April 28, 2023
4 Examples of Serial Entrepreneurs
Examples of Serial Entrepreneurs Now that we have highlighted some distinctive characteristics of multiple business founders, let’s look at a few examples of notable individuals who have successfully launched numerous businesses.
Examples of Serial Entrepreneurs
Now that we have highlighted some distinctive characteristics of multiple business founders, let’s look at a few examples of notable individuals who have successfully launched numerous businesses.
1. Sir Richard Branson
ISTANBUL, TURKEY – NOVEMBER 17: Famous English business magnate Sir Richard Branson on November 17, 2007, in Istanbul, Turkey. He is the founder of Virgin Group, which comprises more than 400 companies. Source: Shutterstock.
British entrepreneur Sir Richard Branson is perhaps the quintessential poster child for serial entrepreneurs all over the world. His Virgin brand has been slapped on at least 200 companies ranging from record studios, rail and air travel, broadcasting, telecommunications to print and clothing. He launched his first business, a student magazine company, back in the 1970s in his early 20s.
It’s worth noting that even with a recognizable household brand such as Virgin, Branson still manages to launch unsuccessful businesses. It is the price of entrepreneurship. Several duds have come out of the Virgin brand, most of which have been folded, while a few others have been sold off.
2. Elon Musk
LOS ANGELES – FEB 26: Elon Musk at the 2017 Vanity Fair Oscar Party at the Wallis Annenberg Center on February 26, 2017 in Beverly Hills, CA. Source: Shutterstock.
As of September 2021, Forbes reports Musk’s net worth to be more than $200 billion, making him the wealthiest person in the world. A large portion of his wealth comes from his Tesla shares and the rest from his stake in the space exploration company SpaceX, which he also co-founded.
Musk first started his entrepreneurial pursuits through the software development company Zip2, which he co-founded with his brother Kimbal and Greg Kouri in 1995. He then co-founded an online financial services company called X.com which later merged with PayPal and saw Musk take up the role of CEO. After selling PayPal to eBay at the turn of the century, Musk moved on to the electric car company Tesla, co-founded in July 2003 by Martin Eberhard and Marc Tarpenning. Musk joined the company in 2004, initially as an investor, but soon took up an active role in its management as the CEO in 2008.
Other ventures that have been associated with Musk include SolarCity/Tesla Energy, Neuralink, The Boring Company, and OpenAI, a not-for-profit artificial intelligence (AI) research company.
3. Andreas von Bechtolsheim
Andreas Bechtolsheim at Stanford holding a lecture on “The Process of Innovation” as part of the Stanford Engineering Hero Lecture series. Source: Wikipedia.
Andy Bechtolsheim is a German national who co-founded the American technology company Sun Microsystems in 1982. He took up the role of the chief hardware designer and became the company’s first employee.
In 1995, Bechtolsheim left Sun Microsystems to create Granite Systems, a high-speed network switches manufacturer. He sold the company a year later to Cisco Systems for $220 million and joined Cisco as the vice president and general manager of the Gigabit Systems Business Unit.
Bechtolsheim stayed with Cisco through 2003 when he left to lead Kealia, Inc., co-founded in 2001 with Stanford Professor David Cheriton. Sun Microsystems later acquired Kealia in 2004 in a deal that saw Andy return to his first brainchild to serve as senior vice president and chief architect.
In 2008, Bechtolsheim again left Sun Microsystems for Arista Networks, where he took up the roles of Chairman and Chief Development Officer. Arista is a high-speed networking company he co-founded in 2005 for the second time with Cheriton.
4. Harry Wayne Huizenga
Blockbuster founder Wayne Huizenga has died in 2018. He was the only entrepreneur to create three different Fortune 500 companies during his career – Blockbuster Video, Waste Management, and AutoNation. Source: CNN Business YouTube.
Last but not least in our shortlist of notable serial entrepreneurs is the late American business tycoon Wayne Huizenga. Mr. Wayne had three multi-billion dollar companies to his name and several others with considerable market share.
The first of his companies was Waste Management, Inc., a Fortune 500 garbage collection company he created in 1968. It’s worth noting that Wayne hailed from a family of garbage collectors who made this business a natural introduction to the world of entrepreneurship for him.
Next came the launch of the movie-rental chain Blockbuster Video which he launched in 1987 after acquiring a few video stores. Blockbuster Video became the dominant movie-rental chain in the United States only seven years later.
Wayne then followed the Blockbuster Video success with the launch of AutoNation in 1996. AutoNation is an automotive dealer that also grew to become a Fortune 500 company and one of the largest dealers in the country.
Pros and Cons of Serial Entrepreneurship
It is true that there are many benefits to starting on the serial entrepreneurial route, but there are also certain drawbacks that should be taken into consideration. We’ll start with the positives, which include all of the good outcomes that have resulted from the pursuit of numerous successful business ventures.
Pros
- Wealth and respect – the most significant benefit to running multiple businesses or launching one successful venture after another is financial independence. Companies ideally bring profits, and the more you launch, the higher the chances of achieving financial goals. Respect and admiration are a natural byproduct of this process.
- Knowledge and skills-building – after launching multiple businesses, some of which fail and others succeed, the serial entrepreneur will inevitably learn several lessons. The more they keep repeating the process, the more they know and the better they become at launching subsequent businesses.
- Networking – the whole process of creating a new venture from conception to realization involves several stages, and it’s common for business owners to interact with other companies and people to try and solve problems. These interactions often lead to long-term professional and personal relationships that could prove invaluable to the serial entrepreneur.
- Innovations – the world is full of problems that need to be solved, and serial entrepreneurs do just that. Sometimes they come up with rehashed solutions implemented differently, but sometimes they introduce paradigm-shifting innovations that are crucial to the survival of the human race.
Cons
- Sharing limited resources – splitting critical resources such as finances and the entrepreneur’s attention when launching multiple businesses may be an advantageous thing as it aids diversification. However, the business founder has to contend with potentially lower returns due to investing less resources to each venture as opposed to picking a favorite and going all in.
- Common associations – this point works both ways. If the entrepreneur builds a solid reputation for their prior businesses, any subsequent venture they launch gets to inherit that positive association. The reverse is also true whereby if the founder is involved in a scandalous event, their lousy reputation rubs off on their current and potentially future ventures.


