While still in college, Jason was already working full time.  First as a press secretary to candidate for Mayor of Washington, D.C., and then as a Communications Director to a member of the City Council.  In 1999, while still in college, he served as an aide during the Clinton Impeachment proceedings to Former White House Special Counsel Lanny Davis.  After graduation from The George Washington University, with a degree in Political Communication, Jason joined the staff of author Gail Sheehy, where he helped direct research into her bestselling autobiography of Hillary Clinton, Hillary’s Choice.  He then worked with Gail on articles that appeared in Vanity Fair.  

At the age of 23, Jason ran for public office and sought a seat on the NYC City Council.  The election took place on 9-11-01. The 9-11 terror attacks would bring an end to the election.  Two weeks later, a rescheduled election was called and Jason was defeated. He was then hired as a staffer for Assemblymember Scott Stringer.  Jason worked on local policy issues including housing, transportation, health care, and government reform. After Stringer was elected as Manhattan Borough President, Jason was appointed by the Assembly Speaker to serve as the interim replacement.  While representing the District for several months, Jason helped constituents with housing needs and helped secure a sizable donation to Upper West Side public schools by allowing the film, A Night at the Museum, to shoot in the office (yes, Jason did get a cameo in the movie).  

In 2006, Jason received his Master’s Degree from Columbia University’s School of International and Public Affairs.  He was quickly offered a teaching position at John Jay College, which he held for 5 years and became one of the most popular professors on campus.   

While teaching, he also began his career in real estate.  First working for his aunt, Toni Haber, a top producing agent at Compass, and then he went out on his own.  In 2009, after refusing to rent an apartment to Libyan leader Muammar Gaddafi, he decided to start his own firm with a social purpose.  In 2010, he and his brother co-founded Rubicon Property, a social entrepreneurial firm. Growing the firm from his living room floor, to a thriving boutique business, the company was sold to Warburg Realty in 2014.   

Investing in real estate has always been important to Jason. His family have made strategic purchases in vacant properties across NYC.  He’s also an investor in the real estate health and wellness technology startup, Delos Living.

In 2016, Jason’s first book, The Business of Good, was published to wide acclaim.  The book has become a must-read for those interested in social entrepreneurship.  The book has spawned a Facebook Live show with Entrepreneur Magazine, called The Business of Good Live, which reaches a large audience with each livestream.  

In 2019, Jason began a new urban planning lecture series on Robert Moses and Jane Jacobs and launched a podcast based on his lectures called  FutureCity.

In 2022, he sold over $150MM worth of residential real estate in NYC.  His $70M sale at 432 Park Avenue was one of the top sales of the year and the highest since the onset of the COVID-19 pandemic.  In 2023, he expanded his business to include working in both NYC and South Florida.

In the fall of 2023, Jason founded the NAR Accountability Project, which became the leading voice for change at the National Association of Realtors.  Over 3,000 agents in all 50 states have joined Jason’s efforts to reform the real estate industry.

Jason splits his time between NYC and Boca Raton, FL.