Real estate entrepreneur Barbara Corcoran shared insights she's gained over a lifetime of building successful businesses and reinventing herself during a speech at Columbia Business School’s Alleycon.
Corcoran’s advice on overcoming setbacks as an entrepreneur fit in with Alleycon’s theme, Transform, which sought to explore disruptive innovation, evolving business models, and tech-driven change.
"The only difference between the really successful people and everybody else is not how hard they try. I really think everybody pretty much tries hard, but [it’s about] how well they take a hit and how long they take to get back up,” Corcoran said.
Through Corcoran's talk, her engaging personal anecdotes and hard-won lessons offered a roadmap for entrepreneurs to navigate the ups and downs of building a business and sustaining long-term success.
Let Failure Fuel Your Drive
Corcoran emphasized the need to turn one’s failures into fuel for future success. She pointed to her “Homes on Tape” initiative initially launched as a means to showcase properties for sale on video.
The project was met with resistance from both Corcoran’s clients and colleagues and did not take off. However, Corcoran would go on to repurpose the concept by moving the videos online during the rise of the internet. The idea was a success and allowed Corcoran to gain an early foothold online – before her competitors – giving her a significant advantage.
For Corcoran, every failure was simply another part of the process—a necessary ingredient in the recipe for long-term success. She noted that embracing failure as a learning opportunity is crucial for sustained innovation and growth.
Build the Right Team
While Corcoran found success as an entrepreneur, she noted that her success was not completely a solo venture; it was built on assembling a balanced team that complemented her strengths.
She explained that in any business, there are two types of people: “expanders” and “containers.” Expanders are bold, creative risk-takers who drive innovation and sales, while containers are organized and methodical, ensuring that systems run smoothly.
“Nobody's more important than each other, because you really need both to grow a business,” Corcoran said.
She highlighted the hiring of her eventual business partner, Esther Kaplan, who had remarkable organization skills. Although Kaplan was not a typical salesperson – she was quiet and petite according to Corcoran – she was a trustworthy “container” who had a knack for securing credit lines.
Kaplan’s skills as a reliable organizer, mixed with Corcoran’s abilities as a dynamic risk-taker made for a team capable of quick adaptation and efficiency, according to Corcoran.
Know When to Reinvent Yourself
Even at the peak of her success, Corcoran recognized the importance of reinvention. After she sold her real estate business for $66 million, she found herself wanting to continue working, but remained at a crossroads.
Rather than completely discarding her past, Corcoran conducted a candid self-assessment by reviewing all 23 jobs she had held over the years, noting what she loved and what she didn’t. The reflection revealed that her core strengths lay in salesmanship, engaging an audience, and working with the media. Rather than starting anew, she repackaged her abilities and pivoted into television, eventually landing numerous roles in media.
Her gradual re-invention eventually led to her being chosen as one of the original investors on Shark Tank. Corcoran acknowledged that evolving as an entrepreneur doesn’t require abandoning who you are—it means adapting and repackaging your proven strengths for new challenges.
"I knew there was going to be no such thing as reinvention. I wasn't going to reinvent myself. I'm just going to change my packaging,” Corcoran said.