I routinely send key projects, particularly smaller projects, a request to quote me a commercial license of their project, with the explanation that I would accept a quote of $1,000 and that the commercial license can be their existing OSS license plus an invoice. My books suggest we've spent $3k on this in 2015. My bookkeeper, accountant, and the IRS/NTA are united on this issue: they don't care whether a software license is OSS or not. A $1k invoice is a $1k invoice; as a software company, I have virtually carte blanche to expense any software I think is reasonably required, and I think our OSS is reasonably required.
I would do this more often if OSS projects made it easier for me to do so. Getting me to pay $1,000 for software is easy; committing me to doing lots of admin work over the course of a week is less easy. Take a look at what e.g. http://sidekiq.org/ , which is an OSS project with a commercial model, does. Two clicks gets me to a credit card form. If I actually used Sidekiq, Mike would have had my credit card on file the day that form went up.
Why aren't you allowed to donate?
> I routinely send key projects, particularly smaller projects, a request to quote me a ...
Sounds like an excuse to not donate - or did you ever get a response? Why not just donate $100 once and feel good about it?
The company has books. All money into the company and out of the company is recorded on those books, in a fashion meeting various legal requirements of both countries. If I say "Donation" next to a line item and the NTA reviews it they'll say "Not allowed; adjust this item to be a distribution to yourself, pay income taxes on it, and don't do this again or we'll be very cross with you." If it says "Software license" the 99.999% case is "Seems reasonable" and the 0.001% case is "Random line-item audit: produce the documentation about this", to which I say "Here's an invoice" and they say "Alrighty then."
Sounds like an excuse to not donate
Again, I do not donate. I just send checks for thousands of dollars to OSS projects.
Well, I rest my case - kudos to you.
Of course, you as a business owner do make money from your business, so just donating privately remains a valid option.
I work for a medium sized company with sub 1k employees across many countries and jurisdictions. Knowing when/how/where our company can legally donate to anything is a problem at the intersection of legal, accounting and marketing, groups I have very little influence with and even less interest in embedding myself in. In fact, I assume there is some committee at our company for charitable works, but I don't know anything about who is on it, how to contact it etc. Even if I did, the idea of a) explaining what OSS is and b) trying to argue for using our charitable contributions budget on OSS software vs cancer research, low income literacy, or whatever else we currently support seems down right icky.
Because you see, OSS isn't a charity for us. We use OSS to solve business problems. It provides real business value that I (and my colleagues) are very cognizant of and would be happy to pay for. If an OSS project had an invoice and a credit card form my process for getting them cash looks like this "ME:Hey $manager_type_with_payment_card give me the card, I need to spend $some_value_less_than_payment_card_transaction_max on some software we use all the time. THEM:Why? ME:My time explaining it will cost the company more than $some_value_less_than_payment_card_transaction_max." THEM: Cool, here you go." Contrast that with the above nightmare of meetings and committees and you can understand why I don't even try to get my company to "donate" to OSS.
There is a lesson for SaaS business in there as well. A recurring charge is much like a donation in that it requires me to navigate a lot of hurdles. A one time fee for a time limited license on the other hand falls into the payment card conversation above. So you are much more likely to get me to pay you $500 for 1 year of access to your software and no recurring contract, than you are to get me to pay $5 a month recurring.
If I pay you $1k for something, you get $1k and I pay less taxes on x - $1k. If you ask me to donate $1k, I probably can't (or I'd have to pay extra corporate tax on the gifted amount, i.e. $1k + x% CT). Some jurisdictions allow you to "gift" 5% of your taxable income, in others it's capped to a certain amount (i.e. €2500) but only to accredited non profit entities.
Now, I could donate personally, but fiscally that isn't too great. Think about this stuff, seriously. That $100 donation could be $200 (at no extra cost to me), if you just considered the tax situation. Who am I kidding? I'll just donate $200 to the other guy who did consider it.
But in general it seems that most business owners I worked for don't think about that also open source and free software projects need money to be kept alive an thriving.