Thanks for asking!
This is a funny topic for me, I've always been a super music fan, but never played any instrument.
I've been more a "roadie" than just a merchandiser, I mean that I was with them all the time, loading, unloading, driving and helping out.
Sometimes I've also acted as tour manager, but only in venues we already knew.
Most of the largest shows have been with an Italian band throughout Italy, production was in the medium range, going between a few hundreds to thousands of people (less than 5 thousands).
Many of the smaller ones were in Europe, with american bands, where it usually was in the hundreds in undeground clubs - there 's a large variety of them in Europe, you can find the youth center in Switzerland that has hotel's level accomodations and the squat in east Germany where you sleep on the floor in the cold.
But it's a good network to get a lot of shows close to each other, so you don't have to drive much and everyone is kind.
We've also been playing to many festivals: from desert fest to duna jam, from freak valley to roadburn, from up in smoke to hellfest. It's another great way to make connections and meet the bands.
I'm especially fond of what's called stoner rock (I prefer the name desert rock though) and I've toured a lot with bands from the Rome based Heavy Psych Sounds label.
I've been doing it for about 5 years, then the main band I was following took a sabbatical and I went back into tech as a programmer (my day to day job since 1997)
It's been the best part of my life, and, as crazy it might sound, the time of my life when I saved the most: I didn't have to pay for food, drinks, traveling or going to concerts, which basically is where most of my finances went anyway...
I had to pay the mortgage on my house, but if I was renting, I could have saved on that as well.
Best and worst memory is opening to Eagles of Death Metal in Milan, where I've spent the night smoking pot with Dave Catching, founder of Rancho de La Luna and one of my heroes.
I've also shared the merch booth with Nic, their merchandiser, that few days later was tragically killed in the
Bataclan massacre.
TL;DR: I got to do it as a job just by answering "yes" to "we need a driver for this one date, are you interested?". I've been reliable so they kept calling me and I ended up being part of the crew, without even noticing.