There are two common questions that most business owners ponder at some point in time:
- When should I sell my business?
- Am I really ready to sell my business?
At some point in time, it will be time to hand over the keys to a competitor, a private equity firm, or the next generation of your family.
For many owners, this transition can occur faster than expected; possibly triggered by health issues, changing markets, or simply the fatigue of carrying the weight of ownership.
Today, 49% of business owners say they plan to exit within the next five years, and 75% within the next ten years¹. The vast majority of owners don’t have a formalized business exit plan. Even more sobering, approximately 75% of privately held businesses never actually sell². They often end up closing their doors or liquidating, leaving owners with far less than they had imagined.
This is where the services of an experienced CFP ® in San Antonio who specializes in business exit planning can be of great value to you. If you own a business generating more than $1 million in EBITDA, those odds are not acceptable. The question isn’t whether you will exit, but how well-prepared you will be when it happens, which our article will explore in more detail. Link
The Reality Check: What’s at Stake
Imagine this: you get a call from a competitor or investor expressing interest in buying your company. At first, you’re excited. However, the due diligence request then follows. They may request three years of clean financial records, proof of recurring revenue, contracts, and compliance documentation. They question margins, customer concentration, and growth potential.
Could you hand over a package today that would withstand that scrutiny? If not, you’re not alone. Many owners assume their business is “ready enough,” only to discover gaps that slash valuation; or worse, kill the deal.
The numbers confirm the risks:
- Most business sales take six to 12 months to close³, meaning last-minute fixes aren’t realistic.
- Valuations vary widely by industry; for instance, manufacturing companies often sell for around 5 times EBITDA, while faster-growth sectors can reach much higher multiples⁴.
- And even when deals close, 75% of owners expressed feeling regret within a year of selling, often because they were unprepared emotionally for life after the sale.⁵
A business sale shouldn’t focus solely on the financials. After years of building something meaningful, the real goal is to carry that value forward, protecting your wealth and the legacy that comes with it.
Listen: Business Exit Planning: Essential Steps for a Successful Transition.
The Moving Pieces: Why Business Exits Are So Complex
Selling a business isn’t like selling a house. A buyer isn’t just purchasing assets. They’re buying future cash flows, relationships, people, and systems. That makes the selling process uniquely complicated.
Here are four key challenges every owner must navigate:
- Timing the Market
Markets matter. Interest rates, buyer appetite, and industry consolidation can all influence whether you receive strong offers or muted interest. But here’s the catch. You can’t predict the market. What you can do is prepare your business so that when conditions are favorable, you are prepared to act. - Valuation Realities
You may have a valuation number in your head that you believe your business is worth. But remember that your valuation depends on what the buyer sees. While strategic buyers may pay more for synergies, financial buyers often benchmark their offers against multiples. Without preparation, you may run the risk of disappointment if an offer doesn’t match your expectations. - Operational Readiness
Deals often die in diligence. Missing contracts, unclean books, or overreliance on the owner can spook buyers. Preparing systems and people in advance can mean the difference between a smooth transaction and a failed one. - Personal Transition
One of the most overlooked parts of selling your business: who will you be after the sale? Many owners underestimate the extent to which their identity is tied to their business. That’s why regret rates are so high. You need both a comprehensive financial plan that outlines a roadmap for your financial future, but you also need a personal plan that will help you define how you want to focus your time.
Listen: “Building and Selling an Empire with Brian Booker.”
The Legacy Question: More Than Just a Check
Think about this for a moment. What happens the day after the wire transfer hits your account?
- Will you know how to manage a sudden influx of wealth?
- Will you have clarity about how you’ll spend your time?
- Will you feel proud of the way your employees and customers are treated after the transition?
These aren’t abstract questions. They are the very issues that determine whether you walk away fulfilled or join the majority of owners who regret the way their sale turned out.
Protecting your legacy isn’t just about extracting value. It’s about ensuring the story of your business ends well, for you, your family, and those who helped you build it.
