Small Business Tax Savings Podcast

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.

Can a rental property put $30,000 in your pocket without adding $30,000 to your taxable income? Let’s talk about rental property tax strategies Mike explains how rental real estate can create tax savings even when you can’t use rental losses to offset your business or W-2 income. He breaks down the difference between cash flow and taxable income, how depreciation can shelter rental income, and what happens to suspended passive losses. He also covers short-term rental rules, real estate professional status, common entity mistakes, and the key questions to ask before buying a rental property. 👉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 How Rental Properties Create Tax Savings Rental properties don’t need to generate a usable tax loss to provide tax benefits. Depreciation and other deductions can allow investors to earn positive cash flow without reporting the same amount as taxable income. 02:15 What Happens When You Can’t Use a Rental Loss? Rental losses are generally passive and can’t usually offset W-2 or active business income. Unused losses are suspended until they can offset passive income or be used when the property is sold. 05:15 Rental Cash Flow vs. Taxable Income Cash flow is the money that reaches your pocket, while taxable income is the amount the IRS taxes. 06:15 How $30,000 of Rental Cash Flow Could Create No Taxable Income A business owner earning $200,000 could receive another $30,000 in rental cash flow while still reporting around $200,000 of taxable income. Depreciation and rental deductions could shelter the additional income. 08:45 When Rental Losses Can Offset Active Income Short-term rental treatment, real estate professional status, and certain active participation rules can allow rental losses to offset W-2 or business income. 12:30 How Rental Property Depreciation Works Residential rental buildings are generally depreciated over 27.5 years, while commercial properties are depreciated over 39 years. 14:45 Why You Shouldn’t Hold Rental Property in an S Corporation Rental properties are commonly held in LLCs for liability protection, but generally shouldn’t be placed inside an S corporation. Active business operations and passive rental activities should also be kept legally separate. 17:15 Building a Complete Rental Property Tax Strategy A strong rental strategy combines positive cash flow, depreciation, expense tracking, appreciation, debt paydown, suspended losses, and potential strategies such as hiring your children or completing a 1031 exchange. 19:15 Four Questions to Ask Before Buying a Rental Property Before investing, determine whether the property makes sense without the tax benefits, what its cash flow will be after debt payments, how much income will be taxable, and whether any rental losses can be used immediately or will be suspended. 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.

👉 Interested in learning more about oil and gas investing? Email us at ask@taxsavingspodcast.com and we’ll connect you with Nick White and the team at US Energy. Big tax deduction or risky investment? Oil and gas investing can be a powerful tax strategy for high-income business owners, but it’s not something to jump into just because you want a write-off. In this episode, Mike sits down with Nick White from US Energy to break down how oil and gas investing works, where the tax benefits come from, and why intangible drilling costs can create a large first-year deduction. They cover who is a good fit, how these investments can potentially offset W-2 income, business income, K-1 income, and capital gains, what the return and cash flow profile may look like, and the key risks investors need to understand before getting involved. 👉 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 How Oil and Gas Investing Creates Tax Benefits Oil and gas investing is built around government incentives for domestic energy production. Investors who participate directly in drilling funds may be able to receive large first-year deductions through intangible drilling costs. 06:00 Intangible Drilling Costs Explained Intangible drilling costs include expenses tied to the drilling process that do not have a depreciation schedule, such as labor, roads, and hydraulic fracturing. These costs can help create a large year-one deduction for qualified investors. 07:45 Offsetting W-2, Business, K-1, and Capital Gains Income Unlike many real estate losses, oil and gas deductions may be able to offset active income, including W-2 income, business income, K-1 income, and capital gains. This is one reason the strategy is often discussed with high-income earners. 09:15 Who is Oil and Gas Investing a Good Fit For? Oil and gas investing is generally geared toward accredited investors, including individuals with at least $1 million in net worth excluding their primary residence, or income of at least $200,000 for single filers and $300,000 for joint filers. 11:15 Key Risks Investors Need to Understand Oil and gas investing comes with real risks, including drilling risk, pricing risk, concentration risk, and company structure risk. Look closely at debt levels, drilling strategy, diversification, and whether the company is focused on proven production areas. 17:00 Timing Your Investment Before Year-End While an investment may qualify if completed by December 31, starting earlier gives investors more time to understand the deal, plan properly, and avoid rushed year-end decisions. 23:30 QBI, SALT, and Phaseout Planning Oil and gas deductions may help business owners reduce taxable income enough to phase back into other tax benefits, such as the qualified business income deduction or state and local tax deductions. 26:00 Common Mistakes When Evaluating Oil and Gas Deals Not every deal is structured the same way. Investors should avoid chasing deductions blindly and instead evaluate the partnership structure, use of debt, drilling approach, technology, risk profile, and long-term cash flow potential. Disclaimer: This episode was not sponsored. This conversation is for educational purposes only and is not investment, legal, or tax advice. It is not a recommendation or endorsement of any specific company, fund, security, or oil and gas offering. Oil and gas investments may involve substantial risk, illiquidity, commodity price volatility, operational risk, tax complexity, and possible loss of principal. Tax treatment depends on each taxpayer’s facts, investment structure, at-risk basis, passive activity rules, and professional advice. Past results do not guarantee future results. 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.

