Creating a Business That’s Built to Sell

For most founders, their business is a cherished asset as well as their identity, purpose, income and legacy all intertwined. Yet one truth applies to every entrepreneur, regardless of industry or scale: one day, you will exit. The question is whether that exit will be the result of thoughtful, proactive planning or a rushed reaction to a sudden offer or unplanned life event.

A business that is truly “built to sell” isn’t defined by its valuation alone. It’s defined by clarity on what you need the sale to accomplish, what life looks like after the transaction, and how to structure the deal so it supports your family, your goals, and your next chapter. That clarity doesn’t appear at the last minute. It’s built well before a letter of intent hits the table.

Start with your life, not with the deal

Too often, business owners let market timing or headline valuations drive their decisions. But the sale shouldn’t dictate your life plan. Rather, your life plan should dictate the sale.

When you begin with a rigorous financial plan that defines how much you need on an after-tax basis to sustain your lifestyle, support the people you love and fund your goals, you can evaluate offers differently. You gain the ability to see beyond the top-line number and assess what really matters, like structure, timing, tax consequences, independence, future opportunity and emotional alignment.

Many owners are surprised by how dramatically a deal can shift once they understand what the sale must achieve. That clarity empowers stronger negotiation, smarter restructuring and far more confidence in the final outcome.

What really makes an offer “good”?

Before price ever enters the conversation, owners should define their non-negotiables.

What conditions must be true for you to feel emotionally aligned with the transition? For some, that means cultural continuity for employees or economic opportunity for the next generation of leaders. For others, it means freedom to define the next chapter, philanthropic opportunity or the ability to finally pursue a passion project.

A deal with the highest number isn’t always the best. The after-tax proceeds, timing of payouts, post-sale responsibilities, earnout risk and overall structure all contribute to whether a proposal actually supports your long-term vision. Clients frequently turn down higher headline offers in favor of more flexible, tax-efficient structures that better align with their goals.

Your personal priorities should be the lens through which every offer is evaluated.

What’s the most expensive mistake owners make?

The answer is waiting.

Owners often assume they’ll start planning when they are “ready to sell.” By then, the window has narrowed. Options shrink. Tax-smart strategies become limited. Deal structure becomes reactive instead of intentional.

Waiting too long can cost millions through unnecessary taxation, unfavorable structures or the emotional toll of choices made under pressure. And the consequences aren’t only financial. Many owners only realize after the fact how deeply the sale impacted their team, their family dynamics or their own sense of identity.

The strongest outcomes arise when planning begins years or even decades before an exit. Once a letter of intent is on the table, your flexibility compresses. So the best time to engage an advisor is long before you are fielding offers.

The right advisors do far more than react to a deal. They help shape it. They bring technical depth—valuation analysis, tax modeling, estate and charitable planning—and combine it with lived experience. At Corient, many advisors have gone through transactions themselves, giving them insight into the technical, emotional and psychological layers that numbers alone can’t capture.

Even when clients hit their “number,” many feel adrift if they haven’t prepared for what comes next. The right advisor helps clarify the future: What do you want life to look like after the sale? How do you want to spend your time? What impact do you want to have? These questions are as essential as any financial projection.

Tax planning: From reactive to strategic

Tax strategy is often treated as an end-of-deal scramble. But if addressed early, it becomes an optimization tool, not a defensive move.

Early planning allows you to explore entity restructuring, long-term capital gains positioning, charitable strategies, installment sales, trusts and gifting approaches that can materially alter your after-tax result. Even though early, proactive planning drives the greatest tax efficiency, there are still critical strategies to evaluate once an LOI is signed or during the transaction year, albeit with a more limited set of tools. We do not recommend following cookie-cutter tactics. You want an approach that reflects your goals, your timeline and the legacy you want to build.

Preparing for the psychological shift

Perhaps the biggest surprise is the emotional transition from owning a business that you control to managing a diversified investment portfolio you don’t control in the same way.

Good planning acknowledges that shift. Rigorous modeling, scenario testing and portfolio design can restore a sense of agency. Clients often discover that this next chapter can be just as purposeful, even if it looks very different from the entrepreneurial climb. The goal is not just financial readiness, but emotional grounding.

Your business is a lifetime achievement

Selling a business is not a transaction. It’s a defining life event. When approached with clarity, planning, and the right advisory team, it becomes a bridge that can take you from passion to purpose. Speak with a Corient Wealth Advisor early in the process. Your future self will thank you.

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