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.
Serial entrepreneurs don’t always launch successful ventures. Jobs struck out with his post-Apple company, NeXT Computers, which folded in 1997. However, by relentlessly seeking 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 cofounder of Apple to be a 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. Read on for 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.
Oprah Winfrey is a famous example of a serial entrepreneur. Oprah built an empire by launching Harpo Productions, founding O, The Oprah Magazine, coproducing the 2005 Broadway musical The Color Purple and the 2023 film adaptation, and creating the Oprah Winfrey Network.
Serial entrepreneurs typically want to change things, spot opportunities others miss, and take calculated risks.
Ryan Babenzien, the serial entrepreneur behind sneaker brand Greats and filtered showerhead brand Jolie, puts it this way: “[Entrepreneurs] certainly don’t play it safe. They want to change things.”
He also cites conviction as an important characteristic. “[To be an entrepreneur], you need conviction in a way that is irrational,” Ryan says. “I believe in my ideas so greatly that I can get through all of the challenges.”
5 serial entrepreneurs examples in ecommerce
Many serial entrepreneurs have a knack for finding a gap in the market. But what helps them in their new endeavors are the valuable lessons they learn from their past businesses.
Here are five serial entrepreneurs with ecommerce expertise who may inspire your own forays into business:
1. Ryan Babenzien
Ryan Babenzien had a corporate career before becoming a serial entrepreneur, working in corporate finance and for footwear juggernauts Puma and K-Swiss.
“Even within those big companies, I was always very entrepreneurial about my approach,” Ryan says. “I was never good at following rules. That’s been a lifelong thing. I always felt that if there’s a better way, shouldn’t we be trying that better way?”
Ryan’s entrepreneurial drive is tied to his desire to create things that solve problems.
“With Greats, it was, ‘Why are we paying $500 for sneakers made in Italy? I think we can solve that problem and make it less expensive,’” he says. “It’s a simple problem, but a problem I felt could be eliminated.”
With Jolie, Ryan believed the beauty industry was ignoring a big problem: water. “They were trying to solve the issues that were starting from the water, except they were ignoring that source. I decided we should be a beauty wellness company that purifies your water for better skin, hair, and health,” he says.
2. Wil Yeung
Wil Yeung started Yeung Man Cooking, a YouTube channel with 1.5 million subscribers, to share his plant-based recipes. However, his first business venture involved flipping violins on eBay. He realized he could stand out by offering better photos and descriptions than his competitors.
From there, he expanded into dropshipping, sold coconut milk, 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 Wil started a YouTube account, he was trying to promote his coconut milk business. He filmed videos showing potential customers what they could do with the product. He posted recipes here and there. Years later, he decided to lean into cooking.
Eventually, Wil pivoted to YouTube, growing his channel by doubling his production schedule and creating additional income streams through a cookbook and online course.
Being a serial entrepreneur doesn’t mean that all your companies will succeed, but, like Wil, you can learn how to overcome failure in business. Wil used his past experiences to grow Yeung Man Cooking.
“There are so many transferable skill sets that I acquired during my previous ‘failed businesses,’” Will says on an episode of the Shopify Masters podcast. For instance, photography and videography … because I’ve acquired those skill sets, it’s completely accelerated how I run the YouTube channel.”
3. Mimi Ikonn
Mimi Ikonn is a serial entrepreneur who cofounded Luxy Hair in 2010, building it into a multimillion-dollar hair extensions brand. Three years later, she launched Intelligent Change, while still helming her first company. It wasn’t until Luxy Hair sold a few years later that she could go all in on Intelligent Change, which sold more than three million copies of its flagship product, the Five Minute Journal.
Mimi’s entrepreneurial strategy hinges on her mastery of audience growth. By sharing her passion about hair, she amassed more than three million subscribers on Luxy Hair’s YouTube account.
When she turned her focus to Intelligent Change, she didn’t have to start building an audience from scratch.
“I was very fortunate because I already had an audience that transitioned with me from Luxy Hair to Intelligent Change,” she says on Shopify Masters. “That’s the beautiful thing about content creation. When you create content, regardless of what you talk about, you build trust. So then if you choose to sell [something else], if you have the trust of your audience, people will support whatever it is that you’re doing because they support and trust you. If it wasn’t for the audience, we wouldn’t have been where we are today.”
