“Man, this could be a really bad second half of my life. Or. I have to figure something out,” Wainwright, now 60, remembers saying to a girlfriend of hers. “I had never created my own business before. I had always been the gun to hire. … But I had to finally say, nobody is going to give me my dream job, so I better figure it out myself.”

Wainwright had an idea.

She had been inspired watching her shopping-obsessed friend buy clothing from a second-hand rack in the back of a fancy boutique. Her friend said that while she would never have gone to a consignment shop or bought expensive items on Ebay (too many knockoffs), she was pleased to find second hand luxury items from a trusted shop owner.

Wainwright did a flurry of research. At the time, the market for personal luxury items in the United States was $50 billion a year. Her deep knowledge of the e-commerce space from Pets.com gave her the confidence that second-hand luxury goods was not a market Amazon would easily replicate. There was too much labor and expertise required.

And then she went to her own closet. “I started pulling stuff out,” says Wainwright. To her surprise, she found 60 items that she could resell. (“I had a little hoard going in there! And I am not a hoarder!” she jokes.)

By March 2011, Wainwright had up the first version of The RealReal, a second-hand luxury marketplace website. That June, she started shipping the first purchases.

The RealReal deals in the likes of Chanel, Hermès, Louis Vuitton, Cartier, Rolex and Van Cleef & Arpels. Consignors earn as much as 70 percent of the items they sell. The RealReal does free in-home pick up, authentication and shipping.

Its first year, The RealReal did $10 million in sales, according to Wainwright.

Wainwright’s story is inspiring, but she’s not alone. A recent CNBC/SurveyMonkey Small Business Survey of more than 2000 small business owners found that almost 30 percent were between the age of 55 and 64. And another 22 percent are 65 and older.

Wainwright’s next move was to approach venture capitalists.

Being a woman, then in her mid-50s, pitching male VCs in their 20s and 30s was hard. Being known as the woman at the helm during the Pets.com fiasco didn’t make it easier. On top of that, Wainwright was trying to sell the idea of luxury fashion e-commerce when “Silicon Valley’s definition of luxury is a Tesla in every garage,” she says.

“It was really really hard. I didn’t have success until I reached a woman.”

It’s a scenario that’s not uncommon in the Valley. But Wainwright got the money she was looking for. To date, The RealReal has raised $173 million in venture capital from 22 investors in seven rounds of fundraising, according to public fundraising database Crunchbase.

In 2017, The RealReal will do more than $500 million in revenue and has 950 employees, says Wainwright. While she won’t give a timetable, Wainwright indicates that taking The RealReal public is part of her plan.

“I think going public is a really smart thing to do,” Wainwright says.

Since that awful day back in 2000 when Wainwright lost Pets.com and her husband, she has made quite the comeback. She’s also learned that, although it’s cliche, failure can lead to better things.

“You might just find that you have more,” writes Wainwright in a piece she penned for Forbes. “More inner strength, more tenacity, more grit, more courage, more kindness, more compassion than you ever thought was possible.

“Failure is ultimately very liberating,” says Wainwright. “Once you come out the other side of it, you just might have faced one of your biggest fears and lived. The other side of failure is a big elimination of fear of failure — trust me, that is an amazing gift.”

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See also:

How this mom turned $775 into a $65 million company in only 5 years

How America’s No. 1 small business got to $10 million brewing beer in Hawaii

Why this Harvard grad has spent a decade making maxi pads out of banana fibers