Free money for kids? Not so fast. Trump Accounts could become one of the newest long-term wealth-building tools for families, but you need to understand how they work, who qualifies, and how they fit into a bigger tax and investment strategy. In this episode, Mike breaks down everything you need to know about the Trump Accounts. He covers the contribution rules, tax-deferred growth, employer contribution opportunities, Roth conversion planning, and how Trump Accounts compare to 529 plans, Roth IRAs, custodial accounts, and brokerage accounts. 👉 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 What Are Trump Accounts? Trump Accounts are new savings vehicles for children under 18, created under the One Big Beautiful Bill Act. They are designed to encourage early investing, long-term compounding, and tax-deferred growth. 02:25 The $1,000 Government Seed Contribution Children born between 2025 and 2028 may qualify for a $1,000 federal contribution. This is not spending money; it is long-term investment capital placed into the child’s Trump Account. 03:30 Contribution Rules and Tax Treatment Families can contribute up to $5,000 per year until the child turns 18. Contributions are not tax-deductible, but the growth inside the account is tax-deferred. 05:30 Roth Conversion Planning for Trump Accounts Once the child reaches adulthood, the account transitions into a traditional IRA structure. Low-income years may create an opportunity to convert portions into a Roth IRA. 09:15 Trump Accounts vs. 529 Plans and Roth IRAs for Kids 529 plans focus on education, while Trump Accounts focus on long-term wealth building. Roth IRAs are still a strong option for kids with earned income, but Trump Accounts can help fill the gap when a child does not qualify yet. 12:25 Downsides of Trump Accounts Trump Accounts are not perfect for every family. Funds are locked up until adulthood, the child eventually controls the account, investment choices may be limited, and future taxation still needs to be planned for. 13:35 The Stacking Strategy for Family Wealth Planning Families do not have to rely on just one account type. A 529 plan, Roth IRA, Trump Account, brokerage account, or custodial account can each serve a different purpose depending on the family’s goals and cash flow. 14:40 Final Strategy Thoughts on Trump Accounts Trump Accounts may not be an automatic fit for everyone, but they should be considered as part of a larger family wealth plan, especially for children eligible for the $1,000 government contribution. 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.

