The following is an exclusive excerpt from The RealReal founder Julie Wainwright’s new book “Time to Get Real: How I Built a Billion-Dollar Business That Rocked the Fashion Industry,” available for pre-order here and on sale June 10, 2025. Reprinted by permission of BenBella Books, 2025. Copyright © 2025 by Julia Wainwright.

I sat down with my three dogs — Betty, Louie, and Mo — on either side of me, a glass of wine in my hand, and stared out to Angel Island and Raccoon Strait as the fog rolled in over the Bay. I was looking for my next gig and had just come from a meeting with a tech recruiter, who I’ll call Mr. Cupid. To put it mildly, I got no love from Mr. Cupid. I asked him why every opportunity that came my way was horrible, simply the dregs. Each company was a turnaround. The quality of their teams was poor, and the quality of the venture capitalists investing in them was just as bad. He looked me squarely in the eyes and said something like, “You are only as good as your last gig, and your last gig was horrible. You are close to being unemployable in the Valley.” I was so shocked at his candor that I don’t even remember exactly how I responded. All I remember saying was that Pets.com was years ago, and he said, “And what success have you had since then?”

I don’t remember how I got home, either. Clearly, I drove myself because my car was in the carport when I went out the next morning, and Uber hadn’t been invented yet.

I could not escape what had happened nearly ten years before. On one single day, everything changed. On that day, I shut down Pets.com.

Mr. Cupid made it clear that my career in Silicon Valley was over. On some level, he said, I was clearly deluding myself to think I could still get a good CEO position in the industry. 

He set me straight, it was not going to happen. I might be offered a turnaround. He said what I knew to be true. I didn’t want it to be so, but he verbalized my reality and reinforced my fears. The clarity smacked me in the face. I could not waste more time and burn through more money. I had to do something different.

I simply couldn’t go on more interviews for positions that would suck my soul out of my body. I knew I was done with that phase of my life. But where to go next? I had tremendous energy, was extremely healthy, had deep experience, knew how to get the most important things done, and hire great teams. Yet none of what I had to offer seemed to be of value to early-stage companies or, more significantly, to their investors.

As is the case for many women, my career progression in technology positions had always been hard. The only reason I had risen to the level of CEO was because I had joined a company that was failing, and I developed a plan to turn that company around — and it worked.

That company was the software innovator Berkeley Systems. If my plan hadn’t worked, I wouldn’t have had any future CEO opportunities. But it did work, and I happily took my next job as the CEO of Reel.com, the first site to rent movies online. That business had a successful outcome for investors, and I was offered my next CEO opportunity, to be CEO of Pets.com, the online purveyors of pet supplies. And that is when the music stopped.

I called my friend Kathryn later that Friday night. Could she hike Mount Tam with me tomorrow? I really needed to talk to her. I needed her perspective. Kathryn had worked with me at Berkeley Systems and Pets.com. She knew me well, and I knew she would be honest. We met in the parking lot by the horse stables at a trailhead in Mount Tamalpais State Park in Marin County, not far from my house on Belvedere Island. The air was crisp, and the hike was strenuous and straight up. But the payoff was worth it. The views at the top were of San Francisco, the Golden Gate Bridge, Sausalito, Tiburon, San Rafael, and the Richmond–San Rafael Bridge.

“So, what choices do you have?” Kathryn asked as we headed up the trail.

“Start my own company or move to Arizona and sell real estate and become a yoga instructor.”

“You hate yoga.”

“Hate is a strong word. It just feels like a cult.”

“Do you have any ideas for a new business?”

“Nothing,” I told her.

“I know you can start your own company. You’re a good leader. You can do it. The industry is brutal to women. So what! You have never let that stop you before. I know it can be odd and isolating being the only woman in the room. I know when we fail as women, we fall further and beat ourselves up longer. I also know how you run and build companies. You can do this.”

“I guess I’ll have to figure it out. Or I won’t. But I have to try. At some point, I am going to run out of money.”

“Yep, that is a concern. Money is important,” she said. “The divorce hurt, I know. Giving away half of what you worked for feels wrong, especially when your husband didn’t financially contribute. I’ve been there, I know.”

I appreciated her sympathy and understanding. It’s what I needed to hear.

“Money is a big concern. I’ll have to give myself a timeline for success.” As we rounded a curve in the path, I added, “I need to go home and develop a framework before I take some action. I did the math. I’m going to run out of money in less than two years. That is a long time on some level. And really scary on another level. I don’t have the luxury of finding my way toward success. I am going to have to nail it.”

“You need to try,” she said reassuringly.

I could not imagine that, within the next two years, I would be starting on the journey of a lifetime. All I knew is that I couldn’t keep doing what I had been doing.

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