Have you ever wondered if you could hire your older child to watch your younger one and claim it as a business expense? Or are you maximizing the benefits of a Health Savings Account to its fullest potential? In this Q&A episode of the podcast, host Mike Jesowshek answers a series of listener-submitted questions covering a wide range of topics pertinent to small business owners, such as tax deductions, business expenses, payroll management, and tax strategies. Mike provides detailed insights on various scenarios, such as employing children, maximizing HSA contributions, and the proper way ..read more

Have you ever wondered how to structure your multiple business ventures efficiently while minimizing your tax burden?  Mike Jesowshek delves into the complexities of business structuring, particularly for individuals owning multiple businesses or in partnership. He emphasizes the utility of S Corporations in reducing self-employment taxes and the importance of establishing a parent S Corporation to streamline business operations, financial management, and tax filing. Mike advocates for separate bookkeeping for each entity, despite their consolidation under the parent S Corp, to maintain ..read more

Are you perplexed by estimated taxes and worried about potential penalties? Discover how to navigate the U.S. tax system's pay-as-you-go approach and strategically plan your payments to stay on top of your tax obligations! In this episode, Mike Jesowshek discusses the importance of understanding and paying estimated taxes in the U.S., emphasizing the "pay as you go" system. He explains the concept of estimated taxes, key due dates for each quarter, and the significance of making timely payments to avoid penalties and interest. Mike introduces the "safe harbor" rule, which helps taxpayers avoi ..read more

Are you maximizing the potential of your real estate investments through 1031 exchanges and Opportunity Zones? In this podcast, Mike Jesowshek and guest Michael Scherer delve into the intricacies of 1031 exchanges, focusing on various replacement property options, including Delaware Statutory Trusts (DSTs) and Qualified Opportunity Zones. They discuss the advantages of passive investment through DSTs, the strategic importance of planning and consulting with tax advisors, and the potential tax deferral benefits of investing in Opportunity Zones. The conversation emphasizes the need for investo ..read more

Are you maximizing your real estate investment potential through tax-deferred strategies?  Mike Jesowshek and Michael Scherer delve into the intricacies of 1031 exchanges. They explain its purpose, benefits, and the critical role of proper planning and advice from tax advisors. They emphasize the necessity of involving a qualified intermediary and the potential financial advantages, including tax deferral and strategic reinvestment, to maximize wealth building in real estate investment. [00:00 - 04:52] 1031 Exchanges and its Planning and Prerequisites Mike Jesowshek introduces the topi ..read more

Ever wondered how you could significantly reduce your taxable income from real estate investments in just one year? In this episode, Mike Jesowshek introduces Gabriel Florentino from Engineered Tax Services to discuss cost segregation studies, a tax strategy for real estate investors aiming to accelerate depreciation deductions. Gabriel explains the concept and benefits of cost segregation, emphasizing its significant impact on reducing taxable income by identifying and reclassifying property components to shorter depreciable lives. The discussion also covers the importance of understanding a ..read more

Curious about how real estate can help you grow your wealth and save on taxes? In this episode, Mike Jesowshek discusses how real estate can serve as a tool for both wealth-building and tax savings. He emphasizes the concept of depreciation, whereby the cost of a rental property can be deducted over time, and explains how this, along with other operating expenses, can offset rental income. He also delves into strategies for utilizing passive losses to offset ordinary income, such as qualifying as an active real estate investor or a real estate professional. Additionally, he touches on the "sh ..read more

Are you worried about filing your tax return on time or paying your tax bill? In this episode, Mike Jesowshek discusses tax extensions and strategies for paying tax bills, addressing common misconceptions and providing practical advice. He clarifies that filing an extension does not increase audit risk and emphasizes the importance of timely filing and payment. Mike outlines options for those who can and cannot afford their tax bills, including installment agreements and offers in compromise. Throughout the discussion, he stresses the significance of proactive tax planning to avoid financial ..read more

Ever wondered if your global business ventures could be affecting your U.S. taxes more than you realize?  In the podcast episode, Mike Jesowshek delves into the intricacies of foreign income for small business owners, covering essential aspects such as reporting requirements, types of foreign income, tax treaties, exemptions, the foreign earned income exclusion, the foreign tax credit, and compliance with reporting obligations. He emphasizes the importance of U.S. citizens and residents reporting worldwide income on their U.S. tax returns, regardless of where the income is earned. Mike a ..read more

In this episode, Mike Jesowshek answers various listener questions regarding tax strategies, S corporation elections, hiring children for tax benefits, and setting up retirement plans for businesses with non-owner employees. The episode emphasizes the importance of structuring businesses correctly to maximize tax savings, including the considerations for S corporation status, late elections for business structures, the benefits of hiring family members, and the intricacies of purchasing a business and tax implications. Mike also discusses the potential of setting up retirement plans for employ ..read more