Stephen Lee, CPA, CPWA®

If this is your first year as a 1099 physician, tax season can feel completely different. No automatic withholding, no employer payroll department, no simple W-2 return, and no clear roadmap for taxes, retirement planning, quarterly payments, or entity structure decisions. In this episode, CPA and Certified Private Wealth Advisor Stephen Lee walks through the 7 essential steps every first-year 109...

Are you a 1099 physician relying on random tax tips like forming an LLC, electing an S Corp, opening a SEP IRA, or saving 30% for taxes? In this episode, CPA and Certified Private Wealth Advisor Stephen Lee breaks down the complete 1099 physician tax system—a six-part framework designed to help independent physicians stop guessing and start planning. You'll learn how to build a coordinated str...

Most 1099 physicians are told the same basic retirement advice: open a SEP IRA, max out a Solo 401(k), and track your deductions. While that's a good start, high-income physicians earning $400,000, $800,000, or more may be missing significantly larger opportunities. In this episode, Stephen Lee, CPA and Certified Private Wealth Advisor, breaks down how some 1099 physicians may be able to contr...

A 1099 physician saved $42,000 in taxes, without buying a luxury SUV, creating questionable write-offs, or using aggressive tax loopholes. In this episode, CPA and Certified Wealth Advisor Stephen Lee breaks down a real-world case study of a physician earning approximately $575,000 as a 1099 contractor and the step-by-step strategy that helped create significant tax savings while staying compliant...

Most 1099 physicians are calculating quarterly taxes the wrong way, and it can lead to penalties, cash flow problems, and massive surprises at tax time. In this episode, CPA and Certified Private Wealth Advisor Stephen Lee breaks down how high-income 1099 physicians should actually calculate quarterly estimated taxes. You'll learn the difference between safe harbor payments and true tax projec...

If you're a 1099 physician wondering whether an S corp can actually save you serious money or if it's just overhyped tax advice, this episode is for you. In this episode, Stephen Lee, CPA and Certified Private Wealth Advisor, breaks down the real S corp conversation for high-income independent physicians. You’ll learn when an S corp can potentially save $30K+ per year in taxes, when the sa...

5 Costly Money Mistakes 1099 Physicians Make (And How to Fix Them) In this episode, I explain why many high-earning 1099 physicians still feel financially stressed—not because they don’t make enough, but because they haven’t built the business systems needed to manage taxes, cash flow, and bookkeeping. Payment workflow made smarter by Melio - https://affiliates.meliopayments.com/... The exact fram...

1099 Physician Tax Strategy: Stop Overpaying the IRS (QBI, Retirement Plans, S-Corp) Special Xero offer: Get 90% off for 6 months using this link - https://referrals.xero.com/StephenLee... Terms & Conditions apply.* The exact framework I walk through with new clients and how to structure your entity, what to track, which retirement accounts to use, and how to stop leaving money on the table. F...

10 Things to Do After Filing Your Taxes (Avoid Penalties & Keep More Money) CPA and certified private wealth advisor Stephen Lee explains that filing taxes is only the starting point and outlines 10 actions to take after filing to avoid penalties and optimize next year’s taxes: track your refund using the IRS “Where’s My Refund” tool, review your return for errors and save all supporting docum...

Common Tax Mistakes That Make Business Owners Overpay (And How to Fix Them) Special Xero offer: Get 90% off for 6 months using this link - https://referrals.xero.com/StephenLee... Terms & Conditions apply.* CPA Stephen Lee explains that many business owners legally overpay taxes by missing strategies allowed by the tax code, then walks through 15 common issues and how to fix them. He covers fa...

IRS Upgrade: Top Audit Triggers for W‑2 Employees (and How to Avoid Them Legally) CPA Stephen Lee explains that the IRS has upgraded its systems to flag common W‑2 return mistakes and outlines key triggers for manual review, especially for employees with side hustles, crypto activity, or home office claims. Major red flags include underreporting income that doesn’t match W‑2/1099/brokerage data, l...

Most people think taxes are something you deal with once a year in April, but business owners, freelancers, and investors need to pay taxes four times per year. This video explains how to calculate and pay your quarterly estimated taxes, including using IRS Direct Pay. Learn how to avoid tax penalties by understanding your estimated taxes and ensuring you meet your obligations. 🔔 Subscribe for mo...

🚨 $1.2 BILLION in Unclaimed IRS Refunds — Don’t Miss the April 15 Deadline 🚨 Over 1.3 million Americans still haven’t filed their 2022 tax returns — and the IRS is holding $1.2 BILLION in unclaimed refunds. If you don’t act by April 15, 2026, your refund becomes property of the U.S. Treasury… permanently. In this video, I break down: ✔️ Who is at risk of losing their refund ✔️ How much money you...

