In this deeply candid episode of Exit-Ed, host Gabriela Smith sits down with entrepreneur Skip Johnson for a raw, reflective, and highly practical conversation about what it really takes to scale a business—and then let it go.
Skip, a former architect turned financial services founder, shares the winding path that led him from small-town Minnesota to co-founding a retirement planning firm that scaled from a team of two to over 70, earning accolades like the Inc. 5000 and Minnesota Fast 50. With clarity and humility, Skip walks us through the defining moments of his entrepreneurial journey: discovering a passion for client-centric systems, navigating betrayal in his early career, rebuilding with integrity, and ultimately exiting his business not to a PE giant, but to internal partners.
The conversation dives into critical lessons for founders: why identifying your personal “why” matters more than loving your product, how to set client boundaries while building trust, and why entrepreneurs must consistently reassess their businesses—and themselves. Skip shares the pivotal moment a key employee left, forcing him to shift from running an advisory “practice” to building a scalable, systemized company.
We also explore the emotional terrain of exiting: the identity crisis that often follows, how to handle fractured partnerships, and why selling your business is more like a personal reinvention than a financial event.
Now the founder of Tailwinds and River Bend Refuge, Skip supports other business owners as they hit the scaling wall and helps guide them toward healthy growth—personally and professionally. Whether you’re still in the trenches or thinking about the next chapter, this episode is a masterclass in perseverance, boundaries, and intentional leadership.
Tune in to hear how faith, failure, systems, and therapy all played a role in building—and exiting—a business with purpose.
For more about Skip: https://www.linkedin.com/in/skipgjohnson/ Tailwinds Group: https://www.tailwinds-group.com/ Gratus Funds: https://www.gratusfunds.com/
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