Scaling a Digital Marketing Agency: My Path to Millions
Picture this: I’m standing in the middle of a bustling retail store, a colorful gift box in hand, pitching socks and handkerchiefs to a shop owner who looks mildly amused but mostly confused.
That’s where my entrepreneurial journey began—not in a sleek office or a high-tech startup hub, but knocking on doors, trying to sell products I’d sunk every penny into.
Scaling a digital marketing agency to over $500K a month wasn’t even a glimmer in my eye back then; I was just a 22-year-old with $30,000 in savings and a dream.
Fast forward a decade, and I’ve built not one, but three agencies—CSM Agency, Evolve Marketing, and Untold Creative—each thriving in its own niche.
It’s been a wild ride, full of missteps, breakthroughs, and lessons that I wish someone had handed me on day one.
Today, I’m pulling back the curtain on how I got here, from those early days of door-knocking to managing a team that serves global brands.
This isn’t just a story—it’s a roadmap for anyone who wants to turn their hustle into a scalable, profitable business.
So, grab a coffee, settle in, and let’s dive into the gritty, glorious reality of building a digital marketing agency that lasts.
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Table of Contents
The Humble Beginnings: From Socks to Strategy
My first taste of entrepreneurship wasn’t glamorous.
I’d moved back to Ireland from Austin, Texas, where I’d worked at a startup surrounded by brilliant consultants solving big problems.
Inspired, I teamed up with an old friend from my days at Dell, and together we launched Hidden Gent, a gift business for men.
We poured $60,000—our combined life savings—into socks, toys, and handkerchiefs, packaging them into sleek gift boxes we thought would fly off shelves.
Armed with samples from Turkey and a naive optimism, we hit the streets, pitching to retail stores across Ireland and the UK.
I can still feel the weight of those boxes as I walked into shops, my pitch stumbling out as I tried to convince owners to stock our wares.
We eventually landed in close to 100 stores, including big names like Arnotts, but every euro we made went straight back into the business—I never paid myself a cent.
It was a brutal lesson in cash flow: buying stock without a marketing budget left us scrambling, but it planted the seed for what came next.
The Pivot to Consulting: A Lifeline in Disguise
Hidden Gent was my crash course in resilience, but it wasn’t sustainable.
When COVID hit, purchase orders vanished overnight, and our €200,000 stockpile sat in a warehouse, unsold.
My business partner, older and with a family to support, walked away, and I couldn’t blame him—the business was dead.
But I’d been dabbling on the side, offering B2B lead generation consulting based on what I’d learned in Austin and at Dell.
My first client, Smart Accountants in London, paid me £2,000 a month to set up a system for them, and that small win lit a fire.
I didn’t call it an agency then—it was just me, hustling to pay bills while Hidden Gent crumbled.
Looking back, that failure was a blessing; it forced me to lean into consulting, where I could trade knowledge, not inventory.
From there, I teamed up with Tig, who ran Evolve Marketing, and we started building something bigger—something that would become a digital marketing agency powerhouse.
Scaling a Digital Marketing Agency: The Early Days
Our early days as an agency were chaotic but exhilarating.
Tig focused on Evolve Marketing, serving professional services like law firms and accountants, while I carved out CSM Agency, targeting B2B companies—SaaS firms, manufacturers, anyone needing leads.
We were scrappy, saying yes to every opportunity, fueled by that hustle mindset from my door-knocking days.
I’d sit with clients, sketching out strategies on napkins, promising results I wasn’t even sure I could deliver yet.
We grew fast—too fast—hitting €425,000 in revenue in November 2022, mostly from one-off website projects.
On paper, it looked like we’d made it, but behind the scenes, our team was drowning, overwhelmed by inconsistent workloads.
I remember late nights, scrambling to hire freelancers to meet deadlines, realizing we’d built a house of cards.
That spike taught me a hard truth: scaling a digital marketing agency isn’t just about revenue—it’s about structure.
The Game-Changer: Hiring a Managing Director
By early 2023, Tig and I were at a breaking point.
We were the bottleneck—spending hours micromanaging instead of steering the ship.
I’d be knee-deep in client strategies one minute, then sorting payroll the next, while Tig juggled his own chaos at Evolve.
We needed help, and not just another hire—we needed someone who’d done this before.
Enter Charie, our new Managing Director, a woman who’d scaled agencies like ours and knew how to take us from point B to C.
Hiring her felt like handing over my baby—I’d always thought the MD role was mine to keep—but it was the best decision we ever made.
She spotted flaws we’d missed: poor time tracking, sloppy organization, teams stretched too thin.
Suddenly, I could focus on growth—building sales teams, dreaming up new departments—while she ran the day-to-day, turning our mess into a machine.
The Handover: Letting Go to Grow
Bringing Charie on wasn’t a flip of a switch—it was a slow, messy handover.
I’d been most people’s direct report, so shifting them to her took time and trust.
Picture this: two agencies—CSM, laser-focused on performance marketing like lead gen and e-commerce, and Evolve, crafting brand perception for big law firms and construction giants.
Charie sat between them, managing departments across both, while Tig and I stepped back from the weeds.
At the same time, we hired a Strategic Director from VML, a global agency titan, to oversee client strategies holistically.
I’d catch myself slipping back into old habits—jumping into team calls, tweaking campaigns—but bit by bit, I let go.
Now, I’m working on the business, not in it, and it’s like breathing fresh air after years underwater.
Scaling a digital marketing agency means knowing when to release the reins—it’s scary, but it’s freedom.
Building the Ecosystem: Three Agencies, One Vision
Today, our ecosystem hums with three distinct brands, each with its own flavor.
CSM Agency pulls in €150,000 a month on retainers, a steady heartbeat after we ditched project chaos for consistency.
