Billionaire Profile
David Siegel
Global Rank
#443

Image: Public domain | via Wikimedia Commons

David Siegel

CEO, Westgate Resorts
US
Real-Time Net Worth
$0.5B
As of December 2025
Age
89
Source
Timeshares
Industry
finance-investments
Citizenship
US

Biography

David Siegel (May 3, 1935 – April 5, 2025) was an American businessman best known as the founder of Westgate Resorts. Starting his career in real estate, he built Westgate Resorts into the largest privately-held timeshare company in the world. Siegel's wealth source was primarily timeshares, and he was a prominent figure in the finance and investments industry. Throughout his career, Siegel received numerous accolades, including the ARDA Lifetime Achievement Award in 2025. After the tragic loss of his daughter, Victoria, he founded the Victoria's Voice Foundation to combat the opioid epidemic.

Wealth Over Time

In-Depth Profile

Early Life

David Alan Siegel was born in Chicago, Illinois, on May 3, 1935. His parents were Sadelle and Sid Siegel, a grocer. In 1945, the family moved to Miami, Florida, where David would grow up. He graduated from Miami Senior High School in 1953 and studied marketing and management at the University of Miami, though he did not complete his degree.

Rise to Success

Siegel's entrepreneurial journey began in the real estate sector. He founded Central Florida Investments in the early 1970s, before being introduced to the timeshare concept in 1982. He built 16 villas which became Westgate Vacation Villas. Under his leadership, the company grew into the largest privately held timeshare company in the world. Westgate Resorts expanded to include over 25 resorts across the United States, boasting more than 13,500 rooms. In addition to timeshares, Siegel was involved in real estate, construction, hotel management, travel services, and retail.

Key Business Strategies

Siegel's success was attributed to his ability to identify and capitalize on the growing market for vacation ownership. He focused on providing affordable vacation ownership opportunities, utilizing innovative marketing strategies to reach middle-class consumers. He also diversified his business ventures beyond timeshares, which contributed to his overall wealth. Notably, Siegel was known for his hands-on approach and his ambition, which led to the expansion of his business ventures.

Philanthropy

Following the death of his daughter Victoria in 2015 due to an accidental drug overdose, Siegel and his wife, Jackie, established the Victoria's Voice Foundation. The foundation's mission is to raise awareness about opioid abuse and support prevention efforts nationwide. The foundation advocates for youth drug education, increased access to naloxone, and legislative reform. They also supported other community initiatives through the Westgate Foundation, awarding over $1 million annually for community needs and team member support.

Career Milestones

1982

Founded Westgate Resorts

Established Westgate Resorts, which became the largest privately-owned timeshare company in the world.

2015

Founded Victoria's Voice Foundation

Established a foundation to combat the opioid epidemic after his daughter's death.

2025

Received ARDA Lifetime Achievement Award

Honored for his lasting contributions to the timeshare industry.

Philanthropy & Social Impact

Addiction Prevention

Victoria's Voice Foundation

N/A

Provides drug education and addiction-prevention support.

Business Philosophy & Leadership

Leadership Principles

Entrepreneurial Spirit

Embodied the American spirit of entrepreneurialism and business success.

Philanthropy

Dedicated to ensuring no other family shared the same tragedy his family did.

Controversies & Challenges

2008

Sexual Harassment Lawsuit

Siegel was found liable in a sexual harassment lawsuit.

2012

Email to Employees

Sent an email to employees suggesting that a victory for Barack Obama could lead to layoffs or changes in company operations.