What I’ve learned running my own agency for 20 years

Some things have changed dramatically. I imagine if I told my 2004 self – who came to meetings with a Palm Pilot and projector – about marketing automation software, it would sound like science fiction. But in other ways, the core of the job remains the same – great campaigns start by correctly diagnosing a problem, finding the nugget that serves as the lynchpin of the brand and devising smart creative strategies and executions.

In my reflections on the last two decades and the changes they’ve carried, these are the lessons that I think have been the most powerful.

True leadership

A lot is said about having the right CEO for the right phase of a business, often reflected in large corporations hiring and firing CEOs accordingly. But for small, privately-owned businesses, the CEO must personally evolve to meet changing business needs.

In my early CEO years, leadership was a trial and error experience where I was leading by example, doing the work alongside the team. But as the business and I matured, I started taking leadership more seriously. The business couldn’t thrive if I was so focused on the day-to-day that there was no long-term vision. Consequently, I joined an executive coaching network and implemented a new management system.

What I learned from that transition is that true leadership is helping make other people better, not shouldering excessive work or participating in every project. Going from a doer to a leader is hard. When you’ve historically provided value by doing, shifting your mindset to playing a supporting role requires a lot of rewiring.

As a result, the later years of the business were focused on building structures, processes, and protocols – things that often feel scary or even threatening to creatives! Establishing this infrastructure, however, allows me to truly lead – delegating and empowering others with confidence.

Great storytellers

You can’t stay competitive in marketing without keeping up with nascent tech, but when it comes to hiring, there are higher priorities. Lest we forget, Flash and Quark were once non-negotiables. The one thing that doesn’t change in hiring great people is soft skills.

Over the years, I’ve asked all interviewees the same question: On a quirky scale from 1-10, where would you place yourself and why? I’ve never seen anyone grade themselves below 5, which I guess comes with the territory. It’s fun hearing the justifications for where they place themselves, but more importantly, they get to showcase their storytelling talents. In the modern world, this is invaluable.

I spend my life thinking about the things that happen to me and reverse engineering them to think about how I’ll retell those things to others to make the best story possible. Isn’t that just advertising in a nutshell? By seeking similar quirkiness and storytelling abilities, I’ve found talented people who are able to make unexpected and illuminating connections when it comes to communicating a brand.

New business

There is a certain amount of dissonance that exists in running a small B2B agency where you’re often selling clients on the power of million-dollar media budgets that you know you can’t afford yourself.

When I first started in this industry, the greatest competition came from other agencies – in-house teams weren’t considered as playing on the same field. Today, in-house teams have largely put this belief to bed. Competition is fierce, coming from all sides, and making it as a small agency requires tremendous grit.

We’re never going to have the budgets of the big guys, but we do have a reputation to uphold. Deciding what kind of brand we were going to be, living that brand, and entering every meeting with the satisfaction that we couldn’t have done any better is why we’re still here 20 years later. Our best source of new business has always been referrals and repeat clients.

So, though we do what we can to drive brand awareness on social media and network our tails off, we’re also keenly aware that we’re only as strong as our last pitch. Having the tenacity to continuously do good work has been the good luck charm that’s kept us afloat.

Two decades in, I’ve learned that success isn’t just about keeping up with change – it’s about staying grounded in what matters: empowering others, crafting great stories and showing up with excellence every day.