David Chessler

David Chessler

David Chessler is a Sarasota-based entrepreneur with extensive experience investing and running businesses of all sizes. He serves as the Chief Investment Partner of the Great White Shark Opportunity Fund, an initiative launched with PGA golfer Greg Norman that supports smaller businesses.

He is also the president and founder of Chessler Holdings, a diversified investment firm with investments across various industries. Currently, he’s collaborating with two other entrepreneurs on the redevelopment of Main Plaza in downtown Sarasota.

Early Life and Education

David Chessler spent his early childhood living with his parents, where he attended school alongside them.

David Chesler graduated from the University of Michigan and then went on to receive his doctorate in immunology from New York University.

He then joined Cravath, Swaine & Moore in Manhattan where he worked for many years before leaving to launch his own company.

His first business venture was ParView, a company that outfitted golf carts with global positioning systems and Wi-Fi networks. The business took off quickly, earning several entrepreneur awards along the way.

Professional Career

David Chessler is an accomplished executive who has dedicated most of his career to the business world. His innovative leadership style and creative investing abilities have resulted in multiple entrepreneurial successes as well as value-added investments in small to mid-cap companies.

His most noteworthy achievement was leading the company that developed and patented the first GPS-based telematics device, leading to its successful exit to Ingersoll-Rand. He has a knack for turning around troubled businesses through strategic partnerships, capital raising and deal structuring. Furthermore, he is an active real estate investor – including purchasing Main Plaza/Hollywood 20 on Main Street in Sarasota with investors Eric Baird and Jesse Biter. Furthermore, he serves on board of several companies and currently serves as Chief Investment Partner of Great White Shark Opportunity Fund.

Achievements and Honors

David Chessler is an accomplished musician as well as a philanthropist with a heart for charity. He has donated millions of dollars in scholarships to students, with his most recent donation being a ten room resort in Las Vegas for those lucky winners. Furthermore, David serves on the faculty at UC San Diego Jacobs School of Engineering where he has been recognized as a Distinguished Alumnus. Additionally, David strongly advocates for campus initiatives promoting gender equity and community engagement.

Personal Life

David Chessler is an acclaimed businessman and entrepreneur with experience across various industries. His expertise lies in creating successful turnarounds as well as value-added investments for small to mid-cap companies.

Sarasota resident John Barto has been actively engaged in several projects, from redeveloping Main Plaza to investing in cannabis. Currently, he oversees the Great White Shark Opportunity Fund – a partnership with PGA golfer Greg Norman that seeks out opportunistic businesses.

He built Sarasota-based GPS Industries into a national leader in selling high-end GPS systems for low speed vehicles, particularly golf carts. Additionally, he invested in commercial real estate; he was one of three entrepreneurs who purchased the 8.6 acre Main Plaza site downtown last year with plans to redevelop the area and breathe life back into downtown.

Net Worth

Chessler is the founder and owner of a Sarasota-based investment group that holds and manages diversified investments across multiple industries. Additionally, their startup business program at University of South Florida gives undergraduate students valuable business experience.

Hustle offers undergrads the unique opportunity to compete for money and other prizes while learning how to run a real company. According to Chessler, this experience can be instrumental in their future success in the workplace.

Chessler founded GPS Industries, a business that outfitted golf carts with global positioning systems and Wi-Fi networks. He has invested in various other ventures such as cannabis cultivation and home decor. Most recently, he sold part of Main Plaza in downtown Sarasota for $20 million to two partners.

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