299: From fit-in to stand-out: How midlife entrepreneurs can build a personal brand with soul - with Judy Winslow
- S10E299
- 47:34
- July 16th 2025
In this episode of Crank The 3rd, we dive into what it really means to stand out in your 50s and beyond.
Host Trevor Young sits down with Judy Winslow, founder of Unforgettable Brands, to explore how experienced professionals and entrepreneurs can build a soulful, authentic, and unforgettable personal brand in the so-called “third chapter” of their careers.
Judy shares her powerful personal story - from facing depression and feeling out of place as a young woman, to discovering her purpose through creativity, business, and brand strategy.
Together, Trevor and Judy unpack the importance of embracing your unique twist, reconnecting with your values, and getting comfortable with being a “unicorn”—someone who dares to be different in a world that often rewards blending in.
You’ll get practical tips on how to bring out your individuality, what it means to infuse your brand with real soul, and why your past experiences are the raw material for your finest work.
Judy also pulls back the curtain on her process for helping clients get braver and bolder, whether you’re building a team, scaling your business, or preparing for a big-stage moment like a TEDx talk.
If you’re ready to stop playing small, own your story, and amplify your impact, this conversation is packed with wisdom, humour, and actionable steps.
Let’s get started!
QUOTABLE QUOTE FROM JUDY:
“No one speaks quite like you. No one articulates quite like you. No one sees your industry quite like you, nor do they have the experience. So… just being you—that's so fabulous.”
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Visit Judy's website - https://unforgettablebrands.com/
Connect with Trevor on LinkedIn - https://www.linkedin.com/in/trevoryoung
EARN THE RIGHT with Trevor Young
EARN THE RIGHT is your audio platform for reputation-based authority building — turning credibility into recognition, and recognition into opportunity.
Hosted by Trevor Young, it’s for credible founders, experts, and solo practitioners who’ve earned their stripes and are ready to amplify their voice with integrity.
Across four distinct (but inter-related) tracks —
- Crank The 3rd
- Pocket PR Essentials
- In The Arena
- From The Trenches
— you’ll get the ideas, stories, and strategies that help you cut through the noise and build lasting authority.
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1️⃣ CRANK THE 3RD
CRANK THE 3RD celebrates the Wisdom Economy — a world where depth, perspective, and lived experience fuel what’s next. It features conversations with inspiring midlife founders and professionals who are turning decades of know-how into opportunity: building meaningful ventures, shaping ideas, and designing work that matters.
2️⃣ POCKET PR ESSENTIALS
POCKET PR ESSENTIALS delivers short, sharp coaching sessions on building visibility and recognition — without the hype. Presented by Trevor Young, this audio playbook helps credible founders and solo professionals master PR, content, and digital communication to raise their profile and grow authority in a way that’s strategic, sustainable, and respectful.
3️⃣ IN THE ARENA
IN THE ARENA is Trevor Young’s unfiltered take on earning authority in real time — sharp, strategic riffs on content, credibility, connection, and the courage to keep showing up. Essential listening for entrepreneurs and professionals navigating the intersection of creativity, communication, and personal brand authority.
4️⃣ FROM THE TRENCHES
FROM THE TRENCHES presents deep-dive interviews with PR practitioners, content strategists, and digital communications experts that explore how reputation and influence are built today. Hosted by Trevor Young, this track shares grounded insights, hard-won lessons, and practical wisdom from those shaping credible marketing communications in the modern reputation economy.
You've put in the hard yards, now it's time to capitalise!
Earn attention. Build authority. Stay human.
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