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Diary of a CEO · 2022-12-15 · 1h 11m

Barbara Corcoran: Turning $1,000 to $1Billion! | E204

Barbara Corcoran on turning $1,000 into a real estate empire, dyslexia as fuel, and why she bets on poor, damaged entrepreneurs.

Barbara Corcoran: Turning $1,000 to $1Billion! | E204
The guest

Barbara Corcoran — Real estate mogul who built The Corcoran Group into New York's biggest residential firm from a $1,000 loan, and a long-running investor on Shark Tank.

The gist

Barbara Corcoran traces her drive to a crowded, loving but volatile childhood as one of ten children, a hard-working mother, and a father whose drinking taught her to crave control. Dyslexia and a teacher who called her stupid became the engine behind a lifelong need to prove she's not dumb. She explains how she outmaneuvered New York's complacent old-boys real estate network through speed, imagination, publicity stunts, and a fun-first company culture with near-zero turnover. She is blunt about firing negative people fast, treating every employee as an individual, and using flirtation and being underestimated as competitive advantages. On Shark Tank she invests in people not businesses, favoring poor or damaged entrepreneurs who take responsibility and refuse to play the victim.

Big reveals

  • A third-grade teacher told her 'if you don't learn to read you'll always be stupid,' a label that silenced her through high school.
  • She believes that if she weren't dyslexic and hadn't struggled in school she would not have been successful.
  • Her boyfriend and 51% business partner Ramon Simone ran off with her secretary in the seventh year, which pushed her to start The Corcoran Group alone.
  • She admits she loved firing people on Friday and would schedule it days in advance.
  • After 14 years on Shark Tank she never chooses a business, she always chooses the entrepreneur.
  • She says she has no rich kid in her whole portfolio who succeeded; her winners are all poor kids with something to prove.
  • Out-earning her FBI-agent husband Bill by a mile made her feel 'not feminine enough,' like the caveman instead of the cavewoman.

Things worth remembering

  • She was one of ten children raised by two parents in a two-bedroom apartment.
  • She held about 22 jobs before starting her own business at age 23.
  • Nine of the ten Corcoran children went on to run their own businesses.
  • She took algebra four times across two summers and never passed; they finally just gave her the grade.
  • Her real estate firm became the biggest residential brokerage in New York before she sold it.
  • She threw themed parties, once filling the Waldorf Astoria ballroom with a thousand guests dressed as nuns.
  • She fired about a third of her sales staff every year for not selling, yet had essentially no voluntary turnover.
  • She keeps a 'hallway of doom' of Shark Tank entrepreneurs' photos and flips them upside down when founders behave like victims.
  • When she first out-earned husband Bill she lied and called it an accounting error.