The Jeff Trapp Podcast

Hosted by Jeff Trapp

Business

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Episodes

144

Latest episode

Oct 2026

Language

EN-US

About the show

Jeff Trapp is a Tax Strategist who has created 3 different companies and helped entrepreneurs save millions of dollars on taxes through strategic tax planning. In this podcast, Jeff will share tax tips, his knowledge of business, and financial strategies.

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60 recent

October 14, 202610 min

Stop Chasing Tax Deductions. Do This Instead.

The Augusta Rule. Bonus depreciation. Maxing out your 401(k). These are some of the most talked-about tax strategies, especially as year-end approaches. But are they really where your tax planning should begin? In this episode of The Jeff Trapp Podcast, Jeff explains why chasing individual deductions can mean overlooking bigger opportunities. He breaks down five key areas high-income business owners and investors should evaluate, including income sources, business structure, retirement planning, timing, and the ability to utilize tax losses. Discover why effective tax planning isn't about collecting deductions. It's about making strategic financial decisions that work together to reduce tax liability and build long-term wealth. Learn more or schedule a complimentary tax strategy review: https://www.thetaxplanningpros.com/contact-us#BookAConsultation For educational purposes only. This is not tax, legal, accounting, or investment advice. Consult a qualified professional for guidance specific to your situation.

September 16, 202610 min

The Tax Moves You’ll Wish You Made Before December

One of the biggest tax planning mistakes I see profitable business owners make has nothing to do with choosing the wrong strategy. It’s waiting too long to start planning. By the time you know exactly what you owe, many of the decisions that could have changed the outcome may already be behind you. In this episode, I break down why proactive tax planning should start with a clear year-end projection: Where is your business actually headed? What is your expected tax liability? And, most importantly, what decisions can you still make while you have time to make them thoughtfully? I also discuss why good planning isn’t about chasing deductions or forcing strategies to fit. It’s about understanding the full financial picture, evaluating which opportunities actually support your goals, and giving yourself enough time to implement them correctly. Tax preparation tells you what happened. Tax planning is about making informed decisions while you still have choices. For profitable business owners, that distinction can make all the difference.

August 12, 202610 min

Microsoft Paid 2.44% in Federal Tax... So What Do They Know That You Don't?

Microsoft reportedly paid just 2.44% in current federal income taxes. Is that tax avoidance, or simply understanding how the tax code works? In this episode, Jeff breaks down what that headline actually means, the difference between tax avoidance and tax evasion, and why Congress intentionally creates tax incentives for businesses. More importantly, you'll learn the lesson business owners can take from Fortune 100 companies: tax preparation records historical data; tax planning changes the future. If billion-dollar companies have tax professionals working on strategy year-round, why are so many business owners only talking to their CPA once a year? 📞 Schedule a complimentary tax strategy review: https://www.thetaxplanningpros.com/contact-us#BookAConsultation 🌐 www.thetaxplanningpros.com

July 15, 202611 min

The Tax Evolution: Building Wealth by Design

Most business owners assume that having a great CPA means they're paying the lowest amount of tax possible. The truth is, tax preparation and tax planning are not the same thing. In this episode, Jeff Trapp introduces The Tax Evolution, a framework that shows how tax advice can go far beyond filing returns. He walks through the journey from compliance and planning to long-term strategy and wealth building, explaining why the biggest tax-saving opportunities happen before major financial decisions are made. If you're a business owner or high-income professional, this conversation will change the way you think about taxes and show why building wealth starts with making better decisions throughout the year, not just during tax season. If you found this episode valuable, be sure to Like, Share, and Subscribe so you never miss future conversations on proactive tax planning, wealth building, and smarter financial decision-making. And if you're a business owner or high-income professional wondering whether you're leaving money on the table, we'd love to talk. Visit https://www.thetaxplanningpros.com/contact-us#BookAConsultation to schedule a consultation with a member of our tax team. We'll help you determine whether proactive tax planning could make a meaningful difference for your unique situation. Remember, the biggest tax-saving opportunities often happen before the biggest financial decisions are made. Thanks for watching, and we'll see you in the next episode.

June 10, 202611 min

Summer Tax Savings You'll Miss by December

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 owners, entrepreneurs, and real estate investors should be considering right now, including hiring your kids, Roth IRA opportunities, business travel deductions, conferences and networking events, mileage tracking, and more. We also discuss why waiting until year-end to think about taxes can be one of the most expensive mistakes a business owner makes. If you're looking for ways to be proactive, reduce your tax burden, and take advantage of opportunities before they disappear, this episode is for you. The best tax planning doesn't happen at year-end. It happens long before year-end.

May 13, 20266 min

Your Tax Strategy Failed Before the Year Even Ended

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 a client who unknowingly paid taxes on over $200,000 that should have been deducted, and how we helped recover $74,000 by fixing the underlying data. We also get into the difference between bookkeeping, accounting, and tax strategy, and why most business owners are paying for one but expecting all three. If your numbers aren’t clean, your strategy doesn’t stand a chance. If you’re not confident in your financials or you’ve never had someone actually review your numbers from a strategy perspective, that’s where this starts. If you want a second set of eyes on your situation, you can book a consultation here: https://www.thetaxplanningpros.com/contact-us#BookAConsultation

April 15, 202610 min

The Missing Piece in your TikTok Tax Strategy

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 treat taxes like an event instead of a year-round process. That one mindset alone is costing people thousands, sometimes millions. We also talk about the explosion of tax advice on TikTok and AI, what’s useful, what’s misleading, and why strategy without proper implementation can backfire.

March 18, 202613 min

The Tax Code Secret High-Income W-2 Earners Miss

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 into how to think differently about taxes by aligning with the areas the government incentivizes, including business ownership, real estate, energy, and long-term planning. If you are earning strong income but not keeping as much as you should, this episode will help you start approaching taxes with a strategy instead of reacting to them. If this episode shifts how you think about taxes, share it with someone else who needs to hear it. And if you are ready to take a more proactive approach, you can book a consultation with our team here: https://www.thetaxplanningpros.com/contact-us#BookAConsultation

February 11, 202615 min

The Most Unusual Tax Season in Years—and How to Stay Ahead

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 the last minute often pay the price. I walk through the key deadlines you need to be aware of, why filing an extension doesn’t extend the time to pay, and how inflation, interest rates, and a massive federal deficit are shaping the government’s growing need for revenue. More importantly, I reframe how taxes should be viewed altogether. The tax code is an incentive-based system, and for high earners and business owners, there are legitimate ways to redirect tax dollars into government-incentivized investments, such as real estate, energy projects, and strategic business reinvestment—while staying fully compliant. Tax season isn’t just about filing a return. It’s about strategy, planning, and being intentional long before the deadline. If you’re earning $500,000 or more and want to stop reacting to tax season and start planning proactively, you can book a consultation with my team to review your situation and explore your options. We'll even share a copy of our tax playbook: https://www.thetaxplanningpros.com/contact-us#BookAConsultation

January 21, 20269 min

Time-Sensitive 2026 Tax Updates ((And Why They Matter Now)

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 tax brackets, a higher standard deduction, and new limits for the child tax credit. I’ll break down what the IRS is doing with crypto reporting, how to handle the new 1099-DA form, and why W-2 refunds might look bigger this year. If you're a business owner, High-income W-2 earner, or just someone who wants to keep more of your money in 2026, this episode is for you. Let’s get you caught up and on track to make this your most financially strategic year yet.