Prompt Cast
Bill Simmons' Journey from ESPN to Building The Ringer
TLDR Bill Simmons built a $250 million media company, The Ringer, after leaving ESPN, starting with a passion for sports writing and creating engaging digital content. Despite facing challenges, he focused on podcasts for revenue, leading to a successful acquisition by Spotify and emphasizing continuous improvement for success.
Timestamped Summary
00:00
The Ringer's Bill Simmons built his own $250 million media company after a falling out with ESPN.
06:51
A late-night basketball game in the 70s sparked a lifelong passion for sports writing in Bill Simmons.
12:44
Bill Simmons started his sports writing career by critiquing his college basketball coach, which led to his realization of his talent and passion for writing.
18:31
Bill Simmons started writing a digital column about Boston sports and other topics, gaining a following through email chains and criticizing media members and sports radio negativity.
24:15
ESPN saw the opportunity in digital sports content that Sports Illustrated missed, leading to Bill Simmons' column success and eventual career breakthrough.
30:40
Bill Simmons discusses his passion for sports, his dedication to watching games, and his approach to sports writing that aimed to be unpredictable and engaging for readers.
36:22
Bill Simmons reflects on his time working on a TV show in LA, missing his column, and the impact of his writing as he transitions back to writing for ESPN.
42:30
Bill Simmons started his own podcast at ESPN, initially unsure about the format but eventually gaining momentum and attracting celebrities as guests.
48:16
Bill Simmons created Grantland as a sports and pop culture website under ESPN, aiming to provide a unique platform for up-and-coming writers and establish a digital content epicenter for the network.
54:10
Bill Simmons expressed his disappointment with ESPN's content decisions and felt that Grantland's cultural impact was undervalued within the company.
59:57
Bill Simmons faced challenges and received business offers after being suspended from ESPN, leading him to consider starting something new.
01:06:00
Bill Simmons started The Ringer with a team from Grantland, focusing on podcasts for revenue, but faced challenges with a failed HBO show and the steep learning curve of running a media company.
01:11:45
Bill Simmons realized that podcasts were the main revenue source for The Ringer, leading to the decision to focus on talent development and content creation without seeking venture capital funding.
01:17:36
Bill Simmons explains that Spotify's acquisition of The Ringer allowed them to take cash off the table, not worry about the bottom line, and potentially grow even bigger.
01:23:28
Bill Simmons reflects on his career, emphasizing the importance of continuous improvement, hard work, and dedication in achieving success.
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