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Oh Maple Leaf > Blog > News > Want to know how the rich get richer? Only 3.5% of people know about this financial loophole.
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Want to know how the rich get richer? Only 3.5% of people know about this financial loophole.

Emilio Glover By Emilio Glover Last updated: 22 May 2025 5 Min Read
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In a world where every dollar counts, finding smart ways to stretch your budget can make a huge difference. While many people focus on traditional saving methods—cutting subscriptions, buying in bulk, or avoiding debt—there are also lesser-known financial “loopholes” that can legally and effectively help you keep more money in your pocket. Let’s explore a few of them.

Contents
1. Credit Card Rewards Optimization2. HSAs (Health Savings Accounts) as Investment Tools3. “Backdoor” Roth IRA Contributions4. Buying Discounted Gift Cards5. Using Employer Benefits to Reduce Taxable Income6. “Free Trial Hopping” – Responsibly7. State and Local Tax CreditsFinal Thoughts

1. Credit Card Rewards Optimization

Most people use credit cards for convenience, but few maximize the reward systems attached to them. Strategic use of cashback or travel reward cards—especially when paired with sign-up bonuses—can result in hundreds or even thousands of dollars in value each year.

The loophole: Some cards offer bonus categories (like groceries, dining, or gas) that rotate quarterly. By timing purchases or even buying gift cards in those categories, savvy users can exceed typical reward rates.

2. HSAs (Health Savings Accounts) as Investment Tools

If you have a high-deductible health plan, you may qualify for a Health Savings Account. HSAs are triple tax-advantaged: contributions are tax-deductible, growth is tax-free, and withdrawals for medical expenses are also tax-free.

The loophole: If you can afford to pay out-of-pocket for medical expenses now and let your HSA grow untouched, it becomes a stealth retirement account—useable for medical expenses anytime and even for non-medical use after age 65 (taxed as regular income).

3. “Backdoor” Roth IRA Contributions

High earners often phase out of eligibility for Roth IRA contributions due to income limits. However, a financial workaround exists.

The loophole: You can contribute to a Traditional IRA (which has no income limits for non-deductible contributions) and then convert that to a Roth IRA. This “backdoor” strategy allows continued Roth contributions despite income caps.

4. Buying Discounted Gift Cards

Websites like Raise or CardCash allow users to buy gift cards at a discount—sometimes up to 30% off face value. If you’re planning a big purchase from a specific retailer, this can be a clever way to save instantly.

The loophole: Stack discounted gift cards with store sales, cashback apps, or loyalty points for maximum benefit.

5. Using Employer Benefits to Reduce Taxable Income

Many companies offer flexible spending accounts (FSAs), commuter benefits, or dependent care accounts that can be funded with pre-tax dollars.

The loophole: By contributing to these accounts, you’re not only saving for specific expenses but also reducing your taxable income—essentially getting a discount on things you’d spend money on anyway.

6. “Free Trial Hopping” – Responsibly

Some subscription services offer free trials that don’t auto-renew or are easy to cancel. If used responsibly, hopping from one service to another can provide months of access without paying.

The loophole: Use virtual cards or reminder systems to ensure timely cancellations and avoid accidental charges.

7. State and Local Tax Credits

Depending on where you live, you may be eligible for lesser-known tax credits—like rebates for installing energy-efficient appliances, solar panels, or even working in certain industries (e.g., teaching, agriculture, or public service).

The loophole: These credits often go unclaimed because people simply don’t know they exist. A little local research can go a long way.


Final Thoughts

Financial loopholes aren’t about cutting corners—they’re about understanding the system and using it to your advantage. While these strategies may not apply to everyone, they’re worth exploring if you’re looking to boost your savings without drastically changing your lifestyle.


Disclaimer:
The information in this article is intended for general guidance only. Financial strategies may vary depending on your personal circumstances, location, or updates in legislation. Results may differ, and it is recommended to consult with a licensed financial advisor or tax professional before making major financial decisions.

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