Ask HN: How do I turn my side project into something profitable?

Just a few thoughts:

2. I will guess you are aiming at PMs, in mid sized + large companies (Not aiming at getting an install for every PM in the whole company, just one for whom you solve his / her pain)

3. This suggests you need to integrate easily into the workflow of a PM : which means ActiveSirectory as a identity provider, and probably Atlassian for grabbing tasks. YMMV

4. you cannot run as a SaaS for this market - you need to be installable inside their firewall. the people I am talking about will not touch externally hosted services with a barge pole.

5. So keep the project open source, keep the SaaS as a free trial based in number of seats (effectively offering a free for ever service to small companies willing to externally host, funded by sales to larger companies wanting internal hosting)

6. the actual saleable product : yearly maintenance and install support (charge by the year, that way people can raise a purchase request and just let you chase the invoice - at a certain level say 500/mth upwards - it is worth paying a VA to be the chaser- do not write payments code at all for this ever. only write such code when revenue is enough to pay someone else to write it. repeat it is not your job to collect money or to write code to do the collect / account shutdown etc.

Sell maintenance: three - six months release cycle - that is code goes onto SaaS and into proprietary installer now then onto GitHub in six months. so there is value in the maintenance license

Do not sell yourself for anything other than installation support - you want to be talking to the sysadmin about integrating AD not to the PM about how to reset a password

If you do sell "reset a password" support the do it expensively enough that the first sale is enough to hire a VA or similar to be your front line support. do not do support yourself.

So - sensible suggestions now:

* Take yearly payments via Invoice, this way it's worth your time manually handling the chase up. Don't bother monthly because it is sooooo much simpler to sign up to a free trial by sending a purchase request than actual money

* Don't do time limited trials, but do it by number of seats etc. And do not at all write the code to monitor and shutdown accounts automatically till the SQL query and email cut paste takes you an hour a day alone

* Marketing via guest blogs: there are many project mgmt magazines and blogs. spend Saturday googling and then email a bog standard "please can I write a guest blog" to half of them Saturday evening. you can always do the tailored mails later but you need something to keep you motivated

* Get down to one benefit and sell that for a while. I think the "integrates into your other stuff to give one view" is nice but whatever. Just have a benefit and sell that for 3-6 months, only then let the words lean or pivot into your brain

* email newsletter obviously

* Keep it open source - as above trust is important here - if I cannot trust encryption to keep my stuff safe I need to trust you have written good code - OSS helps there

- so people can host it themselves - it's free, but installer and reporting packages that are licensed bolt ons, with escrow based source code release (stackechange has something like this)

edit: sorry that got a bit long and noprocrast delayed me long enough I have to do real work now so it's a bit of a stream of consciousness

Not sure how much of this applies to you, but this is my advice for anyone trying to monetize a SaaS idea or product:

1. Reach out to people (beyond your friends and family) to gauge interest in the idea. This probably involves networking, cold calls/emails, meetups, etc.

2. If there is any interest from anyone, ask them what specifically they'd need from the product in order for them to consider buying/subscribing.

3. Repeat until you have enough feedback to start understanding your market and their wants/needs. (Also, think about how you'd solve their problems in ways beyond what they simply tell you they need.)

4. If your market is split across different segments (and would require different sets of features) pick the group that seems most engaged and target them exclusively.

5. Once you feel that your product would work well enough for them (this might require one or two more rounds of feedback), throw together a pricing page and the underlying billing infrastructure, and start trying to make sales.

Note: You can always lower your prices, but it's harder to raise them, so start as high as you think could be remotely reasonable -- who knows, the price might still be worth it to your clients. If not, wait a bit and then lower the prices. (Perhaps you can use the new discount as a marketing tactic.)

6. Success? Cool. Think about how you can expand your market without succumbing to feature creep. Not success? Don't worry -- pick another market segment or do more rounds of feedback. It's up to you when to give up and move on, but just because it didn't work this time could mean plenty of things. (Maybe you need more focus on customer acquisition, or maybe you need to hire a designer). The point is, don't give up until you're really sure it won't work.