In terms of video production, what has been the most intimidating aspect for you?

It would be an interesting study to send 25 scouts out to 25 historic mansions to see how many of them could get it free. Can it be done...sure...on some rare occasions. Could you build a sustained production strategy off this? Not anything that would have ongoing success.

Well, I've shot at the same historic mansion twice -- once for the feature 'Afterlife' and once for the short film 'The Silver Key'. When the mansion's owners saw 'The Silver Key', they told me it was the best thing that has ever been shot there. (They get a LOT of weddings shot there.) They asked for a copy of the film so they could play it on a continuous loop in their lobby. Made me proud. :-)

One thing that made it easier to get this particular mansion is that they don't conduct regular tours, do re-enactment events, etc. They are mainly a wedding venue, although they have plans to develop it now into an inn. But yeah, places that do a regular trade with tours and special events would be much harder to secure for free.
 
For me its definately the business side of things. Self Promotion, RFP's, Pricing, paperwork, accounting etc. The doing is what I find fun but its hard to sit down and force yourself to do the non creative stuff. My dream is to build up enough clients that I can hire someone to tackle the business end of things for me.

Exactly the same for me, I would happily shoot and edit all day, but the solicitation of new clients is a horror show.
 
I'm on the other side of this. I hate asking for favors of any kind. I'd love to have the budget/money and pay everyone their full rate - none of that cut rate, deferred, back end, points nonsense. Alas, I don't have the funds. The comeback to that is "well then go get some", which is fine, but not always realistic. But even without $, I still want to shoot stuff. So at that point my options are: 1) ask for favors and freebies, 2) try to do it yourself and with your closest allies, f.ex. wife, family, childhood friend etc., 3) do without. That's where your psychological makeup comes in. Mine is unfortunately not that well suited to the film world, because I pretty much never avail myself of option (1) - I simply cannot bring myself to ask someone to work for free or near-free. So I'm left with options (2) and (3). But with (2) "do it yourself", you really are handicapping yourself, because nobody is going to be great at everything, but more importantly, you simply don't have the physical capacity to take on too many roles - your project will inevitably suffer if you are the director and also the DP and also the lights and sound and grip, and producer, and crafts, and continuity and so on. That's guaranteed. Which is why I often gravitate to option (3), by so structuring the project that I can bring down the complexity as much as possible - limit locations, limit number of actors, limit everything you possibly can, by writing around it, by shooting around it, by improvising and so on. Ultimately, it ends up a combination of trying to do too much myself and putting too many limitations on the material and overall it hurts the project. So there is that side too: while you hate to say no, there are those like me, who hate to ask because we sympathize with your position. A good filmmaker is good at asking people for stuff and motivating them, including motivating them without pay... if you hate to ask, you are going to limit yourself badly. I am aware of this weakness of mine, but don't know how to get around it. We all have our weak points psychologically, and this is mine.

Yeah, Man. I completely get this. I was referring to saying "no" to a lot of OTHER self-producers who have limited budgets and are not shooters and editors and don't DIY this stuff but still want to express themselves with short film or web series or whatever. These are not "my" projects but I still have a hard time saying no even if they don't have a pot to piss in or a window to throw it out of.

For my own projects I'm all #2 and #3 all the time. That's a whole other problem. Like you, I hate asking for favors, would love to pay top rates and cannot and find myself knocking myself out as you describe in 2 and doing without as in 3.

So now I have 2 shorts I'm shooting. I write like I have a budget and then go about doing as you describe. I say, OK, what's essential about this scene (establish the Mom and show her disappointment, or whatever) then I say, I'd like to have this happen at a Neimann Marcus but it ain't cause I ain't getting in there, so I find a restaurant that will take my insurance and make a deal.

I haven't shot my own shorts in a couple of years working on other people projects, some actually with budgets! I'm going back to the Fractured Atlas, Indie Go Go well, with two non-profit projects, crowd funding, some kind of fund raiser and I'll do the best I can that way. My hope is that I've gotten good enough in my writing and directing skills to do a good enough job on these to get one of my features shot with investment next year. Kinda show off what I can do now with some work under my belt.

In all they will have the smallest budgets possible. I will operating probably. Hell, Soderbergh does it, Gareth Edwards in Monsters.. you know. On the day I need an AD, UPM/producer, an AC, a soundie, one gaffer, one grip who will dolly grip, makeup, locations, food, and I can go. I will get volunteers for PAs, from friends and relatives. Hopefully I'll raise enough to get them but they won't be top tier and that's fine. As long as they can get the job done. That's not all of it but you get the idea.

It's true, good producer/filmmakers are great at asking people for favors. I've seen it but I'm not that good at it myself - but I'm learning every time I have to pop out from behind the camera and flag some light and then run back and try to get my bearings ;) Whew...
 
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