My First Deal: What I Learned About Guiding Sellers and Buyers

Every broker remembers their first deal. Mine taught me more about the real work than any textbook could—and reminded me why clarity and steady guidance matter more than clever strategies.

The Background

As a former Contract Negotiator and Acquisition Specialist working in the Department of Defense, I thought I knew deals. I was comfortable with negotiations, complexity, risk analysis, and pushing for outcomes. But business brokerage is different. My job isn't to own the decision—it's to help buyers and sellers see their options clearly and move forward with confidence.

That first deal tested everything I thought I knew.

What Went Wrong (And Right)

Midway through the sale, a fire broke out at the business property. The building was nearly 100 years old, and the insurance company initially said the policy didn't cover code upgrades—a potential deal-breaker. The sellers had to bring in a public adjuster. Fortunately, the upgrades were covered, but then the insurer started advising the seller not to sign anything until the claim fully closed.

At first, I thought more transparency with the insurer might help move things along. I was wrong. Inviting the wrong parties into deal conversations can give them power to stall or derail everything. I learned to be much more careful about who gets a voice in the process.

The deal also involved three sellers who took over a month to respond to the buyer's offer because they couldn't align internally. That delay nearly cost them the sale—only the buyer's patience saved it.

Then there was the financing hiccup. The buyer initially chose a major regional bank that wasn't SBA-preferred and got declined. We quickly pivoted to a known SBA lender in our network who got it approved.

What I Did Right

I listened more than I talked. I stayed calm when everyone else was stressed. I realized these aren't just transactions—they're life transitions. Sometimes what clients need most isn't an answer, it's someone who will sit with the uncertainty and help them think through their options.

I also learned to lean on my network. My mentor, insurance contacts, and trusted lenders all brought expertise I didn't have. I've come to appreciate that aspect of the work—letting experts be experts while I focus on keeping the process moving.

What I'd Do Differently Now

I'd set clearer expectations upfront. That means preparing both sides with a simple roadmap: what to expect, what's expected of them, and how delays impact everyone. A basic "deal readiness" conversation could have prevented weeks of confusion and stress.

I'd also be more direct about decision-making roles early on. If there are multiple owners, they need to align on price, terms, and timeline before we go to market—not after an offer arrives.

For Future Sellers

Preparation matters more than perfect timing. Know what you will and won't negotiate on before you list. If you have business partners, have the hard conversations about expectations upfront.

Be careful about bringing third parties into the deal too early. Every additional voice can slow things down. If they need to be involved—CPAs, attorneys, insurers—let's define their role and keep scope from creeping.

A good broker doesn't just find buyers. We protect your timeline, your confidentiality, and help you avoid costly detours.

For Future Buyers

Know your numbers, but also know your non-negotiables. Time for training, vendor transitions, lease transfers—these all impact value and timeline.

If you're buying solo, define your best offer and backup plan before you submit. If you're in a partnership, align internally first.

Choose your lender carefully. Your broker can suggest proven options, but we can't make the decision for you. The right lender relationship can save weeks and prevent costly false starts.

That first deal closed successfully, but it took longer than anyone wanted and created more stress than necessary. The lessons stuck with me: clear process, qualified participants, and steady communication prevent most problems. When issues do arise, having the right team and staying focused on solutions keeps deals moving forward.

Every seller's situation is different, but the fundamentals remain the same: prepare well, communicate clearly, and trust the process to work.

Ready to explore your options? Contact us today to discover how our confidential guidance for business owners across Oklahoma City, Tulsa, and throughout Oklahoma can help you navigate your exit with clarity, protect your legacy, and avoid the costly delays that derail other deals.