Entrepreneurs come up with new ideas and start businesses based on them. They forgo the security of a salaried job to take on their own endeavor, assuming all the risk in hopes of great rewards. A serial entrepreneur takes on this challenge repeatedly. Once a particular business is established, they delegate the responsibility of running its operations and move on to other ventures. They may even sell earlier businesses.

Serial entrepreneurs also frequently experience windfall gains when their companies are sold at high premiums or continue to generate profits without much effort on their part.

This article lists, in alphabetical order, 10 of the top serial entrepreneurs; it's not exhaustive nor is it a ranking.

1. Andreas von Bechtolsheim

The co-founder of Sun Microsystems was instrumental in building the company—founded in 1982—into a billion-dollar business. In 1995, he left Sun and established Granite Systems which manufactured network switches. Within a year, it was sold to Cisco Systems for $220 million.

Bechtolsheim launched a server technology company called Kealia in 2001, which was sold to Sun Microsystems in 2004, bringing him back to the Sun management team. Following that, he co-founded Arista Networks in 2005, a high-speed networking firm. He also co-founded HighBAR ventures, a venture capital investment firm that has invested in many technology start-ups. He was one of the early investors in Google, investing $100,000 in 1998, before Google, Inc. was even established as a company. His net worth, in 2018, is around $6.7 billion.

2. Sir Richard Branson

The foundation of business conglomerate Virgin Group dates back to 1970, when 20-year-old Richard Branson started a mail-order record business. Today, the Virgin Group owns over 200 different companies, each controlled by different shareholders. His diversified set of businesses spans across multiple products and services.

For every successful company under the Virgin brand, like Virgin Atlantic and Virgin Music, there are many other unsuccessful Virgin companies, like Virgin Cola, Virgin Brides, Virgin Vodka, and Virgin Clothing.

3. Rod Drury

Drury is a New Zealand-based serial entrepreneur in the technology space. In 1995, he established Glazier Systems, which focused on software development and consultancy services. He eventually sold it off in 1999 for $7 million. He then founded AfterMail, which was acquired by Quest Software for $15 million in 2006.

Drury went on to establish Xero in 2006, a software-as-a-service (SaaS) company. He also co-founded a company called Pacific Fiber, which attempted to build an internet cable connecting the United States with Australia and New Zealand, though it didn't succeed. In 2017, he sold $95 million worth of Xero shares, and he moved from the role of CEO to non-executive director in March 2018.

4. Janus Friis and Niklas Zennström

These billionaire Scandinavian entrepreneurs have numerous tech ventures to their names. The peer-to-peer file sharing service called Kazaa was their brainchild, but the pair came into the limelight with Skype, which was the first prominent computer-to-computer voice and video calling service.

Friis and Zennstrom sold Skype to eBay, Inc. for $2.6 billion in 2005. Zennstrom rejoined Skype in 2007, before it was sold to Microsoft in 2011 for $8.5 billion. Today, Zennstrom is focused on Atomico, an investment consortium that has invested in over 50 technology companies. Janus Friis went on to found Starship Technologies in 2014.

5. Omar Hamoui

Hamoui, who dropped out of the MBA program at The Wharton School at the University of Pennsylvania, has established four different companies. The most prominent one among these was Admob, which was a mobile advertising network platform. Admob was sold to Google in 2009, for $750 million. His other ventures also include Fotochatter, a mobile photo-sharing network, and Maybe, Inc. which was acquired by LinkedIn in 2013. He is currently a partner at venture capital firm Sequoia. 

6. Wayne Huizenga

This American business tycoon with a net worth of $2.6 billion is credited with founding three multi-billion-dollar companies, all part of Fortune 500 companies. They include Waste Management, Inc., founded in 1968, with a single garbage truck; Blockbuster video in 1987, which become a leading movie rental chain; and AutoNation in 1996, which became the largest automotive dealer in the U.S.

Huizenga has owned three sports franchises: the Miami Dolphins, Florida Marlins, and Florida Panthers. He also had a hand in founding six successful NYSE-listed companies. Huizenga passed away on March 22, 2018 at age 80.

7. Josh Kopelman

Kopelman started his entrepreneurial spree while at Wharton. In 1992, he established Infonautics Corp., which successfully went public in 1996. In the next few years, he founded several online businesses, including Half.com for used books and music gadgets, and TurnTide, which was an anti-spam system. Half.com was acquired by eBay less than a year after it started, and TurnTide was purchased by Symantec Corp. within six months.

Kopelman is currently the managing director of First Round Capital, which has been funding Internet companies for the last 20 years. In 2018, he was ranked the third top venture capitalist by the New York Times. His investments include Mint.com and StumbleUpon.

8. Michael Rubin

With an estimated net worth of $3 billion in 2018, Michael Rubin is an established internet and sports serial entrepreneur. Even before he went to college, Rubin acquired a chain of five ski-shops in his hometown of Lafayette Hill, Pa. He later established KPR sports, a sports equipment company, which hit $50 million revenues by 1995. His 1998 venture, Global Sports, which was later called GSI Commerce (a billion-dollar e-commerce venture), was purchased by eBay for $2.4 billion.

Later, eBay sold three consumer divisions back to Rubin, who merged them together to form the present-day Kynetic. It includes Fanatics, Inc., (sports merchandise seller), Rue La La (flash sale site), and ShopRunner (member-based service portal dedicated to online shoppers). Rubin has also invested in the Philadelphia 76ers basketball team and the New Jersey Devils hockey team.

9. The Samwer Brothers

Entrepreneurship isn’t just about unique ideas; it’s also about borrowing best practices and perfectly executing them. Based in Germany, The Samwer brothers—Alexander, Marc and Oliver—established Alando, which was known to be a replica of eBay. It eventually sold to eBay in 1999 for $50 million.

The Samwer Brothers' next venture, Jamba!, was founded in 2000, offered SMS mobile content, including ringtones, online gaming, online dating, and insurance services for mobile phones. Jamba! was sold to VeriSign in 2004 for $270 million. In 2007, they founded Rocket Internet SE, which served as a parent company used to replicate successful global businesses in local markets. It is now successfully involved in funding startups for various internet companies, including Foodpanda, Home24, Spotcap, and HelloFresh.

The Samwers were also early investors in Facebook in 2008. Each Samwer brother’s net worth is at least $1.2 billion.

10. Oprah Winfrey

This famous American philanthropist, media leader, and entrepreneur, best known for her award-winning talk show, “The Oprah Winfrey Show,” started her career as a local TV anchor. In 1986, she established Harpo Productions, Inc., which owned the rights to the “The Oprah Winfrey Show” from 1988 onward, establishing the foundation of her entrepreneurial ventures.

By the end of the 1990s, Oprah was the wealthiest woman in show business, and her net worth in 2018 is $2.8 billion. She is a co-founder of Oxygen, a cable station, and she launched the Oprah Winfrey Network (OWN) in 2011. She publishes the O, The Oprah Magazine, and has authored five books.

The Bottom Line

Entrepreneurial ventures can offer huge financial gains, but require dedication, time, energy, the vision to succeed, and the courage to fail. Serial entrepreneurs work their way from one business to another, not merely sitting back and reaping the rewards of their past successes, but banking on their experience to start new ventures. Many of them have established themselves in a diversified set of businesses, and their successes, as well as their failures, provide important lessons for aspiring entrepreneurs.