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The money you're already spending on your family could help lower your business tax bill If your family members perform legitimate work for your business, you may be able to turn some of that spending into tax-deductible wages. In this episode, Mike Jesowshek, CPA, explains how hiring your kids and other family members can help reduce your taxes in 2026. He covers who you can hire, how the rules differ for sole proprietors and S corp owners, and how much your children can potentially earn tax-free. He also walks through reasonable wages, payroll requirements, the documentation you need, and common mistakes that could put your deductions at risk. 👉Find out how much your business could save in taxes: TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ 00:00 How Hiring Your Family Can Help You Save on Taxes  Mike explains how paying family members for real work can turn everyday family support into business deductions. He also shares how one business owner saved $12,000 by hiring his kids. 04:00 How the Tax Savings Work How hiring family members can lower your taxes, including the 2026 standard deduction of $16,100 and potential payroll tax savings. 07:00 Who Can You Hire? Kids, Spouses, and Other Relatives  The rules for hiring children, spouses, parents, and other relatives, and when each option makes financial sense. 13:00 The S Corp Workaround and Family Management Companies  Why S corp owners face different payroll tax rules and how a separate business may help them qualify for additional savings. 17:00 Setting Up Payroll and Documentation Correctly  How to choose appropriate work, pay reasonable wages, and keep the paperwork needed to support your deductions. 22:00 Reporting Family Wages and Calculating Your Tax Savings  How to report wages correctly, handle payroll taxes, and calculate potential savings using real client examples. 26:00 Using a Roth IRA to Build Tax-Free Retirement Savings  How children with earned income can contribute to a Roth IRA and start building retirement savings early. 29:00 Common Mistakes to Avoid and Key Takeaways  The biggest mistakes to avoid, including missing records, unreasonable wages, incorrect payroll reporting, and paying for personal chores. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Stop paying your medical bills with after-tax dollars  You’re already paying for deductibles, prescriptions and co-pays. With the right setup, your business could pay you back for them, tax-free. In this episode, Mike Jesowshek, CPA, explains how a medical expense reimbursement plan (also called an owner HRA or Section 105 plan) can turn out-of-pocket medical costs into business deductions. He covers who qualifies, which entity types work for single and married owners, and the workaround for S corp owners. He also walks through the paperwork you need, how to report the plan on your tax return, and the common mistakes that can cost you the deduction. 👉Find out how much your business could save in taxes: TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ 00:00 Why Your Medical Costs Aren’t Fully Deductible Mike explains who this strategy is for (owners with no employees outside the family) and why high out-of-pocket medical costs often get little or no deduction as itemized deductions, even in a costly year. 03:00 What a Section 105 Plan Is and Who Qualifies How a medical expense reimbursement plan lets your business reimburse an employee for qualified family medical costs, turning after-tax spending into pre-tax business deductions. It also covers the no-employee requirement and how other businesses you own could affect whether you qualify. 06:00 Entity Type, Marital Status, and the S Corp Workaround Why single owners need a C corp and married owners can hire their spouse through a sole proprietorship, partnership, C corp, or rental property. Mike also explains why the plan doesn’t work in an S corp and how moving part of your income into a separate entity can get around that. 09:00 Setting Up the Plan and Reimbursing Expenses The paperwork you need, including a written plan document, employment agreement, job description, and time log. Mike also covers which expenses qualify under IRS Publication 502 and how receipts, a reimbursement log, and payments from the business account support each claim. 13:00 Reporting the Deduction on Your Tax Return Where the deduction goes on a Schedule C, partnership return, C corp return, or Schedule E rental, why these costs no longer belong on Schedule A, and the Form 720 filing that goes with the plan. 16:00 Is It Worth It? A Real Number Example How $50,000 in qualified medical expenses could create more than $17,000 in tax savings. Mike also explains why the plan usually isn’t worth it under $5,000 in costs and when it starts to make sense. 18:00 Mistakes to Avoid and Key Takeaways The most common mistakes, including missing paperwork, a spouse who doesn’t do real work, outside employees, using an S corp, and improper reimbursements. Mike closes with why getting the structure right matters, especially for families with ongoing medical costs. