Small Business Tax Savings Podcast

Estimated taxes should not feel like a guessing game, but for many business owners, they do. Underpay, and you face stress, penalties, and a big bill in April. Overpay, and you hand the IRS more cash than needed, limiting what you can reinvest in your business.In this episode, we break down how estimated taxes actually work, why the U.S. tax system is pay-as-you-earn, and how to avoid both overpaying and underpaying. We cover the safe harbor rules, why accurate bookkeeping matters, and how to build a smarter system for quarterly payments that improves cash flow and reduces surprises.👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters(02:15) Why Business Owners Fall Behind on Quarterly TaxesWithout an employer withholding taxes, business owners are responsible for making estimated payments themselves, and many ignore them until penalties and interest build up.(03:45) Why Last Year’s Income Is Not EnoughMany business owners base estimated taxes on last year’s income or send in whatever feels safe, but income, deductions, entity structure, and tax law can all change.(04:30) The Safe Harbor Rules You Need to KnowTo generally avoid underpayment penalties, you need to pay 100% of last year’s tax liability, 110% for certain higher-income earners, or 90% of this year’s tax liability.(06:30) The Cash Flow Cost of Overpaying and UnderpayingOverpaying estimated taxes can tie up money that could be used for marketing, debt reduction, equipment, or other business needs, only to result in a refund later, while underpaying creates pressure when tax time comes, especially if business profits rise and estimated payments were never adjusted upward during the year.(08:40) How to Calculate Estimated Taxes More StrategicallyThe process starts with a quarterly profit analysis, then projecting the rest of the year forward, and finally adjusting payments intentionally based on current numbers.(10:40) Estimated Tax Due Dates Every Business Owner Should Know Quarterly estimated tax payments follow a set schedule throughout the year, and knowing those due dates is essential for staying compliant and avoiding surprises.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

Ed Lyon, a tax attorney who advises business owners on planning and controversies, clears up fears about legal tax strategies. He explains why prosecutions target fraud and poor implementation, where gray areas arise, and what to ask when vetting advanced strategies. Short takes on audit risk, documentation, advisor temperament, and a favored tool for the right client.

Hiring your first employee brings new tax and compliance responsibilities that can quickly become costly. Learn the key differences between W-2 and 1099 classification and why control matters. Discover essential registrations and payroll setup steps you must do before running payroll. Find out why payroll software and timely tax deposits are critical to avoid penalties and keep your business scalable.

They explain why filing a tax extension can buy time to fix messy books and wait for missing K-1s. The conversation clears up myths about audit risk and shows how extensions support intentional tax planning. Penalties for not filing and ways to estimate and pay with an extension are covered. Payment options and solutions when you cannot afford your bill are also discussed.

Changes to charitable giving rules take effect in 2026, including a new deduction for non-itemizers and a 0.5% AGI floor for itemized donations. A cap limits the tax benefit for top earners to 35 percent. New rules for pass-throughs and C corporations change how business giving is treated. Strategies like bunching and qualified charitable distributions are discussed as ways to preserve tax value.

New 2026 tax rule can turn a break-even night at the casino into taxable phantom income. The change caps how much gambling losses you can deduct at 90%. Professional players face stricter limits on deducting expenses and carrying losses. Reporting thresholds shift and careful record keeping becomes essential.

Can you deduct free food, rent your house to your business or avoid double taxation with a C Corp?In this Q&A episode, Mike answers rapid-fire tax questions submitted by business owners across industries. From restaurant deductions to partnership restructuring, foreign contractors, co-mingled expenses, and advanced C Corp investing strategies, this episode walks through what’s legal, what’s smart, and what’s risky. If you want clarity before you file, this is the one to listen to.👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters(01:00) The Augusta Rule: What’s a Reasonable Rental Rate? How to properly rent your home to your business, why documentation matters, and whether to use hotel comps or Airbnb rates.(03:00) Hiring Foreign Contractors: W-8 vs W-9What forms you need on file when paying international contractors and when 1099s apply.(04:30) Partnership Owners: Should You Use an S Corp?How S Corps can reduce self-employment tax, why ownership structure matters, and how to structure it correctly.(09:00) Business Expenses Paid from a Personal AccountCan you still deduct them? What co-mingling means during an audit, and how to fix it going forward.(12:00) Do Insurance Companies Need Your Subcontractor’s Tax Return?Why a signed W-9 is typically all you need and how to protect yourself.(14:00) Can I Deduct Free Food? Restaurant and Bar Tax RulesHow to deduct employee meals and promotional giveaways correctly. Cost vs retail value explained.(17:00) FSA vs HRA: Which One Actually Makes Sense?When high out-of-pocket medical costs justify setting up an HRA and what thresholds to consider.(19:00) $10 Million in a C Corp: Smart Strategy or Tax Trap?The personal holding company rules, double taxation, and when retaining earnings in a C Corp actually makes sense.(22:00) Free Resources for New Business OwnersWhere to start if taxes feel overwhelming and how to build a foundation before filing.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

