We recently connected with Olivia Pool and have shared our conversation below.

Olivia, looking forward to hearing all of your stories today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?

So, about 13 years ago, I was living in Charleston, SC and was running a thriving art magazine. For many years, the media world had been really fun, but I had started diving deep into personal development and all the champagne parties were beginning to feel shallow. I was craving more depthful connections and conversations and not much of that was happening around me. I dreamed of being surrounded by a community of thinkers and seekers, people who loved learning and growing as much as I did.

I came up with the idea of having a school, a community center specifically for those who wanted to evolve together. Late one night, the full idea arrived in an intuitive flash and my best friend and I bought the domain www.evolveacademy.love.

Often, when we make an internal decision that is in alignment with what the Universe has in store for us, external things start to shift.

Not long after, I sold the publication, got rid of most of my possessions, and moved to LA to do a Master’s in Spiritual Psychology. This was just the beginning of diving into a variety of other learnings and certifications. Without having any desire to become a coach, people kept requesting my help and I ended up having a successful business as a life coach. I still see clients from all over the world. If you want to chat or learn more about that, you can find me here: www.oliviapool.com.

While I was in LA, this idea of having a school for personal and professional development kept tugging at me. I tried to create it there, but not much happened. I then tried to launch an online version, but again, not much happened. I kept having this intuitive feeling that it needed to be an in-person experience in a place where people were doing less personal development than in LA, a place where this work was really needed (like the Southeast of the US).

I bounced around from Los Angeles to Austin and to Hawaii living a really sweet life running my coaching practice until intuition struck again and I was guided to move back to Charleston, SC. I was resistant to leaving Hawaii – it’s the hardest place ever to leave! Once again, intuition intervened. Not long after arriving in Charleston, I had a feeling I should go pop into this building called The Schoolhouse. I wasn’t sure why I was going over there, but ended up meeting someone who was looking to sublet her rental space and it all went very quickly into motion for the birth of Evolve Academy to be a physical space for personal and professional development, as well as a community center.

Sometimes when we have dreams and they don’t happen immediately, it’s because that dream is waiting for the right time and place for it to thrive. And there’s a lot to be said for letting Intuition lead the way.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I run two businesses.

1. I have a private transformational coaching practice that is rooted in Spiritual Psychology principles and Subconscious Reprogramming. I mostly work with creative and spiritual entrepreneurs who have already done some level of personal development. They typically come to me when they have plateaued in one or more areas of life: they’ve achieved a lot of success with all the things they were “supposed” to be, but now they are feeling stuck with some blocks and/or repetitive patterns, or they are just feeling unfulfilled, and not aligned with their purpose. I typically show up on their radar when they are ready to be supported in moving to their next level. www.oliviapool.com.

2. I am the Creator and CEO of the Evolve Academy of Conscious Learning, a physical school for personal and professional development located in West Ashley, Charleston, South Carolina. Our classes focus on all the most important things that we should have been taught in school but weren’t. Our classes range from conscious business classes to sacred sexuality to astrology, Human Design, meditation, and overall life skills classes that are here to help you navigate all the ups and downs of being human. Each month, we pick a different theme so the content is always changing! Sign up for our newsletter or follow us on Instagram: www.evolveacademy.love and @evolveacademy.love

Let’s talk about resilience next – do you have a story you can share with us?

I opened the doors of Evolve Academy in July of 2025. We had an amazing dance party and people were so excited to have an in-person place for expanding their consciousness and making new friends who are also on that path. I was blessed by all the people that showed up to make that happen. People are always excited about the beginnings of things.

After the initial hurrah, the daily grind set in with continued upkeep and marketing and all the backend admin stuff. I’m a visionary and a big picture person so handling all the day to day felt hard for me. Most of that fell on me to do as I didn’t have the budget to hire anyone at the time. In addition to starting a new business, I was also in the process of doing a house renovation and going through a big break up, not to mention all the fun things that come with perimenopause!

When I look back on the last year of my life, half the time, I think I must have been insane to start this business in the middle of all that! And the other half of the time, I see how much support and grace I have continuously received from friends and from the Universe/God. I also see the amazing amount of resilience and tenacity in me to keep it all going – mostly solo – on the days when it wasn’t fun and sexy. Every time I get to witness someone having a huge a-ha moment in one of our transformational workshops, I am reminded of my “why” and I am so grateful to be of service to their evolution.

Any advice for growing your clientele? What’s been most effective for you?

The most effective strategy for growing my coaching business has been service-first generosity.

There are many coaches in the world these days. Some are great, some are not so great. Most of the time, you have to sign up and pay immediately to work with someone, and you don’t really know if they’re going to be a good fit for you. It’s REALLY important to feel like the person you are paying to support you through some of life’s challenges feels like the best person to support you!

What I like to do is offer a totally free complimentary session if I feel like my skill sets would help that person. In that free session, I serve them powerfully. If at the end they want to have a conversation about us working together, we have that convo. If they don’t, that’s okay with me. No strings attached. I know that I have done a good deed and I feel great about that. I also know that if I am the right person for them, they will become a client. If they loved the session but are not ready to become a client, they typically refer me to their friends.

For me, this is a long-game plan, and this service-oriented way of doing business feels good for me.

Contact Info:

• Website: www.oliviapool.com www.evolveacademy.love
• Instagram: @oliviapool @evolveacademy.love
• Facebook: https://www.facebook.com/oliviapool7
• Linkedin: https://www.linkedin.com/in/oliviapool/
• Youtube: https://www.youtube.com/@oliviapool6045

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