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Our Founder
Rob Reynolds
Teacher. Real Estate Entrepreneur. Father. Committed to Inspiring Others to Imitate Christ.

Rob Reynolds is the Founder of Cross Boss Media.  From 2004-2011, Rob taught in the New York Public School system, teaching high school biology, chemistry, and psychology. Concurrently, beginning in 2005, Rob invested in multifamily real estate as an owner-operator. In 2010, he co-founded Avesta, a Tampa-based multifamily real estate investment and management company, and ended his teaching career in June of 2011 to relocate and focus on real estate full time.

As president, Rob helped grow Avesta to 450 employees and $1.7 billion in real estate assets; he also led the company’s culture, resulting in national recognition as #19 in Fortune’s Top 100 Medium Workplaces and regional finalist for E&Y’s international Entrepreneur of the Year in 2017.

Reynolds Family

In 2018, Rob left Avesta to pursue a deep conviction to launch what has become Cross Boss Media, with its mission “to provide children a genuinely entertaining, secure place to encounter Christ in a way that inspires action.”

Rob is passionate about Christianity and his Catholic faith, rooted in his upbringing and education, and reinforced through faith-centered friendships and regimented prayer life. Rob was pre-med in college and graduated from Franciscan University of Steubenville in 2004, with a BA in Biology and Theology, minoring in Chemistry. He has a MS in Adolescence Education from Mercy College, and a MS in Instructional Technology. He is a Certified Property Manager (CPM®).

Rob has been married to his wife, Marya, since 2006, and is a devoted father to six daughters.

  • Brought and led That Man Is You! men’s weekly fellowship program and led group of 100+ men for 3 years prior to launching the Society of St. Joseph
  • Co-founded the Society of St. Joseph, a men’s Catholic fellowship organization focused on the three pillars of faith formation, works of mercy, and family leadership
  • President, Tampa Bay Chapter of Legatus
  • Advisory Board Member, Dr. Scott Hahn’s St. Paul Center for Biblical Theology
  • Diocese of St. Petersburg’s 2017 St. Jude the Apostle Medal for exceptional service to the parish
  • Franciscan University of Steubenville’s 2018 Professor Edward J. Kelly Award for excellence in business