Leonard Cagno’s story is one of reinvention — a career built on focus, adaptability, and purpose. Growing up in West Hempstead, New York, he played football, volleyball, and basketball, learning early that persistence often matters more than talent. That mindset stayed with him through every chapter of his life.
After earning his Aviation Management degree from Dowling College, Cagno became a flight instructor, later flying the Q400 and CRJ900 for a regional airline under the Continental Airlines brand. Flying taught him discipline, calm under pressure, and the power of preparation. “You can’t panic at 20,000 feet,” he says. “You rely on training, focus, and clear thinking. Business works the same way.”
He transitioned into finance as a financial adviser at AXA, earning his Series 7, 66, and health and life licences. There, he learned that relationships — not numbers — drive real success. Over time, his entrepreneurial side took over. He helped build and grow companies like Cambridge Who’s Who, Marquis Who’s Who, ACS Consulting, TEG Health, and TEG Wellness.
Today, as a Partner at TEG Health & TEG Wellness, he focuses on blending wellness, technology, and business systems to improve lives and workplaces. Outside of work, Cagno is a devoted father who loves flying, hockey, and family time — finding balance in every aspect of life.
What is your typical day, and how do you make it productive?
I start early — before most people are awake. I spend 30 minutes planning my day, reviewing goals, and setting priorities. I’ve found that mornings are when my mind is clearest. I block my calendar into “must do,” “should do,” and “nice to do” tasks. That system keeps me focused on what truly moves the needle. I also try to avoid multitasking. Whether I’m in a meeting or working on strategy, I’m fully present.
How do you bring ideas to life?
I start by asking, “What problem does this solve?” Then I map it out — what resources, people, and systems are needed. I like to visualise everything on a whiteboard before it becomes a plan. Once it’s clear, I move fast but stay flexible. I believe in building structure around creativity so ideas don’t get lost in theory.
What’s one trend that excites you?
The merging of wellness and technology. I’ve seen how digital tools can make healthcare more personal and accessible. But the real opportunity is in integration — making benefits, wellness, and payroll systems talk to each other. That’s where businesses will see the biggest impact.
What is one habit that helps you be productive?
Reflection. Every Friday afternoon, I review the week — what worked, what didn’t, and where I can improve. It’s simple but powerful. I treat it like a pre-flight checklist for my goals.
What advice would you give your younger self?
Don’t rush success. Every stage teaches you something valuable. I used to think speed meant progress, but real growth comes from learning, adapting, and being consistent.
Tell us something you believe almost nobody agrees with you on?
That failure is not just feedback — it’s fuel. Most people fear it, but I think failure keeps you grounded. It forces you to rebuild smarter.
What is the one thing you repeatedly do and recommend everyone else do?
Set time boundaries. Work will always expand to fill your day if you let it. I’ve learned to protect personal time. Balance isn’t a luxury; it’s a requirement for longevity.
When you feel overwhelmed or unfocused, what do you do?
I go outside or I fly. Movement clears my mind. Flying, especially, reminds me to zoom out and see the bigger picture — literally and figuratively.
What is one strategy that has helped you grow your business or advance in your career?
Hiring for character over skill. You can teach skill, but you can’t teach integrity or work ethic. Surrounding myself with people who share my values has made every company stronger.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early on, I tried to do everything myself. I thought working harder meant better results. It didn’t. I burned out. Over time, I learned the power of delegation and trust. Building a strong team allowed me to step back and focus on vision rather than micromanagement.
What is one business idea you’re willing to give away to our readers?
A platform that helps small businesses integrate wellness benefits and payroll under one dashboard. It sounds simple, but most companies still manage those separately. The time savings alone would be huge.
What is one piece of software that helps you be productive? How do you use it?
I use Notion to track projects, goals, and notes. I treat it as my second brain — everything from meeting summaries to new ideas goes there.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I’m a fan of Atomic Habits by James Clear. It’s a reminder that big results come from small, consistent actions. It mirrors how I approach both business and life.
What’s a movie or series you recently enjoyed and why?
The Bear. It’s about chaos, leadership, and the importance of staying composed under pressure. I relate to that — both in the cockpit and in business.
Key learnings
- Structure creates freedom: a clear plan allows for flexible thinking.
- Hiring people with integrity builds stronger, more adaptable teams.
- Balance and boundaries are essential to long-term success.
- Reflection turns experience into progress — review your week before moving forward.
- Real growth often starts where comfort ends.