What Is a Serial Entrepreneur, and How You Can Become One

If you think starting or growing a business is difficult, imagine doing it while also attending to multiple ventures simultaneously. This is precisely what serial entrepreneurs do. 

It’s not easy, but if 96% of self-employed workers have no desire to go back to a “regular” job, we can safely assume that being an entrepreneur is a rewarding profession.

If you’re considering it, this article will hopefully get you one step closer to understanding what it is and how to become a serial entrepreneur.

What Is a Serial Entrepreneur?

Let’s start with the basics and define it simply; a serial entrepreneur is anybody who has made it their profession to invest resources in multiple new businesses or ideas to take them to a stage where they can be sold for profit or operated without much interference. 

The term may get tossed around lightly, but becoming a true serial entrepreneur is not an easy feat. Serial entrepreneurs are calculated risk-takers who can spot opportunities and work as a jack of all trades, venturing into different industries and clearing obstacles for any business where they invest.

Ultimately, serial entrepreneurs must identify challenges in societies (or businesses) and fill the gap between the identified challenge and the proposed solution.

What Is the Difference Between a Traditional Entrepreneur and A Serial Entrepreneur?

More often than not, your typical entrepreneurs will have just one idea which they will devote their career to and ride out their life with. On the other hand, a serial entrepreneur will not stick around a business long enough before another idea or venture gets their attention.

For fear of neglecting one over the other, average entrepreneurs would hold back from starting new businesses while having one that “keeps the food on the table.” Serial entrepreneurs tend to lack that emotional attachment towards any particular project and instead have a passion for the mere process of starting or improving a business.

Any entrepreneur must have enough passion for being willing to do whatever it takes to see their vision succeed. Serial entrepreneurs’ only difference is that they don’t like to stay still for long and are always looking for new problems to solve or markets to tap.

What Are Examples of Serial Entrepreneurs?

You probably won’t find a decent article on serial entrepreneurs that doesn’t mention Sir Richard Branson. The Virgin Group mogul started his first company in his 20’s and continues to add to his diverse portfolio of 60+ companies in his 70’s.  The Virgin conglomerate Sir Branson founded has incorporated airlines, wireless communication providers, radio stations, hotels, health clubs, financial services businesses, nightclubs, renewable technologies, a Formula One team, and even a space tourism company.

Warren Buffet, Wayne Huizenga, Oprah Winfrey, and Donald Trump are some other big-names that make up the list of successful serial entrepreneur examples. The latest famous name to earn a spot on the list; Elon Musk, who started out in the software industry (Paypal) and has since then successfully migrated towards different sectors, including the automobile industry (Tesla), renewable energy (SolarCity), artificial intelligence (Neuralink), tunnel construction (The Boring Company) and even space (SpaceX).

What Are the Characteristics of A Serial Entrepreneur?

It is not easy to outline serial entrepreneurs’ character traits; they don’t need to have a particular kind of personality and could very well be different in approaching their ventures. However, some attributes seem to be recurring in the nature of serial entrepreneurs: 

• They are highly-motivated self-starters determined to see their visions through.

• They participate in business conventions and stay up to date on industry trends.
• They learn from failure and leverage their experience to improve on their next venture.
• They favor flexibility five times more than the potential to make money.

Although gender and age are not determining factors when becoming a serial entrepreneur, studies show that new business owners in the U.S. are getting younger, with the typical age dropping from 38 to 34 years old since 2017.

How Do Serial Entrepreneurs Manage Multiple Businesses?

Perhaps the toughest thing about managing a business is getting momentum between staff and processes, which, on a day-to-day basis, can make the company profitable. Once this momentum starts, running the business becomes a much more stable and repetitive operation that, if done right, needs little to no intervention from the founder or investor to produce dividends.

At this point, serial entrepreneurs will look towards new projects where they could create momentum and repeat the cycle, gaining experience and hopefully new revenue streams with every repetition.

To manage a second business, serial entrepreneurs generally have two main options; they can either hire staff to run the first one, receive dividends as shareholders and participate in the board of directors or sell the business for a substantial profit, moving on to the next project. Either way, only when serial entrepreneurs manage to solidify a team with a clear mission, a repeatable sales strategy, and a sizable market to tackle can they think of making any such decision.

Are Serial Entrepreneurs More Successful?

