Categories
Taxes

When Veteran Business Owners Should Make an S Corp Election

Many military members and Veterans are venturing into business ownership these days. In fact, 5.5% of business owners in the U.S. were Veterans in 2024. With business ownership comes a host of important and complex decisions. One of which is what entity type to select.

Most businesses start as Limited Liability Companies (LLCs). As the business grows in employee headcount and revenue, it is important to re-assess your entity structure to ensure that it aligns with your personal and business goals. One of those decisions that a successful LLC owner may come up against is the decision to make an S Corporation (or “S Corp”) election.

The goal of this article is to demystify S Corp elections and empower business owners to make informed decisions about the direction of their business.

Why Should You Care About S Corp Elections?

The main reason behind making an S Corporation election is to lower your tax bill. Specifically, we are talking about self-employment taxes. The self employment taxes consist of a 12.4% social security tax up to the first $176,100 in profit in 2025 and a 2.9% Medicare tax on all income. This amounts to a 15.3% tax on the first $176,100 in profit. These profits are also subject to Federal and State tax, so the total tax bill can add up quickly.

Many business owners are confused about exactly when it makes the most sense to elect S Corporation status. Choosing the right time to make this election can save or cost thousands or tens of thousands of income tax.

What Is an S Corp Election?

An S Corp election is a tax status that lets your business profits flow directly to your personal tax return, avoiding double taxation. To be eligible for an S Corporation, you must be U.S. based, have fewer than 100 shareholders, and have a single class of stock.

How this works is you pay yourself a reasonable salary on payroll, and then the excess profit flows to your return to be taxed at Federal and State levels, bypassing any self employment taxes.

For example, if a business owner has a profit of $100,000, the self employment tax on a simple single member LLC will be $15,300. However, if that business owner elects S Corporation status and pays themselves a reasonable salary of $50,000, the self employment taxes will be $7,650, which would save the business owner $7,650 in tax.

Who Should Consider an S Corp Election?

An S Corporation election is going to be most beneficial for small business owners that make a significant profit, usually defined as $50,000 to $100,000 and higher. It is not going to be best for those who have a side gig that may make profit one year and not the next, or for those with more complex ownership structures that require several different classes of stock and might be better suited by a C Corporation.

How to Make an S Corp Election

Here are the steps to file an S Corporation Election:

  1. File IRS Form 2553 by March 15 or within 75 days of forming your business.

 

  1. Set up payroll to pay yourself a reasonable salary. The definition of “reasonable salary” is not well defined by the IRS but should be reasonable if you were to get audited.

 

  1. Update your bookkeeping, tax, and payroll practices. This includes keeping tight bookkeeping in a software like QuickBooks, filing an S Corporation return, and running payroll. This will all increase your administrative costs from a few hundred to few thousand dollars per year.

With these changes, you can expect more administrative burden, cost, and compliance concerns around paying yourself a reasonable salary. The S Corporation structure is certainly more complex than a simple Sole Proprietor, but the payoff can be well worth it in the right situation.

How Will This Benefit Your Business?

The primary benefit of making an S Corporation Election is lower self employment, otherwise known as payroll taxes. As discussed at the top of the article, this happens by lowering the amount of income coming to you in wages which is double taxed by both halves of the 6.2% Social Security tax and 1.45% Medicare tax for a total tax’s of 15.3% on the wage base of $176,100 in 2025. So instead of your entire pay being subject to payroll taxes, only the amount paid to you as a reasonable salary will be taxed at that 15.3% rate. The rest will come to you as an owner’s distribution to be taxed solely at your federal and state income tax rates.

Common Mistakes and How to Avoid Them

Making an S Corporation election is not without risk and mistakes, but with some planning and foresight you should be able to avoid these. The main mistake would be paying yourself an unreasonably low salary, thereby minimizing the percentage of your income that is subject to Social Security and Medicare taxes. If the IRS finds this in an audit and can be extremely costly in penalties.

Another mistake would be choosing S Corp status before your business is consistently profitable. If your business turns extraordinarily little in profit or even loses money, you will not be able to reap the benefits of taking owner’s distributions as your entire profit will go to paying your salary or paying business expenses. This results in you unnecessarily paying hundreds to thousands of dollars in payroll, tax preparation, and compliance costs.

