50 East River Center Boulevard, Suite 180 Covington, Kentucky 41011 www.regentcomm.com ANNUAL REPORT 1999 Directors Officers Portfolio Terry S. Jacobs R. Glen Mayfield Terry S. Jacobs Chairman of the Board, Chief Principal of RiverCities Capital Chairman of the Board, Chief Executive Officer and Treasurer Fund Limited Partnership and Executive Officer and Treasurer President of Mayfield & William L. Stakelin William L. Stakelin Robinson, Inc., a management of Stations President, Chief Operating President, Chief Operating and financial consulting firm. Officer and Secretary Officer and Secretary Richard H. Patterson Joel M. Fairman Joel M. Fairman Vice President of Waller-Sutton St. Cloud, MN L Vice Chairman Vice Chairman L Watertown, NY Management Group, Inc. and a principal of Spire Capital Grand Rapids, MI L L Utica-Rome, NY Kenneth J. Hanau Fred L. Murr L Partners, L.P., a private equity Flint, MI L Albany, NY Principal of Weiss, Peck and Senior Vice President L Erie, PA Greer, L.L.C., a venture capital fund specializing in media and Anthony A. Vasconcellos L Mansfield, OH L investment firm, and a principal communications. Redding, CA Vice President and Chief of WPG Private Equity Partners, L Chico, CA William P. Sutter, Jr. Financial Officer # II, L.L.C. Covington, KY Vice President of Mesirow Matthew A. Yeoman L Victorville, CA William H. Ingram Financial Services, Inc., a finan- Vice President, Finance L Palmdale-Lancaster, CA Chairman of the Board of cial services firm, general partner Directors of Waller-Sutton of Mesirow Capital Partners VII, David J. Remund Management Group, Inc., which and Senior Managing Director Vice President of Engineering L El Paso, TX manages Waller-Sutton Media of Mesirow Private Equity Partners, L.P., an investment Investments, Inc. partnership focused on the John H. Wyant media, communications and President of Blue Chip Venture entertainment industry. Also Company, a venture capital President and Chief Executive investment firm. Officer of Sutton Capital Associates, Inc., an investment management firm specializing in cable television, wireless teleph- ony and related industries. Albany, NY Covington, KY Flint, MI Palmdale, CA Utica-Rome, NY Stockholder Information WQBJ (FM)* Corporate WCRZ (FM) KTPI (FM) # WODZ (FM) Corporate Offices General Counsel Stockholders whose stock is WQBK (FM)* Headquarters WWBN (FM) KOSS (FM) # WLZW (FM) Regent Communications, Inc. Strauss & Troy held in street name are encour- 50 East RiverCenter Boulevard Cincinnati, Ohio aged to visit our web site at WABT (FM)* WFNT (AM) KAVC (AM) # WFRG (FM) El Paso, TX Suite 180 www.regentcomm.com and FCC Counsel WGNA (FM)* WRUN (AM) Covington, Kentucky 41011 subscribe to our financial mail- KSII (FM) Grand Rapids, MI Redding, CA Latham & Watkins WGNA (AM)* WIBX (AM) (606) 292-0030 ing list, enabling them to receive KLAQ (FM) Washington, D.C. WTMM (AM)* WLHT (FM)* KSHA (FM) notification of issuance of annual KROD (AM) Transfer Agent and Registrar WGRD (FM)* KNNN (FM) Victorville, CA Auditors and interim reports without delay. Fifth Third Bank Chico, CA WTRV (FM)* KRDG (FM) KZXY (FM) # PricewaterhouseCoopers Erie, TX Corporate Trust Services Annual Meeting # Cincinnati, Ohio KFMF (FM) KRRX (FM) KATJ (FM) 38 Fountain Square Plaza The Annual Meeting of WXKC (FM) Mansfield, OH KALF (FM) KNRO (AM) KIXA (FM) # MD 10AT66 Publications Stockholders will be held on WXTA (FM) # KQPT (FM) WYHT (FM) KQMS (AM) KROY (AM) # Cincinnati, Ohio 45263 The Company’s Annual Report, Thursday, May 18, 2000 at WRIE (AM) # KZAP (FM)* WSWR (FM) KIXW (AM) # (513) 744-8676 Form 10-K and Quarterly 10:00 A.M., local time, at the # Reports to Stockholders are Metropolitan Club, 50 East Flagstaff, AZ WMAN (AM) St. Cloud, MN Investor Relations available free of charge to stock- RiverCenter Boulevard, KZGL (FM) # KMXK (FM) Watertown, NY Brainerd Communicators, Inc. holders. Copies of the exhibits Covington, Kentucky. WWJO (FM) WCIZ (FM) New York, New York KVNA (FM) # to those reports are also available Contact: KVNA (AM) # WJON (AM) WFRY (FM) upon payment of a fee covering John R. Buckley WTNY (AM) the Company’s reasonable Phone: (212) 986-6667 expenses of processing and WUZZ (AM) Fax: (212) 986-8302 shipping. Inquiries are welcome E mail: by letter to the Corporate *Stations indicated with an asterisk (*) are subject to acquisition by us under an existing agreement. [email protected] Offices or by e-mail to investor- # We have agreed to sell those stations indicated with a pound sign (#). [email protected]. Regent Communications, Inc. (“Regent” or the “Company”) is a holding company in the radio broadcasting business. Regent was incorporated in Delaware in November 1996 by Terry S. Jacobs and William L. Stakelin with the objective of acquiring radio properties, primarily in medium and smaller radio markets, that have a history of growing revenues and broadcast cash flow, have capable operating management and are in communities with good growth prospects