Successful Straight Out of the Gate

“The corporate ladder has been the primary career path for generations of businessmen. Each of them unfairly queued behind a less-deserving man, climbing the rungs of someone else’s company while bearing business cards highlighted by someone else’s name and vision. Climbing this ladder takes a long time and odds are poor you’ll even reach the top. For some men this is OK; it’s a life.”

“For others, queuing on another man’s ladder is no life at all. So they wager big, but not on a raise or a promotion; they bet on themselves and strike out on their own. Five such entrepreneurial gamblers follow, all of whom hit the jackpot before the age of 30.”

Chad Hurley
Primary achievement: Co-founded the video-sharing website YouTube.
Achieved success at: 29

“A fine arts graduate, Hurley landed a job at PayPal when the company purchased a logo he came up with (and are still using as their official logo). While working there, he became friends with PayPal engineers Steve Chen and Jawed Karim. One night in January of 2005, they wondered if there might be an easier way to share videos online than the methods available at the time. By the end of the calendar year, that “easier wayâ€? had a name: YouTube.”

“A year later, in October 2006, the friends sold YouTube to Google for $1.65 billion; Hurley’s share of the sale amounted to well over $300 million. Today he serves as the company’s CEO.”

Gregg Levin
Primary achievement: Founded Perfect Curve, Inc., a company specializing in accessories for caps.
Achieved success at: 29

“By 1994, Gregg Levin had grown tired of curving the bills of his baseball caps by hand and wondered if there might be a better way. He did some research into cap sales and found a $3 billion industry in which sales had been increasing at a steady rate for years. Using Play-Doh, he built what amounted to the prototype to his Perfect Curve AE Cap Curver. Despite some early resistance to the idea that anyone would buy a device that curves a cap’s bill, he launched Perfect Curve, Inc. in 1996 and has since sold over three million cap-curvers. Today, the company sells other cap accessories, including a rack, a care kit, a radio, and more.”

Mark Zuckerberg
Primary achievement: Founded the online social networking site
Achieved success at: 20

While still an undergraduate at Harvard, Zuckerberg launched “The Facebook,â€? a site meant to be an online social utility for other Harvard undergrads. Expansion was rapid; within a couple months it was available to a number of other — mostly Ivy League — schools. Shortly thereafter, Zuckerberg and his partners went west, to Silicon Valley, where the angel funds and venture capital began to pour in. In September 2006, Facebook lost all semblance of a site geared towards students and opened up to anyone on the internet.

Zuckerberg currently serves as’s CEO. He has reportedly turned down more than one offer in excess of $750 million to buy the site.

John Chuang
Primary achievement: Cofounded staffing service Aquent
Achieved success at: 26

“Chuang was a student at Harvard when he and two friends began a Macintosh-equipped desktop publishing business in their dorm rooms. Business boomed and in 1986 they leased some office space in Harvard Square. The following year they altered their business model, calling themselves MacTemps and becoming a staffing agency that specialized in Macintosh-trained temporary employees. By 1991, MacTemps was the 12th-fastest-growing private company in the country.”

“Today, Chuang is the CEO of MacTemps — long-since renamed Aquent — a $400 million business. He did not, however, drop out of Harvard; not only did Chuang graduate cum laude in 1987, but earned his MBA with honors from Harvard in 1992.”

Daymond John
Primary achievement: Founded the hip-hop clothing label FUBU.
Achieved success at: 26

“John’s career as a clothier began in New York in 1992, making hats in his mother’s basement to sell at neighborhood concerts. Modest success was swift: John recruited three longtime friends, then took out a $100,000 mortgage and began to expand. Shortly thereafter, and with the support of John’s friend LL Cool J, FUBU (an acronym: “For Us, By Usâ€?, meant to represent the localized, urban identity of the apparel and the founders), began to take off, diversifying into shirts, jerseys and other items.”

“Today, FUBU is an internationally recognized, multimillion dollar sportswear company. John is its CEO and president, but he hasn’t forgotten about his roots: In 1999 he established the FUBU Foundation, the company’s charitable wing, which remains active in a variety of community affairs.”

Straight out of the gates…

“The entrepreneurial spirit is the roulette wheel of the soul. Either it spins within you or it doesn’t. If it does, placing those chips is probably the scariest bet you’ll ever make. Maybe it seems too scary, and that would be understandable — but would it be excusable?”

“While few see the success these guys are seeing, even losing that bet might make life on the corporate ladder more tolerable. But if you never take it, don’t be surprised when your pension checks feel like you’re getting paid to pass the day in bitterness and regret.”

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