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 answers Eian’s thoughtful questions with clarity and depth — breaking down the difference between LLCs and S-Corps, explaining how business owners legally reduce their taxes, and sharing real examples of how he structures his own business and even puts his son on payroll.

Whether you're just starting your journey or want a refresher on what matters most in tax strategy and entrepreneurship, this episode is full of accessible gems — and a reminder that it's never too early (or too late) to build something better.

What You’ll Learn:

• Why choosing the right business entity can save you thousands in taxes
  
  
• How to avoid common IRS red flags (like abusing “business dinners”)
  
  
• What it actually means to put your kids on payroll — and why it’s legal
  
  
• The difference between short-term and long-term capital gains
  
  
• Why capturing all your expenses matters more than filtering too early
  
  
• How Jeremy teaches his son entrepreneurship, discipline, and retirement planning at age 11

Guest Spotlight:

Eian, Jeremy’s 17-year-old intern, brings sharp questions and fresh perspective. Curious, driven, and wise beyond his years, Eian is beginning to realize there’s more to life than just working a job — and this conversation proves he’s on the right track.

If you found value in this episode, take a moment to subscribe, follow, or like A Quarter in the Couch wherever you listen. And don’t forget to share this episode with a friend who’s ready to start building wealth on their own terms.

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 wealth.

You’ll hear how strategic charitable giving, entity setup, and personal tax consultations can help high earners and entrepreneurs get ahead, even in a changing IRS landscape. From the couch to the C-suite, this conversation is a must-listen for anyone serious about optimizing their finances.

In this episode:

• How to think like a tax strategist—no matter your income level
• The overlooked power of filing status and life-stage planning
• Charitable giving, entity structure, and deductions demystified
• Why the IRS workforce shift may be a unique opportunity

If today’s episode helped uncover a few “hidden quarters” in your own life or business, don’t keep it to yourself.

👉 Like, follow, and subscribe to A Quarter in the Couch for more real talk, real strategy, and real stories—every Tuesday.

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 through his personal journey and breaks down the essential components of launching a successful business: from finding your product-market fit to testing proof of concept, from managing burnout to getting your first sale.

This isn’t fluff. It’s the behind-the-scenes of what it really takes to build something from scratch.

In this episode:

• Why Jeremy left his family’s corporate firm after 15 years to create his own company
• How to evaluate whether your current job skills can translate into a business
• The three core pillars of every business: Sales, Fulfillment, and Finance
• Real-life examples of service-based business ideas and how to structure them
• Why “done beats perfect” every time—and how to test proof of concept
• The truth about momentum, starting slow, and managing the fear of failure
• Tips on pricing, offering client options, and making it easy to get paid
• What to do when you want to quit: routines, books, and reframing burnout
• The power of habits—and how Jeremy uses coffee and gym gear to stay consistent
• What Jeremy would tell his own son about starting a business

Takeaway:

You don’t need to be perfect. You just need to start. Sales come first, everything else follows. If you believe in the value you can bring—try, test, fail, try again, and keep going.

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 walks through the updates that matter most to entrepreneurs and small business owners, including research and development expensing, Section 179 deductions, bonus depreciation, childcare credits, opportunity zones, and more. With relatable case studies and crystal-clear breakdowns, this episode is your blueprint for proactive tax strategy in 2025 and beyond.

In This Episode:

• Why the OBBA is the biggest tax opportunity shift in years — and how to prepare
• R&D expense update: No more amortizing over 5 years — expense it all upfront
• Section 179 deduction limits raised to $2.5M (what it means for vehicles, equipment & roofs!)
• Bonus depreciation is back at 100% — and here to stay
• QBI Deduction clarified: What you need to know to qualify and optimize wages or asset base
• Qualified Small Business Stock Exclusion raised from $10M to $15M — and now permanent
• Opportunity Zones extended and redesigned — including new rural incentives
• Childcare tax credits doubled (and why this might beat a raise in your compensation strategy)
• Business interest expense deduction expanded for companies >$25M revenue
• 1099 filing thresholds raised to reduce admin burden
• Energy-efficient building, paid leave, and clean vehicle credits — what’s sunsetting and what’s new

Key Takeaways:

• If you’ve got R&D expenses, talk to your advisor — retroactive expensing can be a massive refund play.
• Raising your own salary might actually save you money if done strategically under QBI rules.
• The childcare credit and new fringe benefit opportunities are a powerful move for retention and tax efficiency.
• OBBA isn’t just a bunch of legalese — it’s your invitation to build a leaner, smarter tax plan in 2025.

Found a quarter in your couch today?
Then hit subscribe wherever you listen to podcasts and pass this episode to a fellow business owner who wants to keep more of what they earn.

📥 Download Jeremy’s OBBA cheat sheet: aquarterinthecouch.com/resources
📬 Connect directly: [email protected]

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 key to long-term growth.

