Turning Ideas into Billion Dollar Businesses (with Julie Wainwright) SB1703
The Stacking Benjamins Show
Joe Saul-Sehy and Josh ‘OG’ Bannerman, CFP
4.4 • 2K Ratings
🗓️ 2 July 2025
⏱️ 66 minutes
🧾️ Download transcript
Summary
What does it take to turn a bold idea into a billion-dollar brand? Julie Wainwright, founder of The RealReal, joins us to share how she did just that—after enduring some pretty public failures (hello, Pets.com). She talks about navigating the startup world, tackling ageism head-on, and why your past doesn’t define your future.
Julie’s story is packed with wisdom on risk-taking, confidence, and what it really means to build something new when everyone else is telling you no. From the boardroom to the resale boutique, she takes us through the emotional rollercoaster of entrepreneurship—plus a few secrets on why luxury goods are more than just a pretty label.
Also in the basement:
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We unpack Jason Zweig’s latest Wall Street Journal column on diversification and why it still matters (yes, even in this market).
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OG learns a Father’s Day lesson on the golf course (spoiler: not all swings are created equal).
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Doug manages to work in Margot Robbie. Again.
Whether you’re plotting your own business empire or just wondering how someone not only recovers from flaming sock puppet-level failure, but who THRIVES afterward, this episode delivers honest insight with a side of style.
FULL SHOW NOTES: https://www.stackingbenjamins.com/from-business-idea-to-execution-julie-wainwright-1703/
Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201
Enjoy!
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Transcript
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| 0:00.0 | Hello there, Peabody here. |
| 0:02.0 | And this is the Wayback Machine for traveling through time. |
| 0:05.0 | And this is my boy, Sherman. |
| 0:07.0 | Speak, Sherman. |
| 0:09.0 | Hello. |
| 0:10.0 | Good boy. |
| 0:11.0 | Live from Joe's Mom's Basement, it It's the stacking Benjamin show. |
| 0:34.3 | I'm Joe's mom's neighbor, Doug, and how do you take a good idea and turn it into a billion dollar business? |
| 0:35.9 | We'll tell you how, because we'll ask today's guest, the founder of the real real Julie Wainwright. Plus, in our headline, do you have too much in that one stock? You sure do. And so do some people way smarter than you. Although, I mean, don't get me wrong. We still think you're really, really smart. And don't worry, we'll help you find a way out. |
| 0:56.4 | And don't even ask, yes, it's already on the menu. |
| 0:59.9 | You're about to win a helping of my incredible trivia. |
| 1:03.8 | And now, two guys who believe your financial future is brighter than your phone screen at 2 a.m. |
| 1:09.5 | Seriously, turn it off. |
| 1:11.0 | It's Joe and O, Jha, Jha, Jha, Jee. |
| 1:16.5 | Hey there, Stackers, super happy. |
| 1:18.5 | You're here with us today. |
| 1:19.7 | Sit back and relax because you are in for some Wednesday, |
| 1:24.3 | goodness, or whatever day you happen to be listening. |
| 1:27.4 | Because if you've ever had an idea, |
| 1:29.3 | you want to make sure that that idea becomes much, much, much, much bigger than you ever imagined. |
| 1:36.1 | Well, as Doug so eloquently said, Julie Wainwright joining us today. Mr. O.G., how are you? |
| 1:43.0 | You're joining us today, as usual. Yes, I'm contractually obligated to join you today. Mr. OG, how are you? You're joining us today, as usual. Yes, I'm contractually |
... |
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