Evolve Marketing mirrors that, serving professional services with a focus on perception—think big legal firms wanting to look untouchable.
Then there’s Untold Creative, our six-month-old baby, born when my friend David joined us from Austin with a creative spark.
He’d worked at top agencies, and instead of going solo, we convinced him to build a department under CSM—UX design, web dev, branding, videography.
It grew so fast we spun it off into its own entity, projecting €2 million in revenue soon.
I see it like a garden: each agency a different plant, rooted in the same soil, growing toward our North Star.
Scaling a digital marketing agency this way keeps margins high and complexity low—less mess, more profit.
The Money Talk: Where We Stand, Where We’re Going
Financially, we’ve found our sweet spot.
CSM’s €150,000 monthly retainers feel sustainable—predictable cash flow, happy team, no burnout.
Evolve runs neck-and-neck, while Untold Creative’s project-based work could hit €2 million annually if we play it right.
Our North Star isn’t just numbers—it’s about building something sellable, an asset with enterprise value.
I don’t dream of a 100-person agency; I’d rather perfect this boutique model and plant seeds elsewhere—maybe tech, maybe something new.
Back in 2022, that €425,000 month was a fluke, propped up by a white-label deal with a massive accountancy firm.
They’d mark up our €50,000 website projects to €80,000, pocketing the difference, but we lost control of the client relationship.
Now, we’re focused on retainers over projects—steady growth over flashy spikes—because scaling a digital marketing agency sustainably beats chasing every deal that knocks.
Lessons from the Chaos: Saying No to Scale Smart
That 2022 spike was a wake-up call.
We’d say yes to everything—big projects, tight deadlines—until our team buckled and clients churned.
I’d lie awake, wondering how we’d deliver, while staff quietly burned out.
Post-crash, we doubled down on retainers, cutting project work from CSM and funneling it to Untold Creative.
It’s like pruning a tree: trim the wild branches, and the core grows stronger.
Saying no felt counterintuitive—after years of hustling, turning away money stung—but it saved us.
Now, our margins are better, our team’s happier, and we’re not just surviving—we’re thriving.
Scaling a digital marketing agency isn’t about size; it’s about stability.
The Secret Sauce: People and Partnerships
If I had to boil it down, the secret to scaling a digital marketing agency is people.
Early on, I leaned on consultants—smart folks I’d met in Austin or at Dell who’d solved big problems.
I’d sell their expertise, then build teams to deliver, bridging my gaps with their brilliance.
Think Vinnie O’Brien, who set up eBay’s Enterprise Division, or Josh Goldsmith, ex-HubSpot growth guru—guys who walked into sales calls and oozed authority.
Partnerships helped too: cold outreach to align with firms like TripleWhale gave us leverage with bigger clients.
It’s not just about your skill—it’s about who you surround yourself with.
I’d tell any agency owner pre-100K: find your niche, then find your people.
Scaling a digital marketing agency hinges on that combo—focus and firepower.
Selling with Strategy: The Consultancy Edge
Here’s where it gets fun: we sell through consultancy, not just services.
Imagine sitting across from a marketing director, their company turning over €10 million, sweating over a budget decision.
They don’t want ads—they want reassurance their money’s well spent.
I’d bring a strategist like Vinnie, map out a holistic plan (paid media? PR? affiliate?), then let our team execute.
Smaller businesses? Same deal—find a freelancer with a killer skill, pitch together, split the win.
It’s about solving macro problems, not just running campaigns.
That trust—built on strategy—closes deals and keeps clients long-term.
Scaling a digital marketing agency starts with selling solutions, not hours.
Mentoring the Next Wave: Why I Give Back
These days, I’m mentoring others through a project with Jordan, a guy whose agency I admire deeply.
Why? Because I love it—sitting with someone, sharing a coffee, helping them find their footing.
I’ve done it informally for years, even ran workshops for 1,200 businesses during Ireland’s Road to Recovery program.
Teaching digital strategy to small firms—how to nail customer experience or launch a site—felt like flow.
Jordan’s vision aligned with mine: a collective of doers, not gurus, building something real.
I’ve been burned by flashy courses that overpromise; this is different—it’s practical, proven, collective.
Helping others scale a digital marketing agency fuels me—it’s my way of planting trees for the future.
Scaling a digital marketing agency isn’t just my story—it’s theirs too.
The Golden Nugget: How to Hit 100K a Month
So, what’s the key to scaling a digital marketing agency to €100K a month?
It’s threefold: focus, people, and systems.
First, cut the noise—niche down hard, find your unfair advantage, and stick to it.
Evolve started with law firms; I stuck to B2B leads—distraction kills momentum.
Second, surround yourself with talent—consultants, partners, anyone who’s solved your client’s problem before.
Sell their expertise while you build the machine.
Third, master sales—cold outbound, strategic partnerships, events—whatever builds your pipeline with leverage.
Scaling a digital marketing agency to that first milestone is about clarity and connection—get those right, and the rest follows.
Conclusion: The Road Ahead
Looking back, I see a kid with a gift box, then a guy with a laptop, now a leader with a vision.
Scaling a digital marketing agency to where I am—three brands, millions in revenue—took grit, luck, and a lot of learning.
I don’t have it all figured out, but I’ve got enough to share: focus on what you’re great at, lean on brilliant people, and build systems that last.
My North Star? A sellable asset—maybe tech, maybe more—but for now, I’m content perfecting this boutique life.
If I can do it—socks to strategy—you can too.
Take the leap, find your tribe, and scale smart.
The journey’s messy, but the view from here? Worth it.
Scaling a digital marketing agency is less about size and more about impact—make yours count.
We strongly recommend that you check out our guide on how to take advantage of AI in today’s passive income economy.
