The Spreadsheet That Worked. Until It Didn't.
I have three kids. Twins plus one more. Our family medical spend runs north of $7,000 a year, and that is in a healthy year. Pediatrician copays, ear infections, dental cleanings, two rounds of strep, one urgent care visit nobody saw coming.
For about a year I tracked all of it on a Google Sheet. Five columns. Date, provider, amount, category, paid by HSA yes/no. It took maybe two minutes per receipt. I felt organized.
Then it broke. Slowly at first, then all at once.
This post is what 12 months of spreadsheet tracking actually taught me. I built Tripl after this. But the spreadsheet was not the villain. It just stopped scaling with how my family actually uses an HSA. If you are weighing options, the best HSA tracker apps compares the field.
Months 1 Through 6: Everything Was Fine
The first half of the year was easy. I had maybe 30 to 40 receipts in the sheet. I knew where most of them came from. I could scroll the sheet in 10 seconds and see the full picture.
The folder of receipt images sat in Google Drive. IMG_4827.jpg. IMG_4828.jpg. Mostly screenshots from the patient portal or photos I took at the pharmacy counter. Not great, but the sheet was the source of truth. The folder was just backup.
If you are running a household with one or two medical visits a year, a spreadsheet is genuinely fine. I am not here to tell anyone they need a tool. Most people do not.
Month 7: The Receipt Folder Turned on Me
In July my daughter needed a dental thing that turned into three appointments and two prescriptions. My HSA provider asked me to substantiate one charge. Standard stuff.
So I went to find the receipt. IMG_4912.jpg? IMG_4934.jpg? No idea. I scrolled through 60 photos in Google Drive trying to remember which date matched which provider. It took 10 minutes to find one receipt.
That was the first crack. The sheet had the data. The folder had the proof. But the two were not connected. Nothing in row 23 of the sheet pointed me to the right image in the folder. I had to rebuild the link in my head every time. This is the lost HSA receipts problem in miniature.
I started naming files better. "2026-07-15-dental-cleaning.jpg." Helped a little. But I would forget for a week. Then dump 5 receipts into the folder with their original camera names. Back where I started.
Month 9: Reimbursements Broke the Math
The real failure came when I tried to reimburse myself.
Here is the thing nobody tells you about HSA reimbursements. They almost never line up one-to-one with expenses. You do not pay out of pocket for one thing, then pull exactly that amount back later. You let three or four expenses pile up. Then you pull a round number out of your HSA and pay yourself back.
So I would have a row that looked like this. $437 reimbursement on October 12th. Which expenses did that cover? The $180 ER copay from August? The $89 strep test? The $168 prescription? All three? Two of them plus part of a third?
I added a column. Then another. "Reimbursed amount." "Reimbursed date." "Notes." My formulas got long. =SUMIF this minus SUMIF that. My totals stopped reconciling with my HSA provider's statement.
I am a COO. I run a finance team. I should be able to keep a five-column sheet straight. And I could not. Not because I am bad at spreadsheets. Because the spreadsheet was not built to track a many-to-many relationship. One reimbursement. Three expenses. The math wants a database, not a grid.
The One Question I Could Not Answer
Around month 11, I tried to answer a simple question. How much can I reimburse myself right now, tax-free?
I have unreimbursed expenses going back years. Some from this HSA. Some from the previous one I had before I changed jobs. I switched HSA providers twice in 4 years. Once because of a job change. Once because the new investment options were better. Each switch left a trail of receipts I had not pulled the cash on yet.
The IRS lets you reimburse yourself for any qualified expense that happened after your HSA was opened. No time limit. This is a real strategy. See why your HSA reimbursement record matters and the HSA reimbursement trick. Let the HSA grow tax-free for years, then pull the matching dollars out whenever you want them.
But to use that strategy you need to know the number. How much in unreimbursed receipts do I actually have?
The spreadsheet could not tell me. Not without 30 minutes of formula surgery. And I did not trust the answer when I got it.
That is when I started building.
What I Built Instead
I am the COO at TrainerRoad. I build software at night and on weekends. When the spreadsheet broke I started building Tripl. It is an HSA receipt tracker. It costs $30 a year for the first 100 sign-ups, then $50.
The stack is Next.js, Supabase, Drizzle. Receipt parsing runs through Claude Haiku. None of that matters to a user. What matters is the four things it does that the spreadsheet could not.
Thing 1: The Receipt and the Row Are the Same Object
In the spreadsheet, the receipt was a JPEG in a folder. The row in the sheet was a separate thing. You linked them with discipline. And eventually with prayer.
In Tripl, you upload the receipt. The AI reads the date, amount, and provider. It creates the row. The image and the data are one record. Click the row, see the receipt. No more scrolling Google Drive.
This sounds small. It is the thing that saves the most time. Finding a 2-year-old receipt during a substantiation request used to take 10 minutes. Now it takes 5 seconds.
Thing 2: AI Reads the Receipt
This was the part I underestimated. Manual entry is not hard. But it is friction. And friction is what kills tracking habits.
Snap a photo of a receipt. The AI pulls the amount, date, and merchant. Suggests a category. You hit save. About 4 seconds of work per receipt.
