The 5-Year Itch. (or: What I’ve learned after 5 years as an agency owner.)

Steve DiMeo : Partner, Co-Chief Creativity Officer

We started an ad agency in the middle of a global pandemic.

Five years later, we’re still here. Still growing. Looking forward more than backward. But it’s key to look back and see how we got here—you know, a lotta ins, a lotta outs, a lotta what-have-yous.

We went from working remotely—hiding out from the swirling Covid dervish—to having a small, shared office space in South Philly—where everyone hated the parking situation—to a cool office of our own in Media. But where we did what we do has been only a small part of our story.

I gained a lot through these years. From leadership to creativity to business ownership. For example, I still suck at numbers, but I learned a lot about budgets and such.

So, here are ten things I’ve learned over the past half-decade as one-third of a partnership in PINE.

1. Lead with what you know best, but don’t disregard the stuff that isn’t totally in your wheelhouse. In other words, Kate is our amazing CEO and strategic wunderkind, but that doesn’t mean all that stuff is in her lap and not in ours. We’ve got to be present and understand how to pitch in on all things, not just the creative stuff.

2. Clients want trust, maybe even more than talent. We do our best for our clients, from strategy to creative and beyond. But first and foremost, we need to gain their trust. We need to prove to them that we know what we’re doing, and that we’re damn good at it.

3. Before you can trust the process, you’ve got to create a process. Here’s one of those things that most creative types will shrug at. “Give me the brief and a deadline. That’s all I need.” Ha, I say, ha ha! It takes all the leaders to develop a smart, workable process that will ensure work gets done right and on time, without the nasty little sidetracks.

4. You’ve got to work ON the business, not just FOR the business. The job doesn’t end with a nice ad concept for a client. We are our own clients. We need tending, maintaining, and to make nice-nice with the business of running a business.

5. Nothing is beneath me. Take out the trash? Sure. Load the dishwasher? Okay. What’s that smell? I’ll spray air freshener. Need more milk for the Froot Loops? I’m at Trader Joe’s now. Write this simple email? Not a problem.

6. Wake up every day with a passion to do something better. Just because you think everything is running smoothly, there’s always the opportunity to do it even better.

7. Think positive. We’ve embraced Positive BrandingTM as our promise and our guiding principle. That means we’re all about doing good things for our clients, for their customers, and for ourselves. As I enter my curmudgeon years, I take this to heart and must always remember that being an optimist is just as easy as being a pessimist, but it feels a lot nicer on the inside.

8. Be thankful for what I’ve been through but be open to what’s happening now. I’ve been in the business for a long time, and I’m glad that I’ve had the experiences that made me the creative leader I am today. But I can’t rest on those laurels. New sh*t has come to light, and I’ve got to keep feeding the monkey.

9. Let it go. Sometimes I just have rely on others to get things done, and I don’t have to hover like a dance mom on recital night.

10. Growth isn’t possible without trust. I have trust in my partners and the people we have on board with us. I know they trust me, or at least I hope so. (We haven’t done the trust fall thing, but I think I’m too attached to ravioli for anyone to catch me.) This is how we grow. This is how we thrive. This is how we will keep PINE alive and strong.

Bonus: Snacks help. Always keep delicious stuff in the office to snack on. Hungry people make terrible decisions.

I’m excited for what the next five years will bring, and how this place will be accepted into the ad community. But mostly, I’m excited to help our clients grow and for finding new and unique ways of making that happen.

And snacks. I’m excited about snacks.