Navigate serial entrepreneurship: Tips from proven winners

Serial entrepreneurs are driven by the excitement of pursuing new business initiatives and are always seeking the next opportunity. Whether a new industry, market, solution, or product, a serial entrepreneur is constantly exploring something new. 

Being a serial entrepreneur is an excellent way to gain experiences and skills that can be applied to new ventures and industries.

In this article, we explore more about serial entrepreneurship, examples of successful serial entrepreneurs, and tips and traits from success.

What is a serial entrepreneur?

Most business owners focus on a single venture. However, a serial entrepreneur is always looking for the next big thing and prefers to have multiple businesses on the go.

A serial entrepreneur will pursue a new business idea, launch a business, make it a success, and move on to the next venture.

The original business may be sold, or a serial entrepreneur will retain control but step back from a leadership role and delegate day-to-day operations to a manager or entrepreneurial team.

When an entrepreneur sells a profitable venture, they can experience significant financial gains. However, if the business fails, the time and investment are a loss.

Serial entrepreneur examples

Most serial entrepreneurs are successful without attracting the limelight. Others have gone on to generate headlines. Here are some examples of high-profile serial entrepreneurs:

Elon Musk: Best known for Tesla and Space X, Musk’s earlier ventures were examples of serial entrepreneurship. He created and sold video games. He also founded a digital content company, Zip2, that helped print media organizations get online as well as a direct bank, X.com. Perhaps more prolifically, Musk co-founded PayPal and steered it through major expansion.

Oprah Winfrey: While famed for her eponymous TV show, Winfrey is a hugely successful and influential serial entrepreneur. She founded Harpo Productions, a multimedia production company in 1986, the Oprah Book Club in 1996, and O, the Oprah Magazine in 2000. In 2006, Winfrey expanded into satellite radio, starting Oprah Radio on Sirius XM. Since then, she went on to co-found the Oprah Winfrey Network (OWN), a cable network targeting women. 

Sir Richard Branson: Branson founded the Virgin Group in 1970 but began as a serial entrepreneur at the age of 16 when he launched a magazine, Student. Soon after he started the Virgin Mail Order Records company, followed by a Virgin Records store in 1972. Today, the Virgin Group owns 40 companies across the globe, including an airline, cruise line, and space tourism company.

Wayne Huizenga: Huizenga is the serial entrepreneur behind several highly profitable brands, including Blockbuster, Waste Management, and AutoNation. He was the first businessperson to launch three Fortune 500 companies.

Steve Jobs: Co-founder of Apple, Jobs also founded NeXT, a computer platform aimed at higher education and business markets. He also founded the computer graphics division of Lucasfilm which eventually became Pixar, the production company behind Toy Story and dozens of movies.

Tips and traits for becoming a successful serial entrepreneur

Serial entrepreneurs have many common traits including an innovation mindset, willingness to take risks, and resilience (useful in the face of challenges and failure). Other traits and tips for success include:

• Adaptability: Serial entrepreneurs can adapt to changing market conditions and business winds. Furthermore, they know that what worked yesterday may not work tomorrow and can adjust accordingly.
• Prior business experience: Many serial entrepreneurs have worked for other successful enterprises and have a track record of success. They also possess experience in management, and technology, and understand operationally what’s involved with a startup. Each business venture brings new experiences that serial entrepreneurs learn from and apply to their next venture. 
• Teamwork: Serial entrepreneurs understand the importance of strong leadership, management, people skills, and teamwork. As Richard Branson famously said: “Nobody can be successful alone, and you cannot be a great leader without great people to lead.”
• A funding strategy: To be successful, a serial entrepreneur starts thinking about funding the moment they have a business idea. Funding can come from their savings, a bank loan, assistance from the Small Business Administration (SBA), crowdfunding, or a private investor. It’s important to understand that business structure can impact investment opportunities. For example, legal counsel often recommends that startups who seek venture capital (VC) funding form a C corporation since many VC firms won’t invest in LLCs or S corporations. It’s also possible to form an LLC or S corporation first and then convert to a C corporation at a later date.
• Having an exit strategy: A key skill of any serial entrepreneur is knowing when to exit a business. An exit strategy includes plans to sell, transfer, or close the business, whether through an acquisition, IPO, liquidation, or dissolution. The choice of exit strategy can have a big impact on an entrepreneur’s life and finances, as well as the future of the businesses they launch.

BizFilings can help

Keep on top of regulatory obligations across your business entity life cycle. BizFilings can help you form a C corporation in three easy steps. When the nature of your business changes, we can help you change your entity type from a corporation to an LLC – and do it appropriately based on where your company was formed. And if you decide to cease operations, BizFilings can help you file the documents necessary to dissolve your business.