Top 10 Best Serial Entrepreneur Of All Time – 2021 Update

Most of us are accustomed to the term entrepreneur. But in case you do not know what is a serial entrepreneur is, let me define a serial entrepreneur for you. A serial entrepreneur is someone who has more than one business in their bucket. They start one business, and then if they fail, they start another one. Or, in some cases, they sell the existing business in a great deal and start another one. 

Top 10 Best Serial Entrepreneur Of All Time

Here are the top 10 entrepreneurs of all time. Who never fails to amaze us with their new innovative business ideas. Here are the serial entrepreneur examples.

1. Anthony Mongeluzo

At the age of 21, Anthony Mongeluzo had started his first professional company from his parent’s house and take a step towards being a serial entrepreneur. And that is Pro Computer Services. He also had other companies when he was a teenager.

He is also the CEO and President of an information technology firm, Marlton, N.J. After some time, PCS has gained regional as well as national recognition as one of the fastest-growing companies. With annual revenue of $25 and 25 employees, PCS has offices in four states. 

Companies:

• pilotLight studios.
• Pro Computer Services.
• Dynamic Telecom Solutions.

2. James Currier

At the age of 6, James Currier started his entrepreneur career as a worm seller, and now she is one of the best serial entrepreneur. When he was in the 8th grade, he opened a store in his school cafeteria. By the time he graduated from Princeton University, he already has 18 little ventures in his bucket. Jiff Inc., which is well known for making HIPAA-compliant mobile software for the medical industry, is lead by James Currier.

He is not only the lead investor here but also the Executive Chairperson. He has also founded Palo Alto-based Ooga Labs. It helps to develop e-commerce and mobile startups along with medical software. 

Companies:

• Tickle.
• Ooga Labs.
•  Jiff Inc.

3. Ellen Thompson

Ellen Thompson has experience in starting and selling companies for more than 20 years. In the year 1993, Thompson founded a skill-testing firm names Know It All. In 2000, Kenexa Corp. had bought more than 300,000 shares. After she founded another company named 4 Walls, she is now the CEO of the company.

This company is based near Philadelphia and helps the apartment owners to get customers via search engine marketing and social media. The list of serial entrepreneurs will be incomplete without this name. 

Companies:

• 4 Walls.
• Know It All.

4. Rod Drury

This New Zealander serial entrepreneur has a fascination with computer technology from his teenage age, and he has transformed this fascination into his career. He helped in founding the software company named Glazier Systems. In the year 1999, it was sold for around $7 million.

He was also the founder of AfterMail, which is an email intelligence concern. In 2006, the QSFT or Quest Software acquired AfterMail for $15 million. At present, Drury is the director of the New Zealand Stock Exchange, the director and founder of Pacific Fibre, and lastly, the Chief Executive Officer of an online accounting portal Xero. 

Companies:

• Pacific Fibre.
• AfterMail.
• Glazier Systems.

5. Janet Kraus

Janet Kraus is the senior lecturer of the Harvard Business School and has already started and sold 2 businesses. She is the co-founder of the concierge service company Circles. With her hard work, she developed the company with a revenue of $50 million. In the year 2007, she then sold Circles to Sodexo.

Just after that, she started leading Spire. This is a high-end social media business that is related to travel. In the year 2010, it was sold to Perfect Escapes. He is another serial entrepreneur who finds it fascinating to start new ventures. 

Companies:

• Spire.
• Circles.

6. Josh Kopelman

The managing director of First Round Capital, Josh Kopelman, is very fond of forming and investing in Internet companies. It has already been around two decades since he is doing this. In the year 1992, the Infonautics Corporation, which came to the public 1996.

At that time, he was attending the Wharton School at the University of Pennsylvania. Three years later, in 1999, he started Half.com, which is an online store for used music and books. But just after one year, it was acquired by eBay. He has also invested in several startups, like mint.com, StumbleUpon. 

Companies:

• TurnTide.
• Half.com.
• Infonautics.

7. Harpal Sandhu

Harpal Sandhu is the Chief Executive Officer and President of Integral Development Corporation. It is a  Sunnyvale, California based company of this serial entrepreneur. It was 1993 when he is the co-founder of this company. This organization claims to be the only multi-sided trading network that works for foreign exchanges.

Earlier, Sandhu was the president and founder of Infinity Financial Technology. In the year 1998, the software company named SunGard Data Systems had acquired Infinity Financial Technology. 

Companies:

• Integral Development Corporation.
• Infinity Financial technology.

8. Gerard Ferro

It has already been more than two decades since Gerard Ferro has been setting up and running technology and health businesses. He is also the co-founder and CEO of a prescription-discount business, Free For All, which is based in Marlton.

Gerer Ferro also cofounded a pharmacy benefits management concern SUNRx. He was also the chairperson and CEO of the organization. Under his leadership, this company was able to gather a revenue of $49 million in its first five years. During the late 1980s, he was also the co-founder and CEO of Simacre. 

Companies:

• SUNRx.
• Simcare.
• Free For All.

9. Oprah Winfrey

Oprah Winfrey is another shining star in the sky of serial entrepreneurs. When she was in high school, he started his career in this broadcasting industry. The media empire and her group of businesses across magazine publishing, radio, and television have made her a billionaire.

As per Forbes, her estimated net worth was $2.8 billion in 2018, and she is the wealthiest woman in show business. In 2011 she had launched OWN or Oprah Winfrey Network. The official website of OWN claims that 70% of homes in the United States have OWN. 

Companies:

• Oprah Winfrey Network.
• Harpo Productions.

10. Richard Branson

In 1970, when Sir Richard Branson was around 20 years old, he started a mail-order record business. After that, it was time for a record shop in London. Within a couple of years, he built a studio, where “Tubular Bells,” an instrumental by Mike Oldfield.

His Virgin Group now has around 200 companies in more than 30 different countries. Branson is also famous for promoting various social causes using celebrity power and his wealth. Being a prolific blogger, he also has written a book, which is published with the name “Screw Business as Usual.” 

Companies:

• Virgin group.

Conclusion

They are those entrepreneurs who have never failed to come up with new ideas in case one is failed or acquired by others. They have a bucket full of new and innovative ideas to lead and build a successful career path. They are inspirations for this generation’s entrepreneurs who are willing to make their own identity.