Stephen Lee, CPA, CPWA®

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• Should You Elect S-Corp at $150K, $300K, or $500K of 1099 Income? 04.07.2026 13min

  Is an S corporation the right tax strategy for your 1099 physician income? The answer isn't based on gross income alone—it depends on your net profit, reasonable compensation, and whether the tax savings outweigh the added costs and compliance.In this episode, CPA and Certified Private Wealth Advisor Stephen Lee breaks down a practical framework for evaluating an S corp election at three common income levels:$150,000 of net 1099 income – When an S corp may be too early.$300,000 of net income – When it's time to seriously run the numbers.$500,000+ of net income – Why an S corp often becomes a compelling strategy when implemented correctly.Stephen also explains:Why net profit matters more than gross 1099 income.How reasonable compensation impacts S corp tax savings.The hidden costs of payroll, bookkeeping, tax filings, and compliance.Common mistakes physicians make when electing S corp status.Why proactive tax planning is essential before year-end.How clean bookkeeping supports better tax and financial decisions.Whether you work locum tenens, telemedicine, moonlighting, or any other independent contractor role, this episode will help you understand when an S corp may—or may not—make sense for your practice.Helpful Resources:📘 Free CPA's Guide to Locum Tenenshttps://stephenleecpa.com/cpas-guide-to-locum-tenens/📅 Schedule a Discovery Callhttps://stephenleecpa.com/book-appointment/?utm_source=spotify📊 Try Xero Accounting Software (90% off for 6 months—terms apply)https://referrals.xero.com/StephenLeeCPA_SCorpDisclaimer: This episode is for educational purposes only and should not be considered tax, legal, or financial advice. Every physician's situation is unique. Consult a qualified tax professional before making tax or entity decisions.
• First Year as a 1099 Physician? Do These 7 Things Before Tax Time 27.06.2026 16min

  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 1099 physician should take before tax season. You'll learn how to set up a clean financial system, track income and expenses properly, plan for quarterly taxes, evaluate LLC and S corporation options, choose the right retirement plan, and avoid the costly mistakes that catch many physicians off guard.Whether you're working locum tenens, moonlighting, transitioning from W-2 employment, or earning a combination of W-2 and 1099 income, this episode will help you build a stronger foundation for tax and financial success.📘 Download the FREE CPA's Guide to Locum Tenens:https://stephenleecpa.com/cpas-guide-to-locum-tenens/?utm_source=podcast📅 Apply for a Complimentary Discovery Call:https://stephenleecpa.com/book-appointment/?utm_source=podcastStephen Lee CPA specializes in helping 1099 physicians, locum tenens physicians, and high-income medical professionals implement proactive tax planning strategies designed to keep more of what they earn while building long-term wealth.
• The Complete 1099 Physician Tax System: 6 Moves to Stop Guessing and Start Planning 20.06.2026 17min

  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 strategy around bookkeeping, entity structure, quarterly tax payments, retirement planning, deductions, and year-end tax planning. Whether you're a locum tenens physician or earning significant 1099 income, this episode will help you understand how all the pieces fit together so you can make better decisions, avoid costly mistakes, and keep more of what you earn.In this episode:Why random tax tips are not a tax strategyThe foundation of clean bookkeepingHow to evaluate LLC vs. S Corp decisionsBuilding an effective quarterly tax payment systemUsing retirement plans strategicallyCreating an audit-safe deduction processWhy year-end planning is critical for tax savings📘 Free Guide for 1099 Physicians:https://stephenleecpa.com/cpas-guide-to-locum-tenens/📅 Book a Complimentary Discovery Call:https://stephenleecpa.com/book-appointment/If you found this episode helpful, be sure to follow the podcast and share it with other physicians looking to build a smarter tax strategy around their 1099 income.
• 1099 Physicians: How to Put Away $100K+ Tax-Advantaged 13.06.2026 17min