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Your health insurance could do more than cover medical emergencies. With the right strategy, it could also help you save on taxes.  In this episode, Mike Jesowshek, CPA, breaks down health insurance options for small business owners, from group plans to employee reimbursements and stipends. He explains the steps S corp owners need to take to deduct their health insurance premiums and how eligible business owners can use an HSA for tax savings and long-term growth. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ 00:00 | Health Insurance as a Tax Strategy How healthcare planning can help business owners protect themselves, offer employee benefits, and save on taxes. 01:00 | Your Health Insurance Options An overview of group plans, self-funded plans, HRAs, and stipends, plus how your needs differ when you’re self-employed. 03:00 | The HSA’s Triple Tax Advantage A look at tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses. 04:00 | Group Health Insurance Plans How group plans work and how employers decide what portion of employee premiums to cover. 05:00 | Self-Funded and Level-Funded Plans How these plans differ from traditional group insurance, including potential savings and risks. 07:00 | Health Reimbursement Arrangements How HRAs let employers reimburse eligible healthcare costs and why employees need to document their expenses. 08:00 | Stipends and Offering No Coverage The tax tradeoffs of paying employees extra for healthcare and how benefits can help attract and retain talent. 11:00 | Health Insurance for S Corp Owners The payment, W-2 reporting, and personal tax return steps discussed for claiming the health insurance deduction. 15:00 | HSA Eligibility and Contribution Limits An explanation of qualifying health plans and the contribution limits covered in the episode. 17:00 | Investing Your HSA and Saving Receipts Why leaving funds invested may support long-term growth, and how saved medical receipts can support later reimbursements. 19:00 | Review Your Healthcare Strategy Each Year Bring coverage, deductions, employee benefits, and HSA planning together as your business grows. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Documentation 101: How to Prepare for an IRS Audit  You claimed the deduction. But if the IRS asks, can you prove it? Mike Jesowshek, CPA, explains which records you need to support your business expenses. Learn how to document purchases, keep clean books, and organize your receipts so you’re prepared if the IRS comes knocking. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters:  00:00 Your Tax Deductions Need Documentation Paying with a business card doesn’t automatically make a purchase deductible. You need records showing what you bought and why it was business related. 03:00 Audit Selection vs. Audit Outcome Even well-organized businesses can get audited. Good documentation helps you support your deductions if you’re selected. 08:00 The Proof Behind a Business Deduction Every deduction needs an actual transaction, a business purpose, and the correct tax treatment. Your supporting records should match. 12:00 Clean Books and Separate Bank Accounts Separate business and personal accounts, update your books regularly, and clearly label expenses, transfers, and owner activity. 14:00 Business Structure, Payroll, and Reimbursements Your tax filings and records should match your business structure. Payroll, accountable plans, and meeting records need proper implementation. 17:00 What to Record Beyond the Receipt Document the business purpose and who was involved. Supporting invoices, calendar entries, and emails can help explain the expense. 19:00 Supporting Records for Mileage, Travel, and More Mileage, travel, equipment, contractors, loans, and reimbursements each need records that support the transaction. 20:00 Building an Audit-Ready Workflow Capture receipts promptly, add context, categorize expenses consistently, and save your documents digitally. 22:00 Testing Whether You Can Find Your Records Choose an older transaction or five large expenses. Check whether you can quickly find the records supporting them. 23:00 What to Do When an Audit Letter Arrives Read the request carefully, meet deadlines, organize your response, and speak with a qualified tax professional. 25:00 How Good Documentation Pays Off Organized records make audit responses faster and deductions easier to defend. Clean books also help you make business decisions. 27:00 Why Tax Strategies Need a Paper Trail Putting a strategy into practice includes documenting it. Hiring your kids, for example, requires records of their work and payments. 28:00 Key Takeaways and Next Steps Clean books and timely documentation help you prepare for an audit. Learn where to find support implementing tax strategies. