Check Out These Highlights:
Caroline Pennington spent 15 years climbing the corporate ladder, placing C-suite executives and mastering the art of communication on LinkedIn. But when the work stopped feeling meaningful, she listened to the voice in her head saying, “You were made for more.” In this episode, Caroline shares how she launched a wine product during the pandemic, built a powerful personal brand from scratch, and turned her skills as a recruiter into a thriving LinkedIn marketing agency.
We talk about her shift from side hustler to full-time entrepreneur, why consistency on LinkedIn pays off, and how she uses podcasting and visibility to grow her network and impact. Caroline also opens up about handling skeptics, taking imperfect action, and why you should never wait for permission to start.
About Caroline Pennington:
Caroline Pennington is a LinkedIn marketing expert, founder of The Feminine Founder Podcast, and creator of ChilledVino. She helps female entrepreneurs and executives build personal brands that get noticed, while keeping it real, strategic, and fun.
Connect with Caroline:
🌐 Website: https://femininefounder.com/
💼 LinkedIn: https://www.linkedin.com/in/caroline-pennington/
📸 Instagram: https://www.instagram.com/cpennington55/
Stalk Me Online!
🔗 LinkTree: https://linktr.ee/tobymyles_copywriting
🎁 Free Gift: The Nashville Method: 5-Day Storytelling Mini-Course
Subscribe to Her Origin Story on your favorite platform. New episodes every week with real, raw stories about the moments that started it all.
Episode Notes Footer:
Her Origin Story is produced by Toby Myles Copywriting, and podcast editor Ilorah Dela Cruz
All content © 2025 Toby Myles. All rights reserved.
Popular Podcasts
NFL Daily with Gregg Rosenthal
Gregg Rosenthal and a rotating crew of elite NFL Media co-hosts, including Patrick Claybon, Colleen Wolfe, Steve Wyche, Nick Shook and Jourdan Rodrigue of The Athletic get you caught up daily on all the NFL news and analysis you need to be smarter and funnier than your friends.
On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
Dateline NBC
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com