Owner to Owner

Cameron Geiger
  • 5.0 (3)
  • Entrepreneurship

Building a business is a marathon, but crossing the finish line requires a specialized strategy to protect the legacy you’ve built. This owner-to-owner forum connects Northwest Arkansas entrepreneurs with the veteran CPAs, financial advisors, and fellow business owners who understand the realities of value, transition, and deal structure. Through practical, experience-based conversations, we bridge the gap between building a company and successfully navigating its sale. Tune in to gain the actionable insights and local expertise needed to turn your years of hard work into a seamless, high-value exit.

Episodes

  1. 4d ago

    Ep. 5 - Avoid Capital Gains: The Five-Year Small Business Tax Playbook

    Send us Fan Mail Entering a business transaction without a foundational legal structure is an absolute wealth drain. Many business owners spend decades building a company only to leave millions on the table because they started planning after a buyer was already sitting in front of them. The path to a highly profitable, smooth transition is paved years before a letter of intent is ever signed. In this episode, we sit down with Marcos Martinez, an attorney specializing in tax, corporate structure, and estate planning at Mitchell Williams, to break down how early legal preparation directly dictates your real takeaway at exit. We get into the critical operational mechanics that protect your life's work during a transaction. We sit down to analyze structural gaps, moving past baseline online operating agreements, and handling unrecorded handshake agreements with employees or relatives before outside parties review your data. We look closely at the massive strategic differences between asset and equity sales, highlighting the highly lucrative potential of Qualified Small Business Stock which can shield up to 15 million dollars in capital gains if structured correctly over a five-year timeline. We also break down the hidden friction points that routinely derail late-stage deals, including unread commercial real estate leases and landlord dynamics. The reality of exiting a business is that buyers handle known structural risks far better than sudden operational surprises discovered two weeks before closing. You cannot rely on broad regional economic growth to validate your final payout. Clean records, formal corporate policies, and proactive tax alignment are what actually secure your financial future. Whether your eventual transfer is a decade away or quietly approaching, getting your internal legal framework completely optimized is the only way to retain control over your timeline and valuation. If you care about maximizing enterprise value, minimizing your capital gains liabilities, and building an ironclad exit strategy, you’ll get a lot from this. Please remember to subscribe and share the video with an entrepreneur who is building for the future. What is the most undocumented or informal agreement currently running in your business that you know needs to be formalized before an outside audit? Let us know in the comments below.

  2. Jun 29

    Ep. 4 - Deal Certainty: Securing Capital Before You Sell

    Send us Fan Mail Undisclosed issues and messy financials are the fastest way to kill a small business acquisition. If you are a business owner thinking about your eventual exit, waiting until you are ready to sell to talk to a bank is a massive mistake. In this episode we are joined by Megan Lahay, VP Commercial Relationship Manager at Encore Bank, to break down exactly how buyer financing dictates the success of your deal. We get into the critical mechanics of what makes a business truly bankable before it ever hits the market. The conversation covers the necessity of buyer pre-qualification, the timeline for evaluating cash flows, the importance of clearing UCC filings, and why building an exit team is nonnegotiable. Megan shares a powerful perspective for sellers to remember throughout the process, noting that while an owner's valuation is often tied to emotion and personal attachment, cash flow is absolute fact. The hardest part of selling a business is confronting the realities of bad debt and operational dependency. A buyer stepping into an acquisition encumbered by hidden liens or a business model reliant solely on the current owner's personality will immediately lose confidence and walk away. You will walk away from this discussion with a clear understanding of why you need to clean house 12 to 24 months in advance to ensure your financials trend upward and your operations can survive without you. If you care about deal certainty, protecting your business legacy, and executing a flawless exit strategy, you will get a lot from this. Please make sure to subscribe and share this episode with other local business owners who are building value for the future. What is the biggest operational bottleneck you need to clean up before bringing a buyer to the table?

  3. Jun 15

    Ep. 3 - Funding Small Businesses: How Bank Financing Really Works

    Send us Fan Mail Assuming your ambition alone can secure a multi-million dollar commercial loan is a fast track to a collapsed deal. Navigating the world of small business acquisitions requires an early reality check because a bank does not fund your dreams or your enthusiasm. We sit down with Megan Lahay, Vice President and Commercial Relationship Manager at Encore Bank, to break down how lenders actually look at transactional risk and what it takes to get a deal across the finish line. We get into the technical realities of structuring debt and how lenders conduct a dual evaluation of both the operator and the commercial entity. Megan Lahay explains the vital importance of maintaining a healthy debt coverage ratio, how banks approach common adbacks like depreciation and interest, and why operational continuity must be secured in the asset purchase agreement. We also dive into how a buyer's personal financial strength and industry-specific management experience can ultimately make or break the underwriting process. The truth of the matter is that a great business cannot fix a bad operator, and a great operator cannot rescue a structurally broken business. Lenders look for predictability, meaning that incomplete tax returns or company-prepared financial statements that have not been vetted by a certified CPA will stall a transaction instantly. You will walk away from this conversation with a clear framework for how to position an acquisition for success, clean up your accounting records, and leverage early banking relationships to offer transactional options rather than solving late-stage problems. If you care about small business acquisitions, commercial lending structures, and building predictable business value, you’ll get a lot from this episode. Please make sure to subscribe to the channel and share this video with a fellow entrepreneur. What is the most challenging financial hurdle or bookkeeping lesson you have had to navigate when preparing a business for a major transition? Let us know in the comments below.

