Happy Monday, everyone!

We made it to the 21st issue! Thank you to everyone who read last week’s issue ❤️

Some of you who follow me on Twitter (at @joshdholtz) may have seen that me and my wife had our first child this week ❤ I will be giving focus to my family so Indie Dev Monday issues will contain only one super awesome amazingly talented indie dev for a while (instead of two). There may be the occasional two indie dev issue but I want to make sure I can keep some consistency on Indie Dev Monday while balancing my personal life 😊

That being said…

📆 Today I’m featuring Tyler Hillsman.

Tyler is the creator of Pennant and Sticky Widgets. Pennant is a sports app that quickly shows you the standings and stats for the five largest leagues in North American. Sticky Widgets is the easiest way to put a sticky note on your home screen. Pennant is easily my favorite sports, and the only sports app, on my phone. I’ve tried to have other sports apps on my phone in the past but they were always too much for me. I really only ever cared about the standings. I had no reason to look at live scores or any of the other detailed stats. I like my teams but I simply want to know where they stand. Thankfully Tyler had the same problem and solved it with Pennant. Pennant can show where your team stands overall and also in their division, conference, leagues, or whatever they may be called. Pennant also gives the ability for a features called “My Pennant” which allows you to customize different stats and charts across your favorites sports teams. I’m both a Green Bay Packer fan and a Kansas City Chiefs fan and “My Pennant” allows me to keep track of both with no effort 😊 Tyler also makes another great app called Sticky Widgets. To be honest… an app might be a weird word for it since you don’t even need to use the app part of Sticky Widgets 😇 Sticky Widgets is almost 100% used within iOS widgets for viewing and editing. Sticky Widgets gives you that classic sticky note look, feel, and functionality. It’s so beautifully done. Make sure to check out Pennant and Sticky Widgets right now!

👉 Please make sure to follow them or support them anyway you can! 😇 I’m excited to share their indie dev stories.

Indie Devs

Tyler Hillsman

Kansas City, MO, USA

Director of Mobile Apps at Outdoorsy and creator of Pennant and Sticky Widgets

Tyler Hillsman


1) What is your name? Where do you live?

I’m Tyler Hillsman and I live in Kansas City, Missouri.

2) Introduce yourself. Education? Background? Main job? Interests outside of tech? Interests inside of tech?

I’m an iOS developer (turned product manager/engineering lead) by day and iOS developer by night. My day job is Director of Mobile Apps at Outdoorsy, where I lead the mobile product effort and mobile engineering team (iOS + Android). But I’ve had side projects doing my own indie apps since 2013, in addition to contract work (web, design, and apps).

My day job keeps me busy, so indie apps are my nights and weekends projects. They serve as my “scratch my own itch” projects, new-technology playgrounds, and are things I still find fun, despite being in Xcode all day anyway.

Education-wise: I’m not your typical CS degree developer. My bachelors degree is in Marketing and I also have an MBA, but I always had a hobby of web development all through high school and college. While I was in my first post-college job, I started learning about app development and I’m self-taught ever since.

Outside of tech, my wife and two kids keep me busy, and they’re my #1 interest for sure. I also like to read, watch sports (particularly Chiefs football, Royals baseball, and Formula 1), build things (woodworking), and travel (please come back, travel).

3) Have you ever considered yourself an indie developer?

You know, not until recently (~2 years or so). My non-traditional background provided me with more than a little imposter syndrome and I distinctly remember realizing that I could call myself an “iOS developer” in my first day job role that included that responsibility. It wasn’t until later that I thought, well, these other folks I follow have day jobs and side projects and they’re indie devs, so I must be one too.

4) What got you started/interested in creating your own applications outside of your “normal” job?

Great question. It’s a mix of “I want something that does X” and “I wonder if I can make Y”. A bit of a need and a bit of a want. My primary app (Pennant) is more of the first category, and others (like Sticky Widgets) are more of the second.

5) How do you balance your time between friends/family, work, hobbies, and indie dev?

