'Shark Tank' 's Barbara Corcoran Talks Starting Her Real Estate Business with $1,000 and 'A Lucky Break as a Diner Waitress'

"I met a man .. who told me he thought I'd be great at real estate and how about I give you 1,000 dollars." she says

Mike Pont/WireImage. Photo: Mike Pont/WireImage

Shark Tank's Barbara Corcoran is a bona fide businesswoman now, but the real estate mogul says she had had "22 jobs" before finding success.

"I happened to have a lucky break as a diner waitress," Corcoran, 68, tells PEOPLE of how she got her start with her former company, The Corcoran Group. "I met a man, who after a couple of months became my very first boyfriend, who told me he thought I'd be great at real estate and said, how about I give you 1,000 dollars."

The fortunate twist of fate paid off for the reality star — the Corcoran Group is still a leader in the industry. Although she sold the firm in 2001, the experience launched a career as a lifelong #girlboss.

"I realized I loved two things about [owning a business]: I wasn't behind a desk all day, and much more important than that, I didn't have a boss," says Corcoran, who is serving as a panelist at Saturday's T.J. Maxx's "The Maxx You Project Workshop," which aims to inspire women to pursue their own aspirations. "I never knew why I kept changing jobs, because I liked each and every one of them. But what I didn't like was someone telling me what to do."

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Consulting her mantra, "What would a man do?" during moments of insecurity, and a refusal to let male colleagues steal her credit — "I don't stand for it," she says — helped Corcoran dominate in her field.

Her biggest secret to success, though, requires no fight at all.

"I have an M.O. of consistently being nice and meaning it," she says. "Because an odd thing happens when you're nice to everyone — people like you. When people like you, they're willing to follow you or entertain your idea."

But don't let that fool you into thinking she's a pushover. "The only exception I have is when someone crosses the line and undermines you," she says. "I don't accept it."