How To Become a Successful Serial Entrepreneur: 5 Tips

Steve Jobs is best known as the co-founder and former CEO of Apple, but that’s just one of his entrepreneurial achievements. He went on to build multiple additional businesses, including the iconic production company Pixar, which he acquired and led as CEO and chairman. Jobs is an example of a serial entrepreneur, someone who builds a career from starting one new business after another.

An advantage of being a serial entrepreneur is that you’re not starting fresh with every new business venture. You have a knowledge base and skill set that you can carry over. This experience can lead to more sales: A Shopify survey found entrepreneurs who previously launched a business on the platform and returned to start a second one earned more than twice the sales per shop on average when compared with first-time founders. 

In this article, you’ll find examples of serial entrepreneurship in action. Learn what’s required to be successful, with insights from founders who have started more than one business. 

What is a serial entrepreneur?

A serial entrepreneur is an individual who starts, manages, and potentially exits multiple businesses or ventures throughout their career. Unlike entrepreneurs who focus on growing a single company, serial entrepreneurs thrive on the process of building a new venture and starting the process over again. Their entrepreneurial endeavors sometimes span diverse industries. 

Oprah Winfrey is a famous example of a serial entrepreneur. The former talk show host built an empire by launching Harpo Studios; founding O, The Oprah Magazine, and creating digital offshoots Oprah Daily and Oprah Insider. Winfrey also co-produced the 2005 Broadway musical The Color Purple and its 2023 film adaptation, and created the Oprah Winfrey Network (OWN).

Serial entrepreneurship may appeal to people who want to make a lasting impact, spot opportunities others miss, and take calculated risks.

4 serial entrepreneur examples in ecommerce

• Ryan Babenzien
• Dan Demsky
• Mimi Ikonn
• Zachary Quinn

Though serial entrepreneurs have a knack for finding gaps in the market, what helps them in their new endeavors are the valuable lessons they learn from their past businesses. 

Here are four serial entrepreneurs to inspire your journey:

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. His first company was the premium sneaker brand GREATS.

“Even within those big companies, I was always very entrepreneurial about my approach,” Ryan says on an episode of Shopify Masters. “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 results from 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 filtered showerhead brand 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, like dry skin, but 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. 

Dan Demsky

When Dan Demsky was in his early 20s, he and his friend decided to launch a video production company as a side hustle. Before they knew it, they had a real business on their hands—which they called Bizmedia. 

“Fast-forward two years,” Dan says on Shopify Masters. “And we were downtown in a big studio, there were 15 of us, and it was a legitimate company.”

Soon Dan and his business partners started a new side hustle—a brand of sweat-wicking merino wool menswear that was ideal for travel. 

For Dan, the endeavor was anchored in his own desire for T-shirts that didn’t exist yet, and he didn’t let fear of failure get in the way. “This is the way I looked at it: This thing’s either going to work and will have made our dream business, or it won’t and I’ll have a box of prototype T-shirts that I wanted anyway. This is a win-win. It’s enough to take a step. I didn’t even care if it failed because at least I tried.”

By fall of 2025, the brand approached $100 million in cumulative lifetime revenue.

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, Mimi launched journal company Intelligent Change while still at the helm of her first company. 

After selling Luxy Hair, Mimi went all in on Intelligent Change, which has sold more than three million copies of their flagship product, the Five Minute Journal.

At the core of Mimi’s entrepreneurial strategy is her mastery of audience growth. By sharing her passion about hair, Mimi 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—because her existing fans tagged along for her new venture. 

“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.”

Without that existing audience, Mimi says Intelligent Change wouldn’t have grown as quickly. 

Zachary Quinn

Zachary Quinn’s ventures, the charitable beanie brand Love Your Melon and sustainable activewear company 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,” Zachary says on Shopify Masters. 

