Entrepreneur Insight

How Do Serial Entrepreneurs Keep Succeeding?

How do serial entrepreneurs launch one business after another, and achieve results?

Recent studies and surveys cite key characteristics that serial entrepreneurs share: innovation, risk taking, high levels of motivation, the desire to capitalize on ideas, and the ability to build wealth by owning companies. Admittedly, these characteristics are not that much different from the entrepreneurs who create just a single entity.

However, at least two different studies—a 2013 study of business owners conducted by the Center of Economy and Finance in Portugal, and a 2008 study led by the Harvard Business School—suggest that serial entrepreneurs possess an innate ability to be repeatedly successful because they have an added ability to time the market—to select the right industry at the right time, just when businesses in that industry are peaking.

Kalika Yap

For serial entrepreneur Kalika Yap, innate ability appears to have propelled her into her first business, Citrus Studios, a website design company.

“I was scared to start my first business, but it felt completely natural,” she says. “I really enjoyed it; I certainly had a knack.”

A former broadcast journalist with Bloomberg News and CNBC, Yap says she came to California in 1996 without a job and became enthralled with the Internet. With Yahoo Inc. as a sponsor, she says she held seminars on the history of the Internet and, later, got a job at the J. Paul Getty Trust where she held “web raisings,” building websites in a day for nonprofits. Soon, she says, she earned more from her freelance website construction than Getty paid her and she left to create Citrus Studios in 1999.

Yap says she borrowed $400 to pay her incorporation fee, placed a used computer on an $80 Ikea desk and opened her shop. She entered the market when web development standards were being created by the grassroots Web Standards Project. Over time, website construction became less expensive and less complex and websites proliferated.

Yap attributes her company’s success to good market timing, which helped the company grow to 20 employees in Santa Monica and Honolulu, with cumulative sales of $25 million.

Innovating and Capitalizing on an Idea

In creating her second business, Luxe Link, Yap demonstrated other serial entrepreneur characteristics: innovating and capitalizing on an idea. The idea for this business emerged in 2004 while she was on vacation in Italy. A restaurant owner lent her a large hook from which to hang her purse from her table so she didn’t have to put it on the floor, Yap says.

“It was such a great idea, but not a good idea to carry around a gigantic hook,” she says.

After 18 months and a trip to the Canton Fair, the entrepreneurial trade show in Guangzhou, China, Yap says she designed a patented, collapsible hook.

Yap's invention the Luxe Link (Photo credit:) courtesy of Kalika Yap

Serial entrepreneurs possess an innate ability to be repeatedly successful because they have an added ability to time the market.

“I spent thousands of dollars,” she says. “I created it because I thought it was a really good idea and I was very tenacious, very passionate about the idea. I was obsessed.”

About the circumference of a half-dollar, Luxe Link comes in a variety of styles. Yap says it has earned her several million dollars in sales from Hong Kong, Australia, Japan, China, New Zealand, Brazil and the United States.

Repeated Success

Subsequent ventures have also been successful for Yap, giving her the repeated victories typical of serial entrepreneurs. She helped start the first waxing salon in Honolulu in 2009 when her sister-in-law asked for help with The Waxing Company, she says. It now employs 18 people, services 5,000 clients yearly and brings in about $1 million in revenue, Yap says.

Her newest ventures sprang from Citrus. The Tangerine Co. which provides photography and videos for websites, and The Lemonade Stand will soon offer a subscription model to create affordable websites for smaller businesses, she says.

“I have a lot of ideas, but I don’t start things unless I’m passionate,” she says. “I think the reason why I succeed is that I really believe and expect to succeed.”

Gustavo Occhiuzzo

Like Yap, Argentine-born serial entrepreneur Gustavo Occhiuzzo appears to have relied on innate skill to create businesses all his life, starting with a lawn-mowing service he says he created at age eight and continuing with two other successful businesses he says he ran in Buenos Aries.

After coming to Los Angeles in 1996, Occhiuzzo started Pan American Landscaping in 2003 and sold it in 2014. Between 2005 and 2009, the company secured numerous government and commercial projects. He says they included a new park at Van Nuys City Hall, the City of Los Angeles’ Orcutt Ranch and Brand Park, Santa Ana Zoo landscape improvements, and Los Angeles County Public Works Arrow Highway bike path.

He also created Pan American Brush Clearance in 2003. He says he grew it from a few thousand dollars in annual revenue to $1.3 million last year, with contracts with the City of Los Angeles’ Fire Department and the Department of Recreation and Parks. It also holds contracts with the City of Pasadena and the County of Los Angeles, he says. He sold it in 2009 for $520,000 but continued to run it as CEO until 2014, when he left to work on Green Commuter.

In 2010, another entrepreneur asked him for help in turning around a failing landscaping business. He actively managed BMC Landscape Management Inc., growing it from its $30,000 purchase price to sell it for $630,000 in July 2015. During the five years Occhiuzzo owned it, he says he and his partner took out more than $500,000 in shareholder distributions. At the time of its sale, the company had 25 commercial and government contracts with $2 million in gross revenue projected for 2015.

During the 2009 economic downturn, he correctly gauged the market and created Antelope Valley Holdings. He bought eight houses for $900,000, remodeled them to rent out and has consequently generated more than $1 million in rental income and appreciation.

Market Timing

Today, he is pursuing his newest dream venture, Green Commuter, a blend of vanpooling and car-sharing, at a time when Internet-linked commuting solutions are eagerly being used and created. He says he has invested $500,000 in the venture and anticipates spending another $1 million, in addition to securing a commercial fleet loan, plus possibly another $2 million later from investors.

Occhiuzzo’s concept involves morning commuters riding together to their workplaces in all-electric vehicles. Rather than have the vehicles sit idle at the end destinations, workers at the location and members could rent the cars for short trips during the day until they are used again as van-pool vehicles for the evening commute.

The service could start operating in early 2016. The plan is for workplaces and universities to contract with Green Commuter for van-pooling services and for a Green Commuter-developed software app to keep track of the vehicles.

Challenges include obtaining a fleet of all-electric vehicles, devising the computer software to run the blended van-pooling and car-sharing system and assisting in the creation of a new insurance program for this unique operation. But Occhiuzzo is confident he and his seven employees will succeed.

“I look to the future and I see three to five years ahead with the business at its peak and all the work I will have to do,” he says. “I know the company will get there . . . because I’ve seen it!”