Don’t wait until the last minute to start tax planning. Mid-year is one of the best times for business owners to review their tax situation. Most business owners wait until year-end to ask, “How can I lower my tax bill?” But by then, some of the best opportunities are already gone. Instead of making proactive tax-saving moves, you’re left doing damage control. In this episode, Mike walks through a simple mid-year tax checkup every small business owner should do before December. He covers how to review your income, estimate your tax liability, clean up your bookkeeping, evaluate your entity structure, plan retirement contributions, think through major purchases, and identify tax strategies you still have time to implement before year-end. 👉 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 Why Mid-Year Is the Sweet Spot for Tax Planning Mid-year gives business owners two major advantages: enough real financial data to review and enough time left in the year to implement strategies. 03:00 Grade Your Tax Planning Progress Business owners should evaluate whether they’ve only learned about tax strategies or have actually started implementing them. 04:00 Review Your Bookkeeping Before It Becomes a Problem Accurate bookkeeping is the foundation of good tax planning. Mid-year is the time to catch missing transactions, miscategorized expenses, personal charges, payroll errors, and missed deductions. 05:20 Review Your Entity Structure Your business structure should match your current income, profit, and tax strategy. This includes reviewing whether an LLC, S corporation, or multi-entity setup makes sense. 07:40 Review Retirement Contribution Opportunities Mid-year is a good time to look at retirement plan options, contribution goals, employee benefits, and whether your current plan still fits your business. 09:30 Analyze Big Purchases Before Making Them Buying equipment or vehicles just for the write-off is not a good strategy. Business owners should review whether the purchase is needed, how it will be paid for, and whether this year or next year makes more sense. 11:10 Look for Missed Tax Strategies Mid-year still leaves time to implement strategies like hiring your kids, using the Augusta Rule, setting up an accountable plan, reviewing health insurance deductions, and timing income and expenses. 13:20 Review Core and Advanced Tax Strategies Business owners who already use tax strategies should review whether they’re getting the full benefit. Higher-income business owners may need to look at more advanced planning opportunities. 16:00 Tax Planning Is Not a December Activity The best tax-saving opportunities happen when business owners still have time to make decisions, fix mistakes, and plan strategically before year-end. 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.

Stop treating your retirement like a someday problem…For business owners, the right plan can be a valuable tax strategy. But too many entrepreneurs wait too long, choose the wrong plan, or assume a 401(k) is only for big companies. In this episode, Mike sits down with Matt Ruttenberg to explain how retirement plans work for small business owners. They break down the differences between SEP IRAs, SIMPLE IRAs, solo 401(k)s, safe harbor 401(k)s, and defined benefit plans, plus the questions you should ask before choosing a plan, including your contribution goals, employee needs, cost, timing, and tax savings potential. 🚀 Ready to find the right retirement plan for your business? Start here: https://lifeincrs.com/tax-savings-podcast 👉 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 Why Retirement Planning Matters for Business Owners The wrong retirement plan can cost business owners tax savings, growth, and long-term financial security. 01:20 Retirement Plan Options for Business Owners A breakdown of SEP IRAs, SIMPLE IRAs, solo 401(k)s, safe harbor 401(k)s, defined benefit plans, and executive plans. 02:00 How to Choose the Right Plan The right plan depends on the owner’s goals, employee needs, contribution targets, and tax strategy. 04:30 Retirement Plans for Businesses With Employees Traditional 401(k)s, SIMPLE IRAs, state retirement programs, and safe harbor plans can help businesses offer employee benefits. 08:00 Retirement Plans for Solo Business Owners Owners without eligible employees may consider an IRA, Roth IRA, SIMPLE IRA, solo 401(k), or defined benefit plan. 11:35 Time, Maintenance, and Costs Plan setup and maintenance may include payroll setup, employee deferrals, compliance, annual testing, filings, and administrative costs. 18:50 Why Not All 401(k)s Are Created Equal Payroll-based 401(k)s are easier to start, while custom plans offer more flexibility for tax strategy, plan design, and business growth. 27:10 Tax Credits, Deadlines, and Final Takeaways SECURE 2.0 tax credits may help offset plan costs, but timing matters. Starting early helps avoid missed deadlines and lost 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.

