Life Doesn’t Wait

Why Waiting to Prepare for the Sale of Your Business Can Cost You

Business owners often tell me they’re not ready to sell yet. The truth is that most people aren’t. Unfortunately, life and the market rarely wait until you feel ready. It’s like trying to time the stock market: You don’t know when private equity appetite, strategic buyer interest, or multiples will be in your favor. You also can’t predict when life events will force your hand.

The only real solution is to always be preparing for an exit. That way, if an opportunity arises or circumstances change, you’re ready to sell on your terms — not when you are forced to, taking a discount.

Why Waiting is Dangerous

Readiness is a vague concept. Is it about age, about hitting a revenue target, about fatigue? Markets and life events don’t care how you define it, but when owners wait until they “feel ready” under any definition they give up control, because the last minute is the most expensive and least effective time to prepare.

Multiples and buyer appetite change constantly. Compressing the three to five years most professionals say it takes to get a company truly ready into just one year means corners are cut, bills pile up, and value is left on the table.

Preparation takes years, not months. Waiting to plan your exit comes at the cost of lost leverage, higher fees, and a weaker outcome — or worse.

The Five Curveballs You Can’t Control

Most business sales are not planned. They are forced by one of the five Ds:

Death. An owner passes away, leaving a surviving spouse with no liquidity. One client’s widow was supposed to receive buyout proceeds for financial security. Following a costly and poorly managed sale under duress, she ended up taking two jobs before eventually living only on Social Security.
Divorce. A partner suddenly needs to liquidate their stake, destabilizing the company. Prenups, shareholder agreements, and updated operating agreements can help, but most owners never plan for it.
Disability. A health crisis prevents an owner from working. Without disability income or overhead insurance, there’s no replacement salary and the business still has to cover expenses.
Distress. Market downturns, supply chain shocks, or external crises create stress that owners cannot control.
Disagreement. Partners who once aligned fall out. Without updated agreements, disputes end up in court and erode business value.

Some of these scenarios can be de-risked by planning for things like death and disability. Others cannot be prevented, but you can prepare so they don’t destroy value.

The Cost of Being Unprepared

When owners wait until the last minute, professionals are forced into crisis mode. Attorneys, CPAs, and insurance providers charge more when everything must be rushed. And sometimes, what you need is no longer available at any cost:

You may not qualify for life or disability insurance after a health event.
Some legal elections, once made, cannot be undone. Routing stock into an irrevocable trust, for example, is permanent.
Once the IRS sees certain structures, you cannot “unring the bell.”

All this means that preparing your business for a sale is not optional. It’s the only way to avoid expensive mistakes and limited choices.

Creating Optionality

Optionality gives you peace of mind and power of choice. It’s not about selling tomorrow; you’re not locked into selling, but you could if you wanted or needed to. It is about having the freedom to sell when the timing is right, instead of being trapped in a crisis with no leverage. Here’s how to build the optionality you need:

De-risk the business. Make sure the foundation is secure.
Know your wealth gap number. Understand what you need to walk away securely.
Grow transferable value. Once the risk foundation is strong, work with a value advisor to increase what the business is worth without you.
Check in annually. Each year, ask: Do I want to sell? If yes, you are prepared. If no, no problem — just go back to building more value.

The Owner’s Reality

Most owners believe they’ll choose when to sell, but the five Ds make that decision for many. By preparing now, you can avoid panic, protect your family and employees, and keep control of your outcome.

You only get one shot at selling your business, and preparation puts you in a position of strength whenever you choose (or circumstances force you) to sell.