Step 1: Are You Ready to Sell?

Most owners assume readiness is just about the business — tidying up financials, grooming successors, or boosting EBITDA. But true exit readiness has three dimensions, and if any one of them is missing, your deal is at risk.

1. Business readiness: Is your company attractive to buyers? That means strong governance, transferable value drivers, and financials that hold up under due diligence.
2. Personal readiness: Are you prepared for life after the sale? Do you have a financial plan, estate plan, and a vision for how you’ll spend your time once you’re no longer in the driver’s seat? Have you communicated with your spouse and family members about what comes next?
3. Market readiness: Is the timing right? You can run a great company and be personally ready to step away, but if the economy or your industry is in a downturn, it may pay to wait — or to tweak your expectations.

Even with so many owners planning to exit within the next decade, only 42% of Gen Xers and 25% of Baby Boomers actually score as “ready” across these three dimensions.³ That’s a massive gap — and it’s why the first step in exit planning is taking a clear-eyed look at your readiness.

It may sound elementary, but put pen to paper and document what you want to happen. Here’s a simple hypothetical:

• Net at least $25 million after taxes to secure retirement
• Pay off the vacation home mortgage
• Fund down payment for three kids’ homes
• Ensure key employees stay with the business post-sale
• Free up time to serve on nonprofit boards

That’s it. Five bullet points. Not a 40-page plan — just enough clarity to guide initial decisions and keep everyone aligned on what a successful exit means for you.

Step 2: What’s the Value of Your Business?

That’s not an easy question to answer off the cuff. But you shouldn’t plan an exit without knowing what your business is worth. Yet, only 60% have had their business formally valued in the last two years.⁴

A back-of-the-napkin evaluation can only take you so far. That’s a dangerous way to make the biggest financial decision of your life. Instead, a formal valuation accomplishes two things:

1. While only going to market will truly tell you what the market will bear, a skilled valuation professional can give you a more realistic picture of what a buyer might pay.
2. It highlights the gap between what you think your business is worth and what the market is willing to offer.

A valuation can help you identify areas to increase your company’s value, such as strengthening recurring revenue, diversifying customer concentration, or optimizing your infrastructure to be more cost-efficient.

Bottom line: Get a defendable fair-market valuation now, and if you have a fast-growing company, consider updating it every 12–24 months. Up to 80–90% of the average business owner’s net worth is tied up in their businesses,⁵ so you owe it to yourself (and your family) to know what it’s really worth and how you could grow that number before you sell.

Step 3: How Can You Increase Your Business’s Value?

A Business valuation tells you where you stand today. Needless to say, it doesn’t have to be the final number. Most businesses have untapped potential that can be unlocked with the right value enhancement initiatives.

Think of it as pre-due diligence. By de-risking the business, optimizing operations, and bolstering your intangible capital, you can potentially make your company more attractive (and, in turn, more valuable) to buyers.

Common tactics include:

• Expanding recurring revenue streams
• Reducing customer or vendor concentration
• Documenting processes and governance
• Building out a robust management team
• Cleaning up financial statements

Yet most owners skip this step. In fact, nearly 80% of Baby Boomer owners and more than a third of Gen X owners have never completed a value enhancement or pre-transition due diligence project.⁶ That’s leaving money on the table.

In addition to a potentially more lucrative business sale, these initiatives can also create a stronger, more resilient company in the meantime — one that produces more income for you today and is ready for transition whenever the timing is right.

Step 4: Have You Thought About Succession Planning?

A buyer isn’t just purchasing your balance sheet. They’re buying confidence that the business will thrive without you. That’s where succession planning comes in.

Ask yourself:

Who steps into your role?

Is there a second-in-command ready to lead, or will a buyer worry the business is too dependent on you?

What incentives (equity, stay bonuses, career paths) are in place to keep your best people from walking out the door after the sale?

If this is a family business, have you communicated openly about who wants (and is qualified) to lead next?

These aren’t easy questions, but they do need answers — because succession planning is really value insurance. It reassures buyers (or the next generation) that your company’s revenue, relationships, and culture aren’t trapped in your head.

Businesses with documented succession plans are more attractive, command higher valuations, and better positioned for a smooth transition.

Step 5: What Are Your Exit Options?

Once you know what your business is worth, the next question is: How do you actually want to exit?

There are many types of exit strategies. Each option comes with tradeoffs in control, timing, and after-tax proceeds. The most common include:

Third-party sale: Selling to a strategic buyer, private equity firm, or family office. Often delivers the highest valuation, but also means relinquishing control.

