After leaving Goldman Sachs, he founded Gordian Group, LLC in 1988, a boutique investment bank in New York specializing in solving complex problems in bankruptcy and restructuring.

In 2007, Henry Owsley, Peter S. Kaufman, and Sam Bronfman co-founded Bacchus Capital Management, a private equity fund that invests in wineries.

[10] In 2015, Owsley and his partner Peter S. Kaufman updated the volume that they co-wrote in 2005, Distressed Investment Banking: To The Abyss and Back, publishing with Beard Books both times.

"[12] In 2014, Owsley and Kaufman wrote Equity Holders Under Siege: Strategies and Tactics for Distressed Businesses, again with Beard Books, intended for all boards of directors, management teams and shareholders and owners of financially stressed situations, with advice for buyers and professionals as well.

[14] In January 2014, the industry organization M&A Advisor announced that Gordian won their "Boutique Investment Bank of the Year" award for the third time.