Chris Massey CPA, PLLC

06/24/2025

Imagine starting January 1, 2026 everyone had to start driving on the left side of the road. Imagine what it would take both personally and all stakeholders to be prepared for that change.

This is what happens during years of tax reform. So imagine instead of your car, it's your business that needs to be prepared and work on changing your strategy.

That's why it's so important to engage in tax planning during these pivotal tax reform years, so you can:

➡️ Realign your tax strategy with your overall business strategic objectives

➡️ Make more tax efficient capital decisions

➡️ Understand your opportunities and hedge against risks

2025 Tax Changes Are Coming – Why Planning Ahead Could Save You Thousands June 24, 2025 by Chris Massey Significant changes to tax laws can ripple through every corner of the economy, impacting how individuals and businesses manage their finances and make decisions. In years marked by tax reform, ...

08/23/2023

LLCs are by far the most common legal entity choice for small businesses. However, many don't know how they are taxed!

By default, LLCs are pass-through entities, which means that the business's profits and losses are reported on the owners' personal tax returns. However, LLCs also have the option to change this default treatment through a tax election (aka the “check-the-box election”). No matter what election you make for tax purposes you will still legally be an LLC and no tax election would change that.

More on the basics of LLC taxation at the link below.

Taxation of LLCs August 23, 2023 by Chris Massey Limited Liability Companies (LLCs) have become a popular choice for entrepreneurs and small business owners due to their flexibility and liability protection. One of the key advantages of forming an LLC is the flexibility it offers regarding taxation....

07/18/2023

Too often businesses are viewing tax planning like this:

"I need to spend $XX by the end of the year to save tax."

"I should buy a brand new vehicle to "write off" on my tax returns."

These may be valid at certain times, but in reality these are almost always entirely tax motivated.

There are many issues with this approach but first among them are that it is not at all strategic, it likely puts you and the business in a worse financial position (even after considering the tax savings), and it may have benefitted you more in a different tax year.

True tax advising means that the advisor understands your business model, knows what you're looking to accomplish, and then uses that knowledge to align your tax strategy with your business strategy all while still saving you money where it makes sense.

A common misconception about tax planning is that you need to spend money on deductible items to save on taxes. For instance, some individuals might purchase expensive vehicles or luxury items, thinking they can offset their tax liability by writing off these expenses. However, this approach leads t...

05/17/2023

S Corp owners: Are you maxing out your 401k plan and want to put more into retirement and experience even larger tax savings?

Ask your financial advisor about defined benefit plans.

Defined benefit plans (DBP) aren't for every business. But those who are good candidates can experience huge tax savings and boost their retirement simultaneously.

Here we explore the basics of defined benefit plans, who are good candidates, and the tax advantages of having a a defined benefit plan in an S Corporation.

Implementing and managing defined benefit plans can be complex, requiring professional guidance and expertise. However, when planned and executed correctly DBPs can provide significant tax savings and retirement benefits. Financial advisors, actuaries, and tax consultants can provide the necessary k...

05/10/2023

Stock Options.

They can be overwhelming for an employee getting them for the first time.

One of the most important aspects of stock options is knowing what methods are available for financing the purchase (i.e. exercise) of your stock options and the tax ramifications of each method.

Here we dive into those methods and what each method generally means for your taxes.

Financing stock option exercises can be a complex process with various methods to choose from. Each method has its pros and cons, so it's important to consider your financial situation and goals before making a decision. If you're unsure which option is right for you, it's always a good idea to spea...

02/23/2023

02/21/2023

Passing down a family business can be as rewarding as it is challenging. I have a few clients now that are planning for the transition now, but are doing so late in the process. Many experts say you should be at least 5 years out from a succession plan event. The article below provides some proactive recommendations when considering to pass down a family business so that you aren't rushing the success planning process.

Many owners of small businesses would love to see a family member take over their business. If you have children, grandchildren, nieces, or nephews that you think might be interested in running the business in the future, you can help lay the groundwork for that potential transfer of ownership in se...

02/16/2023

The home office deduction is one of the most common missed deductions I see when reviewing prior year tax returns for new clients who otherwise qualify. There are 2 methods for claiming the home office deduction: the simplified method and the regular method. Learn more about how to qualify below.

If you're one of the many people working from home this year, you may have questions about the home office tax deduction and whether you can qualify for it. Here's a rundown of the rules.

02/10/2023

Real estate investing offers several tax benefits that typically result in tax losses even when the property is generating cash profits.

Real estate investing comes with significant tax benefits. Find out how to identify the top tax strategies for maximum benefit and how to use them to your advantage come tax time.

02/03/2023

S Corporations are often misunderstood by the owners of the business. Read below for 5 things EVERY S Corporation owner should be aware of.

There are few things in the tax world that have as much misunderstanding and misinformation than S Corporations. S Corporations can help small businesses achieve various goals but only if set up and administered correctly with a good understanding of the tax law. Below are 5 things every S Corporati...