— SEPTEMBER 13TH, 2026 —

THE HARD MONTHS LEAD TO HARD LESSONS

I’ve had months where I hated my company. That’s a strange thing to admit when I’ve spent years talking about helping founders build companies they’ll love forever. But I’ve come to understand that those two things aren’t contradictory.

Building a company you love doesn’t mean loving every minute of building it.

I’ve learned that the months I feel like I hate my company are usually telling me something. I’m spending too much time in work I thought I’d handed off, or I’m avoiding a hard conversation I already know I need to have. That feeling of frustration I get isn’t random.

My instinct is to do what I can to make the feeling disappear. Reorganize, change the strategy, find something else to fix. But I’ve gotten better at resisting that temptation and looking more closely at what the frustration is trying to tell me.

When I look back at the months I hated, something had usually changed that I was still trying to handle the old way. The company had grown, but I was still relying on my own effort to make up for what wasn’t working. And more often than I’d like to admit, I was part of the problem.

Read more in I’ve Had Months Where I Hated My Company — Here’s What It Taught Me.

Growth changes what our companies need from us and from the people we lead. We don’t always recognize that change right away.

So, when running your company starts to feel harder than it should, what’s that feeling trying to show you?

PERSPECTIVES

“You will either step forward into your growth or you will step back into safety." — Abraham Maslow

MARK MY WORDS

There’s a pattern I’ve seen as companies move through the Stages of Development. Somewhere around 1, 3, 10, 30, 100, and 300 people, the way the company needs to be led changes.

Someone can be exceptional at one stage and have a hard time with what the next one asks of them. I’ve made the mistake of working around that for too long, taking on parts of their role rather than having the conversation we needed to have. But if you do that for too long, you can build yourself into the workaround.

The hardest months of running Ninety have taught me that most of the time, it comes back to a conversation I’ve been avoiding.

Have the conversation. You may be surprised by what becomes possible once everything is finally out in the open.

ONE MORE FOR THE ROAD

In case you missed it, here’s more from Founder’s Framework:

How to Run a Better Weekly Leadership Meeting in Under 90 Minutes

Our weekly leadership meeting had 17 people in it, and we finished in under 90 minutes. That’s because we got clearer about what belongs in the meeting and what doesn’t.

Here’s how we decide which issues need the Senior Leadership Team’s time and which ones are better handled somewhere else.

[Read Now]

Sometimes the hard months are the ones that show you what you couldn’t see before.