The Caroline Pennington Show

Hosted by Caroline Pennington

Business Entrepreneurship Education

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Episodes

183

Latest episode

Jun 2026

Language

EN-US

About the show

Heyyyyy & welcome to The Caroline Pennington Show! I’m your host Caroline, former executive recruiter turned Digital Marketing Expert OBSESSED with helping entrepreneurs to start, grow and scale their personal brand & business online. I have a passion for empowering & supporting fellow entrepreneurs. On this podcast, you’ll hear from fellow business owners sharing their stories and unpacking exactly how they did it in their business because we believe that as curious & ambitious human beings we can ALL learn from one another and to be inspired! Every week you'll hear from entrepreneurs and workplace experts and no matter the size of your organization- you’ll gain insight and knowledge to help support you in your journey too! So happy you’re here! Now, let’s dive in!

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60 recent

June 16, 2026Episode 18431 min

184: {Interview} Growing and Scaling a Niche Business with Jess Loske

Text me!Today I'm sitting down with the co-Founder of Midwest Barrel Co. Jess Loseke. She shares her entrepreneurial journey in the whiskey barrel industry, highlighting the challenges of scaling a niche business, the importance of mindset, and leadership insights. Listen to exactly how how her team navigates international logistics, tech innovations, and why building a strong company culture is crucial.Connect further with Jess HERE and more on Midwest Barrel Co. HERESupport the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

June 9, 2026Episode 1832 min

183: {Solo} Want to start a podcast?

Text me!Want to start a podcast, but have no clue where to start? Do it! Do it not ready, do it scared, do it anyways. I had no clue what I was doing when this journey began 3.5 years ago and am forever grateful to each and every one of you who tune in each week. Thank you, I appreciate you more than you know! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

June 2, 2026Episode 1824 min

182: {Sassy Solo} The Power of Givers Gain

Text me!Tired of spinning your wheels trying to grow your business? I've been there too and know you are not alone. In today's shorty solo, I'm popping off about what has worked best for me in business and hope it's helpful! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

May 26, 2026Episode 1816 min

181: {Sassy Solo} Comparison is Truly the Thief of Joy

Text me!Comparison is the thief of joy. Here’s why you should stop comparing yourself to others and focus on your own journey. 👉 Share this with someone who needs this reminder! We all have our unique paths. It’s easy to look at others and feel like we’re falling behind, but remember: you don't see the full picture of their journey. Every business owner, mom, or hobbyist started somewhere. Just like them, you’re in a process of growth. I’ve been there—feeling like I wasn’t enough, watching others soar while I struggled with crickets on my posts. But every step counts. Instead of comparing, focus on your progress. Ask yourself: what’s one small thing I can improve today? Comparison can lead to quitting, but I’m here to keep pushing forward until I reach my goals. Remember: you’re not alone in this journey. Let’s celebrate our unique paths! Still figuring it out? You’re not alone. Subscribe for more insights! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

May 19, 2026Episode 18018 min

180: {Interview} 5 Key Strategies to Simplify and Scale Your Online Business with Katelyn Hamilton

Text me!In this insightful interview, Caitlin Hamilton shares her journey from corporate marketing to becoming a successful business coach and entrepreneur. She discusses common challenges faced by high-achieving women in online business, the importance of simplifying systems, and strategies for scaling while maintaining work-life harmony. If you are an entrepreneur and know that you need to implement systems in your business to scale, this one is for you! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

May 12, 2026Episode 1796 min

179: {Sassy Solo} Be okay sucking when you first start out

Text me!Today I'm sharing my journey of starting a podcast from scratch, emphasizing that initial struggles are normal and encouraging perseverance. We talk about the importance of consistency, learning from mistakes, and staying true to your passion despite negativity. Because let's be real, no one is a superstar when they start something new or are learning a new skill. You have to put the reps in no matter what you are trying to achieve!Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

May 5, 2026Episode 1783 min

178: {Sassy Solo} Stop Doom Scrolling and Start Creating Content

Text me!In today's episode, I'm popping off about a topic that is near and dear to my heart. And that is: stop doom scrolling and start creating. You never know what can happen and creating content is the BEST thing you can do for your personal brand and/or business. It supercharges the know, like & trust factor and the sky is truly the limit. So next time you are sitting there doom scrolling, think of me popping off in this episode. Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

April 28, 2026Episode 17714 min

177: {Podcast LIVE} Breaking in the New Beaufort Digital Corridor Podcast Live Studio

Text me!In this engaging interview, Sasha Horne and I sit down to break in the BDC live podcast studio. I share my journey from corporate recruiting to podcasting, my love for the Lowcountry, and insights into building a successful podcast and community in Beaufort. Discover tips for aspiring podcasters, the vibrant local festivals, and how to connect with other inspiring entrepreneurs.PS: This was the very FIRST one, but stay tuned for more! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

April 21, 2026Episode 1762 min

176: {Solo} Thank YOU for listening

Text me!In today's episode, I just wanted to pop in here and say a HUGE thank you to each and every one of you who listen and support the show. Your support means everything to me and I appreciate you more than you know! Support the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE

April 14, 2026Episode 17521 min

175: {Interview} Unlocking AI for Small Business Success: Practical Strategies with Alane Boyd

Text me!In this episode, Alane Boyd shares her expertise on AI and automation, revealing how small businesses can leverage AI agents to save time, increase efficiency, and scale their operations. She discusses practical tools, workflows, and upcoming workshops to help entrepreneurs harness AI effectively.We talk all things: AI agent automation for small businessesPractical AI tools and workflowsUpcoming AI workshops and trainingHow AI saves time and increases efficiencyMore on her Claude Co-Work and AI Cohort HERE and use code CP10 for 10% off!Connect further with Alane on LinkedIn HERE or on her website HERESupport the showLINKS TO FREEBIES BELOW: WEEKLY NEWSLETTER where I share all the tips and tricks on how to grow organically online HERE If you are interested in sponsoring the show, send me a DMABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help women to start, grow and scale their personal brand and business online through social media. In 2021 I launched ChilledVino, my patented wine product and in 2023 I launched The Feminine Founder Podcast and in 2025 I launched my Digital Marketing Agency called Feminine Founder Marketing. I live in South Carolina with my husband Gary and 2 Weimrarners, Zena & Zara. This podcast is a supportive and inclusive community where I interview and bring women together that are fellow entrepreneurs and workplace experts. We believe in sharing our stories, unpacking exactly how we did it and talking through the mindset shifts needed to achieve great things.Let's connect further!!LinkedIn HERE IG @cpennington55 FB HEREChilledVino HERE