Bill Rancic, the first winner of Donald Trump's "The Apprentice," shared his insights on success and failure as an entrepreneur, how reality TV changed his life, and his former boss's presidency at a Schaumburg Business Association breakfast Tuesday.
Rancic, a south suburban native who's remained true to his Chicago roots, told the large crowd that a passion for business was part of him from an early age -- even before "The Apprentice" helped expedite his path.
After his grandmother taught him how to make pancakes in her kitchen when he was a kid, he soon discovered her friends would leave $5 bills under their plates when he made them all breakfast. But he eventually had to explain his new love for "Grandma's House" to his mother.
"I had to fess up: I was running a makeshift restaurant out of my grandmother's kitchen," Rancic said.
Creating a boat washing and waxing business to pay his way through Loyola University introduced him to the owners of those boats -- successful businesspeople who didn't seem all that different in character from himself.
He'd already had several successful ventures -- including a "cigar of the month" business that got him on Chicago-based radio and TV talk shows -- before "The Apprenctice" came along in 2004.
Rancic says he never had a strong expectation of winning, and when he did, he hoped the fame would help buoy his career for about six months.
"It was a total mystery," he said. "Reality TV was in its infancy. For me, it was always about being true to myself and letting my actions speak louder than my words."
He never expected it would lead to meeting his wife, Giuliana. She interviewed him for "E! News." Later they co-starred in the long-running reality series "Giuliana and Bill."
"The Apprentice" also led to his overseeing construction of Trump Tower in Chicago, a job where he continued to get an up-close view of the man who would become the 45th president of the United States.
Rancic said he believes Trump really wanted him to do well, and that he's now focused on wanting America to do well.
"He knows how to lead. He knows how to get things done," Rancic said of Trump. "If he can do for our country what he did for me, I think America is going to be in a really good place."
He said that while Trump is extremely busy with many unprecedented situations, the time to judge his results will be in November 2020.
Though still primarily in the real estate field, Rancic today is particularly focused on expansion of the RPM Restaurants chain he's a partner in as well as launching a wine project with his wife.
He wanted his audience to know that failure has been a part of his career as much as any businessperson's, but that how it's handled is the key to everything. He once thought he was finished forever when a building he was renovating burned down and he had the wrong type of insurance.
"I was able to survive it, but I needed to be agile," Rancic said. "I think it comes down to not wanting to accept failure. I think you either have that or you don't."
He told the audience he'd identified three characteristics of success for entrepreneurs -- knowing it's more important to show than to tell, understanding the importance of agility, and both respecting and managing risk.
Three more traits he says he's seen in the best of them are good decision-making, creativity and a no-excuses mindset even when plans fall apart.
"Tough times don't last, but tough people do," Rancic said.
One of the people he met whom he most admires is the late comedian Joan Rivers, who considered herself like a bumblebee -- able to fly despite its being aerodynamically impossible.
"She was able to fly because she didn't realize she couldn't and she wouldn't let people tell her she couldn't," he said.