David Schottenstein founded his first company at age 12, after he noticed how popular cigars were among the businessmen who visited his father, Thomas Schottenstein, a principal of Arshot Investment Corp. So he started his own cigar business on the sly and ran it for two years before his father found out and shut it down. He then moved on to trading Internet and pharmaceutical stocks, also without his father’s permission; that career was also cut short when his father found out. But while attending a Jewish boarding school in Venice, Schottenstein discovered his love of fashion and created a business of which even his father would approve.

A big fan of the British tailoring tradition, Schottenstein started Astor & Black, a company that sold custom bespoke clothing, at the tender age of 21. He used money he had saved from his previous business ventures to fund his vision, which was to bring custom tailoring to the general public at affordable prices. The suits, which are made in China, Hong Kong, Italy, and Brooklyn, start at $499; prices increase depending on the fabric, with the bulk of transactions in the $895 range. Schottenstein’s fixed costs are low because Astor & Black does not stock inventory and sales representatives need only minimal office space. Most offline sales occur in a client’s home or office.

The company initially grew through word of mouth and networking around Columbus, Ohio. Over time, Astor & Black signed up a sales force of independent reps; there are now 80 of them across the United States, Israel, and Australia.  The company has grown from revenues of a little more than $1 million in 2005 to more than $11 million in 2009.  Astor & Black is on pace to reach $22 million in sales this year.

Astor & Black’s client base includes corporate executives, celebrities, and professional athletes in the NBA, NFL, and NHL. Shawne Marrimen, Anthony Gonzalez, Greg Oden and the Jonas Brothers all have Astor & Black suits in their closets, according to Schottenstein.

Online, the company will launch a virtual custom tailoring experience this summer, which will allow customers to store their measurements, create a simulated version online of the outfit they want, and then place an order. Schottenstein also plans to open retail space on Madison Avenue in New York City and in Las Vegas He describes these showrooms as inspired by old English clubs; each will be decorated with leather chairs and couches, a cigar bar for customers, and an ample supply of scotch. Schottenstein wants Astor & Black to develop over time into a full-fledged lifestyle brand including jeans, sport coats, slacks, ties, belts, shoes, and more.

Schottenstein says the biggest obstacle faced by young entrepreneurs is themselves. “People have great ideas all the time but find all the reasons not to do it,” said Schottenstein.  “You have to be fearless and do not internalize rejection.”  He shared the story of how a potential customer told him to leave him alone, in not so nice terms.  “I ran into him at an event and pitched him again and he said ‘You really are a piece of work’ and he finally agreed to meet with me.” Today that same man is his biggest customer.   “Be brazen or you will be done on the day you start,” says Schottenstein. No doubt his father would be proud.