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==Jomboy Media==
In 2017, O'Brien created a [[podcast]] called ''Talkin' Yanks'' with his friend Jake Storiale<ref name="NYTJomboy2022"/> and produced by David Mendelsohn, which built a following and led O'Brien to raise money and turn Jomboy Media into a full-time job by the end of 2018.<ref>{{cite web|url=https://frntofficesport.com/jomboy-media-jimmy-obrien/|title=After Viral Astros and Yankees Videos, 'Jomboy' Looks To Build Media Brand
|website=frntofficesport.com|first=Michael|last=McCarthy|date=March 5, 2020|accessdate=July 30, 2020}}</ref>
|website=frntofficesport.com|first=Michael|last=McCarthy|date=March 5, 2020|accessdate=July 30, 2020}}</ref> While watching a July 2019 Yankees game, O'Brien discovered Aaron Boone's argument with umpire Brennan Miller had been picked up by microphones on an [[MLB.TV]] feed, and he published the video of the argument with subtitles showing what was being said. The video went viral and Boone's use of the phrase "savages in the box" became a motto for the Yankees.<ref name="espn81619">{{cite web |url=https://www.espn.com/mlb/story/_/id/27392799/how-fan-viral-video-turned-aaron-boone-yankees-savages |title=How a fan's viral video turned Aaron Boone's Yankees into 'savages' |last=Harvey |first=Coley |date=August 16, 2019 |website=ESPN |access-date=May 16, 2020}}</ref> O'Brien published more "breakdowns" of incidents in MLB and other sports with occasionally profane commentary and gained 300,000 YouTube subscribers after the Boone video. Yankees and MLB officials expressed mixed reactions to the viral video, with some questioning whether fans should be able to hear conversations on the field and in the dugout and others appreciating O'Brien for making creative content that could market baseball to younger fans. He also started Talkin' Baseball, a baseball podcast in July 2019 with Storiale. The podcast is produced by Mendelsohn and was joined in 2020 by former Major League Baseball player [[Trevor Plouffe]].<ref name="azpbs">{{cite web|last=Block|first=Erica|date=December 25, 2019|title=Could baseball influencers such as Jomboy, PitchingNinja offer solution to MLB's marketing woes?|url=https://cronkitenews.azpbs.org/2019/12/25/could-baseball-influencers-such-as-jomboy-pitchingninja-offer-solution-to-mlbs-marketing-woes/|access-date=May 16, 2020|website=Arizona PBS / Cronkite News}}</ref><ref name="NYTJomboy2022"/><ref name="Prognosticator">{{cite news |last1=Neale III |first1=La Velle E. |title=Prognosticator Plouffe called Series right |url=https://www.newspapers.com/clip/109643362/prognosticator-plouffe-called-series-rig/ |access-date=16 September 2022 |work=Star Tribune |date=21 November 2021 |page=C2}}</ref>▼
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In November 2019, O'Brien published a two-minute video appearing to demonstrate how the Astros were stealing signs in the 2017 season as a part of the [[Houston Astros sign stealing scandal]], within hours of the release of an article in ''[[The Athletic]]'' which detailed the allegations for the first time.<ref name="HowAthleticBroke">{{cite news |last1=Drellich |first1=Evan |title=How The Athletic broke the Houston Astros cheating scandal: Excerpt |url=https://theathletic.com/4138657/2023/01/31/houston-astros-book-excerpt/ |access-date=31 January 2023 |work=The Athletic |date=31 January 2023 |language=en}}</ref><ref name="NYTJomboy2022"/> In the video, O'Brien showed the scheme playing out in real time in a game against the [[Chicago White Sox]]. Whenever catcher [[Kevan Smith (baseball)|Kevan Smith]] called for pitcher [[Danny Farquhar]] to throw a [[changeup]], the sound of someone banging on a trash can in the Astros' dugout was clearly audible. The White Sox were forced to change their signs as a result. O'Brien argued that this sequence proved there was no way the Astros could have gotten the signs without the help of technology.<ref>{{cite web|url=https://www.foxnews.com/sports/astros-video-sign-stealing-allegations-2017|title=Video shows how Houston Astros were allegedly stealing signs during 2017 season|website=[[Fox News]]|first=Ryan|last=Gaydos|date=November 13, 2019|accessdate=January 17, 2020}}</ref> O'Brien published more videos in subsequent days, which garnered millions of views on YouTube, Twitter and other platforms.<ref name="espn11720">{{cite web |url=https://www.espn.com/mlb/story/_/id/28476354/how-internet-helped-crack-astros-sign-stealing-case |title=How the internet helped crack the Astros' sign-stealing case |last=Lee |first=Joon |date=January 17, 2020 |website=ESPN |access-date=May 16, 2020}}</ref>
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