There are three main reasons that I like entering into bets with people. The first is, simply, that it’s fun. The second is that I love to win bets. And the third is that I love to lose them. I don’t ever trade the markets: all of my investments are strictly buy-and-hold, with a time horizon measured in decades. That rule has saved me a lot of money over the years, not that I ever had much inclination to trade in the first place. But it has also prevented me from learning the kind of lessons that all traders learn early and often.

For pundits, it’s easy to be wrong: in many ways, it’s what we’re paid for. If what you want is facts and certitude, stick to old-school journalism. But it’s much harder for us to learn from our mistakes, precisely because the cost of being wrong is in many cases negative. So when I get the opportunity to express a conviction in the form of a wager, I tend to jump at it, partly because it’s one of the very few ways for me to be forced to admit that I was wrong about something, and to ask myself what the lessons are.

All of which is a very long-winded way of saying that I’ve gone and lost another bet, much to the delight of Elizabeth Spiers. She’s firmly ensconced at the helm of the New York Observer, a year after being given the job; I said she wouldn’t be. I didn’t think that she was going to prove herself good at running a newspaper, and — more to the point — I didn’t think that her boss, Jared Kushner, would stick by her.

In point of fact, Spiers has not been all that great at running a newspaper. Over the past year, I can barely remember a single time I’ve even so much as seen a physical copy of the Observer; I certainly haven’t read one, and neither has anybody I know. And on the rare occasions that I’ve read an Observer story online, it’s seemed under-edited and rather lightweight, for a newspaper which fancies itself the house organ of the elite.

But the point of hiring Spiers was never to get a great newspaper editor, some kind of heir to Peter Kaplan who would burnish its reputation as the paper slowly dwindled in relevance and lost a few million dollars a year. Instead, making a virtue of necessity, Kushner decided to go as webby as he possibly could, with the newspaper quite explicitly in the position of an afterthought — the legacy brand upon which the new business was going to be built.

And Spiers — to her credit — has absolutely executed on that strategy. The Observer is now, first and foremost, Observer.com. (It’s a hugely valuable domain name, which, by some freakish accident of history, wound up getting snaffled by a dilettantish New York weekly before it could be claimed by the venerable newspaper in England.) There’s a slew of verticals, running the gamut of New York interests — Wall Street, media, art, real estate — as well as a bold attempt to break into the tech blogosphere with BetaBeat. Page design is sophisticated and effective, with all sites linking generously to all other sites, with the emphasis on dynamic headlines rather than bland navbars.

The Observer’s inimitable voice is gone, replaced by a barrage of bloggish posts by a group of writers so young that many of them can’t even remember a time before Gawker. (Which was birthed, by Spiers, in 2003.) The old Observer was edited, on a story-by-story basis, in a way that the new online Observer isn’t — Spiers doesn’t have either the time or the money to have a layer of experienced journalists reworking her bloggers’ prose before it’s published.

And so, in the proud tradition of good blogs everywhere, readers are left with a highly variable product. The great is rare; the dull quite common. But — and this is the genius of the online format — that doesn’t matter, not any more, and certainly not half as much as it used to. When you’re working online, more is more. If you have the cojones to throw up everything, more or less regardless of quality, you’ll be rewarded for it — even the bad posts get some traffic, and it’s impossible ex ante. to know which posts are going to end up getting massive pageviews. The less you worry about quality control at the low end, the more opportunities you get to print stories which will be shared or searched for or just hit some kind of nerve.

Add in a few linkbait listicles, and you’ve got a recipe for a successful website — which can only be helped by its association with an honest-to-goodness print newspaper which, still, has extremely good name recognition with most New Yorkers and which we generally think fondly of. There are even nods to the old Observer’s buttoned-down worldview, here and there, if you look hard enough. For instance, there’s the way in which striking photos and videos are largely notable by their absence. The Verge this is emphatically not; while gorgeous design has its place in the Observer media empire, for the time being it seems to be confined largely to glossy magazines. Even hyperlinks are generally confined to web-first content: when stories from the physical paper appear online, they rarely have any at all.

Spiers’s Observer is not the one that her predecessor Tom McGeveran dreamed of when she was hired — one which serves to remind the rich of themselves, on which manages “to speak the patois that is being developed at Le Cirque at the table with Michael Bloomberg”. That kind of thing would always be too precious, too nichey, to work in a medium where the table stakes, in terms of reach and scale, are rising very quickly indeed. Instead, the new Observer is carving out new audiences, is aggressively embracing social media, and has much more attitude in common with HuffPo than it does with, say, the New York Review of Books. That’s something that Spiers is good at, and it’s something Kushner is happy to encourage.

I’m happy that I was wrong about the NYT paywall, and I’m happy too that I was wrong about the Observer. My mistake in both cases was to be too conservative: to think that change was probably going to be a bad thing, even in the context of a broader media world where change is the only possible alternative to death.

Both the NYT and the Observer threw out the old and did something brave and new; there are many people, in both cases, who preferred things the way they were. Myself included, truth be told. But it’s profoundly fallacious to believe that what you want is what should be, in some kind of normative sense. Spiers has come up with a formula which works, in practice, significantly better than its immediate predecessors. In the world of professional journalism, that’s something to celebrate. So, if she wants to join me and John Carney for our forthcoming lunch, she’s more than welcome. It’s on me.

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Felix Salmon is an Audit contributor. He's also the finance blogger for Reuters; this post can also be found at Reuters.com.