Sheila Slick< MS shared their story and experiences with us recently and you can find our conversation below.
Sheila, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What makes you lose track of time—and find yourself again?
Writing makes me lose track of time in the most grounding way possible. I’ve always loved stories and their ability to transport, to connect, to reveal truths we didn’t know we were searching for. When I write, I lose track of time and the world narrows to just the page and the words flowing through me. Sometimes I park a thought or even record these stories as they come to me, to capture the raw energy of the moment. I’ve come to love this practice not just for the stories themselves, but for their transformative power and the way they’ve opened unexpected doors and led me down paths I never imagined taking. There’s something profoundly balancing about it, too. Writing lets my mind wander freely, releasing whatever has been building up inside, from thoughts to emotions to tensions I didn’t even know I was carrying. Through writing I find myself again, clearer and more centered than before.
Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Sheila Slick, MS, a strategic business consultant, author, and entrepreneur with over 25 years of experience building businesses across multiple countries. As founder of Five Milestones LLC, my latest work is PodToBook.ai, an AI-powered platform that transforms podcast episodes into professionally written, publishable manuscripts. I’m also the host of Milestone Moments in Business and Leadership podcast, where I share practical insights to help entrepreneurs build momentum and achieve consistent progress in their businesses.
My international background has given me a unique perspective on navigating change, identifying opportunities, and building sustainable business practices. As a former SCORE Chapter Chair for Volusia/Flagler County (2021-2023), certified entrepreneurship facilitator, and Entrepreneur in Residence at a local college, I have provided guidance to hundreds of entrepreneurs.
That’s why I wrote Momentum: Daily Practices to Build Your Business & Thrive, a book that delivers ten proven practices designed specifically for freelancers, entrepreneurs, solopreneurs, and self-employed professionals who struggle to maintain consistent progress toward their business goals. Whether through PodToBook.ai, which empowers creators to amplify their voice across multiple formats, or through Momentum, which provides a practical roadmap for building consistency, my work centers on one core belief: transformation happens when we close the gap between what we know and what we do, one intentional step at a time.
Amazing, so let’s take a moment to go back in time. What’s a moment that really shaped how you see the world?
In 2008, when the iPod Touch had just been released and mobile apps as we know them today were brand new, I decided to learn how to code and started building educational apps as a hobby. This was unconventional for a mother of three with no technical background, but I was fascinated by the possibilities.
About three years later, I was invited to participate in a NASA Space Apps Challenge by a local college in my birth country of Nicaragua, where I was living at the time. I initially turned down the opportunity because I didn’t feel I could program something that sophisticated. My own limiting beliefs held me back.
When I went home and told my kids about my day, in disbelief that they had invited me to participate so the country could be represented in the competition, they reminded me of something crucial: I couldn’t fail if I didn’t try, and I wasn’t even trying. To motivate me, they said they would be part of my team. Together, we built iSpotit!, an app that created awareness of the International Space Station and tracked its location in real time so people could share their sightings.
Out of 7,600 participants worldwide, NASA selected our app as a global nominee, and we received a Global Honorable Mention for Most Inspiring. That moment transformed how I view the world. Nothing is impossible if we try. I also realized that I had the ability within me the entire time. I just needed external validation to prove to myself that I could, that I was capable of doing something I first thought was way out of my league.
After that recognition, a new company was born, focused on helping businesses and nonprofits build their digital platforms through apps, websites, and technology solutions. That work laid the foundation for what I do today through Five Milestones LLC and PodToBook.ai, which breaks down barriers by empowering creators to amplify their voices and transform their expertise into lasting impact.
What’s something you changed your mind about after failing hard?
As a lifelong entrepreneur, I’ve co-founded and founded a total of four successful businesses, but there have been multiple other ideas that didn’t work out. I’m giggling as I write this, remembering some of the many different ones we tried: exporting plants by the inch after attending workshops on international trade, creating coconut panels for construction from tiny pieces of coconut shells, solar water and light panels for remote urban areas, a human flying drone, even buying a flower shop that had been in business for 30 years and testing the waters to become a florist. Some even required purchasing inventory that we eventually just gave away. The lesson I learned the hard way is that you should always validate your ideas before going all in, and also make sure you truly believe in what you’re building, selling, or doing. You can’t skip either of these crucial steps, which so many entrepreneurs miss. I used to believe that passion and hard work were enough, but I’ve learned that market validation is just as important. Now, before I invest significant time or resources into any new venture, I test the idea, talk to potential customers, and make sure there’s real demand. That shift in mindset has saved me from countless mistakes and helped me focus my energy on ideas that actually have real potential.
Sure, so let’s go deeper into your values and how you think. What’s a cultural value you protect at all costs?
Perspectives, compassion, and tolerance. By living in different countries throughout my life, I’ve come to deeply cherish the traditions and values each culture offers. This experience has taught me that there’s rarely just one right way to do things. What works beautifully in one culture may look completely different in another, and both can be equally valid. I protect this understanding fiercely because it keeps me open, curious, and humble. It reminds me to listen more than I speak, to ask questions before making assumptions, and to recognize that my perspective is just one of many. In business and in life, this cultural awareness has been invaluable. It’s helped me connect with people from all walks of life, navigate complex situations with empathy, and build solutions that honor different needs and viewpoints. At all costs, I protect the value of seeing the world through multiple lenses, because once you truly understand that diversity of thought and tradition is a strength, not a challenge, everything changes.
Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. Could you give everything your best, even if no one ever praised you for it?
Yes, absolutely. I believe everyone should give their best, even without praise, and one way to do that is by volunteering. The real reward is seeing someone succeed because of the guidance or support you offered. It’s about making a tangible difference in someone’s journey, whether that’s helping them launch their first business, navigate a challenge, or simply gain the confidence to take the next step. Sometimes it’s just about feeling heard and validated. Some people don’t have someone to share their voice or concerns with. Being that one person who perhaps can spark a change or make them feel supported is priceless. That impact matters far more than any recognition ever could. Giving your best effort, regardless of whether anyone notices, is a reflection of your character and your commitment to contributing something meaningful to the world.
Contact Info:
- Website: https://fivemilestones.com
- Linkedin: https://www.linkedin.com/in/sheilaslick/
- Other: Milestone Moments in Business & Leadership Podcast
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Image Credits
Self