  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 contribute $100,000+ annually into tax-advantaged retirement plans using strategies such as Solo 401(k)s, profit-sharing contributions, and cash balance plans. More importantly, he explains when these strategies make sense—and when they don't.You'll learn:• What people really mean when they say "tax-free" retirement contributions• How Solo 401(k) contribution limits work for high-income physicians• When a cash balance plan may unlock larger deductions• Common mistakes that prevent physicians from maximizing retirement contributions• The ideal profile for physicians considering advanced retirement planning• Why entity structure, payroll, bookkeeping, and cash flow all matterIf you're a 1099 physician looking to reduce taxes, build long-term wealth, and stop relying on basic retirement advice, this episode is for you.📘 Free Guide for 1099 Physicians:https://stephenleecpa.com/cpas-guide-to-locum-tenens/?utm_source=podcast📅 Book a Complimentary Discovery Call:https://stephenleecpa.com/book-appointment/?utm_source=podcast⚠️ Disclaimer: This podcast is for educational purposes only and should not be considered tax, legal, investment, or financial advice. Always consult with qualified professionals regarding your specific situation.
• How One 1099 Physician Saved $42,000 in Taxes (Step-by-Step Breakdown) 07.06.2026 20min

  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.You'll learn how entity structure, a properly designed S-Corp strategy, retirement planning, clean business deductions, and proactive tax planning can work together to potentially save tens of thousands of dollars each year.More importantly, you'll discover why tax savings rarely come from one magic deduction and why the highest-earning physicians benefit most from building a complete tax system rather than chasing tax tricks.In this episode, you'll learn:• How a 1099 physician saved approximately $42,000 in taxes• When an S-Corp may (and may not) make sense• The importance of reasonable compensation for physician owners• How retirement plans can create substantial tax deductions while building wealth• Common business deductions many physicians miss• Why clean bookkeeping is the foundation of effective tax planning• How to create a tax reserve system that eliminates surprise tax bills• The biggest mistake high-income 1099 physicians make with taxesIf you're a physician earning $350,000, $500,000, or more as a 1099 contractor, this episode will help you think about tax planning from a strategic perspective rather than a reactive one.🎁 Free Tax Savings Guide:https://stephenleecpa.com/cpas-guide-to-locum-tenens/📅 Book a Complimentary Discovery Call:https://stephenleecpa.com/book-appointment/Disclaimer: This podcast is for educational purposes only and should not be considered tax, legal, financial, or investment advice. Please consult your own qualified advisors regarding your specific situation.
• How 1099 Physicians Should Actually Calculate Quarterly Taxes — Step-by-Step 30.05.2026 22min

  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 projections, how S corporations impact your tax strategy, how retirement contributions affect estimated payments, and the step-by-step framework used to project tax liability throughout the year.Whether you're earning $300,000, $500,000, or over $1 million as a 1099 physician, this episode will help you build a tax system that reduces surprises and creates more control over your finances.Topics Covered:• Why the "just save 30%" rule can be dangerous• The IRS safe harbor rules every physician should know• How to calculate quarterly taxes step by step• Sole proprietor vs. S corporation tax planning• Self-employment tax and payroll tax considerations• Retirement contributions and tax projections• State tax planning for locum and multi-state physicians• Common quarterly tax mistakes physicians make• Building a tax reserve system that works📅 Want help reviewing your quarterly tax strategy, S corporation structure, retirement planning, and overall tax system?Book a complimentary discovery call:https://stephenleecpa.com/book-appointment/🎁 Download our free physician tax planning resources:https://stephenleecpa.com/cpas-guide-to-locum-tenens/If you found this episode helpful, follow the podcast and share it with another 1099 physician who wants to stop reacting at tax time and start planning like a business owner.
• 1099 Physicians_ When an S-Corp Actually Saves You $30K+ (And When It Doesn’t) 23.05.2026 12min

