How to Pay Less on Your 2025 Taxes

• Filing Yourself

• High Earning W2

• Solopreneur

• Digital Nomad

• Startup Founder

• Key Tax Season Deadlines

• Quick Vendor Reference

Filing Yourself

You’re a W2 employee, a freelancer, or somewhere in between. Your situation isn’t ultra-complex, and you’d rather handle it yourself than pay for a CPA. Here’s what to focus on:

1. If you changed jobs in 2025, check your 401(k) contributions. Each employer withholds toward the $23,500 annual limit independently. If your combined contributions exceeded the cap, you need to request a return of excess from one of the plans before April 15.

2. If you have self-employment income, count every legitimate business deduction. Home office, equipment, software, professional development, business travel, health insurance premiums. These all reduce your Schedule C income, which reduces both your income tax and your self-employment tax. Every dollar of deduction saves you more than a dollar in taxes when you’re self-employed.

3. Know your cost basis on any stock you sold. If you sold RSU shares in 2025, your cost basis is the fair market value on the day they vested, not zero and not what you paid. Many brokerage 1099-Bs report $0 basis by default, which causes people to massively overpay capital gains tax. Your equity platform should have the correct basis history. Make sure your return reflects it.

4. Don’t overlook the easy above-the-line deductions. Student loan interest (up to $2,500), HSA contributions, and if you’re self-employed on the side, half your self-employment tax are all deductible regardless of whether you itemize. These reduce your adjusted gross income, which can have downstream effects on other phase-outs.

Prime Meridian is the tax prep service I’d use in this situation. It’s completely free for federal and state returns, handles W-2s, RSU cost basis, 1099-Bs, and multi-state returns, and takes about 15 minutes. Their AI agent will look for every deduction you qualify for and I’ve been genuinely impressed by the accuracy. Their average customer saves $540 on CPA fees, so consider filing with Prime Meridian for free this year!

High Earning W2

You work at a tech company or larger corporation. Maybe you’re an IC, maybe you’re a director or VP. You have a salary, RSUs or stock options, and the decisions you make around equity timing are worth real money. Your taxes aren’t simple, and the generic advice doesn’t quite fit:

1. Check your RSU withholding gap. When RSUs vest, your employer withholds taxes, but many default to a flat 22% supplemental rate. If you’re in the 32% or 35% bracket, you’ve been under-withheld all year and could owe a meaningful amount at filing. Go back through your vest dates and do the math. If there’s a gap, consider making an estimated payment before April 15 to avoid underpayment penalties.

2. ISO exercises may have triggered AMT and you might not know it. If you exercised Incentive Stock Options in 2025, the spread between your strike price and the fair market value (FMV) at exercise is an Alternative Minimum Tax (AMT) preference item, meaning it doesn’t show up in your regular taxable income, but it does for AMT purposes. Depending on how large the spread was, you could owe tens of thousands of dollars in AMT even with no regular income tax change. Don’t skip this calculation.

3. Qualifying dispositions vs. disqualifying dispositions matter for ISOs. To get long-term capital gains treatment on ISO shares, you need to have held the shares for at least two years from the grant date AND one year from exercise. Selling before either threshold is a disqualifying disposition and the gain gets taxed as ordinary income, potentially at 37%. If you sold ISO shares in 2025, figure out which category they fall into before you file.

4. If it’s an unusually high income year, think about a Donor-Advised Fund. Whether it was a large vest, a liquidity event, or a substantial bonus, a Donor-Advised Fund (DAF) lets you make a large charitable contribution now, claim the deduction in 2025, and distribute the money to charities over time. You can also contribute appreciated stock directly to a DAF and avoid capital gains entirely.

This is exactly the situation where a specialized CPA pays for itself. Fifteenth is the tax service I’d use in this situation. They were built specifically for high earning employees with equity-heavy situations. Their team is ex-Big Four and Carta, trusted by 1,000+ employees at OpenAI, Stripe, Google, and Anthropic, and they offer a personalized flat annual fee that includes year-round access to your own advisor and filing for this tax season.

Solopreneur

Your income comes from 1099s, a business you run, or a mix of a day job and side work. If you’ve been doing this for a few years, you probably already know taxes can get complicated. Here’s what to actually focus on:

1. Self-employment tax is real and most people underestimate it. If you work for yourself, you’re paying both the employer and employee sides of FICA, 15.3% on net self-employment income, on top of regular income tax. On $80,000 of income, that’s over $11,000 in self-employment tax alone. The silver lining is that you can deduct half of it as an above-the-line deduction. And if your net self-employment income is consistently above $100k, it’s worth exploring an S-Corp election to split your income between salary and distributions, thereby reducing what you owe in self-employment tax.

2. If you haven’t been making quarterly estimates, calculate what you owe now. Quarterly estimated taxes were due in April, June, and September of 2025, with a final Q4 payment due January 15, 2026. If you skipped any or underpaid, you may owe a penalty. Calculate the shortfall now and pay it with your April filing. Going forward in 2026, set up quarterly payments. Your future self will thank you!

3. Track every legitimate business deduction. Home office, equipment, software, professional development, business travel, health insurance premiums. These all reduce your Schedule C income, which reduces both your income tax and your self-employment tax. And if you need help keeping track of your deductions, we built reimburse.com to make it a little easier.

