Ever wondered what it takes to launch multiple successful businesses? This guide will take you through all the steps to understand what a serial entrepreneur is, how they manage their businesses, their character traits, and the pros and cons of serial entrepreneurship.
Most people have great business ideas, but few ever muster the courage to follow through and try to actualize them into successful business ventures. These individuals are referred to as wantrepreneurs.
There’s a small percentage of individuals that will go ahead to assemble the resources necessary to start their businesses. These people are entrepreneurs, and they have distinct characteristics that distinguish them from wantrepreneurs. The most significant difference being their resolve and passion for wanting to see their ideas come to fruition.
It is an arduous journey, from the conception of an idea to the establishment of a thriving business. Some of the handful that tries it end up wiped out emotionally, physically, and financially due to their efforts. Ultimately, it is part of the risk involved in pursuing a dream.
Despite this highly likely undesirable outcome, the rewards from making it as an entrepreneur are almost always worth the effort. Business owners often have to slave away for several years with the hope of coming out at the top, but very few do.
It takes a different set of qualities to want to go over the whole process of launching a successful business over and over. That is where serial entrepreneurs differentiate themselves from entrepreneurs. While most business owners are content with a single idea, sticking with it over the long term, serial entrepreneurs never settle for one or two businesses.
In the next section, we’ll go through the characteristics that these types of entrepreneurs possess that enable them to establish many profitable businesses. Including how they manage to run several organizations – sometimes concurrently – and, most importantly, how you may develop these traits to launch those business ideas you’ve been sitting on for so long.
What is a Serial Entrepreneur?
As defined by the Oxford Dictionary, an entrepreneur is someone who “makes money by starting and running a business,” while the meaning of the word “serial” is “doing the same thing, in the same way, several times.”
In combination, these words mean someone who makes money by establishing and operating many successful businesses. The term ‘successful’ is important in this definition since establishing many businesses that fail does not constitute someone a serial entrepreneur.
The businesses don’t need to be started and run concurrently. Sometimes, the business owner might come up with a money-making idea, launch the business, scale it, and exit before moving on to the next venture. Either way, as long as someone has more than a couple of successful ventures to their name, they qualify to be referred to as serial entrepreneurs.
In addition, serial entrepreneurs are highly innovative people with special skills crucial to assembling all the ingredients necessary to start a business, implementing them, and scaling the venture to profitability. It may seem like a simple task to outsiders, but the mere fact that only a handful of these multiple-business founders are successful suggests that it may not be as easy as it looks.
How Do Serial Entrepreneurs Manage Multiple Businesses?
Two ways in which anyone can launch multiple businesses are individually or through a strategic partnership. For a serial entrepreneur, the latter often makes more sense since it’s improbable that one person can be well versed enough in multiple fields to identify opportunities.
Partners bring the necessary intimate knowledge and skills to thrive in a new field while also acting as co-managers for the enterprise, an arrangement that is advantageous to both parties. The serial entrepreneur would leverage the venture partners’ knowledge and experience in the new industry while they (partners) leverage the founder’s experience in launching businesses. Together, they can also manage the business and, optionally, serve the company as employees.
For the partners, combining efforts with the entrepreneur gives them access, not just to vast business connections and financial resources, they also get to tap into the entrepreneur’s skills of turning ideas into successful ventures. It is a symbiotic relationship.
For a small enterprise, a few partners may be enough to supply the required manpower to run the business. However, for medium to large companies, serial entrepreneurs have to employ people to which they will delegate their responsibilities. This way, they can get as much work done across their multiple businesses without sacrificing their efficiency.
Sometimes, business owners take a complete back seat to managing their ventures and delegating the daily management duties to the executive team members. A serial entrepreneur could retreat and take up only the role of a director, which is a less active role compared with managing the business, which frees up more of their time to dedicate to other ventures.
Characteristics of Serial Entrepreneurs
Entrepreneurs can be described using a particular set of qualities to which their success can be attributed. It takes a special kind of person to become a serial entrepreneur, and some of their characteristics are shared with single-business founders. These qualities include the following:
- Passion – it takes a lot of zeal and zest to attempt to overcome most of the challenges that an entrepreneur faces when launching and running a business. To want to do it over and over again, serial entrepreneurs need to be passionate about what they do, and this can be easily seen in how they talk about their ideas. Additionally, these individuals need to be passionate enough that it becomes infectious to everyone they engage with, which will help when seeking financial support and hiring a management team to run the business.