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Are you missing out on the home office deduction because you think your workspace doesn’t qualify? In this episode, Mike Jesowshek explains who qualifies for the home office deduction and how to calculate it using either the simplified or actual expense method. He also breaks down the regular and exclusive use rules, how the deduction differs for sole proprietors and S Corporation owners, and why a qualifying home office could unlock additional business mileage deductions. You’ll learn how to choose the right calculation method, document your workspace, avoid common mistakes, and turn expenses you’re already paying into a legitimate business tax deduction. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ 00:00 How the Home Office Deduction Works The home office deduction allows business owners to turn a portion of expenses they’re already paying, including rent, utilities, insurance, and homeownership costs, into legitimate business deductions. 02:20 Who Qualifies for a Home Office Deduction? A qualifying workspace must be used regularly and exclusively for business. It doesn’t need to be an entire room, but the separation between business and personal use must be clear. 04:15 What Counts as Your Principal Place of Business? Your home doesn’t need to be the only place where you work. A home office may qualify if you regularly use it for administrative or management activities such as bookkeeping, scheduling, invoicing, planning, and customer follow-ups. 06:30 The Simplified Home Office Deduction The simplified method provides a deduction of $5 per qualifying square foot, up to 300 square feet. It requires less recordkeeping but limits the maximum annual deduction to $1,500. 08:50 How the Actual Expense Method Works The actual method calculates your deduction using the percentage of your home used for business. It may include a portion of rent, mortgage interest, property taxes, utilities, insurance, repairs, cleaning, and depreciation. 10:50 Simplified vs. Actual Expenses The simplified method may be easier, but the actual method can produce a significantly larger deduction. Business owners should calculate both methods each year before deciding which one to use. 11:35 How to Claim the Deduction Based on Your Business Structure Sole proprietors and single-member LLCs generally claim the deduction through Schedule C and Form 8829. S Corporation owners typically need an accountable plan to reimburse themselves properly for home office expenses. 13:40 How a Home Office Can Unlock Business Mileage A qualifying home office may establish the starting point of your business day. This can allow trips from your home office to clients, suppliers, job sites, or other business locations to qualify as deductible business mileage rather than commuting. 15:30 Common Home Office Deduction Mistakes Personal use of the workspace, estimated measurements, missing housing records, and incorrect treatment based on business structure can weaken or eliminate the deduction. 16:30 Your Home Office Deduction Checklist Photograph and measure your workspace, confirm your home’s total square footage, collect your annual housing expenses, compare both calculation methods, and document how the deduction will be handled based on your entity type. 17:50 Equipment and Other Home Office Deductions Computers, desks, cameras, microphones, and other business equipment should generally be analyzed separately. The home office calculation focuses on the cost of the qualifying physical space rather than the equipment used to operate the business. 18:25 How to Make Your Home Office Deduction Defensible The goal isn’t to claim your entire home as a business expense. It’s to identify the portion legitimately used for business, document it properly, choose the best calculation method, and revisit the deduction each year. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Are you missing out on a business vehicle deduction, or claiming more than you’re actually allowed? In this episode, Mike Jesowshek explains how business vehicle deductions work, including the difference between the standard mileage and actual expense methods. He also breaks down the 6,000-pound vehicle rule, business versus personal mileage, vehicle ownership, and the records you need to protect your deduction. You’ll learn how to choose the right deduction method, avoid costly mistakes, and turn legitimate business driving into a defensible tax strategy. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ 00:00 How Business Vehicle Tax Deductions Work Vehicle deductions should begin with a legitimate business purpose, not the type of vehicle you want to purchase. Business use determines the deduction, regardless of whose name is on the title or whether the vehicle displays your company logo. 02:29 Standard Mileage vs. Actual Expenses The standard mileage method provides a set deduction for each documented business mile. The actual expense method deducts the business-use portion of costs such as fuel, insurance, repairs, lease payments, interest, and depreciation. 