HerMoney with Jean Chatzky
Episode: Your Money Map Replay: Julie Wainwright on Reinvention, Risk, and Building The RealReal After 50
Date: November 28, 2025
Guest: Julie Wainwright, founder of The RealReal
Episode Overview
This episode explores the remarkable story of Julie Wainwright, who, after suffering a public and personal series of setbacks—including the high-profile collapse of Pets.com and a divorce at age 42—reinvented herself and went on to build The RealReal, a billion-dollar luxury consignment platform, in her 50s. Host Jean Chatzky and Julie dive into the messy, unfiltered truth of entrepreneurship, the reality of risk-taking later in life, ageism and gender bias, and the value of resilience. Julie shares practical insights and advice from her new book, Time to Get Real, and reflects candidly on leadership, boardroom politics, and staying purpose-driven amid adversity.
Key Discussion Points & Insights
1. Moving Past Failure and Personal Setbacks
- Julie recounts the Pets.com experience as a major, career-defining failure (07:55).
- Shutting down Pets.com despite being in a net positive position; the company was an early victim and symbol of the dot-com bust.
- The challenge of becoming unemployable despite previous successes:
“I had one failure and it was incredibly hard to get another job in tech... It actually sort of was like a dark cloud around me.” — Julie Wainwright (09:10)
- Suffered multiple setbacks concurrently: public scrutiny, divorce at 42, her mother's death.
- Julie describes the cumulative pain: “I let those two events define me and felt terrible about it. …It altered my personality because I became more introverted.” (10:36)
- Coping strategies: “Being around creative people, artists… Being out in nature helped. And to be honest, time helped. …I got tired of being in a funk, you know?” (11:53)
2. Reinvention After 50: Launching The RealReal
- The genesis of The RealReal: Launched from a gritty, shoestring operation, renting a tiny warehouse, handling everything herself.
- “You walked in. The entry level had, like—It felt like plastic carpet. Like, it crunched like you’re walking on cereal… I put black plastic bags… on the windows…” (13:08)
- Immediate market validation:
- “Our first sale, we sold everything out really quickly and did $30,000 the first day. …I knew it right away.” (14:10)
3. Ageism, Sexism, and Venture Capital
- Overcoming bias as a woman over 50 with a well-known business failure in her background.
- “I’m not sure what got me the most. The fact that a lot of the people I was meeting with, I was old enough to be their mother, or the fact that I had had pets.com in my background. Probably the combo was fairly detrimental.” (15:36)
- Early funding difficulties; first serious investor was a woman who understood the business (16:10).
- Advice for women starting businesses later in life:
- “You have more knowledge… You’re much more strategic, you’re much more to the point. …Maturity is really great. …If you know what you want to do and you’ve got the energy to do it and the inclination, age shouldn’t come into it.” (17:02)
4. Leadership Lessons and Boardroom Politics
- Board misalignment and consequences: After The RealReal went public, Julie appointed board members lacking entrepreneurial and high-growth experience, creating a disconnect (22:40).
- “It really… we were speaking a different language.”
- COVID-19 exacerbated these issues, leading to her eventual exit as CEO.
- On being fired: “Oh, it was absolutely devastating. …I didn’t help myself because people just don’t like to see a woman get mad and have anger. And I did. I lost it in a board meeting.” (25:52)
- “I took it from an idea in my kitchen to over a billion dollars, and I took it public as one of the—I think I was the 23rd woman ever to take a company public…” (26:42)
5. Thoughts on Retirement and Calculated Risk
- Julie rejects the conventional idea of retirement:
“It’s like something from the 50s. …Retired to what? The truth is, if you’re curious and you’re engaged in life and you love business…I don’t really understand it.” (27:54) - Going 'all in' financially: She emptied out her 401(k) to fund The RealReal, a leap typically associated with much younger founders.
