Deposition reveals AI‑generated email at the heart of a wrongful‑termination fight
In an April 10, 2026 deposition, former Run The World tech cofounder Xuan Jiang (formerly a Facebook engineer) testified that she used ChatGPT to draft an email intended solely to reject a buyout offer. The AI‑generated message, dated April 3, 2023, opened with the line “I have made the difficult decision to step down as the tech cofounder of Run the World,” language that Run The World now presents as proof of a resignation.
"You had ChatGPT write this; right?" an attorney asked Jiang during the deposition. "Correct," she answered.
Jiang explained that the prompt she gave the model was meant to convey three points: (1) she was refusing the proposed exit package; (2) she understood the rejection would lead the company toward a wind‑down; and (3) she wanted to preserve good relations with a16z partners Connie Chan and Peter Blackwood for a future AI‑focused venture. She recalled asking ChatGPT to say she was “sorry that I’m not accepting the offer” and to express sadness about the anticipated shutdown while noting her interest in AI‑powered virtual hosts and NPCs.
The resulting email, however, framed the situation as a personal departure. It stated:
- “I have made the difficult decision to step down as the tech co‑founder of Run the World.”
- Jiang would pursue “AI‑powered virtual hosts and NPCs.”
- The company would continue “without my continued involvement” under “new leadership.”
- She offered to support the new leadership from the outside.
When pressed about the phrase “new leadership,” Jiang told the court, “I don’t know what ChatGPT does.”
How the company reads the AI‑written note
Run The World has filed a summary‑judgment motion in the San Francisco Superior Court (case CGC‑24‑618394) arguing that the email objectively constitutes a resignation. The company points to language indicating Jiang was “moving on,” that she anticipated the firm operating without her, and that she offered to aid “new leadership.” The email’s address book lists a16z partners, reinforcing the company’s view that the communication was directed to the primary investor and therefore carries the weight of an official departure.
Jiang’s counter‑narrative
Jiang maintains that the term “step down” referred only to the expected end of her founder role in a wind‑down, not to a resignation from her employee, CTO, or board positions. She testified that she intended to stay on as an employee and director until the company’s liquidation, a stance supported by a separate email she sent to the firm on April 12, 2026. In that email, Wilson Sonsini attorney Allison Ivey Toth, on behalf of Run The World, wrote “I am writing on behalf of Run the World, Inc. to confirm your resignation effective today.” Jiang immediately replied that the company had made a mistake and that she had never resigned; the response email is not part of the public record.
The buyout offer that sparked the dispute
During the deposition Jiang read the terms of the buyout proposal that she repeatedly rejected:
- 3,833,333 vested shares purchased for $344,999.97 (based on a Carta 409A valuation of $0.09 per share)
- Twelve months of COBRA coverage valued at $4,917.84
- $30,000 cash for resigning and signing a release
The total comes to $379,917.81, which Jiang described as “approximately $380,000.” The offer, she said, was “not a satisfying offer and I’m not accepting that.”
Pregnancy, leave, and alleged retaliation
Jiang disclosed her pregnancy to cofounder and CEO Xiaoyin Qu during a February 6, 2023 video call. That same conversation covered plans to close Run The World or pivot its remaining resources into AI, a move that would require buying Jiang’s shares. After the disclosure, Jiang experienced typical pregnancy symptoms and emailed Qu on March 6 requesting medical leave. Qu responded sympathetically and said he would consult the investors.
Jiang alleges that, following her request, her administrative access to Notion, Gusto, Google Workspace, Brex, and the company bank account was reduced or removed. She also alleges repeated messages to her and her husband during medical leave, pressure to decide on the buyout by March 15, warnings that a shutdown could end her health insurance, and a transfer of company funds from First Republic Bank to an account she could not access. Run The World counters that these contacts were part of urgent banking, payroll, shareholder, and wind‑down matters, noting that the March 2023 regional banking crisis caused operational disruptions.
The company’s broader trajectory
Qu and Jiang founded Run The World in 2019, leveraging their experience as Facebook engineers to build a virtual‑events platform that surged during the pandemic. The startup raised more than $15 million, reportedly achieving a $60 million valuation. By late 2022, the workforce had contracted to the two cofounders and a remote salesperson or contractor, with monthly revenue around $10,000 (as of Jiang’s 2021 check). Approximately $7 million remained in the company’s bank account during the disputed period, according to Jiang’s testimony (Axios later cited a similar figure of $8 million).
Run The World later sold most operating assets to EventMobi while retaining its cash. The company sued Jiang in June 2023, accusing her of disrupting domains and systems after her departure and alleging an outage affecting roughly 700,000 accounts. Jiang counter‑claimed discrimination based on pregnancy, wrongful termination, shareholder rights violations, and alleged misconduct by a16z. A federal judge dismissed the computer‑access claim and sent the remaining state claims back to state court. Jiang filed the current state‑court action in September 2024.
Current litigation posture
Run The World filed its summary‑judgment motion on April 24, 2026, seeking judgment on two claims: (1) pregnancy‑based workplace harassment and (2) wrongful termination in violation of public policy. The company argues that the email proves resignation, that the buyout was a shareholder transaction, and that Jiang’s own email establishes she quit. Jiang argues the email does not constitute a resignation and that she never intended to leave her employment role.
The court has not yet ruled on the disputed facts. A hearing is scheduled for September 11, 2026, with a trial set for November 16, 2026. The motion includes separate filings by Qu, Connie Chan, and a16z, though the current filing focuses on Run The World’s arguments.
Why the AI angle matters
The case highlights how generative AI tools can become unintended legal evidence. An AI‑drafted resignation‑type email is now central to a multi‑million‑dollar dispute over buyout terms, pregnancy discrimination, and the fate of a pandemic‑born startup. The outcome may shape how founders, counsel, and investors draft and vet AI‑generated communications in high‑stakes corporate contexts.