Act Like You’ve Been There Before

On Concert T-shirts and Boardrooms

In my previous life, I used to sell bootleg concert T-shirts. You know the guys that are running through parking lots before and after the show selling $10 T-shirts? That was me. It’s how I made it through grad school. During that period, I learned some valuable lessons about marketing, selling, managing your product and about how people act when being sold to. Here are some of those lessons.

Lesson #1 It’s always about relationships

Depending on the situation you can either be the loudest and most abrasive to get as many people’s attention as possible, or you can try the subtle approach and try to create immediate one to one relationships with your product and the customer. Editors note: Because these were bootleg concert T-shirts, technically it was not always “legal” to sell them, thus calling attention to oneself was not always the smart way to sell. By allowing your customer to quickly peruse, touch and create that connection not only with the product/shirt but also with the you and who you were and the value you offered, you had a better chance at the sale. If they decided to think about it or were on the fence, you could always hang out with them, have a beer and create a lasting impression. If they still couldn’t make up their mind, you remembered who they were, what parking lot they were in, where their car was, and you came back later to get the sale…if you still had shirts left over. The sales funnel was indeed in action and the relationship created. In this case, speed, i.e. the number of people you could touch and see and the number of sales that you could get, was always a primary factor to success, along with cost of course; and given that there is only so much time before and after a show to get the sale, creating that relationship quickly was important.

Lesson #2 Fish Where the Fish Are

I know it sounds trite but you can’t sell to people who aren’t “there.” Sometimes we would try and sell somewhere else other than the parking lots. For example we would try and sell shirts where we “thought” people would have to stop for food, gas or otherwise, like a rest area. The thinking being that we would be the only ones there selling. If there was no competition, the better the chance to get the sale; and trust me, there was and is a lot of competition both in the T-shirt world and the business world. So if you can find that pocket of fish, well, bingo! But for us, the results were mixed.

Better to leverage your product and price where there are thousands of people and not hundreds. If you only have a limited amount of time, don’t screw around hoping that your customer will show up. Go where they are. Another important aspect of this lesson is indeed knowing the lay of the land of where your fish are. It’s worth it to find that spot where the competition is not. It’s there. The parking lots in arenas and stadiums, last time I checked, are big and so is the offline and online worlds.

Lesson #3 Always be Aware of Threats

Now because we’re technically selling T-shirts that were not the authentic “inside” shirt, this doesn’t mean that demand outside was any less than what was inside. We sold a shirt that was sometimes 2 to three timess less than what they cost inside. Because of that, there was plenty of demand but also plenty of competition too; and there were plenty of stadium employees and law enforcement people that did not want you to be selling those shirts. I understood that and they did too. In fact, without us out there selling, alot of them would not have had the job of trying to prevent us. In a sense, it was a win-win. They understood that, so when we were caught, they would take your shirts and nothing more and then send you on your way. Now that’s all nice and all but a couple of things to understand. The shirts are not free, so if I come back empty handed, I better have sold them and not have had them taken. I wasn’t in the business of losing money and neither should you in any situation. Know who is out there. Know who the competition is. Know what they look like. Know who is a threat to your business.

Your ability to recognize threats ahead of time will save you time, effort and money if you know how to identify them, how to avoid them, how to go around them and how to sell where they ain’t. the same holds true across the board in business. Avoid the obvious mine fields. The threats, they come in all shapes and sizes too. We had to avoid stadium employees, undercover officers, uniformed employees and officers as well as other people selling other things. All there to intefere with the sale. I rememeber one time in Philly walking up to a car as they were parking, to sell a shirt, and out pops 2 other shirt sellers, a guy selling weed, another selling coke and another selling posters and another selling programs. Try competing with that!

Now, you can kind of see why we always thought trying to sell at a rest area was not necessarily a bad idea!

Lesson #4 Act Like You’ve Been There Before

It’s pretty obvious that the more you stand out, the less you can blend in. Oftentimes, we wanted to be just like every other concertgoer except we were carrying a large amount of concert shirts and we were trying to sell them quickly. If you’re scared it shows. if you’re nervous, it shows. In business, the same holds true. There will be times when you are chasing a big deal, it might even be your first big deal-the client doesn’t need to know that. All they need to know is that you have things under control and it ain’t your first rodeo. People, clients, prospective buyers, they all can sense when something isn’t right. Be cool and play it cool. Need help? Ask for it, just not in front of the client. All the client wants to know is that you’ve got your shit together.

In the sports world, have you ever noticed really veteran teams that win a semi-big or important game? For the most part they are excited but they’re not mobbing each other and they’re not going crazy. Why? Because they know it was an important win, but not THE win, not a championship. They know more work needs to be done. Enjoy it a little and keep moving on. Act like you’ve been there before.

I can remember taking one of my friends on one of our road trips. It was the second Lollapalooza tour and he was in a state of excitement and amazement. I was too but knew I was also there to work. There was some big names. Pearl Jam, The Chili Peppers, Soundgarden and Lush just to name a few. It was huge. He was there with me to sell shirts but he got caught up in partying, the paranoia of undercover cops, and the cool cities we went to, and just the whole concert scene and was completely incapable of acting like he’d done it before and focusing on the task at hand. Needless to say, he made no money but… he had a blast. I on the other hand, made money and… had a blast. The postscript is that we both still look back on those times with some tremendous stories either way.


I think back on my T-shirt days with fond memories. The characters and the concerts forever etched in my head. What I find amazing is how many of those experiences continue to play out in business and life lessons. I’ll keep sharing the interesting ones.