In Career Last updated:
Share on:
Jira Software is the #1 project management tool used by agile teams to plan, track, release, and support great software.

Are you curious about the success secrets of serial entrepreneurs like Elon Musk, Richard Branson, and the late Steve Jobs? This article reveals the secrets of successful serial entrepreneurship!

We’re effectively living the ear of entrepreneurship! It’s evident from these recent facts published by ThinkImpact that globally, there are 582 million entrepreneurs, of which 31 million of them are in the United States.

However, you’ll often see that most of these entrepreneurs have converted their ideas and creativities into one venture and constantly engage with the entity to grow it. 

Some entrepreneurs don’t settle with one startup. They set up one venture, see it become successful or fail, and start another startup, then a new one, and the number of startups founded by them keeps on growing.

Want to become such a serial entrepreneur? Keep reading until the end to learn everything you need to know!    

What Is a Serial Entrepreneur?

A serial entrepreneur is a business founder who starts multiple businesses in their lifetime. They may hold the controlling position of all the ventures or hire CEOs to manage businesses. 

Some serial entrepreneurs set up many startups and sell those to interested buyers when these become profitable. Later, they reinvest the profit earned from selling previous businesses to kickstart more ventures.

Many of these founders also support other startups with money, mentorship, or by becoming a member of their board of directors. Successful business founders tend to become serial entrepreneurs because they find conceptualizing an idea into a profitable business thrilling. 

They’re also excited about product or service marketing at their early stages, setting up highly productive teams, and closing funding deals with top venture capitalist agencies. 

Also read: Startup Funding Stages: Seed, Series A, B, C, & D Explained

Characteristics of Serial Entrepreneurs

If you’ve got the following characteristics as a business founder, you’re highly likely to become a successful serial entrepreneur:

#1. Thinking Outside the Box

You’re a creative thinker and find solutions to a business problem from the most unorthodox perspectives that the general business people never think of. To start businesses one after another and see them grow, you don’t limit yourself to conventional ideas. You’re willing to take risks in exploring novel business approaches to set a trend that others want to follow.  

#2. Identifying Market Gaps

Finding the void of certain services or products in the market is a great way to set up new businesses that might become profitable, too. You’ve got this knack for spotting opportunities in the market. You notice unmet needs of customers and businesses and niches that others might overlook. This skill allows you to create businesses that address these gaps and provide value to customers.

#3. Calculated vs. Uncalculated Risks

You’re not afraid of taking risks, but you’re also not reckless. You assess risks carefully, weighing potential rewards against potential losses. You make informed decisions, ensuring that risks are worth the potential benefits.

#4. Risk Management Strategies

As a serial entrepreneur, you’re prepared for unexpected challenges. You’ve got solid plans in place to mitigate risks and minimize negative impacts on your businesses. This proactive approach helps you navigate uncertainties effectively.

#5. Embracing Change

Probably, the constantly changing business world is one of the driving factors that transforms an entrepreneur into a serial entrepreneur.

Suppose you started a business to provide managed data analytics services to small and medium businesses. Then, you face the challenges of various AI tools that can also do what your business does at a competitive cost. 

So, you also enter the AI business, develop, market, and sell AI tools to new and existing customers. You adapted to the changes in the market and converted a challenge into an opportunity!  

#6. Pivoting in Response to Challenges

When faced with obstacles, you’re flexible. You’re quick to adjust your business model or strategy to overcome challenges. This adaptability ensures that setbacks don’t hinder your progress.

#7. Overcoming Failures

Failures are part of the entrepreneurial journey. You view them as valuable learning experiences. Each setback teaches you valuable lessons that you can apply to future ventures, ultimately making you a stronger and wiser entrepreneur.

#8. Staying Persistent

Persistence is the driving force for every serial entrepreneur. Even in the face of trouble, you thrive using your business expertise. You maintain the determination to achieve your goals, knowing that success often requires continuous effort and uncompromising belief in your vision.

Examples of Successful Serial Entrepreneurs

Elon Musk

Elon Musk is a renowned serial entrepreneur with a portfolio of many startups and businesses. He co-founded Zip2, an online business directory service. Then, he also founded, an online bank that later became PayPal. 

Musk’s serial entrepreneurial spirit continued with the creation of SpaceX. SpaceX is the world’s leading private aerospace manufacturer and space transportation company. He’s also the mastermind behind Tesla, the electric vehicle and clean energy company. 

