Your Money Map Replay: Julie Wainwright on Reinvention, Risk, and Building The RealReal After 50

HerMoney with Jean Chatzky

Jean Chatzky Her Money

Investing, Business

4.8 • 1.3K Ratings

🗓️ 28 November 2025

⏱️ 36 minutes

🔗️ Recording | iTunes | RSS

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Summary

In this powerful and inspiring episode of Your Money Map, Jean Chatzky sits down with entrepreneur and author Julie Wainwright, founder of The RealReal, to talk about failure, reinvention, and why it’s never too late to bet on yourself. She shares candid stories from her new book, Time to Get Real: How I Built a Billion Dollar Business that Rocked the Fashion Industry, and the hard-won lessons she learned about leadership, raising capital as a woman over 50, and taking calculated risks — including the moment she emptied her 401(k) to fund her vision. Topics We Cover: How Julie rebuilt her career after Pets.com The surprising advantages of launching a business later in life Facing ageism and gender bias in venture capital Why she bet her retirement savings on herself The messy truths behind entrepreneurship Advice for women starting over at any age 👉 Resources & Links: 🔗 Learn more about retirement income at ProtectedIncome.org 🔗 Sign up for the newsletter: protectedincome.org/subscribe Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	Have you ever wondered what a sandwich sounds like?
0:03.0	Not much to it is there?
0:06.0	Unless of course it's a Walker's sandwich.
0:10.0	Mmm, that is good.
0:13.0	Now that's what Asani should sound like.
0:15.0	Go all crisp in with walkers.
0:18.0	Delicious.
0:20.0	There's many good things about it. If you're healthy and have high energy, with walkers. Delicious.
0:23.4	There's many good things about it.
0:30.6	If you're healthy and have high energy, which I was and am still, you can let most of the things that might rattle you in your 20s or 30s or even 40s slip away.
0:35.8	So I would say you have more knowledge. You know, you're not
0:39.5	dealing with roller coaster life. You know, you understand how to maneuver through the good
0:44.9	and the bad in life. Chances are you're much more strategic. You're much more to the point.
0:53.0	Hey, everyone. welcome to Her Money.
0:54.8	I'm Gene Chatsky.
0:56.0	If you have ever hit a major bump in your career or your life and thought, well,
1:00.7	that's it, I'm done.
1:02.4	This episode is for you.
1:05.0	Julie Wainwright, my guest on a recent episode of Your Money Map, the show I host for
1:10.8	Limra's Alliance for Lifetime Income,
1:13.6	was once told she was unemployable at age 52.
1:18.4	And yet, she went on to launch The Real Real, a luxury consignment platform that didn't just
	...

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