Built a $100M Agency in 3 Years—Then It Went Bankrupt. Here’s What I Wish I Knew

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Ever dreamed of building a $100 million agency, selling for a massive payday, and seeing your name in headlines? It sounds like the ultimate win. But what happens when that dream starts to crack under pressure?

I’ve live through that and it fell apart fast. Not because we didn’t grow but because we skipped the hard stuff. The boring stuff. The stuff that no one talks about when you’re scaling fast.

If you’re an agency owner chasing scale, considering a sale, or wondering if your current path is sustainable, this is the truth bomb you need.

The Highs: Acquisitions, Headlines, and the $100M Mark

Let’s start with the dream. A few years ago, I was part of an agency that had a bold plan: acquire successful agencies (each doing $1M+ in EBITDA), pay half in cash and half in equity, and build a powerhouse primed for an epic exit.

And it worked… for a while.

• 10 agencies acquired

• Over $100M valuation

• $8M+ in EBITDA

But underneath the surface, cracks were forming. The fast growth masked deep structural issues.

The Downfall: Debt, Boardroom Drama & Chasing the Wrong Goals

The downfall wasn’t due to lack of revenue or bad acquisitions—it was bad decisions behind the scenes. Every new agency came with debt, and as soon as you start taking on debt, you commit to maintain a certain growth level with the banks, a pace that was frankly unsustainable.

To keep the bank away, we needed to keep buying more agencies. However, when board politics stalled future acquisitions, everything ground to a halt.

No growth = default = collapse.

The worst part was that founders who sold for a mix of cash and equity saw their second payday vanish. Why? Because they sold control—and lost the ability to steer the ship.

What We Got Wrong (So You Don’t Have To)

Let’s break down the key mistakes most agencies make when chasing fast growth—or a flashy exit:

• No Unified Vision: There was no clear post-acquisition mission across agencies. There was only focus on money and fast growth.

• No Specialization: Everyone was selling everything to everyone—no authority, no leverage.

• No integration team: Unless you fully integrate agencies across systems they won’t add as much value as you hope. Each agency continued to operate under separate slack channels, tools, separate chaos. They each stayed in their own lane and as a result it all felt like small businesses operating under one logo.

• No Standard Offerings: Each agency had its own pricing, tools, and processes.

• No Leadership Alignment: Power was handed to the wrong board members who didn’t share the vision.

As a result, it was impossible to scale sustainably.

The Right Way to Scale: Build Something You Actually Want to Keep

If you’re feeling stuck in your agency—juggling sales, delivery, hiring, and managing—it’s time to stop and recalibrate.

Start with this simple exercise:

• Draw a circle around your fist on a piece of paper.

• Outside the circle: list everything you hate doing in your agency.

• Inside the circle: write what you love doing.
  
  Now start building your team and systems around that, with c