The Jeff Trapp Podcast

Summer is when most business owners stop thinking about taxes. The weather is nice, vacations are booked, kids are out of school, and tax planning gets pushed to the back burner. But what many business owners don't realize is that some of the best tax-saving opportunities of the year happen during the summer months. In this episode, I share several overlooked tax strategies that business owner...

Most business owners think their tax problem shows up in April. Here’s the reality. Your tax bill isn’t decided when you file. It’s the result of everything that happened in the 12 months before. In this episode, I break down why messy financials, poor systems, and lack of real data visibility are the real reasons business owners overpay the IRS every year. I walk through real examples, including...

We had a client go from a $1 million tax bill to under $20,000. Same income. Different strategy. In this episode, I walk through what actually made that possible and why most people never access these kinds of outcomes. It’s not about finding one “secret” strategy. It’s about understanding timing, structure, and execution. I also break down the biggest mistake I see over and over again. People tre...

Most high-income earners believe the tax system is working against them. In this episode, I break down why that belief exists and what is actually happening behind the scenes. The tax code is not designed to punish success. It is designed to reward specific behaviors. We walk through what I call the W-2 tax trap and why many professionals feel stuck paying more as they earn more. Then we shift int...

This is not a normal tax season—and this is not a year for procrastination. In this episode of The Jeff Trapp Podcast , I break down why the current tax environment is unlike anything we’ve seen in years. Between IRS staffing shortages, processing delays, increased scrutiny, and lingering backlogs, the system isn’t broken; it’s overwhelmed. And when the IRS is overwhelmed, taxpayers who wait until...

Happy New Year and welcome to the first episode of 2026. I'm Jeff Trapp, and today we're diving into everything you need to know to start the year off strong. From estimated tax payments to key filing deadlines for S corporations, partnerships, C corps, and individuals, this episode covers the must-know dates and rules for Q1. We’ll also unpack major updates from the new tax law, including revised...

In this episode, Jeff Trapp shares year-end tax strategies that business owners and high-income W-2 earners can still take advantage of before the clock strikes midnight on December 31st. From prepaying business expenses and deferring revenue to bonus depreciation on vehicles and charitable contributions, this episode walks through timely, actionable tactics that can still impact your 2025 return....

In this episode, Jeff Trapp answers the most common listener questions that could upend your year-end tax plans. From changes inside the Big Beautiful Bill to updated incentives like bonus depreciation, R&D credits, and SALT strategies, Jeff breaks down what’s new for 2025 and what you can still act on before December 31. He also explains the difference between investment risk and audit risk,...

It’s that time of year — not the holidays, but tax planning season. In this episode, Jeff Trapp breaks down what the ongoing IRS shutdown means for taxpayers, from refund delays to suspended audits and limited online services. He also cuts through the noise to share real-world, last-minute strategies that individuals and business owners can still use before the end of the year to save significantl...

2025 is almost over, but there’s still time to legally cut your tax bill. In this episode, Jeff Trapp shares six powerful year-end strategies—from bonus depreciation and R&D credits to real estate, retirement, and income timing that can help you keep more of what you earn. If you’re an entrepreneur, investor, or high-income earner, these tips will help you discover how true tax planning can he...

Making millions in revenue but still feeling broke? In this episode, Jeff Trapp breaks down a common trap high-earning business owners fall into: chasing top-line sales while ignoring what really matters — profitability. Learn the 5 hidden profit levers that can dramatically boost your take-home pay without adding more revenue. From pricing strategy tweaks to cutting silent cost killers, Jeff shar...

Now that the One Big Beautiful Bill has officially passed on July 4th, the tax landscape just shifted—big time. In this episode, Jeff unpacks what’s really in the new law, from permanent increases to the standard deduction and child tax credit to massive wins for business owners like 100% bonus depreciation and a nearly doubled Section 179 cap. You’ll also hear what’s being phased out, which strat...

The Senate just released its version of the sweeping new tax bill—and it’s packed with changes that could reshape your tax strategy for 2025 and beyond. In this episode, Jeff Trapp breaks down the most important updates and what business owners and high earners need to know now. Jeff covers proposed changes to the standard deduction and senior bonus amounts, surprising moves on the SALT cap and pa...