4. Zachary Quinn
Zachary Quinn’s ventures, Love Your Melon and Oceanfoam, started as business ideas on a whiteboard. “I start by creating a list of ideas that I’d like to work on, and it just kind of dwindles down to the ones I really keep coming back to,” he says on Shopify Masters. “You start to notice the ones that rise to the top and that you keep coming back to the most. That’s what I decided to work on.”
Zachary gravitates toward impactful, purpose-driven businesses. He cofounded the beanie company Love Your Melon in 2012 as a college student. It grew into a multimillion-dollar brand that donated nearly $10 million to pediatric cancer research and gifted more than 250,000 beanies to children with cancer. Later, he founded Oceanfoam, which sells eco-friendly foam rollers made from sea algae and recycled materials.
“It’s really important to me that we have an impact,” he says. “That it’s not just running a business to make money.”
Zachary helped run Love Your Melon for a decade before the business sold. He didn’t immediately jump into another business venture. Instead, he worked for Love Your Melon as he adjusted to becoming a father and having a job for the first time. The entire time, he thought about foam rollers, but it took him two years to tackle a new business.
5. Alex Matthews
Alex Matthews is the cofounder of De La Calle, a Mexican soda brand, and founder of the branding agency Loaf Brands (formerly Here Studios). With his brands, Alex combines his love for the food and beverage industry with his background in marketing.
“I love consumer packaged goods and wanted to package all of those things and work with other brands,” he says on Shopify Masters.
While they are distinct businesses, there is sometimes overlap between the two. For example, the team at Loaf Brands handled the rebrand for De La Calle. “We worked all of us really collaboratively,” Alex says.
6 tips for becoming a successful serial entrepreneur
- Apply your learnings
- Understand the market
- Network with an open mind
- Tout past successes when fundraising
- Manage small failures
- Exit on your own terms
To become a serial entrepreneur, you need to cultivate a unique blend of resilience, adaptability, and strategic thinking. Here are six key guidelines for success in your entrepreneurial ventures:
1. Apply your learnings
Many serial entrepreneurs have faced setbacks, but they view each failure as a valuable learning experience.
For example, Ryan learned about the pitfalls of the direct-to-consumer (DTC) model and the shoe business while building Greats. “[Sizing] is really difficult and there are a lot of reversed logistics costs,” Ryan says. “If it doesn’t fit, you have to send it back, and then we send you another. It’s not an elegant business.”
Moreover, customer acquisition costs were increasing, as platforms like Meta raised ad prices.
When he started Jolie, he applied his hard-won insights, focusing on a product that wasn’t subject to trends or sizing issues. “If there was something that was universal, it would be much easier to have a DTC-oriented business,” Ryan says. “Plumbing in America and most of the world is standardized, so it’s one-size-fits-all. And consumer behavior is very hard to shift. Trends come in and out, but we shower every single day.”
He also eschewed the DTC-only model in favor of working with retailers. Jolie is now available at Ulta, Costco, and Erewhon.
“All the lessons from building Greats were applied,” Ryan says.
2. Understand the market
Serial entrepreneurs need to understand the target audience for every business they launch. If you have industry knowledge from your career, you may be able to lean on that. But if you don’t, you have to fill the gap with market research.
Ryan was well-positioned to launch Greats. Having worked in the sneaker industry, he understood the space. This helped him successfully identify a gap in the market.
However, when he was thinking about starting Jolie, he knew he needed to do more market research. Studying beauty and showerhead brands, he realized there was an opportunity to create a unique product.
“The market didn’t even exist,” he says. “I did a lot more research on understanding how bad is water? How much is it really affecting us? Your skin is the largest organ on your body. Everything that’s in the water is being absorbed over time. The beauty market is focused on the things they do. The shower companies are not even thinking about this.”
It took three years for Ryan to feel comfortable launching Jolie. By then, he had learned about water and how the beauty industry priced its products. The research he did during that time continues to shape how the company positions its product. For example, on its homepage, the brand explains how heavy metals and chlorine in water can damage skin and hair.
3. Network with an open mind
Networking can help you establish relationships that can further your business. Ryan advises approaching it with an open mind, rather than a strictly transactional attitude. “You never know who’s going to ignite a spark,” he says.
Ryan’s advice stems from his time in the corporate world. While working in marketing at K-Swiss, he got an introduction to the CEO of J.Crew, Mickey Drexler, by asking for a meeting.
