Small Business Tax Savings Podcast

Tax Q&A for Business Owners: S Corps, LLCs, Write-Offs, and More

Every business owner hits a point where the tax questions start stacking up.  Can I deduct this? Should I switch to an S Corp? Is this still a business if I have not made money yet? And what happens if I did something before I had my systems set up the right way? In this episode, Mike opens the floor to questions from business owners and breaks down the tax answers behind them. From zero-activity LLC filings and Schedule C concerns to family payroll planning, vehicle deductions, and rental strategies like the Augusta Rule, this episode covers the practical decisions that shape how much tax you pay and how well your strategy holds up.  👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters (03:22) Do You Need a CPA for a Zero-Activity Partnership Return? A new LLC owner asks about filing a Form 1065 with no business activity. Mike breaks down why even a zero return can be more complex than it looks and what to consider before self-filing. (04:47) Can a First-Year Business Loss Offset W-2 Income? Mike walks through hobby loss concerns, material participation rules, and when a side hustle loss may be used to reduce taxes on other income. (06:35) Is an S Corp Worth It at $120,000 of Profit? This section covers the tradeoff between added payroll and tax prep costs versus potential self-employment tax savings, along with the importance of setting a reasonable salary. (12:01) Where Can You File Business Taxes Online Yourself? For business owners thinking about self-filing, Mike shares general software options and explains why second eyes matter on more complex returns. (13:12) Can You Deduct Business Expenses Paid on a Personal Credit Card? Mike answers a common startup question and explains how to handle valid business expenses paid personally before a business bank account is opened. (14:27) How Does the Family Management Company Strategy Work? This section breaks down how business owners with an S Corp may use a separate sole proprietorship to hire children, reduce payroll taxes, and stay compliant. (20:56) How Does the Augusta Rule Work for Business Owners? Mike explains how the Augusta Rule works, what records you need, and how to back it up in an audit.  Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: https://taxelm.com [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You 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 REVIEW If 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 PODCAST The 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.

2026 Tax Updates Every Business Owner Needs to Know

Every year, the IRS updates important tax numbers, that most business owners miss. This leads to missed deductions, poorly timed income decisions, and unnecessary overpayments to the IRS. In this episode, we break down the most important 2026 tax updates business owners need to know, including changes to tax brackets, standard deductions, Social Security wage caps, retirement limits, HSA contributions, mileage rates, capital gains thresholds, and Section 179 expensing.  👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters (00:52) Why IRS Tax Numbers Change Every Year Tax brackets, standard deductions, retirement limits, Social Security wage caps, HSA limits, and mileage rates are adjusted annually based on inflation and tax policy changes. (01:24) 2026 Standard Deduction and Why It Matters The new standard deduction amounts affect whether it makes sense to itemize and also shape strategies like hiring your children, since income below the standard deduction may avoid federal income tax. (06:12) The 2026 Social Security Wage Cap Wages are subject to Social Security tax only up to the annual wage cap, which makes this number especially important for payroll planning and S Corp salary decisions. (08:15) Retirement Contribution Limits for 2026 Updated IRA and 401(k) contribution limits create new opportunities for tax deductions, especially for business owners using retirement plans to reduce taxable income. (09:43) 2026 HSA Contribution Limits and Why HSAs Are So Powerful HSA contribution limits increased for 2026, and the account remains one of the most tax-advantaged tools available because contributions, growth, and qualified withdrawals all receive favorable tax treatment. (11:13) 2026 Mileage Rate Increases The higher mileage rate can create a larger deduction for business owners who use the standard mileage method, making accurate mileage tracking even more important. (12:57) Capital Gains Tax Thresholds for 2026 Long-term capital gains are taxed under a separate set of thresholds, which makes timing important when selling investments, real estate, or a business. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: https://taxelm.com [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You 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 REVIEW If 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 PODCAST The 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.

