When Nancy Pelosi announced in November 2025 that she would not seek re-election, it marked the close of a remarkable era in American politics and finance. The former Speaker of the House, first elected in 1987 and the first woman to ever hold the gavel, is stepping down after nearly four decades in Congress. Her retirement, set for January 2026, has sent ripples not only through the halls of Washington but also across Wall Street and Silicon Valley, where her influence has been felt in surprising ways—most notably, through the meteoric rise of an app called Autopilot.
Autopilot, founded by Chris Josephs in 2020, started as a gimmick among friends: a way to get notifications about each other's stock trades. But as Josephs began tracking the stock moves of notable figures—including, most famously, Nancy Pelosi—he stumbled upon a phenomenon that would change his life and the investing habits of millions. According to the New York Post, Josephs said, "I didn't realize how good she [Pelosi] actually was and how big of a problem this actually was," referring to the uncanny timing of Pelosi's trades. The app, which now boasts $1 billion under management and three million downloads, lets users automatically copy or follow the trades of influential investors and members of Congress.
Pelosi’s trading record became legendary among retail investors. She bought Tesla stock just before a 2021 infrastructure bill with electric vehicle credits was proposed, invested in Nvidia ahead of the CHIPs Act that funneled billions to chipmakers, and sold Google shares before the Department of Justice launched a major antitrust case. As Josephs put it, since launching the tracker, it’s been a “whirlwind” and Pelosi’s just “had banger after banger” with her stock picks. Her portfolio consistently outperformed even top hedge fund managers, leaving many to wonder: how did she do it?
Pelosi, for her part, has denied any direct involvement in trading. Her spokesperson, Ian Krager, stated, “Speaker Pelosi does not own any stocks, and she has no prior knowledge or subsequent involvement in any transactions.” Still, the timing and success of the trades—often executed by her husband, Paul Pelosi—captured the public’s imagination and sparked ongoing debates about the ethics and transparency of congressional stock trading.
With Pelosi’s retirement, Autopilot is preparing for a major shift. The app will stop tracking her trades at the end of her term, rolling over the roughly $500 million that users invested following her moves into a new “general insider trading” portfolio. This new fund will track trades by other prominent politicians, such as Rep. Dan Crenshaw (R-Texas) and Rep. Marjorie Taylor Greene (R-Ga.), according to NYNext. Josephs, reflecting on the transition, remarked, “It’s kind of the end of an era … you’re losing the queen. It’s turning the chapter on the political stock trading movement.”
Autopilot is not resting on its laurels. The company recently raised $8 million to expand its physical presence from San Francisco to New York City, and is hiring top talent—including a former trader from Ken Griffin’s Citadel. Josephs sees the company’s mission as bringing transparency to the often opaque world of institutional investing. “Our mission is the same… it’s to find the best investors and showcase them all in an effort to bring more transparency to the broader institutions,” he told NYNext.
Transparency, or the lack thereof, has been a recurring theme in the debate over congressional stock trading. Currently, lawmakers are required to file disclosures within 45 days of making a trade, and only need to provide a price range rather than exact figures. Josephs is an advocate for reform, saying, “Just get rid of the delay, make it transparent, make it open, and then allow people to just watch.”
Pelosi’s retirement has prompted an outpouring of admiration from colleagues, especially within the Asian American and Pacific Islander (AAPI) community. Rep. Grace Meng (D-N.Y.), chair of the Congressional Asian Pacific American Caucus, hailed Pelosi as a “trailblazer, a champion for working families, and one of the fiercest advocates for Asian Americans, Native Hawaiians, and Pacific Islanders in Washington, D.C.” Meng credited Pelosi’s leadership for the passage of key legislation, including the COVID-19 Hate Crimes Act and the creation of the National Museum of Asian Pacific American History and Culture.
Rep. Mark Takano (D-Riverside) called Pelosi “the greatest legislative leader of the 21st century,” praising her for championing LGBTQ+ rights, veterans, and California’s diverse communities. “Our community has had no greater ally as Speaker, and her leadership has brought real, lasting change for LGBTQI+ people across the country,” Takano said. He also highlighted Pelosi’s role in passing landmark bills such as the Don’t Ask, Don’t Tell Repeal Act, the Matthew Shepard and James Byrd, Jr. Hate Crimes Prevention Act, and the Respect for Marriage Act.
Other prominent voices, including Rep. Doris Matsui (D-Sacramento) and Sen. Mazie Hirono (D-Hawaii), echoed these sentiments, describing Pelosi as “the most consequential and effective Speaker in American history” and a leader who “never lost sight of her mission – to make life better for the children and for the people.” Pelosi’s legacy, they agreed, is not just in the laws she helped pass, but in the values she championed and the people she inspired.
Of course, Pelosi’s tenure was not without controversy. She was a frequent adversary of former President Donald Trump, and in her first interview after announcing her retirement, she addressed her now-famous comment calling Trump a “vile creature” and “the worst thing on the face of the Earth.” Speaking to CNN’s Anderson Cooper, Pelosi clarified, “By the way, I said that as a euphemism. I could have done much worse.” She explained her criticism stemmed from Trump’s disregard for the Constitution and his actions as president, which she believed undermined democratic institutions. Yet, when pressed, Pelosi preferred to focus on the future of House Democrats rather than rehashing old battles.
As Pelosi prepares to leave Congress, speculation swirls about her next chapter. Josephs, ever the entrepreneur, joked, “If anyone has any connection to her, we would love to hire her.” Whether or not Pelosi takes up a new role in finance, her impact on both politics and the markets is undeniable.
With the political stock trading movement entering a new phase and Pelosi’s legacy firmly established, both Capitol Hill and Wall Street are bracing for what comes next. And as Autopilot and its millions of users look for the next big name to follow, one thing is clear: Nancy Pelosi’s shadow will loom large for years to come.
