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When Steve Jobs left Apple in 1985, he didn’t rest on his laurels. He went on to start and nourish multiple businesses, including the iconic production company Pixar, which he heavily funded and guided as its chairman. Jobs is an example of a serial entrepreneur, someone who starts one new business after another.
Do successful serial entrepreneurs always launch successful ventures? No. Jobs himself struck out with his post-Apple company, NeXT Computers, which folded in 1997. However, by relentlessly seeking out new ventures, he demonstrated the traits of serial entrepreneurship, which stuck with him even when he returned to Apple.
You don’t need to be the co-founder of Apple to be a successful serial entrepreneur. All you need is relentless drive, new ideas, and the ability to sell yourself to venture investors whose money can help get your startup off the ground. Here are some insights into how many serial entrepreneurs create a string of successful enterprises.
What is a serial entrepreneur?
A serial entrepreneur is an individual who starts, manages, and (ideally) sells multiple businesses or ventures throughout their career. Unlike traditional entrepreneurs who focus on growing a single company, serial entrepreneurs thrive on the process of creation and innovation. Their entrepreneurial ventures often span diverse industries.
Some famous examples include: Richard Branson, founder of the Virgin Group, who started his career with Virgin Records before expanding into radio channels, airlines (Virgin Atlantic and Virgin America), space travel (Virgin Galactic), a rail franchise (Virgin Trains), and telecommunications (Virgin Mobile); Oprah Winfrey, host of the iconic daytime talk show that bears her name, who built an empire by launching Harpo Productions, founding O, The Oprah Magazine, co-producing the Broadway musical The Color Purple, and creating the Oprah Winfrey Network (OWN); and Wayne Huizenga, who co-founded Waste Management Inc., as well as other successful businesses such as Blockbuster Video and AutoNation. Huizenga also thrived as a sports owner of the Miami Dolphins, Florida Panthers, and Florida Marlins.
Serial entrepreneurs often possess a knack for identifying new opportunities, an appetite for calculated risks, and the ability to scale businesses before selling them or passing the leadership torch.
4 examples of serial entrepreneurs in ecommerce
- Wil Yeung
- Mimi Ikon
- Zachary Quinn
- Alex Matthews
For most serial entrepreneurs, success comes from clearly identifying a target market and building a business that meets that market’s needs or fills a gap in the market. But they don’t stop there. Serial entrepreneurs learn valuable lessons from their first business and apply those lessons to future endeavors. Here are four serial entrepreneurs with ecommerce expertise who may inspire your own forays into business:
1. Wil Yeung
Perhaps you know Wil Yeung from the Yeung Man Cooking YouTube show. If so, you probably wouldn’t guess that his first business venture involved flipping violins on eBay, where he realized he could stand out by offering better photos and descriptions than his competitors. From there, he expanded into dropshipping, started a brick-and-mortar music school, ran a wedding and commercial photography business, worked as a salt wholesaler, and made real estate investments. When the pandemic hit, Wil pivoted to YouTube, growing his channel by doubling his production schedule and creating additional income streams through a cookbook and online course.
“Money is a byproduct of the value that you create,” Wil says in an episode of the Shopify Masters podcast. In the early stages of your new startup, focus on how your product or service will improve the lives of your clients. If your idea resonates and you manage your business well, the money will flow. The most successful ventures are those that truly serve the needs of a market and aren’t just designed to make a quick buck.
2. Mimi Ikonn
Mimi Ikonn is a serial entrepreneur who co-founded Luxy Hair in 2010, building it into a multimillion-dollar hair extensions brand with a YouTube channel that amassed more than three million subscribers. After selling the company, she launched Intelligent Change, achieving further success by selling more than two million copies of its flagship product, the Five Minute Journal.
Mimi’s entrepreneurial strategy centers around her mastery of YouTube as a platform for community building and business growth. This comes naturally to Mimi because she loves her industry. “It’s about enjoying what you’re doing because that will resonate with the audience,” Mimi says on Shopify Masters. As an entrepreneur, you’ll be investing countless hours in your startup. Make sure that you’ll be happy making such an investment.
3. Zachary Quinn
Zachary Quinn co-founded the hat company Love Your Melon in 2012 as a college student. He built it into a multimillion-dollar company that donated nearly $10 million to pediatric cancer research and gifted more than 250,000 beanies to children battling cancer. Zachary eventually sold Love Your Melon and launched Oceanfoam in December 2023, creating eco-friendly foam rollers made from sea algae and recycled materials.
