The Art of Being a Successful Serial Entrepreneur: Lessons From Industry Leaders

businessman raising his hands in front of commercial buildings
  • All ventures don’t need to be successful for someone to be a serial entrepreneur.
  • Serial entrepreneurs don’t have a limit to the number of businesses they must start.
  • One of the most famous serial entrepreneurs is Elon Musk.
  • Over 40% of serial entrepreneurs build their first business over several years, and less than 1% start more than 10 companies in their lives.

Entrepreneurship is an activity that involves turning ideas into businesses, and the people who create the businesses are called entrepreneurs. While you can come across several kinds of entrepreneurs, one group that stands out is serial entrepreneurs.

If you wonder what the serial entrepreneur meaning is, know that the name refers to every entrepreneur that turns multiple opportunities into ventures that are commercially viable but carry certain risks with them. Not all ventures need to be successful for an entrepreneur to be considered a serial entrepreneur. Plus, there is no limit to the number of businesses they must start to be considered serial.

Serial entrepreneurs are extremely important in society as they help fill the market gaps, whether in education, science, law or business.

In today’s article, we will discuss the traits of successful serial entrepreneurs and the advantages and disadvantages of this type of entrepreneurship. We’ll also go through some case studies and strategies you can use to become a successful serial entrepreneur. So, without further ado, let’s dive right into the topic!

Traits of Successful Serial Entrepreneurs

It is not enough to define serial entrepreneurship—one also needs to know the traits of successful serial entrepreneurs to understand how to become one. A serial entrepreneur should be passionate, persistent, creative, resourceful, a leader, a great communicator and willing to take risks.

Let’s explore these traits more to help you learn why having them is essential to becoming a great serial entrepreneur.

Passion and Persistence

Being passionate about something can prove helpful when starting a business. It ensures that you will not get bored with the company or discouraged if you encounter difficulties. Starting a business is never easy, whether you are starting your first or tenth.

You must remember to be persistent and keep the end goal in mind. As long as you are willing to work to get the desired results, there’s no doubt that you can become a successful serial entrepreneur sooner or later.

Strong Leadership and Communication Skills

All serial entrepreneurs can benefit from excellent communication skills, as they constantly communicate with employees, investors, customers or other companies. Being presentable and eloquent is always a plus and can make entrepreneurs look more confident in their businesses and ideas.

Furthermore, entrepreneurs must present themselves as strong leaders who know what they are doing. At the same time, it helps to be a team player with your employees, as you should always let them know you are there to help and guide them.

Creativity and Resourcefulness

When creating a business, any serial entrepreneur needs to have a clear vision and a creative solution to make that business successful. Even if they encounter problems, they must use their creativity to move past the difficulties and continue their journey to building a successful business. That is also where resourcefulness as a trait can come in handy since it can help you quickly come up with creative solutions to solve all problems.

Willingness to Take Risks

The serial entrepreneurship definition says that entrepreneurs with multiple ventures take more than normal risks. So, an entrepreneur must be prepared and willing to take risks in hopes of creating a successful business. Without taking risks, there is no moving forward in business.

Case Study: Elon Musk

Elon Musk is one of the most famous serial entrepreneurs of our time. He has had several successful businesses since opening his first-ever company in 1995—Zip2, which was eventually acquired by another company.

With the funds he got from selling his first company, Musk started, which later became PayPal. SpaceX and Tesla Motor followed, with the latter currently considered one of the most valuable brands in the world.

Tesla Company

The Boring Company is one of Musk’s latest endeavors, established in 2016 and focused on tunnel and infrastructure construction, showing that Musk was interested in developing and starting companies in many different fields. Recently, he also acquired Twitter after becoming the company’s largest shareholder.

Learning From Industry Leaders: Case Studies

Aside from Elon Musk, there have been a lot of other successful entrepreneurs who have started some of the biggest companies we all know. From the founder of Apple to the beginning of Amazon, below are a few other serial entrepreneurs and their successful ventures.

Richard Branson: Virgin Group

Richard Branson is a British entrepreneur who started the Virgin Group when he was only 20. His initial idea was to create a company for mail orders that would help him distribute records. No one ever thought that the small company would eventually turn into a global brand made out of more than 40 companies and additional 200 subsidiaries.

Over the years, Branson also created Virgin airline, rail group, radio, mobile network, record label, etc. He has built on the brand ever since the first company turned out to be a success, which is the epitome of what is a serial entrepreneur.

Apple Company Logo

Steve Jobs: Apple

While Virgin Group might not be a famous company among younger generations, Apple surely is. Apple is one of the largest technology companies, thanks to its iconic iPhone, iPad, Mac and other designs. But it all started with Steve Jobs and his unique ideas.

Steve Jobs was a visionary before anything else. He co-founded Apple and helped it grow before being pushed out of it in 1985 because his bold ideas were deemed “too much.” He went on to start two more successful businesses, NeXT computers and Pixar, only to be brought back to Apple in 1997, from where he helped the company reach new heights.

Oprah Winfrey: OWN Network

Oprah Winfrey has a very inspirational story as she is an entirely self-made entrepreneur, philanthropist, and media leader. She is best known for her talk show “The Oprah Winfrey Show,” but few people know that the show aired on her own media production company.

