When “Unemployable” Becomes Unstoppable

Julie Wainwright launched the luxury consignment platform The RealReal at age 52—not long after someone labeled her “unemployable.” On a recent episode of “Your Money Map,” Wainwright opened up about her new book, “Time to Get Real,” sharing lessons from failure, what it takes to start over in midlife and why age can be an entrepreneur’s secret weapon.

FOLLOWING HER GUT

Wainwright’s career has been extraordinary – and far from linear. Her story is one of trusting intuition and taking bold (but calculated) risks.

At 24, she left a high-powered job at Clorox to take a 50% pay cut and join the emerging tech world. “I knew that was the future,” she recalls. She quickly rose through the ranks, eventually becoming CEO of the online pet supply retailer Pets.com. In 2000, she took the company public – a feat accomplished by fewer than 30 women – only to see it collapse months later when the dot-com bubble burst. At the same time, her husband asked for a divorce.

The professional and personal setbacks hit hard. And when a recruiter later told her she was “unemployable” at 52, she realized something had to change. “By the time the recruiter had told me that, I had sort of level set, but I was so tired of letting other people’s opinion of something I had done 10 years ago actually define me,” shares Wainwright.

FROM REJECTION TO REINVENTION

Rather than dwell on rejection, Wainwright chose reinvention. She loved creating things, understood the business world deeply and always felt drawn to entrepreneurship. “Even though I’d been doing entrepreneurial things, I hadn’t really been an entrepreneur, and I thought I owed it to myself to do this, and if it doesn’t work out, I wasn’t going to beat myself up, but I needed to try,” she shares.

Try she did. She founded The RealReal from her home, creating an online luxury consignment store that hit $10 million in revenue in its first year. “I knew right away on the first sale, the first time we opened our virtual doors…I knew I had a winner,” says Wainwright.

Wainwright moved on from The RealReal in 2022 and has since launched another startup, but remains proud of its journey – from a one-woman idea to a publicly traded company that employs thousands. “It was humbling, it was gratifying, and most of all, it was fun,” she shares.

WHY AGE IS AN ENTREPRENEUR’S SECRET WEAPON

Starting over in midlife came with its own lessons that Wainwright says others can learn from. Chief among them is that age isn’t a liability; it’s leverage. “Having all that experience…it allows you to move faster, make confident decisions and understand,” she says. “You’re sort of like one of those wonderful rocks you find in the ocean, you’ve been rubbed and softened.”

As Wainwright describes, experience, resilience and perspective often make for sharper instincts – and a better shot at success. Research agrees. According to MIT’s recent Age and High Growth Entrepreneurship Study, which analyzed 2.7 million people who started companies, a 50-year-old is twice as likely to have a massive success compared to a 30-year-old.

TURNING FAILURE INTO FUEL

For Wainwright, the very experiences that once felt devastating – the fall of Pets.com, her divorce – became the foundation of her success.

“Once you’ve been through the fire, you don’t want to necessarily get back in it, but if you get out of it, you know that if it happens again, you’re going to be okay,” she shares. “It does give you incredible drive and no fear of failure.”

That mindset has defined her career as she has aged, and she encourages others to reflect on how mistakes or setbacks can be considered learning experiences.

GETTING REAL ABOUT MONEY

Financial resilience was another key part of Wainwright’s comeback. After Pets.com and her divorce, she found herself in a more uncertain financial place than she’d ever been. It changed how she thought about money – and security.

“There was fear,” she says. “I saw it around my parents’ friends – things happen, health things happen, work things happen,” shared Wainwright. “Some people figure out a way out of it and move forward, and some people just don’t. Some blows are harder to take when you get older.”

That awareness motivated her to rebuild with intention, prioritizing financial independence and creating a life that allowed her to give back. “I wanted to be in a position where I could live what I would consider a good life,” she shared. “And, also, a position where I could support others.”

RETIREMENT? NOT ON HER RADAR

Now in her late 60s, Wainwright still gets one question all the time: When are you going to retire? Her answer? Not anytime soon. “I think people assume that we don’t have a lot that we want to do, or a lot that we can do,” she shares. “But if people love working and if they love creating things through work, to retire feels like a death sentence.”

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