In 1970, after graduation from Loyola University of Chicago and a year of law studies at The John Marshall Law School, Grotto began his career with the NBC Network. Grotto was the Division's top salesman for four of his five years of employment at NBC.
Grotto's national reputation as an outstanding media salesman and his world class ranking as a one-design sailor resulted in Ted Turner personally recruiting Grotto as a sales executive to launch his superstation and later CNN. Grotto's association and contributions to the success of Turner's media endeavors lead to a succession of high profile senior management positions in the television and cable industries throughout his twenties and early thirties. These included Vice President Corporate Development, Viacom International; General Manager, Group W Television and Cable; and Senior Vice President General Manager, LBS Television Syndication.
In 1983, Grotto was recruited as a founding member of Taussig and Associates, a Washington D.C based private equity firm that invested in turn-around companies. As a principal and partner, Grotto's functional responsibility was new revenue generation for the Firm's investments through high-powered sales, joint venturing, and strategic partnering. In the seven years Grotto was with the Firm, he was a principal manager on United Press International, Data Broadcasting Corporation, Intellitek Computer Corporation, and Comtex. All but Intellitek (which was sold to First Data) were or became publicly traded companies.
In 1990, Grotto founded EDT Incorporated, a network software company. Through mapping and imaging technology, EDT provided a universal interface for the NEIC Medical Claims Network. Grotto was named "Entrepreneur of the Year" in 1991 by GTE. EDT was sold through a merger in 1994.
In 1994, Grotto co-founded AGS Financial Corporation, a New York based Merchant Bank. AGS was a registered broker-dealer with the NASD and the U.S. Securities and Exchange Commission. AGS made investments in the communications, network, and multi-media sectors. AGS was sold in 1997 to Enhance Financial Services of London, England.
In 1997, Grotto co-founded Royal Oak Holdings, LLC and Royal Oak Capital Corporation of New York City. Through Royal Oak Grotto founded, funded, and launched Hullspeed, LLC and the Loan Network Corporation. In 2001 Hullspeed was sold to The Boat Corporation of America (Boat/US) and the Loan Network was sold to a private equity firm.
Throughout 2000 and 2001, Grotto was Chairman and Chief Executive Officer of Busybox.com., a forerunner of Youtube. Under Grotto's leadership, Busybox raised over $10 million in private equity and over $15 million was raised in an IPO on the NASDAQ Exchange in June 2001 at $8.00 per share. Grotto resigned from Busybox in November of 2001.
In 2003, Grotto co-founded Diversified Media Holdings, Inc. an international intellectual property firm. DMH did a reverse acquisition of a NASDAQ traded company. It was sold to a Japanese media firm in 2004.
In 2004, Grotto became a Swiss resident and founded a Swiss AG, International Media Network of Zurich, Switzerland. IMN's mission was to purchase intellectual property that could be exported from Europe to the United States. IMN was dissolved in 2005.
From 2005 to the present, Grotto is an advisor to several European and Asian family offices, several US firms, and a Japanese firm in the acquisition and development of intellectual property assets worldwide.