The $100K lessons I wish I knew before starting my first agency
When I launched my first agency back in 2014, I thought I was ready for everything. Turns out, I was ready for exactly... nothing.
Eight months of grinding, working 12+ hours a day, no salary, paying for an office just because “you’re supposed to have one”, and taking on projects I had no clue how to deliver.
The result? Slow growth, zero systems, and more sleepless nights than I’d like to remember.
Looking back now, I can see exactly what went wrong - and more importantly, how I could have saved myself years of struggle and over $100,000 in wasted opportunities and mistakes.
That’s what this article is about.
If you’re running a web studio, digital agency, or any service-based business, there are predictable traps you’ll face at each stage of your growth. And the sooner you spot them, the faster you’ll scale - without burning out or going broke.
In this series, I’ll break down the 4 key stages of agency growth, the mistakes most founders make in each one, and the exact systems you need to escape the trap. We’ll start today with Stage 1 - the messy, exhausting, exciting early days from $0 to $40k/year.
Why This Matters
If you’re stuck in Stage 1, you’re probably:
Doing everything yourself - sales, delivery, client support, admin
Struggling with inconsistent cash flow and unpredictable projects
Wondering if you should go all in or keep a side income
Burning way too much time on low-value tasks
I’ve been there. And I’ve helped other founders escape it much faster than I did.
So here’s what I wish someone had told me when I was starting out...
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Stage 1: The $0–$40K Hustle
What Stage 1 Really Looks Like
You’re at the very beginning. No systems. No processes. No brand recognition. Right now, you’re essentially a freelancer with a business name.
Most founders in this phase say “yes” to almost any project just to get cash flow. That’s exactly what I did. One of my first jobs was a $500 website. The client asked, “Can you do it?”I replied, “Of course!” - without actually knowing how to deliver it at the level they expected.
Result? Weeks of stress, late nights, and barely breaking even. Sound familiar?
The Biggest Mistake at Stage 1
Jumping all in without:
Knowing your product or service inside out
Having a repeatable sales process
Understanding which clients are worth your time
There’s a popular mantra: “Burn the boats.”Quit your job. Go all in. The problem? If you’ve got family, bills, or financial obligations - this advice can sink you before you even start.
The Real Cost of Stage 1 Mistakes
Stage 1 errors don’t just drain your bank account - they drain your momentum.
Without systems, you:
Spend 80% of your time inside client work instead of growing the business
Struggle with unpredictable income
Risk burning out before you ever hit a sustainable pace
How to Win in Stage 1
1. Keep a Safety Net
If possible, maintain part-time work or another income source while growing your agency. This lets you pick projects strategically - not from desperation.
2. Prioritize Long-Term Revenue
Switch from one-off projects to recurring income models:
Monthly retainers for marketing or automation services
Ongoing support contracts
Ad management agreements
3. Choose a Scalable Service Model
From my experience:
Web dev studios are hardest to stabilize - projects end, you start over
Automation agencies are easier - clients often pay for ongoing maintenance
Ad agencies can be the fastest to scale recurring revenue
Stage 2: $50K–$150K - The “Chief Everything Officer” Trap
You’ve made it past the fragile startup phase. You’ve got clients, revenue is flowing, and for the first time, you’re not panicking about how to pay next month’s bills. But here’s the catch: you’re still the one holding the whole business together.
I remember when I first hit this stage.It felt like a victory - finally making more than I had at any previous job. But the celebration didn’t last long. Every single day, I was buried in sales calls, answering client messages at midnight, putting out fires with the dev team, and personally chasing invoices.
It wasn’t that I didn’t have people on my team. I did. The problem was - nothing worked without me.
If a client had a complaint? They came to me. If a deadline was at risk? I was the one jumping in to “save” it. If a new lead came in? I was on the call, writing the proposal, and following up myself.
At first, I told myself this was normal - “That’s what a founder does.”But deep down, I knew it wasn’t scalable. I wasn’t building a business. I was building a prison with my name on the door.
