Julie Wainwright has taken two companies public, an incredible feat by any standard. Yet in her new memoir, Time to Get Real, she offers readers something even more valuable than a kind of victory lap: a look at the messy realities of leadership. Wainwright shares tough truths that many high-achieving CEOs can relate to but rarely discuss publicly, including the aftermath of what many would consider her first major setback, which was shutting down Pets.com during the 2000 market crash.
If you’re of a certain age, you definitely remember it. The online pet supplies startup had become instantly recognizable thanks to its memorable sock puppet mascot and catchy slogan, “Because pets can’t drive.” But what seemed like just a fleeting moment in the dot-com bubble’s burst would cast a shadow over Wainwright’s career for nearly a decade. “When I would talk to recruiters, it was like, ‘No one’s going to hire you anymore,’” Wainwright said in an interview with this editor earlier this week.
It came as a shock, given that Wainwright’s career trajectory initially seemed unstoppable. After cutting her teeth at Clorox, she rose through tech companies in the ‘90s when female leadership in the sector was exceedingly rare. As CEO of Berkeley Systems and later the online video store Reel.com, she worked “tons of hours” but was happy and, by her telling, succeeding, including growing Reel.com’s revenue from $3 million to $25 million — a time during which the company was sold to Hollywood Video. “I just operated better without a boss,” she said.
Then came the collapse that would have permanently derailed many careers. In 2000, Wainwright took Pets.com public, only to shut it down later that same year during the dot-com bubble burst. The professional blow was exacerbated by a personal one: she says that on the very same day she informed employees of the company’s closure, her husband asked for a divorce.
“My work is gone, I’m getting a divorce, and I don’t have children,” Wainwright, then 42, recalls thinking as she faced what felt like total life collapse. Making matters worse, the media coverage was “incredibly negative and intrusive,” to the point that she says days after the company’s closure, reporters showed up at her doorstep.
Wainwright describes what followed as a kind of long winter, where she was only offered roles leading turnaround efforts at failing companies. But that crossroads led to a remarkable second act. In 2010, she founded The RealReal, helping in the process to pioneer the luxury consignment market online. Like a lot of founders, Wainwright first set up the company out of her own home, but it soon outgrew her living room, and today, it processes many hundreds of thousands of different luxury items each month that it aims to sell within 90 days out of its more than 1.2 million square feet of warehouse space. It’s also publicly traded; in her second trip to Wall Street, in 2019, Wainwright took the outfit through the traditional IPO process.
Unfortunately, this comeback has its own harsh chapter. In 2022, Wainwright was abruptly pushed out of The RealReal by board members she had recommended – another twist she doesn’t shy away from sharing. Instead, she names names in the book, and earlier this week, she described the move as a “power play” by an investor who “didn’t get his money out of the company and thought he could run the company better.”
Wainwright — who fully supports the company’s current CEO (she was the company’s first hire) — is still miffed. She noted in conversation that “no founder is ever going to say they need to be shot and removed,” and it’s that honestly that makes the book – and Wainwright herself — so refreshing. In the corporate world, where people often spin narratives to make themselves look bulletproof, Wainwright is a straight shooter. If she doesn’t like something, she isn’t going to hold her punches. If someone spins the story differently than she sees it, she’ll call it out. Where she messes up, she says so.
Even better about this memoir — in this reader’s opinion — is Wainwright’s ability to offer not just personal revelations but practical wisdom. She walks readers through her decision to bonus her sales staff a certain way, and shares her learnings about a leadership-evaluation quadrant she gleaned from McKinsey executives, including the realization she had hired one of the worst types: a “dumb aggressive,” meaning, in her words, someone whose “need to bully and coerce and to be on top supersede their abilities.”
There’s also an interesting new chapter unfolding. Wainwright is continuing her entrepreneurial journey with Ahara, a nutrition company that’s developing personalized dietary recommendations based on genetics and individual needs.
You can find our full conversation here, via TechCrunch’s StrictlyVC Download podcast. In the meantime, if you’re interested in a read that’s almost equal parts memoir and manual, offering founders something much more worthwhile than idealized success stories, you can pick up the book here.
Said Wainwright when we spoke, “I personally wrote it for entrepreneurs to give them a realistic view and hopefully inspire them and, you know, maybe they’ll think twice and not make the mistakes I made.”