From one business to the next, Zachary’s entrepreneurial process has involved keeping a running list of ideas, embracing mission-driven business models, and collaborating with innovative partners who are willing to work with his vision. Oceanfoam combines sustainability, function, and aesthetic design, helping it stand out in its industry for its environmental impact.
“It’s important to notice the ideas that rise to the top of your list that you keep coming back to the most,” Zachary says on an episode of Shopify Masters. “That’s what I decide to work on and go after.”
4. Alex Matthews
Alex Matthews is the co-founder of De La Calle, a Mexican soda brand. Working in the highly competitive shelf-stable drinks category, Alex’s experience as a serial entrepreneur was invaluable. He’d previously started a juice company, is a cofounder of a series of LA eateries, and has his own branding agency LOAF Brands. This latter came in particularly handy when De La Calle had to pivot its sales and marketing strategy to explain their niche product to a broader audience. It was about making a little change that isn’t a complete revolution but crisps up the description,” Alex says on the Shopify Masters podcast.
His team at De La Calle have the same entrepreneurial spirit. “We’ve all made mistakes, you know. Been through the ringer, I guess you could call it. And so we were bringing some collective experience to the table,” he says.
4 tips for becoming a successful serial entrepreneur
- Practice resilience and patience
- Meet the needs of the market
- Improve your team-building and networking skills
- Develop your financial acumen
Becoming a serial entrepreneur doesn’t require boundless wealth or connections, but you do need to cultivate a unique blend of resilience, adaptability, and strategic thinking. Here are four key guidelines for success in your entrepreneurial ventures:
1. Practice resilience and patience
Many successful serial entrepreneurs have faced setbacks. View each failure as a valuable learning experience. If a business fails, analyze what went wrong, extract key takeaways, and apply those lessons to your next venture.
Before diving into multiple ventures at once, focus on building a successful track record with at least a couple of your early projects. This demonstrates your ability to execute and manage businesses, making it easier to attract investors and build credibility. For example, if your first business was a successful local bakery, use the knowledge gained to open a second location or a related food service.
2. Meet the needs of the market
Look for gaps in the market or emerging trends. For example, the rise of mobile network technology created opportunities for app development and mobile-first businesses.
Before investing significant resources, thoroughly validate your product or service concept. This includes conducting market research, gathering customer feedback, and creating prototypes. Apply the key takeaways from your research to your emerging business. Clear product conceptualization and a thorough understanding of the market may inspire outsiders to invest in your business.
Design your businesses with scalability in mind. Consider how your business model can be replicated and expanded to reach a wider audience.
3. Improve your team-building and networking skills
Surround yourself with skilled and passionate individuals who complement your strengths. Attend industry events, connect with other entrepreneurs and self-employed people, and build relationships with potential investors. These connections can provide valuable insights and opportunities.
As you manage multiple ventures, learn to delegate tasks and empower your team. This frees up your time to focus on strategic planning and new opportunities.
4. Develop your financial acumen
Research various funding options, such as:
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Angel investors. An angel investor is a person who provides your fledgling company with funding in exchange for an ownership stake. They typically look for passionate founders who could benefit from their advice as much as their financial support.
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Venture capital. Venture capital is money that privately owned companies provide in exchange for partial ownership. Instead of working with one individual, you might work with multiple investors from a firm.
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Crowdfunding. Crowdfunding is a fundraising tool in which you gather small donations from a lot of people—like social media followers, friends, and early adopters of your business.
Be prepared to present a compelling business plan and financial projections. If you plan to solicit large investments, or eventually become a publicly traded company, you will need to understand and comply with regulations set by entities such as the Securities and Exchange Commission (SEC).
When you achieve success with one venture, consider reinvesting profits into other startups. This can create a portfolio of businesses and diversify your financial risk.
Serial entrepreneur FAQ
What are some characteristics of a serial entrepreneur?
Serial entrepreneurs often possess characteristics such as a relentless drive, a penchant for seeing business opportunities, a high tolerance for risk, and an ability to capitalize on their ventures.
How much do serial entrepreneurs make?
Some serial entrepreneurs lose money in the early years of their startup businesses. With perseverance, skill, and luck, many make comfortable salaries ranging from five figures to many millions.
What are some businesses serial entrepreneurs have founded?
Serial entrepreneur Richard Branson founded multiple businesses bearing the Virgin name, including Virgin Records, Virgin Atlantic, Virgin America, Virgin Galactic, and Virgin Mobile. Serial entrepreneur Wayne Huizenga co-founded or reimagined multiple iconic businesses, including Waste Management Inc., Blockbuster Video, and AutoTrader.
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Credit: Original article published here.