A Quarter in the Couch

In this special episode of A Quarter in the Couch , Jeremy sits down with his 17-year-old intern Eian, a high school student beginning to challenge the 9-to-5 mindset and explore what it means to build wealth on your own terms. What starts as a mentorship check-in quickly becomes a deep-dive into real-world tax strategies, business structures, and the mindsets of successful entrepreneurs. Jeremy a...

In this special episode of A Quarter in the Couch , Jeremy shares the mic with Brian Decker and the Wealth Society for a high-impact Q&A covering powerful tax strategies for W-2 earners and business owners alike. With 20 years of experience in the tax world, Jeremy breaks down how your tax bracket, life stage, and business structure can become tools—not obstacles—for building and preserving we...

In the debut of his solo mini-series, Jeremy Lindsey—tax strategist, business owner, and founder of Clarity Tax Advisors—gets real about what it took to leave a toxic job and start his own business. If you're feeling stuck in the corporate grind, contemplating entrepreneurship, or just wondering how to take the first step, this episode is a goldmine of wisdom and actionable advice. Jeremy walks th...

In this jam-packed solo episode, Jeremy Lindsey — tax strategist, founder of Clarity Tax Advisors, and your go-to guide through the maze of small business finance — unpacks the real-world impact of the One Big Beautiful Bill Act (OBBA). Whether you’re a contractor, service provider, or creative with a growing LLC, these new tax changes are more than just line items — they’re game changers. Jeremy...

This episode of A Quarter in the Couch dives into the mindset shift that separates good business from great legacy. Host Jeremy Lindsey sits down with sales coach and entrepreneur Ryan Cook for a conversation packed with practical insights, humor, and heart. Together, they unpack what it really takes to create a sales experience that breeds trust—and why systemizing your message might just be the...

In Part 2 of this unforgettable conversation, host Jeremy Lindsey and former military veteran-turned-pastor Joe McKee go even deeper into Joe’s redemptive journey—one marked by darkness, deliverance, and decades of transformation. From dancing on a church stage to wrestling with forgiveness, Joe shares raw, vulnerable stories of his spiritual rebirth and the relationships that shaped his walk with...

In this powerful first part of a two-part conversation, host Jeremy Lindsey sits down with his best friend, Joe McKee—a man whose story is one of grit, grace, and transformation. From military service and personal loss to four DUIs, violent charges, and the brink of a 30-year prison sentence, Joe’s journey seemed destined for destruction. But a last-chance offer from a judge and an unexpected enco...

Welcome to A Quarter in the Couch , where host Jeremy Lindsey—tax strategist, founder, and father—shares honest stories about money, leadership, and legacy. In this solo episode, Jeremy opens up about the breaking point that ended his 14-year career at a top firm. After years of sacrifice, long hours, and emotional wear, two simple words— “I resign” —sparked the start of something new. He shares t...

Welcome to the very first episode of A Quarter in the Couch , hosted by Jeremy Lindsey—elite tax strategist, founder of Clarity Tax Advisors, and a father with a vision. Jeremy’s goal for this podcast is simple but profound: to create a living legacy through honest, accessible conversations about money, business, and personal growth. This show isn’t about jargon or lectures—it’s about sharing wisd...

A Quarter in the Couch is a weekly podcast where elite tax strategist and Clarity Tax Advisors founder Jeremy Lindsey sits down with visionary founders, athletes, and creatives to uncover how small, well-placed ideas can grow into generational wealth. Each episode mixes plain-English money moves with legacy lessons—drawing on Jeremy’s $25k onboarding frameworks, wisdom from his 77-year-old tax-leg...