I Built $40M in Businesses... and Was Miserable

I Built $40M in Businesses... and Was Miserable

June 18, 2026 · 55 min · Season 4 · Episode 24

About this episode

Dominic Rubino and Spencer Sheinin discuss the journey from financial success to purpose-driven entrepreneurship, exploring the challenges faced by contractors and the importance of creating impact beyond profits.

Most contractors and business owners spend years chasing revenue, bigger teams, and more success, only to wonder why they still feel stuck. In this episode, Dominic Rubino sits down with CPA, entrepreneur, and author Spencer Sheinin to discuss the journey from financial success to purpose-driven entrepreneurship. Spencer shares his experience building four businesses, generating over $40 million in revenue, and discovering that success alone wasn't enough. Together they explore why so many contractors feel trapped in "robot mode," the importance of financial stability, and how business owners can create impact beyond profits. You'll also discover Spencer's three entrepreneurial archetypes—the Pure Archetype, Conscious Archetype, and Abundant Archetype and how understanding your own path can help you build a business that provides meaning, fulfillment, and financial freedom. Whether you're a contractor, home service business owner, trades entrepreneur, or leader looking for greater purpose, this conversation will challenge the way you think about success and what comes next. In this video, you'll learn: • Why money alone doesn't create happiness. • The three purpose-driven…

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