Sole Proprietor Simplified Module 3: Operating a Sole Proprietorship

Step One:


We set up the Sole Proprietorship – now let’s run it!  This is not an accounting class – far from it.  But there are a few basics that we need to cover before going any further.  Anyone who runs a business should be familiar with these terms: 

  • Income – cash that you earn from selling your books and merchandise. 
  • Expenses – cash you spend to produce and promote your books and sole proprietorship. 
  • Capitol – personal or investor money deposited into your business bank account to fund business operations. 
  • Net Income/loss – Income less expenses.  If the number is positive, you have earned a profit that will be taxed at your ordinary income rate.  If the number is negative and you have a loss, you won’t owe any taxes on the income – but your business expenses exceeded your income – not the scenario that we’re working towards! 
  • Taxes – you pay ordinary income taxes on your Net Income.  We’ll discuss taxes further in Module 4. 


Tracking income is important, as you want to know how much money your writing activities earn!  This is all money that is earned from selling your books/merchandise.   


Your business should incur expenses for the necessary and reasonable operation of your business.  Expenses paid for from business income should be for the benefit of the business, not personal expenses.  It is worth the time and hassle to keep them separate.  Eligible expenses include cost of book production (editing, illustration, proofreading), advertising/promotion, legal and accounting fees, software/supplies, business related meals, business related travel and other business related expenses. 

If you don’t capture all income, then you are under reporting income, which leads to not paying all the taxes owed on the income. 

If you don’t capture all the necessary and reasonable business expenses, your income is too high and you’ll pay too much in taxes. 

Step Two:

How do we keep track of all of this information?  Old school methods like keeping track in a spreadsheet Exhibit 3.2 Monthly Income and Expenses.  Or use free, easy to use accounting software like Wave. 

[progressally_vimeo_video id=” vimeo_id=’265887093′ width=’900′ height=’500′ ]Ensure your bank accounts show valid transactions and there is follow up on any outstanding checks.  Ensure the deposits into the account agree to the source reports from Amazon, Itunes, etc. 


In the Author world, a lot of expenses are paid before you receive one dime for the sale of your work – the launch trough.  In order to make sure you have enough cash on hand to cover these expenses, budgeting and planning is extremely important.  Many popular bookseller sites have 60-90 day time lags between selling your book and receiving the cash in your business account.  It’s important to understand when you can expect to have cash available and when you need to spend it.    


See Exhibit 3.3 for a sample planning spreadsheet.  To use this spreadsheet effectively, enter your actual sales by month, and then enter the same amount into the month that it will actually be received.  For example a), earning $100 in sales from Amazon in January will result in a $100 deposit into your business account in March. 


If you are working on book preproduction, enter the month you plan to spend money on editing, cover, etc. so that you know what cash you need – either from the business income or additional investments from your personal accounts. 

For example b), you plan to finish your rough draft in June and will require editing and all of the expenses required to complete a finished product.  Those costs will be $500.  Unfortunately, you only have $100 available from previous sales, so you will need $400 from personal cash sources. 

Yea – the book is done and will launch in mid July.  You’ll need advertising dollars in July to promote your work.  You’ll need $100 from your personal money to fund your advertising. 

Congratulations!  In example c), your book is selling like crazy in July!!  You can expect to receive your July sales of $10,000 in September. 

File Structure:

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Before we move on we are going to create an organization system for your record keeping.  I recommend using a cloud-based storage system like Dropbox, google drive, one drive, AWS S3, or icloud.  The platform does not matter it is what your comfortable using and has the lowest cost to you.  If you are a big google docs user you are likely to go with google drive.  IF you have Office 365 then you get 1TB of cloud storage so you can use it.  The Structure we show you are from Dropbox but you can create this file structure in any of the above.  If you are paranoid about your data then you could do this just on a computer and have some type of back up.  In this day and age using the cloud to give you multi-device access and full data back up just is good business.

File Naming Conventions

A common file name convention is very helpful.  I suggest all files being named year, month, date, then by a naming convention to help you know what the file is.  use underscores for spaces.  This will help you when you need to do a search for a file by narrowing the date range.

File Backbone

This is the backbone structure of your business.  You should create these file folders in your cloud storage of choice.


This folder will be our largest and most active.  With monthly business data, receipts and the like filling up subfolders.

Business Models

Here we will store our annual plans and goals for the business.

Intellectual Property

Here you will file documents for our IP portfolio


This is where we will file legal correspondence.

Marketing Information

This is where we will keep files relating to specific marketing campaigns.

Organization Documents and Information

Here is where we keep the Federal and state documents along with operation agreements.

Product Information

This folder is where we collect information about books, final manuscripts, covers, old copies.


This folder is for collecting data and organizing the other “rivers of cash”.  This is merchandising, collaborations, or anything you need to manage but doesn’t fall into a book or series.

Sales Contracts and Information

Various contracts and agreements

Accounting Branch

The accounting branch holds the majority of your business documents for operations.

Banking Information

How to Organize: Bank and then account

Banking contacts and contracts; monthly statements/reconciliations.

Contractor Info and W9

How to Organize: Individual Contractor

Contract, Non-disclosure agreement, W9, and payment information.

Monthly Reports

How to Organize: Year then the month (2018_01)

Monthly accounting reports and budgets


This has a branch structure of its own see below.


How to Organize: Year then the month (2018_01)

Credit and Debit card receipts.  Scan them in for redundancy.  A note you need to keep your receipts for auditing purposes but you don’t have to be organized to make the auditor’s life easy..  Its fine to just drop them all in one folder.  You don’t get extra points at an audit for being organized but you lose points if you can’t produce the receipt.


How to Organize: Year

Final filed returns and supporting documents

Vendor Files

How to Organize: Individual Vendor

Contracts and invoices by year.


The Payroll branch holds information about benefits, employees and payroll taxes.


How to Organize: Benefit offering (Health, Life, Retirement)

Contract, Roster, Offerings, Correspondence.


How to Organize: Individual Employee

I-9, withholding documents, banking documents, other HR forms.

Payroll Reports

How to Organize: Monthly (2018_01)

Payroll filings and reports

Payroll Taxes by Agency

How to Organize: Agency then Monthly

Registration information then filed returns and support

Sales / Royalties

Save Monthly Pdfs and CSV files of sales reports from the platform.

How to Organize: By platform then by month

Sales files and payment files.

File your records in the appropriate folders.

Now its time to get all of your files up into the cloud.  The first two you should save is your Articles of Organization/ Incorporation in Organization Documents and Information.

Next look at the list and think about what else should be filed here.  Collect up all those documents and put them into the file structure.

For paper documents find a scanner app for your phone that uploads directly to your cloud storage.  You can also use most home printers that have a scanner to get the documents into digital form.

One last thought on planning for the worse

Have a sheet with all of your account login information and what monthly bills need to be paid and from what accounts.

Keep this list somewhere safe but where someone else knows about that can help if something happens to you.  Keep this where you keep items like social security cards and birth certificates.

Many soloprenuer businesses have issues if the owner dies or is incapacitated because their loved ones don’t know where to get into accounts to make payments or transfer funds.

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