It depends on how you measure success. Studies carried out at the National Bureau of Economic Research (NBER) aimed to understand whether skill played any part in serial entrepreneurs’ success. It logically concluded that “successful serial entrepreneurs are more likely to replicate the success of their past companies.”

Successful serial entrepreneurs can add new income streams as they manage to establish profitable businesses, making their earnings (and therefore available resources for new investments) continually grow. One of their projects could occasionally be sold at a high premium for windfall gains or generate liquidity to pursue other ventures.

An article on TechCrunch back in 2013 concluded that “Nearly 80% of unicorns had at least one co-founder who had previously founded a company of some sort.” Another one in the Journal of Corporate Finance found that “repeat entrepreneurs get funded sooner, with less dilution and at higher valuations regardless of the success of their previous company’s performance.”

Evidence suggests that serial entrepreneurs can continually improve themselves to succeed better and bigger at each new venture by learning from their success and failure. Among small business owners, serial entrepreneurs tend to be more successful, but the question about which is more successful overall would have to be answered on a case-by-case analysis.

How Do You Become a Serial Entrepreneur?

There has never been a better time to become a serial entrepreneur. Traditionally difficult obstacles like access to capital, costly legal/accounting services, and staffing challenges can now be easily solved online. The U.S. offers the best environment to cultivate entrepreneurs; people need only the desire and an internet connection to get started on their entrepreneurial journey. Independently of how many projects you wish to pursue, there are several things you can do to improve your odds of truly evolving and being able to call yourself a serial entrepreneur:

• Inspire. Whomever you talk to should feel the passion you have for your projects.
• Develop your ideas. Whether intricate or not, you should be able to explain them easily.
• Research. Get to know the industry, its customers, players, products, and services.
• Outsource. Hire attorneys, accountants, employees, and other professional services.
• Engage. Attend industry-leading entrepreneurial-focused trade shows and conventions.
• Create a business plan. Have specifics you can show for every project you manage.
• Network. Meet as many people as you can and learn how to leverage connections.
• Close cycles. Strive to finish ventures you start and avoid getting caught in mediocrity.

In the end, serial entrepreneurs are masters of turning experiences into ideas for improvement and coordinating teams to build those ideas. If you are genuinely interested and committed to your idea, then there is nothing stopping you from becoming an entrepreneur but yourself.

What Are Some Tips for Serial Entrepreneurs?

Communication, problem-solving, and time management are the top three skills business owners think you need to be successful. Nevertheless, it will always prove beneficial for any individual to learn from other’s experiences to avoid making mistakes others made. These are some of the tips that you could learn by experience but would cost you much less if you learn them from here:

• Delegate; if you’re reluctant to let go of the steering wheel, you’ll always have to drive!
• Raise capital; know how to talk to investors, venture capitalists, and banks for funding.
• Scale; find ways of reinvesting in your businesses so they can keep growing naturally.
• Don’t give up; maintain a “if that didn’t work, how can we make it work?” mindset.

What Are the Pros and Cons of Serial Entrepreneurs?

Becoming a serial entrepreneur, like everything in life, is a matter of pros and cons. While any serial entrepreneur who manages to achieve success in multiple businesses is usually admired by the public and other fellow entrepreneurs, getting to that stage is not guaranteed. The process could leave you in a worse place than when you started. 

Consider these pros and cons before taking the plunge, and you’ll be more prepared to handle them if and when they come.

Pros

• Achieving a successful business will yield passive income to help fund future ventures.
• Find better funding as VCs trust the value that experienced startup founders bring.
• Do new things, try new ideas, and experiment without jeopardizing other businesses.

Cons

• Not all projects will work, especially as you try new things which you still don’t master. 
• You may miss out on great wealth by a business that you sold or cashed out too soon.
• Having multiple projects may lead you to focus on some while leaving others to fail.

Taking the plunge into entrepreneurship can be scary, especially considering that, in real-life, more will fail than those who will succeed. The rewards far outweigh the risks, though, but it’s up to everyone to make a responsible self-analysis to determine if you have the drive and resilience to go down a path that many fear. Some who have already walked the way of serial entrepreneurs are now reaping the benefits they once sowed by not conforming to a temporal state of success and rather exchanging it for a life of continued creation and entrepreneurship.