By Chase Stewart


Picking a favorite woman in business is a daunting task. I had a really difficult time narrowing my choices down to five favorites, let alone one! Before we get to it, let me give a shoutout to my favorite non-celebrity woman in business: my wife Kayla. Kayla is a Regional Vice President of Sales at Paycom Software, the youngest in the company’s history to serve in that role. I could not be prouder to be married to such a boss. Without a doubt, she is a future “SHE-E-O!” Ahem. CEO.

Back to the matter at hand, my favorite woman in business outside of Kayla, Michelle, and the brilliant female colleagues at G & G (shoutout to Katie, Rebecca, and Catie!), is none other than Mrs. Shark Tank herself, Barbara Corcoran.

One more small diversion: Neither I nor G & G Law represents Barbara Corcoran (although that would surely make my job even more fun). We are relying on news reports to provide the context of her situation, but we have not verified whether these reports are correct and we do not have first-hand knowledge of these situations or sales figures. Our goal is to think through what might have happened in these situations to enlighten regular, non-celebrity entrepreneurs. That said, if you’re a superstar in search of legal advice, by all means reach out!

Before becoming a venture investor on the ABC show Shark Tank, Corcoran was raised as the second of ten kids in the gritty, blue-collar town of Edgewater, New Jersey. Growing up, Corcoran was mocked as the “dumb kid” in school, struggling mightily to read and write due to undiagnosed dyslexia. Despite the detractions of her classmates, Corcoran dreamt big, using their jeers as motivation to work harder and master the skills necessary to succeed.

After a series of 22 different jobs, Corcoran began her career in real estate as a receptionist for the Giffuni Brothers. She worked there until her then-boyfriend, Ray Simone, loaned her $1,000 to start her own real estate firm in 1973. When Corcoan-Simone was founded, Corcoran was only 23. The first few years of business went well, but in 1978 Simone abruptly left Corcoran and married her assistant. Unsurprisingly, their business relationship ended with their romance, and Corcoran recounts Simone saying as he left their office for the last time “You’ll never succeed without me!”

Boy, was he wrong. Over the next two decades, she built Corcoran Group into an empire. What began with selling apartments on the Upper East Side of Manhattan grew into a real estate conglomerate that Corcoran sold for $66 million in 2001.

Corcoran credits much of her success to an unexpected source: her life-long struggle with self-doubt. From her early experience with dyslexia, to Simone and others scoffing at the prospect of her success, to running up against the “good old boys club” in New York’s real estate market, she’s no stranger to second-guessing yourself. However, Corcoran firmly believes that this can lead to great success. She elaborated in a recent episode of her podcast:

“Self-doubt is a human element that keeps you on the straight and narrow. The curse of being competent in self-doubt, because competence rides on your own self-doubt. Everyone I know who has been enormously successful struggles with self-doubt.”

(The podcast is called 888-Barbara and I highly recommend the listen!)

Nowadays, Corcoran uses her self-made wealth and fame to make a positive impact in the lives of entrepreneurs on Shark Tank, investing nearly $5.5 million over her eight seasons on the show. Corcoran told Inc. Magazine that, perhaps unsurprisingly, she sees the same grit that powered her rise in her most prosperous investments:

“My most successful entrepreneurs didn’t all have miserable childhoods, or grow up poor, but they had somebody who told them they couldn’t accomplish something, and they are still pissed.”

We all experience self-doubt in one form or another, and we can find inspiration in individuals who forge their insecurities into ironclad resolve. Corcoran is a shining example. She used her trials – childhood destitution, academic difficulties, constant dismissals from her peers, resistance from the “good old boys club” – to fuel her meteoric ascent, shattering expectations and glass ceilings at every turn.