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SmartLess / – “Bill Simmons”

SmartLess – “Bill Simmons”

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In this episode of the “SmartLess” podcast, the hosts Jason Bateman, Sean Hayes, and Will Arnett are joined by guest Bill Simmons. They engage in a lively and humorous conversation, covering a wide range of topics including sports, journalism, podcasting, and more.

Main Takeaways

Bill Simmons’ Multi-Talented Career

  • Bill Simmons is a jack of all trades and a master of all, with books, columns, and TV appearances that are must-reads and must-sees.
  • He has a degree in political science and a masters in print journalism.
  • Bill was a guest on the podcast before, but the episode was never aired due to being too topical.
  • The hosts admire Bill’s success and his unapologetically honest opinions on culture.

Bill Simmons’ Love for Sports

  • Bill is a huge baseball fan and was devastated when Mookie Betts left the Red Sox for the Dodgers.
  • Red Sox got super analytical about baseball players as they hit their 30s.
  • Bill’s love for sports started as a kid and he wondered if he could get paid for it in college.
  • Bill decided to write from a fan’s perspective because he couldn’t get press passes.
  • Bill’s first moment of access to locker rooms and press boxes was in 2001 when ESPN got his column.

Bill Simmons’ Journey in Podcasting

  • Podcasting became a medium after Bill Simmons discovered it on an interview link with the Celtics GM and started his own podcast with friends to emulate Mike and the Mad Dog.
  • The early days of podcasting were rocky, with Simmons and Adam Carolla unable to record in the same room and resorting to recording on the phone in Simmons’ driveway.
  • Bill Simmons started podcasting in 2007 with no idea people were listening.
  • By 2009, he had 50 celebrity guests on his podcast.
  • Podcasting was a more fun format for celebrities to have an extended conversation without the risk of a sensational headline.

The Impact of Sports and Sports Betting

  • Sports teams can set the mood of a city and bring people together.
  • Watching incredible athletes like Tiger Woods in real time is a cool experience.
  • Online sports betting is becoming more prevalent, but there are checks and balances in place to prevent minors from gambling.
  • Sports networks are promoting and participating in the dialogue around sports betting, with ESPN partnering with Penn for ESPN Bet.
  • Sports have a long history of gambling scandals, but it would be difficult to fix any games now due to increased attention and monitoring.

Ownership in Sports and Entertainment

  • Some owners prioritize winning and profit over the impact on the industry or culture, potentially causing harm in the long run.
  • Fan bases may not have much leverage over wealthy team owners.
  • TV rights and financial value are more important to owners than fan opinion.
  • Toxic environments created by owners can harm teams and cities.
  • Success and wealth can be achieved without losing touch with one’s simpler self.


Bill Simmons: A Multi-Talented Sports Writer and Podcaster

Bill Simmons is a highly accomplished sports writer and podcaster, known for his insightful and entertaining commentary on sports and pop culture. With a degree in political science and a masters in print journalism, Simmons has established himself as a respected voice in the industry. He started his career by writing from a fan’s perspective, which resonated with readers and allowed him to gain access to locker rooms and press boxes. In the early 2000s, Simmons ventured into podcasting, which quickly became a popular medium for celebrities to have unfiltered conversations. Throughout his career, Simmons has demonstrated his versatility and willingness to adapt, leaving ESPN and HBO to create his own network. He has also been a vocal advocate for sports betting, recognizing its increasing prevalence and the potential it holds for the industry. However, he acknowledges the need for checks and balances to prevent any potential scandals. Simmons also discusses the impact of ownership in sports and entertainment, highlighting the importance of prioritizing the industry and culture over profit. Overall, Bill Simmons’ journey in sports journalism and podcasting is a testament to his passion, talent, and ability to connect with audiences.


Bill Simmons’ appearance on the “SmartLess” podcast provides listeners with a fascinating insight into his career, love for sports, and journey in podcasting. From his beginnings as a fan writer to becoming a multi-talented media personality, Simmons has made a significant impact in the world of sports journalism. His unapologetic opinions and willingness to push boundaries have garnered him a dedicated following. Whether discussing the cultural impact of sports, the challenges of ownership, or the evolving landscape of podcasting, Simmons’ expertise and engaging storytelling captivate listeners. This episode offers an entertaining and informative conversation that will leave fans eagerly anticipating Simmons’ future projects.

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