Small tax mistakes can cost you thousands, even when you think you’re doing everything right. From missing a filing deadline to misunderstanding how a deduction works, small errors can quickly turn into penalties, lost deductions, and a higher tax bill. In this episode, Mike answers real tax questions from small business owners covering gambling losses, BOI reporting, moving an S corporation to another state, the Augusta Rule, HSAs, late 1099s, estimated tax penalties, startup expenses, vehicle write-offs, and more. He breaks down the rules, explains the available options, and shares practical steps to help you stay compliant and avoid costly tax mistakes. 👉 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 Gambling Losses, BOI Reporting, and Moving an S Corp Mike explains gambling deductions, current BOI filing rules, and what happens when an S corporation moves states. 05:40 The Augusta Rule, HSAs, and Nonprofit Approval Learn how to document Augusta Rule meetings, coordinate HSA contributions, and apply for 501(c)(3) status. 10:20 Health-Sharing Plans, Late 1099s, and Estimated Tax Penalties Mike covers health-sharing deductions, missed 1099 deadlines, and penalties after a late-year property sale. 16:25 Seasonal Income, Inventory Credit, and Pre-Revenue Businesses Find out how seasonal businesses handle estimated taxes, how much inventory to finance, and what to file before earning revenue. 20:15 Late Schedule C Filings, C Corp Owner Pay, and Vehicle Write-Offs Mike explains prior-year Schedule C filings, how C corporation owners are paid, and choosing between mileage and actual vehicle expenses. Resources Mentioned: 👉 www.FinCen.gov 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.

Your CPA isn’t saving you money… And it’s probably not their fault. Many business owners expect their CPA to handle everything: bookkeeping, tax filing, tax strategy, and financial guidance. In this episode, Mike breaks down the four financial roles every business owner needs to understand: bookkeeper, tax preparer, tax strategist, and CFO or advisor. He explains what each role does, what they do not do, and how building the right financial team can help you stay compliant, make better decisions, and legally lower your tax bill. 👉 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 01:45 The Four Financial Roles Every Business Owner Needs A strong financial team is usually made up of multiple roles, not one person. The key roles are bookkeeper, tax preparer, tax strategist, and CFO or advisor. 02:00 The Bookkeeper: The Historian Bookkeepers track income, expenses, transactions, and financial statements. They help create clean, accurate books, but they usually do not provide tax strategy or planning advice. 03:00 The Tax Preparer: The Reporter Tax preparers file returns using completed books and past financial data. Their work focuses on compliance, not optimization, which is why tax filing alone usually does not create tax savings. 04:25 The Tax Strategist: The Architect Tax strategists look forward and build a plan to legally reduce taxes. This may include timing income, maximizing deductions, reviewing entity structure, and implementing proactive tax strategies. 05:55 The CFO or Advisor: The Navigator A CFO or advisor focuses on bigger financial decisions like cash flow, growth, profitability, and next steps. This role becomes more important as the business scales. 08:35 What a CPA Actually Is A CPA is a credential, not a guaranteed service package. Some CPAs prepare tax returns, some provide planning, some focus on bookkeeping, and some do not work in tax at all. 11:35 Where TaxElm Fits Into the Financial Team TaxElm focuses on the tax strategy layer. It does not replace bookkeepers or tax preparers, but helps business owners with proactive year-round planning and strategy implementation. 13:35 How to Know What Your Business Actually Needs The starting point depends on the gap in your business. Messy books point to bookkeeping, recurring surprise tax bills point to tax planning, and growth challenges may point to CFO-level advisory. 16:00 A Simple Framework for Your Financial Team Business owners need clean books, accurate filing, proactive planning, and strategic growth. 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.