From McDonald’s to MasterCard, BMW to roofing, this episode explores how memorable messaging and repeatable systems aren’t just for big brands—they’re tools that small businesses can use to elevate average performers into A-players. Jeremy and Ryan also reflect on their own work together, the emotional rollercoaster of sales, and what they want their kids and grandkids to remember about how they lived and worked.

In This Episode You’ll Learn

• Why small businesses should focus more on systems than superstars
• How to create messaging that sparks curiosity instead of giving a sales pitch
• The difference between a “sales process” and a “buying experience”
• Why your unique value prop should speak directly to your client’s real-life needs
• The power of hard work and how it fuels the math behind every sale
• How Ryan uses empathy, clarity, and strategy to build lasting client trust
• What Jeremy learned about turning consistency into confidence for his clients

Takeaway: A great sales system doesn’t manipulate—it serves. When you shift from selling to creating an experience, you give people something they’ll want to return to again and again.

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 God.

What unfolds is more than testimony—it's a living lesson in grace, grit, and the lifelong process of becoming. Whether you’re a business owner balancing stress and faith, or someone craving a friendship that goes beyond surface-level, this conversation delivers soul food.

In this episode:

• The defining moment Joe surrendered his guilt and gave his life fully to Christ
• Why transformation doesn’t always happen overnight—and what it actually feels like
• The impact of grace on Joe’s faith, relationships, and ministry
• How Joe’s perspective on love, honor, and friendship was shaped by his military background
• Jeremy and Joe reflect on their decades-long friendship and what makes a bond truly timeless
• Navigating burnout, business, and the importance of stepping away to prioritize what matters
• A simple but powerful motto for hard seasons: “Stay the course. Speak life.”

Takeaway:
It’s never too late to rebuild. Redemption is a process, and relationships, not achievements, are what make us rich.

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 encounter at Teen Challenge would change everything.

Through raw, unfiltered storytelling, Joe and Jeremy unpack not just the lowest points, but the moments of divine intervention that brought Joe from solitary confinement to street ministry, from anger to purpose. It’s a testament to second chances, faith, and finding your true calling—often in places you’d least expect.

In this episode:
•How Jeremy and Joe first met through ministry at Church on the Hill
•Joe’s life after the military—anger, addiction, and years working as a bouncer
•The arrest that nearly put him away for decades
•A pivotal court moment that led to Teen Challenge instead of prison
•Lessons from the streets of San Bernardino and the challenges of church leadership
•The influence of unlikely mentors, including a cellmate serving seven life sentences

Takeaway:
Your past doesn’t disqualify you from your purpose—sometimes it prepares you for it.

Subscribe to A Quarter in the Couch wherever you listen to podcasts so you don’t miss Part 2.

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 the full story: the moment his boss crossed the line, the fear of walking away, and how he replaced his income in just 34 days.

Whether you're stuck in a job that drains you or leading a team yourself, this episode is packed with personal insight and powerful questions about worth, work, and what matters most.

In this episode:

• Why Jeremy left a “secure” job after 14 years
• The toll of toxic leadership—and what he’d do differently
• How he built a thriving business in just over a month
• Advice for employees on the edge, and leaders who want to do better

Takeaway:

Respect is non-negotiable. Growth starts when you walk away from what no longer serves you.

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 wisdom through storytelling, authenticity, and connection.

In this special kickoff to the Father-Son Series, Jeremy sits down with his 11-year-old son, Aaron, for a candid and heartfelt conversation about saving, spending, and the lessons that stick with us. With Jeremy’s approachable tone and Aaron’s curiosity leading the way, this episode is as much about the value of a dollar as it is about the value of being present.

Whether you're a parent wanting to instill good money habits, an entrepreneur looking to connect deeper with your "why," or someone reflecting on your own financial path, this episode offers something real, useful, and lasting.

In this episode:

• Why Jeremy created this podcast as a living archive for his kids—and a resource for business owners
• Aaron's savings goal: upgrading his dirt bike through discipline and smart choices
• A unique family deal that teaches interest, patience, and self-control
• Jeremy's first money lessons mowing lawns and negotiating dishwasher duty
• Reflections on selling an Xbox, earning through chores, and learning what really matters
• Honest talk about what it means to be rich—and why relationships matter more than net worth

Takeaway: Earning is important. Saving is powerful. But legacy is built through conversations, character, and showing up for the people who matter most.

Subscribe, follow, and stay tuned—more family voices, visionary founders, and financial game-changers are on the way.

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-legend dad, and questions from his sons (ages 3 and 11). Some weeks feel like a fireside chat, others a free master class, but every week you’ll leave with actionable strategies to flip life’s hidden quarters into lasting value. Pull up a seat on the couch, hit follow, and invest in a legacy worth remembering.