We were lucky to catch up with Caleb Drew recently and have shared our conversation below.
Caleb, looking forward to hearing all of your stories today. We’d love to hear about the things you feel your parents did right and how those things have impacted your career and life.
My parents did a lot of things right. They instilled foundational values in all of us from an early age—values like hard work, consistency, setting a high standard, and developing the entrepreneurial spirit to bet on ourselves. They led by example on a daily basis, setting the tone for us children to follow suit and always strive to be our best. Whether they were putting in 16-hour days on the farm, raising four children at different stages of life, or communicating non-verbally how we should seize each day and avoid excuses, they set a clear bar for us to meet.
One story that comes to mind is from when I was first adopted. My parents were insistent that we kids give our best in any task we undertook. It was my senior year of high school, and I had been known for having high athletic potential but little work ethic. My mother and father sat me down before the football season and said, “Listen, you can excel in any facet of life, but if you’re afraid to suffer and work hard consistently, you’ll struggle to reach any abundance or accomplish your goals.” That season turned out to be my best statistically, with Division I offers coming in and individual accolades. The impact of that conversation—along with many others—still lives with me today.
They remain the guiding standard for me and continue to influence my daily life and career
Caleb, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I’m a personal trainer and the founder of Wingman Training, a health and wellness company based in Fort Lauderdale. My journey into this field started during my time as a college athlete, where I first developed a deep interest in longevity, functional fitness, and the kind of well-rounded lifestyle that supports both performance and overall wellbeing.
At Wingman Training, we offer personalized 1-on-1 in-person training sessions, tailored specifically to each client’s goals, abilities, and lifestyle. We also provide comprehensive online programs designed for a wide range of people—from beginners stepping into the gym for the first time to more experienced individuals looking for structure and support to level up their training.
What sets us apart is our focus on functionality, and our ability to connect with people from all walks of life. Our approach is not one-size-fits-all—we emphasize movement that makes sense for your body and your goals, while fostering a strong sense of trust and teamwork.
What I’m most proud of is the diversity of our client roster and our 100% retention rate. That speaks volumes about the community we’ve built—one that’s inclusive, inspiring, and full of people supporting each other no matter where they are on their fitness journey.
At Wingman, we’re not just about workouts. We’re about building habits that last, making meaningful progress, and doing it all in a space that feels like home. Whether you’re looking to move better, feel stronger, or just start showing up for yourself in a new way—we’re here to help make that happen, together.
What’s been the most effective strategy for growing your clientele?
For me, the most effective strategy for growing my clientele has been visibility and word of mouth—hands down. Everything we’ve built at Wingman Training has been organic, and that’s something I take a lot of pride in.
It all comes back to the premium service we deliver and the attention to detail we bring to every single client. When people feel truly seen, supported, and challenged in the right way, they talk about it. Whether it’s someone hitting a major milestone, overcoming an injury, or just feeling more confident in their body—that kind of transformation speaks for itself.
At the end of the day, authenticity and consistent excellence are what drive growth. We focus on showing up for our people, and they naturally become advocates for the brand because they genuinely believe in it.
Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?
Absolutely—there are several books that have had a major influence on how I approach both training and entrepreneurship. Outlive by Peter Attia has been incredibly impactful in shaping my philosophy around healthspan and long-term wellness. It really helped reinforce the idea that training isn’t just about looking good or hitting numbers—it’s about creating a sustainable, functional body that supports a high quality of life for decades to come. That mindset plays a big role in how I build programs for my clients at Wingman Training.
Another foundational resource for me was Becoming a Supple Leopard by Dr. Kelly Starrett. It was one of the first books I dove into when I started Wingman Training in 2020. It’s packed with practical, movement-based knowledge and really grounded my approach in functionality and performance.
On a more philosophical level, Man’s Search for Meaning by Viktor Frankl gave me a deeper perspective—not just on training, but on life. It’s a reminder of the importance of purpose, resilience, and mindset, which are all things I try to instill in my clients and carry with me as a business owner and coach.
These books continue to shape how I train, how I lead, and how I show up every day—for my clients, my business, and myself.
Contact Info:
- Website: https://wingmantraining.com
- Instagram: wingmantraining
Image Credits
Photo 1: Dr. Mona Amin, Pedsdoctalk Owner
Photo 8: Jacob Ingram, CEO of Defiance Analytics – Swimming session