Bill Simmons is probably the most popular sportswriter in America and now he’s a media mogul earning between $7 and $9 million per year. He oversees approximately 100 employees, with a weekly TV show that will begin airing June 22 on HBO and a media network anchored by the multimedia endeavor The Ringer.

Simmons achieved this with intelligence, lots of hard work and content marketing (not to mention a drama-filled split with his former employer ESPN earlier this year).

He has recorded hundreds of podcasts in his nine years with the medium. They’re often maddingly bro-ish; it’s as if you’re overhearing an excuse for two friends to engage in a rambling, pot-induced conversation. That’s part of the charm, too; it feels natural and is clearly something Simmons loves doing.

He moves seamlessly between diverse subjects and guests.

It was the juxtaposition of two podcast guests on shows published within a few days of each other earlier this year — one featuring NBA power forward Serge Ibaka, the other with hipster millennial “goddess” Lena Dunham — that caught the attention of HBO brass and eventually opened the door to his sweet new gig. In addition to an annual salary that scrapes seven figures, Simmons has HBO as a minority investor in his media company, Bill Simmons Media Group, which runs The Ringer.

His content play worked on me, too.

When his 736-page “The Book of Basketball” came out in 2009, Simmons appealed to podcast listeners to buy the book by asking for support with something along the lines of, “I’ve been doing this podcast for free for two years and I’ve never charged or asked for anything. Buy the book.” I bought the book.

Simmons’ example shows that producing content you’re passionate about can lead to huge opportunities. Countless ways exist for real estate firms and agents (and all of us!) to amplify their brands with similar efforts.

Image credit: David Shankbone