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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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When I sat down with Lauren Stephens of Dudley Stephens, what struck me most was how many beginnings sit inside her story: the career she thought she’d have, the infertility journey that shifted her path, and the unexpected moment she realized she had an idea worth betting on.
In this conversation, Lauren shares how she launched a family business before she felt ready, and why signing a formal agreement early on became one of the smartest decisions they made.
Lauren also opens up about the parts no one prepares you for: managing people for the first time, staying steady when customers or employees aren’t happy, and learning where to draw boundaries so the business doesn’t swallow the rest of your life.
What You’ll Hear
- The moment life forced her to rethink everything (00:00)
- Bringing her mom and sister into the idea (01:21)
- Why clear roles and ownership matter (11:32)
- How cozy-at-home culture fueled unexpected growth (20:07)
- Hiring lessons and learning to lead (24:51)
- Different phases of motherhood and how evolving careers (36:24)
Lauren’s story is about more than entrepreneurship. It’s about listening to the quiet nudge that tells you to begin, trusting your own pace, and allowing the hard seasons to shape the ones that follow. If you’ve ever wondered whether you’re “ready” to start something new, this one is for you.
You can watch this interview on YouTube: https://youtu.be/A_0BsOeWAno
For a full transcript and more, check out our blog post: https://www.lindsaycz.com/show-notes/lauren-dudley-stephens-26
Check out more from Lauren and from Dudley Stephens:
Visit www.dudley-stephens.com. Take advantage of 30% off sitewide until December 2, 2025 using the code HOLIDAY30.
Check out the new Manchester pullover that Lauren wore during the episode.
Keep up with the latest on Instagram: @dudley_stephens
Connect with Lauren on Instagram: @laurendudleystephens
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