If you're already giving to charity, you're leaving thousands of dollars in tax deductions on the table. What is a donor-advised fund and why should you care? Mike sits down with Adam Nash, CEO of Daffy, to break down how Donor-Advised Funds (DAFs) work and why they can be a powerful tax strategy for business owners and high-income earners. If you regularly give to your church, your kids’ school, your alma mater, or other charities, this episode shows you how to give more strategically, reduce taxes, and increase your impact.👉 Ready to turn your charitable giving into a real tax strategy? Open a donor-advised fund with Daffy and start giving more strategically today: https://www.daffy.org/taxsavings/invite👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters(00:00) What Is a Donor-Advised Fund?The basics: how DAFs work as a tax-advantaged account for charitable giving, similar to a 401(k) for retirement.(04:45) Tax Deduction Limits: 60% for Cash, 30% for StockHow much you can deduct from your AGI and why bonuses, windfalls, and liquidity events are ideal times to use a DAF.(06:30) Why DAF Donations Are Irrevocable (One-Way Trip)Understanding that donor-advised funds are 501(c)(3) charities and why you cannot take the money back.(09:00) The Double Tax Win of Donating StockHow donating appreciated stock gives you a full market value deduction and eliminates capital gains taxes.(11:30) The New 0.5% AGI Floor and Bunching StrategyHow the recent tax law created a deduction floor and why bunching multiple years of giving into one high-income year makes sense.(15:00) How to Actually Use a DAF Day-to-DayThe mechanics of contributing, distributing to multiple charities, and setting up recurring donations.(20:45) Setting Up a DAF in Under 60 SecondsThe simple setup process, Daffy's flat monthly fee structure, and how it compares to percentage-based pricing models.(28:30) Investment Options and Portfolio ControlHow donated funds are invested tax-free and what level of control donors have over portfolios.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

When should you pay yourself? Paying yourself on the wrong payroll schedule can create IRS red flags, cash flow crunches, and painful cleanup later.In this episode, we break down monthly, quarterly, and annual payroll for S Corp owners. You’ll learn what the IRS actually expects, how reasonable salary works, why quarterly “true-ups” can create cash flow problems, and how to structure payroll to stay compliant without overpaying in taxes.We also cover catch-ups, slowdowns, bonuses, zero payroll returns, and a critical but often-missed strategy involving self-employed health insurance and HSA contributions that can reduce FICA taxes.If you’re an S Corp owner trying to pay yourself the right way and avoid IRS attention, this episode walks you through exactly how to do it. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters(01:00) The Reasonable Salary Requirement for S Corps Why S Corp owners must take W-2 payroll and why determining reasonable salary is the first step.(03:10) Payroll Software and Filing RequirementsWhy using payroll software matters and how missed filings create serious problems.(04:00) Monthly and Biweekly Payroll ExplainedHow spreading your salary evenly works and why this is the most common recommendation.(05:30) True-Up Payroll. Quarterly and Annual Options & Cash Flow RisksHow quarterly and annual true-ups work and how draws get reclassified as wages. Large quarterly tax payments can create cash crunches.(08:45) Zero Payroll Returns and Compliance TrapsWhy you still need to file payroll returns even when no payroll is run.(09:30) Catch-Ups, Slowdowns, and Bonus PayrollsHow to adjust payroll when income, workload, or profitability changes.(11:45) Self-Employed Health Insurance and HSA AdjustmentsHow S Corp owners can increase reasonable salary without paying extra FICA taxes.(15:30) The Safest Payroll Strategy for Most OwnersWhy consistent payroll timing protects cash flow and reduces IRS risk.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

Paying yourself wrong can trigger IRS issues, messy books, and unexpected tax bills. In this episode, we break down exactly how LLC owners should pay themselves in 2026 based on their entity type and tax election.You’ll learn the 3 primary ways business owners get paid: owner draws or distributions, payroll, and guaranteed payments. We explain which payment methods are legally allowed for single-member LLCs, partnerships, and S corporations, and why running payroll as an owner is prohibited unless you have an S corporation election.We walk through how each method is taxed, how it shows up in your financial statements, and why owner draws do not reduce business profit even though they reduce cash. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners:https://www.taxsavingspodcast.com/starterkit🚀 Book your free demo call today. Click here or visit:https://taxelm.com/demo/Chapters(00:45) Why Paying Yourself Correctly MattersImproper owner pay can create audit risk, illegal compensation setups, and accounting problems that surface later during tax season.(01:25) Owner Draws and Distributions ExplainedWhat an owner’s draw actually is, how it works, why no taxes are withheld upfront, and why draws don’t reduce business income.(02:55) Guaranteed Payments for PartnershipsHow guaranteed payments work in partnerships, when they’re used, how they’re taxed, and why they’re different from draws.(04:10) Paying Yourself as a Single-Member LLCWhy single-member LLC owners can only take owner draws, and why running payroll to yourself is not allowed by law.(05:05) Paying Yourself in an LLC PartnershipThe two legal options for partners.(06:00) Paying Yourself as an S Corp OwnerWhy S Corps require a reasonable salary, how payroll and distributions work together, and where tax savings come from.(07:00) How to Document Owner Pay CorrectlyHow draws hit the balance sheet, how payroll hits the income statement, and why documentation matters for audits.(09:30) What to Do Next as an LLC OwnerHow to choose the right pay method, set up a system, plan for taxes, and avoid common compensation mistakes going forward.Podcast Host:Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings PodcastJoin TaxElm: https://taxelm.com🚀 Visit:  https://www.TaxSavingsPodcast.com 🚀 Check Out TaxElm: https://taxelm.com/🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/🚀 YouTube: www.TaxSavingsTV.com👋🏼 GET IN TOUCHYou can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏🙌LEAVE A REVIEWIf you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐🎙 ABOUT THE PODCASTThe Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.