“Dream First, Then Execute”—Jason VanDevere on Choosing Purpose over the Family Business

Cut The Tie Podcast with Jason VanDevere

What happens when the family business is your “golden ticket”—but not your dream? In this episode of Cut The Tie, Thomas Helfrich sits down with Jason VanDevere, entrepreneur, creator of the Goal Crazy planner, real estate investor, and author of Dream Driven.

Jason shares how he walked away from a fourth-generation car dealership legacy to build something of his own: a business that helps people clarify goals, make plans, and execute daily. From designing a paper planner in a digital-first world, to building a subscription model, to publishing his new book, Jason’s story proves that cutting the tie to expectation can open the door to true ownership—of your career, your time, and your life.

About Jason VanDevere

Jason VanDevere is the founder of Goal Crazy, a 90-day planner designed to help people set meaningful goals, make daily progress, and hold themselves accountable. What began as a side project has grown into workshops, courses, coaching programs, and now his new book, Dream Driven, which guides aspiring entrepreneurs in finding the right business idea, validating it, and launching it with confidence. Alongside his business, Jason has built a portfolio of rental properties and, most importantly, a life centered on his wife and three young children.

In this episode, Thomas and Jason discuss:

Cutting ties with the family business
Jason explains how he stepped away from his family’s dealerships despite success, expectations, and his last name on the building.The journey to creating Goal Crazy
From six months of interviews with entrepreneurs to seven brutal focus groups, Jason describes how persistence turned an idea into a viable product.Why paper still wins
Jason breaks down why a physical planner beats digital apps for focus, clarity, and productivity.Stacking assets: planner, coaching, book
How one simple product turned into a system of revenue streams and positioned Jason as a thought leader.Designing a life you want
Building a business that supports a 30–35 hour workweek, time with family, and long-term wealth through real estate.

Key Takeaways

Dreams give goals meaning
Without a dream, goals lack direction and purpose.Clarity beats complexity
A simple written plan executed daily drives better results than juggling multiple apps.Ship, then sharpen
Painful feedback is the key to creating a product people actually use.Build assets that stack
A product can open the door to coaching, courses, and a book—each fueling the next.Define success on your terms
Jason measures success by supporting his family and raising his kids—not by titles or legacy.

Connect with Jason VanDevere

💼 LinkedIn: https://www.linkedin.com/in/jasonvandevere/
🌐 Goal Crazy (90-Day Planner): https://goalcrazy.com

Connect with Thomas Helfrich

🐦 Twitter/X: https://twitter.com/thelfrich
💼 LinkedIn: https://www.linkedin.com/in/thomashelfrich/
🌐 Website: https://www.cutthetie.com
📧 Email: t@instantlyrelevant.com
🚀 Instantly Relevant: https://instantlyrelevant.com

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