The journey of any typical entrepreneur is a world of innovation, risk-taking, and unlimited opportunity to build new businesses. Within entrepreneurship, two distinct archetypes exist traditional and serial entrepreneurs.
Both types of entrepreneurs come up with business ideas and share a passion for building a business from the ground up, but what distinguishes one from the other are the strategies they use, the mindsets they hold, and the goals they are reaching for. Traditional entrepreneurs stick with only one business.
I will dive into the intriguing dichotomy between these two entrepreneurial approaches in business. I’ll describe what characteristics cause the serial entrepreneur to stand out from the more conventional entrepreneurs.
What is a Serial Entrepreneur?
A serial entrepreneur is an entrepreneur but differs in that this person starts multiple businesses and continues starting numerous entrepreneurial ventures throughout their career.
Serial entrepreneurs run more than just one single business. They run multiple businesses simultaneously and often build a new business venture to sell it. Once they sell it, they move on to the following new ideas.
These entrepreneurs are known for their ability to spot opportunities, take calculated risks, and manage multiple ventures simultaneously or sequentially. Some serial entrepreneurs are those who look for an existing company that is failing so they can turn it into a successful business.
They find excitement in not any particular business but the startup phase, and they love taking something from an idea to a functioning new business. They often have a combination of business acumen, innovation, and a high tolerance for uncertainty and challenges. These people take on more risk than a standard entrepreneur.
Characteristics of a Serial Entrepreneur
If you want to become a serial entrepreneur, sometimes called a portfolio entrepreneur, these are a few characteristics that many serial entrepreneurs possess:
Visionary
Serial entrepreneurs, and any typical entrepreneur, are forward-thinking and seem to have endless ideas they want to explore. They have an appetite for bringing order to the unorganized, feeling like there is always a better way to do something.
Risk Taker
Because starting a new venture is never lacking risk, serial entrepreneurs have to have a high-risk tolerance. All new ventures require the entrepreneur to take on some risk, and serial entrepreneurship requires even more risk.
This is no excuse to go in unthinkingly. Serial entrepreneurs likely don’t feel like they are taking on more than average risk because they do copious amounts of research, so they know what they’re in for and plan to overcome obstacles. Most serial entrepreneurs, if not all, have a highly skilled problem-solving attitude.
Leader
A serial entrepreneur must be a leader. They are visionaries who see things other people don’t, so they have to lead people in a way for their ideas to be adopted.
Even if it isn’t a new idea they come up with, when they start, it’s only them. They may be driven by wanting a billion-dollar business, or maybe they want to create one successful company after another because they have so many great ideas they want to share with the world.
Their ability to sell their vision and get others on board, such as early investors, business partners, and financial institutions, is how they succeed.
Master Delegator
Serial entrepreneurs have many projects going at once. Successful serial entrepreneurs achieve so much by delegating responsibilities to other people.
They rely on teams to get the needed work while focusing on organizing the teams effectively.
Restless
Many serial entrepreneurs start their first business and get hooked on the excitement of the startup phase. This is when they feel most valuable because they can make massive progress.
As a business grows, the progress slows down, and the feedback loop is longer. This causes serial entrepreneurs to become bored, seeking more excitement in a new venture. They don’t want to waste their time on one boring company.
Serial Entrepreneur Examples
Some of the most famous serial entrepreneurs are people you’ve heard of. These entrepreneurs tend to attract attention because they are always up to something.
Elon Musk
Elon Musk is currently the world’s most successful entrepreneur, coming in at #1 for the wealthiest person alive.
I’d say he’s one of the most successful serial entrepreneurs, having founded his first company, Zip2, in 1995 and since then has been behind many businesses.
Paypal, SpaceX, Tesla Motors, The Boring Company, and now, most recently, he took over Twitter and calls it X.
Sir Richard Branson
In 1970, 20-year-old Richard Branson founded his first company, a mail-order record business, Virgin Music. You likely know him for the Virgin Group, which is what that first business grew into as it accumulated more and more businesses over the years.
The Virgin Group is now a large conglomerate of 40 companies of products and services that are diversified from virgin music to virgin clothing and so much more. Different shareholders control each company.
Oprah Winfrey
Oprah Winfrey is one of the most successful women entrepreneurs in the world and a serial entrepreneur. In 1986, she founded Harpo Productions, Inc., which owns the rights to her well-known talk show, “The Oprah Winfrey Show.”
In addition, she co-founded the cable station Oxygen, publishes the O, Oprah Magazine, and has many successful books she’s authored.
Oprah Winfrey started from humble beginnings, started one venture, and grew an empire through many business ventures as a serial entrepreneur.
Steve Jobs
Jobs is best known for his hand in Apple, which he co-founded in 1976 with his friend Steve Wozniak. Both were college dropouts with a vision for changing how people viewed computers.
He went on to found his next venture, NeXT Computers and was also the chairman of Pixar.
Wayne Huizenga
Wayne Huizenga founded three multi-billion dollar companies: Waste Management, Inc., Blockbuster Video, and AutoNation. He also had a hand in establishing six NYSE-listed companies.
Huizenga also has an affinity for sports teams, having owned the Miami Dolphins, Florida Marlins, and Florida Panthers. He was the ultimate serial entrepreneur.
5 Tips on How to Become a Serial Entrepreneur
- Come up with an idea.
Creativity breeds more creativity. If you’re starting in a slump with one idea or less, do something known to ignite creativity. The one I like to use best is travel.
Many novice entrepreneurs started their entrepreneurial ventures from ideas they came up with while traveling.
- Evaluate the idea
You will need many ideas because it’s doubtful your one idea will be the idea that makes you millions. And your past successes do not guarantee all your ideas will be successful.
You must develop a set of criteria and established granite systems that an idea must meet to be successful for you. It would be best to run it through a series of tests before spending a dollar on it.
- Begin taking the steps to bring the idea to life.
If your idea meets all the criteria for a successful business, set a goal, create an action plan, and break down your action plan into a series of steps.
Serial entrepreneurs work through the steps individually, and it may take a few years, but they keep going. Serial entrepreneurs never quit.
- Use leverage in your favor.
You will need to use leverage in your favor. Leverage is technology, employees, business partners, financial institutions, and systems, to name a few.
You must get other people on board and delegate responsibilities to them.
- Find the right community.
Success isn’t impossible without the right community, but it is much more complicated. You want to surround yourself with others who allow you to work through problems verbally, understand your vision, and encourage what you’re working on.
Find people who also like to take on new ventures, find a business failing, and want to start new businesses.
Key Takeaways
- A serial entrepreneur takes on more risk than a typical entrepreneur.
- A serial entrepreneur is an entrepreneur who has an endless vision.
- Most serial entrepreneurs manage multiple businesses at one time
Recommended Articles
Famous Serial Entrepreneur Examples
Follow these links to read about some of the most famous serial entrepreneurs.
Serial Entrepreneur Successes
Follow these links to read about serial entrepreneur success stories.
Five seriously successful serial entrepreneurs
Entrepreneur Alternative: Solopreneur
If entrepreneurship isn’t something you’re interested take a glance at the option of solopreneurship.
