Are Your Business Expenses Audit-Ready? With Shoeboxed Owner Doug Breaker

Are Your Business Expenses Audit-Ready? With Shoeboxed Owner Doug Breaker

👉 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 [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 [http://taxsavingspodcast.com/scorecard]  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [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 [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

How Rental Properties Create Tax-Free Cash Flow

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 [http://taxsavingspodcast.com/scorecard]  🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [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 [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

Oil & Gas Tax Investing: The Strategy High-Income Business Owners Should Understand

👉 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 [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters:  01:00 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 [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

Trump Accounts Explained: Gimmick or New Savings Tool for Kids?

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 [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters: 01:00 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 [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.

The Mid-Year Tax Checkup Every Business Owner Needs

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 [https://www.taxsavingspodcast.com/starterkit] 🚀 Book your free demo call today. Click here or visit: https://taxelm.com/demo/ [https://taxelm.com/demo/] Chapters 01:00 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 [https://taxelm.com] 🚀 Visit:  https://www.TaxSavingsPodcast.com [https://www.taxsavingspodcast.com]  🚀 Check Out TaxElm: https://taxelm.com/ [https://taxelm.com/] 🚀 Join our Free Facebook Group: https://www.facebook.com/groups/taxsavings/ [https://www.facebook.com/groups/taxsavings/] 🚀 YouTube: www.TaxSavingsTV.com [http://www.taxsavingstv.com] 👋🏼 GET IN TOUCH You can Tweet @MJesowshek with any feedback, ideas, or thoughts about the lessons you've learned from the episodes. We want to thank you personally for tuning in 🙏 🙌LEAVE A REVIEW If you enjoy the podcast, please leave a 5-star review on Apple Podcasts or Spotify—it helps more business owners find the show ⭐ 🎙 ABOUT THE PODCAST The Small Business Tax Savings Podcast is your go-to resource for cutting-edge tax strategies to help entrepreneurs legally slash their tax bills. Hosted by Mike Jesowshek, CPA, this show breaks down complex tax topics into clear, no-fluff insights so you can keep more of your hard-earned money.