We’re excited to introduce you to the always interesting and insightful Derek Krehling. We hope you’ll enjoy our conversation with Derek below.
Derek, looking forward to hearing all of your stories today. What did your parents do right and how has that impacted you in your life and career?
One of the greatest gifts my parents gave me—especially my father—was a mindset of self-reliance and entrepreneurship. From an early age, my dad encouraged me not just to dream big, but to do big. He didn’t just support the idea of me starting a business—he helped me build the skills and confidence to make it real.
At 13, I launched my first business: a lawn mowing company. It started with just me and a mower, but over the years, I grew it into something more—eventually managing a small team, running two trucks, and ultimately selling the business at 21. I even carved out a unique niche mowing lawns on an island in the middle of the Susquehanna River.
One moment from that time stands out vividly. I was 14, alone on the 275-acre island, two miles from my boat, and my mower had broken down on a dirt path. Frustrated and stuck, I called my dad. He gave me a couple of troubleshooting tips, but before hanging up, he said something I’ll never forget: “You have the tools to fix the problem. Get in and figure it out.”
That moment was a turning point. It taught me that success isn’t about avoiding problems—it’s about meeting them head-on. That mindset—resourcefulness, grit, and a belief that most problems have a solution if you’re willing to work for it—has been the foundation of my career ever since.
My parents didn’t hand me a roadmap. They gave me something better: the confidence to chart my own.
Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
At Krehling & Associates, we like to say we started our business backwards. While managing a previous company, my wife and business partner, Amanda, began shopping for better health insurance after our broker dropped the ball. She found us a plan that saved 20%, and when a client asked how we got such a good deal, I explained what Amanda had done. That conversation sparked an opportunity—but before moving forward, Amanda took the initiative to get licensed. Once she was officially licensed, she helped that client switch their benefits and saved them money too.
From there, things moved quickly. Word spread, demand grew, and eventually I sold my share of my previous business, got licensed myself, and joined Amanda full time.
Today, we specialize in health and life insurance, with a focus on employee benefits. We serve both businesses and individuals, offering tailored coverage for medical, dental, vision, disability, life, and more. What sets us apart is our service—we function as an extension of our clients’ HR teams, providing hands-on support and strategic guidance.
We’re proud that our business was built on solving a real problem—our own. Now, we do the same for others, helping clients save money, stay compliant, and offer great benefits without the usual headaches.
How do you keep your team’s morale high?
My core philosophy for leading a team is simple: don’t ask anyone to do something you aren’t also willing to do yourself. Leadership starts with example—showing up, staying engaged, and being present in the day-to-day of the business. When your team sees that you’re in the trenches with them, it builds trust, respect, and a shared sense of purpose.
High morale doesn’t come from perks—it comes from culture. People want to feel supported, valued, and part of something bigger than just a job. That starts with leadership being visible, approachable, and committed to the same standards and goals expected of the team.
Have any books or other resources had a big impact on you?
Rich Dad Poor Dad
Profit First
The Subtle Art of Not Giving a F*ck
Contact Info:
- Website: krehlingassociates.com
- Instagram: https://www.instagram.com/krehlingassociates
- Facebook: https://www.facebook.com/krehlingassociates
- Linkedin: https://www.linkedin.com/in/derek-krehling/