“K-Swiss had been trying to sell into J.Crew for years but could never do it,” Ryan says. But rather than treating the meeting like an opportunity to make a hard sell—which could make it feel transactional—Ryan took a different approach.
“I remember the CEO of K-Swiss saying, ‘What shoes are you bringing?’ I said, ‘I’m not bringing shoes. I’m not on a sales call. I’m going to tell them about the brand, what we’re going to do, and how the brand’s going to get reignited.’ Lo and behold, J.Crew started carrying K-Swiss.”
“I think everybody should find that spirit of networking,” Ryan says. “Maybe not just for the purpose of, ‘What can you do for me?’ [but rather] ‘Is there something that you and I together can do for someone else?’”
4. Tout past successes when fundraising
A successful track record as an entrepreneur can help you raise capital for your next business(es).
If you’re putting together an investment proposal for a second or third business, highlight how you delivered value for backers—even if you bootstrapped or only worked with traditional lenders in the past.
Alex of De la Calle suggests looking for investors who can be patient. “Most beverage brands lose money for quite some time at the beginning,” he says. “Three to four years, maybe five years, you’re not making money. You’re losing money. Having a patient investor and partners on your team to understand that from the outset is pretty important.”
5. Manage small failures
Dealing with failure is an essential skill for entrepreneurs—especially those who have an appetite for multiple businesses. “Failure’s part of it, and you have to be good at failing,” says Ryan. “You have to recover from failure in a way that allows you to keep going.
“Fail, fix; fail, fix; fail, fix: That is how I see entrepreneurship. The ones that can better and faster are going to find success in this sort of amalgam of small failures. We’re not talking about a big failure that’s fatal to your business, but you have to be able to manage these little ones in order to grow stronger.”
In the early days of Jolie, Ryan and team launched a bundle package, which negatively impacted their conversion rate—rapidly. “We were not ready to manage through it, so we just turned it off,” Ryan says. “That was a failure, but it wasn’t catastrophic. We still believe we should be able to bundle Jolie’s products. Maybe somebody has three bathrooms, and they want to buy Jolie all at the same time. But we were at a stage where we were not ready to sell bundles.”
6. Be thoughtful about your exit
If you begin to feel like it’s time to exit one of your businesses to focus on another, structure a transition that will allow your first business to continue thriving. When Mimi of Intelligent Change was still running Luxy Hair, she knew it wasn’t where she saw herself long-term.
“Three, four years into having Luxy Hair, we knew this is not something we’re going to do forever,” Mimi says of cofounder Alex Ikonn. “So we started thinking, ‘If we were to sell this business, what would it look like?’ As we looked at other people who were selling businesses, we realized that most of the time when you sell a business, you would have to stay in the business and run it for the next few years. That’s just part of the deal. Nobody wants to lose you, the main operator and the vision of the business.”
However, that went against Mimi and her business partner&rsquao;s plans for themselves. They didn’t want to feel tethered to a job.
The duo was in talks with a company that wanted them to stay on for at least two years. Instead, Mimi and her partner found someone to run the business from Toronto, who eventually became the CEO.
“While we were on the board and we were still in all the meetings and the team was executing our vision, we were not there day-to-day,” Mimi says. “She was running the show. For us, the vision was that when the business gets sold, she will have to stay with the business. And that’s exactly what ended up happening.”
Selling the business without having to be involved let Mimi turn her focus to Intelligent Change, where she was able to build a well-beloved brand that has expanded beyond the Five-Minute Journal.
Serial entrepreneur FAQ
What are some characteristics of a serial entrepreneur?
Serial entrepreneurs often possess characteristics such as a relentless drive, an eye for gaps in the market, and an ability to recover from failure.
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?
A few examples of businesses founded by serial entrepreneurs include:
- The Oprah Winfrey Network. Oprah founded Harpo Productions and O, the Oprah Magazine before launching the Oprah Winfrey Network.
- Virgin Atlantic. Richard Branson founded multiple businesses bearing the Virgin name, including Virgin Records, Virgin Atlantic, Virgin America, Virgin Galactic, and Virgin Mobile.
- Blockbuster Video. The video-rental giant was cofounded by Wayne Huizenga, who reimagined multiple other iconic businesses, including Waste Management Inc. and AutoTrader.
Who are some of the most successful serial entrepreneurs?
Some successful serial entrepreneurs include Steve Jobs (Apple, Pixar) and Oprah Winfrey (Harpo Productions, O, the Oprah Magazine, Oprah Winfrey Network).