The Hidden Danger of Stage 2
Most founders stay here for years without realizing it’s a trap. The business looks healthy from the outside, but inside it’s dangerously fragile:
If you get sick, revenue stops.
If you take a week off, projects stall.
Every new client means more hours for you, not just the team.
This is where burnout begins to creep in. You work more than ever, but growth slows down.
I learned this the hard way when I took a short vacation. Within three days, I was back on calls from the hotel lobby, fixing delivery issues. My “break” cost me more energy than staying in the office.
The Shift That Changes Everything
The only way out is to stop being the “Chief Everything Officer” and start building systems that can replace you in the day-to-day.
For me, the turning point came when I hired my first real operations manager. Not a virtual assistant. Not a “project helper.”Someone who could actually run the delivery process without my constant input.
At first, it felt risky.“Why should I pay someone to do what I can do better?” I thought. But the truth was - I couldn’t grow unless I did.
We documented our workflows, set clear KPIs for every role, and created a chain of responsibility so that issues could be solved without climbing straight to my desk.
And the moment that happened, I saw the difference. Clients got faster responses. Projects moved smoother. I finally had the space to focus on growth instead of firefighting.
Stage 2 isn’t about “hustling harder.”It’s about breaking the habit of doing everything yourself. Until you do, you’re not scaling - you’re just running faster on the same treadmill.
Stage 3: $150K–$500K - When Your Business Becomes Bigger Than You
By the time you reach $150K in annual revenue, something shifts. You’re no longer a scrappy freelancer with a few helpers - you’re running a real business.
You’ve got processes, a small team, maybe even a sales rep or two. The client base is more stable. You’ve got recurring revenue streams. For the first time, you might feel like you can take your foot off the gas a little.
That’s where the danger creeps in.
The Illusion of Control
I vividly remember when we crossed this threshold in my agency.I thought, “Finally, I can breathe.”
But breathing doesn’t mean coasting. This is the stage where complacency can quietly kill your growth.
You think:
“The team’s got this - I don’t need to check in as much.”
“We’re profitable - no need to push for change.”
“The systems are working - why mess with them?”
The problem? What got you here won’t get you there.
While I was enjoying the “comfort” of Stage 3, cracks started to show: Projects began slipping because our processes weren’t designed for a bigger workload. Clients expected more complex solutions than we were used to delivering. Team members started asking questions about growth, raises, and career paths - things I hadn’t prepared for.
The Founder’s Dilemma
Stage 3 is a balancing act between two extremes:
Getting pulled back into operations because “it’s faster if I just do it myself.”
Pulling too far away and losing touch with the reality of the business.
I fell into both traps - sometimes in the same week. One day I’d be on a sales call for a $50K project, the next day I’d be fixing a broken plugin at 2 a.m.It was exhausting and confusing.
The Growth Breakthrough
The turning point was when I stopped thinking of myself as “the boss” and started thinking like a strategic investor. Here’s what changed:
I built a leadership layer. Instead of me managing developers directly, I put team leads in place who owned delivery.
I stopped approving every decision. If a project lead needed a $200 tool to solve a problem, they bought it - no need to wait for my green light.
I doubled down on brand and partnerships. While the team handled operations, I focused on building relationships that brought us high-ticket deals.
It wasn’t easy letting go. The truth is, founders are often the least qualified people to manage day-to-day operations at this stage - we’re too impatient, too emotional, and too focused on the big picture to do it well.
But once I stepped out of the weeds, something incredible happened: Revenue didn’t just grow - it multiplied. The team took ownership, clients felt more secure, and I had the mental space to think 6–12 months ahead instead of just surviving the week.
Stage 3 is where you decide whether you want to be the operator of a small business - or the owner of a growing asset. One choice keeps you busy forever. The other gives you freedom.
Stage 4: $500K+ - The Plateau Problem and the Power Moves
By the time a studio or agency reaches the half-million mark, things look very different from the early days.
