Serial Entrepreneur

Updated on March 20, 2024
Article byAnkush Jain
Edited byAnkush Jain
Reviewed byDheeraj Vaidya, CFA, FRM

Serial Entrepreneur Meaning

A serial entrepreneur is an individual who owns or establishes new businesses. They own numerous businesses over a period but run only one business simultaneously as they step back from an existing business before starting another. The businesses can be from the same industry or spread across multiple industries.

Serial Entrepreneur

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They are constantly looking for a product or service that can simplify a daily activity or develop an entirely new, hassle-free solution to an existing operation. They either manage all their active businesses or hire managers who take care of the daily operations while they can oversee or supervise them regularly.

Key Takeaways

  • Serial entrepreneurs start and manage multiple businesses during the lifespan of their careers. However, they usually step back or sell the venture before commencing their journey toward the next venture.
  • They are exposed to far more risk than their counterparts, as uncertainty looms over them way more often than any other entrepreneur.
  • The new businesses they acquire or start can be within the same domain as their initial venture, or they can move towards a different niche altogether.
  • Elon Musk, Jeff Bezos, Oprah Winfrey, Gary Vee, and Sir Richard Branson are some of our most famous serial entrepreneurs.

Serial Entrepreneur Explained

Serial entrepreneurs are looking for new businesses and ideas even though they already have a venture. The difference between these types of entrepreneurs and other closely linked ones is they sell their initial or original business and acquire, establish, or inherit other businesses in the future. They are visionaries with a “big picture” painted in their minds, enabling them to strive for more despite being extremely successful.

A question that most often arises is- What would the size of a serial entrepreneur salary be? Well, the most successful ones believe that money is a by-product of providing an ideal product or service. Hence, they focus on their product or service more than profit-making.

Of course, being profitable and scalable is something any entrepreneur would want for their businesses. Still, profits are apparent if the product or service is such that the consumers derive value from it.

They are also highly aware and updated on the happenings in the business world. They ensure to stay on top of the trends and innovations to clinch every opportunity that comes their way.

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Serial entrepreneurs are a breed of innovators that create something out of nothing. They can mold products or services in a manner that most individuals in the business world cannot. However, there are a set of traits that distinguish them from any of their counterparts. Let us discuss a few of them below:

#1 – Visionary

Serial entrepreneurs often end up creating products or service way ahead of their time. They are forward-looking and draft a blueprint for a long-term timeframe. This ability to visualize the organization’s growth comes from sheer passion, and their natural ability to manage, create, and re-create comes in handy.

#2 – Leadership Skills

For any entrepreneur, ensuring their workforce remains motivated and strives towards improving their professional lives and the organization’s plans is critical. They believe in leading the way toward the venture’s long-term goals. They can manage, motivate, and uplift multiple groups within the organization with flair and ease.

#3 – Quick Learner

The business world advances at a rapid pace, and the trends keep changing frequently. So a group of researchers conducted a serial entrepreneur analysis, which found that they can learn new ways of operation, planning, and managing compared to their counterparts.

#4 – Risk appetite

Since they keep moving from one business to another, often into different domains, they are under constant risk of uncertainty of the business being profitable and scalable. Yet, despite bearing significantly high risk than any other type of entrepreneur, they remain resilient toward their vision.

#5 – Facing Failures

The shift from one venture to another is not always as smooth and flowery as it looks at the outset. These entrepreneurs often face failure in their ventures. However, the trait that differentiates them from anybody else in the business world is that they face failures head-on and learn from them to improve the next venture.

#6 – Multitasking

Managing a new venture is a task that involves holding a juggling act of the highest degree. These master jugglers oversee everything from procurement to production, sales, marketing, and management without having to handhold across departments.


Entrepreneurs account for 16% of the United States adult workforce, approximately 31 million individuals. Serial entrepreneurs are a fragment of this section of the workforce. Let us understand the difference with the help of the examples below:

Example #1

Samuel is a passionate individual who has a natural flair for selling things. He started his first business at 12, re-selling his previous year’s books online. He soon got his friends and neighbors to sell their used books to him at a concessional price. By the time he was due for college, he had sold off his business to ABC Investors, a big firm, and moved on.

After a couple of months at college, he learned that the students found it challenging to find snacks while working at night. So he decided to invest the amount he got from selling his initial business into installing vending machines around areas densely populated with students.

