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Marathoner,

I don't have any experience selling at expos, but I have done some large events. I've got some info and I hope some of it can help you!:
I have done some selling at high school sports tournaments. In the city that I live in, they have an event every spring for all of the spring sports championships(basketball, track & field, soccer, tennis, you get the idea!). There are about 15,000 high school kids, parents, and family that converge on this small college town over a couple of weeks(they spread the events out). Anyway, I have shirts screen-printed for this event and I set up at different places of the college campus during the 2 weeks (authorized vendor). They call the whole event "Spring Fling". I have shirts made up for that are Spring Fling related. Some just say Spring Fling and the year of the event. Some of them are sport specific. Track & Field I break down into specific events. I make up cool little sports graphics for all of the shirts, but mainly just one or two colors. I buy the least expensive shirts I can find, and at wholesale prices. I charge a flat $10 for ease of transaction.
The tricky part, especially sense I'm getting them screen printed in advance, is how many shirts to have. Like I said, there are about 15,000 people that are there for the Spring Fling, and most would like something to remember their achievements by(parents and athletes), so my numbers may be different than for an expo. It was trial and error the first couple of years, but now I pretty much know what to expect. I now have 1,000 shirts made for the whole event. Last year I sold 920 at $10/shirt and the last day I had a buy one get one free sale to get rid of the rest.

So around 15,000, and I sold around 1,000 shirts, and I wasn't the only one selling. Again the demographic is different than at an expo. If you are going to an expo, I presume it would cover a couple of days, and you would probably need attendance figures from the organizers in order to see how many blanks you need, how much transfer paper, ink, and that kind of thing. Also your method of wanting to heat press them is a good setup. You could have some already made up and ready to sell, then when you start to run low, make up some more. I would suggest a good denomination ($10 works well!) for ease of transactions. People are in a hurry.
As far as the styles you talk about. Come up with as many as you can beforehand. Have them already heat pressed and have them on hand as examples of what you can do. See what sells. Then just heat press more of what sells. You say you want them to be personalized and on demand. How? With just names of the customers, or they come up with a design or some text and you make the shirt while they wait. I find people tend to be in a hurry and I don't know how well that will work, but you can test it out.
As for numbers, that really depends on of course the size of convention, type of convention (obviously) and also the demographic of the attendees. The demographic will at least let you guess as to whether they are the t-shirt buying type. For instance, you'd probably sell more shirts at a car show than at a convention for bathrooms! I have no idea about the health and fitness crowd, but at least you know what your target audience is and can do some research about it. You say that you are going to start smaller, so I would suggest you get blanks that are aroung 3-4% of the projected attendance figures. You more than likely won't sell that many to start with, but since they will be blanks you can always use them at another time, for another event. And if you have the money to buy a heat press, the cost of the shirts won't break the bank.

I hope I have been at least a little helpful. If you need some clarification of something I've said (I've found that I can be confusing at times!) or have any more questions at all, just let me know. :D
I'm sure there are others here who will jump in and help as well.;)
 

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It sounds like you already have a pretty good idea about everything. If all you have left to worry about is the shirts, I say you have nothing to worry about. You say your partner want to go conservative. Do you know the attendance figures yet? What does your partner consider conservative. I think 3-4% would be conservative for the number of shirts you need. Again, unused shirts aren't necessarily a bad thing, because you will use them at another time. Do you have an idea about where you going to get your shirts from. There are many places to get different styles, and the prices are very good for wholesale purchases.
Sometimes when you start something new and you're kind of unsure of where you're going, it's good to here someone on the outside say you are doing the right things, so here it goes: " You have a very good plan for starting out, and you are definitely headed in the right direction!"
 
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