Smart Agency Masterclass with Jason Swenk: Podcast for Digital Marketing Agencies

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

Jun 3, 2025

Imagine building a $100 million agency, only to watch it collapse. The speaker reveals the highs of rapid growth, acquisitions, and big valuations. But lurking beneath were debt and poor decisions that ultimately led to downfall. Discover the hidden truths about agency scaling, the importance of clear vision, and why financial success isn't everything. This candid discussion provides valuable lessons for aspiring agency owners on navigating the treacherous waters of rapid growth.

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ANECDOTE

The $100M Roll-up Collapse

Jason Swenk was part of a roll-up strategy acquiring 10 agencies valued at $100M.
Despite growth, debt and board control issues caused the agency's failure and bankruptcy.

ADVICE

Prioritize Cash Over Equity

Always be wary of equity as part of your payment; it can become worthless.
Prioritize upfront cash because earn-outs and equity stakes aren't guaranteed.

INSIGHT

Money Focus Blinded Vision

Obsessing over money and valuation blinds agencies from meaningful purpose.
Lack of clear mission risks organizational disorientation and collapse.

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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 clarity instead of complexity. Most agencies don’t need more people, they need more focus.

You need clear goals, accountability, and owning your niche. Remember: generalists survive, specialists scale. The more specific your positioning, the faster you’ll grow.

5 Core Takeaways for Smarter Agency Growth

Build Around Your Zone of Genius Design your role around what you love. Delegate the rest.
Get Focused More people won’t fix chaos. Clear goals, roles, and offers will.
Own Your Niche Generalists survive. Specialists scale.
Productize Your Offer One clear offer. One repeatable outcome. One path to scale.
Don’t Chase the Exit—Build a Business You Don’t Want to Escape Freedom isn’t selling. Freedom is clarity, systems, and loving what you’ve built.

So if you're fantasizing about selling, slow down and ask yourself: Why? The grass isn’t greener on the other side—it’s greener where you water it.

So don’t just build to sell. Build to love what you’ve built. The right growth, the right systems, and the right people will make your agency unstoppable—and valuable, whether you exit or not.

Want the full playbook?

Grab a copy of Accelerating Your Agency and learn the exact framework behind sustainable, scalable, and enjoyable agency growth.