Avoiding these mistakes is completely attainable. Here are three simple steps you can take:

  1. Consult a financial advisor and/or trusted tax preparer.
  2. Use professional payroll software to handle compliance.
  3. Get a reasonable compensation study completed.

Conclusion

Making an S Corporation election can be extremely beneficial for military and veteran business owners. The main benefit is saving on payroll taxes by paying yourself a reasonable salary and then taking the rest as an owner’s distribution. You have to be careful to set a reasonable salary, setup a proper payroll system, and hire a tax preparer to file your S Corporation business return.

Ready to explore whether an S Corp election is right for you? Contact a trusted Military Financial Advisor’s Association member to map out a tax-saving plan that fits your business and personal goals.

 

Categories
Financial Planning

Quantifying the Benefits of Military Credit Card Rewards Hacking

Quantifying the Benefits of Military Credit Card Rewards Hacking

Military members and their spouses have amazing advantages in many aspects of personal finance. One of these areas where I believe they have an outsized advantage is with travel hacking annual fee waived credit cards. There are many varying degrees to which you can attack this and I am by no means an expert on this, in fact I’d defer to Spencer at the Military Money Manual for the ultimate guide, but I wanted to try to quantify the benefits of doing this and show how you can achieve outsize benefits with little effort and how this can pay huge dividends over time.

Laying the Landscape

There are two major companies that give annual fee waived cards to military members. These are American Express and Chase. Every single personal card is free of fees for military members and their spouses thanks to the Military Lending Act (MLA).

There are two main cards that are usually recommended to start with, being the American Express Platinum and the Chase Sapphire Reserve. These are the two premium travel cards that reap the most benefits. Each of these companies has a couple of premium credit cards being the Chase Sapphire Reserve, and the American Express Platinum. After that, there are several other cards that are co-branded with hotels and airlines. Typically, a signup bonus for one of these cards will be somewhere between 50,000 to 100,000 points after spending somewhere between $3,000 and $6,000 in the first 3 months with the card.

There are not many downsides to opening credit cards like this as long as you pay the bill in full every month and be sure that you are not being charged any of the annual fees. Many members worry about the hit on their credit score for opening several credit cards, but Spencer from Military Money Manual does a good job dispelling this myth here. Most military members are going to open at least the American Express Platinum card and then at least one or two more.

The Benefits and Value

To try to quantify the benefits of basic credit card strategies, I want to assume a certain level of spend and a certain amount of cards being opened. If we assume you open three of the top cards, just the American Express Platinum, American Express Gold, and the Chase Sapphire Reserve, you can have all you need to implement a killer strategy to maximize your points.

There are 2 main ways to earn points. Opening a new card and hitting the signup spend amount, and then optimizing your spending in different categories. If you keep going and hit the limit of 5 American Express cards per person or 5 Chase cards in 24 months, or if you don’t want to open up a bunch of cards you really need to focus on optimizing your spend.

The main spending categories that pay really well are:

  • Travel: 10x on Hotels and Rental cars on the Chase Sapphire Reserve, 5x on everything with the American Express Platinum
  • Dining Out: 4x with the American Express Gold
  • Groceries: 6x up to $6,000 with the American Express Blue Cash and 4x with the American Express Gold

Focusing only on a basic spending of $25,000 per year on groceries and dining out on your Amex Gold, you are accruing 100,000 points in a year. These points can be worth up to 2 cents per point according to The Points Guy. That’s $2,000 in travel when transferred to a transfer partner like Delta. Assuming you do that and open up maybe one or two cards per year between 2 spouses to get 100,000 more points, plus any spending you do with the travel branded cards, it’s very conceivable to accrue 150,000 points in one year. This is $3,000 in travel that you don’t have to pay for. Thefuture value of this money is quite astonishing if you are doing travel hacking in your 20s to travel for free and investing the money instead. See the table and graph below showing the return on investment as well as the estimated return on time to manage this strategy for 10 hours a year.

