[13] In 2000, software maker Intuit Inc. purchased Rock Financial and renamed the national web operation Quicken Loans.

[18] In August 2020, Quicken Loans went public under the name Rocket Companies and made its debut on the New York Stock Exchange under the ticker symbol "RKT".

He has also been involved in efforts to bring major sporting events to Cleveland, including the NBA All-Star Game and the NFL Draft.

Additionally, Gilbert has faced criticism for his treatment of former head coach David Blatt and for his aggressive pursuit of tax incentives and public funding for his various business ventures in Cleveland.

[23] The partnership invests in growing businesses in the financial services, Internet technology, consumer-direct marketing, and the sports and entertainment industries.

[32] Gilbert is also invested and involved in the operation of several consumer-based technology-centered businesses, including Fathead, Veritix, Xenith, StyleCaster and Quizzle.

[33] Gilbert launched nonprofit Bizdom in 2007, which promotes both tech and brick-and-mortar entrepreneurship in Detroit and Cleveland by supporting on-the-ground service providers.

[34] In November 2009, Gilbert and a group of partners successfully backed a statewide referendum to bring casino gaming to Ohio's four largest cities.

[33] In 2013, Rock Ventures, the umbrella entity for Gilbert's investments and real estate holdings, announced it had formed Athens Acquisition LLC, an affiliate of Rock Gaming, and acquired the majority interest in Greektown Superholdings Inc., owner of the Greektown Casino-Hotel located in downtown Detroit.

[36] In November 2017, former professional Call of Duty player and 100 Thieves CEO Matthew "Nadeshot" Haag announced that Gilbert had made a multimillion-dollar investment into the esports organization.

[49] His work on the blight removal task force led him to make a $500 million investment to assist low income residents and local organizations in Detroit.

[54] Gilbert’s Hudson’s Detroit, a 1.5 million square foot project slated to open in 2025, includes an office building, which will be the headquarters of General Motors, a 681-foot skyscraper, as well as a hotel, retails stores, restaurants, and luxury apartments.

In October of that year, Gilbert also donated $15 million toward the planned $50-million Breslin Center renovation project at Michigan State University.

[62] His wife is on the Gilbert Family Neurofibromatosis Institute at Children's National Medical Center in Washington, D.C., and on the boards of ORT America and the Israeli and Overseas Committee of the Jewish Federation of Metropolitan Detroit.