Stop Leaving Money on the Table: 3 company perks high income earners overlook.

By Roland McIntyre, CFP®

When that offer letter landed in your inbox, do you remember the surge of adrenaline, the deep breath you took, soaking in the moment?

A new chapter, a higher salary – it felt like a win. And it was! You probably focused on the big numbers: salary, 401(k) match, vacation days. While these are crucial, many high-income professionals, especially those in fast-paced startups or with stock options, are unknowingly leaving substantial money on the table by overlooking three powerful, yet often misunderstood, company perks. At Mountaintop Wealth, we’re here to turn your finances into freedom, and that includes ensuring you’re maximizing every dollar of your hard-earned compensation.

Let’s dive into these often-missed opportunities, with examples tailored for those seeking early retirement or financial independence:

1. The Health Savings Account (HSA): Your Triple-Threat Investment Vehicle

You might think, “I use my HSA for medical bills, I’m good.” But you’re likely only scratching the surface of its incredible potential. The HSA is often called the “triple-tax-advantaged” account, and for good reason:

Tax-Deductible Contributions: Every dollar you contribute, up to the annual limit, is tax-deductible. For 2025, that’s up to $4,300 for individuals and $8,550 for families. Plus, if you’re 55 or older, you can contribute an additional $1,000 as a catch-up contribution. This immediate tax break reduces your taxable income, saving you money from day one.
- Example Brittany, a 38-year-old software engineer at a tech startup, earning $250,000. She contributes the maximum family amount of $8,550 to her HSA. Assuming a combined federal and state marginal tax rate of 35%, her tax deduction alone saves her approximately $2,992.50 in taxes this year. That’s almost $3,000 staying in her pocket, not going to the IRS!
Tax-Free Growth: The money you don’t use for current medical expenses can be invested within your HSA. And here’s the magic: the investment gains grow completely tax-free. You can switch investments, rebalance your portfolio – all without triggering a single tax event.
- Visualize This: David, a 45-year-old marketing executive, has consistently maximized his HSA contributions for 10 years, investing his unused balance. His HSA now holds $75,000, having grown significantly through savvy investments. If this were a taxable brokerage account, he’d be facing capital gains taxes on those gains. But with his HSA, every penny of that growth is tax-free.
Tax-Free Withdrawals for Qualified Medical Expenses: When you withdraw funds for qualified medical expenses, they are entirely tax-free. This includes a wide range of expenses from doctor’s visits and prescriptions to dental care, vision care, and even certain over-the-counter medications.
- Visualize This: Maria, a 50-year-old biotech researcher, plans to retire early at 55. She’s strategically amassed a large HSA balance. In early retirement, she anticipates higher healthcare costs before Medicare kicks in. Her HSA will be a tax-free ATM for these expenses, allowing her to preserve her other retirement assets.
The “Receipt Hack” for Ultra-Flexibility: This is the game-changer for high-income earners aiming for financial independence. If you pay for qualified medical expenses out-of-pocket (i.e., not directly from your HSA), save those receipts. You can then reimburse yourself for these expenses from your HSA at any point in the future, even decades later, without penalty or taxes. This effectively turns your HSA into a supplementary retirement account, as you can let the funds grow tax-free for years, then tap into them as needed by reimbursing yourself for past expenses.
- Example: John, a 40-year-old data analyst, pays for his family’s annual $5,000 deductible out of his savings account, diligently saving all his medical receipts. He continues to maximize his HSA contributions and investments. By the time he’s 60, his HSA balance has grown to $200,000. He can then withdraw up to $100,000 tax-free by submitting his accumulated receipts from the past 20 years, effectively creating a tax-free income stream in retirement.

2. Employee Stock Purchase Plans (ESPPs): The Built-In Gain Machine

Not every company offers an ESPP, and some have eligibility requirements, but if yours does, it’s a golden opportunity. Forget buying company stock on the open market like everyone else. Through an ESPP, you get the special privilege of buying your company’s stock at a discounted rate, typically between 5% and 15% below the market price. This is a built-in gain from the moment you purchase!

