• Mon, Aug 04, 2025
  • Top 4 Questions Baby Boomer Business Owners Should Ask Before Deciding to Sell Their Business and the Role of a Business Broker
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  • Retirement should be a celebration, yet for many baby boomer business owners, letting go of and selling the business they have built often sparks considerable uncertainty and confusion.  If you fall into this category, you are not alone and do not have to navigate this transition on your own.  A seasoned business broker is not just a matchmaker for buyers and sellers; they strategically guide you from uncertainty to clarity in the sales process.  To help you get started, this article will discuss the top 4 questions to ask before deciding to sell your business and how a business broker will assist you through the sales process.

    Question 1: Am I Personally Ready to Step Away?

    Selling your business is not just a financial decision; it is an emotional one.  Ask yourself:

    • Can I envision my life without running my business?
    • What aspects of ownership will I miss the most?
    • What impact will selling have on my family?
    • What do I hope my legacy looks like after I sell?


    Talk openly with loved ones and trusted advisors. Your emotional clarity sets the foundation for a successful business sale.

    Question 2: How Much Do I Need Financially to Retire on My Terms?

    The proceeds from the sale of your business may be a large or small portion of your overall retirement fund.  Ask yourself:

    • What net proceeds do I need from the sale of my business to achieve my financial goals?
    • Are there tax strategies I should consider before a sale?
    • What deal structure helps maximize both upfront payout and long-term benefits?


    A business broker, along with your CPA and financial planner, can help you model scenarios and align deal structure to your financial goals.

    Question 3: How Much Involvement Am I Willing to Offer After Closing

    Buyers typically expect a specified amount of unpaid transitional assistance after closing to ensure a smooth transition.  Ask yourself:

    • Am I willing to stay on after the initial unpaid transition assistance for compensation?
    • If so, for how long, what compensation, and what responsibilities am I willing to undertake?


    When contemplating this, consider the impact it will have on your lifestyle after closing, the possible future success of your business, as well as the deal structure.  Here are some things to consider:

    • No involvement after closing offers freedom quickly, but may reduce the sale price if a buyer perceives business stability or knowledge transfer risks in your absence.  In addition, to mitigate this risk, a buyer may require seller financing or an earnout as part of the deal structure.
    • While involvement will require your time after closing, it offers steady compensation. Also, if the deal structure includes an earnout, you may earn more if the agreed-upon projected numbers are met with your continued assistance.  It also builds buyer confidence and smooths customer and employee retention.


    Know your boundaries up front. It will affect how your business is marketed, and the deal structure is negotiated.

    Question 4: Who Is My Preferred Buyer?

    Your buyer might not look like you. Common buyer types include:

    • Individual Entrepreneurs: Relocating professionals, career changers, or first-time business owners drawn to the freedom and excitement of entrepreneurship.
    • Strategic Acquirers: Competitors or suppliers seeking growth and cost-saving synergies. They may be willing to pay a premium for a business they perceive as a great fit.
    • Financial Buyers: Private equity firms, family offices, or investment groups targeting businesses with scalability or recurring revenue.


    It is important to discuss these buyer types with your business broker. Your business broker can tailor outreach based on which buyer type best fits your industry, business size, growth profile, financial goals, and legacy desires.

    Selling Is a Journey — Do Not Go It Alone

    Retirement is a major life pivot. Selling your business should support your retirement, honor your legacy desires, and give you peace of mind. A seasoned business broker brings objectivity, discretion, and experience to:

    • Guide you through the entire sales process
    • Establish a realistic valuation
    • Prepare a Confidential Business Review of your business
    • Market your business in a compelling, confidential manner through appropriate channels
    • Qualify buyers
    • Negotiate a favorable deal structure
    • Close your business with confidence

    They help to ensure your sales journey is smooth, structured, and aligned with your goals.  You have built something remarkable. Let the sale of your business and your retirement be just as fulfilling with expert guidance every step of the way.  If you are considering selling, contact an Edison Business Advisors team member and receive expert assistance.