Jonathan Chaltain was born in Madison, Wisconsin and raised in Austin, Texas. He earned his undergraduate degrees in Plan II Honors and Asian Studies from the University of Texas at Austin, and he graduated with honors from the University of Texas School of Law, where he was a member of the Texas Law Review, the American Journal of Criminal Law, and Chancellors.

For two years after graduation, Jonathan served as a briefing attorney for the Honorable Justice Terry Jennings of the Texas First Court of Appeals, where he assisted in drafting numerous opinions covering a variety of appeals. He now practices commercial and insurance litigation, primarily focusing on insurance coverage litigation, insurance fraud and premium litigation, judicial review of administrative decisions, and related appeals.