Moreover, Elon Musk founded Neuralink, a neurotechnology company working in the healthcare niche. Last but not least, The Boring Company (TBC) focused on tunnel construction for transportation.

Sir Richard Branson

The serial entrepreneur Sir Richard Branson is the founder of Virgin Group. This business conglomerate is spread over 400 other companies in various sectors. 

The top subsidiaries of his group are Virgin Atlantic (airline), Virgin Galactic (aerospace travel), Virgin Hotels (hospitality industry), Virgin Megastores (retail), Virgin Mobile (telecommunications), Virgin Radio (media and entertainment), and so on. 

Steve Jobs

Steve Jobs is a visionary serial entrepreneur. He co-founded Apple Inc., the world’s leading technology company that makes iPhone, Mac, iPod, and smart applications that help home and business users.

After leaving Apple in 1985, he founded NeXT Inc., a computer hardware and software company.

Steve Jobs also played a pivotal role in the success of Pixar Animation Studios. Pixar is the renowned animation studio responsible for cherished films like Toy Story, Cars, Wall-E, A Bug’s Life, etc.

How to Become a Serial Entrepreneur

#1. Market Research and Analysis

To become a serial entrepreneur, you must start with a thorough market research and analysis. You should understand and closely monitor the market trends and consumer needs. This knowledge helps you identify opportunities and gaps in various industries.

#2. Niche Exploration

Next, explore different niches within your areas of interest. Look for niches that align with your skills and passions. Finding the right niche can give you a competitive edge. The niches you choose for serial startups must align with your previous market analysis and research.

#3. Continuous Learning

Always stay updated with industry developments and new technologies. Read books, attend workshops, and take online courses. Continuous learning keeps you ahead in the entrepreneurial game.

#4. Networking

Networking is also crucial. You should connect with fellow entrepreneurs, potential partners, and investors. Attend industry seminars and join business conventions to expand your network. 

Don’t forget to join some of these subscription-free startup communities as well. Networking also helps you hire talents and managers for your startups so you can easily exit to start a new one. 

#5. Mentorship and Guidance

It’s imperative that you get guidance from senior entrepreneurs and business persons who hold command in the field where your startup is dwelling. 

You’ll be able to extract first-hand experience and problem-solving ideas from your mentors so your serial startup game doesn’t face the same bottleneck that your mentors already faced. 

Also read: Platforms to Find Mentors To Grow and Transform Your Business Strategy

#6. Building Your Entrepreneurial Portfolio

You need to diversify your business portfolio. Don’t just start startups in the same sector. Because if one sector sees a correction in the market, businesses in other sectors will cover the losses. 

Your personal brand as an entrepreneur will also help you to succeed in getting startup funds when establishing serial ventures.

#7. Prioritizing Tasks

You must also learn to prioritize your tasks as a serial entrepreneur. Focus on high-impact activities that drive your ventures forward. Time management is key to overseeing multiple businesses at the same time.

#8. Delegating Responsibilities

You can never accomplish all the tasks in multiple businesses yourself. You must delegate your tasks to talented employees in the first startup. Then, before exiting, transfer the managerial control over to a responsible CEO. However, you can always stay connected with the business as a board of directors, majority shareholder, etc. 

#9. Analyzing Mistakes

In your serial entrepreneurship journey, you’ll make many mistakes. Don’t be afraid of them. Instead, put all the mistakes in a journal and analyze them. Find out how differently you could have taken an action to avoid making an incorrect decision. Apply the findings to the next startups. 

#10. Expanding Ventures

If you see your startup is making profits, you must immediately reinvest the profits into expanding the startup. Suppose your venture deals in one province; you should expand it into other states. If you sell products, start service-based sections like subscriptions to products, consultancy to other startups, etc., to diversify the company’s income source. 

#11. Achieving Sustainable Growth

You must create a balance between the sales orientation and customer centricity in overall business orientation. Don’t just push for short-term sales. You must push sales to grow revenue but also make relationships with customers to get repeat sales from existing customers. 

Pros and Cons of Serial Entrepreneurship

Find below why you might or might not want to become a founder who has set up many startups:


#1. Financial Rewards

Becoming a serial entrepreneur can lead to significant financial rewards. By starting and successfully running multiple businesses, you have the potential to generate multiple income streams and accumulate wealth. 

Each successful venture can bring in profits, and over time, these can add up substantially, providing financial security and freedom.

