Mena and Ben Trott
Previous Lives: Laid-off Web designer and developer
Big Break: Created software for a personal blog
Bottom Line: Software became an industry standard
High school sweethearts from Petaluma, Calif., Mena and Ben Trott got into blogging after losing their jobs at a small San Francisco-based Web design firm in the dot-com bust. With extra time on their hands, they developed a software tool to help Mena post her personal blog. It worked. When they put the tool online in October 2001, nearly 200 people downloaded it within the first hour.
Initially working out of their apartment, the couple launched a software company, hired dozens of employees and raised over $10 million in venture capital. And as blogging took off, the tool they called Movable Type (after the Guttenberg printing press) became an industry standard.
"What had started as a hobby turned into full-time job, complete with 70 hour weeks," Mena says on the company's Web site.
The couple, both in their early 30s, have since added to their fortune by launching other blog publishing applications, including a successful hosting service. After the rapid growth of Movable Type, the couple says their current strategy is to build momentum slowly with a diverse line of inter-related products.
"I can't imagine where we'll be in a year, let alone five years," Mena says.
Richard and Betty James
Previous Life: Navy tool worker and homemaker
Big Break: Saw a spring coil fall off a table
Bottom Line: Called it a Slinky and sold 250 million of them
In 1943, Richard James was a navy tool worker in Philadelphia when he saw a torsion spring coil fall off a workshop table. Later at home, he considered turning the coil into a toy. Betty, his wife, found the term "Slinky" -- a Swedish word for sleek and sinuous in the dictionary. What followed were two years of testing various gauges of steel to find the perfect material and length.
By Christmas 1945, the new toy was ready for the market. The couple made 400 units, which they put on display at a Gimbel's Department Store for $1 each. Within an hour they were sold out.
With the proceeds, the coupled launched the James Spring and Wire Company, later renamed James Industries. Since then, more than 250 million Slinkys have been sold worldwide -- many still manufactured on the original production line.
In the late 1950s, Richard James nearly drove his once thriving business into bankruptcy by donating millions to a Bolivian religious cult that he left the company and his family to join in 1960. He died in obscurity 14 years later.
After her husband left, Betty continued to run the business, expanding its products to include plastic Slinkys, a Slinky dog, and fake glasses with Slinky extended eyeballs. In 2001, she was inducted into the Toy Industry Hall of Fame.
Previous Life: Launched an Internet service provider in Brazil
Big Break: Met a fellow Greek expat who made bikinis
Bottom Line: Became the world's largest independent distributor of Brazilian bikinis
In the late 1990s, Thales Panagides was a recent business school graduate from Ball State University in Muncie, Ind., when he flew to Brazil to help his cousin launch a small Internet service provider. He expected to return to the United States after a few weeks.
Based on an idyllic beach in Fortaleza, the small firm -- like so many others in the early days of the dot-com boom -- soon landed funding from a large venture capital group, which forced them to leave their beachfront office for the business district of Sao Paulo.
Despite the firm's success, Panagides longed to return to the beach. Looking to ditch the online world altogether, he started researching local product manufacturers with an eye to setting up a seaside exporting company back in Fortaleza. One of the first factories he visited was owned by a fellow Greek expat whose parents had immigrated to Brazil. The product they made was light-weight, compact and ideal for exporting -- Brazilian bikinis.
Leveraging both his MBA and his online expertise, Panagides bought a few samples and put 10 up for sale on eBay as a simple test. The next morning, seven of the bikinis had active buyers. "It was then that I knew I hit a home run," Panagides tells fellow Ball State alumni on the school's Web site.
Today, www.brazilian-bikinis.net is the largest independent distributor of Brazilian bikinis in the world, selling to retailers in more than 41 countries around the globe. As for himself, Panagides is back on the beach.
Catherine, Dave, and Geoff Cook
Previous Lives: High school students
Big Break: Teenagers at the dawn of the social media era
Bottom Line: MyYearbook.com has, at times, grown faster than Facebook or MySpace.
Frustrated by a lack of social media sites strictly for teens, these three siblings from suburban New Jersey hatched a plan around the family dinner table three years ago to put high school yearbooks online. Catherine, the youngest, was only 16 years old at the time. Yet she convinced her older brother Geoff, a 26-year-old Harvard grad, to put up $250,000 from his own fledgling online business -- and myYearbook.com was born.
Starting with their local high school, the Cooks have since expanded the site by more than 7 million members. And with more than 20 million unique visitors a month, it's had growth spurts that have outpaced both Facebook and MySpace. Its market share is up nearly 500 percent from last year, according to Hitwise. Not surprisingly, Nielsen NetRatings has ranked myYearbook among the Web's top social media sites for 12 to 17-year-olds.
"MyYearbook has charted phenomenal growth since the day my brother and I launched the site in the hallways of our high school," Catherine Cook, who's now 18, said about the most recent traffic figures.
Despite her phenomenal success, Catherine leads a fairly ordinary teenage life, calling herself a "nerd and proud of it." She's a member of a varsity gym team and has a boyfriend with a 4.0 GPA. Dave, a high school senior, says he gets decent enough grades and managed a good SAT score, despite the preoccupation of overseeing a professional staff of Web 2.0 software developers.
"You have to understand each other, and you have to be able to work together," Geoff Cook has said about launching a business with his siblings and dealing with investors.
Josh Abramson and Ricky Van Veen
Previous Lives: College students
Big Break: Created a website to trade jokes while attending different colleges
Bottom line: The site now boasts more than 8 million unique visitors a month
In 1999, these two Baltimore area high school friends created a goofy Web site to stay in touch when they went to separate colleges. They started out posting funny pictures of themselves doing gags and stunts, what Abramson has called "stupid college stuff."
Soon, they began forwarding links to their friends, who then passed them along to other students. Before long, college kids were sending Collegehumor.com their own photos and videos, attracting first thousands of visitors to the site every week -- then tens of thousands, then hundreds of thousands. By 2005, the site was getting up to 8 million unique visitors every month and generating millions in ad and merchandise sales.
By that point, Abramson, Van Veen, and two other 20-something friends had moved to New York and were sharing a 4,200-square-foot loft in Manhattan. More recently, Abramson, now 26, bought his own $1.975 million condo.
At a recent business conference in New York, Van Veen conceded that much of the site's success came from simply being in the right place at the right time. "When we started in 1999, we were one of the only games in town," he told organizers. They've since been forced to adapt to ramped up competition, he added.
Previous Life: Laid-off receptionist
Lucky Break: Was given a small portfolio of insurance policies as a severance package
Bottom Line: Recently sold her insurance businesses for more than $100 million.
At 42, this former receptionist was laid off by an American insurance firm based in the United Kingdom. Given a small portfolio of insurance policies on classic motorcycles as severance, she launched her own insurance consulting firm at her dining room table in the mid-1980s.
At the time, there were few insurance firms offering special policies for high-end motorcycles. As Nash set to work, she slowly discovered on untapped market. Over the next decade, she built Carole Nash Insurance Consultants into one of the United Kingdom's largest motorcycle insurance firms with more than 240,000 policyholders -- covering about a third of Britain's motorcycle owners and overseeing more than $100 million in premiums.
In 1999, Nash expanded into Ireland, opening up offices in Dublin. Over the years, she also broke into the classic car insurance market, along with a line of motorcycle security products.
Two years ago, Nash, a 66-year-old grandmother, sold the business to Groupama, a European Financial Services Group, for more than $100 million. "I am obviously sad to be retiring from a business that has been my life for the past 21 years," Nash said at the time. In recent years, she has appeared in rankings of the United Kingdom's wealthiest families.