Hey!

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

Last week, I told you about how I pivoted from banking software to insurance and why that three-inch manual changed everything for my business.

But stories are only valuable if you can extract principles you can use.

Today, I want to give you the framework I wish I'd had back in 2004—the system for recognizing when it's time to pivot, how to evaluate opportunities, and how to execute without killing your existing business.

📒 DEEP DIVE

The Framework That Saved Me From Chasing Bad Opportunities

How to evaluate whether you're looking at a genuine opportunity or just getting bored with the grind of building your current business.

My insurance pivot wasn't luck. Looking back, I can see clear patterns that made it work. More importantly, I can see why other "opportunities" I considered over the years would have been disasters.

Here's the 3-part framework I use now to evaluate whether an opportunity is worth pursuing or just a distraction.

Part 1: Warning Signs It's Time to Consider a Pivot

Before you start chasing new opportunities, you need to honestly assess whether your current business has run its course. Not every plateau means you should pivot—sometimes you just need to execute better.

Market Signals:

• You've picked all the low-hanging fruit in your current market

• Sales have been declining or stagnant for over a year despite your best efforts

• You consistently lose deals to "we'll wait for our current provider to build this"

• Major technology changes are making your current approach obsolete

Customer Signals:

• Your Net Promoter Score is consistently low despite improving your product

• Customer churn is above 10% monthly (you're replacing your entire customer base every 10 months)

• Customers complain frequently about fundamental aspects of your service, not just features

Capacity Signals:

• You have the skills and bandwidth to take on something new

• You're not at 100% capacity with current revenue-generating activities

• An opportunity appears that's adjacent to your current expertise

The key insight from my banking experience: When I visited those credit union CEOs, they weren't complaining about our product. They just fundamentally didn't want to be early adopters. That's a market signal, not a product problem.

Part 2: The Opportunity Test

Not every new opportunity is worth pursuing. Before you make any moves, the opportunity should pass these three tests:

The Market Test:

• Is this an underserved or completely unserved market with real demand?

• Do these customers have money and the ability to pay?

• Is word-of-mouth strong in this industry? (Tight-knit industries are goldmines)

In insurance, I could see that small carriers had been ignored by technology companies. They had cash flow from their business model. And everyone knew everyone—one happy customer would become ten prospects overnight.

The Skill Test:

• Can you become competent enough in this domain within days or weeks, not months?

• Does this leverage your existing technical or business skills?

• Are the potential customers willing and able to teach you what you don't know?

I didn't need to become a licensed insurance agent. I just needed to understand their quoting process well enough to automate it. That's a learnable technical problem, not a fundamental business model change.

The Economics Test:

• Can you see a clear path to making significantly more money for the same or less effort?

• Is the total addressable market bigger than your current one?

• Can your existing business fund this transition?

The insurance market was massive compared to small credit unions in Missouri. And the customers were willing to pay upfront, which solved our cash flow problem immediately.

Part 3: How to Execute Without Killing Your Business

Here's where most founders mess up. They think pivoting means stopping everything and starting over. That's not a pivot, that's just starting a new business with extra steps.

Smart execution comes down to 5 key principles:

1) Don't Stop the Revenue Engine

Keep your current business running while you test the new opportunity. I kept doing network administration work while building the insurance product. This gives you runway and reduces risk dramatically.

Don't rush into immediately replacing all your revenue. The goal is to test whether the new opportunity can eventually become bigger than your current one.

2) Start With Intense Learning

When you find a real opportunity, become obsessively focused on understanding that industry. Read everything. Talk to everyone. Treat learning like your business depends on it—because it does.

I didn't just skim that insurance manual. I read every page, took notes, looked up terms I didn't understand. I treated it like studying for the most important exam of my life.

3) Get Paid to Learn

Structure early deals so customers are invested in your success. We had that insurance company prepay 50% because we needed the cash flow and they needed to feel committed to the project's success.

Don't work for free while you figure things out. Get customers to pay you to solve their problems, even if you're learning as you go.

4) Leverage Tight Networks

Industries where everyone knows everyone are perfect for new entrants. One happy customer becomes ten prospects overnight. Focus on making your first customer so happy they become your best salesperson.

In tight-knit markets, reputation travels at the speed of gossip. Make sure that gossip is good.

5) Test With Real Stakes

Don't just talk about pivoting, take actual contracts and deliver real value. The market will tell you quickly if you're onto something.

When agents across Missouri started bragging about our software at conferences, we knew we had product-market fit. That's not something you can fake or manufacture.

When to Pull the Trigger

You'll know it's time to fully commit to the pivot when:

• The new opportunity is generating more revenue than your old business

• You're consistently hitting capacity constraints trying to serve both markets

• The growth trajectory of the new business is clearly better than the old one

For us, that moment came when we had more insurance work than we could handle while our banking customers were still saying they'd wait for their current providers.

The decision was obvious at that point.

The best pivots don't feel like pivots when you're doing them. They feel like natural expansions into markets that desperately need what you're building.

If you have to force it, convince yourself it makes sense, or ignore obvious red flags—you're probably chasing a distraction, not pursuing an opportunity.

But when you find that underserved market where customers have money and real problems you can solve? When word-of-mouth spreads faster than you can keep up with demand?

That's when you know you've found something worth pivoting toward.

🎙 EPISODE OF THE WEEK

Firing someone is one of the hardest parts of leadership—but avoiding it can cost your business even more. In this episode of Build Your Business, Matt and I break down how to fire someone the right way: with clarity, compassion, and professionalism.

Whether it's your first time or you're trying to improve your process, you'll learn how to prepare, communicate, and protect both your team and your business.

Check it out: Spotify | Apple Podcasts | YouTube

BEFORE YOU GO…

Every successful founder I know has at least one pivot story. The ones who build lasting companies don't just have grit. They have the wisdom to recognize when that grit should be redirected.

Your current business might be good. But good isn't the goal when there's a great opportunity sitting right in front of you.

The framework I've shared today will help you tell the difference.

Use it wisely.

Talk soon,

Chris.