  4. Jun 1

    Ep. 2 - Lifetime Paycheck: Turning Business Success into Income with Craig Jamison

    Send us Fan Mail Waiting until you are forced to step away from your company means leaving your hard earned equity entirely up to chance. For many business owners, the reality of transitioning out of active operations hits suddenly, turning a lifetime of hard work into a stressful scramble for liquidity. We sit down with Craig Jamison, a financial advisor and certified exit planner from Edward Jones, to break down the mechanics of turning business equity into reliable, long term personal wealth. We get into the tactical side of structuring a successful departure long before a buyer ever arrives at the negotiating table. Craig shares insights on how to properly evaluate recurring income needs post sale, the strategic utility of utilizing seller financing to manage your tax burdens, and why 80% of an owner's net worth is frequently trapped inside their operations like a mosquito locked in amber. We also discuss how to build a unified advisory team featuring CPAs, business brokers, and attorneys to ensure your financial plan matches your true timeline. Roughly half of all exits are completely unplanned, driven by sudden health issues, partnership disputes, or unexpected burnout. When you are forced to move with pace under duress, you lose critical leverage, compromise on multiples, and make less optimal decisions that directly harm your bottom line. Viewers will walk away with a concrete framework for derisking their operations today, ensuring they maintain control over their valuation and avoid the identity crises that leads to post transaction regret.

  5. May 18

    Ep. 1 - Exit Timing: Why You Need a 3-Year Head Start with Craig Jamison

    Send us Fan Mail Most business owners are sitting on a fortune they cannot actually spend. Their net worth is trapped like a mosquito in amber, visible on a balance sheet but completely illiquid until the right deal is struck. We sit down with Craig Jamison, a financial advisor and Certified Exit Planning Advisor, to discuss why having 80 percent of your wealth tied up in a single entity is a dangerous gamble and how to start the process of unlocking that value long before you are ready to walk away. We get into the tactical differences between running a lifestyle business and building a value creation business. Our conversation covers the necessity of clean financial storytelling, the dangers of co-mingling personal and professional expenses, and how to identify "single points of failure" that scare away high-quality buyers. Craig Jamison shares his philosophy on de-risking, explaining why the best time to plant the tree of diversification was twenty years ago and the second best time is today. The unglamorous truth is that many owners are too "superstar-dependent," making themselves the secret sauce and the primary bottleneck of their own company. If the business cannot function without you in the building, its value at the closing table will plummet. You will walk away from this episode with a clear framework for auditing your customer concentration and a blueprint for a three to five year exit runway that maximizes your final multiple. If you care about building long-term legacy, regional growth in Northwest Arkansas, and transition planning, you’ll get a lot from this. Please Subscribe and Share this episode with a fellow founder. What is the one task in your business today that only you can do, and how soon can you delegate it to someone else?

  6. May 4

    Owner to Owner Podcast Introduction: Teaching the Strategy of the Exit

    Send us Fan Mail Most owners wait too long to think about their exit, turning a potential legacy into a high-stakes gamble. Transitioning a business requires more than just a buyer; it’s about the intersection of personal wealth, risk management, and market timing.  In this podcast we'll sit down to explore the mechanics of de-risking your portfolio and the impact of tax mitigation on your net proceeds. Join us as we dive into the specific philosophy that a business must be managed as an asset, not just a job, highlighting the "aha" moment where personal wealth and business health finally align.

  • 6 Episodes

Ratings & Reviews

5
out of 5
3 Ratings

About

Building a business is a marathon, but crossing the finish line requires a specialized strategy to protect the legacy you’ve built. This owner-to-owner forum connects Northwest Arkansas entrepreneurs with the veteran CPAs, financial advisors, and fellow business owners who understand the realities of value, transition, and deal structure. Through practical, experience-based conversations, we bridge the gap between building a company and successfully navigating its sale. Tune in to gain the actionable insights and local expertise needed to turn your years of hard work into a seamless, high-value exit.

Information

  • Creator
    Cameron Geiger
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Clean
  • Copyright
    © 2026 Owner to Owner
  • Show Website
    Owner to Owner