Your bookkeeping changes everything from a tax standpoint. If your books are messy, outdated, or based on guesswork, your tax planning is already working with bad information. You may miss deductions, misjudge your profit, make poor year-end decisions, or overpay the IRS without realizing it. In this episode, Mike breaks down why bookkeeping is not just administrative work. It is the foundation of smart tax planning. He explains what bookkeeping actually is, how your profit and loss statement and balance sheet affect your taxes, and why clean, accurate books help business owners make better decisions, reduce tax-season stress, and uncover more opportunities to lower their tax bill. 👉 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 00:58 Why Business Owners Ignore Bookkeeping Early Many new business owners focus on sales, growth, employees, and operations while treating bookkeeping as an afterthought. This creates problems later with taxes, stress, and missed opportunities. 03:15 Why Bookkeeping Is a Tax Strategy Tax strategy starts with accurate data. Business owners can’t maximize deductions, time income, plan asset purchases, or make smart tax decisions if their numbers are wrong. 06:30 Understanding the Profit and Loss Statement The profit and loss statement shows income, expenses, and profit. Since taxable income often starts with profit, this statement is where many tax-saving opportunities begin. 10:45 The Main Types of Bookkeeping Transactions There are four main transaction types to track: bank and credit card transactions, non-cash transactions, invoices, and bills. Where each transaction lands affects the tax impact. 13:30 Common Bookkeeping Mistakes Business Owners Make Common mistakes include inconsistent tracking, waiting until tax season, mixing business and personal expenses, and failing to keep clean records for 1099s. 15:00 What Accurate Books Actually Give You Clean bookkeeping helps business owners stop overpaying taxes, see opportunities in real time, make better decisions, reduce tax-season stress, and move from reactive to proactive planning. 16:00 A Simple System for Better Bookkeeping A simple bookkeeping system starts with cloud-based software, weekly transaction categorization, separate business and personal finances, and professional help when needed. Resources Mentioned: 👉 Kick: https://refer.kick.co/mike-jesowshek-cpa 👉 Quickbooks: https://quickbooks.partnerlinks.io/4k3apzwyyyhf 👉 Xero: https://xero5440.partnerlinks.io/i98ammvf3g9h-nx0cim 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.

Hiring one remote employee in another state changes everything from a tax standpoint. The same goes for selling products or services across state lines. Once your business creates a connection to another state, that state may expect you to register, file, collect taxes, or handle payroll compliance there. In this episode, Mike sits down with Nellie Akalp, CEO and Co-Founder of CorpNet, to break down state tax nexus in plain English. They explain what creates nexus, why remote employees and multi-state sales can trigger tax obligations, and what business owners need to do to avoid penalties, back taxes, and compliance headaches. 🚀 Need help registering in another state, setting up payroll tax accounts, or staying compliant as your business grows? Visit CorpNet at https://www.corpnet.com/?PID=1071 👉 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 00:58 What Is State Tax Nexus? State tax nexus is the connection your business has to a state that creates a legal obligation to follow that state’s tax laws. Nellie explains the two main types of nexus business owners need to understand: employee nexus and sales nexus. 03:30 Hiring Remote Employees in Another State Hiring one remote employee in another state can trigger payroll tax obligations, unemployment insurance registration, and state compliance requirements. Mike and Nellie explain why this should not stop you from hiring great talent, but it does need to be handled properly. 06:30 Why You Should Not Run Payroll by Hand Payroll tax rules change often, and running payroll manually can create serious compliance issues. Nellie explains why business owners should use payroll software or a payroll provider once they start hiring employees. 09:00 Common Mistakes Business Owners Make With Employee Nexus The biggest mistake is not knowing nexus exists. Nellie shares common issues like hiring remote employees without registering in the correct state, running payroll before accounts are set up, and forgetting ongoing filing requirements. 12:00 What Is Economic Nexus? Economic nexus is based on how much you sell into a state, even if you do not have an office or employees there. Nellie explains how the South Dakota v. Wayfair case changed the rules for out-of-state sellers. 14:00 Sales Thresholds and Multi-State Tax Obligations A common benchmark for economic nexus is $100,000 in sales or 200 transactions annually, but rules vary by state. Mike and Nellie explain why business owners should track sales by state and consider a nexus study as they grow. 16:30 Why E-Commerce Businesses Are More Exposed Online businesses often assume they have nothing to worry about because they do not have a physical location in other states. Nellie explains why e-commerce sellers can be especially exposed when they sell across multiple states. 18:00 Foreign Qualification and State Registration Some states may require your LLC or corporation to foreign qualify before registering for payroll tax accounts or sales tax accounts. Nellie explains what foreign qualification means and when it may apply. 20:30 Why Closing State Accounts Matters If you stop doing business in a state, terminate an employee, or move operations, you may need to close your state accounts properly. Otherwise, your business may keep receiving notices or filing requirements even with no activity. 22:30 What Happens If You Ignore Sales Tax Nexus? If your business has sales tax nexus and does nothing, states may assess back taxes, penalties, and interest. Mike and Nellie explain why sales tax exposure can be riskier because there may not be an automatic warning when you cross the line. 27:00 How to Fix Nexus Issues and Stay Compliant Nellie explains the three key steps: identify where you have nexus, get properly registered, and put a system in place to stay compliant. The goal is to stay proactive before a state comes knocking. 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.