05:20 How to Choose the Right Deduction Method Compare your expected mileage, business-use percentage, purchase price, operating costs, and potential deductions over several years. 06:55 The 6,000-Pound Vehicle Tax Strategy Vehicles with a gross vehicle weight rating above 6,000 pounds may qualify for different depreciation treatment. But the available deduction still depends on business use, vehicle classification, taxable income, and the depreciation method used. 09:45 Should the Vehicle Be in Your Personal or Business Name? A vehicle doesn’t always need to be titled in the company’s name to qualify for a deduction. Personally owned vehicles may be reimbursed for business use, while personal use of a company-owned vehicle may need to be treated as a taxable fringe benefit. 12:30 What Counts as Business Mileage? Driving between your home and regular office is generally considered commuting. Trips between business locations, client meetings, job sites, suppliers, and other qualifying destinations may count as deductible business mileage. 15:15 The Records You Need to Protect Your Deduction Business owners should track the date, destination, purpose, and mileage of every business trip. Mileage records are necessary even when using the actual expense method because they support the vehicle’s business-use percentage. 19:00 How to Claim the Vehicle Deduction Sole proprietors and single-member LLCs generally claim vehicle expenses on Schedule C. S Corporation owners may deduct a company-owned vehicle’s expenses through the business or use an accountable plan to reimburse business use of a personally owned vehicle. 20:20 Business Vehicle Deduction Checklist Establish the vehicle’s business purpose, estimate business and personal mileage, compare both deduction methods, check the vehicle’s weight rating, and consider whether buying or leasing makes more sense. 22:00 Avoid This Expensive Vehicle Tax Mistake A deductible vehicle isn’t free. Before purchasing an expensive truck or SUV for the write-off, calculate the actual tax savings and make sure the vehicle is something the business genuinely needs. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Is growing your business creating more stress instead of more freedom?  In this episode, Mike Jesowshek breaks down what commonly starts to fail as a business reaches $250,000, $500,000, and $1 million in revenue. He explains why your personal capacity, internal systems, financial visibility, and ability to delegate must evolve as the business grows. You’ll learn how to stop becoming the bottleneck, protect profitability, build a team you can trust, and create the systems and proactive tax plan needed to scale without burning out. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (03:00) Building Systems at $250,000 in Revenue Informal processes and information stored in the owner’s head stop working as the business expands. Mike explains how simple checklists and screen recordings can create more consistent results without constant supervision. (07:00) Delegation Becomes Essential at $500,000 Hiring someone doesn’t automatically reduce the owner’s workload. Effective delegation requires clear outcomes, deadlines, decision-making authority, performance measures, and trust in the people you hire. (10:15) Making Tax Planning Proactive As profit increases, reactive tax planning becomes more expensive. Mike covers estimated payments, entity structure, reasonable compensation, retirement opportunities, documentation, and other areas growing businesses should review throughout the year. (13:00) When the Owner Becomes the Bottleneck At around $1 million in revenue, the business may have employees and systems but still depend on the owner for every major decision. Mike shares the warning signs that the company cannot operate without your constant involvement. (14:25) Building Leaders, Not Just Hiring Helpers Every major function of the business needs clear ownership, measurable goals, and appropriate decision-making authority. Developing capable leaders allows the owner to step away from daily operations and focus on direction. (18:20) How the Owner’s Role Must Change The habits that help start a business can become liabilities as it grows. Moving to the next stage requires the owner to spend less time completing tasks and more time planning, coaching, reviewing numbers, and developing people. (19:45) Mike’s Experience Scaling His Accounting Firm Mike shares how keeping every process in his head and remaining involved in every client created problems as his firm grew. He explains how those lessons shaped the way he approached building his next company. (22:25) What Kind of Business Do You Actually Want? Not every owner wants to build a $100 million company. Mike closes by encouraging business owners to define the business and lifestyle they want, then build the systems, team, financial structure, and tax plan required to support it. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Could Bitcoin mining turn a major business expense into a tax-saving opportunity? In this episode, Mike Jesowshek and Colin from Leverage Mining explore how owning mining equipment could help business owners earn Bitcoin and claim potential tax deductions. They break down the upfront costs, participation requirements, and why a tax write-off alone isn’t enough to make this investment worthwhile. You’ll learn who this strategy might suit, what a four-year commitment involves, and the risks to consider before getting started. 🚀 Could Bitcoin mining fit into your tax strategy? Book a call with Leverage Mining to explore the costs, potential tax benefits, and what getting started would involve:  https://preview.khgmedia.com/widget/booking/WM032a6yfqW9p8Ls3WpR?utm_source=mike_jesowshek&utm_medium=referral&utm_campaign=partner_program 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (01:00) Bitcoin Mining vs. Buying Bitcoin Bitcoin mining involves owning equipment that earns Bitcoin, rather than purchasing the asset directly. The discussion explains how mining machines work, why miners join pools, and how rewards are shared. (06:00) Bitcoin Mining as a Tax Strategy Mining equipment may qualify for bonus depreciation, creating an upfront deduction while the business produces Bitcoin over time. The conversation explores how this fits into a broader strategy of purchasing income-producing assets. (08:00) Material Participation and Documentation Using mining losses to offset wages or other business income involves more than purchasing equipment. The discussion covers material participation, tracking business activities, and planning ahead to meet the relevant requirements. (13:00) Equipment Costs and the Four-Year Commitment Colin outlines packages that combine mining machines, hosting, and electricity over four years. They discuss upfront costs, operating arrangements, and why the value of the Bitcoin earned can fluctuate. (17:00) How Much of the Investment Is Deductible? The full package price isn’t presented as a first-year deduction. Using a $100,000 example, they discuss an estimated $70,000 first-year deduction, with remaining electricity expenses spread over later years. (19:00) Bitcoin Halving and Long-Term Returns Mining rewards change over time, and Colin explains why his approach depends heavily on Bitcoin appreciating. The discussion highlights the importance of evaluating potential returns beyond the initial tax benefit. (21:00) What Happens After the Mining Contract Ends? As the four-year agreement ends, owners face decisions about older equipment and whether to purchase new machines. Colin discusses replacement, disposal, and the potential tax implications of selling depreciated equipment. (24:00) Accumulating Bitcoin Over Time Mining produces Bitcoin gradually rather than through a single purchase. Colin explains his preference for holding the Bitcoin earned and taking a long-term approach to price fluctuations. (26:00) Understanding the Risks of Bitcoin Mining Bitcoin prices, network difficulty, changing rewards, and equipment failures can affect results. The conversation also covers hosting fees, electricity contracts, downtime, and questions to ask when evaluating a provider. (31:00) Who Might Be a Good Fit for This Strategy? The discussion focuses on high-income business owners who can commit funds for several years and tolerate volatility. It closes with the importance of participation requirements, documentation, and building a legitimate business strategy. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Discover how you can save over 5 figures in taxes with my 3-step tax shift system in my upcoming masterclass on September 1st at 7PM EST Join here: https://taxsavingspodcast.com/masterclass/ If your business earns between $50,000 and $750,000 in annual profit, you're probably paying thousands more in federal taxes than necessary. But filing a tax return isn’t the same as tax planning.  Proactive tax planning helps you make smarter decisions while there’s still time to reduce your bill. On Tuesday, September 1 at 7:00 PM Eastern Time, Mike Jesowshek, CPA, is hosting a free 90-minute live masterclass on how business owners can cut their tax bills by $15,000 or more. During the training, you’ll learn: 💵 Mike’s three-step Tax Shift System 📊 How proactive planning can uncover missed tax savings 🧾 The difference between tax preparation and tax planning 🏢 How an S Corp election could save an $80,000-profit business around $5,300 per year ✅ Which strategies may apply to your business and income Mike will also stay after the training for a live Q&A, where you can ask about your entity, income, children, rental properties, or other tax questions specific to your situation. The training is completely free, but you’ll need to reserve your seat. Register now at taxsavingspodcast.com/masterclass See you there!

