📋 Bootstrap Your Business Workflow

Missed a past post? Searching for something in particular?

Here you can follow the workflow from end to end.

Looking up the center of a spiral staircase. — Photo by Johannes Plenio

🚀 Getting Started

Learn to Bootstrap a New Business (from Scratch!)
Keep your money in your pocket - you don't need to hire an expensive service to start a business.
Let’s Go on a Journey to Build Your Own Business
Post #1: Learn the steps to create your own business from scratch (and with very few startup costs or fees)!

BONUS: Quick Start Your Business!

12-Steps to Make Your Portfolio Business a Real Business (LLC or S-Corp)
Post #45: Don't just report your income on your 1040 (USA).

⭐ Branding: Naming Your Business

Picking a Great Name for Your New Business
Post #2: Take these steps to ensure that your new business name has not yet been claimed.
Performing a General Web Search Before Deciding on a Name for Your Business
Post #3: Be sure that you don’t choose a name that has already been used (avoid getting into trouble with your new business name).
Checking with the Secretary of State to See if a Business Name has Been Claimed
Post #4: Before you buy a URL, get an email address, or print business cards, check with the SOS to see if your name idea has been claimed.
Searching the USPTO Before you Register a New Business Name
Post #5: the US Patent and Trademark Office is another place to check before selecting a new name for your business.
Searching the DNS for a Domain Before Registering a New Business Name
Post #6: Domain Name Service providers can help you search for an available domain before you commit to registering a new business name.
Check with Google Maps Before Registering a New Business Name
Post #7: Online map apps can help you search for existing businesses that may not have a web presence.
Search on Social Media Platforms Before Registering a New Business Name
Post #8: Unique and catchy social media names and handles can be a critical element to your marketing.
Check with Local Licensing Authorities or Municipal Business Directories Before Choosing a Name for Your Business
Post #9: This overlooked step to verify that your new business name is not already claimed may save you big headaches in the future.
Check International Databases Before Registering a New Business Name
Post #10: If you’re planning to go international, ensure your business name isn’t already claimed in global trademark databases.
Pick a New Business Name That Stands Out and Avoids Confusion
Post #11: Just because the name sounds good to you and no one else claimed it, doesn’t mean you’re good to go.

🏛️ Business Structures

Choosing the Right Business Structure for Your Small Business
Post #12: Learn the difference between Sole Proprietorship, Partnership, LLC, S-Corp, and C-Corp business structuring.
How to Register Your New Business with the Local Secretary of State
Post #13: A quick guide to registering your new Sole Proprietorship, Partnership, LLC, or Corporation with the SOS
How to Register a DBA for Your Small Business
Post #14: a DBA can make it easy to have a memorable customer-facing business name, and save time with reporting and operations.
Get an EIN from the IRS for Your Small Business
Post #15: An Employer Identification Number (EIN) is like a Social Security Number for your business.
When to Convert your Sole Proprietorship Business to an LLC (Limited Liability Company)
Post #16: Limit your liabilities, protect your social security number, and enjoy the benefits of operating a Limited Liability Company.
When to Upgrade Your LLC to an S-Corp (and Why It Matters)
Post #17: Save a ton of money and boost your business credibility by electing for S-Corp status with the IRS.
Why Every Independent Contractor Should Set Up an LLC (and Consider S-Corp Status)
Post #46: For freelancers, gig workers, temporary workers, contractors, sub-contractors, 1099 Workers... that's you!

🎯 Business Planning & Strategy

How to Write a Business Plan: A Guide for Aspiring Solopreneurs and Entrepreneurs
Post #21: Because flying by the seat of your pants is not a very good plan for running your small business.
Business Plan Builder Questionnaire (for Aspiring Business Owners)
Post #22: Top 50 Questions to ask yourself when preparing your Business Plan.
The #1 Reason Small Businesses Fail (and 6 Methods to Avoid This)
Post #43: If you fail to plan, you plan to fail.

🗄️ Business Operations (Setting Up)

Don’t Wait to Establish a Record-keeping System for Your New Business
Post #18: Get organized by centralizing your paperwork, finances, and planning documents (before things get out of control).
Business Bookkeeping for Your New Business (Start a Healthy Habit)
Post #19: Tracking your business finances in a bookkeeping tool is a healthy habit that will pay dividends and lead to long-term success.
Financial Management Tips for Solopreneurs and Entrepreneurs
Post #20: Keep your business and personal finances separate.
Small Business Licensing, Permits, and Regulations: What You Need to Know
Post #23: As an aspiring or new business owner, be sure to get the licenses or permits needed to operate legally in your county or city.
Do You Really Need Business Insurance? Here’s What Every Entrepreneur Should Know
Post #24: Even freelancers and solopreneurs should have business insurance to protect assets and livelihood from financial loss.
more to come…

