Reverse engineer. Blogger. Investor. Photographer Hiker. Kayaker.

Pinboard founderMaciej Ceglowski suggests demanding to pay for services that you like that might be free. In fear that free services that are popular are not sustainable. It is a great post. But it raises some questions from me.

How would paying for a service ensure it won’t sell out? Maciej suggests that free services are more likely to shut down “Because it’s hard to resist a big payday when you are rapidly heading into debt.” No doubt that is true but when is a big payday easy to resist? If I had been paying Gowalla a few bucks a month would they have turned Facebook down? I don’t know. But if they still decided to sell the company (or, more accurately liquidate the product and move the team) to Facebook I would have been both disappointed and out a few bucks.

In other words, paying for a service doesn’t ensure its longevity or that it will never change.

What about Twitter? I saw many people linking to Maciej’s post as being good advice and some even had shown how they added the ability to pay for their free services based on this thinking. However, no one has mentioned that all of us are using and advocating a free service that fits Maciej’s scheme just perfectly — Twitter is a rapidly growing free service.

Yes, Twitter shows us ads from time-to-time in the form of Promoted tweets, trends, and accounts. But unless you use the Twitter.com site you’ll rarely see these ads. And, I’m sure, they’re making money behind-the-scenes by giving businesses access to their “firehose” and more controls and analytics than traditional accounts get. But it is still free for the public to use.

What would happen if, say, tomorrow Twitter decided that all Twitter clients (third-party and official) had to show some fairly obtrusive ads or you’d need to pay a few dollars per month to use the service? I’d wager many would pay up. Many would leave. And their growth would slow. However, none of that would ensure that Twitter wouldn’t sell out to a company sometime in the future. Revenue makes Twitter look even more appealing to potential buyers than if they weren’t making money. Revenue, it could be said, makes a company even more likely to sell.

This leads to Maciej’s next suggestion. Build it yourself. Obviously not everyone can do that (or should do that). But that seems to be the best suggestion he made in his post. The only way to ensure a service will be around and not change is to build and maintain it yourself. But, what if it becomes popular and someone with deep pockets makes you an offer? Then where are you? Back at the beginning.