Zachary gravitates toward impactful, purpose-driven businesses. He co-founded the beanie company Love Your Melon in 2012 as a college student. Love Your Melon has grown into a multimillion-dollar brand that’s donated nearly $10 million to pediatric cancer research and gifted more than 300,000 beanies to children with cancer. Later, Quinn 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 continued working for the brand, became a dad, and eventually tackled his new business. Zachary later bought back Love Your Melon, resuming his role as CEO after a four-year break.

What it takes to be a successful serial entrepreneur: 5 tips

• Apply your learnings
• Evolve from founder to CEO
• Find your fun quotient
• Manage small failures
• Exit on your own terms

Serial entrepreneurs need a unique blend of resilience, adaptability, and strategic thinking. Here are five key guidelines for success in your entrepreneurial ventures:

Apply your learnings

Setbacks are common for serial entrepreneurs, but it can help to view each failure as a valuable learning experience. 

For example, Ryan learned about the pitfalls of the fashion 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.” 

When he started Jolie, he applied his hard-won insights, focusing on a product that wasn’t subject to sizing issues—or trends. 

“If there was something that was universal, it would be much easier to have a DTC [direct-to-consumer]-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.”

Ryan’s work with GREATS gave him a unique perspective on DTC’s strengths and limitations as a standalone business model.

“I started Greats as the door was closing to DTC 1.0,” Ryan says. “Then very quickly the market realized that DTC is not a business model: It’s a distribution channel. The DTC brands that are surviving are the ones that are big time into retail.”

This insight informed his decision to work with major retailers in his next business. Jolie is now available at Ulta, Costco, and Erewhon.

Evolve from founder to CEO 

As a successful serial entrepreneur, when Dan scaled his second company, Unbound Merino, to $100 million, he started to grasp the difference between being a founder versus being a CEO. 

“At some point you have to figure out what a CEO is,” Dan says. “What the team really needs is for me to remind everyone where we’re going—what the vision of the company is—and to make sure we’re doing the right things to get there. I’m starting to learn that these leadership qualities of a CEO are the things that are completely new to me that I need to develop. ” 

Dan’s journey to becoming a stronger CEO has included defining a clear brand identity and giving employees space to do their best work.

“What I’ve come to realize is I just need to make sure that I’m fostering a culture where people feel like they know, ‘This is what our brand is.’ And they have autonomy in helping us achieve whatever these things are.”

Find your fun quotient 

Running a business is hard work, so a serial entrepreneur needs to have stamina and resilience to keep going through multiple ventures. For Byron Peart, co-founder of apparel brand WANT Les Essentials and curated marketplace Goodee, the work is to continuously tap into a sense of joy. 

“We’re second-time founders and I still haven’t found my fun quotient at enough of a level,” Byron, who co-founded both brands with his twin, Dexter Peart, says on Shopify Masters. “Fun is making sure that you’re able to maintain that joy and all the reasons why you did it in the first place. Our business has a lot of backstops that create that—and fun shows up all the time—but it’s extremely, extremely important to have joy in what you do.”

Manage small failures

Dealing with failure is an essential skill for serial entrepreneurs, especially those who have a drive to continue building new businesses. 

Paul Tran, founder and CEO of grooming brand Manscaped, sees failure in your first business as a necessary stop on the way to future success. 

“Quite honestly, it’s highly unlikely that your first business is going to be successful. But that’s the stepping stone to your next successful business. And then the one after that,” Paul says on Shopify Masters. 

Ryan of Jolie also sees managing the cycle of failure and fixes to be a necessary skill for a serial entrepreneur. “Failure’s part of it, and you have to be good at failing,” Ryan says. “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. 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.”

Exit on your own terms

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. “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.”

But this went against Mimi and her business partner’s plans for themselves. They didn’t want to feel tethered to a job, so they handed the business off to a new leader 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.” 

Selling the business without staying involved day to day let Mimi turn her focus to Intelligent Change. She was able to build a well-loved brand that has expanded beyond the Five Minute Journal.