  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 savings are far less impressive than people claim, and why poor implementation can create expensive problems.This episode covers:How S corp tax savings actually workThe difference between salary and distributionsWhat “reasonable compensation” really meansWhen physicians are strong S corp candidatesWhen the numbers usually disappointThe hidden costs of payroll, compliance, bookkeeping, and adminWhy copying another doctor’s structure can backfireThe biggest mistakes physicians make with S corpsIf you're earning strong 1099 income and want to understand whether an S corp truly makes sense for your situation, this episode will help you think through the decision more strategically instead of blindly following internet advice.Book a complimentary discovery call:Stephen Lee CPA Appointment PageThis podcast is for educational purposes only and is not specific tax, legal, or investment advice.
• Stop Doing This With Your 1099 Income (What High-Earning Doctors Get Wrong) 16.05.2026 8min

  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 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. Free, no catch.The CPA's Guide to Being a 1099 Physician https://stephenleecpa.com/cpas-guide-...Book an appointment - https://stephenleecpa.com/the-locum-c...🔔 Subscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.00:00 1099 Money Disappears01:13 Mistake One Paycheck Mindset02:16 Mistake Two Messy Books02:58 Discovery Call Offer03:29 Sponsor Melio Bill Pay05:08 Mistake Three Emotional Payments05:53 Mistake Four Contractor Compliance06:39 Mistake Five More Income Myth07:26 Six Step Reset Plan08:09 Wrap Up Subscribe
• Tax Strategies That Save 1099 Physicians $50,000+ Per Year 09.05.2026 4min

  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. Free, no catch.The CPA's Guide to Being a 1099 Physician https://stephenleecpa.com/cpas-guide-...Book an appointment - https://stephenleecpa.com/the-locum-c...In this episode, I break down why many high-income 1099 physicians earning $350K to $1M+ often overpay the IRS by $30K–$50K+ each year—not from carelessness, but from poor business structure and lack of proactive tax planning. I cover the biggest leaks: missed deductions due to poor tracking and no real-time visibility into profit, and why using clean bookkeeping systems like Xero can help you make decisions during the year instead of at tax time. I also explain how the QBI deduction works for physicians as a specified service business and why controlling taxable income matters, how high earners use retirement plans (Solo 401(k), SEP IRA, cash balance plans) to defer over $100K annually, and why an S-Corp structure can reduce self-employment taxes by splitting salary and distributions. Finally, I emphasize that clean records and documentation are essential to protect deductions and execute any strategy.Subscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.00:00 Stop Overpaying Taxes00:43 1099 Business Mindset01:11 Tracking and Xero Setup02:16 QBI Deduction Strategy02:47 Retirement Tax Shields03:13 S Corp Savings03:47 Clean Books and Wrap Up
• You Filed Your Taxes. Now What? (10 Moves to Make Immediately) 18.04.2026 4min

  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 documents, adjust your W-4 if your refund or balance due was large, update quarterly estimated taxes if you have 1099 or self-employment income, set up an IRS online account to view transcripts and notices, respond immediately to IRS letters, plan proactively for next year’s strategy, organize and digitize records for at least three years, meet with a tax professional—especially if you earn over $200,000 or own a business—and update addresses, banking, and direct deposit information to prevent delays.Subscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.00:00 After Filing Matters00:46 Track Your Refund01:12 Review Return Details01:36 Fix Your W-401:52 Adjust Estimated Taxes02:12 Set Up IRS Account02:33 Handle IRS Notices02:51 Plan Next Year Now03:06 Organize and Digitize03:17 Meet a Tax Pro03:34 Update Your Info03:51 Bottom Line Wrap-Up
• STOP OVERPAYING TAXES 11.04.2026 6min

