He was born March 14, 1961, in McAllen, Texas, the fourth of six children, including a fraternal twin brother. During the Depression, his family had moved to the fertile Río Grande Valley along the Texas-Mexico border, where they were citrus farmers. His father, Samuel Weisfeld, died of heart failure in 1971 at the age of 44, when Herschel was 10 years old. Following her husband's death, his mother, Sara Ellen, sold the family business. She later married Albert Gerrick of Los Angeles, California.

Weisfeld's love of art came at the feet of his mother, who had studied art herself and was a founding member of the National Museum of Women in the Arts in Washington, D.C., part of the Smithsonian Museum. She felt art was an important part of life and exposed her six children to all the fine arts, including visual arts, classical music, dance, and theater. She died in 1996 of breast cancer.

Weisfeld graduated from McAllen Memorial High School and attended Tulane University in New Orleans, Louisiana, where he was a member of Alpha Epsilon Pi fraternity, holding several offices. He graduated in 1983 with a Bachelor of Science in Management (B.S.M.), with a concentration in accounting.

His interest in real estate was piqued while still in high school, and he took night classes to prepare for a real estate license, which he obtained shortly after reaching the required age of 18.

After graduating from Tulane, he joined the McAllen commercial real estate firm, Action Realty, handling commercial rental properties.
In 1984, Weisfeld was hired as assistant to Robert H. McKenzie-Smith, chairman of The Americana Group of Companies, Inc., based in the Dallas suburb of DeSoto, which prompted his move to Dallas. Americana was a vertically-integrated real estate and financial services company with sales in excess of $100-million. His duties included overseeing major projects, including a Duncanville townhouse development, a mixed-use development in DeSoto, as well as industrial land developments.

During the time he worked at Americana, Weisfeld began building his own portfolio, acquiring residential income-producing properties in Dallas's Oak Cliff neighborhood. He formed HeRo Investments with his younger brother, Ronald. They took advantage of the depressed Texas real estate market of the time, acquiring residential properties at FDIC and RTC auctions.

As Weisfeld and his brother grew in their own directions, Herschel started his own company, Weisfeld Real Estate & Development (W.I.R.E.D.), focusing on acquiring older properties with the idea of refurbishing them and creating re-adaptive uses, rather than tearing them down. His maverick real estate philosophy is a spin on the industry cliché of upgrading a property to its "highest and best use." He believes that "highest and best use" can mean restoring an existing structure, rather than tearing it down. He also prefers to provide accessible opportunities for tenants who otherwise couldn't afford to locate in a neighborhood.

Weisfeld also owns properties in his native Río Grande Valley, one of the fastest-growing areas in the U.S., and he manages a partnership for his siblings, Weisfeld Properties, Inc. Prior to building the Sara Ellen and Samuel Weisfeld Center, Weisfeld's company acquired numerous properties in the Oak Lawn-Turtle Creek and Oak Cliff areas of Dallas, including single-family, multi-family, office, commercial, and retail buildings. One unique project in Oak Lawn was the conversion in 1995 of the former Dallas County Mental Health/Mental Retardation Building at 3601 Routh St. into a building Weisfeld dubbed

"S.O.T.A: 'State of the Art," Dallas's first hybrid executive office suites/private art museum. The building, which contains 21 office suites, also has on display in its common areas over 150 museum-quality pieces of fine art and sculpture from Weisfeld's personal art collection. The SOTA art collection is available for viewing by the public free of charge during normal business hours, by appointment only.

Weisfeld is actively involved as a leader in the Dallas community in professional, civic, and arts endeavors. He is on the Dallas Mayor's Commission on Homelessness, a subcommittee of the Homeless Consortium, for which he chairs the Public Feeding subcommittee. He is also vice president of the Oak Lawn Committee, a neighborhood planning and zoning review board of the City of Dallas's Planned Development District 193 that oversees development of the Uptown/Oak Lawn-Turtle Creek areas.

He also serves as president of Cedar Springs-area Stakeholders, a crime watch organization for the Oak Lawn-Turtle Creek area, and he is a member of the Cedars Crime Watch covering the Cedars neighborhood, where the Weisfeld Center is located. In addition, he is a 1999 graduate of the Dallas Citizens' Police Academy.

Weisfeld is a former board member of Best Southwest, the chamber of commerce comprising five southwest Dallas suburbs. He also is a graduate and past board member of Leadership Southwest and of the Ladonia Foundation, a residency program in Ladonia, Texas, for artists In recognition of his being a pioneer in the Dallas arts community, Weisfeld was asked to be a presenter for the 1999 Leon Rabin Awards ceremony, given annually by-- and to-- the Dallas theatrical community.

The Weisfeld Center is a sponsor of the Dallas Museum of Art's Beaux Arts Ball 2000, and Weisfeld has held memberships in the McKinney Avenue Contemporary (MAC), Dallas Arboretum, Dallas Zoo, Dallas Visual Arts Center, and the Contemporary Museum of Fort Worth.