The Ins and Outs of Selling a Business

The Ins and Outs of Selling a Business

By Keith Dee, Osage AdvisorsBusiness
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The Ins and Outs of Selling a Business episodes

  • The Market is Uncertain, But Your Strategy Shouldn’t Be

    We’ve been getting the same question over and over: “Should we be selling right now?”

    The market is uncertain, and there’s no clear direction—but that doesn’t mean you should hit pause. In this video, we share why we’re advising most clients to stay the course, continue marketing, and monitor buyer activity.

    There’s still capital on the sidelines—and real opportunities for well-positioned businesses.

     

    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    7 min
  • The Secret Business Value that Everyone Ignores

    As business owners, our brand is everything. It’s not just a logo or a tagline — it’s an extension of who we are. We pour years into building, refining, and protecting it. But there’s one critical piece that often gets overlooked: employee branding.

     

    In this episode, we’re joined by Alyssa Gelbard, founder and CEO of Point Road Group — a leading expert in employee and executive branding. Alyssa shares powerful insights on how your team represents your business both inside and outside your company walls — and why that matters, especially when you’re thinking about growth, leadership, or a future sale.

    Whether you're grooming your company for acquisition or simply want to strengthen your brand from the inside out, this conversation will change the way you think about your people and the power of their personal brands.

     

    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

     

    20 min
  • The Never-Ending Deal
    WHEN WILL THIS END?

    Ah, the question every dealmaker asks at some point. M&A deals will hit walls—unexpected delays, emotional sellers, nervous buyers, financing hiccups, diligence curveballs. It’s part of the process.

    But here’s the key: don’t panic. Don’t rush. Don’t lose sight of the goal.

    The best advisors don’t just close deals—they guide clients through the rough patches with strategy, calm, and a relentless focus on the end game.

    So when your deal hits a wall (and it will), remember: setbacks are temporary. The right team keeps things moving.
    8 min
  • How Your Business Legacy Impacts Its Sale

    Legacy plays a crucial role in the sale of a business. Beyond valuation, owners must consider their company's brand, culture, and employees when transitioning to new ownership. In today's episode of 'The Ins and Outs of Selling a Business,' with Andrea Brown of Frequency 110 we discuss the importance of planning for leadership succession, retaining key employees, and ensuring a smooth transition. Join us as we explore how business owners can leave a lasting impact while maximizing their company's value.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    21 min
  • How Stay Bonuses Keep Deals on Track

    Navigating stay bonuses for key employees can be a critical part of the M&A process. Ensuring clear communication and early planning can help avoid internal conflicts that might impact the deal. In today's episode of 'The Ins and Outs of Selling a Business,' we discuss strategies for structuring stay bonuses and how they can influence a successful transaction.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    9 min
  • Why Owners Struggle to Step Back from Their Business

    Shifting from working in your business to working on your business is key to scaling and building long-term value. Business owners often struggle with letting go, but developing a strategic mindset and empowering a strong leadership team can make all the difference. In today's episode of the Ins and Outs of Selling a Business, we're joined by our guest, Andrea Brown of Frequency 110, to explore how business owners can create a sustainable company that thrives beyond their direct involvement.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    20 min
  • Why Environmental Due Diligence Matters in M&A

    Environmental issues can be a major hurdle in business transactions, especially for manufacturing companies. Delays in addressing concerns can extend closing dates, drive up costs, and complicate negotiations. In today's episode of 'The Ins and Outs of Selling a Business,' we discuss how environmental due diligence impacts deals and why proactive planning is key.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    9 min
  • What Business Owners Don’t Know About Exit Planning

    Successful business sales don’t end at the closing table—what happens next is just as important. Business owners need a clear strategy to manage their wealth, avoid seller’s remorse, and plan for long-term financial security. In today's episode of The Ins and Outs of Selling a Business with our guest Richard Dvorak of Discovery Point Wealth Advisors, we talk about post-sale transitions, wealth management, and the critical steps to ensure a successful transaction.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    23 min
  • How Real Estate Can Make or Break Your Business Sale

    Real estate plays a crucial role in business sales, and addressing it early can make all the difference. From lease agreements to sale options, sellers need to evaluate how real estate impacts their deal structure and financials. In today's episode of  The Ins and Outs of Selling a Business, we explore key strategies for handling real estate in M&A transactions to ensure a smooth closing.


    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    7 min
  • How a Financial Quarterback Guides Business Owners

    Successful business exits require planning, just like a great quarterback leads a team to the Super Bowl. Business owners need a clear strategy to maximize value, minimize taxes, and ensure a smooth transition. In today's episode of The Ins and Outs of Selling a Business with our guest Richard Devorak of Discovery Point Wealth Advisors, we talk about financial planning, tax considerations, and the key steps business owners should take to prepare for a successful exit.

    Contact Keith: Osage Advisors, LLC

    osageadvisors.com

    860-767-3273

    20 min

About The Ins and Outs of Selling a Business

From the publisher's feed

This podcast taps the expertise of Keith Dee, President and CEO of Osage Advisors, with more than 30 years of experience advising business owners and families of midsize companies and helping them…

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