When Erik Olson started his first agency, he had no clients, no team, and no experience in marketing. Just a laptop, a phone, and a dining room table. Fast forward to today—he owns three niche digital agencies, generates over $6 million in annual revenue, and leads a team of 49 people.
Sounds impressive, right? But it wasn’t always smooth sailing.
Starting From Scratch
Erik didn’t come from a creative or marketing background. He was a software developer with an MBA who saw a gap in the market and jumped in. Like many new agency owners, he made plenty of mistakes in the beginning: saying yes to the wrong clients, charging too little, hiring too quickly (or too slowly), and not having clear systems in place.
The real turning point? Focusing on a specific niche and solving a clear problem.
“Once we knew who we served and what we solved, sales got easier, marketing made more sense, and recurring revenue became possible.”
Finding Clients in the Early Days
At first, Erik got freelance gigs through Elance (now Upwork) by bidding on jobs in the evenings after work. Within days, he landed his first few clients. When he left his job (he was actually fired), those freelance gigs were already bringing in half his old salary.
His next step? Tell everyone what he was doing. Old coworkers, bosses, friends, even family. He emailed them, posted on social media, and even sent letters. He didn’t hide the fact that he was going out on his own—he owned it.
“People are scared to say they’ve started something in case it fails. But I’d rather risk the embarrassment than not give it a real shot.”
From Generalist to Niche Agency Owner
Like many founders, Erik started out as a generalist—taking on any and every project. But things only really started growing when he chose a niche. With a narrow focus, you learn more about your ideal client, your messaging gets tighter, and you become a known expert in that space.
He didn’t jump into three agencies at once either. He built one solid agency first, then used the experience and systems from that to spin off into new niches.
If you’re thinking about choosing a niche, Erik says: start with one, build it up, then expand if it makes sense.
How He Hires
Hiring has been a big part of Erik’s growth, and he approaches it differently than most. While many agencies rely heavily on contractors, he has chosen to build a team of mostly full-time employees. Why?
Control and accountability.
Long-term investment in people.
Stronger client relationships.
“Most agencies are just sales machines that outsource the work. We build real teams, and that’s part of our brand.”
Still, he admits hiring isn’t easy. Interviews are often misleading, and soft skills are hard to spot. His advice:
Ask detailed, technical questions.
Don’t ignore red flags.
Call real references (past supervisors, not just friends).
Trust your gut—if it’s not a clear “yes,” don’t hire.
Systems and AI
Running three agencies isn’t easy. Erik relies on solid systems to keep things organized. He also uses AI—especially for internal operations like documentation, planning, and streamlining workflows. But he’s careful not to rely too much on automation.
“One of the few things that still sets us apart from AI-driven agencies is being real people who can talk to other people. That’s not something you want to outsource.”
Sales as an Introvert
A lot of agency owners struggle with sales—especially if they’re introverts. Erik gets it. He’d rather be on a quiet farm than in a sales call. But building a business means stepping outside your comfort zone.
“You don’t have to love selling, but you do need to put yourself out there. No one’s hiring a ghost agency anymore.”
He suggests starting small—go to local networking events, build a few strong relationships, and focus on services that don’t require constant client hand-holding (like SEO over ads). And remember: practice makes perfect. Sales gets easier with time.
Dealing with Difficult Clients
Everyone deals with bad clients or scope creep at some point. Erik’s advice? Get better at saying “no,” set clear boundaries, and have solid contracts. And when a client becomes a real problem, don’t be afraid to walk away.
“It’s better to lose one bad client than burn out your whole team.”
If He Could Do It All Over Again...
Looking back, Erik would’ve done a few things differently:
Chosen a niche sooner.
Focused on building systems earlier.
Been more honest about the emotional side of running a business.
He also spent time improving himself—not just the business. That meant coaching, reading, therapy, tough conversations, and developing self-awareness. Because growing a business also means growing yourself.
Final Thoughts
If you’re just starting out or struggling to grow, Erik’s journey is proof that you can get there. But it takes time, focus, and a willingness to do the unglamorous work—sales, structure, and self-development.
“This business has tested me in every way. But it’s also been the most rewarding thing I’ve ever done.”
Whether you’re freelancing from your kitchen table or trying to scale past $1M, there’s something to learn from someone who’s been through it all—and built not just one, but three successful agencies.
Ask him anything. He’s still in the trenches too.
