The Telecommunications Act of 1996, among other legislation, relaxed media ownership restrictions, allowing a single owner to possess or control an unprecedented number of radio stations per market and nationwide.

Weening had successful experience as a start-up CEO in book and magazine publishing, online services and enterprise software systems.

Weening assumed the role of Executive chairman focusing on acquisitions deal structuring, corporate finance, and internet from the company's original headquarters in Milwaukee, Wisconsin.

Dickey brought in highly regarded radio operator William Bungeroth to serve as President of Cumulus Broadcasting from new offices in Chicago's Hancock Center.

Having a reputation as an advertising sales leader, Bungeroth oversaw market-level tactical execution, including the integration of newly acquired stations into market operating units.

With this financial backing secured, Dickey and Weening began acquiring radio stations yet managed to stay "under the radar", not attracting much notice or competition.

The Cumulus strategy, as articulated in public filings, was to acquire multiple stations in a city or market, consolidate them physically to share a common infrastructure to reduce operating expenses but enrich programming.

By offering a range of audiences like newspapers, Cumulus could gain a greater share of the local advertising dollar than the individual stations could garner separately.

On January 14 respected Wall Street analyst Frank Bodenchak advised institutional clients that Cumulus may miss his estimates for Q4 1999 and the year.

PricewaterhouseCoopers, the company's auditors resigned in April citing material weaknesses in the Cumulus' financial controls[11] arising from the possible revenue restatements.

During this same period Weening got into a dispute with the SEC over his proposal to reverse some of his and Dickey's 1999 compensation to help offset the earnings miss.

The restatement as it turns out had no material impact on the financials but in the context of the dot-com bust hysteria rumours of accounting irregularities drove a significant decrease in share price which threatened the company's ability to finance pending acquisitions.

[12] Weening who had started a Silicon Valley e-commerce software company in the early 1990s had conceived and was overseeing development of the employment platform.

Dickey, whose family had just sold an Atlanta station for a reported $250 million, offered to invest in Cumulus if needed to close pending acquisitions.

This is consistent with reports in a radio industry newsletter[14] which reported that it was a widely held belief in the Radio industry was that the Dickey brothers orchestrated events that lead to the board's decision not to back the Internet project, placing Dickey at the helm of Cumulus, moving the Cumulus headquarters from Milwaukee to Atlanta and to Weening's ultimate resignation as an employee and director in January 2001.

[19] In June 2016, Cumulus Media announced the resignation of its executive vice president, treasurer and chief financial officer, Joseph P. Hannan, to "pursue other interests" after six years with the company, to be replaced by John F.

[20] It had previously been reported in April 2016 that Cumulus was "going to great lengths to keep two of its executives on board"[21] and that Hannan had been offered "a big bonus to stay" as incentive to remain with the company.

[22] In October 2016, it was announced Hannan had taken the role of chief financial officer at programmatic advertising company, Social Reality, Inc. [NASDAQ: SRAX].

[24] Noble Financial Analyst Michael Kupinski was reported to say that the resignation of CFO JP Hannan for John Abbot was "not a good sign" for the company and as a result of the change, a restructuring was likely.

Dickey garnered some strong partners in the form of Bain Capital and Crestview partners who helped finance a series of ambitious acquisitions and partnerships which were creative, made Cumulus a significantly larger company but these acquisitions and Cumulus itself have struggled in the face of slow to no radio ad growth.

[34] On January 31, 2011, Cumulus announced a deal to acquire the remaining ownership of CMP from its equity partners in a stock transaction valued at approximately $740 million that is closed in August 2011.

[36] In July 2010, Cumulus publicly announced formation of a similar venture with Crestview Partners to acquire up to $1 billion of additional radio assets.

[68] On May 9, 2023, former News/Talk 98.9 WKIM Memphis morning show co-host Bob Boccia, who has Crohn's disease, sued Cumulus Media after failing to accommodate his medical condition and religious beliefs.

On December 1, 2023, former 107.5 The Game in South Carolina sports talk radio host Tim Hill filed a civil rights lawsuit against Cumulus for firing him back in 2021 over their vaccine mandate.

Hill is claiming a violation of Title VII of the Civil Rights Act of 1964, making him the second former Cumulus host to sue the company over this vaccine mandate.

[74] Chief Human Resources Officer Todd McCarty would have also been on the witness list because he is the one who denied Hill’s request for a religious accommodation.

[75] On February 15, 2023, Cumulus Media paid "$1 million to settle a lawsuit filed by seven former employees who said the fee practices and investment selections of the company's 401(k) plan violated ERISA.

[77][78] In September 2023, the case was resolved after US District Judge Karen Gren Scholer ruled that Susquehanna had failed to meet the "burden of persuasion" to have a TRO granted and the podcast was allowed to resume production.

[77] On December 30, 2008, Cumulus Media was issued a $14,000 Notice of Apparent Liability by the Federal Communications Commission related to the stations in the Macon, Georgia, cluster.

According to the FCC, Cumulus failed to comply with record-keeping requirements and its Equal Employment Opportunity rules regarding information on recruitment sources.