[4] In September 2021, Watson attracted public controversy in the wake of a New York Times article by Ben Smith alleging that Ozy had made significant misrepresentations to investors.

[13] After two years at McKinsey, Watson left to co-found Achieva College Prep Service based in San Mateo, California.

[13] Watson sold Achieva in 2002 to competitor Kaplan, Inc.[13][16] He later worked as the Global Head of Education Investment Banking for Goldman Sachs.

[20] In October 2004, Watson gave an exclusive interview with 2004 Democratic National Convention keynote speaker, then-Illinois U.S. Senate candidate and future U.S. President Barack Obama.

[34] In the wake of allegations that he committed fraud in his role as CEO of Ozy Media, Watson resigned from the NPR board on October 1.

[35] In September 2013, Watson launched Ozy, a daily digital news and culture magazine,[36][37] with Samir Rao, a fellow Goldman Sachs alumnus.

As CEO, Watson led Ozy to raise over $70 million in fundraising from investors including Laurene Powell Jobs, Louise Rogers, Ron Conway, and others.

In late September 2021, Ozy Media was the subject of a New York Times article[41] bringing attention to possibly fraudulent business practices and misrepresentations, including some attributed to Watson.

[42] Five former Ozy employees reported that, as a New York article summarized, "Watson's demands, expectations, and plans were often detached from reality, yet were enforced with an intensity that some felt bordered on cruelty.

[44] Watson told NBC News's Today that he had referred to the Osbournes as investors because they received shares of Ozy stock as part of a legal settlement.

[8] The arrest occurred shortly after Samir Rao, the co-founder and ex-chief operating officer of Ozy Media, pled guilty to fraud charges.

Pichai clarified that while Google considered hiring Watson and potentially investing $25 million in Ozy to facilitate the transition, no acquisition discussions or nine-figure offers were made.

[55][56] In December 2024, the United States District Judge Eric R. Komitee imposed a 116-month sentence for fraud and aggravated identity theft, finding Watson guilty after an eight-week trial.

Prosecutors revealed that Watson, a former Goldman Sachs banker and MSNBC host, masterminded a scheme that caused "tens of millions of dollars" in investor losses.

The company's downfall began in 2021 when a New York Times investigation exposed an executive impersonating a YouTube representative during a Goldman Sachs call.

Watson claimed this was due to his deputy's mental health issues, but court documents suggested he was directly involved in guiding the deception.