The Future of PocketSmith on Mobile

Over the coming year or so, we’re changing how we deliver PocketSmith to you on mobile. Following some essential improvements to the PocketSmith Sidekick mobile application (namely, transaction splitting and budget analysis date selection), we will work toward deprecating the current PocketSmith Sidekick applications.

Our focus will be on making the web application fully mobile-responsive, meaning it’ll be as functional and useful on your phone’s web browser as on your computer. Once we’re nearly there, we’ll work on delivering a new native app that wraps the web app up for delivery on the iOS and Android app stores but with enhancements for mobile.

There, it’ll appear as just “PocketSmith”, not “PocketSmith Sidekick”. Because then — finally — it’ll be the full PocketSmith experience on your phone, not a companion application experience.

In this post, I’ll discuss the storied history of PocketSmith on your phone, why things are changing and what is happening next. Buckle up; this is a long blog post (we’re old), so let’s kick off with a table of contents.

1. Why is PocketSmith a web application?
2. History of PocketSmith in your pocket
   a. 2012-2015: Mobsmith
   b. 2015-2016: PocketSmith Companion, with Nativescript
   c. 2016-2020: PocketSmith Sidekick
   d. 2020-2024: Maintenance mode
   
3. Why we’re changing tack now
   a. The web can now be completely mobile-responsive
   b. Keeping parity with a fast-changing web app is very hard
   c. Phones are as fast as computers now
   d. In 2024, there are many options for packaging a web app as a native app
   e. PocketSmith is web software company, not a mobile software company
   
4. What our plans are for the coming year
   a. Stage 1: Key features into PocketSmith Sidekick
   b. Stage 2: Make PocketSmith entirely mobile responsive
   c. Stage 3: Start a new PocketSmith native app
   d. Stage 4: Let PocketSmith Sidekick retire
   
5. And that’s all folks

Why is PocketSmith a web application?

Building applications for the web is in our DNA, both as a company and as founders. My co-founder Jason and I cut our teeth in the early 2000s at a web development agency, long before the first iPhone was released. We incorporated PocketSmith on June 23, 2008 — 17 days before the Apple App Store opened for business on July 10, 2008.

Working with the web provides PocketSmith with many advantages: improvements can be delivered directly to users in a matter of minutes after they’re completed; it’s inherently cross-platform at its core; and there are effectively no gatekeepers limiting the delivery of your application to users.

By contrast, developing for mobile is nearly the complete opposite. Improvements can take days or weeks to be delivered to users and only happen once your application has been reviewed by the gatekeepers — of which there is one for each distinct platform. For people steeped in the golden age of the internet, this feels diabolical!

Nevertheless, it’s always been clear that having PocketSmith on your smartphone is essential, so we started on a relatively unfamiliar journey and ended up where we are today.

History of PocketSmith in your pocket

PocketSmith on mobile had three full iterations appear in a short five-year timeframe, starting in 2012 and culminating in the PocketSmith Sidekick app, which exists today and was released in 2017.

The below gets a bit inside-baseball — if you’re not interested in the entire history from a fairly tech-centric angle, please feel free to skip to the next section, or straight to what our plans are for the coming year.

2012-2015: Mobsmith

Our first attempt was a separate web application, built by us when PocketSmith was just Jason and myself. It was lovingly named Mobsmith and lived on mobile.pocketsmith.com. It even had an offline mode to cache data for offline use once it had been loaded. It felt very progressive for the time.

Unfortunately, Mobsmith was unwieldy to maintain, and shipping main-application features slowed down. The offline support was a bit patchy, and despite big talk from Apple about progressive web apps with the launch of the iPhone, the tech didn’t catch on in the early 2010s – not with the App Store around.

Worse, though, was that performance on 2012-era phones was fairly poor —the internet was slow, the chips that phones ran on were slow, and mobile operating systems were still in their early days. Overall, it was a sub-par experience.

Mobsmith limped along for a few years after launch (primarily because I had a thing for the Mobsmith-only safe-to-spend feature) until we decided to give mobile development another shot in 2015 once a few more web software engineers were on the team.

