Donald Trump

Tycoons tend to start facing the same basic set of challenges as small business owners: creating a name, staying afloat and thinking one step ahead of the competition. But the scale of a tycoon’s interests and ambitions dwarf those of ordinary business owners, with the scale of a tycoon’s projects rivaling and at times surpassing those of governments. With Stanford and his railroad, Hearst and his media empire, it’s real estate that made Donald Trump.

While New York has always been kind to big business (think Rockefeller Center), it gives its rewards grudgingly, and only the most dynamic of movers and shakers will make it to the top. Luckily for Donald Trump, born in New York City on June 14, 1946 he received a first-class education in real world business practices. The son of a wealthy businessman and realtor, Donald Trump reaped the benefits of his pedigree less through cash and capital and more through witnessing his father in action—he was there firsthand to see how his father negotiated, planned and executed his business deals.

Having witnessed an early age how the world of business works, Donald Trump had the confidence and know-how to present himself as a valuable resource to people that would later finance him and put him in the right places to advance what would become a massive real estate empire. He began to establish himself by bluffing his way into a New York club for high rollers, despite not meeting the typical membership profile.

This kind of moxie would characterize Donald Trump’s entire business career. Unshakable faith in himself led him through what were, by his standards, the rather lean 1990’s (he at one point declared bankruptcy despite having been a multibillionaire). His commitment to his own personal style and image carried over to his realty projects, which tended to be high profile buildings such as hotels and casinos rather than more conventional properties.

Onto his third marriage and having famously plowed through innumerable mistresses, his prodigious love life matches his business drive. The father of several children that are in their own right on the way to distinction, Trump has raised his profile through his involvement with beauty pageants and the hit NBC reality show “The Apprentice,” which tests contestants’ business savvy and serves up criticism and reward in equal measure.