I did not think this would matter much when I started building. I was wrong. My wife uses Tripl now too. She would not have used the spreadsheet. The phone-camera-to-record flow is the difference.
Thing 3: Reimbursements That Actually Reconcile
This was the whole reason I started building. The reimbursement model in Tripl handles the many-to-many problem the spreadsheet could not.
You can reimburse one expense at a time if that is how you do it. Or you can do what most people actually do. Pull a round number out of your HSA. Hit "Quick Reimburse." The app applies it to your oldest unreimbursed receipts first.
The math reconciles. Every reimbursement is linked to specific expenses. The total tax-free withdrawable amount is always one number on the dashboard, updated in real time. At tax time, the data flows cleanly into Form 8889.
That number was the question I could not answer in month 11. Now it is the first thing I see when I open the app.
Thing 4: A Single Source of Truth
The spreadsheet was the data. The Drive folder was the receipts. My email was where some receipts arrived as PDFs. My phone camera roll had the rest. My HSA provider's portal had the official transaction history.
Five places. No single source of truth.
Tripl pulls all of that into one place. You can email receipts to a custom address (mine is receipts@triplapp.com routing). You can upload from your phone via QR code. You can drag and drop on the desktop. You can connect Google Drive for two-way sync if you still want a folder. Whatever the input, the output is one ledger.
When my HSA provider asks me to substantiate something now, I open Tripl, find the row, click the receipt. Done.
When a Spreadsheet Is Actually Fine
I want to be honest here. A spreadsheet is the right tool for plenty of people.
One or two medical visits a year and you swipe the HSA debit card for everything? Skip the app. You do not really need a spreadsheet either. Your HSA provider's portal has the history.
If your annual medical spend is under $1,500, careful tracking versus just swiping the card is a wash. Do whatever takes less time.
If you are the kind of person who genuinely loves spreadsheets and has built a working system, keep it. I am not the enemy of spreadsheets. I lived in them for a year.
The spreadsheet starts to break when:
- ●Your annual receipt count gets above about 30
- ●You have multiple HSA providers (current job, old job, spouse's)
- ●You want to do delayed reimbursements (let the HSA grow, pay yourself back later)
- ●You want to know your tax-free withdrawable balance at any moment
That is when the grid stops being enough.
The Honest Trade-Off
Tripl is not free of friction. You have to upload receipts. You have to trust an AI to read them correctly (and check its work, especially for handwritten ones). You have to log in. You have to learn the interface.
The spreadsheet is also not free of friction. You have to type the data. You have to maintain the formulas. You have to remember which IMG_4827.jpg is which. You have to manually figure out reimbursement totals.
I would say Tripl saves me about 15 minutes per receipt over the year. Not on entry. On finding things, reconciling reimbursements, answering my HSA provider's questions, and figuring out my tax-free withdrawable number.
For a family with $7,000+ in annual medical spend across multiple providers, that adds up. For someone with two copays a year, it might not.
What 12 Months Taught Me
The spreadsheet did not fail because spreadsheets are bad. It failed because HSA tracking is not a spreadsheet problem. It is a database problem disguised as a spreadsheet problem.
Receipts are images. Expenses are records. Reimbursements are many-to-many relationships. The "how much can I withdraw tax-free right now" answer requires a query, not a SUM formula.
I did not start out trying to build a competitor to anything. I just wanted to answer four questions without losing 30 minutes:
- ●Where is the receipt for that ER visit in 2024?
- ●Did I already reimburse myself for that?
- ●How much can I pull tax-free right now?
- ●What is the total of unreimbursed expenses across both my HSAs?
The spreadsheet could answer none of those quickly. Tripl answers all four in under 5 seconds.
That is the whole story.
Frequently Asked Questions
What does Tripl cost?
$30/year for the first 100 sign-ups. Then $50/year. One price. No tiers, no add-ons.
Can I import my existing spreadsheet?
You can. CSV import is supported. The categories may not map exactly to Tripl's categories, so plan to spot-check after import. I imported my own sheet on day one and it took about 10 minutes.
What about privacy and data?
Your data is stored in Supabase with row-level security. Receipts go to encrypted storage. I have admin access for support and debugging, but I do not browse user receipts as part of normal operations. There is admin tooling for support cases, but no analytics on individual receipt content. I do not sell or share data with third parties.
Do I need an HSA provider that integrates with Tripl?
No. Tripl is provider-agnostic. It is a tracker, not a bank. Whatever HSA provider you use, you log into Tripl manually. Or via email forwarding, QR code upload, or Drive sync. Your HSA provider does not need to know Tripl exists.
What if I switch HSA providers?
This is one of the reasons I built it. I have switched twice in 4 years. Tripl is your record, not your provider's. Receipts and reimbursement history stay with you across provider changes. That alone made the rebuild worth it for me.
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*Brandon Nied is the founder of Tripl. He is not a CPA, CFP, or licensed financial advisor. This post reflects research and personal experience tracking HSA expenses for a family of five. Always confirm tax positions with a qualified professional.*
*This is educational content, not financial or tax advice. Consult a qualified professional before making decisions about your HSA.*