Gladstone recently founded Mockingbird Equity, a venture capital firm targeting the music industry.  Prior to Mockingbird, Gladstone was a founding member of the law firm Gladstone Baker Kelley, PLLC.  He consults clients on entity formation, business planning and funding for entertainment businesses and projects, and has operated his own artist management and music publishing companies, an entertainment service business holding company, a sporting product manufacturing and sales company, and a professional seminar company.  

Gladstone is regarded as the pre-eminent business plan designer and writer for entertainment companies, in new and growth markets, and consults with creative entrepreneurs, intellectual property creators and business owners.  He is the architect of a groundbreaking liaison with Private Capital Advisors, LLC.  The coalition of this investment banking firm and the Gladstone Baker Kelley law firm is a first for the Nashville financial and entertainment communities.

Gladstone is also a featured speaker and founder of "Raising Money For Music" seminars; organizer and presenter of "Asset Securitization in the Music and Entertainment Industry" seminars; Co-Founder and Chairman, Film Music Workshop, Inc.; international panelist and speaker on various music industry legal topics; quoted in trade magazines on music business matters; featured panelist for many music industry symposia and conferences.  Since 2005, as Associate Professor at the Loyola University School of Business, he designed and lectures in the "Music Finance" course, and has co-written the subject's textbook.
Gladstone also has significant experience as a professor, lecturer and teacher at the college and adult education levels. He has traveled extensively throughout Europe as an artist manager and independent label record executive.

Gladstone is a member of Leadership Music Class of 1999, CMA, NARAS, Nashville Bar Association Entertainment and Sports Law Committee, International Association of Entertainment Attorneys, AMA Board of Directors, Chairman, Finance Committee (2004).