- “I took it down to like $50,000 to take that money out… I understood that I had a supply problem… and that this could be a huge hit.” (29:50)
- Not risk-blind, but risk-calculating: “It didn’t feel risky. It felt like a calculated risk. When I look back at it, it was pretty risky. But it worked out.” (31:19)
6. What’s Next and Giving Back
- Julie now sits on boards, mentors mostly female entrepreneurs, and invests via various VC funds (32:13).
- Finds fulfillment in helping others: “Every single day I meet with entrepreneurs, almost all females, and I’m helping them or coaching them, talking to them…” (32:32)
7. Parting Advice for Women Entrepreneurs
- Top Three Pieces of Advice: (33:44)
- “Give yourself a lot of rope. Give yourself some grace, because things will go right and wrong. …Do not beat yourself up, because other people will do that.”
- “Be careful the people you hire. Make sure you have value sync. …Values and what you hold, its value and experience are really important.”
- “It’s not over till it’s over. …If you fail… you’ve got time until you’re in the grave. You’ve got time to try and try again.”
- Bonus: “I just hope people laugh a lot when they make mistakes because honestly, that humor gets you through so many things…” (34:25)
- Memorable anecdote: A customer call about the price of used shoes, finding humor even in business absurdities (34:36).
Notable Quotes & Memorable Moments
-
“I had one failure and it was incredibly hard to get another job in tech... It actually sort of was like a dark cloud around me.”
— Julie Wainwright (09:10) -
“Being around creative people, artists… Being out in nature helped. And to be honest, time helped.”
— Julie Wainwright (11:53) -
“Our first sale, we sold everything out really quickly and did $30,000 the first day. …I knew it right away.”
— Julie Wainwright (14:10) -
“If you know what you want to do and you’ve got the energy to do it and the inclination, age shouldn’t come into it.”
— Julie Wainwright (17:52) -
“I took it from an idea in my kitchen to over a billion dollars, and I took it public as one of the…I think I was the 23rd woman ever to take a company public and created a new industry and raised the awareness of sustainability.”
— Julie Wainwright (26:42) -
“Retired to what? The truth is, if you’re curious and you’re engaged in life and you love business… I don’t really understand it.”
— Julie Wainwright (27:54) -
“Give yourself some grace, because things will go right and wrong. …Do not beat yourself up, because other people will do that.”
— Julie Wainwright (33:44) -
“It’s not over till it’s over. …If you fail… you’ve got time until you’re in the grave. You’ve got time to try and try again.”
— Julie Wainwright (34:22)
Key Timestamps
- 07:55 – Julie reflects on the fall of Pets.com and public shaming
- 10:36 – Discusses compounding personal crises and journey back to self
- 13:05 – Launching The RealReal out of a gritty, makeshift warehouse
- 15:36 – Confronting ageism, sexism, and bias in the venture capital world
- 17:02 – Advantages of entrepreneurship in one’s 50s
- 22:40 – Leadership mistakes and board misalignment post-IPO
- 25:52 – Getting fired from her own company and its impact
- 27:54 – Rejecting retirement and staying passionate about business
- 29:50 – The decision to risk her 401(k) to fund her dream
- 32:13 – Mentoring, investing, and finding new purpose
- 33:44 – Julie’s top advice for women entrepreneurs
Resources and Further Information
- Julie’s book: Time to Get Real (Available at Barnes & Noble, Amazon)
- Instagram: @realrealjulie
- Email/Investment Contact: julie@shaktivc.com
- LIMRA Alliance for Lifetime Income: protectedincome.org
Tone and Takeaways
Frank, funny, and fiercely practical, this conversation with Julie Wainwright is a masterclass in resilience, late-in-life reinvention, and the power of calculated risk. Julie dispels myths about age and entrepreneurship, shares invaluable leadership wisdom from her highest highs and lowest lows, and encourages women to give themselves permission to evolve, make mistakes, and keep moving forward—no matter when or how often life knocks them down.