The idea quickly became popular, and he sold the business off to a local businessman at the end of his tenure at college. He moved on to manufacturing healthy snacks as he had noticed that unhealthy ones were causing long-term health issues.

Example #2

The talk-show host and philanthropist Oprah Winfrey, popular for her show, “The Oprah Winfrey Show,” which aired for two and a half decades, is a serial entrepreneur people across sections of society look up to for inspiration.

She set up Harpo Productions Inc., which bagged the rights to her show. The venture was her first stint as an entrepreneur. She went on to develop as a founder and co-founder in ventures like OWN (Oprah Winfrey Network) and Oxygen and has multiple books to her credit.

Difference Between Serial Entrepreneur And Portfolio Entrepreneur

Entrepreneurs, as a segment of society, must be classified into more than one homogeneous group. Even within types of entrepreneurship, each one is different from the others depending on their styles, business models, and other factors. They are a heterogeneous breed of individuals.

Let us understand the difference between two of the most looked up to types of entrepreneurship- serial entrepreneurs and portfolio entrepreneurs. Even though they run multiple businesses simultaneously, their fundamentals have few differences. Let us take a look at a few of the differences:

Serial Entrepreneur

  • The serial entrepreneur business model is such that they start multiple businesses over an extended period.
  • They run or manage a particular business and sell it or step back from crucial positions before moving on to the next business.
  • The businesses may be in the same domain or across different industries.
  • They bear significantly higher risks than their counterparts as the risk of uncertainty is crucially high in their operations.
  • An entrepreneur of this nature builds a business to an extent where it is self-sufficient and then moves on to a different idea or an enterprise to build from scratch.
  • Their nature of operating comes from curiosity and passion rather than from a monetary viewpoint.

Portfolio Entrepreneur

  • Portfolio entrepreneurs retain their original or initial business while accumulating other businesses through acquisition, inheritance, or establishing them. Then, they run these businesses parallelly.
  • They are an isoform of habitual entrepreneurs.
  • Also, they run numerous businesses simultaneously.
  • They are significantly more experienced than novice entrepreneurs.
  • They hedge their risks across businesses but still bear notably higher risks than their counterparts.
  • The monetary motivation is high during the initial stages of their careers. However, financial motivation is almost nonexistent with time, while satisfaction levels are high.

Serial Entrepreneur vs Entrepreneur

BasisSerial EntrepreneurEntrepreneur
Differentiating TraitSerial entrepreneurs run or manage multiple businesses across their lifetimes but usually only one at a time.A typical entrepreneur comes up with a single idea and spends most of their career lifespan building and upscaling it.
Risk FactorRisk exposure is high as they keep moving from company to company and usually have to build the new business from a nascent stage.There is a potential risk of the idea or the business failing to keep up with the market. However, the risks are a fragment in comparison to that of a serial entrepreneur.
DomainsExperienced in multiple niches or different levels of the same domain.Develops experience and expertise in a particular domain.
ModelA serial entrepreneur business model involves a clear hierarchy where managers are hired to take over after the business reaches a particular stage.Initially, an entrepreneur tries to do everything independently to save costs. Eventually, work is delegated, but most decision-making depends on them.

Frequently Asked Questions (FAQs)

1. How is a serial entrepreneur different than a social entrepreneur?

While serial entrepreneurs commence and move on to multiple businesses across years with an economic factor in the mix of their goals, on the other hand, social entrepreneurs aim to improve the quality of services and goods to give back to society. Profits do not drive them. Instead, they work towards actively improving education, the environment, and social conditions.

2. Is Elon Musk a serial entrepreneur?

Yes, Elon Musk is one of the most famous entrepreneurs of this nature. He and his brother 1995 founded his first business, Zip2. Mr. Musk later sold it to Compaq Computer at $341 million. He later became the founder of companies like X.com, PayPal, Tesla, SpaceX, and The Boring Company. He also acquired the social media giant Twitter in 2022.

3. How do serial entrepreneurs work?

They are always on the lookout for the latest trends and needs of the market. Their natural flair to innovate the latest market requirement keeps them on top of the game. They are curiosity-driven individuals who find their driving force in solving the world’s problems.

This article has been a guide to Serial Entrepreneur and its meaning. Here, we explain its characteristics and examples and compare it with portfolio entrepreneurs. You may also find some useful articles here –

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