Waiting for the Wrong Moment

Most founders think about investment bankers the way they think about estate lawyers. Something you call when the event is already happening. You decide to sell, and then you go find someone to run the process.

I understand the logic. Running a business takes every hour you have. Spending time on a relationship you might not need for three or five years feels like a distraction from the actual work.

But I have sat across the table from hundreds of owners over twenty-five years, and the ones who get the best outcomes almost never start the clock when they decide to sell. They started years earlier, without necessarily planning to.

What the Relationship Is Actually For

A banker who only meets you at the start of a process knows your company from a data room. Financials, customer concentration, growth rate, the story your CFO put together for the deck.

A banker who has known you for years knows something different. They know what you said about your business eighteen months ago and whether it happened. They know which competitors you watch and why. They know if you tend to be conservative in your projections or optimistic.

That difference matters more than people expect once a deal is actually underway. Buyers and their advisors are testing whether the story in the data room matches the person telling it. A banker who can speak to your track record with some history behind it is worth more to you at the table than one meeting you for the first time.

The Founders Who Get This Right

The owners I have watched build the most value did a few small things consistently, long before they were thinking about a sale.

They took the call even when they were not raising anything. Not every quarter, but often enough that a relationship existed instead of a name in a contact list.

They shared bad news along with good news. A soft quarter, a lost customer, a delayed product. Owners who only call when things are going well are easy to spot, and it teaches the other side to discount everything you tell them later.

They asked what a buyer would actually pay attention to in their market, and then paid attention to it themselves. Not to perform for an eventual buyer, but because a business run with that discipline tends to be a better business regardless of who ends up owning it.

What I Tell People Starting This Now

If you run a business and think a sale, a recapitalization, or an outside investment might be somewhere in your future, even five years out, my advice is simple. Pick one or two people you respect in the advisory world and let them get to know your business before you need anything from them.

You are not committing to work with them later. You are giving yourself the option to walk into a process with someone who already understands your numbers, your market, and your instincts, instead of someone learning all three under a deadline.

The Cost of Getting This Wrong

The founders who skip this step are not doomed. Plenty of deals get done on a compressed timeline with an advisor meeting the company for the first time. But I have watched those deals lose value in small, avoidable ways.

A buyer asks a pointed question about a bad year, and the banker has no context to help frame the answer. A negotiation stalls on a point that a longer relationship would have surfaced and resolved months earlier. The story told in the room does not quite match the person telling it, and experienced buyers notice.

None of this shows up as a single dramatic mistake. It shows up as a slightly lower price, a slightly harder negotiation, or terms that favor the other side just a bit more than they should have.

A Habit, Not a Transaction

Building a relationship with the people who might one day help you sell your business is not a task you complete. It is closer to a habit, the same way checking in on your industry or reading the same handful of podcasts every week becomes a habit. You do it because it keeps you sharp, and because when the moment actually arrives, you are not starting from nothing.

The best time to build that relationship was years ago. The second best time is now, before you think you need it.