At twenty-three, Jason Cheperdak was driving a forklift overnight at Walmart, a year into marriage and a few months removed from life as a national-medalist athlete. He couldn’t see the way out. So he stopped waiting for a door to open and started finding the next handle. This is the story of ninety-nine slammed doors, a first million at thirty, and the two questions that rebuilt a life.

About the Guest

Jason Cheperdak is the founder of Shepherd Homes Group, the #1 real estate team in the DMV, with seven companies, a team of 80, and more than 1,100 properties under management. A former Canadian junior national bronze-medalist ice dancer, he arrived in the U.S. with $5,000, drove a forklift overnight at Walmart, became the youngest Target store manager in the country at 24, and built his first million by 30.

Chapters

00:00 Introduction: From Walmart to Real Estate Success

02:19 Building Resilience Through Hard Work

04:46 The Power of Mentorship and Mindset

09:03 Leading a $120 Million Business

12:44 Taking the Leap into Real Estate

16:33 Becoming a Millionaire at 30

17:28 Quitting During COVID and Betting on Himself

18:18 The Value of Coaching and the Right Circle

20:33 Family's Role in Entrepreneurial Success

25:07 Leaving Corporate to Build Multiple Businesses

27:01 Financial Lessons from Growth and Tax Challenges

30:07 Leading with Abundance and Purpose

32:24 Creating a Scalable Business and Lasting Legacy

36:11 Personal Growth Through Relationships

38:58 Advice for Anyone Feeling Stuck

40:17 Curiosity, Persistence, and Better Decisions

44:43 The Questions That Transform Your Life

46:38 How to Connect with Jason

In this conversation

• The overnight forklift shift and the breaking point that started everything
• Reverse-engineering 25 years of his life and walking away from the ladder
• Fifteen feet of fire, a coach, and the decision to go all in
• Fear, scarcity, and learning to bet on himself
• The two questions he runs every decision through

Connect with the Guest

• Instagram: @jasoncheperdak
• Website: shepherdhomesgroup.com