The Caroline Pennington Show

Hosted by Caroline Pennington

Business Entrepreneurship Education

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Episodes

201

Latest episode

Oct 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!

Listen to episodes

60 recent

October 27, 2026Episode 2035 min

203: {Sassy Solo} Why You Need to Market Your Business on Social Media

Text me! We live in an online and AI generated world and you need to be showing up online too. No matter your goal, you still need to be marketing yourself and your business on social media. And don't do it for the vanity metrics, do it for long term growth and awareness. And I still think organic social media is the way to start. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

October 20, 2026Episode 2023 min

202: {Sassy Solo} How to Overcome the Haters and Trolls

Text me! In today's episode, I'm talking through exactly how to handle the naysayers and Karen's of the internet. Listen in for my hot take on how to handle the haters and the trolls when you start to put yourself out there online. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

October 13, 2026Episode 2012 min

201: {Solo} Why Boundaries are so Important

Text me! In today's episode, we are talking all things boundaries. Boundaries are great in both your personal and professional relationships. It's been a work in progress for me, but a skill that has done me more good than bad. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

October 6, 2026Episode 2004 min

200: {Solo} Our Contrast Therapy Experience

Text me! In today's episode, I'm breaking down a recent experience that Gary and I had which was: Contrast Therapy. Contrast therapy is a mix of cold plunging and infrared sauna and combining the two. It was our anniversary weekend, so I wanted to try something new for us to experience and I'd give it a 10/10. So ladies, if you have an opened minded partner.... try contrast therapy! Savannah Infrared Sauna can be found HERE Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

September 29, 2026Episode 1992 min

199: {Sassy Solo} Stop using AI to Create Content

Text me! In this episode, I'm breaking down why you should not relay solely on AI to create content. Why? Because it's generic and you will come across as a bot to your customers and potential customers. People want to know who the human that they are hiring is and how they can help them solve their problem. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

September 22, 2026Episode 1983 min

198: {Sassy Solo} Don't sleep on social media

Text me! It's 2026 and we are all online. So when you tell people about your business or what you do for a living.... guess what? They look you up online. And you want to make sure you have an active business page. Active content for them to view. Your page optimized because you will have less than 3 seconds of their attention. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

September 15, 2026Episode 19719 min

197: {Interview} Finding Your Superpower in Business and Life with Allison Greco

Text me! In this episode, Allison Greco shares her journey from wildlife rehabber to top real estate agent, emphasizing the importance of authenticity, prioritization, and honest communication in business and life. Discover practical advice on scaling a service-based business, handling difficult clients, and staying true to your values. Takeaways Authenticity and honesty are key to building trust and success. Focusing on one core value or service helps in deepening expertise. Prioritize your commitments and be accountable to your calendar. People value genuine connection over superficial perfection. Hard work and consistency are essential for long-term success. Connect further with Allison HERE or follow her on IG @realestateandrehab Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

September 8, 2026Episode 1961 min

196: {Solo} Stop Lurking and Start Supporting Your Friends Online

Text me! If you know someone who is building a personal brand or business online, support them! Like their posts, share their content because they only think it takes is a couple of mins of your time, but goes a really long way! Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

September 1, 2026Episode 1955 min

195: {Solo} The Power of Using Social Media to Market Your Business

Text me! If you are not using social media to market your business, then what are you even doing? We live in a digital age and when people find out about your business or what you do... they go look you up. They google you or get on Facebook at find your company page. And if your profile is not optimized or you do not have recent content out there, bye bye. You've lost of potential client or customer. Because you have less than 3 seconds to capture their attention. So it needs to be crystal clear..... who you are, what you do and how you can best serve them and help them overcome a problem. Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

August 25, 2026Episode 19421 min

194: {Interview} Traveling Beyond the Ordinary: Insights from Jen Barnes

Text me! In this episode, travel expert Jen Barnes shares insights on planning trips for different seasons, the impact of climate change on travel, and the benefits of working with a travel concierge. Discover how personalized travel planning can enhance your travel experience and make it more memorable. Takeaways Include: Best travel seasons for different destinations Impact of climate change on travel planning Advantages of working with a travel concierge Traveling with family and multi-generational groups Traveling solo and destination recommendations How climate change affects seasonal travel patterns The rise of travel budgets among younger generations Benefits of personalized travel experiences You can find her on IG @jenbarnestravel or LinkedIn HERE Support the show LINKS 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 DM ABOUT THE HOST: Former Executive Recruiter turned Digital Marketing Expert & Entrepreneur. I'm here to show you that you can do it too! I help small business owners 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 Caroline Pennington Show Podcast and in 2025 I launched my Digital Marketing Agency called CPM. 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 HERE ChilledVino HERE

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