Why and how I built the Shoeboxed Magic Mileage Tracker
Here's the whole story, with photos and what we learned with each new version.
Before I bought Shoeboxed, I presented a PowerPoint to my wife about why we should buy it. I talked a lot about how owning our own business would provide more upside and meaning than another corporate CEO gig. I also showed her the big growth areas I saw. Mileage tracking ranked near the top as a great way to grow Shoeboxed.
Why?
Check out the actual slide I showed her. Two of the biggest mileage tracking apps, DriversNote and Everlance, each made about 10 times what Shoeboxed did at the time. 10 times!
Shoeboxed had a free mileage tracker, but to be honest no one wanted to use it. It made users have to remember to open the app and start/stop a trip, it drained your phone battery something fierce, and even crashed my phone when I tried to use it.
Customers and prospects knew Shoeboxed for receipt scanning, but not for mileage tracking. However, our customers wanted both. My theory was that if we could make a great mileage tracker, we could get much closer to the $10M+ DriversNote and Everlance were making.
Note: each company spoke publicly about its revenue numbers, so you can look them up if you want.
I had spent years building software as CEO for various companies, and the last 6 years building hardware devices at MDHearing. I asked myself, could we build something better? Could we build a hardware device that:
- Just worked
- Made our customers' lives easier
- Removed all the annoying things about phone app trackers (battery drain, dropped trips, annoying alerts, etc.)
At the time I wasn't sure, but I was sure it was worth doing the work to find out.
Searching for the "Magic" in mileage tracking
Since 2007, Shoeboxed made scanning paper receipts for customers "magical." Tens of thousands of companies have mailed us their paper receipts in a Magic Envelope, and our team in Durham, North Carolina, scans and digitizes every one. That's pretty magical.
Could we make mileage tracking "magical" too? That was our mission.
In May 2025 I wrote this to my team:
I want to offer dead-simple mileage tracking, with no app required, that logs and uploads your trips automatically. It should just work.
Then came the hard part! Hardware is hard, a lesson hard-learned from my years running one of the largest D2C hearing aid companies in the US.
Magic Mileage Tracker Attempt #1. My first try asked one question, which was whether I could get the thing to work at all. I wired a GPS board, a small computer, a wifi connection, and three AA batteries into a white box, and I wrote ON and OFF next to the switch in pen. In May 2025, it logged its first drive around my neighborhood.
It ran on batteries and had no cell connection. Worse, it only worked if I remembered to flip the switch (which I forgot a few times). However, it worked!
I kept after it, and by July, I got the cell connection working.
Now I knew it worked, so I moved on to proving customers may actually want the thing.
Magic Mileage Tracker Attempt #2. I always pictured something you could "set it and forget it", so the second try was a small puck for the dashboard. It had a solar panel on top to keep it charged, and a big battery to hopefully last a long time between charges. I finally got it working in September 2025, and the first drive showed me what was missing. Here's what I wrote to my team.
I really want a light, or lights, to tell me what's happening. Is there power? Is it tracking? Is it sleeping?
That's why the tracker you get today has a light that blinks while it tracks.
Attempt #2 made a LOT of progress, but it still didn't zing the way I wanted it to. Who wants a big bulky thing on their dashboard? Who wants to remember to have to plug it in if it runs out of juice?
I liked it, but didn't LOVE it yet.
Magic Mileage Tracker Attempt #3, the "Aha!" moment. I was elbows deep in GPS tracking research one day when I came across a GPS tracker built into a car charger.
Holy cr@p! This was it!
A car charger AND a mileage tracker in one? Tell me more!
Who doesn't want a great car charger? I don't know about you, but my kiddos always chirp in, "Can I use the charger?" when they get in the car.
By putting the mileage tracker IN the car charger, we not only solved the battery issue, but we give customers something else they actually really want and need. Every car can use another charger. A mileage tracker is useful, but a mileage tracker that charges your phone is AWESOME.
Finally, I thought we had something. In February 2026, I put our testing unit in my car to personally test it. Here's what I wrote that week.
I LOVE it because it's only on when I drive, and I don't have to worry about phone permissions or my phone's battery.
And after one drive, when I saw what the trip was worth as a tax deduction, I wrote this.
I just made about five bucks on that trip, and it was AWESOME.
Thinking you have something and knowing you have something are two different things.
For months, I drove with it every day and optimized it over and over. I changed how it tracks, how often it reports in, how it learns where home is, and much more. I made well over 100 improvements to it.
After all that testing, I knew we had to launch this.
Final testing. In early October 2026, the first two units of our production tracker passed our testing. I have one in our second car right now.
The faceplate in my car is a sticker we tested. Here's a production sample of the one you get, with the box it ships in:
Launching the Magic Mileage Tracker to the public. It's time! I couldn't be more excited to launch Shoeboxed's Magic Mileage Tracker. We're starting with 100 beta units, and you can reserve yours today. I can't promise we've worked all the kinks out, but I can promise we'll respond quickly and do whatever it takes to make it magical for you too.
Gone are the days of annoying mileage tracker phone app battery drains, or dropped trips. Give the Magic Mileage Tracker a try, I think you'll like it.
- Doug