I almost never schedule two DJ jobs on the same day.
It can be tempting to do, especially during those high-demand dates like Saturdays in May or June.
But I like to give each wedding client my undivided attention on their wedding day. And I don't like to expose any wedding client to the risk that, for example, I'd be running late getting from one job to the other. It's just not worth the risk -- to me or to you.
But there is one circumstance in which a DJ doubleheader could make sense, and be a win-win situation. That'd be when the same DJ is hired to perform at a day-time and night-time reception AT THE SAME LOCATION. For example, a hotel might book a noon-to-4 pm reception followed by a 7 pm-11 pm reception in the same ballroom. In that case, the same DJ could easily handle both jobs. And could offer a price break to each of those clients, since he only has to set up once for both jobs.
Not only would the DJ be right on time and right in place for the second job, he'd have a chance to relax and take a much-needed break between the two events, ensuring that he's reenergized for the later job.
I've had this opportunity-- two jobs in the same venue on the same date -- just once in over a decade of DJ'ing, and I wonder why it doesn't happen more often.
A thought: if your reception venue is a double-booking venue, ask the site coordinator if you can contact the couple holding the earlier or later event on your date. Then, ask them who they've booked for their DJ or band and see if that entertainer might be a good fit for your needs. Chances are, he'll be willing to give you a price break.
Similarly, if you're the first one to book at a two-event-a-day space, ask your site coordinator to pass along YOUR name to the other couple utilizing that space that day, suggesting they contact you to find out about your DJ or band. In that case, if your entertainer is a good fit for them as well as for you, you could share the price break with the second couple.
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