Sometimes I'll hear from business owners, "I'm probably three to five years away from selling." It suggests there is plenty of runway, no urgency, and time to get around to the details later. But in my experience, if you are three to five years from a sale and you have not started preparing, you may already be behind.

Liz MacRae, a serial entrepreneur who has both bought and sold businesses and now co-founds a platform helping people acquire them, joined me recently on The Cash Rich Exit Podcast. When I asked her for her fun, frank advice, she did not talk about maximizing valuation or finding the perfect buyer. She said: do your research, and start early. And then she added - if you think you are three to five years away and you have not done anything yet, you could already be behind the eight ball, especially when it comes to tax.

She is right. And the reason she is right gets to the heart of a misunderstanding about what exit preparation actually involves.

Most owners imagine that selling a business is an event. You decide to sell, you find an advisor, you find a buyer, you sign the papers. In that mental model, preparation is something you do in the months leading up to the transaction - tidy the books, put together a package, and go to market. But the reality is that the decisions with the biggest impact on your outcome are the ones made years before the sale, not months. And once you are inside that final window, many of those decisions are simply no longer available to you.

Consider the tax dimension alone. The way you own your business, the structure you hold it in, whether you have taken steps to multiply access to the capital gains exemption, whether you have the right holding company and family structures in place - these are not things you can retrofit the month before closing. Many of the most powerful tax strategies require a runway of two years or more to be effective. If you wait until a buyer is at the table, you have foreclosed on options that could have saved you a significant amount of money. I have seen founders leave hundreds of thousands of dollars behind simply because they started the conversation too late.

Then there is the operational side. If your business is dependent on you, if your financials have small errors that erode a buyer's trust, if your customer relationships live in your head rather than in contracts, these are all fixable - but they take time to fix. You cannot build management bench strength in ninety days. You cannot clean up three years of messy books overnight. You cannot document processes and reduce your own indispensability on a compressed timeline without the strain showing. The businesses that command strong valuations are the ones where this work was done gradually, deliberately, and early.

And there is the matter of understanding your own value. Liz made a point I found especially practical. She encouraged owners to research how companies like theirs are actually valued - and noted that with tools like modern AI assistants, you can do more of that homework yourself than you once could. But she offered it with a caution I want to echo: not every comparable is truly comparable. It is easy to hear that a business in your industry sold for a certain multiple and assume yours is worth the same. It rarely works that way. What matters is understanding the methodology - how value is actually determined in your sector, for a business of your size, with your particular mix of strengths and risks. Because that understanding is what allows you to know whether now is the right time to engage an advisor, and what you would need to change to move the number.

What surprises people most, and is genuinely good news, is that advisors do not mind if you are three to five years away. In fact, the good ones welcome it. A quality advisor is happy to spend time with an owner who is years out from a transaction, because that is precisely when their guidance is most valuable. That is when there is still time to build value, sequence changes, address dependencies, and put tax structures in place.

This is exactly why I offer a Wealth Gap Analysis, and why I encourage owners to come to me long before they think they need to. The analysis is not a sales pitch for a transaction that is about to happen. It is a map. It shows you the gap between what your business is worth today and what you need personally to fund the life you want after the exit. And critically, it shows you that gap while there is still time to do something about it. If the number is not where it needs to be, we have years to close it - through growth, through structural changes, through the deliberate work of making the business more valuable and less dependent on you. If you wait until the exit is imminent, that gap becomes a fixed constraint rather than a solvable problem.

If this resonates - if you are starting to think about your eventual exit, even distantly - the best thing you can do is begin the conversation now. Interview advisors. Understand your value. Get your structures reviewed. And give yourself the gift of time, which is the one asset in an exit that you cannot manufacture later.

Book a one-on-one Wealth Gap Analysis with me, and let us look at where you stand today and what the next three to five years could make possible. Reach out on LinkedIn, Colleen O’Connell-Campbell, or email me.

TTFN (ta ta for now)

Colleen O'Connell-Campbell

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