I wrote this for my bro Matt Johnson’s online selling how-to site. We’ve had fascinating conversations about bookselling and general online sales, how the web is changing business, future needs and trends, and how to provide genuinely useful content. This business article is actually a lengthy diatribe against the “mania for the present” thinking that pervades the marketing philosophy engulfing the web.
How we use the web, how we’re supposed to use it, how we’re being guided to use it is changing fundamentally. As the whole field becomes more optimized and polished, we are being oriented more toward a passive experience online rather than one we create.
Craigslist, for the most part, has remained the same as it ever was. Its ultimate utility was in nimbly catering to whatever people used it for, as its audience expanded out of the tech community, and out of San Fran to other major cities, and then, out of the United States. Craigslist’s sticky user experience seems quaint in a world where stagnation equals death. And it’s possible to be too nostalgic, of course. But Craigslist’s continued existence and success questions the “inevitable” speeding up of technological progress, whether it’s necessary, and whom it serves.
So what, if anything, can a young entrepreneur in online selling, or business creation, learn from Craigslist?
Craigslist is one of the few for-profit online companies I can think of that seems to operate on the basis that, once it has a good user base and income stream, all a company needs to do is maintain an equilibrium and work out problems as they crop up. This is antithetical to the almost religious idea that everything must keep getting better, an ideation that conveniently supports a rat-race ethos, and keeps expensive software engineers busy.
Any company or website might be a fad, riding out a trend, and so successful websites start to do things almost immediately to diversify their income and to avoid stagnation. Update early and often, and figure out what you’re doing as you go.
This has led to a culture of updating. Many, many companies offer very little in the way of actual services, they’re really just platforms, but they get into the wealth-creation mindset, leaving users cold with incessant upgrades, tweaks, ominously vague terms of use changes, and unintelligible licensing agreements. Forcing users to relearn how to use something every few months that was only ever supposed to be a cool or useful tool is not a clever business strategy. At least, not outside of the small echo chamber of those for whom tech is the end, and not a means.
But the point is that a lot of tricks used by people to make money online are now eroding confidence and ease of use to such an extent that people are wrestling with them and their impact on all of our lives. Being a profitable company is not itself a winning strategy for a product. Our nativity online was in connecting people, and helping people do what they wanted to do, making things easier, rather than bleeding people dry. Many companies are missing the forest for the trees.
Read the rest on How to Be an Online Seller.
I can’t wait to write about eBay next! As the Paypal/eBay split attests, much is in play in that company right now. It’s unlikely to be a love letter.
I have a theoretical bent of mind that turns basic things into thought experiments. I believe that almost anything in your life reflects everything in your life. So if that’s true, I like to look at more trivial aspects of my life to find balance. It’s easier to see the truth when you’re less invested.
Subscribe to at least one art/design blog, but not too many. Beware of product-heavy blogs, they encourage endless consumption. Many design blogs just repeat each other, so find a fairly original and varied one. 
