Bill Simmons

Bill Simmons is the podfather of sports media — the writer who blogged his way from a Boston basement to a quarter-billion-dollar empire. The arc is almost hard to believe: The Boston Sports Guy becomes ESPN’s Page 2 columnist becomes the founder of Grantland becomes the founder of The Ringer becomes Spotify’s nine-figure acquisition. Every step up looked impossible until he took it.

Start at the beginning, because the beginning explains everything. William John Simmons III, born September 25, 1969, in Marlborough, Massachusetts, came up dreaming of the classic newspaper path: political science at the College of the Holy Cross, a master’s in print journalism from Boston University, high-school sports writing for the Boston Herald. When that lane looked blocked, he did what nobody was supposed to do in 1997 — he started BostonSportsGuy.com, a raw, funny, fan-first site on AOL that pulled 10,000 readers and 45,000 page views a day by 2001. The voice was already fully formed: a fan’s brain, a writer’s mouth, pop-culture detours and all. ESPN hired him in 2001, and “The Sports Guy” became the most-read columnist in the building.

The ESPN years (2001–2015) were a run few sportswriters will ever match. The Page 2 columns. The B.S. Report, one of the medium’s first great podcasts, launching in 2007 — back when podcasting was a hobby for weirdos. A stint writing for Jimmy Kimmel Live! in 2003. The Book of Basketball: The NBA According to The Sports Guy (2009), a New York Times bestseller that treated NBA history like a bar argument and won the argument. The creation of ESPN’s 30 for 30 documentary series — arguably the most decorated sports-doc brand ever — and the founding of Grantland in June 2011, the longform sports-and-culture site where his columns and podcasts lived at their peak.

The ending at ESPN is part of the legend: suspended in 2014 after daring the network to punish him for criticizing NFL commissioner Roger Goodell, then out in 2015. Grantland was shuttered soon after. So Simmons did the only thing he knew how to do — he started another one. The Ringer debuted in February 2016, and he imported his best people: Sean Fennessey (head of content), Juliet Litman (head of production), Chris Ryan (editorial director), Mallory Rubin (head of editorial). What set it apart from Grantland immediately was the podcast engine — dozens of shows from day one, with the flagship Bill Simmons Podcast at the center, the Rewatchables movies show as its cult favorite, and everything from NBA to prestige-TV coverage in between. Edison Research ranked his show the most popular sports podcast in America in Q2 2023 — and the No. 30 podcast overall, period.

The Spotify deal in February 2020 — reported at around $200 million, with some outlets saying as much as $250 million — was the moment podcasting became big business, and Simmons was the proof of concept. The show crossed its 1,000th episode in June 2022. The formula never changed: a fan’s brain, a writer’s mouth, and guests ranging from athletes to directors to fellow obsessives.

The Ringer’s video operation extends the same sensibility to film: Ringer Movies breakdowns — the Halloween II episode with Chris Ryan and Van Lathan is the template — smart people, strong opinions, zero pretension. The documentary wing keeps scoring too: the Mr. McMahon Netflix series on WWE’s Vince McMahon carries his producer credit, and the 30 for 30 legacy — Sports Emmy-winning, industry-defining — remains his signature achievement behind the camera.

It hasn’t all been applause. The Goodell wars, the Grantland shutdown, and the 2020 flap over The Ringer’s lack of diversity — when Simmons said “It’s a business. This isn’t Open Mic Night,” critics called it tone-deaf — are part of the record. But the through-line of the career is undeniable: he invented the conversational sports take — the “what if” hypotheticals, the pop-culture detours, the willingness to be wrong loudly — and an entire generation of imitators is still working in his shadow. The Ringer itself is the legacy play: a full media company built in his image — podcasts, video, writing — that became the template for every creator-led sports network after it. Simmons didn’t just ride the podcast wave; he helped create the ocean.

Nineteen years into podcasting, he’s still the medium’s center of gravity — and the business case every creator-led network now cites. The arc from a one-man AOL blog to a Spotify-owned media company is the blueprint the whole industry followed: build the audience on personality, diversify into podcasts and video, then sell the machine, not just the voice. Whatever the next chapter is — new platforms, new formats, the same Boston fan arguing about the Celtics — it will be argued loudly, recorded weekly, and listened to by millions who learned the vocabulary from him.

Why people listen: because he’s the fan who made it. Every Simmons take carries the DNA of the kid arguing about the Celtics in a bar — just with better guests, better production, and two decades of being right often enough to matter.