How I Grew My Agency to $20M: Lessons Learned the Hard Way
When I started Hennessey Digital, I hoped to build a successful agency, but I never thought it would grow into a $20 million business.
Looking back, it has been quite a journey. There were mistakes along the way—some of them costly ones—but each taught me something important about how to grow digital marketing agency.
I know that growing an agency comes with its challenges. I’ve felt the struggles of long hours, tough decisions, and figuring out how to scale the right way.
Now, I want to share what I’ve learned over the years to help other agencies who are on the same path. My hope is that you can avoid the costly mistakes I made and grow faster with fewer bumps in the road.
Here are the lessons that made the biggest difference for me as I scaled my agency.
1. Delegate and Focus on Your Zone of Genius
When I started, I thought I had to do everything myself: payroll, account management, sales calls, even link-building strategies.
I didn’t know it then but I was becoming the bottleneck of my own business.
The problem? I was spending more time on tasks that I wasn’t great at instead of focusing on what I was good at.
I learned the hard way that your time is your most valuable resource. To fix this, I did an exercise where I tracked everything I did for two weeks. Then, I sorted tasks into four categories: incompetent, competent, excellent, and unique.
Anything I wasn’t excellent at or that wasn’t unique to me got delegated. For instance, payroll wasn’t my strong suit, so I hired a CFO. That freed me to focus on strategy and agency growth—the things I’m uniquely good at.
If you’re not sure what to delegate or how to do it, here’s a quick roadmap:
Be Ruthlessly Self-Aware
Take a hard look at how you actually spend your days. What tasks light you up? What do you dread? What takes you 3 hours that someone else could knock out in 30 minutes?
I used to think I had to be the one handling client strategy sessions, bookkeeping, and social media management. But trying to do it will kill your creativity and limit your growth.
So, pick tasks that you’re great at, and delegate the rest.
Delegate Like Your Business Depends On It (Because It Does)
The moment I started hiring people who were better than me at specific tasks was when we really took off. I found brilliant people who complemented my weaknesses—experts who could handle content marketing and finances better than I ever could.
A stronger digital agency isn’t built by one person trying to be the best at everything. It’s built by a team of specialists working in their zones of genius.
My video editor is great at coming up with creative video marketing ideas and edits. My CFO knows numbers inside and out. These aren’t roles I could—or should—try to master.
Let go of the ego that says you need to be the best at everything. When you focus on what you’re uniquely good at and let others do the same, you create an agency that’s greater than the sum of its parts.
2. Create Systems and Processes For Your Agency
When you’re trying to scale an agency, systems and processes are really important. Without them, growth is chaos.
The bigger your agency gets, the more moving parts you’ll have: new hires, client onboarding process, project deadlines. If you’re constantly figuring things out as you go, you’ll waste time, make mistakes, and frustrate your team.
Putting systems and processes in place isn’t something you should wait to do—it’s a step you need to take early if you’re serious about scaling.
Gianluca Ferruggia, General Manager of DesignRush, emphasizes the importance of starting sooner rather than later:
By putting these systems in place early, DesignRush avoided the chaos that can come with rapid growth.
So, don’t wait until the cracks start to show. The earlier you implement systems and processes, the more prepared you’ll be to handle growth while maintaining quality of your marketing services and efficiency.
Just like them, even in our early years at Hennessey Digital, we focused on documenting everything—starting with simple Google Docs and later moving to more sophisticated systems.
It wasn’t perfect, but it helped. When growth came, we were prepared, and those systems made scaling much smoother.
3. Establish a Clear Vision
As your agency grows, the number of people involved in decision-making increases. It can lead to misalignment if everyone isn’t on the same page.
A clear vision prevents this by ensuring everyone—from your leadership team to your newest hire—understands where the company is headed and how they can contribute to that journey.
So, take some time to chart out the vision for your agency’s future. Define where you want to be in the next few years—your goals, your values, and the kind of impact you want to make in your industry.
For example, my vision for the agency was to create a company that was a top choice for law firms looking for SEO expertise.
We wanted to be so attuned to the unique needs of legal marketing that law firms would see us not as vendors, but as essential extensions of their own growth strategy.
This clear vision helped guide every decision we made, from selecting prospective clients to hiring.
4. Hire For Attitude Over Experience
The team you build will ultimately define the success of your agency. As your business grows, hiring the right people is more important than simply filling roles.
I’ve found that hiring based on attitude and drive is far more valuable than just focusing on resumes or experience. Skills can be learned, but passion, problem-solving, and the right mindset are traits that can’t be easily taught.
Here’s what I focus on when hiring:
Initiative
Scaling means you can’t micromanage every project or decision. You need people who take ownership of their work and act without waiting for instructions. When someone takes the initiative, they not only keep the momentum going but often identify opportunities or solutions you might not have considered.
For instance, a team member who sees a better way to streamline a workflow and implements it independently adds immediate value, freeing up time and resources for other priorities.
Accountability
As your team grows, mistakes will happen—it’s part of the process. What’s important is having people who own their mistakes, learn from them, and improve.
Accountability creates a culture of trust and growth. When employees take responsibility for their actions, you can address problems constructively and move forward faster, rather than wasting energy on blame or excuses.
Problem-Solving
Growth comes with challenges, and having employees who bring solutions—not just problems—is a game-changer. Problem-solvers are proactive, resourceful, and critical to keeping projects on track.
Whether it’s resolving a client’s concern or figuring out how to meet a tight deadline, these team members help your agency thrive in high-pressure situations.
Alignment with Core Values
Your agency’s culture and values set the tone for how work gets done. As you grow, it’s easy to lose sight of those values if you hire people who don’t align with them.
