Conquering 3 Big Challenges in Order to Grow Your Digital Agency

By Jason Swenk on August 9, 2023

Are you an accidental agency owner? Most of us are! That is why it’s important to continually evolve in order to grow your digital agency. Can you identify the milestones that have gotten you where you are? What are the biggest challenges you’ve had to face? As an agency owner, it’s important to stay inspired and stay the course on the path we’re paving for ourselves. Today’s guest took inspiration from various industry leaders to start his agency and learn how to grow from just an owner to a CEO. He’s been in the agency world for over ten years and has had to reinvent a few times to keep up with new challenges. He shares ways he has conquered challenges in different stages of his agency and the milestones that helped him keep going.

Andrew Gottlieb is the founder and CEO of No Typical Moments, a digital marketing agency that works exclusively with purpose-driven social impact-focused businesses. His agency acts as a Fractional CMO working executing social media campaigns for online education. His agency handles everything from media buying to Instagram, Facebook, and Google campaigns, and backend email marketing solutions for some of the world’s thought leaders.

In this episode, we’ll discuss:

  • Evolving the agency’s service offering to keep up with market changes.
  • The importance of diversifying your lead gen source.
  • Overcoming 3 big challenges of growing an agency.


Apple | Spotify | iHeart Radio | Stitcher | Radio FM

Sponsors and Resources

E2M Solutions: Today’s episode of the Smart Agency Masterclass is sponsored by E2M Solutions, a web design, and development agency that has provided white-label services for the past 10 years to agencies all over the world. Check out and get 10% off for the first three months of service.

Podcast Takeover!!

Get to know your Smart Agency Guest Host: Dr. Jeremy Weisz is the co-founder of Rise25, an agency that helps companies launch and run podcasts profitably. He followed Jason’s podcast and eventually joined the mastermind and has been a guest on the podcast before. Today, he’s helping Jason bring something new to the Smart Agency podcast audience by interviewing a special guest and getting a new perspective to the show.


Becoming an Accidental Agency Owner with Inspiration and a Mastermind

In 2010, Andrew was a senior in college applying for jobs and getting rejected from all of them. He had majored in Managerial Economics and had done everything right. However, it didn’t work out as expected so he had to sit down and reflect on his next move.

Someone told him about David Siteman Garland’s podcast where he described a lifestyle working from the beach in Puerto Rico while making six figures. That’s when Andrew set out to get himself to that point and developed the idea for his agency, No Typical Moments.

It turned out that the formula for building his ideal business included things he greatly enjoyed: marketing and new technologies. It took him 18 months to really develop the concept of his agency. Meanwhile, he worked odd jobs, did a couple more internships, and finally found a full-time job with a minor league baseball team.

In his agency journey, Andrew found many role models like David, Gary Vaynerchuck, Jesse Itzler, and more. They were an inspiration throughout building and growing his agency in different ways. Additionally, they helped him see the importance of taking advice from someone who already walked that same path.  He also credits involvement in a mastermind is a fundamental part of going from agency owner to Agency CEO.

What Milestones Propel Agency Growth?

Andrew officially started his agency in 2012 with six months’ worth of savings and the plan to either duplicate his income in those six months or find another job. After 90 days of endless meetings, he hit his first big milestone: finding a paying client.

From there, his growth was marked by milestones like meeting the agency’s first big client and making some key hires. Around 2013, Andrew met a sales expert who joined the agency and ended up being an important part of its growth. Having someone besides him to help with client work and sales made a big difference.

As he started delegating the client work, they were also able to take on more clients. Shortly after that, their next big client was the Pittsburg Marathon, which was another big moment for the agency.

Evolving the Agency’s Service Offering with Market Changes

Originally, the agency offered organic social media marketing, which included Twitter and LinkedIn. However, over the years he’s had to adapt to keep the business going. With time, Andrew realized there wasn’t a clear ROI he could break down for clients. There wasn’t a clear way to explain what those campaigns would do for their business. This was back when social media wasn’t what it is today. He realized doing paid ads lend to a more straightforward conversation. ROI is clearer with ads and it’s a cleaner business case to sell to clients. This is what inspired a change in their service offering.

Later on, their offer evolved again to Facebook ads campaigns, which actually became pretty much their only service offer. Everyone was using Facebook and it worked for the agency. However, the big wake-up call came when iOS 14 changed everything. As most know, this made Facebook advertising very challenging and clients started to pull out. Those who weren’t immediately taken aback saw their ROI go down pretty quickly.

Luckily, Andrew and his team had already been thinking about broadening their offering. They had their eyes on doing YouTube, LinkedIn, and Google advertising. Moreover, he realized some clients were more in need of thought leadership and strategic direction than advertising. Hence, they searched for a Fractional CMO who could point these clients in the right direction so the ad campaigns would have a better chance of success.

The Importance of Diversifying Your Lead Gen Source

Usually, clients defer to Andrew’s agency to get clear on their next best step in digital marketing. At some point, the easy answer was Facebook Ads. With it, you could generate revenue at the snap of your fingers. The game has changed, however. It’s now very important to be clear on where the business is at in its maturity to develop the right strategy. When a client brings on their team, they’ll help them with anything from email marketing, landing pages, copywriting, media buying on any major platform, or tech integration. They can also help manage employees, manage vendor relationships, contractors, and whatever clients require from a CMO.

When his agency changed course to a more full-service offering, he needed to get clients to understand it was a good moment to diversify their lead gen sources. If their entire campaign hinges on Facebook, they will have issues in the future. The storm from iOS 14 combined with other difficult moments for the platform finally helped some clients see the light. Some companies spent millions on Facebook ads only to have their ads accounts banned out of nowhere. Now they had a need to spend on Google and YouTube to get to a million in spending.

For the longest time, it seemed like Facebook could not fail. But, in that moment it became much easier to explain the importance of diversifying.

3 Biggest Challenges at Different Stages of the Agency Journey

For Andrew, the challenges presented by building a digital agency have changed depending on the stage of the agency’s growth.

  1. The mental challenge of entrepreneurship.
    As a 22-year-old starting a business, his friends went the more traditional route and had high-paying jobs. Their path offered a clear trajectory, whereas he entered entrepreneurship with much less clarity. The shame and embarrassment of not having a conventional career path affected Andrew’s confidence. It also affected his social life, since he had to pour all his resources into the business. He couldn’t afford to go out and risk spending money he would need for the agency.
  2. Growing the agency beyond the owner.
    Finding the right people to continue to grow the agency has been more challenging than he expected. He was lucky with his two first hires, who are actually still with him years later. However, he made a series of bad hires as the agency grew. He was not clear on the expectation for each role and needed to hand over control. Those first mistakes ruined some relationships for him.
  3. Staying inspired to grow.
    More recently, Andrew’s big challenge after 10 years is continuing to be inspired to grow. After years of weathering different storms like the pandemic and changes to his offering, it is time to reinvent again.

Do You Want to Transform Your Agency from a Liability to an Asset?

If you want to be around amazing agency owners that can see what you may not be able to see and help you grow your agency, go to Agency Mastery 360.  Our agency growth program helps you take a 360-degree view of your agency and gain mastery of the 3 pillar systems (attract, convert, scale) so you can create predictability, wealth, and freedom.

Would You Like To Get Access To A Proven Agency Framework For Growing Your Agency?