Quarterly Estimated Taxes 101 (How to Stop Overpaying or Underpaying)

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 [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters (02:15) Why Business Owners Fall Behind on Quarterly Taxes Without 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 Enough Many 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 Know To 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 Underpaying Overpaying 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 Strategically The 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 Podcast Join TaxElm: https://taxelm.com [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You 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 REVIEW If 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 PODCAST The 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.

Are You Going to Jail for Tax Planning? Tax Attorney Sets the Record Straight

Are you worried a tax strategy could land you in trouble with the IRS?  In this episode, Mike Jesowshek sits down with tax attorney Ed Lyon to break down what tax risk actually means. They explain why most business owners do not get in trouble for smart tax planning, where the line between gray-area strategy and fraud really sits, and why proper implementation matters just as much as the strategy itself.  They cover audit risk, common red flags, what to ask before moving forward with an advanced strategy, and how business owners should think about their own risk tolerance when building a tax plan. 👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters (02:00) Why Business Owners Fear Tax Planning People don't go to jail for legal tax planning. They go to jail for fraud, lying, and backdating documents. (05:00) Why Tax Strategies Exist in the First Place The tax code is designed to encourage certain behavior. Congress uses tax incentives to push homeownership, healthcare benefits, investing, and charitable giving. (12:00) When a Legal Strategy Becomes Illegal A strategy can be perfectly valid in theory, but fail when implemented poorly.  (24:00) How to Vet an Advanced Tax Strategy When someone pitches an advanced strategy, transparency matters. Ed explains what questions to ask, what red flags to look for, and why business owners need to understand who they are dealing with before moving forward. (27:00) How Business Owners Should Think About Risk Tax risk is just another business risk. The real goal is to understand your own risk tolerance, know where your advisor falls on the conservative-to-aggressive spectrum, and make informed decisions. (31:00) A Favorite Strategy for the Right Client Ed closes by sharing one tax strategy he likes for the right candidate, the charitable lead trust, and explains why the best strategy always depends on the client’s goals, income, and long-term plan. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: https://taxelm.com [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You 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 REVIEW If 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 PODCAST The 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.

Hiring Your First Employee? Don’t Make These Expensive Payroll Mistakes

You’ve hired your first employee… Now what?  Hiring your first employee introduces a new layer of tax responsibility, compliance, and systems that many business owners are not prepared for. You are now managing payroll taxes, filings, labor laws, and deadlines that carry real penalties if handled incorrectly. In this episode, we break down exactly what happens after you hire your first employee so you can avoid costly mistakes and set your business up to scale the right way. We cover the difference between W2 employees and 1099 contractors, the real cost of payroll taxes, how to stay compliant with state and federal requirements, and why payroll software is a must.  👉 Get the Free Tax Savings Starter Kit Built for Small Business Owners: https://www.taxsavingspodcast.com/starterkit [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters (01:00) Employee vs Contractor: What the IRS Looks At Classification comes down to control. Who sets hours, pay, tools, and how the work gets done determines W2 vs 1099. (04:00) The Payroll Tax Reality Business Owners Miss Hiring an employee makes you a tax middleman responsible for withholding and paying multiple taxes. (06:00) What You Need Before Running Payroll You need an EIN, state withholding accounts, unemployment accounts, and workers’ compensation set up first. (07:30) Why Payroll Software Is Non-Negotiable Payroll software handles tax calculations, filings, deposits, and compliance to avoid penalties and costly mistakes. (09:30) The Risk of Missing Payroll Tax Deadlines Late payments trigger immediate penalties and interest, and payroll mistakes can shut down businesses. (12:00) Benefits Without Breaking the Bank Health reimbursement arrangements and simple retirement plans offer affordable ways to provide benefits. (14:30) Hiring Employees in Other States Out-of-state hires require additional registrations, tax accounts, and possible foreign entity filings. (16:00) Key Takeaways Hiring is a growth milestone. Set up systems correctly, use payroll software, and build processes that allow your business to run without you. Need payroll software? We recommend https://gusto.com Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join TaxElm: https://taxelm.com [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You 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 REVIEW If 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 PODCAST The 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.