Building an app is a series of decisions. Some feel obvious; others require weeks of iteration. Building Checkout meant understanding what servers actually need—not what a product manager imagines they need, but what works after a brutal double shift.
This post is a behind-the-scenes look at those decisions: why Checkout exists, what I prioritized, and what I deliberately left out.
Why Build a Tip Tracker?
I worked in restaurants through college. I know the experience: finishing a shift exhausted, cash crumpled in your pocket, credit card tips on a printed slip. The idea of opening an app and entering data feels like one more task on a night when all you want is to go home.
Most tip trackers are built by developers who've never worked a shift. You can tell by the friction: too many fields, unnecessary features, designs that don't account for tired fingers and low patience.
I wanted to build something different. An app that takes 15 seconds to log a shift. That doesn't require creating an account. That keeps your financial data actually private.
Checkout exists because I would have wanted it when I was serving.
Design Principle: Speed First
The most important feature of a tip tracker is that you actually use it. Every second of friction reduces the chance you'll log tonight's shift.
Minimal Required Fields
Checkout asks for four things:
- Cash tips
- Credit tips
- Hours worked
- Date (auto-populated)
That's it for basic logging. Hourly wage, employer, position—all optional. You can add them later or never. The core action is: open app, enter tips, done.
One-Tap Date Selection
The date defaults to today. If you're logging yesterday's shift, one tap. Last week? A few taps. The calendar is right there, no nested menus.
No Confirmation Dialogs
Tap save, shift is saved. No "Are you sure?" No "Shift logged successfully!" banner. The screen updates, you see your new entry, you're done.
These micro-decisions add up. A tracker that takes 15 seconds gets used. One that takes 45 seconds gets abandoned.
Design Principle: Simplicity Over Features
Feature creep kills apps. Every feature adds cognitive load, maintenance burden, and opportunities for bugs. For Checkout, I was aggressive about what didn't make the cut.
No Tip Pooling Calculator
Some apps include elaborate tip-out calculators. Enter your sales, tip percentage, bussers' share, bartender percentage, etc.
I cut it. Here's why: tip pooling arrangements vary wildly between restaurants. Building a flexible enough calculator adds significant complexity. And servers already know what they take home—they counted it when they cashed out.
Checkout tracks what you took home, not the math of how you got there.
No Social Features
No sharing shifts on social media. No leaderboards comparing tips with friends. No "achievements" for logging streaks.
Tip tracking is personal financial data. Adding social features requires accounts, servers, and data sharing—exactly what Checkout avoids.
No Scheduling
Some tip trackers include shift scheduling. View your upcoming shifts, get reminders, etc.
This overlaps with dedicated scheduling apps and your restaurant's own system. Checkout stays focused: track what happened, not what's planned.
No Receipt Scanning
OCR to scan checkout receipts sounds convenient. In practice: OCR is unreliable, receipts vary wildly between POS systems, and it's often faster to just type two numbers than to position a camera, wait for scanning, and correct errors.
Sometimes the boring solution is better.
Privacy Architecture
Every app I build starts with a question: what if I stored no user data?
For Checkout, this wasn't compromise—it was liberation.
No Account System
Accounts enable sync, but they also enable surveillance. Every account ties data to an identity. Every server log, every database entry, every analytics event becomes connected to a real person.
Checkout has no accounts. You download it, you use it. Your identity never enters my systems.
Local-First Storage
Tip data stores on your device using iOS's native persistence. The data lives in your app sandbox, protected by iOS security, encrypted when your device is locked.
I never receive this data. It doesn't traverse the network. It physically cannot be breached on my end because it doesn't exist there.
Your iCloud, Your Keys
What about backup? What about syncing between iPhone and iPad?
Checkout uses iCloud sync—but your iCloud, not mine. Apple handles the encryption with keys only you possess. The data flows through Apple's infrastructure (which has its own strong privacy practices), never through mine.
This means I literally cannot access your tip records. Not if asked. Not if subpoenaed. Not if my systems were compromised. The architecture makes access impossible.
Download Checkout and own your data
Platform Decisions
iOS Native
Checkout is built natively for iOS. No cross-platform frameworks, no web views.
Why native matters:
Performance feels right. Scrolling, gestures, animations—native apps get these details right because they're using the platform's actual implementation.
System integration is seamless. Dark mode just works. Dynamic Type accessibility just works.
Supported Platforms
Checkout runs on:
- iPhone (iOS 18.5+)
- iPad (iPadOS)
- Mac (macOS 15.5+)
No Android (Yet?)
Checkout is iOS only. This was pragmatic: I'm one developer. Building for one platform well is better than building for two platforms poorly. For now, Checkout focuses on being excellent for iOS users.
Monetization
Subscription Model
Checkout Pro is $1.99/month or $19.99/year, with a 3-day free trial.
I chose subscription over one-time purchase for a specific reason: tip tracking apps need ongoing maintenance. Tax laws change. iOS updates require adaptation. Users expect bug fixes and improvements.
Subscriptions fund that work. One-time purchases create misaligned incentives—the developer is paid up front and ongoing investment reduces profitability.
That said, Checkout's subscription is affordable. $1.99/month is about the cost of one of your customer's tips. If the app saves you money through better tax tracking, or helps you earn more through goal-setting, it pays for itself.
Generous Free Tier
The free version of Checkout is actually useful:
- Log unlimited shifts
- Basic analytics
- Export to CSV
Pro adds:
- Extended analytics and comparisons
- Unlimited history (free has rolling window)
- Weekly goal tracking
- All future Pro features
Someone who only needs basic tracking can use Checkout forever for free. Pro is for people who want deeper insights.
What I'd Do Differently
Looking back, some things I'd change:
Launched too late. I polished for too long before shipping. Real feedback from real servers would have improved the app faster.
Underestimated edge cases. Restaurants are weird. Double shifts, split positions, mid-shift job changes—there are more edge cases than I anticipated.
More user research earlier. I relied on my own experience serving, which was years ago. Things change. Talking to more current servers earlier would have helped.
But the core decisions—privacy-first, speed-focused, native iOS—I'd make again.
Building Forward
Checkout is live and evolving. User feedback shapes the roadmap. The architecture—local-first, no accounts, no server infrastructure—keeps things simple and maintainable.
If you're a server or bartender, download Checkout from the App Store. Try it for a few shifts. Let me know what works and what doesn't.
And if you're a developer building apps for specific communities: talk to them. Understand their real workflows, not the imagined ones. The best products come from genuine understanding, not assumptions.
Your users know what they need. Your job is to listen and build it well.