PAX’s Business Pivot Planning: A Structured Approach
Over the years, PAX noticed a significant gap in how business owners prepare for an eventual exit. Most owners either wait too long to plan, rely solely on tax or legal advice, or only start thinking about a sale when they’re already ready to step away. By then, options are limited, value may be left on the table, and the transition can feel rushed.
To address this, PAX developed Business Pivot Planning (BPP): a practical framework designed to help owners strengthen their businesses, evaluate their options, and be prepared when the right opportunity arises.
It provides you, as the owner, with a straightforward, structured approach to consider the financial, operational, and personal factors involved in selling a business, rather than leaving it to chance or timing.
With PAX’s BPP process, you can:
- Assess Readiness: Gain a clear understanding of where the business stands today: financially, operationally, and personally, so you know what’s working and what may need attention.
- Spot Hidden Risks Early: Identify common deal-breakers such as tax issues, weak records, or operational gaps long before you enter a negotiation.
- Create Flexibility: Strengthen your business so you’re prepared to act when conditions are favorable, rather than feeling boxed in or rushed.
- Plan for Life Beyond the Business: Align exit timing, family considerations, lifestyle goals, and wealth planning to support the next phase of your life.
BPP gives owners the clarity and structure to approach a future transition with more control, so when the right moment comes, you’re not just hoping it works out. You’re ready. Our team of San Antonio financial planners can help you develop a customized BPP that clearly outlines your financial priorities.
PAX’s What You’ll Learn in This Six-Part Series
This article marks the beginning of a six-part series for San Antonio business owners who plan to sell within the next three to five years and want to prepare effectively. Here’s what you can expect in the upcoming articles:
- The 7 Landmines That Sink Business Sales: Common mistakes that cost owners millions
- Timing Is Everything: When to Sell Your Business: How to balance personal readiness with market conditions
- Strategic vs. Financial Buyers: What It Means for You: Why knowing your buyer changes everything
- Staying Clear-Headed in the Heat of the Deal: Managing the emotions of letting go
- From Owner to Investor: Thriving After the Exit: Building a meaningful second act
Each article will tackle one dimension of the exit journey, providing perspective, data, and practical considerations that you can implement.
Ready to Build a Strategic Exit Plan?
Selling a business isn’t just a financial event; it’s a life transition. The sale itself is only one part of the equation. What you do before, during, and after the transaction will determine how well you and your family benefit from the value you’ve built.
PAX Financial Group helps business owners create a comprehensive and strategic exit plan that covers every stage of the process, from preparing the business for a strong sale to managing the proceeds and planning for the next steps.
When you partner with PAX, you gain a team that will help you:
- Strengthen the Business Before You Sell
Improve readiness, reduce risks, and build value so you enter the process with a competitive advantage. - Coordinate the Transaction and Financial Strategy
Align tax, investment, and estate decisions with your exit goals so the deal structure supports your long-term interests. - Invest Proceeds with Purpose
Turn the sale of your business into a long-term wealth plan that fits your lifestyle, income needs, and family priorities. - Create Your “Life After the Business” Plan
Clarify how you want your time, identity, and wealth to support the next chapter, whether that’s a new venture, family focus, or a different kind of freedom.
The goal isn’t just to sell your business. It’s to help you transition on your terms with clarity, confidence, and a plan that supports the life you want after the deal is done.
If you’re thinking about a sale in the next three to five years, now is the time to start planning. PAX can help you take the proper steps today to create more options for tomorrow. Connect with our team of financial advisors in San Antonio.
References
Exit Planning Institute, State of Owner Readiness Report, 2023
InvestmentBank.com, “Only 30–40% of Businesses Actually Ever Sell,” 2024; GAP Advisors, “The Cost of Failure,” 2024
BizBuySell, Insight Report, 2024; BusinessBroker.net, Market Data Report, 2023
GF Data, Industry Valuation Report, 2024
Exit Planning Institute, Owner Regret Study, 2023