#2. Creative Freedom

As a serial entrepreneur, you have the creative freedom to pursue your passions and explore various industries and business concepts. You’re not limited to a single niche or role, allowing you to continuously challenge yourself and thereby innovate. This creative freedom can lead to more fulfilling and enjoyable work experiences.

#3. Legacy Building

Serial entrepreneurship allows you to leave a lasting legacy in the business world. With each successful venture, you contribute to your community, industry, or society as a whole. Your innovative ideas, products, and services can positively impact people’s lives. Building a legacy can be personally rewarding and fulfilling.


#1. High Risk

Serial entrepreneurship involves a higher degree of risk compared to focusing on a single business. Each new venture carries its own set of uncertainties. The more businesses you manage, the greater the exposure to potential financial losses.

#2. Work-Life Balance

Managing multiple ventures often demands a significant amount of time and energy. This can strain your work-life balance, causing you to spend long hours at work and leaving less time for personal and family life.

#3. Managing Multiple Ventures

When you’ve put yourself in the driving seat of many businesses, managing all of them efficiently can be extremely challenging. It can become really tough to give attention to all your startups. When you spread yourself too thin, you risk professional burnout and reduced performance in all the ventures.  

How Is a Serial Entrepreneur Different Than a Social Entrepreneur?

Serial and social entrepreneurs differ in their core objectives and focus. As a serial entrepreneur, your main goal is to create and run businesses to make profits. Ultimately, you’re looking to build up wealth from multiple successful startups. Also, you’re driven by the desire to innovate and excel in various business niches.

Contrarily, as a social entrepreneur, your primary aim is to address societal or environmental issues. Your focus is on creating businesses or organizations that have a positive impact on society, such as improving education, healthcare, or environmental sustainability.

Must-Read Books for Serial Entrepreneurs

#1. Press Go

Press Go describes the real-world experiences like challenges and success stories of Bill Seibel, a popular serial entrepreneur who has set up 9 startups on his own and worked with 30 other startups.

Preview Product Rating Price
Press Go: Lessons Earned by a Serial Entrepreneur Press Go: Lessons Earned by a Serial Entrepreneur No ratings yet $19.95

You’ll find proven insights into various stages of a business, like launching, product/service marketing, scaling up the business, and exiting to start another startup.  


BIG LUCKY offers you the secrets to serial entrepreneurship described by the former celebrity stylist and PureOlogy founder Jim Markham.

He has set up 5 successful companies that, in combination, sold $1.2 billion of products to retail customers. The positive messaging given in the book already helped hundreds of entrepreneurs set up their first startups.  

#3. Stepping Into the Moment

Stepping into the Moment explains how Roger Braswell, one of the popular serial entrepreneurs, built a lawn care business at the age of 15. Thirty years later, the company went public.

He set up multiple other successful businesses encompassing the landscaping, power equipment, startup advisory, etc., niches. So, if you’re planning to do something similar, this is a must-read book for you.   

#4. The Checkmate Formula

The Checkmate Formula book results from three decades of studying billionaires and visionaries who have been serial winners.

It offers a fresh perspective on the business world, providing answers to what determines success or failure in business and how serial entrepreneurs consistently win.


So, that’s how you go on pursuing a profession of serial entrepreneurship. Besides following the secret recipes mentioned here to make serial winning mission a success, also read the suggested books to get the wisdom you need.

Next up, No Ideas But Want to Start a Business? AI is Here to Help!

Share on:
  • Tamal Das
    Tamal is a freelance writer at Geekflare. He has an MS in Science and has worked at reputable IT consultancy companies to gain hands-on experience with IT technologies and business management. Now, he writes content on popular B2B and B2C IT…
  • Rashmi Sharma

    Rashmi is a highly experienced content manager, SEO specialist, and data analyst with over 7 years of expertise. She has a solid academic background in computer applications and a keen interest in data analysis.

    Rashmi is…

Thanks to our Sponsors

More great readings on Career

Power Your Business

Some of the tools and services to help your business grow.
  • The text-to-speech tool that uses AI to generate realistic human-like voices.

    Try Murf AI
  • Web scraping, residential proxy, proxy manager, web unlocker, search engine crawler, and all you need to collect web data.

    Try Brightdata
  • is an all-in-one work OS to help you manage projects, tasks, work, sales, CRM, operations, workflows, and more.

    Try Monday
  • Intruder is an online vulnerability scanner that finds cyber security weaknesses in your infrastructure, to avoid costly data breaches.

    Try Intruder