4. Look into a Solo 401(k) for next year. You can’t retroactively contribute for 2025 if you didn’t open the account in time, but if you’re generating serious self-employment income, a Solo 401(k) should be on your radar for 2026. You can shelter up to $72,000 per year between employee deferrals and employer contributions. It’s one of the most powerful tax reduction tools available to self-employed people. If you’re looking to get set up, reply to this email and we’ll send you a tax season discount to get started with one of our partners 🙂

Not sure where to start or who to work with? Solopreneur taxes vary a lot depending on how you’re set up. A freelancer filing a Schedule C has very different needs than an S-Corp owner running payroll, contributing to a Solo 401k, and optimizing for QBI. Fill out this short form and my team will personally connect you with a vetted tax expert for your situation.

Digital Nomad

You’ve been living outside the US for part or all of 2025. You still have to file (and we actually just wrote about your situation last week!). Here’s what to stay on top of:

1. You still have to file. The US is one of only two countries in the world that taxes citizens on worldwide income regardless of where they live. If your income exceeded $15,750 (single) or $31,500 (married filing jointly), you’re required to file a federal return. The automatic extension for expats pushes your filing deadline to June 15, but any taxes owed are still due April 15.

2. The Foreign Earned Income Exclusion can wipe out most or all of your federal tax bill. The FEIE lets you exclude up to $130,000 of foreign earned income for 2025 (rising to $132,900 in 2026). To qualify, you need to pass either the Physical Presence Test (330 full days outside the US in a 12-month period) or the Bona Fide Residence Test (established residency in a foreign country for a full calendar year). If you’ve been nomading and counting days carefully, run your numbers because this exclusion is powerful.

3. FBAR is not optional. If you had more than $10,000 in foreign bank accounts at any point during 2025, you must file an FBAR (FinCEN Form 114) by April 15. Willful failure to file carries penalties up to $100,000 or 50% of the account balance (and prison time, yikes). Non-willful failures can still run $10,000+ per violation. So just file it!

4. Self-employment taxes don’t go away with the FEIE. Even if you exclude all your income from federal income tax via the FEIE, you still owe 15.3% in self-employment taxes on net self-employment income. If your country has a totalization agreement with the US and you’re paying into their social security system, you may be able to offset this.

Expat taxes are genuinely complex and the stakes are high. I’ve personally vetted an expat tax specialist firm through my network who understands FEIE vs. Foreign Tax Credit decisions, totalization agreements, FBAR compliance, and multi-country income situations. Request a personal introduction here and my team will connect you directly.

Startup Founder

Your company will file its own return. But your personal 1040 and your company’s tax strategy are more intertwined than you might think.

1. If you have QSBS, verify it now and document everything. Section 1202 Qualified Small Business Stock can let you exclude up to $15 million in capital gains from federal taxes when you sell, completely tax-free. To qualify, your company needed to be a domestic C corp with under $75 million in gross assets at the time of your stock issuance, and you must have acquired the shares at original issuance. If you think you might have QSBS, confirm eligibility now and make sure your company has documentation to back it up. This is worth enormous money at exit.

2. Check whether your company claimed its R&D tax credits. Section 41 R&D credits can offset your company’s income tax liability dollar-for-dollar. Qualifying startups can even apply them against payroll taxes (up to $500,000 per year), which is genuinely meaningful for an early-stage company. Many software companies qualify and never claim this.

3. If you got founders’ shares in 2025 and didn’t file an 83(b), it’s probably too late but learn for next time. An 83(b) election lets you elect to be taxed on the current (typically near-zero) value of unvested shares at grant, rather than the much higher value at vesting. You have exactly 30 days from the grant date. On a successful exit, missing the window can cost hundreds of thousands in unnecessary taxes.

4. Your company has state tax obligations you may not have mapped yet. If you have employees or customers in multiple states, you likely have nexus — meaning filing and tax obligations in those states. This catches founders off guard, especially when headcount grows quickly. It’s worth a nexus analysis if your company has scaled.

For C corps, the firm I recommend is Rivet. They specialize in exactly this: corporate tax prep, R&D credits, state nexus, QSBS planning, and personal 1040s for founders and their exec teams. Their co-founder Kyle spent six years as an IRS auditor specifically auditing tech companies, which means he knows exactly what triggers scrutiny and how to stay clean. Trusted by Cursor, Cognition, and 600+ other startups, Rivet’s a great pick for founders who want a hands-on approach from a team that speaks startup.

Key Tax Season Deadlines

Regardless of which situation above applies to you, these are the dates you need to have on your calendar. Miss one and it could get expensive fast.

One thing worth noting: a tax extension gives you more time to file, not more time to pay. If you owe money and file an extension, interest and penalties on any unpaid balance start accruing from the original due date. Plan accordingly.

Quick Vendor Reference

Reply and let me know: Is there anything your situation throws up that I didn’t cover here? — Ankur

Disclosure: Silly Money has referral relationships with some of the vendors in this guide. We only recommend services we’ve personally vetted. Nothing here is tax, legal, or investment advice.