60-Year-Old Entrepreneur Makes A Remarkable Comeback By Pursuing Her Dream Job

When we think about people in their 50’s and 60’s, we most often envision folks who are at the apex of working life. They are at the peak of their success, and perhaps putting their seatbacks into the upright position for the long final approach to a soft landing in retirement.

While that’s still a common scenario, things have changed. More and more Americans are entering a dramatic second career act between 50 and 65. They are starting new businesses – either by choice or because entrepreneurship is their best or only work option.

A CNBC and Survey Monkey survey of more than 2000 small-business owners found that nearly 30 percent had launched their small enterprise between the ages of 55 and 64. Another 22 percent were 65 and older.

These late-blooming entrepreneurs, like their younger peers – meet with varying degrees of success. Some struggle, some make a nice living. And some, like Julie Wainwright, hit it out of the park and across the parking lot.

Wainwright’s world came crashing down in 2000. Her marriage fell apart and Pets.com, the company she helped raise from startup to tech bubble darling was forced out of business. In the wake of that double catastrophe, Wainwright struggled to find personal and professional satisfaction. The life-long employee, who was in her late 40’s, couldn’t get a decent job offer.

After several years adrift, Wainwright came to a pivotal realization. No one was going to give a dream job. She had to create that job for herself. One day, while shopping with a friend, Wainwright came up with an idea for that new gig.

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Wainwright’s gal pal was a fan of both high fashion and bargains. She would spend hours rooting through the second-hand racks in fashionable boutiques.  Wainwright’s friend explained that she would never shop for fashion items at a consignment shop or on eBay because there are too many fake designer items offered in those places. Trust in the vendor, the veteran shopper explained, was critical when hunting for used glamour items.

In short order, Wainwright’s e-commerce savvy and experience kicked in. In 2006, she launched TheRealReal.com, a shopping site that offers authenticated second-hand luxury goods on assignment. The first batch of inventory was 60 pieces from Wainwright’s own closet.

TheRealReal.com had $10 million in sales in its first year, according to Wainwright. It’s expected to do $500 million in revenue this year and has 950 employees. Among the brands found on the RealReal are Louis Vuitton, Hermès, Cartier, Van Cleef & Arpels, and Rolex. The RealReal provides free in-home pickup, authentication of the items, and shipping. Consignors earn up to 70 percent of the sale price.

Wainwright’s current success was hard won. Despite her tech biz cred, she started her company with strikes against her, in the eyes of Silicon Valley. She was a middle-aged woman who was at the helm when Pets.com failed.

Undaunted, Wainwright did her best in countless meetings with male venture capitalists in their 20’s and 30’s; guys whose idea of luxury goods didn’t go much beyond Teslas and Ferraris. Finally, she met a woman VC who understood both her and her vision. The RealReal.com has received $173 million in venture capital investment in seven rounds of funding. Wainwright, who is now 60, hopes to take the company public at some point.

Julie Wainwright’s story is truly inspiring. If you are facing a late career crisis or looking for extra income in retirement, finding a job isn’t the only answer. Look within. Inventory your passions, skills and experience. I’d bet anything that you’ll find the tools to create your own dream job – one that is both psychologically and financially rewarding.

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Cover Image: The RealReal

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