Hey!

Chris here. Welcome to Blueprint—the newsletter to help you build a winning engineering team.

Most founders think they need to stick with their original idea no matter what. That staying the course shows commitment and vision.

I used to think that, too.

Then I learned the difference between persistence and stubbornness the hard way.

Today, I want to tell you about the pivot that changed everything for my first company—and why the best opportunities often come disguised as distractions.

📒 DEEP DIVE

How to Pivot When Your Current Market Stops Growing

The story of how I went from network administrator to insurance software founder by saying yes to something I knew nothing about.

Back in 2004, I was making $40,000 a year as a network administrator for credit unions in Missouri. Decent money for the time, stable job, comfortable life.

But comfort wasn't the goal.

My cousin Phil and I had started building something on the side. He handled the design, and I did the coding. We were creating e-statement software for banks and credit unions—taking all those paper statements and putting them online.

The business was making some money, but not enough for me to quit my day job. I was living off my salary and reinvesting everything from the side business back into growth.

Then came decision time.

I needed to know if this e-statement business had real legs, or if I was just playing around with a hobby that generated beer money.

So I did what every founder should do when they're unsure about their market: I went directly to the customers.

The Road Trip That Changed Everything

I took three days off from my network admin job and visited every single customer I was already supporting. 

I pitched each CEO personally. Explained how our e-statement product was saving other credit unions serious money. Laid out all the economics, showed them the time savings, and demonstrated the customer satisfaction improvements.

Their response was unanimous: "We'll wait until our current providers offer it."

That hit me like a brick wall.

These weren't early adopters. They weren't even mainstream market. These were laggards—the type of customers who wait for everyone else to prove something works before they'll consider it.

The problem wasn't my product. The problem was that I was trying to sell innovation to people who fundamentally don't buy innovation.

I went home feeling like I'd just discovered my first business was probably going to cap out at hobby-level revenue.

When Opportunity Knocks, Answer the Door

A week later, one of the few CEOs who had implemented our e-statement product called me with something interesting.

She sat on the board of a small insurance company in Nixa, Missouri. They were struggling with their technology and needed help. She asked if I would be interested in a meeting.

At the time, I knew absolutely nothing about insurance. 

The extent of my insurance knowledge was writing checks for my car insurance and hoping I never needed to use it.

But I said yes anyway.

Phil and I drove to Nixa and walked into a world I'd never seen before. These people were speaking a completely different language—talking about rating tables, loss ratios, underwriting guidelines, premium calculations.

It was like someone had dropped me into a foreign country where everyone was really friendly, but I couldn't understand a word they were saying.

Here's what I could understand though:

• Their technology was ancient. We're talking systems that looked like they belonged in the 1980s.

• They had money. Insurance companies don't just collect premiums—their entire business model is investing that money while they hold it. Cash flow wasn't their problem.

• The market was completely underserved. In 2004, online quoting for small insurance carriers basically didn't exist.

• Everyone in the industry knew each other. This was a tight-knit community where word-of-mouth traveled fast.

So when they asked if we could help them build a quoting system for their agents, I did what any reasonable person would do.

I told them I could become an insurance expert in three days.

The Three-Inch Manual

They handed me their agency quoting manual.

This thing was a monster—easily three inches thick. Dense, technical insurance mathematics. Rating tables that showed how distance to a fire hydrant changed your rate. Deductible calculations. Interpolation formulas. Coverage types I'd never heard of.

Words that were completely foreign to me.

But I had one advantage: I was 24 years old with no kids and unlimited energy.

I went home, put on my headphones, and read that manual cover to cover without stopping. I treated it like my business depended on it—because it did.

Was I an insurance expert after three days? Absolutely not.

Did I understand 10X more than I knew three days earlier? Absolutely.

More importantly, I understood enough to know what questions to ask. And this customer was incredibly helpful—they wanted to teach, and I wanted to learn.

Building in a New World

Phil and I spent the next two months building their quoting system. Just the two of us, no other employees, working around the clock.

Since we didn't have cash flow, but we had the skills, we structured the deal so they prepaid 50% upfront. In their mind, that was half the total cost. In our mind, that was our living expenses while we figured out how to build something we'd never built before.

The system went live, and their agents across Missouri started using it immediately.

But here's the thing about tight-knit industries: when something works, everyone knows about it within weeks.

Their agents started talking about this new online quoting system at industry conferences. Other small insurance companies started calling us. The phone wouldn't stop ringing.

We went from zero insurance customers to having more insurance work than we could handle in about three months.

Meanwhile, our banking customers were still saying they'd wait for their current providers to build something similar.

So we made a choice. 

We discontinued the e-statement product entirely—not because it failed, but because we were completely out of capacity and the insurance opportunity was exponentially bigger.

The Lesson That Changed How I Think About Business

Looking back, that pivot taught me the most important lesson of my entrepreneurial career:

The difference between a good opportunity and a great opportunity isn't the size of the market or the amount of money involved.

It's the speed at which you can create value for customers who desperately need what you're building.

In banking, I was trying to convince conservative customers to adopt new technology ahead of their comfort zone.

In insurance, I was solving urgent problems for customers who had been waiting years for someone to build what they needed.

Same skills, same team, same work ethic. Completely different results.

That's the power of finding the right market at the right time with the right solution.

🎙 EPISODE OF THE WEEK

Are you stuck doing everything yourself because no one else can do it "right?"

In this episode of Build Your Business, Matt and I break down why perfectionists struggle with delegation—and how to fix it.

Learn how to build trust, communicate expectations clearly, and use systems that protect your standards without burning you out. We cover the delegation ladder, how to turn team members into owners, and finally free yourself up to focus on what truly matters.

Check it out: Spotify | Apple Podcasts | YouTube

BEFORE YOU GO…

The hardest part about recognizing opportunities isn't spotting them—it's having the courage to act when they don't look exactly like what you planned to build.

I thought I was going to be in the banking software business. Instead, I stumbled into insurance and built something much bigger than I originally imagined.

Sometimes the best thing you can do as a founder is stay curious about markets you don't understand and be willing to learn new languages when the right opportunity presents itself.

Next week, I'll share the framework I use to evaluate whether an opportunity is worth pursuing—and how to execute a pivot without destroying the business you've already built.

Talk soon,

Chris.