Now in private beta

Chat with
your finances.

Connect your accounts and get a financial agent that watches your money, flags what's off, and answers any question — right inside ChatGPT, Claude, or your favorite AI client.

Works inside ChatGPT + more
Driggsby
Driggsby 5 accounts connected via Plaid
What's unusual with my money this month?
D
Checking 5 accounts, 847 transactions...
Found 3 things worth looking at:
Duplicate charge
Spotify is billing you $15.99/mo on two different cards — Visa ••4821 and Amex ••3711. That's $192/yr.
Price increase
Your car insurance went from $148/mo to $207/mo at renewal in December. That's an extra $708/yr.
Annual charge
A $659.88 Adobe Creative Cloud charge hit your Visa on Feb 3. Same charge last year — looks like an annual renewal.

What you can ask

Every question you've had
about your money.

Spending
"How much did I spend on dining out last month?"
Retirement
"How much am I putting into my 401k each month and what will it be worth in 20 years?"
Subscriptions
"List every recurring charge I'm paying for."
Cash flow
"Am I spending more than I'm earning each month?"
Anomalies
"Are there any duplicate or unusual charges this month?"
Taxes
"Show me all charitable donations and medical expenses from 2025."
Net worth
"What's my total net worth across all accounts?"
Saving
"How much can I safely auto-save each month based on my spending?"
Debt
"What's the fastest way to pay off my credit cards?"
Investments
"What's in my 401k and how is it allocated?"
Income
"How much am I actually taking home each month after everything?"
Search
"Find every Amazon charge over $100 this year."

Always watching

Your money never sleeps.
Neither does Driggsby.

Driggsby is watching
Live
Electric bill $287 — 40% higher than your 3-month average
2h ago
ParkMobile charged $4.50 twice on Mar 8
yesterday
Car insurance renewed at $214/mo — was $181 last year
3 days ago
Free trial converted: $24.99/mo to Headspace since Jan
1 week ago
Annual renewal: $139.00 to Adobe — same charge last March
2 weeks ago
Spotify went from $10.99 to $13.99/mo last cycle
2 weeks ago
6 findings this month View all →

Connect all your accounts
in seconds.

Driggsby uses Plaid to securely link your banks, credit cards, investments, and loans. It's the same connection you've already used with Venmo, Robinhood, or Coinbase — same flow, same security, same trust.

Connect your accounts to Driggsby
Select your financial institutions
C
Chase
Checking, Savings, Credit Card
S
Charles Schwab
Brokerage, IRA
A
American Express
Credit Card
W
Wells Fargo
Mortgage
Secured by

What Driggsby does

Your money, understood.
Not just displayed.

Ask anything

What's my net worth? How much did I spend on food? Where's my money going? Just ask — in plain English.

Anomaly detection

Duplicate charges, price increases, transactions that don't fit the pattern — Driggsby surfaces what looks off.

Retirement & goals

See how much you're contributing to retirement accounts, track your savings rate over time, and set targets Driggsby monitors for you.

Save on autopilot

Driggsby analyzes your income and spending patterns to tell you exactly how much you can safely set aside each month.

Tax-ready

When tax season hits, pull together charitable donations, medical expenses, income summaries, and investment activity in seconds.

Works where you do

Use Driggsby inside ChatGPT, Claude, or your favorite AI client. Coming soon: terminal and custom AI integrations.

Security

Built for the question
you're about to ask.

Bank-level security. No compromises. No fine print.

Driggsby never...
Sees your bank password
You log in through Plaid, not us. Your bank credentials go directly to your bank — they never touch our servers.
Moves or touches your money
Driggsby can't initiate transfers, payments, or trades. It's architecturally impossible — we only request read permissions from Plaid.
Sells or shares your data
Not with advertisers, not with partners, not with anyone. Your financial data exists to serve you and no one else.
Makes it hard to leave
No retention tricks, no dark patterns. Disconnect an account or delete all your data in one click.
Driggsby always...
Uses read-only access
Minimum permissions, maximum visibility. We see balances and transactions so you can ask anything — but we can never act on your accounts.
Encrypts everything
All data encrypted at rest and in transit. We run on Google Cloud infrastructure built to meet Plaid's security and compliance requirements.
Connects through Plaid
The same infrastructure behind Venmo, Robinhood, and Coinbase. Over 12,000 institutions supported, trusted by millions.
Gives you full control
Disconnect any account or delete all your data in one click. No waiting period, no retention tricks, no hoops.

Getting started

Three steps. Two minutes.

01

Connect with Plaid

Link your banks, credit cards, and investments through Plaid's secure connection. Same flow you've used with Venmo, Robinhood, and every other modern finance app.

02

Driggsby indexes your finances

Balances, transactions, recurring charges, liabilities, investments — everything gets pulled together and organized automatically.

03

Start chatting

Open ChatGPT, Claude, or any supported AI client and start asking questions. Set alerts for what you care about, tell Driggsby your financial goals, and let it watch your money over time.

Driggsby running inside Claude Desktop — a real conversation analyzing spending
Driggsby inside Claude Desktop

"What are we actually worth?"

My wife is a CPA. She asked me that one evening after dinner. Not worried. Just curious — the way you'd check the weather before a weekend trip.

We didn't know.

Our money sat in ten different accounts, held together by a spreadsheet last opened six months ago. It was tedious enough that we kept putting it off, and important enough that we felt guilty every time we did. So there I was — copying numbers into Excel like it was 2005.

She wanted to open her phone on any given Tuesday and just know. And she wanted something keeping watch — for the fraudulent charge, the duplicate subscription, the bill that quietly doubled.

It was a simple ask. It just didn't exist yet.

I built Driggsby for her.

Matt May
Matt MayFounder

Your money is
trying to tell you
something.

Driggsby is in private beta. Join the waitlist and find out what you've been missing.