Are You Outgrowing Yourself?

You found product-market fit. Customers are buying, revenue is growing, and you've even raised a fresh round of funding. Congratulations—now you're facing an entirely new set of problems.

If you’re leading a growing company, see if any of these symptoms sound familiar:

• Your team often makes the wrong decisions when you’re not in the room. You step away from a project you thought was on track, and when you check back in, you’re shocked by the direction it took.

• Decision-making is slowing down. What used to take a Slack message now requires three meetings. Your once-nimble team feels bureaucratic.

• You can’t attract or retain great people. Top candidates pass on your offers, or your best people leave for opportunities that “felt like a better fit.”

• You know you need to grow as a leader, but have no idea when or how. Every article says you need to “work on your business, not in it,” but you’re drowning in urgent fires.

If you’re nodding your head, you’re not alone. And you’re not failing.

You’re experiencing what we call the Post-Product-Market-Fit Paradox.

The Paradox: What Got You Here Won’t Get You There

Here’s the brutal truth: The scrappy, do-whatever-it-takes approach that got you to product-market fit will actively hurt you in the next phase.

The habits that made you successful—being in every decision, moving fast and breaking things, hiring people you know—these are now bottlenecks. You need to transform from entrepreneur, to CEO. From doer, to leader. From having all the answers, to building a team that can find the answers without you.

Most founders try one of four paths to figure this out:

1. Trial and error - Learning by making expensive mistakes with real money and real people. A Series A buys you runway, not infinite attempts.

2. Find a good mentor - Great mentors are incredibly valuable, but they’re needles in haystacks. And even the best mentor only sees snapshots of your journey.

3. Look for a peer group - CEO peer groups can be powerful, but ad hoc groups usually fade without professional facilitation. And good luck finding one where others are at your exact stage.

4. Read books about founder heroes - You read about the beginning (scrappy startup) and the end (IPO or acquisition), but you’re stuck in the messy middle where the real transformation happens.

None of these are bad. They’re just insufficient.

What’s Coming: A System for the Messy Middle

Over the next several months, we’re publishing a series of deep dives into the system we’ve built working with dozens of founders through this exact transition. This isn’t just theory. It’s the playbook that’s behind some of Silicon Valley’s biggest success stories, and it works just as well outside of tech.

Here’s a preview of what we’ll cover:

• Ownership Culture - The core framework for building a team that thinks and acts like owners, making great decisions independently. This is the foundation that makes everything else possible.

• High-Performance Meetings - How to make every meeting move the needle instead of draining energy. (Hint: Spend way less time on reporting and more time preparing to make good decisions.)

• Hiring and Retaining World-Class Talent Without Breaking the Bank - This new approach, proven by our clients, lets you find the best talent, regardless of their background or resume, without taking all your time or budget. This is how you actually build diversity as a strength, not a checkbox.

• Replicating Yourself - Creating a developmental culture that grows more leaders like you, so you’re not the only one who can make tough calls.

• Surviving the Journey - How to ride the dragon of growth without falling off, getting burned, or getting eaten alive. We’ll dig into the emotional and psychological tools for the founder rollercoaster.

Each post will combine high-level analysis with tactical steps you can implement immediately. No fluff, no theory for theory’s sake—just what works.

Writing in Public: You Can Shape This Book

Here’s the thing: We’re not just writing a blog series. We’re writing a book, in public, in real-time. And we want your input.

If you’re experiencing these pain points, this series is for you. Over the next year, we’ll dissect each of these founder challenges with the same practical approach you’d expect from The Great CEO Within, Scaling People, or High Growth Handbook—short, actionable, immediately applicable.

But here’s where it gets interesting for you:

You can be in the book.

We’re looking for real questions, real challenges, and real “I’m stuck on this” moments from founders like you. Here’s how it works:

1. Share your question - Comment below or DM us with a specific challenge related to these pain points (or anything else you’re wrestling with).

2. Get real help - We’ll try to answer you directly, and you might get some free coaching out of it.

3. Get featured - We may include your question (anonymously if you want) in a call-out section in a future post or in the book as a real-life example. Your struggle might be the exact case study another founder needs.

The topics above are part of our working draft, but your feedback will shape what we write and how deep we go on each topic.

What to Do Next

Subscribe to our Substack to get each new post delivered to your inbox. We’re publishing weekly, starting now.

Comment or DM with your most pressing challenge right now. What’s the one thing that keeps you up at night as a founder? We’re listening, and we might be able to help.

Share this with another founder who’s in the messy middle. The post-PMF paradox is lonely. Let’s fix that together.

The path from entrepreneur to CEO is learnable. You don’t have to figure it out alone through trial and error. Over the next year, we’ll show you exactly how.

Welcome to the Ownership Culture series. Let’s build something great.