Here's How Barbara Corcoran Turned a Huge 'Flop' Into Pioneering Real Estate Technology "Shark Tank" star Barbara Corcoran was ahead of her time when it comes to putting real estate listings online.

By Erin Davis

Key Takeaways

  • Barbara Corcoran founded the Corcoran Group and sold it in 2001 for $66 million.
  • Corcoran says she lost tens of thousands on a "genius" idea that failed but ended up being successful years later.
  • "The best successes often happen on the heels of failure," Corcoran says.

Many entrepreneurs have a deal they probably wish they didn't make, or, perhaps worse, one that got away. And real estate pioneer and longtime "Shark Tank" investor Barbara Corcoran remembers hers clearly. She told her Instagram followers on Monday that she invested her first major profit into a "genius" idea that ended up being a total flop — and a bit ahead of its time.

"My greatest successes happened on the heels of failure," Corcoran wrote. "The moment I made my first profit, it felt like all the long nights and rejection finally paid off. I wanted to invest it in something big that would set me apart."

Related: How Nvidia CEO Jensen Huang Transformed a Graphics Card Company Into an AI Giant: 'One of the Most Remarkable Business Pivots in History'

Corcoran says she "took every penny" she had, which was around $75,000 at the time, and made videotapes of all of her company's real estate listings.

"I thought it was genius!" she said. "Buyers could pop in a tape and tour our apartments from the comfort of their La-Z-Boy chair."

However, Corcoran didn't anticipate her fellow real estate agents not wanting to hand out tapes with her face on it (and not their own). So, tens of thousands of dollars worth of VHS tapes went into boxes and "sat untouched" in storage.

"My brilliant idea was a total flop," Corcoran said. "Just like that, my $75,000 was gone."

But when the Internet went mainstream shortly after, she knew she was back in business.

Related: Barbara Corcoran Needed to Make Job Cuts. Here's Why She Fired Her Mom First.

"I heard whispers about this brand new thing called 'the Internet.' Most people thought it was a joke," Corcoran said. "I didn't. I registered my company's URL immediately, and I snagged my competitor's, too. (That's a story for another day.) Then, I remembered those dusty tapes."

Corcoran says she took the boxes out of storage, uploaded the tapes to the website, and within a week had "two sales came in from London, site unseen."

"The same idea that had failed miserably suddenly became my breakthrough," Corcoran says. "The best successes often happen on the heels of failure."

Moral of the story? Put your failures in a box out of sight, but don't throw them away — you never know when they can be repurposed into success.

Related: 'I Don't Know How I Know This, But I Know This': Learn This Psychic Medium's Method for Trusting Your Intuition

Erin Davis

Entrepreneur Staff

Trending News Writer

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Side Hustle

This Mom's Creative Side Hustle Started As a Hobby With Less Than $100 — Then Grew Into a Business Averaging $570,000 a Month: 'It's Crazy'

After Krista LeRay shared her passion project on Instagram, she realized there was enough demand to start a business.

Leadership

10 Underrated Podcasts Every Entrepreneur Should Be Listening To

These 10 podcasts cut through the noise with unfiltered lessons, unconventional strategies and stories that actually prepare you for the entrepreneurial grind.

Business News

Here's How Barbara Corcoran Turned a Huge 'Flop' Into Pioneering Real Estate Technology

"Shark Tank" star Barbara Corcoran was ahead of her time when it comes to putting real estate listings online.

Growing a Business

Taylor Swift and Amazon Share This 'Destructive' Superpower That Drives Serious Success, Says Former Harvard Business School Strategist

Sinéad O'Sullivan breaks down how two of the most powerful brands in the world propelled themselves to the top.