When, and how should I think about getting money out of a free site/service?

How to (slightly) monetize a tiny niche website... when it's free to use?

I'm developing a small niche website to help an airline worker I know solve a problem she faces fairly regularly. It seems certain to me that many other people with her job in her industry face this same problem and I can fix it for them too. (apologies for being so vague, I haven't bought the .com yet)

This is a hobby site, so I'm not really worried about making a ton of money and crossing the freedom line. I would, however, like to have it at least break even (for hosting etc)

What kind of ways can I try to get a little cash moving on a free site?
Here are the things I see other people doing:

1. Offer a paid "pro" version with extra features: not relevant for me right now. maybe possible someday
2. Adwords or other targeted advertising
3. Affiliate links to products (link to Amazon for example)
4. Beg for money

Am I jumping the gun even worrying about this now? (I have enough cash for at least a year of overhead costs and I don't plan to quit my day job)
Am I better off waiting to see if I get more than one user?

Tips? Advice? Ideas?

I'd say that if the idea doesn't seem monetizable, then don't worry about it. Just do it as a hobby and have a good time. It will reduce the pressure and stress on you and allow you to just enjoy yourself.

What are your overhead costs, maybe $20-$50 a month for hosting? That's probably the max you should by paying for an app that serves a handful of people and doesn't do anything ultra-complex. Realistically, in almost all cases you could probably get by on shared hosting for ~ $10/month.

I don't think that kind of money is worth even worrying about. Just go out to lunch 1 fewer time each month and you've offset the cost.

Good question. I think a lot depends on how useful the site is?
If what you have can work for all {?flight attendants?} in some way then I see 2 options.

1.) If what you have helps them, but doesn't directly help the airlines... consider a realy low subscription... (e.g. $9.95-$19.95/yr)

2.) If what you have helps them, AND the airline itself... consider approaching an airline about a larger scale subscription by the airline itself

Keeping in mind with #2, depending on what your software does, there may be all kinds of security/red tape issues...

Otherwise if you think neither will bite... consider ad based support until there is a big enough customer base that will buy-in.

Advertising comes with the cost of a depressed user experience. Sure, most people ignore ads but its not the immediate impact that matters; ads convey something to your audience - are you a passionate personality who wants to create a community or are you trying to make a buck?

That said. Start with Adsense. One line of code to get started and you'll get a sense for the potential upside.

If using WordPress, use a site like OIO Publisher or BuySellAds.com to start soliciting advertising on a fixed fee basis. You'll get better ads than Google and can charge a premium by setting your cost at $250 instead of a CPM or other traditional metric based on performance. Such a platform also handles everything for you so you only need to set it up and forget it.

Stay away from affiliate until you have 10k readers or 1M page views a month. Any less isn't really worth the effort. You'll see what I mean when you add Adsense; you aren't going to make much.

I like the premium model but you have to offer something exceptional. Best advice in this regard? Set up a SurveyGizmo survey and just as you readers if and what they'd be willing to pay.

Just my own relatively unexperienced opinion. (so take it with a grain of salt)

1 might not be a good idea as most general airline staff probably do not get paid enough to purchase or subscribe to a service that might make their job a little easier.

2 and 3 should be fairly easy to do in a short amount of time. It will also help offset the cost of maintaining your site, if only by a bit.

4 is entirely up to you and your personal pride and/or pocketbook.

If I were you, I would think about developing this service with the ultimate goal of possibly being able to sell it to the airlines themselves. If it makes their own employees more efficient, then why would they not want to implement it?

You could also use your free service to market value added services at a fee, similar to what pingdom does: they allow you to use their application for free, however if you want to be alerted via sms you buy credits.

If you have the resources, why not do a little market research and determine if your application can be generalized enough to be of interest to a market.

Then, you can look at who may benefit the most from making the lives of their employees easier, so they can be more productive, and they are the ones that you would hope would buy the product.

It sounds like right now is too early to be wondering how to make money, until you have a better idea of what the product will be, as one user is not really a good design for a product, IMO.