The Time I Made a Client Cry

Jun 26, 2026 | Commercial Insurance and Business Growth

A small business owner talking on the phone while reviewing complex business insurance contract requirements at a desk.

Traditionally, making your clients cry is probably not considered a good way to start a business relationship.

But years ago, I had a phone call with a woman in West Texas that I still remember to this day, and honestly, I probably always will.

She was starting a small janitorial business completely from scratch. Her goal was to clean apartments, handle make-readies, and do cleanup work for apartment complexes in her area. This was not some large operation with investors and endless capital behind it. We are talking about a very small business owner trying to build something for herself, probably looking at around $50,000 a year in revenue at best starting out.

The problem was not finding work.

The problem was getting insured properly so she could take the work.

She had landed an opportunity that was bigger than anything she had ever had before, but the contract required specific insurance coverages and policy structures that she could not seem to get anyone to help her with. She had spent over a month calling different insurance agencies, programs, and carriers in her area trying to get it figured out. Every conversation kept leading to another dead end.

At that point, she was running out of money, running out of time, and honestly running out of hope. She was getting ready to walk away from the entire thing because without the insurance requirements being met, she could not move forward with the contract.

To this day, I still do not know how she got my direct number. She was in West Texas and I was over here in the Houston area, but somehow she found her way to me.

We started talking.

Within about 45 minutes, we had everything handled.

The policy structure was corrected, the requirements were met, and she was finally in a position to move forward with the contract and officially launch her business. We were wrapping up the call, getting ready to hang up, and all of a sudden she just starts sobbing.

Now if you know anything about me, if you start crying, there is a decent chance I am about to start crying too. I do not even necessarily need to know why yet. It is just how I am wired.

So naturally, now we are both emotional on this phone call.

Before we hung up, she told me something I have never forgotten. She said:
“You were my last call. I was getting ready to give this up completely. I prayed and asked God to send me somebody that could help me get this done, and He sent me you.”

At that point, I am definitely crying harder than she is.

That was probably the first real “make them cry” moment I ever had in this business, and it stuck with me because it reminded me that insurance is not just paperwork and policies. Sometimes it is the thing standing between somebody and the dream they are trying to build.

Why Small Businesses Struggle to Get the Right Insurance

A lot of small business owners, especially in smaller towns or rural areas, run into situations exactly like this more often than people realize.

It is not always because they are uninsurable.

Many times, the issue is:

  • The contract requirements are complicated
  • The business is new
  • The operation does not fit neatly into standard underwriting boxes
  • They are working with agencies that do not fully understand the industry
  • The business owner does not know how to explain their operations correctly to carriers
  • Cash flow is tight while trying to meet contract requirements

We see this constantly with contractors, janitorial companies, small service businesses, startups, and growing operations trying to land larger commercial contracts. The work is there. The opportunity is there. But the insurance requirements can become the roadblock keeping them from moving forward.

That is one of the reasons we take such an advisory approach at The Koch Insurance Group. Our role is not simply to provide quotes. Our role is to help business owners understand risk, structure coverage properly, meet contractual requirements, and position their businesses to grow responsibly.

Insurance Should Help Businesses Grow, Not Hold Them Back

One of the things I love most about this business is helping protect the people behind the company. There is something incredibly rewarding about helping somebody move from uncertainty and frustration into a position where they can finally move forward with confidence.

That does not mean every situation is easy. There are times when businesses are simply not structured correctly yet, or the risk is too high, or the coverage needed is going to be expensive. Sometimes those conversations are difficult too.

But when we can help somebody protect what they are building and create opportunities they thought were slipping away, those are the moments that stick with you.

Where The Koch Insurance Group Serves

The Koch Insurance Group proudly serves businesses throughout:

  • Houston
  • Spring
  • The Woodlands
  • Conroe
  • Magnolia
  • Tomball
  • Montgomery County
  • Greater Texas

We are also licensed in 18 states and work with multi-state operations depending on coverage needs, including:

  • New York
  • California
  • Oklahoma
  • Florida
  • Utah
  • Colorado
  • And more..

As our licensing footprint continues to expand, we are able to help businesses operating both locally and across multiple states structure commercial insurance programs that align with their operations and growth goals.

Let’s Talk About Your Business Goals

If you are struggling to meet contract insurance requirements, unsure whether your current coverage is structured correctly, or trying to position your business for growth, we are happy to have a conversation.

Sometimes all it takes is somebody willing to slow down, understand your business, and help you navigate the process correctly.

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