You spend money on meals and travel all the time; Client lunches, flights, hotels, conferences, team dinners, and networking events are all part of running a business. But most business owners don’t know what is actually deductible anymore. In this episode, Mike breaks down the 2026 rules for meals, travel, and entertainment deductions. He explains what still qualifies, what changed, what is no longer deductible, and how business owners can turn everyday spending into legitimate tax savings without creating unnecessary IRS risk. 👉 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 00:58 Why Meals and Travel Deductions Matter Meals and travel are common business expenses, but many owners either under-deduct or deduct the wrong things. The goal is to turn qualified spending into pre-tax deductions with a clear business purpose. 02:30 How to Deduct Meals in 2026 Most business meals are 50% deductible in 2026. This includes client lunches, vendor meetings, and prospect meals, as long as there is a real business discussion. 04:30 When Meals Can Be 100% Deductible Some meals can be 100% deductible, such as food provided at sales seminars, company events, or employee parties when structured correctly. 06:00 Entertainment Rules Business Owners Need to Know Entertainment is generally not deductible, even if business is discussed. But meals and drinks purchased separately at those events may still qualify. 08:30 How Business Travel Deductions Work Business travel can include 100% deductions for flights, hotels, and transportation. Travel meals are generally 50% deductible. 11:30 Business Days, Tax Home Rules, and Mixed Travel To deduct travel, the trip needs a clear business purpose and must take you away from your tax home. Mike also explains business days, weekend rules, and mixed personal travel. 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.

Should you open another LLC, elect S Corp status, or create a more advanced business structure? Mike breaks down when a multi-entity structure makes sense, and when it creates more confusion than value. Learn when one LLC is enough, how S Corps and partnerships fit in, and why timing matters. Structure too early and you create chaos. Wait too long and you expose yourself to risk. 👉 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 (00:40) The Problem With “Just Open Another LLC” More entities do not automatically mean more tax savings. Opening LLCs too early can create costs, confusion, messy bookkeeping, and unnecessary complexity. (02:50) Active vs. Passive Business Activity Active operating businesses and passive activities, like rental real estate or investments, should usually stay separate because they have different tax treatment and risk profiles. (04:15) The First Triggers for Adding Another Enti ty Higher income, multiple revenue streams, different types of business activity, and different risk levels can signal that it may be time to consider a multi-entity structure. (08:00) Using an S Corp as a Management Company Instead of creating multiple S Corps, active LLCs can often be owned by one main S corporation, helping simplify tax filings, payroll, and planning. (11:15) How Partnerships Change the Structure When a partner enters the picture, a new entity is usually needed to create clean ownership, clear agreements, and easier exits. (14:15) The Risk of Structuring Too Early Creating multiple LLCs before there is real revenue or activity can lead to annual fees, confusion, co-mingled funds, and bookkeeping problems. (16:00) How to Know When You Are Ready Different income types, multiple revenue streams, liability concerns, sufficient profit, and current or future partners are all signs that a multi-entity structure may be worth considering. (20:00) The Bottom Line on Multi-Entity Structures Multi-entity structures are not about looking sophisticated. They are about solving real business problems at the right time, without creating chaos or waiting until the business is exposed. 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.