIs and cloud infrastructure. Entire pieces of internet real estate were sitting there unclaimed.
That world barely exists anymore.
Today, technology is dramatically easier to build and dramatically harder to own.
You can launch an application faster than ever, but you’re probably launching it through Apple or Google. You can reach billions of people, but Meta, TikTok or Google decides how cheaply you can reach them. You can build an e-commerce empire without touching a warehouse, but you’re likely sitting somewhere on top of Shopify, Amazon, Stripe or another company’s infrastructure.
Even when you’re building, you’re borrowing.
That doesn’t mean innovation is dead. Far from it. But the nature of the game has changed.
The early internet rewarded exploration because huge portions of the map were still blank. The modern internet rewards execution inside territory that has already been claimed.
That distinction matters.
Today, someone can build a technically impressive company and still spend most of their time negotiating with ecosystems they don’t control: app-store policies, search rankings, advertising costs, payment processors, cloud providers and algorithms. The infrastructure that makes building so easy also creates the walls around what you build.
The early internet was a frontier.
What we have now is a walled city.
And that’s why I think the people who caught that original window had one of the most interesting seats in technological history. They weren’t optimizing conversion rates inside somebody else’s platform. They were deciding what the platforms would be.
They arrived before the blueprints were written, before the highways were paved and before everyone realized how valuable the land was.
For a few strange years, the internet was empty space.
And everything was up for grabs.