Well that’s the trick, isn’t it? Work is set times, so that’s the starting point. I’m in my second full-time remote role, so I’ve sort of got that down (even pre-pandemic). Family is the highest priority and has a tendency to fill those gaps. (COVID-era arrangements mean even more time with wife and kids.) Friends are certainly a challenge in these times, but thanks to the wonders of the internet, you’re all a few taps on my screen away. I cheat a little with hobbies since that’s also indie dev. That happens almost exclusively on the couch in the evenings. I do try to run or bike every day, so that’s a healthy hobby, I suppose.

6) Pennant - Pennant is the perfect sports app! It’s also the only sports app I have on my phone (besides Fantasy Football). I’ve never really needed live scores but I do need to know where all of my teams stand. Where did the idea for Pennant come from? What were you using before Pennant?

Oh man, Pennant has lived many lives. Until I relaunched it in fall 2019, it was called Race to the Pennant, and it was solely for baseball. I’m a big baseball/Royals fan but before that I was a big aspirational baseball/Royals fan. When I first moved to Kansas City after college, I really wanted to follow the team. (I’d always casually cheered for them, but now the team and I shared a city, so I wanted to go deeper.) But there’s 162 games in a typical MLB season and that’s hard enough to follow for just one team, but I wanted to know where things stood for the division, league, or all of baseball. So I built an Excel file, as you do, and updated it every day. Which, you know, worked but wasn’t scalable. In the winter of 2013, I drew out a UI, taught myself enough to build the app, and the rest is history.

7) Pennant - I’m going to assume based on the name that baseball was the first sport in the app 🙃 What are your requirements for adding other sports? I think I saw that you are also into some kind of racing. Is it possible to add other types of sports like that into Pennant?

Oh yes. When Race to the Pennant launched, it was all baseball. That’s what I was most interested in and fortunately John Gruber shared it on Daring Fireball on Opening Day, so that’s what all my initial user base was interested in. The next logical step was expanding sports… but that took a bit longer than I hoped. I did do a short-lived spinoff for football in 2013, I think, called Race to the Playoffs, but it definitely didn’t have the users and it was too much to maintain. I considered a few strategies of rolling out different flavors of the app, but maintenance, branding, and customized data models seemed daunting. Finally in 2019, I decided to rebrand (simplifying the name to Pennant), rewrite (100% SwiftUI), and expand to multiple sports. I started with the large North American leagues: MLB, NFL, and NBA, then quickly added NHL and MLS. I’ve got quite a to-do list and the next leagues I’m planning on are WNBA, Premier League, La Liga, Bundesliga, and more. Additionally, I definitely want to add event-based sports as well: Formula 1, NASCAR, PGA, etc, but the structure of these sports means changes to my data model so they’ll be more challenging.

8) Pennant - What has been the most fun parts of building Pennant and what has been the most challenging?

Good questions. The most fun part is adopting new technologies as quickly as I’d like. The initial version was built in a proprietary cross-platform language, but when Swift was announced, I learned it and shipped the next build in Swift 1. I had a watchOS app in the store on day 1. I added Siri Shortcuts when they were released. I wrote it in SwiftUI when that was available (even writing some views in San Jose at WWDC 2019). Because it’s my app, it’s my playground to try new things. The most challenging was way back on version 1.0, I was using a third-party API to provide scores… but it only updated at 6:00am the next morning. Users wanted final scores as soon as the games were over (I don’t blame them), so I taught myself PHP in a week, built a backend and a database (manually updating scores meanwhile), and created my own API. That was certainly a week.

9) Sticky Widgets - I love love love this app! I still remember the feels I got the morning you surprise launched this app 🙂 Where you did you get your inspiration for hitting the “New Project” button in Xcode for Sticky Widgets? Was it it just an experiment project or did you know you wanted to ship it?

