Indie Frame #6 — Kaylee Calderolla has a hit on her hands with Wipr 2!

Kaylee Calderolla

Q: Welcome! Please tell us about yourself, and how you became an indie dev on Apple platforms?

I’m Kaylee from Italy (the part of Italy with Venice and Prosecco)!

I started making apps in 2010 – as soon as I held an iPhone for the first time I immediately knew I wanted to make software for it, so I used my fist part-time coding job money to buy a Mac 😊 I kept doing it as kind of a hobby, even during 2012-2014 when I was working for a startup in SF, and slowly (very slowly) I was able to grow it until I could live off it.

I hate giving orders but I’m too opinionated to take ‘em, so indie is kind of my only option 😃

Marc: That’s an interesting path, not dissimilar to mine. I was doing web app contracting for startups until 2013 or so when a combination of factors meant I could spend 6 months full time getting my first iOS app together. I’m not nearly at the stage where I can go fully indie though!

Kaylee: Gotta get more devs to buy Shareshot then 😊

Q: So you have a few apps in your portfolio, tell us a bit about them and which, if any, is your main focus and how it’s going.

I’m gonna pick 3!

Wipr, a content blocker for Safari, is the app I work on the most – in fact if I knew how much work making a blocker was, I’m not sure I would’ve started one 😆 I‘ve launched version 2 a few days ago and it’s going pretty well!

Two screenshots of Wipr 2

I’m currently developing a puzzle game called Tatami (available in open beta). It’s like Shikaku gone wild 😆 — I’m super super excited about this project, can’t wait to finish it!

I also made ExoVoice a while back, a text-to-speech app that you can just pick up and use right away. I originally designed it for people who have laryngeal surgery and can’t speak for some time, but then I get contacted by autistic users who are sometimes nonverbal, or even couples that use the on-screen large text to communicate with each other silently – it’s been super interesting.

Marc: That is really fascinating and heart-warming. I saw the app on your site and wondered what the use cases for that were. Did you do anything to promote ExoVoice to non-verbal autistic users or are they finding it organically?

Kaylee: No, it just happened — maybe they were just searching for text-to-speech apps 🤷‍♀️

Q: I have purchased Wipr 2 and noticed how you went to town on the UI and visuals for an app that really lives in the browser. Do you do the visual design yourself as well as coding or do you work with somebody for that? What does that process look like?

I did the design as well. I’m a better coder than I am a designer, but I eventually manage to make something I’m proud of – it just takes a long time 😊

Feedback from beta users has been really helpful here, then I asked Ben Rice (maker of Obscura — Ed.) to validate my design as well and got some nice tips!

Marc: Oh that really is impressive. I love how you use animation and the rain & lightning graphics in it. It makes it fun and shows you care.

Kaylee: Thanks! Yeah even if your app’s UI isn’t gonna be used a lot, I don’t think that’s an excuse to make it bare. First use should still be a memorable experience, and now you have one more reason to go back to it sometime.

Q: An app like Wipr probably has a very diverse user base, compared to something say like a game or a niche app like Shareshot. How has that been in terms of customer support and reviews? I can imagine it could be pretty rough given the range of user understanding?

Yep, first rule of design is “know your user” but if your user is everybody that doesn’t help much! That’s basically why my website says “I make apps for humans” 😆

There were a few cases of users misunderstanding the system completely e.g. thinking that just reporting a broken site will ensure it was fixed by the next blocklist update. Or telling me to “add” a site with ads to the blocklist, like all I’m doing is cataloguing sites that have ads, and the blocking itself is just magic. But that doesn’t result in issues generally, they’re fairly simple misunderstandings to explain.

As for reviews, I haven’t read any in many years. It was disastrous for my mental health, and near-useless to improve the app – it’s always “best app ever” or “total garbage fire”, no motivations, no desire to see the app fixed – just venting.

