Mar 16, 2026

I Asked ChatGPT To Find My Biggest Money Leak — It Wasn't What I Expected

Written by Andrew Lisa
|
Edited by Brendan McGinley
DISCOVER Person using AI on laptop

Barely halfway through January, my New Year's resolution to spend less and save more was already losing inertia, so I figured it was best to identify my single biggest money leak and stop the bleeding where it counted most — but what could it be?



Unenthused by the prospect of tediously combing through statements and adding up the damage, I asked ChatGPT to do it for me.

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Apparently, I consult the AI chatbot so frequently on personal finance matters that it didn't need much input from me, stating, "For people with your profile (active investor, multiple portfolios, tax-aware), the biggest money leak is usually NOT groceries or coffee."

So if those common culprits weren't to blame, then what?

ChatGPT was determined to find out through what it called a "high-confidence triage" of five categories, each with its own series of yes/no questions. It concluded, "Your biggest leak is almost always the first 'YES' you hit."

The chatbot started by outlining "the five biggest money leaks, ranked," explaining why they're a common problem and how much I stand to lose from each. It also noted, correctly, that every dollar wasted is one that isn't compounding in savings.

Remember, ChatGPT advised that my first "yes" is likely the source of my biggest money leak among these five categories.

  • Potential leak: $300 to $700 monthly or $3,600 to $8,400 annually

  • Question: "Do you have 10+ subscriptions (streaming, apps, news, software, cloud storage, gyms)?"

  • My answer: No



  • Potential leak: $25 per day or $9,125 annually

  • Question: "Do you feel like you don't spend much here? If so, you probably do."

  • My answer: No

  • Potential leak: $1,500 to $4,000 per year

  • Question: "Has it been two-plus years since you've shopped for insurance?"

  • My answer: Yes

  • Potential leak: Five figures per year

  • Question: "Do you have assets in the wrong account type? Have you missed credits or depreciation, made timing errors or harvested capital gains you didn't need to realize? Given your investing focus, this is critical."

  • My answer: No

  • Potential leak: Undetermined, but potentially enormous

  • Question: "Do you have an extra car, unmonetized spare rooms, storage units or second properties used inefficiently?"

  • My answer: No

ChatGPT noted that overpriced insurance or excessive coverage is "a very common leak."

In my case, it turned out to be AI-generated words of wisdom.



I'm a minimalist with subscriptions, I'm prudent with discretionary spending and I'm smart enough to know I'm not smart enough to do my own taxes — but it turns out that my set-it-and-forget-it attitude toward insurance was costing me four figures per year.

Unsatisfied with this revelation, ChatGPT asked me to "paste one month of anonymized transactions" into its search box so it could conduct a more thorough analysis ...

I hope it doesn't find out too much.

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.

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Written by
Andrew Lisa
Edited by
Brendan McGinley