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Re:Ask HN: My startup has more annual subscribers than month... by throwaway_23124 on Thursday April 15, 2021 @04:22PM (#26825651)
>On the yearly subscription, do you charge for the entire year upfront?

Yes. The annual subscription is < $250/year, so I don't believe it's expensive enough to stop people purely because it's a big charge.

>How is the distribution of vintages of your user base?

My startup is fairly new (12-18 months old), so I don't have much insight into such statistics. However, I will note that growth has somewhat stagnated (<4% MRR growth every month). While I'm not looking to grow rapidly and I don't have any external pressure to grow (no VCs :)), perhaps the stagnation is a good motivation to introduce segmentation, higher prices, etc.

>it’s almost always a good idea to do it without disrupting (too much) your existing user base.

Absolutely. I always grandfather existing users and I have a few dozen very early users who are paying peanuts compared to the current pricing. I value their super early feedback a lot in shaping my startup, so I'm happy to grandfather their subscriptions forever. I even get emails every now and then from some early users asking if I could "upgrade" them to the current, higher pricing!

Re:Ask HN: My startup has more annual subscribers than month... by holletron on Thursday April 15, 2021 @04:51PM (#26825969)
> Yes. The annual subscription is < $250/year, so I don't believe it's expensive enough to stop people purely because it's a big charge.

One point to add - If I bought it for a month and liked in enough, I'd get annual for that price just to save me the hassle of getting invoices/receipts each month and having to run them through accounting. One payment, one invoice, done for the year.

Re:Ask HN: My startup has more annual subscribers than month... by matco11 on Thursday April 15, 2021 @04:41PM (#26825871)
Sounds great. Maybe, in addition to working on price segmentation, one way to leverage the behavior (“stickiness” as you call it) of your users is to create a mechanism to make them refer new customers to you: you can create an inexpensive growth engine, for example like Dropbox did with its referral program.