Ask HN: How to turn a “toy” side project into a business?

- Cold call marketing

- Sell it as a cost-saving technology

- Figure out how much alternatives are costing them and tell what they could be saving

- Offer the paid plan for a trial period

- Limit the size of the organization, but open the free plan to more than one-on-one

- Actually phone up at least one new sign up per day. Ask why they signed up, what they use it for, how it compares the the others they have used and what would they pay for - unlimited time, number participants whatever. They will try to be nice - assume they lie. most importantly how did they hear of you. Pay attention to the vocabulary they use. What you are trying to get here is your elevator pitch - but told to you by your customers "Video chat right in Slack"

- You now have some idea of channels to market - ten people signed up because of a facebook post or because of a linkedin article or a google search - so choose a channel - facebook / linkedin / SEO. Just produce ten articles or pay for ten adverts - and see what traffic changes you get - stick at it - you are looking for a channel to market. Somewhere somehow there is a way of reaching a potential audience - with a sales pitch you learnt from above you want to find where that sales pitch reaches the most of your potential audience

- pricing - this matters less than the above especially as you are aiming at busiesses - I would say Slack has a pricing norm so you may want to charge per user but aim for 30/55/75 or there abouts.

- keep trying new sales pitches, and vary the channels you try slowly.

-

This isn't the answer you want. But I have a hobby side project that I've kept going for a decade, and which gets high enough use to feel like it's worth keeping going.

It costs server money to run, a couple of take-away-coffees per week's worth. In the past I did agonise about putting ads on it, or otherwise monetizing it.

But at some point I decided that as I was lucky enough to have a paying job, the marginal returns I would get by trying to monetize the site wouldn't be worth it, and I was happy to pay for it like any other hobby. The grateful emails I get every couple of weeks make it worthwhile.

That was a very liberating decision. Mix business with pleasure and it stops being fun.

Mind sharing the link to your Hobby project for me to check it out? :)

First question you need to ask: why would someone pay you $30/month to add something to Slack?

The answer to that question is going to be a mystery to anyone reading your homepage. "make working from home less lonely" - I don't know what that means, but I don't know many individuals that want to pay $30/month for it, and it's not a very compelling argument for a business either when the economy is in the toilet and getting worse every day.