Chrysalis was an original investor in Regent Communications, a Covington, KY-based owner/operator of radio stations in mid-size markets. Regent was acquired in 1997 by Jacor Communications, which subsequently merged with Clear Channel Communications (NYSE: CCU) in 1999.

Chrysalis was an original investor in Compliance and Ethics Learning Solutions(CELS), a Chicago-based holding company created to target the compliance training sector which subsequently acquired Midi, Inc., a leading provider of off-the-shelf and custom compliance and ethics eLearning solutions. The company was acquired by SAI Global Limited (ASX: SAI), a global provider of standards, compliance and business improvement solutions, in January 2007.

Chrysalis invested in Tritel Communications, a Jackson, MS-based startup that went public and subsequently merged with TeleCorp PCS. TeleCorp PCS was acquired by AT&T Wireless in February 2002. In October 2004, Cingular Wireless LLC, a joint venture between SBC Communications Inc. and BellSouth Corp., acquired AT&T Wireless, creating the nation’s largest wireless provider. In 2005, the merger of SBC Communications Inc. and AT&T Corp. created a new AT&T which subsequently acquired BellSouth and took full control of Cingular Wireless.

Chrysalis was an original investor in Louisville, KY-based Appriss (formerly Interactive Systems, LLC), the leading provider of innovative technology solutions that assist law enforcement efforts and improve the efficiency and effectiveness of criminal justice agencies. The company secured a strategic investment from Bain Capital Ventures and JMI Equity in July 2007.

Chrysalis invested in Oklahoma City, OK-based Advanced Academics, a leading provider of online secondary education. The company was acquired by DeVry Inc. in November 2007.

Mobile Armor, St. Louis, MO, a provider of authentication and encryption software solutions that secure data at rest on laptops and portable devices.  The company was acquired by Trend Micro in February 2011.