Chapter 21 of 32 · Money
Finance: connecting your money
Finance works like a bookkeeper who never sleeps. Connect your bank accounts and Stripe, or upload a statement, and Winston sorts every transaction, charts it and checks it for tax savings. It's read-only: Winston can see your money but can never move it. All amounts are in US dollars. Everything in this chapter happens on the Books & taxes view.
How it works
What you can do here
- Connect a bank or credit card securely through Plaid
- Bring in Stripe sales, refunds and fees
- Upload a bank statement as a CSV file instead
- Have every transaction sorted into a category, and correct any Winston gets wrong
- Find tax write-offs and strategies to look at with your accountant
1. Get started in 3 steps
- 1
Open Finance, then Books & taxes
Finance is in the Money group. Books & taxes is one of the views along the top.
- 2
Connect your bank or credit card
Press Connect your bank or credit card. You sign in to your bank in a secure Plaid window. Your password goes to your bank, not to Winston.
- 3
Add Stripe
If you take card payments with Stripe, press Add Stripe. It brings in your sales, refunds and Stripe fees. If Stripe isn't set up yet, press Set up Stripe; it asks a few questions, then brings you back.
- 4
Or upload a statement
No bank connection? On your bank's website, download your transactions as a CSV file, then press Upload a bank statement (CSV).
2. Uploading a statement
- 1
Choose the CSV file
Pick the file you downloaded from your bank.
- 2
Say which account it is
Pick an existing account, or A new account and give it a name, such as Chase business checking.
- 3
Credit card files
If it's a credit card file where purchases show as positive numbers, tick the box so spending isn't counted as income.
- 4
Upload
Winston reads every row and sorts it.
Uploaded statements show spending, but not your bank balance. Connect the bank to see live cash on hand.
3. Checking your transactions
- 1
Find the list
Your transactions are listed under your accounts. Use Search and the Money in, Money out and Not counted filters.
- 2
Check Winston's categories
Categories Winston picked are marked. If one is wrong, pick the right one from the list.
- 3
Let him learn
When you correct a category, Winston fixes matching transactions too and remembers it for next time.
4. Finding tax savings
- 1
Press Find tax savings
It takes about a minute while Winston checks this year's rules against your books.
- 2
Read the write-offs
Write-offs in your books lists spending you can likely deduct, and what to keep as proof.
- 3
Look at the strategies
Strategies to look at, each with a next step, and Watch out for, things that could cause trouble.
- 4
Check with a professional
These are ideas, not tax advice. Confirm every write-off and strategy with a CPA before you file.
Try it yourself
Doing is the fastest way to learn. Open the tab and try these:
- Upload one month's bank statement as a CSV.
- Correct one transaction's category and watch the matching ones update.
Common questions
Can Winston move my money?
No. The bank connection is read-only. Winston can see transactions and balances, never move money.