🚀  Discover how you can save over 5 figures in taxes with my 3-step tax shift system in my upcoming masterclass on September 1st 7PM EST Join here:  https://taxsavingspodcast.com/masterclass/ Selling a business, rental property, or investment can create a significant capital gains tax bill. Could investing in an Opportunity Zone help you delay that tax and potentially eliminate taxes on future growth? We cover how Qualified Opportunity Zones work, why the timing of your investment matters and all the rules for investments made in 2026 are very different from those beginning in 2027. You’ll learn about the 180-day investment deadline, the limited deferral available in 2026, and the new five-year deferral beginning in 2027. Most importantly, you’ll learn why an Opportunity Zone investment should make financial sense before considering the tax benefits. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (00:00) What Is an Opportunity Zone? Opportunity Zones encourage investment in designated communities by offering tax benefits to investors who reinvest eligible gains through a Qualified Opportunity Fund. (02:00) The Two Main Opportunity Zone Tax Benefits Investors may be able to defer tax on the original gain and exclude future appreciation from federal capital gains tax after holding a qualifying investment for at least 10 years. (04:00) What Happens to Opportunity Zone Investments in 2026? Gains invested under the current rules generally become taxable by the end of 2026, but the investment may still qualify for the 10-year appreciation benefit. (06:00) Can You Move an Existing Gain Into the New Program? A deferred Opportunity Zone gain recognized at the end of 2026 generally cannot be reinvested under the new rules beginning in 2027. (07:48) How the 180-Day Deadline Affects Late-2026 Gains A new gain realized late in 2026 may qualify for the 2027 rules if the investment is made in 2027 within the required 180-day period. (09:37) What Changes for Opportunity Zones in 2027? The new rules introduce a five-year deferral, a 10% basis increase after five years, and a potential 30% basis increase for qualifying rural investments. (12:04) Should You Invest in 2026 or Wait Until 2027? The right timing depends on when the gain occurred, when the 180-day deadline expires, and whether the investment makes financial sense on its own. (14:04) Five Questions to Ask Before Investing Confirm that the gain qualifies, calculate the exact deadline, identify which rules apply, consider the 10-year holding period, and evaluate the investment without the tax benefit. (16:43) Common Opportunity Zone Myths Mike addresses misconceptions about eliminating the original gain, qualifying properties, reinvesting old gains, rural funds, and missing the 180-day deadline. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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.

Can you deduct your dog, pay your child tax-free, or claim the kitchen table as a home office? Tax rules for small business owners aren’t always straightforward. Wrong assumption could lead to missed deductions or problems with the IRS. In this Q&A episode, Mike answersyour questions. He explains which expenses may qualify when a dog is used for marketing, how hiring children differs between an S corporation and a sole proprietorship, and what happens when a child turns 18. He also covers mileage tracking, missing receipts, home office requirements, unreported Venmo income, retirement plan deadlines, college funding strategies, and whether health-sharing payments qualify for the self-employed health insurance deduction.  👉 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 Hiring Your Children Through an S Corporation Mike explains how a child’s age and the business entity affect income tax, FICA withholding, W-2 employment, and 1099 contractor treatment. 05:03 Deducting Your Dog and Tracking Business Mileage Learn which dog-related marketing expenses may qualify as deductions, which personal pet expenses typically don’t, and how to document business mileage. 09:10 Missing Receipts and Paying for College Through Your Business Mike covers the documentation needed for expenses under $75, reimbursing personally paid business costs, and hiring a child to help fund college. 13:55 Retirement Deadlines and the Home Office Deduction Review important retirement contribution deadlines and find out why working from the family kitchen table generally doesn’t qualify for a home office deduction. 16:28 Hiring a Teenager and Reporting Venmo Income Mike explains W-4 and payroll requirements when hiring a 15-year-old, along with why business income must be reported even when no 1099 is received. 19:26 Health-Sharing Plans and Insurance Deductions Find out whether health-sharing payments qualify for the self-employed health insurance deduction and how to compare their cost with potential tax savings. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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.