Employees who share your core values maintain the culture and vision that built your agency’s success. They’re also more likely to stay engaged and committed, ensuring continuity as you scale.
These traits ensure that, as your agency grows, your team can handle increased demands without missing a beat. With the right people in place, it becomes easier to adapt to challenges and keep everything running smoothly as you scale.
5. Specialize and Stick to What You’re Good At
When it comes to scaling an agency, there’s wisdom in focusing on what you do best. Trying to be a master of all spreads you thin and dilutes your efforts. By narrowing your focus, you can hone your skills, build a solid reputation, and serve your clients better.
For us, the choice was clear: SEO for law firms. The legal world has its own set of rules and needs when it comes to online visibility, and we know it well. By diving deep into this niche, we sharpened our expertise, built trust with our clients, and delivered results that mattered to them.
If you’re looking to grow your agency, pick a niche you understand and stick with it. Specialized agencies work smarter, not harder. It sharpens your unique selling proposition and service offerings, builds your brand, and attracts the right kind of potential clients who will grow with you.
6. Focus on Creating a Positive Company Culture
A great team can make or break your agency, especially when you’re scaling. But simply having talent isn’t enough. To grow, you need a culture where your team feels valued, engaged, and motivated to stick around.
When your company culture is strong, it not only helps retain top talent but also ensures that everyone is aligned with your goals, working together to move the business forward.
What Positive Company Culture Looks Like:
- Empowerment: Give your team the freedom to take ownership of their work and make decisions. Empowered employees feel trusted, which boosts their confidence and commitment.
- Investment in Growth: Encourage continuous learning through training, mentorship, and opportunities to expand skill sets. When employees see that you’re invested in their growth, they’re more likely to stay.
- Recognition and Appreciation: Regularly acknowledge hard work and celebrate achievements, both big and small. Acknowledgement builds morale and reinforces the behaviors you want to see.
- Transparency and Honesty: Foster an environment where open communication is encouraged, and everyone feels comfortable sharing their ideas or concerns. Transparency builds trust and keeps the team aligned.
- Work-Life Balance: Show that you value your team’s well-being by supporting a healthy work-life balance. When employees feel their personal lives are respected, they’re more engaged and productive at work.
- Fun and Camaraderie: Create a work environment where people enjoy spending time together, whether through team-building activities or casual social events. A positive, fun culture helps foster strong relationships within the team.
By focusing on creating a positive company culture, you’re laying the foundation for a scalable agency that not only attracts great talent but also keeps your team happy and motivated.
7. Build Your Personal Brand
People want to work with individuals they know, like, and trust—not just faceless companies.
Clients are more likely to engage with a company if they feel connected to the person behind it. By showcasing your personality, values, and expertise, you establish yourself as someone who is approachable, reliable, and knowledgeable.
This kind of rapport is hard to build with a purely corporate-focused brand. I knew I needed to establish myself as a thought leader if I wanted to grow my agency and attract high-value clients. So, I started to focus on positioning myself as an expert in my field.
To build my personal brand, I started writing for industry publications and speaking at events. Sharing my expertise not only boosted my visibility but positioned me as a thought leader in my niche. I even wrote a book called Law Firm SEO, which helped me rank for a competitive keyword and solidified my reputation in the legal SEO space.
If you want to scale your agency, start building your personal brand today. Share your knowledge through blogs, videos, or books. Show the human side of your story—people want to connect with the person behind the brand, not just the business.
Your personal brand is a long-term investment that will help you attract clients, expand your network, and grow your agency.
8. Set Honest Expectations with Clients
As your agency grows, managing client expectations becomes more important than ever. The larger your client base, the more complex their needs become—and the more room there is for confusion.
Set clear expectations right from the start, and you’ll save yourself a lot of trouble. If you promise the world and don’t deliver, you risk losing clients and hurting your reputation.
But if you’re honest about what you do in a realistic timeframe, clients will respect you more. They’ll see you as a partner, not just a seller, and that trust lasts far longer than any quick sale.
I’ve learned that honesty is the best sales tactic. When clients know exactly what they’re getting into, they’ll be more patient and realistic. And the more you’re upfront with them, the more they’ll appreciate your integrity.
I’ll give you an example.
One client wanted to rank nationally for a tough legal term. I told them straight up it would take 18 months and cost $30K a month. They could have easily walked away, but instead, they respected my honesty and signed on with us.
9. Hire a Coach or Mentor
One of the best decisions I made was hiring a coach. My mentor helped me scale from $4M to $20M by giving me the tools and perspective I needed. He pushed me to write my book, join business networks, and think bigger than I ever had.
If you’re serious about growing your agency, find a coach who’s been where you want to go. It might feel like an expense, but it’s an investment that will pay off in spades. When they share their insights and learning with you, it accelerates your growth.
10. Be Generous to Grow Your Business
In business, the more you give, the more you get. It might sound counterintuitive, but generosity is one of the most powerful strategies for growth.
At my agency, we’ve given away over 300–500 copies of my book each month for free. Because generosity creates opportunities.
When lawyers read my book, they see the value we provide. They trust us with their SEO because we’ve already demonstrated our expertise and commitment to helping them succeed.
Victor Karpenko, the founder of SeoProfy, shares a similar approach.
The key here is to be generous with your knowledge.
Share it freely and frequently in the form of blog posts, webinars, ebooks, infographics, or some other format. The more value you provide at the beginning, the more likely people will trust you when they need your services.
Conclusion
When you’re growing your agency, don’t just focus on getting bigger. Make sure the growth is sustainable, or you’ll end up in a cycle of quick growth and setbacks.
Without the right systems, processes, and people in place, growing too fast can lead to burnout, missed chances, and a drop in quality.
Use the lessons I’ve shared to build sustainable growth that is built to last for years. Start small, but start now!