Graph of growth of $3,000 at 7% interest showing value of credit card rewardsFuture Value of $3,000 at 7% interest assuming 10 hours of workA Framework for Hacking Hacking

There is some really low hanging fruit that all military members can take advantage of. The way I see it, there are 3 tiers of travel hacking, and you can go as far as you want into any of them, it is totally up to you how comfortable you feel opening several cards, and how much time you want to spend managing the strategy.

  • Tier 1: Open the American Express Platinum, American Express Gold, and Chase Sapphire Reserve. Enjoy the benefits on each of these cards and just spend the points when you get them.
  • Tier 2: Open a branded airline or hotel card of a hotel or airline that you use a lot, enjoy the premium status and the signup bonus.
  • Tier 3: Maximize all of your cards in American Express and Chase for Both spouses, then focus on optimizing the spending categories to aggregate points at American Express or Chase, and then look for ways to optimally transfer these to transfer partners for the highest value.

I think that with very little effort, you can open up cards at both American Express and Chase, aggregate all the signup bonuses, and then just use American Express Gold on all dining and groceries and American Express Platinum or Chase Sapphire Reserve on Travel. This will allow you to aggregate your points, and then using a branded airline card of an airline near you, transfer those points to that airline to use as a premium member at maximum value.

The Takeaway

There are a million ways to go about using credit cards to your advantage as a military member. Thee important thing to remember is that you always need to pay your balance in full every month, and these credit cards are to support spending that you are already doing. Getting 10x points back on a purchase that you would not have otherwise made still results in money out of your pocket. Some military members want to open 30+ cards like Spencer from the Military Money Manual, while others that are ardent followers of Dave Ramsey want to cut up their cards and only spend with cash or debit card. Whatever your beliefs are, it is hard to deny that with a little bit of knowledge, structure, and effort, you can reap huge value from a basic credit card travel hacking strategy especially for the young military member that is traveling a lot and has decades of compounding ahead.

Need help with this or other financial decisions.  Find an MFAA advisor who can answer your questions here.

Categories
Insurance

Life Insurance Decisions During Military Transition

Life Insurance Decisions During Military Transition

Introduction 

Life insurance decisions during military transition are some of the most critical decisions. Most military members do not carry enough insurance. The majority have SGLI (Servicemember’s Group Life Insurance) which is $500,000 of term life insurance coverage. This coverage is inexpensive at $31 per month and comes out of your paycheck each month. Most members should have more commercial term insurance from a company like USAA.

In this post, I want to focus on the decision to get a life insurance policy when you separate from or retire from the military. This brings up some complex decisions due to the principles of insurability. Many military members will be applying for disability benefits from the VA (Veterans Affairs) during transition. This process may unearth medical problems that will drive up your term insurance rates, or even make you uninsurable. The decision between Veteran’s Group Life Insurance (VGLI) and a commercial policy is complicated for transitioning members. The goal with insurance is to have enough insurance to cover the financial loss of death. You typically need  more insurance earlier in your life when your risk is greatest. Later on in life, you can afford to carry less insurance as your life outstanding expenses decrease.

First: Determine How Much Life Insurance you need

This is the first step in any insurance discussion. The amount of insurance you need throughout your life changes. Here are the steps (for each spouse):

  • Estimate the expenses that would need to be replaced and multiply it by 240 I.e. $5k/month*240 = $1,200,000)
  • Add the mortgage balance or debt you would want to be paid off in the event of death
  • Add the present value of education that you would want to pay for (I.e. You would need to put away $X for your 2 kids to go to college in 10 years)
  • Subtract any investment amount that would be available to use upon death (I.e. TSP)

When you get to the end of this analysis, you will likely realize that you may need 7 figures of life insurance. For military families with a mortgage and kids, $500,000 of SGLI is not enough. You also have to assess how life may change in the coming years with a bigger mortgage or family.

The Military Transition Life Insurance Decision: VGLI Premiums are Very Expensive; Commercial Term Can Make More Sense

When you separate from the military, you have options when it comes to insurance. Here are the main options when you leave:

  • Stop your SGLI payments and don’t get more insurance
  • Convert SGLI to a whole-life insurance product
  • Get a VGLI policy
  • Get a term insurance policy (can also get VGLI) 

Stopping SGLI payments makes sense if you have guaranteed pension income, and don’t see the need for insurance. This might be if you don’t plan to have kids or get married, so very few will be in this camp. If you have determined that you will need life insurance to replace financial loss, then going with no insurance is not a realistic option.

