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Our 2025 Article Index for Your Business
A topical index to our articles that help your business solve problems.
Good Morning!
Feature: Our 2025 Article Index for Your Business
Dear TCoL: Taxing Employee Holiday Gifts and Bonuses
-TCoL
Missed our last feature article? Cyber Insurance for Your Business
Ten months ago, this newsletter was just getting started. Today it’s read by over 155,000 business owners, founders, and freelancers. That growth happened because you read, shared, and solved problems with us.
To make 2026 even smoother, we’ve organized everything we’ve written for you into a single, problem-solving index.
It is more than a list. It’s a map. Each entry is sorted by the challenges you face most often: finances, legal, hiring, AI, marketing, and more.
Inside you’ll find links, subtitles, and clarity. Because when you’re running a business, the last thing you need is more noise. You need free solutions that get straight to the point. And, of course, no click-bait. Because just like you, we hate click-bait!
We are truly blessed by the support of all of our readers. We wish you Happy Holidays and a wonderful and prosperous New Year!
Note: We will not be publishing the newsletter on Christmas Day, next Thursday, December 25, 2025.

Hiring:
Finances:
Your LLC Is Growing In Other States—Now What About Sales and Income Tax Nexus?
Transferring Highly Appreciated Assets Like Bitcoin and Art to a Sole‑Member LLC
What You Should Expect Before Beginning the Private Equity Process
Get Business Funding in Days, Not Months—But Read This First
LLC Insurance 101: A New Owner’s Guide to Essential Coverage
$100 Blueprint: How Buffett’s 1956 Partnership Still Beats Venture Capital
Understanding LLC Capital Accounts: A Bitcoin Bonanza Explains It All
One Big Beautiful Bill Act’s Impact on Small and Medium Businesses (SMBs) and Their Owners
QuickBooks and Beyond: Exploring Accounting Options for Your SMB
Legal and Governance:
Using Non‑Compete Clauses in LLC Operating Agreements: A 2025 Guide for SMB Owners
How To Assign Your LLC Ownership Interest To Your Revocable Trust
Good News: No More FinCEN Filings for U.S. Businesses—Bad News: Your Data Stays
A Practical Guide to Obtaining, Protecting, and Changing Your LLC Name
How to Involve Others in Your LLC Without Giving Up Ownership
Why Some Entrepreneurs Still Use General Partnerships (Yes, Really)
The Wild West LLC Standoff Between Wyoming and Nevada...And Where Texas and Florida Stand
Before You Sign: A Simple Contract Review and Checklist for SMBs
Template Tuesday: The Initial Resolution You Need After LLC Formation
Template Tuesday: Why You Should Document an Annual Meeting for Your LLC
Need an Attorney for your Business? A Guide to Selecting Carefully
What Businesses Should Consider Using a C Corp Instead of an LLC?
Opening or Moving a Bank Account for an LLC is Not Easy Anymore
Marketing:
Sales:
Strategy:
The Pivot Playbook: How Market‑Driven Shifts Create Market Leaders
Is Building a Politically Neutral Business Still Possible in 2025?
Learning from Warren Buffett: Building A SMB Holding Company
Growth Without a Lease: The Latest Virtual Offices Help Position and Expand Your Business
High-Opportunity States and the Best Small Businesses to Start
Operations:
Utilizing Officer Titles in Your LLC: A Practical Guide for Clarity and Compliance
Networking 101: 12 Groups Every SMB Owner Should Consider Joining
When You Don’t Have The Clout (or Desire) To Order Remote Workers Back To The Office
Pulling Together a Successful (and Fun) Fall Planning Meeting for Your SMB
Growing Quietly with Customers That Keep Coming Back for More
Cybersecurity & AI:
Planning & Productivity
Side Hustles:
Dear TCoL: Taxing Employee Holiday Gifts and Bonuses
Question: I hired my first employee this year. I want to give him a Christmas gift through the business. Is there a way to do that without making it taxable, or should I just give him cash?
Answer: There is no way to give an employee cash through the business that is not taxable, but there are clean options.
The IRS starting point
The IRS generally treats anything you give an employee as taxable wages unless a specific exclusion applies. The main federal reference for employers is IRS Publication 15-B, Employer’s Tax Guide to Fringe Benefits, which is current for 2025.
You can find it here:
https://www.irs.gov/publications/p15b
What is always taxable
Cash is always taxable. That includes checks, payroll bonuses, Venmo, Zelle, and similar payments. Gift cards and gift certificates are treated the same way because the IRS considers them cash equivalents, even if the amount is small and even if you intend them for a particular store or type of purchase. In practice, if it looks and feels like store credit, you should assume it is taxable and run it through payroll.
Calling a payment a gift or a Christmas bonus does not change the tax result; if it is cash or cash-like, it must go through payroll, be reported on the W-2, and have taxes withheld.
What can be non-taxable
The IRS allows certain de minimis fringe benefits, which are small, infrequent, non-cash items where tracking the value for each employee would be impractical. Publication 15-B specifically lists low-value holiday gifts other than cash as an example.
Common examples include a company jacket, a small tool, or a modest holiday food basket. There is no fixed dollar limit in the rules; value and frequency both matter. If the item is meaningful in cost or given regularly, it likely does not qualify, and it starts to look more like regular compensation than a token of appreciation.
Occasional holiday meals or small gatherings for the team are generally treated as de minimis as well, although larger or frequent events can raise different questions. This works well if your goal is a gesture; it does not work if your goal is real financial help.
If you want to give a cash bonus?
Your question did not specify an amount, so consider this as an example. Suppose you decide you want your employee to end up with roughly $500 of extra cash around the holidays. In that case, the clean answer is a cash bonus through payroll.
Many employers choose to “gross up” the bonus so the employee nets about $500 after taxes. That is allowed, but the tax you pay on the employee’s behalf is also taxable wages, so your total cost will be higher than $500, and everything still must be run through payroll and reported correctly.
A practical approach
Many small business owners take a simple two-step approach. They give a modest non-cash holiday gift that is likely non-taxable as a de minimis fringe benefit, and they pay any real financial bonus as cash through payroll, which they treat as ordinary wages.
This approach is straightforward, compliant, and less likely to lead to unpleasant surprises for either you or your employee when tax time comes. It also makes it easier to repeat the practice in future years without having to rethink the structure each time.
Disclaimer: This column provides general information only and is not legal or tax advice. Tax treatment depends on your specific facts and state law, and you should consult your CPA or tax advisor before providing bonuses or fringe benefits.
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