Immediate Discount, Immediate Gain: Your contributions are deducted from your after-tax paycheck over an “offering period” (e.g., 3-6 months). At the “purchase date,” your accumulated funds are used to buy shares at the discounted price.
- Visualize This: Elena, a 30-year-old marketing manager at a publicly traded tech company, has an ESPP that offers a 15% discount. If her company’s stock is trading at $100 on the purchase date, she can buy it for $85. That’s a $15 per share gain before the stock even moves. If she buys 100 shares, that’s an immediate $1,500 gain.
Quick Flip or Long-Term Hold: Depending on your company’s plan rules, you often have the flexibility to sell the stock immediately for a quick, guaranteed profit (though this will typically be taxed as ordinary income). Alternatively, holding the stock for over a year (and over two years from the offering date for “qualified dispositions”) can qualify a portion of the gain for more favorable long-term capital gains tax rates, which are typically lower than ordinary income tax rates.
- Example: If Elena sells her 100 shares of stock purchased at $85 for $100 immediately after purchase, she realizes a $1,500 gain. This $1,500 is taxed as ordinary income. However, if she holds the stock for a “qualified disposition” and the stock price continues to rise, say to $110, her initial discount of $15 per share is still taxed as ordinary income, but the additional $10 per share appreciation ($110 – $100) is taxed at the lower long-term capital gains rate. This strategy is critical for optimizing your tax bill, especially for high-income earners.

3. Stock Options (Equity Compensation): Unleashing Your Wealth Potential

This is arguably the most complex, yet potentially the most compelling, perk offered by many startups and established companies, especially for high-income professionals on a path to financial independence. Unlike ESPPs, where you purchase stock at a discount, stock options are a right to purchase shares at a predetermined price (the “strike price” or “exercise price”) in the future.

There are several types of equity compensation, including:

Restricted Stock Units (RSUs): These are promises to give you company shares once certain conditions (like a vesting period) are met. Once vested, the shares are yours, and their fair market value at vesting is typically taxed as ordinary income.
Incentive Stock Options (ISOs): These can offer significant tax advantages, as the “spread” (difference between market price and exercise price) at the time of exercise is generally not subject to ordinary income tax (though it can be subject to Alternative Minimum Tax, or AMT). If you hold the shares for a certain period after exercise, any additional gains can be taxed at lower long-term capital gains rates.
Non-Qualified Stock Options (NQSOs): The “spread” when you exercise NQSOs is taxed as ordinary income, and any further appreciation after exercise is subject to capital gains tax when you sell.

While the specifics of each type and their tax implications are nuanced, the common thread is that equity compensation forms a significant part of your total compensation package. Limitations often include vesting periods (you must work for the company for a certain time), grant periods, and exercise dates (windows during which you can buy the stock).

ISO Example: Consider Alex, a 35-year-old principal engineer at a pre-IPO startup who received a large grant of ISOs. His strike price is $10 per share. After three years, his options vest, and the company is now valued much higher, with the stock trading at $100 per share. If he exercises 1,000 shares, his “paper gain” of $90,000 ($90 x 1,000 shares) is not immediately taxed as ordinary income. He holds these shares for over a year, and when the company goes public, he sells them at $150 per share. The entire gain of $140,000 ($140 x 1,000 shares) from his initial strike price could be eligible for favorable long-term capital gains tax treatment (minus any AMT considerations), accelerating his path to financial independence significantly.
Example (RSUs for Immediate Wealth Building): Sarah, a 42-year-old product manager at a mature, publicly traded company, receives 5,000 RSUs annually, vesting over four years. Each year, as a portion of her RSUs vest, the value of those shares is added to her taxable income. If 1,250 RSUs vest when the stock is at $200 per share, she receives $250,000 in taxable income. While this adds to her current tax burden, it’s also a significant boost to her liquid wealth that she can use to pay down debt, invest further, or save for large purchases, all contributing to her overall financial freedom. For high-income earners, understanding how to manage the tax implications of RSU vesting (e.g., through sell-to-cover or holding strategies) is crucial.

Don’t Let Your Hard Work Go Unrewarded!

These three perks—HSAs, ESPPs, and Stock Options—are not just “nice-to-haves” for high-income professionals. They are powerful tools that, when understood and leveraged correctly, can dramatically accelerate your journey to financial independence and early retirement. The complexity can be daunting, but the potential rewards are immense.

Are you ready to stop hoping for financial independence and start demanding it? At Mountaintop Wealth, we make the complex, clear. We empower high-income earners like you to master your taxes and supercharge your investments.

Don’t leave another dollar behind! Download our exclusive “Mountaintop Wealth Employee Benefits Optimization Checklist” today and discover how you can turn your company perks into true financial freedom.

[Link to your checklist here – MountaintopWealth.com/checklist]

P.S. If your taxes and investments are a constant source of frustration, leaving you feeling more stressed than successful, it’s time for a wake-up call. Let Mountaintop Wealth guide you to clarity and confidence. We don’t just manage money; we turn finances into freedom.

Book your complimentary consultation here.