I Pasted My Bank Statements into ChatGPT and Immediately Regretted It

How one bad idea turned into Ask Linc.

It started with a layoff.
Which, if you’ve ever been through one, you know is just a corporate way of saying: “Good luck out there. Here’s a box for your desk plants.” (And even worse when you work remote. They basically just log you out of Slack, you close your laptop, and then, freak out.)

So there I was — no job, too much coffee, and a brain that couldn’t stop running math on my future. How long could we coast before needing another paycheck? Could we still retire on schedule? Would our savings survive if our car suddenly decided to become a toaster?

So, I turned to ChatGPT.

The Bad Idea

Like any desperate, slightly sleep-deprived person, I thought:
What if I just paste my entire financial life into this thing and ask what to do?

So I did.

Account balances. CD maturity dates. Stock holdings. Retirement contributions. Mortgage info. Screenshots. Spreadsheets.

It was a beautiful mess. A masterpiece of oversharing.

And the answer I got back? Fine. Just fine.
It was like asking a stranger at a bar for life advice and getting a shrug and a “Yeah, man, sounds like you’re doing okay.”

The problem wasn’t that ChatGPT was dumb. The problem was it didn’t actually know my numbers. I had to feed it everything manually — which was slow, clunky, and felt about as secure as yelling my Social Security number in a crowded subway car.

The “Wait a Second” Moment

Somewhere between “ugh, this is terrible” and “I’m too far in to stop,” I had a thought:

What if ChatGPT could have all my real financial info, securely, automatically — and I could just… ask it things?

• Are we still on track to retire at 62?
• Can I move that CD money into something better?
• If the Fed hikes rates again, what happens to my mortgage?

No massive copy-paste jobs. No re-explaining my situation every time. Just context. Real, live, up-to-date context.

Building the Thing

I’m a product person by trade, which means my brain is broken in a very specific way: the moment I spot a gap, I start designing the bridge.

So I built Ask Linc.
It connects to your financial accounts via Plaid (the same tech your bank app uses) and pulls in real-time market data. Then it uses GPT to give you answers in plain English, with your actual situation in mind.

Instead of “the average mortgage rate is 6.63%,” it can say, “Your mortgage is at 6.85%, so refinancing right now probably isn’t worth it.”

Instead of “the S&P 500 is up 0.77%,” it can say, “Your portfolio’s tech-heavy, so today’s rally added $X to your total.”

And because I’m me, it also has a sense of humor. Finance is already stressful enough without sounding like a 300-page Federal Reserve PDF.

The Newsletter (Because I Like Talking)

While I was building Linc, I realized: the daily and weekly market updates I was pulling in for context were… actually kind of interesting.

So I started writing them for friends. Then friends-of-friends. Then strangers on the internet. Short, readable posts that tell you what’s happening with the economy, markets, and rates — and why you should care — in the time it takes to drink your coffee.

And here we are:

• Ask Linc, the financial assistant that knows your numbers
• The Ask Linc Substack, for bite-sized market sanity
• This blog, for everything else – market news, product updates, etc

Why Bother?

Because most finance content is either:

• Too boring (Hello, 14-paragraph explanations of the yield curve)
• Too hyped (“CRASH IMMINENT, MOVE TO GOLD!”)
• Or too generic (“Cut back on avocado toast” — thanks, Dave)

I wanted something better. Something that works for normal people who want to make smarter decisions without living in spreadsheets.

If you’ve ever wished your money apps could just explain what’s going on — clearly, honestly, and maybe even with a little snark — you’re in the right place.

Welcome to Ask Linc.

💬 Want the daily(ish) updates? Subscribe to the Substack — it’s free, it’s quick, and it’s way more fun than reading your bank’s monthly market outlook PDF.