Lesson 11 of 16 · Money
Finance
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.
What this tab is for
- 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
- See cash on hand, budget status, top vendors and upcoming payments
- Read Winston's highlights about what changed
- Track cash flow, cash by account and recurring bills
- See profit and loss for the year and by month, and download it as CSV
- Fill a budget from your last three months, and compare budget with actual
- Forecast ending cash with your own scenario
- Add W2 employees and 1099 contractors, salaried or hourly, and schedule bonuses
- Generate a business plan and an investor plan
- Request legal services from RocketLawyer
Option 1 of 12
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).
Option 2 of 12
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.
Option 3 of 12
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.
Option 4 of 12
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.
Option 5 of 12
The Overview
- 1
Cash on hand
Your total across connected accounts.
- 2
Budget status
Each category marked On track, Near limit or Over budget. Press Set your budget to add limits; switch between Monthly and Annual.
- 3
Top 5 vendors by annual cost
Who you pay the most over the last 12 months, with recurring ones marked.
- 4
Upcoming payments
Bills and bonuses Winston expects soon.
- 5
Estimated cash flow
Money in minus money out, with a forecast that follows your last three months. Switch between Month, Quarter and Year.
- 6
Winston's highlights
What changed and what needs you. Once there are a few months of numbers, he points out trends.
Option 6 of 12
The Cash view
- 1
Read the tiles
Cash on hand, Runway (how many months your cash lasts at the current rate) and Net cash this month.
- 2
Cash flow, last 12 months
Income and expenses month by month.
- 3
Cash by account
How much is in each account.
- 4
Recurring bills
Vendors that charged you in at least three of the last six months, with the monthly and yearly cost and when they're next expected.
Recurring bills is the quickest place to find subscriptions you forgot about.
Option 7 of 12
Reports
- 1
Read the year so far
Revenue, expenses and net profit year to date.
- 2
Profit & loss by month
Every month side by side, so you can spot good and bad months.
- 3
Download
Press Download CSV to send it to your accountant or open it in Excel.
Option 8 of 12
Budget vs. actual
- 1
Open Planning
Under Budget vs. actual, every category shows its budget per month and what you really spent.
- 2
Fill it for you
Press Fill from last 3 months and Winston sets each budget from your recent spending. Then adjust.
- 3
Watch the gaps
Each row shows how far over or under budget you are.
Option 9 of 12
Forecast & scenarios
- 1
Start from the base case
The chart shows cash in the bank month by month if things carry on as now.
- 2
Build your scenario
Change revenue, set growth each month, change costs, or add a new monthly cost such as a hire or rent.
- 3
Read the ending cash
See how much cash you'd have, and whether it ever runs low.
Before hiring, add the person's monthly cost as a scenario and check your runway.
Option 10 of 12
Payroll
- 1
Add a team member
Choose W2 employee or 1099 contractor, then salary (monthly pay) or hourly (rate and hours per week). Press Add team member.
- 2
Schedule a bonus
Enter the amount, date and an optional note.
- 3
Read the chart
Payroll by team member and your monthly payroll total. Regular pay runs on the 1st and 15th of every month; bonuses pay out on their own date.
Option 11 of 12
Business plan and investor plan
- 1
Open Business plan
If there's no plan yet, Winston can generate a full business plan and a separate investor-facing plan from your business's blueprint.
- 2
Generate
Press the button and wait a minute or two.
- 3
Read and share
Open each plan to read it.
Option 12 of 12
Legal services
- 1
Open Legal
Company formation and legal documents are handled by Winston's partner, RocketLawyer. Winston doesn't give legal advice himself.
- 2
Request a service
Choose what you need (forming an LLC, an EIN, an NDA, a contract review, a trademark and more), add your details and send the request.
Your exercise
Before you finish, open the tab and try:
- Upload one month's bank statement as a CSV.
- Correct one transaction's category and watch the matching ones update.
- Set a monthly budget for your three biggest spending categories.
- Open Cash and find one recurring bill you could cancel.
- Press Fill from last 3 months, then try a scenario with a new $3,000 monthly cost.
Worked through every option above? Finish the lesson to tick it off.
Want more detail? Read Finance: connecting your money, Finance: overview, cash and reports and Finance: planning, payroll and plans in the manual.