• Third-party sale: Selling to a strategic buyer, private equity firm, or family office. Often delivers the highest valuation, but also means relinquishing control.
• Management buyout (MBO): Selling to your leadership team or other stakeholders. Keeps continuity but may require creative financing.
• Employee Stock Ownership Plan (ESOP): A tax-advantaged structure that rewards employees while creating liquidity for you.
• Family transition: Passing the family business to a child or other relative. Legacy-driven, but complicated by tax and governance issues.
• IPO (Initial Public Offering): Rare, but an option for larger businesses with growth trajectories.
• Liquidation: Shutting down and selling assets. Typically a last resort, but sometimes the cleanest path.

Interestingly, preferences are shifting. According to the Exit Planning Institute, while Baby Boomers lean toward third-party sales, younger Gen X and Millennial owners are increasingly favoring internal exits, such as ESOPS and family transfers.⁷

Don’t lock yourself into a single path too early. Keeping options open lets you adapt to market conditions, buyer appetite, and your personal goals, as they evolve.

Step 6: Who’s on Your Transition Team?

A business sale shouldn’t be a one-man show. That’s an enormous amount of stress and decision-making responsibility on one person’s shoulders. The stakes are too high, and the expertise needed is too broad. All business owners should have a bench of trusted advisors who can cover the financial, legal, and strategic planning angles — and who can coordinate with one another instead of working in silos.

At a minimum, that means:

• Financial Advisor: To quarterback the process, design advanced planning strategies, model post-sale cash flows, and align the deal with your personal and family goals.
• CPA: To partner on tax strategies and keep the IRS from being your largest “shareholder.”
• Attorney: To structure the deal, protect you legally, and negotiate terms.
• Exit Planning Advisor (often a CEPA): To help drive business improvements that increase valuation multiples and make your company more attractive to potential buyers.
• Investment Banker or M&A Advisor: To understand an owner’s end goals, then manage the complex process of taking a business to market, including identifying qualified investors, as well as negotiating and structuring financial terms to ensure the best outcome for the business owner.

Depending on your situation, we may also recommend estate planners, insurance specialists, and other transaction specialists for optimal outcomes.

Recent studies show that financial advisors have emerged as the most trusted advisors across generations of owners.⁸ That’s good news — but it also means your advisor needs to step up as the coordinator, making sure every professional at the table is working toward your defined vision of success.

The worst-case scenario is building a “dream team” of professionals who don’t talk to each other. That’s how strategies slip through the cracks, value gets left behind, and exits unravel. The best-case scenario? An integrated team, aligned around your readiness, your financial goals, and your legacy.

Step 7: What Are the Tax and Estate Implications?

As much of a windfall as it can produce, a business exit is a major tax event. Depending on how you structure the deal, the IRS could walk away with a sizable chunk of your proceeds. And if you haven’t updated your estate plan, your family may inherit an unenviable tax bill.

That’s why tax and estate planning shouldn’t be an afterthought. They need to be baked into your exit strategy from day one. Key considerations include:

• Capital gains taxes: How will the sale be structured — stock sale or asset sale — and what does that mean for your after-tax proceeds?
• Entity structure: Is your business organized in a way that maximizes tax efficiency?
• Gifting and trusts: Should you transfer ownership interests before a sale to minimize estate taxes or fund generational wealth?
• Charitable strategies: Donor-advised funds or charitable trusts can allow you to give strategically while reducing tax liability.

Only 41% of Baby Boomer owners have updated their estate plan in the past two years.⁹ That’s a glaring blind spot given that, for most owners, the business represents the vast majority of total net worth.

Step 8: Execute Your Business Exit Strategy

Whether you’re an entrepreneur with an ambitious startup or a long-time business owner that’s ready to pass the reins to your child, at some point, planning must give way to action.

Execution is where all the pieces come together. And it’s also where the process can feel overwhelming. The moving parts multiply, the meetings pile up, the stakes rise, and decisions need to be made quickly — with precision.

You don’t need to shoulder that alone. At Simon Quick, our job is to simplify the process, keep the moving parts connected, and make sure every decision circles back to what matters most to you and your family. We’re here to quarterback the situation and be the steady hand when the process feels anything but steady.

If you want a more grounded perspective on your exit strategy, schedule a complimentary meeting. One conversation could change your life.