It was 1973 and Corcoran desperately needed workers to join her budding real estate company. “But I had little to offer, and good people were really hard to get,” the 74-year-old millionaire investor and real estate entrepreneur revealed in a recent TikTok video.

Enter Kaplan. The “petite woman” came to apply for a sales job “in a little knit suit with little pearl buttons,” Corcoran recalled, adding that she “spoke so softly I could barely hear what she was saying.” 

It was in stark contrast to what Corcoran thought a successful salesperson should look like: “Loud and enthusiastic,” as she puts it.

“So I handed Esther my card and told her I’d call her if something opened, having no intention of calling her,” she said.

Based on the snap judgment, the Shark Tank star admitted that she almost passed over “the best hire” she ever made. But then her mind was instantly changed when Kaplan opened her purse to put the card away and Corcoran she caught a glimpse inside.

“She had the tiniest, tidiest filing system I ever saw with partitions that were labeled all inside her purse,” she added. “With a mind like that, I knew I wanted my business in her purse.”

It impressed Corcoran so much that she offered Kaplan a job on the spot—leading to her big break. 

While Kaplan never did become a “superstar salesman”, within two years she was running the company “side by side” with Corcoran and went on to serve as president of the Corcoran Group for three decades.

Ultimately, the story has a double whammy lesson for both workers and bosses: For one, you really never know what you’re being judged on. Meanwhile, for bosses, it’s a reminder that the person who looks wrong for the job might just be their best hire yet.

“She had all the needed traits I didn’t have,” Corcoran said. “If you don’t have all the needed traits to build a business, find a partner who does.”

Your big break can come from anywhere—or anyone

Corcoran knows all too well that your big break can come from anywhere—or anyone. She founded the Corcoran Group after an unexpected encounter while she was waiting tables at just 22 years old.

“That diner waitress job you’re busing tables for? It’s gonna change your life,” she previously wrote in a note to her younger self on Instagram. “Trust me on this.”

It was there that she met a man named Ramone Simone, who after dating for a year fronted the $1,000 the pair needed to launch a real estate brokerage company together. They split seven years later in 1978 and Corcoran continued with the Corcoran Group.

Back then there were no female-owned real estate firms in the city, but she went on to become one of the biggest names in the industry and eventually sold the company for a staggering $66 million in 2001.

“When that handsome man offers you a ride home, you better take it,” Corcoran concluded; Essentially, you never know where your next windfall will come from.