🍱 Get Organized

How Long Should I Keep Records for My Small Business?
Post #34: When you work for yourself (as a freelancer, solopreneur, or entrepreneur), retaining important documents and records is a must.
Boot the Shoebox: An Easy Method to Save & Store Paper Receipts
Post #35: Save your receipts! Why you should ditch the shoebox - and how to do it.
Digital Storage for Receipts: Easy Ways to Declutter, Get Organized, & Be Ready
Post #36: Freelancers & solopreneurs should save all digital and paper receipts with an easy and fast digital storage solution.
Conquer Document Chaos With This Digital Storage Hierarchy
Post #40: Don't struggle with clutter - get your files organized with this comprehensive hierarchy for storing all of your digital documents.
…more to come…

💵 Accounting, Bookkeeping, & Money

Bill of Sale: 7 Reasons to Create Your Own Receipt (Buying or Selling)
Post #37: If you need a proof of purchase (or sale) for a business-related expense, you can make your own receipt.
Expense Reports & Reimbursement: Pay Yourself Back for Business-Related Expenses
Post #38: As a small business owner or freelancer, your business can pay you back for buying things that are business-related.
Expense Report: Create a Document to Pay Yourself Back for Business Expenses
Post #39: Use this simple document to itemize and reimburse yourself (or your staff) for business expenses paid out-of-pocket.
Invoicing Your Clients and Customers: A Guide for the Self-Employed
Post #41: Eliminate the awkwardness around asking for money by sending invoices and get paid for your work.
Income and Expenses: a Simple Tracking System for Your Small Business
Post #42: You don’t need an accounting degree or expensive software to be effective with managing money for your business.
…more to come…

💰 Paying Yourself (Comp & Benefits)

Entrepreneurs: Don't Forget to Pay Yourself (but Not 100%)
Post #51: Reduce your tax bill with a simple payroll calculation.

🏡 Home Office Expenses (Deductions)

Maximizing Your Home Office Deductions: How to Save Money on Taxes
Post #25: There are many advantages to being a business owner - chief among them is deducting expenses as part of your financial strategy.
Calculate Your Home Office Deduction for Mortgage Interest or Rent
Post #26: As a small business owner working from a home-based workspace, deducting your mortgage interest or rent from gross revenues can save on taxes.
Deducting the Cost of Utilities as Part of Your Home Office Deduction
Post #27: Calculate how to deduct a portion of your utility bills (water, heat, cooling, electricity, etc...) from your small business income.
Cut Your Taxes: Internet and Phone Bills Qualify for Home Office Deductions
Post #28: Small business owners who work from home can deduct a portion of internet and cell phone bills from small business gross revenues.
Save Money on Your Taxes By Deducting Homeowners or Renters Insurance
Post #29: Freelancers and small business owners can keep tax bills lower with home office deductions, including the premiums spent on residential insurance.
Deducting Home Repair and Maintenance Expenses from Your Business Income Taxes
Post #30: Did you know that home repairs and maintenance may be eligible for the home office deduction on your self-employed income taxes?
Understanding Depreciation and How to Calculate it for Your Home Office Deductions
Post #31: Depreciation of your home can be a difficult concept that most business owners and freelancers overlook as part of the Home Office Deduction.
Claiming Business Furniture and Equipment as Home Office Expenses
Post #32: When you are self-employed, don't forget to deduct the cost of furniture and equipment that you use in your home-based business.
Property Taxes: a Home Office Expense that You Can Deduct from Your Taxes
Post #33: Freelancers, solopreneurs, and entrepreneurs - if you work from home, you may be able to deduct this home office expense to save on your tax bill.
…more to come…

💲 Business Expenses (Deductions)

[Guest Post] Cybersecurity and Data Privacy Expenses May Be Deductible (to Save on Taxes)
If you are self-employed, your Substack subscription to “Beyond the Firewall” with Jason Rowe may be a tax deductible business expense.
…more to come…

🔐 Protecting Your Business

[Guest Post] I Analyzed 17 Small Businesses (86% Made These Privacy Mistakes)
GP #1: A simple list of don'ts to keep your business and reputation secure.
Tax Scams: Protect Your Business and Yourself from Becoming a Victim
Post #44: Learn about the IRS's "Dirty Dozen" Tax Scams.

📈 Growing & Scaling Up

Handling Growing Pains as a Solo Entrepreneur
Post #50: Set yourself up for sustainable growth and long-term success.