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Serial Entrepreneurship: What is it and How to Become One? 

By Venese | Last Updated: May 24, 2021

Becoming an entrepreneur is the most effective path to building an empire of wealth. Serial entrepreneurship will require you to expand your knowledge and time through multiple ventures for your companies to succeed. Managing these ventures and projects can be extremely time consuming – but well worth it. Some of the most successful business people have made fortunes from their companies that many people crave.

To help you steer clear of obstacles and reach your goals faster and easier, here are some tips to help you figure out exactly what is a serial entrepreneur, some effective tips to help you become a successful serial entrepreneur, and some examples of the most notable serial entrepreneurs. Let's get started! 

Serial Entrepreneur Meaning

A serial entrepreneur is an entrepreneur that has an idea, builds one business around that single idea and once it takes off, starts another business based on another unique idea. 

A serial entrepreneur is someone that is creative with fresh new ideas and growth strategies, bringing their ideas and concepts to live. Does this mean serial entrepreneurs never fail? Absolutely not. Serial entrepreneurs are able to learn from their failures and turn those lessons into a new business, with focus and strive. 

Once a business starts building momentum, the serial entrepreneur outsources and delegates the tasks to employees that will continue to run the business under the systems that the serial entrepreneur has created. 

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Serial entrepreneurs are different from traditional entrepreneurs because they are not only driven by money or interest, but they are driven by passion and enthusiasm. They build ideas and develop systems. Through their relationships, connections and resources, they are able to continuously build empires and grow them out of unique ideas. 

Serial entrepreneurship is no easy process – working as an entrepreneur is hard work so you shouldn't go into it lighthearted. Managing multiple businesses at once can be stressful and overwhelming for many entrepreneurs.

There are several characteristics that define serial entrepreneurs such as hard working, imaginary, creative, smart, and many more.

Related: How to Make Money Doing Nothing

Serial Entrepreneurship How to Become One

How to Become a Serial Entrepreneur? 

Let’s be honest here. Being an entrepreneur can be a difficult task, and being a serial entrepreneur means encountering challenges over and over again. 

If you want to become a serial entrepreneur, you have to first understand that it requires a lot of effort on your part. Understand that setting up successful businesses does not come easy. It requires hard work, strong relationships and the ability to recover through hiccups along the way.

There are a lot of challenges that you will likely run into, all kinds of changes you have to keep up with and pressure seems to be always weighing you down. Here are some tips to help you prepare yourself and set you up for success as a serial entrepreneur. 

Related: 31 Profitable Business Ideas for Anyone to Start in 2021

Gain Experience with New Businesses

Your first experience as an entrepreneur might not be the most successful. Starting a new business can require significant capital and equally as much hard work. The typical entrepreneur will often need to put in 50 or 60 hour work weeks to get their business off the ground. If you're managing multiple businesses this number can increase even more.

Before going all out and managing several businesses it's best to start one business that you can dedicate the time towards.

Stop Doubting Yourself 

Doubt is a big part of the entrepreneur mindset that you need to get over. It’s ok to have doubts every once in a while but don’t let those moments drag you down. If you don’t see results right away, if things aren’t going as smoothly as you hoped or you have been spending more time than what you expected on certain tasks, understand that it is normal.

If you make mistakes or realize something has gone wrong, and yes something will likely go wrong ever once a while, instead of putting yourself down and wondering if you should continue, take a second to reevaluate, think about what needs to be done, take a deep breath, correct the mistakes and continue. 

Focus on the Right Things 

It is easy to get distracted and keep yourself busy by throwing yourselves into countless meaningless tasks. Checking emails, making small adjustments to your website to “make it perfect” are just some of the many things that you might be doing. 

We all have the same amount of time every day so instead of spending time on the small things that don’t require your attention, focus on tasks and actions that can help you grow in your business journey. 

Successful serial entrepreneurs are capable of focusing on the tasks that matter most and provide the highest ROI for their time.

Be Passionate and Stay Motivated 

Commit wholeheartedly, and for the long haul. This doesn't necessarily mean putting down financial capital. Make an emotional and educated investment into whatever the business concept may be.

Researching your business idea is crucial to success. Is anybody else doing it? What's the usual market response to similar ideas?

Serial entrepreneurs need to be passionate about their business or you may run the risk of burnout. When starting a new business it can be easy to stay motivated. After a few months it might be more difficult to focus on your company.

Identify a Target Audience

No matter if you are starting a coaching business, an e-commerce store, a marketing agency or any other business, you need to identify your target audience. Who wants your product or service? Naturally, you'll need to be able to identify them. It's safe to say that a business without a target audience may not do very well!

When you determine your target audience upfront, you can focus on building a marketing plan around them.

Related: How to Start a Business as a Teen [Step by Step Guide]

Find Ways to Start Small

It's exciting to have big ideas for your business. But it's also wise to start small. Start researching and designing launch plans, financing, and other key elements to get it going, with plans for expanding as profits allow.