  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 failing to deduct ordinary and necessary expenses, the home office deduction, mileage and travel tracking, not using retirement plans like SEP IRAs and solo 401(k)s, missing the QBI (Section 199A) deduction, improper worker classification, incorrect depreciation (Section 179 and bonus depreciation), ignoring startup and organizational costs, not writing off bad debts, lacking an accountable plan for reimbursements, poor record keeping, overpaying estimated taxes, failing to claim available tax credits, being overly conservative or overly aggressive with deductions, and not working with a tax professional for ongoing planning.Subscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.00:00 Stop Overpaying Taxes00:51 Write Off Business Expenses01:17 Home Office and Mileage01:51 Retirement Plan Tax Savings02:13 QBI Deduction Explained02:32 Payroll and Depreciation03:02 Startup Costs and Bad Debts03:29 Accountable Plans and Records04:00 Estimates Credits and Risk04:47 Work With a Tax Pro05:02 Bottom Line and Wrap Up
• The IRS "Target" on W-2 Employees (New 2026 Audit Triggers) 02.04.2026 4min

  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, large or disproportionate deductions, consistent business losses that can be reclassified as a hobby, improper refundable credit claims (EITC, child, education), large cash transactions or unexplained deposits, and simple issues like math errors, missing forms, and incomplete returns. He also warns about incorrect dependents or filing status, unreported foreign accounts, abusive tax shelters and “Dirty Dozen” scam patterns, and using a “ghost preparer.” The takeaway: prioritize accuracy, consistency, and documentation to stay audit-ready.00:00 IRS Upgrade Warning00:29 Who I Am00:54 Underreported Income01:21 Unusual Deductions01:49 Side Hustle Losses02:07 Credit Claim Triggers02:30 Cash Deposit Scrutiny02:50 Simple Filing Errors03:04 Dependents and Status03:20 Foreign and Shelter Risks03:37 Dirty Dozen Scams03:56 Ghost Preparer Red Flags04:09 Three Key Takeaways04:29 Subscribe and Wrap UpSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• How to Calculate Your Quarterly Estimated Taxes (Without Over Paying or Penalties) 27.03.2026 6min

  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 more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• 1.3 Million Americans About to Lose Their Tax Refunds | Weekly FAQ 24.03.2026 4min

  🚨 $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 could be owed (median $686+)✔️ Hidden credits like the Earned Income Tax Credit (up to $6,935)✔️ What happens if you haven’t filed recent tax returns✔️ Step-by-step how to still claim your refund⚠️ This is one of the most overlooked IRS deadlines — and it could cost you thousands.00:00 Unclaimed Refund Warning00:50 Deadline and Refund Amounts01:19 EITC and Refund Holds02:09 How to File Without Docs02:40 Rental Loss vs Depreciation03:19 Senior Standard Deduction03:45 Car Loan Interest Cutoff04:11 Final Deadline ReminderSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• Watch This Before Filing for an Extension 21.03.2026 6min

  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 15, 2026 may incur interest and late-payment penalties, with the IRS generally expecting at least 90% paid by the deadline. The video walks through estimating tax liability and completing Form 4868 lines for total tax, payments, balance due, and amount paid with the extension. He details three ways to extend: making an electronic extension payment, e-filing Form 4868, or mailing a paper Form 4868 with proof of mailing, plus special rules for taxpayers abroad and disaster relief.00:00 Tax Deadline Stress00:31 Extension Basics01:12 Deadlines and Payment Rule02:06 Estimate What You Owe02:52 Three Ways to Extend04:22 Special Situations05:16 Key Rules and Reminders06:03 Three Takeaways06:39 Wrap Up and SubscribeSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• IRS Cracking Down on Self-Employment Income (Avoid These Mistakes!) 20.03.2026 7min

  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 (including gig apps, online marketplaces, freelancing, content and affiliate income, and payments via apps) and notes that under IRC Section 61 all such income is taxable, including hobby income. He covers five common mistakes: assuming small amounts don’t matter, waiting for a 1099 before reporting, thinking cash/payment apps are invisible, mixing personal and business finances, and guessing expenses without documentation. He recommends tracking income and expenses, separating accounts, keeping receipts and mileage logs, setting aside tax money, and remembering self-employment tax may apply if net income exceeds $400.00:00 IRS Side Hustle Crackdown00:55 What Counts as Income02:00 Why IRS Notices Happen02:55 Mistake 1 Too Small03:24 Mistake 2 No 109904:04 Mistake 3 App Payments04:36 Mistake 4 Mixed Money05:12 Mistake 5 Guessing Deductions05:38 Real Tax Example06:17 Common Tax Myths06:51 Simple Tracking System07:23 Wrap Up and SubscribeSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• These Viral Tax Hacks Are Getting People Audited (2026) 17.03.2026 6min