Sticky Widgets is the crazy science experiment monster that breaks out of the lab. I’ve been consciously trying to ship more rather than adding to the stack of half-developed apps (mostly thanks to your helpful prodding!) and Sticky Widgets was simple enough (I thought) that I could toss it on the store and see if anyone else thought it was clever. It was very much an experiment: widgets aren’t interactive, but can I fake it by launching immediately into a one-screen app, focusing a text cursor for you, and close out of the app when you’re done? I build my proof of concept, did the bare minimum of polish, and tossed it on the store. It was a distraction from Pennant, but if I got it out of my system, I could work on Pennant more, I thought. I was wrong. So it was an experiment project that I experimented with shipping.

10) Sticky Widgets - I’m pretty sure you had a crazy launch! What as your first day/week all like? What kind of expectations did you have going into launch day?

So… there’s a bunch of really good advice out there for what to do when you launch an app: create a site, have a Twitter account, put together a press kit, reach out to press, get beta test feedback, have a monetization strategy… and I did none of it. Like I said, it was just an experiment. So when I published it, I just tweeted about it. It was a Monday morning and I did a little thread that said “hey I built this and it’s kind of clever” with a video that shows how it works and I thought I’d move along with my morning. And then my phone exploded. Very kind people who follow me retweeted it and very kind people who follow them retweeted it and things went nuts. I realized that something big was happening, so I started replying to anyone who asked something about it or complimented it, and I don’t know how many tweets I sent that day, but it was definitely a personal record. I rushed to add an in-app purchase and address very valid feedback and suggestion, and by the end of the week I think I had put out 6-7 updates, had been on 9to5Mac and MacStories, had been discussed on Connected, and had a pretty solid user base. So I had zero expectations and my reality was a divide-by-zero error.

11) Sticky Widgets - The yellow sticky note color is so perfectly beautifully ugly. It’s the only sticky note color I use 😇 I like the classic look. What is your favorite color and font combination to use?

Good question! The classic colors and fonts are meant to do two things: get the point across of what the app does, and make you want something nicer to upgrade to! 😂 For me, I’m the cobbler with no shoes and a million test notes, but I like v2.0’s ability to pick from anything with the color picker. My favorite widget right now is blue angled text on yellow background that says “BELIEVE” and if you haven’t seen Ted Lasso to get the reference, stop what you’re doing and binge it.

12) Pennant and Sticky Widgets - What’s next?! Do you have any fun future features planned that you can share with us? Or do you have any new Xcode projects that you started that you plan on releasing? 😉

Sticky Widgets 2.0 just launched and it was a huge update (really what a non-experiment version of the app should’ve looked like from the beginning): iCloud sync, completely custom colors, styling from within the app, etc. The foundational work means more is possible, but nothing yet to announce.

Pennant’s future is all about additional sports (and updating for the upcoming seasons like NBA starting 12/22) and additional visualizations and widgets. I’m a little addicted to making widgets, so look for more coming there.

And I’ve always got a pile of unfinished apps. One I made in May is almost ready to go, but it’s probably too silly to launch. That probably won’t stop me, though. 😉

13) What’s been the hardest part of being an indie dev? What the most fun part of being an indie dev?

Hardest part is definitely finding the time. If anyone would like to sponsor me to retire to an island and just work on side projects all day, by all means: reach out. But it’s not what pays the bills, so it’s relegated to a smaller chunk of time at the moment. The most fun part is being able to do whatever I want with my apps. I’m an early adopter to a fault with my own apps (I’m much, much more conservative with day job app decisions) and I treat my own apps as playgrounds to explore and have fun. There’s a reason I’d still consider app development to be my biggest hobby.

14) Is there anything else you’d like to tell the indie dev community about you?

I don’t think so. I’ve said too much already.

15) Do you have any other indie devs that readers should follow / lookout for?

Anyone who’s appeared in this newsletter. Josh is an indie-dev discovery machine and I learn about so many awesome people through this newsletter and mutual Twitter friends. I’m only on the outskirts of this community, but it’s something I love and enjoy daily.

Thank you to everybody who made it to this footer! You either spent the time to read or took the effort to scroll 😊

Make sure to visit https://indiedevmonday.com/subscribe to get an email of future issues!

And go to Twitter and give @IndieDevMonday a follow… or multiple follows if you manage more than one Twitter account 😜