Hey!

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

After my private equity deal with my previous company, I had a moment that hit me like a truck.

For the first time in 15 years of building my company, I realized something painful: I wasn't the right person to lead it anymore.

That was hard to swallow. I'd been thinking "I'm killing it" for so long that I never saw my limitations coming.

Here's what I learned about recognizing when you've hit your ceiling as a founder—and what to do about it.

📒 DEEP DIVE

Why I Wasn't the Right Person to Run My Company Anymore

My private equity deal forced me to admit I'd reached my level of incompetence. Here's how I figured it out.

Nobody wants to admit they've reached their limit. I certainly didn't.

For 15 years, I was convinced I was the perfect person to run my company. Growth was strong, we were making progress, and everything seemed under control.

Then the private equity deal happened.

That's when reality hit: there were people out there far better equipped to take my company to the next level than I was. It was the first time in my life that it was clear to me that I had risen to the level of my own incompetence.

It wasn't that I lacked the ability to learn. It was about efficiency. I would have to go through the painful, time-consuming loop of trial and error, while others had already walked this path and knew the patterns.

There's a reason private equity firms place professional managers in these roles. They're not looking for someone who might "rise to the occasion." They want someone who has done it five times before.

The Mistakes That Held Me Back

After the deal closed, I had plenty of time to reflect on what happened. What skills was I missing? How did I end up in this position? Could I have done anything differently?

This reflection led me to create a list of my shortcomings as we scaled—things I now recognize were holding both me and the company back. These weren't just small missteps; they were fundamental gaps that became more problematic as we grew.

Here's my list of things I got wrong so you don’t make the same mistakes:

I thought hiring the smartest people would solve everything

I believed if I just found the most brilliant minds, they'd figure everything out. They didn't.

Smart matters, but expertise and experience in specific areas matter more. I didn't understand how much "been there, done that" would matter to our growth.

I lost focus on profit margins and cash flow

As the company grew, the numbers started looking so big that they didn't seem real anymore. I started thinking, "There's plenty of money, everything will be fine."

Wrong. No matter how well your company is doing, you can never stop thinking about expense control and cash flow.

I didn't understand the key metrics

I was tracking lower-level metrics like NPS scores and product shipping timelines, but I missed the industry-standard metrics that matter in SaaS.

Take the "Rule of 40" for SaaS companies (combining growth and EBITDA profitability). This could have been our North Star, but I didn't even know to look for it.

My pricing strategy was weak

I avoided increasing prices because those are hard conversations to have with customers. The private equity team quickly identified this as an area where we were leaving money on the table.

I couldn't say no to customers

In the early days of a company, you rarely say no to customer requests. But that approach spreads you thin as you scale. I should have been more willing to say, "This is our roadmap, and we'll get to your request eventually."

I had no strategy for upgrading talent

As companies scale, the people who fought alongside you in the early days might not be the right ones for the next level. Having those difficult conversations—"You're awesome, but we need to bring in someone above you"—is painful but necessary.

This was true at every level, including myself. What works at 10 employees rarely works at 100.

I saw board management as a burden, not an opportunity

I viewed board management as just this pain in the ass that I had to deal with—not something that drove any value.

Yes, there's bureaucracy involved. Getting your board decks clean, making changes the board requests—it all feels like overhead. But in most companies, especially with private equity involved, you have this super powerful network of highly aligned, highly connected people. You can utilize these people to great benefit.

I couldn't see it because I was too much in the weeds of the everyday. "I don't have time to think about this board stuff because we have to solve this problem for this customer right now."

This was part of a larger problem that most early founders have. We wear so many hats to begin with, and it's hard to start taking those hats off and giving them to other people. If I had done that well, I think it would have been easier to have been in a better mindset when it came to managing the board.

The Hard Truth

The most painful realization wasn't that I needed to learn new skills. It was looking in the mirror and admitting: "You're not the right guy anymore."

That's devastating when it's your company—something you built from nothing.

But sometimes the best thing you can do for your company is recognize when you've risen to the level of your own incompetence. When you're no longer the person who can take it where it needs to go.

🎙 EPISODE OF THE WEEK

Feeling like you're carrying the entire business on your shoulders? You're not alone. In this week's episode of Build Your Business, Matt and I get uncomfortably real about the emotional weight of being a founder.

We dive into what isolation really feels like, the anxiety of endless to-do lists, and how becoming the bottleneck in your company affects everything from your business to your personal life.

Check it out if you've ever felt overwhelmed, disconnected, or stuck in the loop of overwork.

Listen wherever you listen to podcasts: Spotify | Apple Podcasts | YouTube

BEFORE YOU GO…

The thing that makes you a great founder in the early days might be exactly what holds your company back later on. 

The skills that got you to $1 million won't get you to $10 million, and the skills that got you to $10 million won't get you to $100 million.

Sometimes, the most courageous act of leadership is recognizing when it's time to step aside and let someone else take the wheel.

I learned this lesson the hard way. Hopefully, you won't have to.

Talk soon,

Chris.