He co-founded Aspiration, Inc., an eco-friendly financial firm based in Marina del Rey, California, and was its chief executive officer from 2013 to October 2022.

He later received his Juris Doctor from the UC Berkeley School of Law with support from The Paul & Daisy Soros Fellowships for New Americans.

[6] Cherny left his position as chief executive officer in 2022 after a deal to go public as a special purpose acquisition company (SPAC) at a $2.3 billion valuation fell through.

[7][8] Under Cherny's leadership, Aspiration created cash management accounts that ensured customers' deposits were with banks that did not lend to fossil fuel companies.

[13][7] In January 2024, the U.S. Department of Justice and the Commodity Futures Trading Commission initiated a probe into whether Aspiration "misled customers about the quality of the carbon offsets it was selling".

[13] As a writer for The Harvard Crimson, Cherny wrote political pieces highlighting Bill Clinton's 1996 reelection campaign.

[22][23] He is also the author of the non-fiction books The Next Deal: The Future of Public Life in the Information Age, (2008)[24] and The Candy Bombers: The Untold Story of the Berlin Airlift and America's Finest Hour.