2015-2016: PocketSmith Companion, with Nativescript

A framework called Nativescript was released in 2015. It promised to allow developers to use web technologies to deploy native mobile apps across multiple platforms at once, with one codebase. It was a dream come true! If this could be achieved, it would be ideal for us as a web application company.

This mobile app never got fully released. It was very early for cross-platform mobile development, and as a result, the applications were extremely slow. Nativescript was still very young and had few features, meaning relatively simple things like menus took a lot of work — everything still had to be built by hand. In addition, natural app interactions for Android vs. iOS apps were very different back then — and there was no built-in support for these differences.

The final nail in the coffin came at the start of 2016: Apple rejected the app outright because we didn’t build in the ability to pay for PocketSmith subscriptions within the app (and pay them their cut). This was far beyond both Nativescript’s and our own capabilities at the time. Countless other subscription-based applications (e.g. Netflix, Spotify, etc.) had been accepted before us without issue — unfortunately, our timing fell right in the midst of a policy change, and we were too small to really push back.

Nearly a year had been spent on the mobile app, and then a further six months was spent trying to get it past the gatekeeper. The web app was not getting the attention it deserved, so we finally bit the bullet and hired real mobile engineers to build real native mobile apps in 2016.

2016-2020: PocketSmith Sidekick

With our first talented, dedicated mobile engineer joining us in mid-2016 and our second in 2017, we were off to a great start. A fantastic base was built for the mobile applications, and on the web side, we focused on delivering the required APIs for a brand new mobile experience: native apps for both iOS and Android.

We released the fully native apps in 2017, alongside a shiny new Apple Subscription option, so the gatekeepers (or Shrek, at the entrance of the swamp, I suppose) could claim their 30%.

PocketSmith Sidekick is the result of this. From this era, many years of improvements to the native app followed. This was the end game — the native apps were blazingly fast, modern apps built on the latest technologies for iOS and Android.

We didn’t neglect the apps, however they still fell behind as their lightweight features couldn’t keep up with what we offered on the web. We’d solved our users’ primary need for a proper native mobile app. However, because we moved so quickly on the web, many features have always been missing from these native applications, and that gap continued to grow. So why is that the case, and how did this happen?

2020-2024: Maintenance mode

When our last mobile software engineer left in 2020 to pursue an amazing career opportunity in Australia, we decided not to hire a replacement. COVID was in full swing, and we had other things to focus on. We had already been finding it very challenging to balance a totally separate stream of mobile product and API work alongside our natural state of producing a web application.

We quickly discovered that it takes a village to raise an application. Having a couple of excellent mobile engineers didn’t suffice — without full-time product structures around them, from vision to design to backend engineering, it didn’t work.

To provide support for PocketSmith Sidekick at this juncture, we started working with a great mobile app development consultancy (whom we’d now consider to be a “partner”, as cheesy as that is). This allowed us to keep the app up-to-date with new iOS and Android versions and make tweaks and changes as needed.

Since then, there has been a small handful of updates, primarily the massive upgrade to our bank feeds system in 2021. But aside from that, we’ve only been keeping up-to-date with iOS and Android operating system updates.

Why we’re changing tack now

We have a few specific company and engineering reasons why it’s time to take a different approach, which will be discussed here. However, I also have a personal belief that, while nascent, has encouraged me to lead the company down this particular path.

Namely, personal finances should not be confined to small screens. Amazing things are achieved on larger screens, and managing your money is something to be achieved. What our users do in support of their households daily is no small feat, destined for a small screen.

Phones are designed for consumption, not creation. Brain-rot might be posted on TikTok from a phone, but nourishing content — video essays, long-form writing, novels, music, shows, and movies — is all created on larger screens. Why should managing money be dumbed down to a small screen?

This might be a very Boomer take (or, more accurately, an elder millennial take). A take from someone who grew up with dial-up internet accessed through a CRT monitor. Indeed, in 2015 — during the height of mobile-is-everything mania — this might be considered madness. But with sentiment shifting in younger generations and more people making healthier digital decisions each day, I believe there is a good chance that my take will be sustainable in the long term, too.

