Casey Flanagan

What To Bet On

Two years ago, Grantland.com – a site that covers sports and pop culture – was launched. At the time, the site received a good bit of coverage – especially for a website launch. One article from The Atlantic’s title said it all – “Bill Simmons’s Grantland Is Doomed Even Before Launch.” Last week, Grantland celebrated its two year anniversary.

I’m not surprised. Its early detractors believed it would fail for many of the reasons I thought it would succeed – the identifiable personality of the site’s founder and the high-price of the site’s talent, to name just two.

Sure, hindsight is 20/20. It’s easy to pick the winner two years later. But Grantland’s success stems from two core strengths that were evident from the outset:

Fans who care

Bill Simmons – the site’s founder – was probably the most widely read sportswriter in the America. The site’s consulting editors – Malcolm Gladwell, Dave Eggers and Chuck Klosterman – all had rabid, rabid fans. As content begins to look and feel more and more similar and as eyeballs are splintering in more and more directions, why wouldn’t you bet on a core of writers who already have loyal readers?

And why are these readers loyal?

Quality content

That’s the most important thing. Always has been. Always will be. Grantland tells stories. They write in long-form. They experiment with formats. They do things differently. They are focused on not just having a point, but having a point-of-view. And while they don’t take themselves too seriously, there is clearly a pride in craftsmanship. You get the feeling that the product they put out is not just one they stand behind, it’s one they’d read themselves.

We have many choices for where to invest our time, our money, our resources. “Stories well told” and “content people look forward to” are opportunities I would bet on. Every single time.

Interested in more stuff I find interesting? Follow me @casey_flanagan on Twitter.

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