Some of today's biggest businesses started as tiny “hole-in-the-wall” operations. For example, Steve Jobs built computers in his garage. This may be the approach for you since it's your first entrepreneurship.

Your bank might be offering you impressive financing. But do you really need all that startup capital? Keep your head on and only take what you really need. The less debt you have at the onset, the easier it is to see profits.

Before commanding multiple ventures, consider starting a business that you can manage on your own. You don't need a perfect track record to become a serial entrepreneur.

Think Evolution

The businesses with the greatest success are the ones that constantly reinvent themselves. You'll need to have that eye of longevity in order to build a good business model.

Your business idea might be for bottled water today. But who says it can't evolve to other bottled beverages tomorrow? This is the kind of thought to put into your startup business.

Don’t be afraid to embrace the changes. Technology is constantly changing these days. Maybe you have been incredibly comfortable the way something is going, then suddenly changes happen. 

No one likes unpredictable things. Most of the time, changes take time to get used to and for you to adjust to. Adapt to these changes and welcome them, because most of the time, the changes are for the better. If the change isn’t for the better, pivot and make adjustments. There are always solutions, you just need to embrace them. 

Treat change like your good friend, not the enemy. This is what successful businesses have done. Entrepreneurship and technology work together. The faster you accept that fact, the better.

Stop Holding onto your Business so Tight

The difference between being an entrepreneur and a serial entrepreneur is about how tight you hold onto your business. If you are unable to let go and delegate, then you won’t be able to grow and neither will you be able to move to a new venture. 

You simply can’t do everything yourself. Allow other people to help you. Delegate tasks to employees, virtual assistants, designers, content creators. This can free up time so you can spend time growing your business with planning, networking and making connections.

Delegation, as hard as it could be, is the structure of business growth. Delegating can teach you how to let go of the work that’s not something you need to always be doing. Stop doing those repetitive tasks and anything that can be automated or handed over to others. Allow people that are great at these tasks to take over so you can concentrate on your most efficient activities and help to bring your business closer to your vision. 

Don’t be Afraid to Fail 

No one wants to fail. No one likes the idea of losing money, time or energy and being disappointed. But if you are scared of failures, then you will never leave your comfort zone and try something different. 

Most of the time, the most successful entrepreneurs are born out of bad circumstances, feeling terrified and anxious. Only through failing and learning will you learn, understand what to do and what not to do and succeed in reaching the goals and meeting your vision. 

When something doesn’t go the way you want it to, don’t freak out. Think about what went wrong, what you learnt and never make that mistake again. 

Examples of Serial Entrepreneurs

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Examples of Serial Entrepreneurs

Below are some of the most famous and influential serial entrepreneurs.

Oprah Winfrey

Oprah Winfrey is one of the most famous serial entrepreneurs with many different businesses. She started the Oprah Winfrey Show in 1988 and co founded then Oxygen television network.

Elon Musk

This serial entrepreneur is most notably the founder of the tech company Tesla and Space X. Elon Musk is known for his quirky attitude and hard work ethic. The companies he has built have become multi million and billion dollar ventures.

Warren Buffett

Warren Buffett is one of the classic entrepreneurs that has grown several businesses from his new ideas. His main company, Berkshire Hathaway is worth billions of dollars.

Mark Cuban

Mark Cuban is another famous serial entrepreneur who owns the Dallas Mavericks NBA team. Cuban originally started Broadcast.com before selling it to Yahoo for $5.7 billion in 1999.

Richard Branson

Richard Branson is one of the original serial entrepreneurs dating back to the 1970s. He founded the company Virgin Group which now owns over 200 companies with several investors.

Rod Drury

Rod Drury is one of the most successful serial entrepreneurs in the early 2000s. He established Xero and worked with Pacific Fiber.

Final Thoughts on Serial Entrepreneurship

At this point, you're probably already starting to feel excited and ready to get your serial entrepreneurship journey going! Getting your business idea off the ground is a challenging, but rewarding experience. 

Being an entrepreneur can mean spending hours, days, even weeks on end sitting in front of your computer, doing nothing but typing away on your keyword, trying to get another blog post out there, another social media post up and running, creating a campaign. It is a never-ending cycle for many serial entrepreneurs. 

As an entrepreneur, especially solopreneurs, you are your biggest fan. You need to cheer for yourself louder than anyone else. When doubts arrive, welcome them in, understand them and then send them on their way. 

Nobody dreams bigger dreams for you than you do! Live those dreams out and create the empire you always wanted. It's yours for the taking.

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Venese runs an events and marketing company in Tokyo, Japan. She has been an entrepreneur since she was 19, running all kinds of offline and online businesses. She is the host and face behind Your Entrepreneur Resources, where she helps entrepreneurs start, grow and scale their businesses, connecting them with the right mentors, resources and tools.