holds and stuff

Had a former student (and colleague!) ask me about some of the in/outs of the business side of things, as he was transitioning from full-time to freelance. The basic questions were: what can I do to turn holds into jobs? Are recruiters worth the time? What about Employer of Record places vs. SCorp/LLC for billing and taxes?
Seemed like useful info to put out there generally, so here's (approximately) what I replied:
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re: holds . . .
There's probably not much you can do about this. There are loads of reasons shops hold you rather than book. Most of the time they're feeling out people's availability before the client commits to them, so nothing you do would get a booking from them before they're guaranteed work. Some shops are just dicks and really push for a first hold from everyone in town like their hair's on fire. Then they never get back in touch with anyone if the job falls through or they go a different direction. Talked to producers about that from certain shops and they're like "yup. Sorry about that. They made me do it" Sometimes you're the backup, sometimes you're the primary target. You just never know. So my strategy is to not stress it too much and just give holds (if they insist I'll tell them where they are on the ladder, 1st, 2nd etc). The first person to put the money on the table wins. I'll call and offer challenges as a courtesy, but I never try to cherry pick jobs anymore. Too volatile. Pay me and I'm yours:) what a whore. But I'm usually on at least one hold, most of the time on two, occasionally on 3 or 4. That can get a bit hectic, but again I don't stress it too much. Most of the time one comes through and I give the courtesy of letting everyone else know. Communication with the producers and coordinators isn't a bad idea, they're the one's with the lists of names to call when a job comes up!
re: freelancing and improving your odds
The trick is to just work around wherever and whenever you can. I'm on a gig at XXXXX now (one of the shops I've been on hold with for about 50 times but was always booked elsewhere) and I know like 10 people there now from other random gigs or who just got off gigs with friends of mine, etc. So working breeds work. The folks I'm working with now will spread out and assuming I don't f&;^k up too bad, will remember me for a while and put my name in the hat wherever they move to. And I'll do the same. Before you know it, you'll know someone at just about every shop in town.
re: recruiters and reps
Recruiters are absolutely worthwhile. If only to get you INTO the places in the first place. At that point, it's the same as if you got the job yourself. Sometimes recruiters will get you mixed up with weird, painful little one off jobs, but even those pay the bills and you never know whether it'll be worth it or not in the long run, but money's money. It's a nice little backup, since you don't owe them anything while they try to drum up work. They also usually take their cut from the company or are fine pumping up your rate a bit to cover their fee if they can't. So you never really lose there.They can also help track down payments even if they didn't get you the gig (for some small percentage). I'd rather pay $150 or so to collect $5K and not have to be the heavy in some business relationship gone pear-shaped.
Probably also worth getting yourself an scorp or LLC for billing purposes. F^%k those EOR's. I literally just got an LLC (had billed through a rep of mine for years, but it became a tax problem for her) just for the job I'm on now. And it paid for itself in about 1 1/2  weeks of work. XXXX(EOR) wanted 20% out of the first $10K (and 10% thereafter)! 20%! For submitting an invoice and not much else. As I said, f&;*k them. LLC's are easy. Scorps are bit more of pain re: taxes and such, but I know plenty of people who have em. I had my accountant help me but have friends who have done it online also.
That help?
Send me your contact info and reel and I'll pass it on when I can (cuz that's how it works!).
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So there it is. 
Some caveats: Obviously names of studios and stuff have been redacted. Always wanted to redact something. . .
I'd also bet that there are some gotchas re: the specific implications of LLC's/S-Corps etc. As I said, I had my accountant do it. Safer and easier and not much more expensive.
Bottom line re: holds, bookings, freelancing in general. . . If you're pretty good at what you do and (much) more importantly a pleasant person to be around, your dance card will fill up eventually. I've been in conversations with producers who will say things like "Nope. We can't hire her, she made some offensive statement around the EP. He hates her" or "Awww. So and so. He's such a good guy. Let's call him in" or "We had this one dude in and he looked like he was on crack. Not doing that again". Seriously. You will spend a LOT of time with the people you work with. Being a diligent worker and a nice person goes like 75% of the way to getting calls back and kickin ass at what you do doesn't hurt. If you are GREAT at what you do AND you're a good person to be around, you will work constantly, at least in any city that has a reasonable amount of work (I'm not making any assertions about my skills or how pleasant I am to be around:) But I can remember the name of every crazy talented, cool co-worker I've worked with over the years. It's not a big list, but I know that all of them work whenever and pretty much wherever they want (not to delve too deep into their inner wishes or anything . . .). I'd recommend (or hire) any of them in a heartbeat. Just saying. Work hard and be nice. It'll be like the shampoo commercial "she told her friend and she told her friend, and so on and so on. . . " Am I dating myself with that reference?
Be honest about what you can and can't do. Get help when you're in the weeds and be honest about how long things will take you. If you having a crappy experience, tough it out (unless it's crazy or abusive) and cross that name off your list of places you'll work in the future. It's really not that hard and if you like variety (and pressure) freelancing can be a fun lifestyle. Sometimes. 
Happy hunting!