or have attractive competitive environments. Regent acquired its first group of radio stations in June of 1998. Pending the close of all announced transactions, Regent Communications will own and operate 40 stations (28 FM and 12 AM) clustered in 10 markets in California, Michigan, Minnesota, New York, Pennsylvania and Texas. Regent Communications, Inc. shares are traded on the Nasdaq under the symbol “RGCI”. REGENT COMMUNICATIONS ANNUAL REPORT 1999 Letter to Our Shareholders TO OUR SHAREHOLDERS, CUSTOMERS AND EMPLOYEES: The year 1999 was one of significant growth, achievement and building for Regent. The changes, investment and upgrading Regent accomplished in 1999 have positioned the Company for accelerated long-term growth. It is with pleasure and enthusiasm that I share with you our developments, accomplishments, performance to date, and view for Regent’s future. This was “Year One” for the majority of our quarters of 1999, respectively, and closed stations and we concentrated on implement- on El Paso, Utica/Rome and Watertown at ing our sales, marketing and programming the end of January 2000. practices, while also focusing on acquiring new markets. We spent a large amount Recent Developments of our time and resources on positioning ith all of the hard work and invest- Regent for long-term growth, realizing that ment in 1999, we also filed with often in our small and mid-size markets we Wthe Securities and Exchange must take a step backward before we can Commission a registration statement for an leap forward to fully exploit our long-term Initial Public Offering (IPO). We completed opportunities. Additionally, we focused on this IPO in January 2000 and raised over creating an infrastructure of management, $156 million through the sale of 18,400,000 Terry S. Jacobs financial systems and controls and a station shares of our common stock at $8.50 per Chairman of the Board and and market platform to support a much share. In conjunction with this IPO, all of Chief Executive Officer larger Company. Regent’s former series of convertible preferred stock were either redeemed or converted to During the year we negotiated the divestiture shares of common stock on a one-for-one of stations in some of our smaller markets basis. We are very proud that our stock that did not meet our strategic criteria for to date has traded at a price significantly building Regent in the future. At the same higher than its initial offering price. time, we negotiated the acquisition of sta- tions in five excellent new markets to add With the highly successful IPO we strength- to and significantly upgrade Regent’s platform. ened our financial position and closed on These markets include St. Cloud, Minnesota; the El Paso, Utica/Rome and Watertown Erie, Pennsylvania; El Paso, Texas; Utica/ acquisitions. We also entered into a new, Rome, New York; and Watertown, New significantly larger, credit facility, which York. We completed the acquisition of puts the Company in an excellent financial St. Cloud and Erie in the second and third position to take advantage of future acquisition opportunities. An example of this are often characterized by undercapitalized is that we were able to negotiate another sig- “mom and pop” operators. By implement- nificant upgrading of our market platform in ing professional product, market research March 2000, when we entered into an agree- and selling practices not normally employed ment with Clear Channel Communications. by smaller operators, we are able to better Through this transaction, we will exchange serve our listeners and advertisers in a cost three of our smaller “non-rated” markets effective manner. Finally, these markets are (Mansfield, Ohio, Palmdale/Lancaster and generally recession resilient as local advertis- Victorville, California) plus $67 million ing makes up the majority of advertising in cash for two very attractive mid-sized revenues. markets, Albany, New York and Grand Rapids, Michigan. As radio revenue markets Our overall business strategy is to enhance #56 and #59, respectively, these two markets and improve the markets we currently operate will now be the largest in Regent’s portfolio in, while entering new markets where and represent excellent growth potential that we can achieve a leadership position. We should help us significantly upgrade our employ a very disciplined acquisition strategy ability to increase shareholder value. as we evaluate our growth opportunities. We seek to acquire positions that will allow Looking Forward – Building us to achieve the #1 or #2 revenue rank Shareholder Value within the market. The stations must have egent’s primary commitment has been, strong technical facilities with signals serving and always will be, to build share- the whole market. We must be able to Rholder value, and we believe that we generate at least $1 million in BCF within have a sound corporate strategy to fulfill the cluster in a reasonable time frame after this commitment. entering the market.