Converting your SGLI policy to a whole-life policy is not a great option either. A whole life insurance product is going to be very expensive, likely 5-15 times the cost of term life insurance per dollar of coverage. It is best to keep insurance and investments separate, and costs low.

VGLI

Getting a VGLI policy is an option as you can get up to $500,000 of term life insurance coverage. You have 1 year and 120 days after separation to apply for VGLI. If you apply in the first 240 days, you don’t have to answer any health questions to qualify. For those who have severe disabilities that make them uninsurable, VGLI could be the only option. This should be the last resort after you have attempted to get a commercial term insurance policy. Click here to find out more about VGLI details.

Commercial Term Insurance

Getting a commercial term insurance policy should be the first option, and VGLI should be the backup. Term insurance is usually level, meaning you have the same premiums for the length of the policy. VGLI rates increase every 5 years of age, so the premiums are very expensive. The below table shows how VGLI rates increase. The graph shows the premiums for 20 years of VGLI coverage versus commercial term policies for a 30-year-old male at the three different health classes of super preferred, preferred, and standard. You can see that even at standard (the worst health class), the cost of a $500,000 policy is far less than that for 20 years of VGLI coverage. This is because VGLI covers a pool of individuals with more health problems (disabled veterans), than commercial insurance policies.

VGLI Premium Schedule (as of the date of this blog publication date)
VGLI Premium Schedule (as of the date of this blog publication date)
Life Insurance Decisions During Military Transition; VGLI vs. Commercial Term Premiums for 30 Yr Old Male
VGLI vs. Commercial Term Premiums for 30 Yr Old Male

Term Insurance is Cheaper the Earlier and Healthier You Get It

Commercial term insurance is cheap in your 20s and 30s, but may become more expensive or unattainable if you have these conditions:

  • Anxiety and depression
  • Asthma
  • Diabetes
  • Heart disease
  • High blood pressure
  • High cholesterol
  • HIV
  • Obesity
  • Cancer
  • Sleep apnea
  • Smoking

Many military members may have these conditions or others and not know it. This fact could come to light during the VA disability exam process. Also, many life insurance applications ask if you have ever filed for disability benefits, which could hurt your health class and your insurance rates if you have to answer yes. The below table shows the benefit of getting classified at a healthier level for a 20-year $1M policy for a 30-year-old male.

Savings of Getting Insurance When In a Healthier Class
Savings of Getting Insurance When In a Healthier Class

You can see that it is well worth it to get classified into a better health category. The “Breakeven” column shows the number of years of savings you would have by getting classified in the lower health class. For example, if I can get classified as super over preferred and I see myself not needing that insurance for another 3 years, I would want to decide to buy insurance as the breakeven is 5.36 years of savings from lower premiums. In other words, I don’t mind paying for 3 years of insurance that I don’t “need” yet due to having a lower mortgage and no kids, because I will save more than that in reduced premiums.

Conclusion

The life insurance decisions during military transition are not  simple. This is due to acronyms (SGLI, VGLI, whole, term, etc.) and insurance agents that want to get paid. It is important to ignore the noise and accurately estimate your insurance need. To summarize, before you go down the road of separation and filing for your VA disability benefits, you should:

  1. Estimate insurance needs (and your insurance needs in 3 years, we want to be generous with this estimate). If you don’t need life insurance and won’t for any foreseeable future because you are financially independent or have a large pension, stop here and go live your life.
  2. Apply for a level term life insurance with a reputable insurance company as soon as you can but before filing for any VA disability claim. 
  3. If you are unable to get a policy, go get $400,000 of VGLI coverage within 240 days of separating.
  4. If you at any point decide you don’t need your term insurance policy for any reason, stop paying the premiums.

The goal of this thinking is to cover the event of a financial loss when the impact is the greatest (early in life) at a reasonable cost. For the majority of transitioning members, the solution to this goal will be applying for a 20-30 year, 7-figure term life insurance policy when you are at your most insurable point in life.

If you need help with insurance or any other financial matter during your transition, reach out to an MFAA advisor that specializes in working with military and veteran families!