Drew Shockley grew up on a dairy farm in Tennessee. He started working in insurance for $7.50/hour, and by his 30s had built and sold multiple companies—including an eight-figure exit in 2020.

From the outside, it sounds like a dream. But the road to Drew’s success was not a straight path. Along the way, he experienced burnout and struggled with the pressure of leading a much larger team. The personal lessons really stuck with him.

In this episode of the award-winning Healthy Advisor podcast, WealthManagement.com’s Diana Britton is joined by Drew Shockley, co-founder of Move Health, a platform that helps financial advisors forecast pre-retirement health insurance costs. He opens up about the struggles behind the success. He also reflects on building something more intentional this time around and how those lessons resonate with any entrepreneur or financial professional today.

Drew discusses:

His unique path from the farm to forming and selling multiple companies
The personal struggles with burnout and the pressure of leadership
Balancing personal and professional life to find sustainable success
His passion for personality assessments and how that has shaped his career
How Move Health can help financial advisors forecast health insurance costs

Resources:

Listen to The Healthy Advisor on WealthManagement.com
Subscribe and listen to The Healthy Advisor on Apple Podcasts
Subscribe and listen to The Healthy Advisor on Spotify

Connect with WealthManagement.com:

Connect With Drew Shockley:

About Our Guest:

Born and raised in East Tennessee, Drew Shockley moved to Indiana for college and decided to make it home. He began his career in healthcare insurance in 2005 with Anthem Blue Cross Blue Shield, one of the nation’s largest carriers.

Over the course of his 20-year career, Drew has trained thousands of agents in the health and Medicare space and has been a founding member or investor in three successful startups within the healthcare market.

He’s been married for 19 years and is the proud father of two teenage boys. On weekends, you’ll likely find him on the golf course, cheering on the Vols at a sporting event, or spending quality time with his family.

If you have a struggle and wish to share your experiences and help others in similar situations, please reach out to Diana at diana.britton@informa.com.