Life insurance isn’t just a way to protect your family. For the right business owner, it can also provide tax-efficient growth, access to capital, and long-term financial flexibility. In this episode, Mike and Matt explain how cash value life insurance works, including tax-deferred growth, policy loans, death benefits, and long-term care benefits. They also break down term, whole, and universal life insurance, who this strategy may benefit, and how to avoid choosing an expensive or poorly designed policy. 👉 Need a life insurance policy that fits your financial strategy? Connect with Matt for a policy review and personalized guidance based on your goals: https://lifeincrs.com/tax-savings-podcast 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (01:25) Life Insurance as a Wealth-Building Strategy For some high-income earners and business owners, life insurance can provide more than financial protection. A properly structured policy may support tax-efficient growth, access to capital, and long-term financial stability. (03:25) The Tax Advantages of Cash Value Life Insurance Policy contributions are generally made with after-tax money, but the cash value can grow tax-deferred. Beneficiaries may also receive the death benefit free from federal income tax. (05:20) Understanding Policy Costs and Commissions Permanent life insurance can carry significant upfront commissions and insurance costs. Evaluating those expenses over the policy’s full lifetime provides a more useful comparison than looking only at the first year. (10:10) Accessing Cash Value Through Policy Loans Policyholders may borrow against their cash value without creating an immediately taxable withdrawal. The remaining cash value can continue earning interest, while unpaid loans generally reduce the eventual death benefit. (15:35) Contribution Limits and Modified Endowment Contracts Life insurance doesn’t have the same annual contribution limits as qualified retirement accounts. However, overfunding a policy can turn it into a modified endowment contract and change how withdrawals are taxed. (19:00) Term, Whole, and Universal Life Insurance Explained Term insurance provides temporary protection without accumulating cash value. Whole and universal life policies offer permanent coverage, with different levels of cash value growth, investment exposure, cost, and flexibility. (22:15) Designing a Policy Around Your Financial Goals A policy can be designed to prioritize accessible cash value or a larger death benefit. Additional features may include chronic care riders, participating loans, and fixed or net-zero loan options. (25:30) Who Should Consider Cash Value Life Insurance? This strategy may fit profitable business owners who have already established emergency savings and funded their traditional retirement accounts. It generally shouldn’t be someone’s first savings or investment tool. (30:00) Why Life Insurance Is Often Misunderstood Life insurance is complex and sometimes presented as a solution to every financial problem. Its value depends on whether the policy is properly explained, structured, and integrated into a broader financial plan. (32:10) Reviewing an Existing Life Insurance Policy A policy audit can reveal whether existing coverage is healthy, appropriately designed, and aligned with the owner’s current goals. Before purchasing or changing a policy, review the numbers and consult a professional who understands multiple financial strategies. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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 ⭐

Paying yourself the lowest possible S Corp salary might save taxes today, but it could create a much bigger tax bill later. In this episode, Mike explains how to determine a reasonable S Corp salary based on your role, hours, local market wages, business profit, and cash flow. He also breaks down payroll timing, salary adjustments, documentation, and how to protect your S Corp tax savings while staying compliant with IRS rules. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (01:00) What Is Reasonable Compensation? An S Corp owner who actively works in the business must receive a reasonable W-2 salary based on what the business would pay someone else to perform the same work. (03:05) The Goal Is a Defensible, Documented Salary A reasonable salary shouldn’t be unnecessarily high or aggressively low. It should be supported by a clear process and adjusted as the business changes. (04:05) Factors That Determine an S Corp Salary The owner’s responsibilities, hours, industry, location, role in generating revenue, company profit, cash flow, and stage of growth all affect reasonable compensation. (05:40) The Percentage Method and 40/60 Split Using 40% to 50% of business profit as salary can provide a starting point, but a percentage alone doesn’t replace a complete reasonable compensation analysis. (07:00) Using Market Wages and Replacement Cost Breaking the owner’s work into technical, sales, marketing, and administrative duties can help calculate a salary using local market rates for each role. (10:05) Comparing Salary to Business Profit Reasonable compensation must also make sense in relation to the company’s profit, the owner’s involvement, available cash flow, and whether money is being distributed or reinvested. (11:05) How Often Should an S Corp Owner Run Payroll? Monthly or biweekly payroll is generally recommended, with a review later in the year to make any necessary adjustments or catch-up payments. (13:15) How to Document Reasonable Compensation Keep a written salary analysis, description of duties, estimated hours, market-wage data, payroll records, profit information, and year-end review notes. (15:05) Two Businesses With Very Different Salaries A real-world example shows why two owners with identical business profits can reasonably receive drastically different salaries based on their actual involvement. (16:35) Protecting Your S Corp Tax Savings The strongest S Corp strategy uses a salary that is reasonable, defensible, and documented instead of simply chasing the lowest possible number. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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.

