In the comments to my post about people who think that all I do is beg for money on the Internet, Fallingwater asked:
Do you think a single, low-expense person can actually, really make a living with a site such as yours in 2012? I'm talking referrals, sponsorships and such, not living off donations (not that I'd mind, but I think you'd need a Wikipedia-like amount of readers, and possibly Jimmy Wales' creepy face, to pull that off).
I think you definitely can, even without staring into the soul of everybody who visits one of the most popular Web sites ever.
(Should I decide to try that, I would of course use...
...this picture.)
That doesn't mean it's easy to make money with a Web site these days, though.
The main problem is that there's no way for a review site or similar enterprise to make a decent amount of money from the beginning. If it's a review site, every review can make you a small but non-trivial amount of money for the first week or so of its life, and then long-tail off into cents per day. But if you've got a thousand pages each making you 15 cents a day, you'll be doing OK. When you've only made it to the 50-page mark, though, you could easily be grossing no more than 25 bucks a day, which ain't gonna pay the rent in most of the Western world.
If you're in Africa or eastern Europe or something then this could of course still be a very workable proposition, but making affiliate deals with local businesses, generally on a per-sale basis, is a major way for small sites to get going, and local businesses in Uganda have a lot less money to throw around. There may also be major obstacles to getting money from richer countries sent to you in a poor one; I don't know.
I have always had it very easy. This is partly because I was smarter with my money during the dot-com nonsense than some of my friends. (Shiny new car and inner-city apartment? Nope, I'll go with rusty used car and living with mum, thanks. I did blow a surprising amount of money on this toy, though - brushless motors were EXOTIC back then.)
My easy ride was also partly because I for some reason am good at writing, and at understanding computers.
(I think Michael Bywater was partly responsible for this. He wrote the computer column in Punch in the eighties, giving me the chance to read comedic writing about Lotus 1-2-3 when I was a small child with absolutely no understanding of what this software actually did, but he also anonymously wrote the gonzo-ish "Bargepole" column, which I also didn't really understand but which connected some of my neurons in quite novel ways.)
I've had it so easy mainly because I was lucky, in the abstract sense of being born white and male in a rich country, and in the less abstract sense of just having job opportunities fall in my lap. The small publisher that was my first gig turned out to be based walking distance from my house (or, more accurately, from my mum's house), and my fairly brief gig with the Dark Lord Murdoch came via a headhunter. I think I had to ask one or two magazines to let me write for them, but mainly they asked me.
You don't need this sort of implausible good fortune to make a Web site that makes a modest but live-on-able amount of money, but you do need a way to ride out the period of time while you make the site big and well-known enough for that income to build.
To do this, presuming you're not already wealthy or a kid living at home, you need to start the site as a hobby in parallel with a real job. Preferably the kind of real job that lets you sneakily work on your Web site while you're there, which can actually be done legitimately if you're a parking-station attendant or late-night petrol-station cashier or something, so a significant portion of your job description is "sit right there, and remain awake".
You also, of course, have to come up with some sort of idea for your site that can make money. The mass affiliate deals like Amazon or eBay are unlikely to be adequate, even if you do loathsome Sell Sell Sell stuff, as described in books that use the word "monetize". You need more direct deals with advertisers and retailers to make it work, as I did with Dan's Data and Aus PC Market. I made decent money when I reviewed Aus PC products; I made not much when I reviewed stuff from elsewhere. (And no, I didn't sell the free review product when I was done.)
Because of this, Dan's Data does not make me much money these days, because I burned out on reviewing computer gear years ago, and Aus PC gear reviews were my principal money source. If I were still writing about cases and CPU coolers and monitors all the time then Dan's Data would by itself still make me a passable living, but I just couldn't face another PSU or video card after a while, so now Dan's Data makes pocket-money only.
If you can start a site that covers some niche that (a) isn't already utterly saturated with high-quality journalism (or whatever you plan to do) already, and (b) lets you hook up with a business or three for mutual benefit, you absolutely can still start and run a Web site for a living.
Hell, if you're good enough you can even make adequate money from plain old ads; that's how the superlative Rock, Paper, Shotgun works. They accept donations as well, but I only now discovered that, since their donation page is harder to find than my cunning combined e-mail/donation scheme.
(I think the excellence of Rock, Paper, Shotgun and numerous other big game-review sites qualifies that market as "utterly saturated with high-quality journalism"; I wouldn't pin too much hope on a new game-review site making its owner much money these days. If you write good stuff, though, you can at least count on sites like Rock, Paper, Shotgun and news sites like the extremely venerable Blue's News to link to you fairly often. Starting a site that competes with Blue's News, Slashdot and other news sites that've all been taking body blows just from direct review-site RSS feeds a while ago, then Digg and now Reddit is, needless to say, not likely to be an express train to boundless wealth.)