Don’t Leave Money on the Table: 7 Types of ‘Free Money’ Every Smart Investor Should Maximize

Introduction: Unlocking Hidden Wealth Through Smart Financial Moves

When most people think about building wealth, they often focus on increasing income or chasing higher returns on investments. While those are important goals, they sometimes overlook one of the most powerful and underutilized strategies: capturing the “free money” already available to them.

Of course, no money is truly free—there are always conditions or actions required. But many financial tools, employer benefits, and tax incentives offer you a chance to significantly boost your financial well-being with little to no extra cost. These overlooked opportunities can add up to thousands of dollars per year, compounding your long-term wealth if used wisely.

As a financial advisor, I always encourage clients to ensure they’re not leaving money on the table. Here are seven types of “free money” you don’t want to miss—and how to make the most of them.

1. Health Savings Accounts (HSAs): Triple Tax Benefits

Health Savings Accounts are one of the most tax-advantaged financial vehicles available today. With an HSA, you get a triple tax benefit:

• Pre-tax contributions reduce your taxable income
• Tax-free growth on your invested balance
• Tax-free withdrawals for qualified medical expenses

Whether you’re covering a surprise medical bill today or saving for healthcare in retirement, an HSA can help you avoid taxes at every step. In fact, many experts consider HSAs a stealth retirement account due to the long-term compounding potential when you invest the balance.

To qualify, you must be enrolled in a high-deductible health plan (HDHP). If you are, don’t just use your HSA like a regular checking account. Consider paying current medical costs out of pocket, letting your HSA funds grow, and investing the balance for long-term tax-free growth.

Don’t miss: For 2025, the HSA contribution limits are $4,150 for individuals and $8,300 for families, with a $1,000 catch-up contribution for those 55 and older.

2. Flexible Spending Accounts (FSAs): Tax Savings for Health and Childcare

Flexible Spending Accounts allow you to set aside pre-tax dollars for out-of-pocket health or dependent care expenses. While FSAs don’t offer the long-term investing benefits of HSAs, they can still deliver significant tax savings.

For example:

• A healthcare FSA can be used for deductibles, prescriptions, and co-pays.
• A dependent care FSA can cover child care or elder care expenses.

Unlike HSAs, FSAs usually come with a “use it or lose it” rule, meaning unused funds at the end of the year might be forfeited (though some plans allow small carryovers or a grace period).

Pro tip: You can’t contribute to both an HSA and a healthcare FSA in the same year, but you can use an HSA and a dependent care FSA simultaneously—doubling your tax-saving opportunities.

3. 401(k) Employer Match: Free Money for Your Retirement

Perhaps the most overlooked source of free money is the 401(k) employer match. When your employer matches a portion of your contributions, it’s effectively a guaranteed return on your investment. But it’s shocking how many employees don’t contribute enough to get the full match—or don’t participate at all.

Let’s break down an example:
If your employer matches 100% of your contributions up to 3% of your salary, and 50% up to the next 2%, you must contribute at least 5% of your salary to get the full match. That’s money you’re already earning, and choosing not to contribute enough is like turning down part of your paycheck.

Rule of thumb: Fidelity recommends saving 15% of your income toward retirement, including employer contributions. But at a minimum, you should contribute enough to capture every dollar of the match.

4. Employee Stock Purchase Plans (ESPPs): Discounted Stock = Built-In Profit

Employee Stock Purchase Plans allow workers to buy company stock—usually at a discount of up to 15%. Some ESPPs also include a lookback provision, allowing you to buy shares at the lower of the price at the start or end of the purchase period, giving you a built-in gain.

In some cases, there may even be a matching component, where your company gives you additional shares or dollars for participating.

This is a valuable opportunity—but it requires careful planning. Holding too much of your employer’s stock can increase your risk, so many financial planners recommend selling shares periodically and diversifying the proceeds.

Key takeaway: ESPPs can be a low-risk way to boost your compensation—especially if you sell shortly after the purchase period ends. Just make sure to understand any tax implications and avoid overexposure to a single stock.

5. Tax Credits: Direct Reductions in What You Owe

Tax credits are another source of overlooked “free money.” Unlike deductions, which reduce your taxable income, credits reduce your tax bill dollar-for-dollar—making them more powerful in many cases.

Some of the most valuable tax credits include:

• Child Tax Credit
• Child and Dependent Care Credit
• American Opportunity Tax Credit (for college costs)
• Saver’s Credit (for low- to moderate-income retirement savers)

Many households miss out on these credits simply because they don’t know they qualify—especially after life changes like having a baby, changing jobs, or seeing a drop in income.

What to do: Re-evaluate your eligibility every tax season. Work with a CPA or use tax software that automatically checks for credits based on your inputs. Small changes in your income or status can unlock large benefits.

6. Other Workplace Benefits: Reimbursements, Discounts, and More

Many employers offer valuable—but underused—benefits beyond retirement and health insurance. These can include:

• Commuter benefits (pre-tax transportation costs)
• Tuition reimbursement
• Fitness or wellness reimbursements
• Student loan repayment assistance
• Legal or identity protection services

Often, employees are unaware of these programs, or they forget to revisit them during annual benefits enrollment. Employers may update benefits without much fanfare, so it’s worth reviewing your total package regularly.

Pro tip: Don’t wait for open enrollment to do your homework. Check your HR portal or benefits guide now. Even a $50 monthly reimbursement adds up to $600 per year—money you may be leaving on the table.

7. Rewards Credit Cards: Turn Spending into Perks—Carefully

Used responsibly, rewards credit cards are another great source of “free” value. Whether you’re earning cash back, travel points, or retail perks, choosing the right card can turn everyday purchases into hundreds of dollars in annual rewards.

To fully benefit:

• Match the card’s bonus categories (e.g., groceries, gas, dining) to your spending habits.
• Pay your balance in full every month to avoid interest charges.
• Look out for sign-up bonuses that offer significant rewards for meeting early spending thresholds.

Caution: Interest charges, annual fees, or overspending can easily cancel out your rewards. Use credit cards as tools, not temptations.

Final Thoughts: Small Steps, Big Impact

Building wealth isn’t just about earning more—it’s also about being financially efficient. By leveraging these seven forms of “free money,” you can unlock meaningful savings, boost your retirement, and keep more of what you earn.

As a financial advisor, I’ve seen firsthand how these simple strategies can significantly impact long-term financial security. Start by evaluating which of these apply to your situation today, and create a plan to take full advantage. In a world where every dollar counts, smart financial decisions make all the difference.