There will always be mobile-oriented personal finance applications, offering a small-screen view for organizing your transactions and seeing some valuable reports. PocketSmith stands in contrast to this, offering flexibility, depth, and a non-dogmatic approach to your money. Ultimately, this is what the web affords us.

Anyway, let’s now get into the non-opinion based reasons as to why now is the time for us to change how we deliver PocketSmith on mobile. Despite the rant above, this project is designed to enhance your overall experience of using PocketSmith on your phone. I still want to categorize and check my budgets on my phone too!

1. The web can now be completely mobile-responsive

First and foremost, this change is because it’s now possible to give you the whole PocketSmith experience on your phone directly from the website.

The tooling around mobile-responsive web applications has come a long way in the past decade. In the era of Mobsmith, the most effective way we found to achieve a good mobile web experience was to develop a completely separate web application customized to the limitations of the era’s phones.

Now, however, our team is doing fantastic work building mobile-web versions of updated and new features while they’re getting built for the desktop.

Each new feature that we release or upgrade on the web app is being rebuilt to work perfectly on mobile. At this point, about 1/5 of the feature pages on the web app are reasonable to use on mobile — the goal is to reach all the features.

2. Keeping parity with a fast-changing web app is hard

We pride ourselves on PocketSmith’s flexibility. Being able to tweak the application to suit customer needs, fix bugs, and deliver improvements swiftly is paramount to our identity as a company and product.

Not being able to do the same for mobile immediately is frustrating. An exciting customization setting like changing what day your month starts on would require additions to our API, changes to two different mobile apps, new test builds being distributed, and then finally reviews from Google and Apple. This process alone would take weeks to complete, instead of the few days it took to deliver the same improvement on the web — available to everyone, all at once.

Once the new PocketSmith mobile app is released, we expect that new features will be released as swiftly as they are for the web app — because they’re effectively the same app.

3. Phones are as fast as computers now

Mobsmith was limited due to the underpowered mobile devices of the early 2010s. Using Javascript-heavy applications on your phone in this era was very painful, meaning building lightweight dedicated mobile web applications was wise. Simply put, in 2012 there was a gulf in raw performance between a desktop computer CPU and a mobile phone CPU.

Now, however, smartphone CPUs are on par performance-wise with desktop computer CPUs and can even be faster. Desktop computers are trending towards using mobile-based CPU architectures across both macOS and now Windows — that’s how strong the advances in power efficiency and computational power have been. This is due nearly entirely to the proliferation of phones.

The above illustrates that in 2015, laptops had nearly twice the single-core CPU performance of phones. Move forward to 2021 though, and the phones being released matched the CPU performance of laptops of the same year. Single-core CPU performance is what matters for web-applications, and it’s clear that there is scarcely any difference between phones and laptops anymore.

So the worries about running Javascript-heavy web applications on phones are a thing of the past. Modern phones can efficiently run the modern PocketSmith web, just as well as desktop computers. Only the layout needs to change to account for the smaller screen.

4. In 2024, there are many options for packaging a web app as a native app

It’s essential that we take advantage of the unique advantages of a native app while also delivering the full PocketSmith experience. This means using your camera to add receipts to PocketSmith, delivering timely notifications to your phone, and hopefully, some level of offline access.

Happily, the landscape is different from just a few years ago. The promise of Progressive Web Apps (PWAs) via service workers has picked up since 2020, and the iOS and Android app stores have relaxed their stance on wrapped web apps. The tooling is better than ever.

We now find ourselves in the world we could only dream of in 2016, because…

5. PocketSmith is web software company, not a mobile software company

Looking beyond the examination of why we’re a web application company above, it’s important to consider the deeper reasons why this makes sense.

We’re a bootstrapped business, and so it’s essential to our customer focus and our longevity that we play to our strengths. Supporting a dedicated mobile development team takes a lot of time and money. Not only in hiring mobile engineers but throughout the entire product development stack — design, product management, and API engineering.

Keeping a development pipeline full of interesting and impactful work for talented engineers is challenging — even for a single team of web engineers. Feeding the pipeline for multiple engineers working on separate iOS and Android applications is a huge challenge.