In fact, Winfrey has started a few production companies, a cable station and a magazine. Furthermore, she has published several books which have attracted global attention. But it all began with one TV show and the idea to try and build something more significant.

Amazon company

Jeff Bezos: Amazon

Jeff Bezos is another successful entrepreneur who started his first company from an actual garage. At the time, he had gathered some funds from relatives who wanted to invest and looked at the market to see what would be a good investment opportunity for him. He settled his mind on an online bookstore, which is how Amazon was born.

From the simple idea of selling books online, Bezos created an online e-commerce business that offered more than a million titles within a year of starting. The greatness of his entrepreneurship can be seen in his ability to adapt and grow, turning his bookstore into a global retailer that today sells everything!

Bezos himself has said, “Success can come through iteration: invent, launch, reinvent, relaunch, start over, rinse, repeat, again and again.” This is a lesson all aspiring serial entrepreneurs should keep in mind.

Arianna Huffington: HuffPost

HuffPost is one of the first alternative news platforms ever created. Ariana Huffington got the idea for this platform after being surrounded by journalists for years. Her father used to be a journalist, but she also had the opportunity to closely observe Bernard Levin’s work, one of the most famous journalists.

If you look at Huffington’s story, you will notice that after her first successful business, she had quite a few unsuccessful ideas that failed to generate enough interest among readers. However, that did not stop her. She eventually started Thrive Global, a consulting firm entirely different from the news platform she once participated in.

Statistics and Studies on Serial Entrepreneurship

As you can see, most world-famous entrepreneurs did not stop after one successful business. They started a few more companies, many of which failed, but some became global successes.

If you are still on your first business but wish to become a serial entrepreneur, don’t worry. According to a study by Kauffman, more than 40% of entrepreneurs spend years working or running their first business, and less than 1% start up to 10 companies in their lives.

If you want to start your second business and become a serial entrepreneur, we recommend that you first equip yourself with market knowledge, what gap you can help fill, what skills you need for that and how much time and money you need to invest. Only after that can you start to develop a business that has a chance to become successful.

Advantages and Challenges of Serial Entrepreneurship

Now that you know some of the traits of successful entrepreneurs and have read through our serial entrepreneur examples, we will also tell you about the advantages and challenges of this activity. This way, you’ll understand more about what is a serial entrepreneur.


  • Diversification of Portfolio – Few serial entrepreneurs start multiple businesses within the same field or market. They often change things up, leading them to form a diverse portfolio. A well-developed, diverse portfolio can help entrepreneurs persuade investors to invest in them so that they can continue building successful businesses.
  • Building Networks and Connections – When working as an entrepreneur, you will inevitably have to meet people within your target markets, potential clients, employees, collaborators, etc. These connections can provide industry insight, helpful feedback or advice on succeeding in your work.
  • Gaining Multiple Skillsets – As mentioned above, entrepreneurs focus on more than one market or field. When working on their many businesses, they develop various skill sets that help them better understand the market and people’s needs, which can, in turn, help them come up with ideas about possible future businesses.


  • Balancing Multiple Ventures – Serial entrepreneurs who don’t want to turn over their businesses to other people often need help balancing their ventures. So, it is advisable to have a team of people that can take at least some of the work away so you can be free to focus on your next venture.
  • Maintaining Focus and Drive – Entrepreneurs are filled with ideas and often searching for their next big break. While being creative is good, it can become problematic if the entrepreneur has difficulties focusing on one idea at a time. It can also mean that the entrepreneur gets bored quickly and loses their drive, which causes them to move swiftly from one idea to another.
  • Risk of Overextending Resources – Sometimes, serial entrepreneurs can get too attached to a business, overextending resources even if they know the venture is bound to fail. The risk of overextending resources, especially money, is relatively high with serial entrepreneurship, so you should always set limits for yourself and stick to them.

Strategies for Success

If your goal is to become a serial entrepreneur, there are a few strategies you can employ to become as successful as possible from the very beginning. Here are a few of the techniques we recommend:

  • Setting Clear Goals and Priorities – To give yourself the best chance to create a successful business, establish clear goals and priorities that will help you focus only on what is important. Look at the market, find a gap you think you can work on, and set a goal to fill it to the best of your abilities.
  • Fostering a Supportive Network – Surround yourself with people who can support and help you and who can give you constructive feedback that you can use to better your ideas or companies.
  • Adapting to Change and Failure – Considering that the market can often change, ensure you follow the trends and adjust accordingly to give yourself the best chance to succeed. Also, be prepared to fail sometimes, as all businesses have risks.
  • Maintaining a Strong Work-Life Balance – Dedicating yourself to your business too much can be problematic for your personal life. So, even if you are working on an idea you are incredibly passionate about, try to balance your work and personal life as much as possible so you don’t burn out.


Successful serial entrepreneurs have at least two companies they have started simultaneously or one after the other. They are essential for economic growth because they constantly open new companies and create new job positions.

If you want to become a successful serial entrepreneur, follow the traits of successful entrepreneurs and use some of the strategies listed in this guide. Don’t hesitate to make the first move toward starting your new venture!

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