A sweeping 389-page tax proposal is on the table—one that could significantly impact the planning strategies of business owners, investors, and high-income earners. In this episode of The Jeff Trapp Podcast , Jeff breaks down the newly expanded “One, Big, Beautiful Bill”—from the new 23% 199A deduction to proposed MAGA accounts and the extended IRS audit window. 💡 Key takeaways include: What’s ch...

Thinking about investing in real estate to lower your tax bill? Not so fast. In this episode, Jeff Trapp of the Jeff Trapp Podcast breaks down a common misconception about real estate professional status and why it won’t automatically free up your old passive losses. Jeff also shares key tax planning reminders for 2025, what’s happening with tariffs and the economy, and how to stay focused on buil...

In this episode of the Jeff Trapp Podcast, Jeff dives deep into the essentials of real estate investing and crucial IRS rules you must understand to maximize your tax deductions. Whether you're an active investor managing properties hands-on, or passively investing through syndications, funds, or REITs, Jeff breaks down the differences clearly and concisely. Learn how to qualify as a Real Esta...

In this episode of The Jeff Trapp Podcast , we dive into the latest tax proposals under the Trump administration and what they could mean for you. With the first 100 days underway, major topics include the push for no taxes on tips, Social Security, and overtime pay, as well as the potential extension of the 2017 tax cuts. Jeff shares his insights on the likelihood of these changes passing and how...

Happy New Year! In this episode of The Jeff Trapp Podcast, Jeff kicks off 2025 with key tax updates, including filing extensions for disaster-affected areas, the latest on beneficial ownership reporting, and crucial deadlines for the upcoming tax season. If you’ve been affected by recent disasters in California or North Carolina, be sure to check out the IRS disaster relief updates at irs.gov/news...

In this special December episode of The Jeff Trapp Podcast , Jeff wraps up 2024 with essential year-end tax planning strategies. As the holidays approach, discover how to turn ordinary business expenses into extraordinary tax savings, leaving you with extra cash to make this season even more special. From prepaying business expenses and leveraging Section 179 deductions to buying equipment or vehi...

In this episode of The Jeff Trapp Podcast, Jeff talks about the historic election of Donald Trump as the 47th President of the United States and its implications for tax policies. He discusses potential extensions to the Tax Cuts and Jobs Act and other key tax code provisions, as well as proposed changes requiring Congressional approval. Jeff emphasizes the importance of proactive tax planning and...

In this episode of The Jeff Trapp Podcast , Jeff dives into the heart of tax planning season, offering actionable strategies to maximize your year-end savings. With the 2024 tax season quickly approaching, Jeff shares insights on essential moves you can make now to reduce your tax liability before the year ends. Whether you're a business owner, investor, or high-income earner, this episode provide...

In this episode of The Jeff Trapp Podcast , Jeff kicks things off with a brief update about the future of the show and some exciting developments at The Tax Planning Pros. But the main focus of today's episode is an in-depth look at the latest tax and economic plans from Kamala Harris and Donald Trump. We’ll objectively analyze Harris’s proposals, including her plans for affordable housing, ta...

In this episode of The Jeff Trapp Podcast , Jeff explains everything you need to know about the Beneficial Ownership Information Report, a new requirement from the Financial Crimes Enforcement Network (FinCEN). If you own an LLC, corporation, or partnership, you could face daily fines of $500 or even prison time for non-compliance. Jeff breaks down who needs to file, when to file, and the steps to...

In this episode of The Jeff Trapp Podcast , the focus of today's discussion is cost segregation—a powerful tool for real estate investors. Whether you own long-term rentals, Airbnb properties, or commercial real estate, cost segregation can help you accelerate depreciation and unlock significant tax deductions. Jeff breaks down how and when to implement this strategy, addresses passive loss ru...

In today’s episode of The Jeff Trapp Podcast, Jeff breaks down Vice President Kamala Harris’s new tax plan, highlighting potential changes that could impact both wealthy individuals and business owners. From proposed tax rate increases to estate tax revisions, Jeff explores how these policies might affect your financial planning and what steps you can take to protect your wealth. If you’re serious...