So, by pulling back from the edge, we’ll be better able to focus on delivering the long-term needs of our users.

What our plans are for the coming year

Deprecating PocketSmith Sidekick will take a while — as stated above; we have probably around 80% of the application to upgrade to better mobile responsiveness. So, without further ado, here are the stages we see as at the end of 2024.

Stage 1: Key features into PocketSmith Sidekick

PocketSmith Sidekick is often seen as disappointing because its features don’t match like-for-like with the web application. We agree — indeed, the whole purpose of these changes is to solve this key issue with a fully responsive and wrapped web application.

In the meantime, we’ve performed some analysis on the specific feedback we’ve received about the mobile apps, and three key missing features repeatedly come up.

First, the bad news: we won’t be solving advisor access for the PocketSmith Sidekick apps. The security model around advisor access means this would be time-consuming and not worthwhile when the ultimate goal is to deprecate the PocketSmith Sidekick apps.

Good news: we’ll be working on making splitting transactions operational in the apps and introducing better date range selection options for the Budget analysis pages. These two were at the top of the list of things that need to be solved for everyday users of the Sidekick apps.

While our mobile app development partners undertake this stage, we’ll continue with Stage 2.

Stage 2: Make PocketSmith entirely mobile responsive, end-to-end

This is a large task, but excellent inroads have been made this year. We’re rebuilding more features into modern front-end web frameworks, which are attuned to being adjusted for mobile web experiences.

We’re not sure what order we’ll tackle the features in yet. Chances are we’ll focus on the features that have had long-planned updates, like the Income and Expense pages, along with very high-traffic pages like the Transactions and Calendar pages. All new features will be fully mobile responsive, and some existing features can be tweaked to suit mobile without too much effort.

Another large portion of work will be the interfaces outside of the main app features, such as the various settings modals that pop up throughout the app. This work, in particular, would have a large payoff once solved — entire tracts of the app would then be more usable on mobile — but this work needs to be scheduled alongside the more impactful feature work.

At some point during this process, we’ll recommend that people start to use the “add to home screen” feature on their mobile browser. At this point, or before, we’ll kick off stage 3.

Stage 3: Start a new PocketSmith native app, wrapping the now-responsive web app

Our mobile app development partners already know the plans we discuss here. We’ll be working with them as soon as it’s practical to implement the new version of the PocketSmith mobile app.

They’ll focus on bringing the web app to a native experience and the accoutrements expected from a mobile app, like camera integrations and notifications. On our side of things, we’ll ensure that all the experiences in PocketSmith Sidekick also exist in the web app - for example, there are likely some mobile dashboard widgets that don’t yet exist in the web app dashboard.

We have no timeframe for what this will ultimately be completed. The investigation into how we achieve our goals will be ongoing this coming year as we figure out what exactly is involved in web app development versus native app development.

The end goal, however, will be to release “PocketSmith” on the app stores, where it’ll initially sit alongside PocketSmith Sidekick until we…

Stage 4: Let PocketSmith Sidekick retire and reflect upon a near-decade of service

At some point, we will need to remove PocketSmith Sidekick from the app stores as we’ll no longer be updating the app to support the latest versions of iOS and Android. What is unclear is whether we’d do this right away or not.

Either way, after removal, people with the app already on their phones are able to keep using it. We sincerely hope they won’t want to, given what we would have achieved in previous stages!

And that’s all folks

It feels great to open things up and discuss our plans for mobile with everyone. The apps have been in stasis for years now. This conversation started when multiple team members wondered, what exactly is our mobile strategy?

Now everyone knows — it will be more PocketSmithy, relying on pushing the envelope with what is possible on the web. I’m confident you’ll all love the result — and we appreciate your patience while we get there.

Thank you to all our customers for an amazing year — we’re so pleased you’re along for the ride. Merry festivities to everyone, and see you in 2025!

James is the CTO and co-founder at PocketSmith. He loves tech from software to hardware to music, and is passionate about technology being a net-positive in people’s lives. He lives off-grid with three humans, one axolotl, one rabbit, one dog, and too many possums.