S2 Ep65: How to Know When It’s Time to Leave, Pivot, or Start the Thing You Can’t Stop Thinking About
Well Said with Syd
well said syd
4.9 • 714 Ratings
🗓️ 3 November 2025
⏱️ 60 minutes
🧾️ Download transcript
Summary
Are you wondering if your idea, your brand, or your next chapter is actually worth the leap?
In this episode, Syd sits down with one of her real-life mentors, Amber McMillan - mom of two, longtime corporate leader, and now co-founder & CEO of a fast-growing aesthetics brand, CLEO Skin + Laser, to talk honestly about what it really looks like to walk away from a stable career and build something of your own.
Amber spent 20+ years in health, fitness, and wellness before making the jump into entrepreneurship and opening multiple locations in the clinical skincare space. Together, Syd and Amber unpack how you know it’s time to go, what makes a brand worth your time and energy, and how to build something that actually delivers results—not just a pretty logo.
In this episode, you’ll learn:
- The signs it’s time to leave, pivot, or finally start the thing you can’t stop thinking about
- How to tell the difference between a “cute idea” and a real opportunity
- What makes a brand truly work (and why most businesses never get there)
- How Amber went from corporate SVP to multi-location founder without sacrificing her family or sanity
- Why evidence-based results matter more than hype in beauty, wellness, and skincare
- What founders really mean when they talk about “hustle” (and how to do it without burning out)
- How to think about wealth, work, and your next chapter in a way that actually feels aligned
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Transcript
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| 0:00.0 | Guys, my hair looks crazy today, but we're on the mic and it doesn't matter. Okay. I'm very excited. |
| 0:05.3 | This episode is going to be incredible. I have someone very special here who actually is one of my |
| 0:09.7 | mentors and we've worked together and now we're working together for a second time and we can |
| 0:15.0 | actually openly talk about it, which is so exciting. But today is going to be a little bit about |
| 0:19.7 | like founder mentorship, a lot about |
| 0:23.6 | founder energy, though, like female founder, why start a business? What does that even look like? |
| 0:28.3 | How would you even go about doing it? How do you know that your business is actually going to |
| 0:33.0 | take off or succeed? A little bit of a trick question there. And how do you do that all while |
| 0:37.3 | being a woman, |
| 0:38.3 | a mom, having change, etc.? Amber McMillan is here. |
| 0:59.5 | She's the CEO founder and co-CEO of Cleo Skin and Laser. |
| 1:04.0 | Did I give you the right title? |
| 1:05.4 | Co-founder and CEO. |
| 1:06.4 | Oh, I just said it backwards. |
| 1:08.1 | That's why it sounded funny. |
| 1:09.2 | I'm like, why did that sound funny? |
| 1:10.7 | But yeah, hi, welcome. Hi, backwards. That's why it sounded funny. I'm like, why did that sound funny? But yeah, hi, welcome. |
| 1:12.0 | Hi, thanks so much. |
| 1:28.4 | You're freaking fab, by the way. Your hair looks good. Your outfit is slate, all black, everything. Girl. Girl. Takes a lot. Just getting the shower in these days. Quit it. Tell us like a little elevator, like kind of pitch of who you are. |
| 1:29.3 | I know who you are. |
| 1:30.0 | That's the hard part. |
| 1:29.3 | It's like, I can intro you all day but i want you to speak to yourself well i am |
... |
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