Will electing S Corporation status ALWAYS save your business thousands in taxes? While that can be true, an S Corp also brings additional payroll requirements, tax filings, costs, and responsibilities. In this episode, we break down how an S Corp reduces self-employment taxes, when the election usually makes financial sense, and which factors you need to consider before making the switch. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters: (00:00) What Is an S Corporation? An S Corp is a tax election for an existing LLC or corporation, not a separate type of business entity. (03:00) How an S Corp Can Reduce Your Taxes Splitting business income between a reasonable salary and distributions can reduce the amount subject to self-employment taxes. (05:00) When Does an S Corp Start Making Sense? An S Corp generally becomes worth exploring when a business consistently earns around $60,000 or more in annual profit. (08:00) Who Is a Good Candidate for an S Corp? Consistent profit, active owner involvement, clean bookkeeping, and reliable cash flow are important signs that an S Corp could be a good fit. (10:00) When an S Corp May Not Save You Money  Low or inconsistent profit, high reasonable compensation, state-level taxes, and an existing high-paying W-2 job can change the calculation. (12:00) The Reasonable Salary Requirement  S Corp owners who actively work in the business must pay themselves reasonable W-2 compensation before taking distributions. (13:00) How Often Should an S Corp Owner Run Payroll? Monthly or biweekly payroll is generally the safest approach, while waiting until the end of the year can create compliance and cash-flow problems. (14:00) Hidden S Corp Costs and Responsibilities  Payroll filings, W-2s, bookkeeping, accountable plans, health insurance reporting, and salary documentation must all be handled correctly. (15:00) The S Corp Decision Framework Use these questions to evaluate profitability, salary, payroll, state taxes, bookkeeping, and whether the potential savings exceed the added costs. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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.

👉 Ready to simplify your recordkeeping? Check out Shoeboxed to organize receipts, track mileage, and keep your business expenses audit-ready. Visit https://referrals.shoeboxed.com/mb4p7wl1ithi You could qualify for thousands of dollars in tax deductions, but without the right documentation, the IRS could take them away. Mike sits down with Doug Breaker, owner of Shoeboxed, to explain how proper recordkeeping helps business owners protect their tax deductions. They break down what to document for receipts, meals, mileage, home offices, and business travel, how long to keep your records, and how simple tracking systems can help you stay organized and audit-ready. 👉Find out how much your business could save in taxes. TaxSavingsPodcast.com/scorecard  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ Chapters:  01:00 Doug Breaker’s Journey to Owning Shoeboxed Doug explains how he went from working as a corporate CEO to purchasing Shoeboxed and becoming a business owner. 05:00 How Shoeboxed Simplifies Recordkeeping Doug shares how Shoeboxed helps business owners digitize receipts, automatically collect expense information, and classify business mileage. 06:00 What Counts as Proper Documentation? Receipts should capture details such as the date, vendor, amount, and business purpose, while mileage logs require the date, destination, mileage, and purpose of the trip. 11:00 How to Organize a Backlog of Receipts Business owners with years of disorganized receipts should begin by digitizing recent records and creating a consistent process for tracking new expenses. 15:00 What an Audit-Ready Mileage Log Should Include A proper mileage log should record the date, destination, miles driven, and business purpose of each trip rather than relying on an annual estimate. 19:00 How Long Should You Keep Business Tax Records? Doug recommends keeping receipts, mileage logs, and supporting documentation for at least three years in a secure and accessible location. 22:00 When Driving From Home Becomes Deductible Mileage Driving from home to a regular workplace is generally commuting, but traveling from a qualifying home office to another business location can create deductible mileage. 27:00 Deducting Expenses Before a Business Makes Money Expenses incurred before a business begins operating may be treated as startup costs. Establishing a paying customer can help show that the business has moved into its operational stage. 32:00 Why Better Recordkeeping Protects Your Tax Savings Consistently tracking every receipt and business mile helps protect deductions, reduce audit anxiety, and keep more money in the business. Podcast Host: Mike Jesowshek, CPA – Founder and Host of Small Business Tax Savings Podcast Join 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 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.