GWallet's Chahal Balances Flashy Lifestyle, Family Commitment

While running his third startup, an entrepreneur known for talk-show appearances and swank parties keeps close to his lower-key relatives

In 1997, a year before he dropped out of high school, Gurbaksh Chahal wrote a letter to himself as part of a school assignment. His goals: caring for his family and becoming a doctor.

A decade later, his parents called to say the school had sent the letter. Chahal, now 27, never made it to medical school; that was his parents' dream, he says. Instead, he launched an entrepreneurial career that has netted two sizable sales of companies he started and has set the table for a third.

Chahal's latest venture, gWallet, lines up advertising inside social games on the Web. "I didn't have the appetite for learning in the classroom," says Chahal during an interview in gWallet's spare San Francisco office. "I was one of the few teenagers who loved CNBC."

Chahal, who lives in San Francisco's posh Infinity luxury condo tower, did realize his goal of taking care of his parents, who are originally from India and now reside in San Jose. In the past few years, he's paid off the mortgage on his parents' house, bought them each a new Lexus, and taken them on luxury vacations to Cabo San Lucas. "When I was 18, I was a millionaire and most people think having that much money requires retirement," says Chahal. "I wasn't going to retire at 18 or 21. At the end of the day, I never do anything for money."

Chahal has said he's worth more than $100 million, and he has the lifestyle to prove it. His routine includes swank parties, VIP trips to Vegas, and an auto ownership history that includes two Lamborghinis, a Ferrari, and a Bentley. He's appeared on The Oprah Winfrey Show and Fox's The Secret Millionaire, is considered one of San Francisco's most eligible bachelors, and has already written an autobiography, The Dream (Palgrave Macmillan, 2008), that tells his tale of rapid ascent.

"Single-Mindedness to Succeed"

"This guy is on track to be a billionaire," says Tim McAdam, general partner at Trinity Ventures, which invests in gWallet. "He is cut of the mold of a Larry Ellison or Richard Branson, these irreverent types who are incredibly tenacious visionaries. It's not about education, pedigree, or connectedness. It's about the single-mindedness to succeed."

GWallet lets Web users who play games on social networks such as Facebook watch video advertisements or fill out marketing surveys to earn virtual "currency" they can use inside the games. The company has deals with advertisers including Best Buy (BBY), Coca-Cola (KO), Nestlé (NESN:VX), and The History Channel. GWallet connects those companies to developers of social networking games, then takes a percentage of sales.

Two months after Chahal started gWallet last September, Adams Street Partners and Trinity Ventures led a $12.5 million round of venture funding.

GWallet follows two earlier companies Chahal successfully sold. In 2000, he sold online advertising company Click Agents for $40 million, though he wound up with about half that after his stock options in acquirer ValueClick (VCLK) declined. In 2007, Chahal and his investors sold online advertising network BlueLithium to Yahoo! (YHOO) for $300 million.

Chahal might be living the dream now, but he grew up poor. He was born in India's Punjab state the youngest of four children, to Sikh parents who immigrated to the U.S. when he was 3. He and his siblings remained behind for a year in the care of a grandmother while his parents found jobs and a one-bedroom apartment in a part of San Jose, Calif., that Chahal describes in his book as "gang-ridden."

Courting Developers and Advertisers

In his autobiography, Chahal recounts how he felt like an outsider growing up. Children mocked his head covering, calling him names like "turban head" and "Papa Smurf."

As a teen during the dot-com boom of the late '90s, Chahal became interested in the Internet and the stock market as he watched his father invest. Six months after starting Click Agents, Chahal said he was generating more than $100,000 a month in sales. His father worried he was doing something illegal.

Part of Chahal's job nowadays is attracting developers and advertisers to sign up for gWallet's network. During a game developers conference in March, Chahal threw a party at his penthouse, which boasts spectacular views of San Francisco's Bay Bridge. Ice sculptures sat slowly melting beside shots of Roberto Cavalli vodka. Photos of the event on the Web show a passel of miniskirt-wearing women. "The party was really fun, super flashy," says An Huynh, a former sales director who left gWallet in early April.

While his apartment might be flashy, gWallet's offices have the stripped-down look of a Silicon Valley startup. The walls are bare and employees toil quietly in cubicles. Chahal was subdued, mourning the recent death of his grandmother after her years of suffering from Alzheimer's disease. "I'm now at the epitome of my career and it would have been great for her to recognize it," he says, adding that he would have loved to have taken her on vacation and flown first class.

Sharing the trappings of success with his family is never far from the top of Chahal's list.

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