Bill Simmons on pivoting to video, paid subscriptions and that time he almost gave up on journalism

August 23, 2017
Category: Business & Work

Bill Simmons may be one of the biggest names in sports journalism, but he didn’t start that way. Before he joined ESPN, before he was fired, before he founded his own site, he was a blogger for AOL Digital Cities Boston grinding out posts for $50 per week.

“I would’ve done anything to get read by anyone,” Simmons recounted in a recent edition of his eponymous podcast. “And I think they paid me $50 per week for the first three months. And I just busted my ass and eventually, I got to $200 a week.”

Simmons, who built a career on his own (nearly) unpaid labor, weighed in on the recent controversy over underpaid SB Nation bloggers, the value of digital advertising and the time he almost gave up on journalism this week with Ringer Editor-at-Large Bryan Curtis and Wall Street Journal reporter Jason Gay. Here are the most interesting snippets, via Soundcloud:

On working for free

From my own standpoint, in 1997, I’d been out of the newspaper business for almost a year, and there’s this Digital City Boston site that has a movie guy, I’m trying to be their sports guy. I would’ve done anything to get read by anyone. And I think they paid me $50 per week for the first three months. And I just busted my ass and eventually I got to $200 a week. And I was still bartending on the side for a year-plus. And I can’t remember when I got to the point when they were paying me $550 or $600 a week. But it was probably about 15-18 months in — no benefits.

And I did that site for four years, just trying to get seen. And it sucks. And it becomes discouraging after awhile. But on the other hand, there’s no other way I could have created a break. So I look at somebody like — y’know, look at Kevin O’Connor, one of our young basketball writers. He was writing for CelticsBlog when we saw him. And I don’t know what he was making for them. He was probably making a little, but not a lot. …But we never would have seen him if he wasn’t on that site. So it’s a Catch-22, where you can’t get seen unless you’re writing — and it can be SB Nation, it can be Fansided…it can be Deadspin, it can be wherever. But you have to get seen somehow. Nobody’s going to say, ‘You’re hired.’

On almost quitting journalism

Some of this has to come down to, ‘how long do you do something before you give up?’ …There were two different points when I almost gave up. 1996, after I left The Herald. And then in 2000, year three of my site. My site was good. I had an audience, but I couldn’t break through, I couldn’t get over the hump. And I remember going out to dinner near the end of that summer with my future wife and my mom and my stepdad. And I was like, ‘I think I’m going to give up. I think I’m going to go into commercial real estate. And I think a lot of writers have hit that point, where you just go: ‘Is this worth it? Is this going to happen?’

…I’m sure there are people who’ve given up who shouldn’t have.

On digital advertising

I think part of the problem right now though is that the old Internet model with advertising on websites wasn’t a good model. And I think it took most companies a long time to realize that. And once they realized that, the model shifted on people making content. And they were like, ‘Oh, no! It was great before!’ Before, it wasn’t a great model.

…The stuff always moves in trends that are almost too severe. Everyone’s saying, ‘Video, video, video!’ It’s like, ‘Well there are a lot of ways you can integrate sponsors.’ There’s branded content and there’s podcasts. There’s video ads at the beginning and end of stuff. …You can get more creative. I think the old way of ‘here’s a banner for your peter king column — that model is going away, and it’s not coming back.

On paid content

The model that is really good and is the model that I think is going to succeed long-term is the model where, ‘here’s some of our stuff, and you can read 10 of our pieces, or 12. But if you want the whole shebang, here’s the subscription thing.’ That model’s working.