- Curiosity – there are several business opportunities around us all the time, but few people take an interest in exploring them. Serial entrepreneurs have a knack for asking questions and understanding why things are the way they are. Asking and exploring ideas leads to business opportunities. Their curiosity isn’t just limited to ideas but also people, which helps them identify the right people for the right roles.
- Charisma – serial entrepreneurs have a way of attracting the right people and getting them interested in their ideas. They are often radiating with confidence, ideas and are generally great people with which to associate. Given that they are curious and interested in other people and their environment, they get to discover ideas that they can share with those around them. People are always attracted to industrious people.
- Intelligence – it takes a certain kind of above-par intelligence to be able to handle all the tasks that a serial entrepreneur has to handle. We don’t mean genius levels of intelligence, but to be able to coordinate functions, manage people, raise funds, maintain social lives outside business is mentally challenging and can easily overwhelm the average business person.
- Emotional agility – Dr. Susan David, a psychologist at Harvard Medical School describes emotional agility as someone’s ability to “experience their thoughts and emotions and events in a way that doesn’t drive them in negative ways, but instead encourages them to reveal the best of themselves.” Serial entrepreneurs have to manage potentially negative emotional situations such as business failures, tough competition, rejections, not achieving goals, etc. They have to do this and maintain a positive attitude.
- Innovative – coupled with their curiosity, serial entrepreneurs are all about solving problems within their environments. Sometimes they come up with innovative solutions that lead to business ventures that are so unique that they lack direct competitors.
- Excellent time management – we’ve mentioned some of the tasks a typical multiple-business owner has to get done every single day. It will be nearly impossible to do these things without a disciplined mindset which includes effective time management skills.
These characteristics of a serial entrepreneur are not conclusive. As we mentioned before, they also share a lot of qualities with single-business entrepreneurs, including risk-taking, persistence, and being visionaries.
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
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
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 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
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
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 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.
- 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.
- 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.
Launching a business is challenging. Most people dream of doing it but never get around to actualizing those dreams. Starting multiple ventures could potentially lead to higher financial returns. There are drawbacks to serial entrepreneurship as well including huge financial risks, time, stress, etc., but generally, the rewards far outweigh the negatives.
Is serial entrepreneurship for you? Well, that depends on your goals and your character. If you find that you lack some or all the character traits we identified above that most serial entrepreneurs tend to possess, you can start cultivating them. A character can be built just like you can build a skill.
Start practicing and visualizing your ideas and how to make them happen, then get to work. You do not need to know everything right out of the gate. No single venture can be built exactly like the next, and this means that most of the things you need will become apparent as you work on your business.
FAQs on Serial Entrepreneurship
What is a serial entrepreneur?
A serial entrepreneur is someone who makes money by launching multiple businesses. They could run these businesses simultaneously, delegate the management duties or simply build it, scale it, and sell it before moving on to the next venture.
What is the difference between an entrepreneur and a serial entrepreneur?
In this context, an entrepreneur can be thought of as someone who has launched less than three businesses, while a serial entrepreneur has launched more than three. In some other contexts, the term entrepreneur can be used interchangeably to refer to a single or a multi-business founder.
What are the characteristics of a serial entrepreneur?
Most of the characteristics attributed to an entrepreneur can be used to describe a serial entrepreneur, but the latter has extra qualities that differentiate them. They include an extreme passion for what they do, heightened curiosity, great at networking, higher levels of intelligence, emotional agility, and efficient time management skills.
How do serial entrepreneurs manage multiple businesses?
Serial entrepreneurs are able to effectively manage several companies by leveraging the help of fellow partners and employees to oversee the daily activities while they focus on duties and responsibilities they are more comfortable handling. Those that are unable to juggle several businesses can instead opt to run one venture at a time whereby they launch it, scale it to profitability, sell it then move on to the next best thing.