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EFR 885: How The RealReal Founder Turned Failure Into a $1 BILLION Luxury Brand with Julie Wainwright

Ever Forward Radio with Chase Chewning

Release Date: 07/14/2025

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This episode is brought to you by Timeline Nutrition and Pique Teas.

Julie Wainwright is the powerhouse founder behind The RealReal, the luxury resale juggernaut she launched at 53 after being publicly shamed for the failure of Pets.com. In this episode, Julie tells the full story—how she bounced back, took on Amazon by doing what they wouldn’t, and faced off against Chanel in a high-stakes industry lawsuit. She opens up about navigating sexism in boardrooms, creating value from secondhand fashion, and why the future belongs to bold founders, not safe CEOs.

Follow Julie @realrealjulie

Follow Chase @chase_chewning

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In this episode we discuss...

00:00 - Julie Wainwright Introduces The RealReal

00:35 - The Founder vs. CEO Mentality

03:00 - Raising $700M: A Story of Persistence

06:08 - Turning Around Berkeley Systems & Pets.com

09:03 - Why Founders Must Embrace Possibility, Not Logic

10:14 - PE vs. VC: Who Should You Trust With Your Startup

13:25 - Starting The RealReal at 53 After Total Rejection

16:04 - “Plan B Was Hell”: Yoga, Snakes & Arizona

18:42 - Why Amazon Would Never Compete in Luxury Resale

20:04 - The Boutique Experience That Sparked The RealReal

21:35 - Launching in 4 Months: Julie’s Execution Playbook

23:32 - Making Resale Cool: Hiring a Fashion Insider

25:43 - Keeping the Romance of Luxury Alive

27:21 - Luxury as Art: Why the RealReal Appeals Emotionally

29:01 - Monetizing Secondhand Luxury

30:54 - How Resale Changes Consumer Behavior

33:29 - Girl Math, Cartier Watches & Smart Shopping

35:15 - Why Resale Was So Hard Before The RealReal

37:01 - Chanel’s Vendetta Against The RealReal

38:28 - Neiman Marcus Deal Sabotaged by Chanel

40:26 - Chanel Lawsuit: Accusations & Counterclaims

41:36 - WWD Awards Night & Chanel's Petty Tactics

45:20 - Thugs at Her Door: When Things Got Physical

47:53 - Where She Stands with Chanel Today

48:22 - Why Julie Got Fired from The Company She Built

51:42 - The Boardroom Coup: What Really Happened

54:01 - Her Theory: Money, Power & Politics

56:10 - Business Advice for Small Business Owners

58:09 - How Julie Sets Quarterly Goals & Metrics

60:13 - Don’t Believe Your Own Press

63:39 - Ever Forward”

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