How to File a Tax Extension for Form 1040 (2026 Deadlines + 3 Easy Methods) CPA Stephen Lee explains how to request an automatic six-month tax extension for a Form 1040 using IRS Form 4868 for the 2026 tax season, covering key deadlines and common mistakes that can trigger IRS penalties. He emphasizes that an extension gives more time to file—not more time to pay—and that unpaid taxes after April...

Side Hustle Taxes: 5 Mistakes That Trigger IRS Notices (and How to Avoid Them) CPA Stephen Lee explains why the IRS is paying closer attention to side hustle (self employment) and gig income as platforms and clients send 1099 forms that are automatically matched to tax returns, with mismatches triggering notices like CP2000. He defines side hustle income as any earnings outside a W-2 job (includin...

IRS Dirty Dozen 2026: Tax Scams That Can Trigger Audits, Penalties, or Criminal Charges CPA Stephen Lee explains the IRS “Dirty Dozen” for 2026 as an enforcement roadmap targeting a surge in fabricated tax claims (fake credits, withholding, and capital gains reporting) and warns business owners, investors, and high earners to avoid online “tax hacks” that can lead to audits, penalties, or criminal...

2026 IRS Refund Calendar: How Long Your Tax Refund Takes (Fastest Way to Get Paid) Stephen Lee, a CPA and certified private wealth advisor, explains why filing taxes too early—before all tax documents arrive—can delay refunds, then walks through the 2026 IRS refund calendar and what determines refund timing. The 2026 filing season began January 26, and most refunds start going out in mid-February....

Donating Gold Coins to a DAF, Precious Metals Tax Rates, and the SALT Deduction Explained This video addresses common tax confusions, specifically concerning physical gold donations, capital gains on precious metals, and self-deduction eligibility for married couples. We're clearing up these complex topics to prevent costly mistakes and provide effective tax planning. Learn practical tax tips...

Stephen Lee CPA explains the significant 2026 minimum late-filing penalties from the IRS, which can quietly add thousands in penalties even without fraud or audit. We'll cover the potential costs for individuals and partnerships, emphasizing the importance of timely tax filing to avoid these issues. Learn about available tax relief options, including reasonable cause and first-time abatement,...

Avoid the USPS Postmark Trap: How to Prove Your Tax Return Was Filed On Time CPA Stephen Lee explains the “USPS postmark trap” that can make a tax return mailed on April 15 (or March 15) appear late if the postmark is dated after the deadline due to processing delays at regional facilities. Because the IRS system relies on the postmark date, a late postmark can trigger failure-to-file and failure-...

#IRS red flags #Can IRS see your bank account #IRS audit explained #Business losses IRS rules IRS FAQ: Business Losses, Declining Income, Bank Accounts, TOD Deeds & Deduction Rules Stephen Lee CPA answers common taxpayer questions: how the IRS treats multi-year business losses after COVID, explaining net operating losses (NOLs) can generally be carried forward indefinitely to offset up to 80%...

Why High Earners File Tax Extensions (And How It Can Save You Money) CPA and certified private wealth advisor Stephen Lee explains why many wealthy taxpayers strategically file tax extensions, emphasizing that an extension extends time to file—not time to pay. He outlines 2026 filing deadlines and forms (individual Form 4868 for April 15 to October 15; S corps/partnerships Form 7004 for March 15 t...

Most retirees have no idea how powerful the IRS home tax rules can be. In this video, Stephen Lee, CPA and Certified Private Wealth Advisor, breaks down four major tax strategies that could significantly reduce taxes in retirement. We cover the Section 121 home sale exclusion that allows up to $500,000 of tax-free profit, medical expense deductions for aging in place, the real tax treatment of rev...

The $300 Gambling Trap + The New $40,000 SALT Cap (Most People Are Getting This Wrong) Stephen Lee, CPA and certified private wealth advisor, explains how small tax reporting mistakes can trigger IRS issues, focusing on gambling income reporting and the new 2025 $40,000 SALT cap for single filers. He answers whether a $300 sports bet payout should be reported as $300 or $200, clarifying that casua...

8 IRS Audit Red Flags for 2026 And How to Reduce Your Audit Risk Legally CPA and certified private wealth advisor Stephen Lee explains that IRS audits are driven by scoring systems that flag tax returns that look statistically unusual for a given income level or industry. He outlines eight audit red flags for the 2026 filing season: lifestyle spending that doesn’t match reported income; aggressive...