Harold Wolpert (he/him), Founder and CEO of My Purple Crayon Advisors, is a three-time Tony Award–winning arts leader, strategist, and teacher with deep expertise in nonprofit theatre leadership, organizational advancement, and producing. His core values of integrity, authenticity, and decency underpin his respect for artists and institutions alike. As Anna Deavere Smith has said, “There’s much to appreciate about Harold. What I’ve liked most is his spirit of radical hospitality. Quite simply, he’s a classy cat.”
Harold has served in executive leadership positions for the internationally-acclaimed Roundabout Theatre Company, Manhattan Theatre Club, Signature Theatre, and Alley Theatre. He has collaborated with preeminent theater artists on more than 250 Broadway, Off-Broadway, and LORT productions, including Pulitzer Prize and Tony Award-winning works, as well as West End and Venice Biennale productions, national tours, transfers, international collaborations, and HD films. Nationally, Wolpert is recognized as a leader in the theatre field through years of service advancing sector-wide collaboration.
My Purple Crayon Advisors collaborates with nonprofit arts organizations navigating moments of transition, growth, or recalibration. The practice focuses on organizational advancement, sustainability, and leadership development, producing actionable solutions that build durable capacity to support mission delivery. Clients include organizations across all stages of growth, among them Williamstown Theatre Festival, Cape Playhouse, Wilma Theater, McCarter Theatre Center, Jazz Houston, Miami New Drama, IndieSpace, Breaking the Binary Theatre, Ford’s Theatre, and Goodspeed Musicals.
Harold is also a longtime teacher and mentor. He serves on the faculty of Yale’s David Geffen School of Drama, where he champions theater management graduate students preparing for leadership roles in the arts.
His civic engagement and leadership in organizations supporting the LGBTQ+ community include volunteering for 10 years for The Trevor Project, the leading suicide prevention and crisis intervention nonprofit organization for LGBTQ+ young people and serving as Board Chairman of AIDS Foundation Houston.
Originally from Philadelphia and a graduate of the University of Pennsylvania, Harold lives in Brooklyn with his cat, Joey, who (occasionally) serves as his (unreliable) assistant.