Return on Hassle

Return on Hassle

Today's Newsletter:

• My Latest

• Is the Juice Worth the Squeeze?

• Return on Hassle

• A Money Question

My Latest

This week, I'm giving you a behind the scenes look at MLB free agency.

In it, I will show you:

• What it looks like to plan for a $100M contract

• The things that most athletes miss in this process

• How these monster free agent deals actually come together

You can check it out here ⬇️⬇️⬇️

Is the Juice Worth the Squeeze

Years ago, after I had officially “retired” from professional baseball, I got invited to play in an athlete networking golf tournament.

It was a nice event.

• Beautiful course

• Good group of people

• Potential business opportunities

But there was a catch: it was across the country, and I’d need to fly in, be gone for three days, and spend time away from my wife and kids, who were juggling school, sports, and life back home.

I wrestled with it for a few days. Logically, I could make the trip.

But was it worth it?

It was a classic Return on Hassle situation.

Would I possibly meet someone? Sure.

But I’d be flying 6 hours, missing family time, and disrupting our routine ~ all for a maybe.

That’s the moment it really clicked for me: Just because something might offer a benefit, doesn’t mean it's worth the cost ~ especially the hidden costs of time, energy, and focus.

Today, I want to talk about how that applies to your money.

Let’s dive in…

Return on Hassle

"Return on Hassle" is my way of measuring whether a financial decision is actually worth the effort, complexity, or time involved.

We already use this logic in other areas of life:

• You won’t drive 30 minutes out of your way to save 5 cents on gas.

• You won’t spend hours calling airlines to save $12 on a flight.

• So why do we chase complicated tax tricks or "too good to be true" investments when the upside is minimal?

Money moves should move the needle. If the juice isn’t worth the squeeze, don’t squeeze.

Why Return on Hassle Matters in Financial Planning

The people I work with~ athletes and entrepreneurs, are not short on opportunity.

The challenge is sorting out what’s worth it and what’s just noise.

There are only:

• So many hours in the day.

• So many decisions you can make.

• So much brain power to allocate.

Every strategy you chase that isn’t worth it distracts from the ones that are.

Return on hassle is about protecting your time, your attention, and your energy.

Let’s Break It Down With Real Numbers

Let me show you two common examples where people chase the wrong rabbit down the hole:

Example 1: Tax Deductions That Aren’t Worth It

Let’s say you’re a high-income athlete or entrepreneur and someone pitches you on a strategy to write off $1,000 in expenses by jumping through hoops ~ maybe renting part of your home office to your LLC or buying something you don’t need to get a “write off.”

The math:

• You’re in a 37% federal tax bracket.

• A $1,000 deduction saves you $370 in taxes.

• But the effort requires paperwork, tax filings, and ongoing tracking

Return on Hassle?
Low. You’re spending hours and risking thousands to save a few hundred.

Better Alternative:
Focus on things like maxing out a Solo 401(k). In 2025, that could mean contributing up to $70,000, saving you north of $25,000 in federal taxes.

Example 2: Private Investments With Low Liquidity

A client of ours once asked about investing in a real estate syndication project. The expected return was 8% annually, which sounds solid ~ until we looked under the hood:

• The money was locked up for 7 years.

• The structure was complicated.

• The fees were high.

• And the person pitching it? More salesman than operator.

The projected upside? Maybe $80,000 on a $250,000 investment ~ if all went perfectly.

Meanwhile, he was already earning close to 5% on a high-yield cash alternative with no lockup, no complexity, and no late-night calls when the deal went sideways.

Return on Hassle?
Way too low for the illiquidity and stress.

What Is Worth the Hassle?

Here’s a short list of financial planning moves that usually are worth it—even if they take time:

Tax Planning That Impacts Your Lifetime Bill

Think big picture, not just this year.

• Safe Harbor Strategy: Pay 110% of last year’s taxes instead of overpaying quarterly estimates. On $200,000 in expected taxes, that could mean keeping $90,000 longer, earning interest while you wait.

• Residency Planning: Living in a no-income-tax state vs. California could save you 13.3% of your income. On $2M a year? That’s $266,000 annually.

Qualified Accounts

This one’s a layup and still overlooked.

• Solo 401(k): Up to $70,000 in 2025.

• Roth IRA: Up to $7,000 in 2025 with tax-free growth.

• HSA: Triple tax benefit ~ contribution, growth, and use can all be tax-free.

Even a 25-year-old investing $7,000/year in a Roth IRA earning 8% annually could grow that to over $1 million by retirement. That’s worth the effort.

Cash Flow Planning

• Building a system to automate saving, taxes, and personal spending is one of the least exciting, yet most powerful things you can do.

A client I worked with saved 20% more in year one by simply creating a “pay yourself first” structure. It took one afternoon to build.

Return on hassle? High.

What’s Usually Not Worth It

• Pursuing tiny tax deductions that require mental gymnastics.

• Obsessing over your investment portfolio’s last quarter performance.

• Making decisions based solely on what your buddy or coworker is doing.

• Complicated estate planning when you don’t yet have the assets to justify it.

______________________

So here is my takeaway…

Time is your most valuable asset. Don’t trade hours for pennies.

Not all returns are created equal. Look beyond dollars to the effort and risk involved.

Simplify when you can. Automation beats complexity every time.

Focus on needle-movers. Qualified accounts, big tax decisions, and optimized cash flow create lasting value.

Trust your gut. If it feels like a hassle with no clear benefit, it probably is.

Until next time my friends!

____________________

A Money Question

What is your highest ROH move this year?

Seriously, please give it some thought…

One is the one move you made that provided an outside impact on your financial life.

______________________

3 Ways I Can Help You

💰 Schedule an introductory call with Moment. We help athletes, entrepreneurs, and key employees build and protect wealth.

📹 Check out my YouTube channel. A safe place to get smarter with your money.

📷 Interact with me on Instagram. I provide bite-sized daily content to level up your money game.

Moment Private Wealth, LLC is a Registered Investment Advisor, located in the State of Missouri. Moment Private Wealth provides investment advisory and related services for clients nationally. Moment Private Wealth will maintain all applicable registrations and licenses as required by the various states in which Moment Private Wealth conducts business, as applicable. Moment Private Wealth renders individualized responses to persons in a particular state only after complying with all regulatory requirements, or under an applicable state exemption or exclusion. Nothing in this content is intended to be, and you should not consider anything in this content to be, investment, accounting, tax, or legal advice.