  IRS Dirty Dozen 2026: Tax Scams That Can Trigger Audits, Penalties, or Criminal ChargesCPA 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 charges. He notes a viewer question that the senior deduction is scheduled to expire after 2028 unless extended. He outlines major scams the IRS is pursuing: IRS impersonation via phishing/texts, new AI voice scams, social media loophole claims, fake self-employment tax credits, Form 2439 abuse involving fake filings tied to bogus investments, overstated withholdings to force refunds, ghost preparers who won’t sign returns, fake charities (often after disasters), IRS account takeover attempts, and offer-in-compromise mills. He advises slowing down, verifying credits/refunds, and using licensed professionals.00:00 Tax Scams Warning01:00 Community Q and A01:22 Dirty Dozen Overview02:08 Impersonation and AI Calls02:53 Social Media Tax Hacks03:20 Fake Credits and Forms04:02 Withholding and Preparers04:43 Charities and Account Takeovers05:14 Debt Relief Mills05:33 Protect Yourself Framework05:56 Final Takeaways and OutroSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• The IRS Early Filing Trap (Why Experts Say Wait Before Filing) 14.03.2026 5min

  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. Typical timelines: e-file with direct deposit is about 21 days or less; e-file with a paper check is about four weeks; mailing a return takes about 4–8 weeks for direct deposit or 4–9 weeks for a check. A sample return accepted January 28 could pay by direct deposit around February 18 or by check around March 29. Delays can come from EITC/CTC verification, return errors, document mismatches, holiday backlogs, and tracking is available via “Where’s My Refund?” using SSN, filing status, and exact refund amount.00:00 Don’t File Too Early00:38 Meet Your CPA Guide01:06 Refund Season Starts01:41 E-File vs Mail Timelines02:30 Refund Calendar Example02:54 Common Refund Delays03:46 Fastest Refund Rules04:19 Track Your Refund Status04:50 Key Takeaways and Wrap-Up05:31 Comment and Subscribe🔔 Subscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• The Standard Deduction Mistake Costing You Thousands on Gold Sales 10.03.2026 6min

  Donating Gold Coins to a DAF, Precious Metals Tax Rates, and the SALT Deduction ExplainedThis 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 to navigate income tax and make informed financial decisions.00:00 Tax Confusion Teaser00:26 Welcome and Disclaimer00:44 Subscribe and Support01:03 Donating Gold to a DAF01:57 Appraisals and Deduction Rules03:25 Precious Metals Tax Rates04:42 SALT Deduction Eligibility05:55 Wrap Up and Q&ASubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.
• IRS Tax Penalties Explained by a CPA 08.03.2026 4min

  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, to help manage these IRS penalty situations.00:00 Late Penalty Shock00:36 Failure to File Basics01:33 Minimums and Business Returns02:29 Failure to Pay Rules03:03 Interest Adds Up03:24 Penalty Relief Options04:01 Key Takeaways and WrapSubscribe for more tips and strategies tailored for business owners and high earning professionals.On this channel, Stephen Lee shares proven strategies to help high earners, business owners, and professionals keep more of what they make, minimize taxes, and build lasting wealth.Whether you’re optimizing your S-Corp, investing smarter, or managing 1099 income, this channel gives you the tools to make confident money moves — backed by real client experience.Subscribe for smart, actionable advice — and take control of your financial future.The information provided on this channel is for general information and entertainment purposes only. It is not intended to serve as legal, financial, or tax advice. You should not act or refrain from acting on the basis of any content included on this channel without seeking appropriate legal, tax, or other professional advice specific to your individual circumstances. The use or reliance on any information contained on this channel is solely at your own risk.