The founder isn’t hustling for every project. The brand has weight in the market. There’s a real team, layers of management, maybe even a few internal products in development.
From the outside, it looks like “you’ve made it.”
But here’s the part no one warns you about - this stage comes with its own set of traps.
The Plateau Problem
I’ve worked alongside and consulted with multiple agencies in this bracket, and one theme is constant: growth slows down.
Not because the market isn’t there, but because the hunger changes.
The systems are in place. The clients are stable. The profit margins are decent.
And then… comfort creeps in.
Comfort is dangerous.
It’s the silent killer of momentum.
Some founders start pulling more dividends instead of reinvesting. Others get distracted by side projects. And a few simply stop looking at their business through the lens of “what’s next?”
The Strategic Fork in the Road
At this level, the agency is like a high-performance sports car - it can cruise comfortably at 120 km/h forever, or it can be tuned to hit the next gear.
The choice boils down to two paths:
Scale further - reinvest aggressively, expand into new markets, launch new service lines, and strengthen leadership.
Optimize for profit - keep the size stable, refine operations, and pull consistent dividends without chasing risky growth.
Neither path is wrong. The danger is in not choosing - drifting in a grey zone where the business stagnates.
The Moves That Keep You Growing
In the agencies I’ve seen break through this ceiling, a few common strategies stand out:
New Revenue Streams - launching niche products, SaaS tools, or training programs that complement the core services.
Acquisitions & Partnerships - bringing in smaller teams to expand capacity or capabilities without starting from scratch.
Geo Expansion - moving into higher-ticket markets while keeping the home base strong.
Leadership Evolution - replacing “good” managers with great ones who think like owners, not employees.
The founder’s role at this point is almost entirely strategic.
Your job isn’t to push buttons - it’s to make the decisions that will still matter 18–24 months from now.
The Reality Check
I’ve seen agencies that double after hitting $500K, and I’ve seen agencies stall for five years straight at the same revenue.
The difference almost always comes down to mindset:
Do you see the business as a vehicle for freedom that should work without you?
Or do you still secretly enjoy being “needed” in the day-to-day because it makes you feel in control?
Stage 4 isn’t just about money - it’s about vision.
And if you’re not deliberate about that vision, the market will make the choice for you.
Why Go Pro - Turn Your Agency Growth into a Predictable System
If you’ve read this far, chances are you’ve seen yourself in at least one of these stages.
Maybe you’re still stuck in endless client work.
Maybe you’re firefighting daily instead of building systems.
Or maybe your revenue is growing, but you feel like you’re running faster just to stay in place.
Here’s the thing:
Most agency owners stay trapped in these cycles for years because they try to figure it out alone.
They keep working harder instead of smarter - and their growth stalls.
That’s exactly what the Pro plan is designed to change.
❌ The Problems You’re Facing Now
You’re the bottleneck - everything depends on you, and stepping away slows the business down
Unpredictable revenue - one bad month wipes out the last three good ones
Hiring or ads don’t fix it - without the right systems, it’s just more chaos
Competitors are moving faster - but you can’t figure out why
✅ What You’ll Get as a Pro Subscriber
Deep-dive strategy breakdowns from my own companies - exactly how we’re hiring, scaling, selling, and reinvesting
Market updates and trends - so you know where the opportunities are before everyone else
Pro-level templates and docs - sales funnels, hiring processes, and financial tracking you can use instantly
Private founders-only chat - share deals, ask questions, connect with other like-minded entrepreneurs
Real-time insights - what I’m buying, building, or pivoting - and why
🚀 Why This Matters
This isn’t theory - it’s field-tested systems from real businesses I own and operate.
These are the same frameworks that took me from struggling founder to co-owning multiple six-figure agencies.
If you want to stop guessing, skip years of trial and error, and build an agency that grows without burning you out - Pro is your shortcut.
📌 Upgrade to Pro today and start building an agency that runs like a machine.