I’ve since moved on to a broader range of subjects and interests, but for a decade or so my focus was technology, both dabbling in and writing about. My college was UC Santa Cruz, just over the hill from Silicon Valley, and it wasn’t hard to feel the gravitational pull of the personal computer revolution. Fresh out of school, my one and only non-editorial job was at Apple Computer, debugging software for printers (which I promptly used to publish a magazine on the side).
In New York City I freelanced for local publications like the Village Voice and Flatiron, and wrote and published two computer books. This was in the early days of “new media,” when it was clear that some cataclysmic collision of publishing and technology was about to take place. Various publishers and other media types started wondering what their strategies should be. And since I happened to be around, they started asking me.

Director Demystified (Peachpit/Macromedia Press, 1999)
This morphed into a consultancy and “multimedia studio,” called Panmedia. At the same time I wrote another book about multimedia programming, which became the first volume in the bestselling Demystified series.
In 1995 we moved Panmedia–then a three-person shop–to the San Francisco Bay area, and quietly shifted our focus. The Internet was emerging as a medium of its own, and it made sense to focus on providing the message, or “content” (I still shudder at that hideous term). Our strategy was to give away free samples of information, proving that the web could be engaging and useful.
Our sample site was called Learn2.com–“the ability utility”. It was a continuously-growing compendium of step-by-step instructions (we called them “2torials”) on life skills and neat tricks. If you wanted to learn to spin a basketball, tie a bow tie, housebreak a puppy or remove a stain, we were there to walk you through the process. We took an irreverent tone, used cartoons rather than technical illustrations, and generally tried to make the learning process fun.
Seems like an obvious idea in retrospect, doesn’t it? But there was nothing like it at the time, and it caught on quickly. Between word of mouth and national media attention, Learn2 soon became one of the more popular sites on the web…and definitely the most popular provider of what was soon dubbed “e-learning” (remember those e-words?).

From the 2torial “Learn2 Tune a Guitar”
Our instructional inventory grew into hundreds, then thousands. Panmedia morphed into Learn2.com, Inc., and eventually Learn2 Corporation. We spawned a host of imitators, but curiously they all seemed content to copy only our free stuff, relying on advertising as their revenue base. We sold ads, but our real revenue was in designing custom content for clients like Oracle and Hewlett-Packard. We diversified into CD-ROMs, kiosks and intranets; we even published a Learn2 book (Villard) and developed a pilot for Learn2 TV.
I was considered a pretty eccentric CEO. Not because I had no prior business experience (baby moguls were everywhere) but because I didn’t accept venture capital, choosing instead to grow the business from its own profits. This made me the tortoise in a race with hundreds of hares. I remember at least one VC regarding me with genuine pity, shaking her head at how I’d failed to grasp the rules of the game. But I didn’t see the need for venture capital, or for the second-guessing it would bring.

The Learn2 Guide (Villard/Random House, 1998)
By 1999, after a series of mergers and acquisitions, Learn2 was a public company, trading on NASDAQ and selling more retail interactive instruction than any other company (Microsoft, in this category at least, was in second place, no doubt because it wasn’t a priority for them). We had more than 300 employees, a half-dozen offices and some serious management. I had already relinquished the CEO position to the former COO of Lehman Brothers, although I retained a fancy title (Chief Internet Officer) and a seat on the Board of Directors.
But it was time to go. I wasn’t an entrepreneur–I had just wanted to write and publish cool, useful stuff, stuff that entertained people and made their lives easier. That was still what excited me, and my restlessness started to show. So I left, on cordial terms and with the blessings of the board, in March of 2000. The techno meltdown began soon after, but by then I was watching from the sidelines.

One of our shelf products, circa 2000.
I was proud of what we’d accomplished, particularly when Yahoo named us one of “the twelve most important websites of the 20th century”. It was deeply satisfying to walk into a store like Office Depot and see Learn2 products gleaming on the shelves, or to surf over to the website and see the knowledge base continue to grow.
Like most of Internet 1.0, Learn2 has faded away. It was acquired by Oracle, which eventually shelved it and let some of the intellectual property expire (including the domain, which is now claimed by an entirely different business). Online instruction is, of course, now a genre in its own right. If I had to pick a site that best embodies the spirit of Learn2, it would be Instructables—community-based, irreverent, encouraging and empowering. Check it out.