Lesson learned from my biggest business mistake

My biggest mistake (at least in terms of income avoided) was not believing in the world wide web in 1994.

It’s not like I didn’t know about it. I had written a book called "Best of the Net". I’d even written the cover story for some now-defunct magazine on how to surf the internet. But in those days, the Net referred to Archie and Veronica and the online services… there was no real browser, no search engines to speak of, just a bunch of conferences and some guys in the Valley.

Not only did I ignore it, I actively ignored it. I didn’t register hundreds of domain names or build out the website for Yoyodyne beyond much of a placeholder. Instead of expanding my online game show/promotions company into the web, we focused on Microsoft’s Chicago service and Apple’s eWorld. Sigh.

Instead of building a search engine, I wrote a book called The Smiley Dictionary. Earnings to date: $10,000 or so.

I’m going into all this painful detail to let you know what an idiot I was. How many clues were just sitting there, how much access I had, how deliberate I was in ignoring them.


I think the answer is simple: Because the rules of this new business didn’t match the rules of my existing business.

Businesses live in ecosystems. A series of rules and assumptions that, taken together, make a thriving mechanism

Example: The oil ecosystem involves prospecting, drilling, transporting, refining, etc. If you don’t understand the role of automobiles or plastics in the oil industry, then you don’t understand the industry. You don’t ‘get it.’ On the other hand, if you understand the ecosystem of automobiles and of oil, then the ecosystem of windmills on homes and hydrogen in cars may be just too weird to grasp.

The ecosystem of the worldwide web was just being filled in. It had some assumptions clearly laid out (no money to view the content) and some waiting to be sketched in (can attention turn into cash?). But for someone in the business of selling books and internet content, this seemed impossible. Different rules, rules I didn’t understand and couldn’t accept.

And that’s where we get stuck. We get stuck because we believe that the rules of our ecosystem are permanent and transferable. In fact, they are almost always temporary and rarely transferable.

My approach now is simple: take a look at the rules of the new ecosystem. Do they make sense? Is it possible they’ll come to pass? If they do, what happens to you?