I got a dump trailer and now I can’t keep up with the requests, and I’m not organized at all

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First of all, stop doing jobs at random. Decide on set days of the week and hours that you will work on this. Most customers will have no problem waiting a couple of days for a reliable pickup. Second, limit the number of places you can be contacted. One text or messaging point of contact and one phone number is plenty. If a customer contacts you through another channel, you can just copy and paste a standard message advising them you only take requests through specific platforms. Third, immediately put all scheduled pickups into a calendar app and set reminder notifications if needed so you won't forget. If you want to get fancy, you can even have customers book their pickups online and have those bookings go directly into your calendar. Just because it's a side hustle doesn't mean it can be disorganized. You'll spend a lot less time and be a lot more reliable for your customers if you just standardize a few simple things.

I considered dump trailers. 2 things: 1. Make sure you're charging enough to cover for overages or fees for stuff that shouldn't be in the trailer. Don't expect your customers to ever cough up the extra money after the fact. 2. If you do this as a drop off/pickup service, make sure you have 2 GPS tracker son the trailer (one obvious , one well hidden). Make sure you lock it up VERY well. Trailers of any kind are easy to steal, and theyr stolen often.

The calls are where you are bleeding the most and probably do not even realize it. When you are on a job site dumping a load, you physically cannot pick up the phone. That person calling you right now is already dialing the next hauler on Google by the time you see the missed call. Two things that fix this without adding overhead: 1. Auto text-back on missed calls. Most business phone apps handle this - OpenPhone, Google Voice, even some carrier features. Someone calls, you can not answer, they get an instant text: "Hey, on a job right now. What do you need hauled and what is your zip?" Now they are in a conversation with you instead of moving on to your competitor. 2. Stop quoting live over the phone. Send everyone a standard message: "Shoot me a photo of what needs hauled and your address, I will get you a price within the hour." Batch your quoting into 15 minutes at the end of each work block instead of getting pulled out of work constantly. The operators I have watched go from one trailer to three did not get there by working harder. They got there by making sure every lead that came in actually converted to a booked job. Right now you are probably losing 40-50% of people who reach out - not because they said no to your price, but because they called someone who picked up.

Good advise here. Consider leveraging Jobber ($39/monthly). Book and schedule jobs, send quotes, invoices, get paid, get a web presence for your Google Business Profile. Sanity for $39.