Screenshot of macOS App Store charts showing Wipr 2 at #1

Q: It seems congratulations are in order — I saw you posting that Wipr 2 was #1 in Paid Apps of one of the Mac App Stores, above Logic Pro and DaisyDisk! How do you feel about Mac as a platform vs. iOS and did you go the Catalyst route or raw SwiftUI/AppKit?

“Everything’s harder on the Mac” is something I say quite frequently right after sighing! I decided pretty early to make a Catalyst app, not just because it shields me from some of the Mac’s complications, but because it gives me access to some features that are simply absent on macOS and result in a better end-user experience.

Marc: That’s a great point, although my own experience with Catalyst for a couple of projects has not been great, and I am toying with Shareshot being straight up SwiftUI, or at least updating the code base to make sure that remains an option. Things like silly problems with window title & navigation bar tool items really kill me!

Kaylee: SwiftUI has some good bits and some bad bits; the good ones work fine everywhere. In the end you always end up designing apps in a way that’s informed by the strengths and weaknesses of the tools you use.

Q: With some #1 chart rankings on iOS too, things must be pretty wild. How does it feel, and what impact is the attention having on you?

I’m in a weird place emotionally! Feedback has been 99% positive but that 1% is huge in my mind. I’ve also realized that the more praise I get, the more impostor syndrome I feel… I am overall happy that people like my work though, and that I finally managed to launch.

User feedback is currently coming in faster than I can deal with it – so I’m pretty overwhelmed!

I think my favorite bit was hearing Nileane pronounce my name with a French accent on the podcast Comfort Zone.

Marc: Ha — I need to check out that episode! It’s certainly a great feeling to feel validated by the community. I can imagine that the level of user feedback you must be getting with this attention is overwhelming.

Do you have any strategies for dealing with prioritisation of fixes and features? At the launch of Shareshot I was tracking every bit of beta and user feedback in a Notion table, linking it through to the chunks of work required for them to be fulfilled and applying a relative difficulty score to those tasks to prioritise at least the initial big features to prioritise.

Kaylee: So for context; users send feedback with the app itself, and I read it with an internal app I’ve made. This was all so no one had to use email, thus revealing their email address to me.

Yesterday I had to add two features to this internal app: search, and priority filtering (which shows feedbacks about sites that have the most reports). Otherwise I couldn’t even approach the pile! So basically I try to work on the issues affecting the most users first. Nothing revolutionary.

As for features, the beta ran for so long (mostly because of some horrible OS bugs) that I was able to implement pretty much everything I wanted, other than light mode in the app, which I definitely will add as soon as I can.

Q: How have you been using Shareshot, and are there any particular features you’d like us to add?

Every screenshot you see on my website, App Store, and assorted promotional material has been framed with Shareshot 😊

Marc: That is so great to hear!

Kaylee: One thing I do a lot is putting two framed screenshots side by side; I automated the process with a small script that invokes ImageMagick, but it would be nice to have that built-in – sounds really tricky to design, though!

Marc: Yes, we feel your pain! This is one of the big 3 features we are prioritising. We have a lot of groundwork to do to get there, as like you say it’s not just about the basic functionality — the design and interaction needs to be smart and make sense!

(Note: this kind of thing can be done right now using Shortcuts instead of ImageMagick — after all Federico’s O.G. Apple Frames shortcut does this from scratch for individual images. You can use Shareshot to generate multiple images on a clear background and then composite them, or something like this 3-up with a background shortcut).

Kaylee: I’d also like a macOS version obviously 😊

Marc: Ha! Help me out with my Catalyst woes and maybe we’ll get there sooner. I’m still not sure how great it will really be, because we do little quality of life things that are perhaps only possible/make sense on iOS. Obviously I love macOS in terms of a desktop computing platform but I vastly prefer iOS and visionOS UI style and this doesn’t necessarily work well on the Mac.


Kaylee’s apps can be found on Bluesky and on the web. You can also follow her apps on Mastodon.

If you are an indie who enjoys using Shareshot and fancy being featured in a future instalment of “Indie Frame”, please contact me. We love to share the love!

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