r/roastmystartup • u/JoaoRochaOnReddit • 4d ago

Roast my time-off calendar for couples. I just launched paid plans and I honestly have no idea if the pricing makes sense

My wife and I both work full time. Different employers, different PTO allowances, 1 or 2 different public holidays. Every January we sit down and try to plan the whole year off together and it always turns into a spreadsheet nightmare.

So I built something. A shared year calendar where you can add two people, see when you're both free automatically, track each person's remaining PTO days, and handle all the public holiday differences per country.

It just got a full redesign last week and I added paid plans. Here's where I need the roast.

The pricing:

Free: one person, no card required. You get the full calendar, public holidays for 190+ countries, custom company days.

Pro: $1.99/month or $0.99/month billed yearly ($11.88/year). Adds sharing so your partner can see and edit too. 7-day free trial included.

Lifetime: $14.99 once. Everything in Pro, forever.

My logic was that this is a "vitamin" product, not a painkiller. It makes life nicer but people aren't going to die without it. So the price has to be impulse-buy level or nobody converts. The lifetime deal is there to give people an obvious anchor.

Current state: about 21 signups. One person actually uses it properly (has their whole 2026 mapped out). The rest signed up and haven't come back.

I'm a software engineer building this as a side project before my day job starts. This is my first real attempt at building something people pay for.

Questions I genuinely need answers to:

  1. Does the pricing feel right for a personal tool like this, or does even $1.99/month feel like friction for something that's not mission-critical?
  2. The free plan already includes overlap highlighting and sharing (the partner joins free). Is that too generous? Am I giving away the whole product?
  3. 21 signups, 1 active user. Is that a product problem, a marketing problem, or just "too early to tell"?

Roast me. I'd rather hear it now than after I've spent another 6 months on this.

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2

u/HalfBakedTheorem 3d ago

the google calendar question is the real roast here, that's the wall every couples planner tool runs into

1

u/JoaoRochaOnReddit 2d ago

That's true.
Google calendar might not be perfect for this specific use case, but it does the job I guess.

1

u/Shoddy-Chemistry2864 2d ago

Yep, this is the classic "why wouldn't I just use Google Calendar + sheets" problem. Even if your tool is 10x better, convincing couples to adopt a whole new workflow when they already have something that kinda works is brutal. Most people will stick with their janky spreadsheet setup rather than learn a new system, especially for something they only touch a few times a year.

1

u/brain_tank 4d ago

Why pay when Google does this free?

1

u/JoaoRochaOnReddit 4d ago

That's exatcly what comes to mind..

But I still feel that Google Calendar is very cluttered, and full of other stuff.

We used to do this in a Google Spreadsheet, wait.. do you mean Google Sheet and not Google Calendar?

1

u/brain_tank 4d ago

No, Google calendar.

My wife and I have a shared calendar for planning vacations, keeping current on kids activities, etc.

1

u/miaowyes 4d ago

Why pay when Notion Calendar does this for free?

1

u/JoaoRochaOnReddit 4d ago

Well I didn't know about that one honestly, I was using Google Sheets where I was building a calendar for each year.

1

u/therealbigshoww 4d ago

I loved that you solved your own problem but I tend to agree. A lot of free options. Did you try any of them before you built your version ?

1

u/JoaoRochaOnReddit 4d ago

Yes, I was actually using Google Sheets. But I was a bit tired of creating a new calendar for each year: with all the correct days of the calendar, mark all public holidays.

And I felt that it was a simple tool that was useful to me, so maybe it would be useful for others, that I created it.

1

u/brain_tank 3d ago

Why use sheets when there is calendar?

1

u/JoaoRochaOnReddit 3d ago

Because you don't have yearly view on Google Calendar.

I want to view the entire calendar

1

u/brain_tank 3d ago

There is a year view on calendar. I'm looking at it now.

1

u/JoaoRochaOnReddit 2d ago

Yes, but you don't see any events do you?

1

u/adoboggwp 4d ago

too many free options. what makes your app stands out that people would have a reason to pay? did you ever consider that maybe you're solving a problem that don't need a solution?

1

u/JoaoRochaOnReddit 4d ago

I mean, I'm solving my own problem so I thought that there might be others that would feel the same.

Maybe I'm wrong and there are no other people that like to have everything organized and planned for the whole year in advance, or they exist but are not willing to pay for such a tool because it's too simple.

I think the problem is that this is a vitamin SaaS, not a pain killer.

1

u/roberthcmn 3d ago

As previous comments already mentioned many free options and calendar space feels very crowded. Why not give the corefunctionality away for free but for payed users offer more. Let's say you can extend this calendar from couples to the exteded family and friends... it's always a discussion of aligning everybody for a holiday or vacation. Think of thigs that other calendars don't offer and have that as a payed feature. Keep free what others offer for free already.

1

u/soarling1 3d ago

Unfortunately, I feel this is more of a feature of another product than a product in itself. I, for one, would be unlikely to pay for something like this.

The low signup number could be too early to tell by itself. At this stage, I would rely more on the qualitative data you are getting.

1

u/JoaoRochaOnReddit 2d ago

I agree, it might be too simple to be its own product.

I'll give it a few more months while I start working on something else.