The first fifteen.

by Rich Sullivan, Red Square / RSQ

As of May 1, 2015, I have been at our agency for fifteen years. That’s 5,478 days, including weekends. During my time at Red Square, the advertising business has changed a lot — but the more I think about it, the more I realize the core business hasn’t changed as much as we all like to think.

An auspicious start to my advertising career.

My father, who started our company, always told me, “This isn’t a business that can be taught.” I understand now that he wasn’t talking about art and copy (and certainly not code). He was talking about the actual business of the business, and he was right.

Here are the top 15 things I’ve learned by doing this stuff for fifteen years:

1. If you don’t love this business, find something else to do.

Advertising is grueling. The hours can be odd. The highs are high, and the lows are low. So if you aren’t motivated by a love of the craft of making advertising, you are not going to last long. No big deal. Go find something you love.

2. This is not a job, it’s a craft.

It took me a few years to learn this. As I studied and dissected what was universally considered “better” advertising (the One Show-worthy stuff), I started noticing that attention to detail and finesse is what separates merely good ads from great ones. That’s craftsmanship.

3. Practice, practice, practice.

I don’t really believe in talent. I won’t argue predisposition, but in order to become proficient in anything, you must work incessantly to improve.

4. Clients get the work they deserve.

I’ve been lucky to have had wonderful clients over the years. Great work is always the result of an excited agency team and a thoughtful, engaged client. Clients who are clear in their goals, can articulate cogent feedback and have fun in the process are the best. And their work always reflects it.

5. Don’t do anything for money.

Every bad decision I’ve made thus far in business occurs when the decision is solely motivated by money. You have to be driven by something else.

6. Tell people what you are doing.

When I started running the agency, we had about 20 people. We grew pretty quickly to 80-plus. That was tough. What I’ve had to learn is how to consciously communicate. It’s very easy to run something small. You are in contact with pretty much everyone in the operation, in close proximity, all day long. Once an organization grows, everything becomes a “game of telephone.” So I find it absolutely imperative that I gather the agency frequently to tell everyone what we’re doing and what I’m thinking.

7. Presentation matters.

I get horrible stage fright. But over the years, I’ve learned that my nerves stem from lack of preparation. I consider the ability to present the number-one, most important skill in advertising. If one cannot articulate a position, then one cannot advance it. I’ve seen so many great ideas killed because of poor presentation. Proper packaging and presentation of any idea is crucial.

8. Don’t get into lawsuits.

Lawsuits are soul suckers. I’ve never been in full-fledged litigation, but I came close once. It was expensive and distracting. Be simple in your agreements and contracts, and if a dispute occurs, remember: the only people that will win any sort of legal proceeding are the lawyers.

9. Advertising is not a democracy.

This one is really about committees. There is a reason there are no statues devoted to committees. It’s because great things, new things, bold things, are never the result of consensus. These things are the result of an individual sticking his or her neck out.

10. Beware of RFPs.

To make blanket statements like “we don’t do RFPs” is foolish. It’s a part of our business. The trick is to get good at vetting which ones are worthy of pursuit and which ones should be cast off quickly. I am still learning this. Painfully at times. I’ll report back after another 15 years.

11. Advertising has always been in love with technology.

Recently, I’ve read a lot of articles bemoaning how our industry is overly enamored of technology. And while I agree that advertising is fundamentally about people and ideas, I think advertising has always been about technology. If you think back to the beginnings of radio and television, there are a lot of parallels with the change our industry is experiencing today.

12. Advertising is improvisational.

Markets shift, change happens on the agency side and on the client side, economies falter, bubbles happen. And a thousand other things. It’s important to have a plan for your client and agency, but you’ll need to be comfortable with things changing frequently. Because they always do.

13. Advertising is a service business.

There exists a lot of mythology about how some agencies and creative superstars operate on a “it’s our way or the highway” basis. This is nonsense. Let’s assume that your clients are smart and have great products or brands. You need to listen to them. Because, at best, you are operating with limited knowledge of the intricacies of their operations. You should guide your clients and be direct and honest in your counsel, but like Matthew McConaughey says, “You’ve just gotta find that balance.” The ad business is a service business.

14. Be nice to people.

No one puts up with jerks for too long. This goes for the agency, clients, vendors, everyone. People work with people they like. If you’re pleasant, you’ve got a better shot at being liked. Easy as that.

15. If you make great work, everything else will take care of itself.

The work you do is the most important thing there is. Throw everything you have into it. Obsess over it. All else is secondary. If your work is great and shows results for your clients, then things turn out just fine.

There you have it. My career thus far distilled into a neat little listicle. Until next time. Email me if you want to discuss: or you can silently stalk us at