Michael started his career as a strategy consultant at Gemini Consulting's Converging Markets Laboratory in
Cambridge,
Massachusetts. After law school, Michael served as an Associate in the Communications, Media and Entertainment Investment Banking Group at
Goldman Sachs in New York. He also worked on merger and hostile takeover advisory projects and equity and bank debt financing. He left Goldman Sachs in 1999. Michael was an executive at internet-telephony startup
Tellme Networks for nine years, from June 1999 until 2008. Tellme was a forerunner of
speech recognition technology. The company was sold to
Microsoft for approximately $800 million in 2007. during the first year of the Obama administration, where he served as a Special Assistant to U.S. Defense Secretary
Robert Gates from 2009 until 2011. Michael has stated that he spent time on assignment in
Afghanistan,
Pakistan, and other destinations. After his tenure at the
Pentagon, Michael acted as a consultant to technology companies in New York. He held the COO title until September 2013 when he left to join
Uber. Michael joined Uber as senior vice president of business in September 2013. He acted as CEO
Travis Kalanick's right-hand man and helped the company raise nearly $15 billion. Michael was a key player in the development of Uber's ride-sharing efforts in
China, taking an investment of $2 billion to a value of $7 billion in 2016. He also worked on creating partnerships with
Baidu and other Chinese companies. In August 2016, Michael led the merger of Uber's China operations with that of the local competitor
Didi Chuxing. In June 2021, Didi raised $4.4 billion in its IPO.
Journalism controversy On November 17, 2014,
BuzzFeed editor-in-chief
Ben Smith reported that Michael, then a senior executive at Uber, had "outlined the notion of spending 'a million dollars'" to hire four top opposition researchers and four journalists to look into "personal lives, your families" of journalists who covered Uber and its executives. Michael, who said he believed his conversation was "off the record," later claimed merely to have asked why journalists can write what he thought were false stories and attack pieces about business people. He targeted
Sarah Lacy, a journalist who worked for
Pando Daily, who had reported on Uber's
misogynist practices and culture. Uber CEO
Travis Kalanick later made a series of apologetic tweets, claiming that Michael's comments did not represent the company's views. The controversy made national news and stirred criticism of Uber. Michael later apologized for his words.
Karaoke bar controversy In 2014, several local Uber employees in Seoul, South Korea, invited Michael to join them at a "
hostess escort-karaoke bar" during a business trip. Four men in the group picked hostesses out of a lineup, and then went to the bar to sing
karaoke. One of the female Uber managers in the group felt uncomfortable during this encounter and reported the event to HR at Uber about one year later. The story came out in March 2017 when Michael contacted Gabi Holzwarth, who had been in the group at the bar, to warn her about an upcoming article in the press and, Holzwarth said, to ask her to keep the visit quiet. Michael later expressed remorse and apologized for "attending and failing to prevent" the visit to the bar. in which Uber owned 36.6 percent of a joint ride-sharing entity in Russia. Uber invested $225 million, and Yandex invested $100 million.
Trump administration In August 2019, it was revealed that Michael was considered for the job of
Secretary of Transportation as President
Donald Trump was forming his first government in early 2016.
Elaine Chao was appointed instead. In 2020, Michael, as chairman and CEO of DPCM Capital, planned to file for an initial public offering of $250 million for a blank-check company. In December 2024, President-elect Donald Trump announced his intention to nominate Michael as
Undersecretary of Defense for Research and Engineering. The Senate confirmed Michael's nomination in May 2025. In August 2025, Michael became the Acting Director of the
Defense Innovation Unit. Michael was a key figure in the
blacklisting of the AI company
Anthropic after it refused to allow the agency to use its programs for
mass surveillance and
autonomous weapons. ==Non-profit board memberships==