How can small business owners make the most of their tax deductions? Josh continues with his small business tax series, focusing on the crucial topic of deductions and the mistakes entrepreneurs need to avoid. From home office write-offs to maximizing tax credits, he unpacks strategies to help reduce taxable income while staying compliant. Josh also highlights the importance of accurate record-keeping and shares practical tips to simplify tax prep and sidestep common errors.

Then in 'Extra Points,' the team discusses Taylor Swift’s Eras Tour and its surprising impact on small businesses, sparking a debate about the intersection of culture and commerce.

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What’s your best defense against the IRS? Josh brings back renowned tax litigation expert Dan Pilla to uncover strategies for navigating today’s complex tax landscape. As the head of Pilla Tax and author of 14 books on tax-related issues, Dan shares his decades of experience fighting and winning cases against the IRS. Together, they dive into expiring provisions of the Tax Cuts and Jobs Act, rising IRS audits, and how small business owners and individuals can protect themselves with proper documentation and smart planning.

Josh and Dan break down home office and mileage deductions, year-end tax-saving strategies, and common pitfalls that could trigger IRS scrutiny. They also explore how to navigate disputes with the IRS, from wage levies to appeals, and the importance of staying proactive with your tax strategy.

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How should small business owners navigate the maze of taxes? It's tax prep month on The Financial Quarterback Podcast, and Josh begins by laying out the groundwork for small business tax management. From picking the right structure—LLC or S Corp—to the critical role of keeping accurate records, he unpacks what entrepreneurs need to know before deductions and strategies take center stage in the next episode. Along the way, Josh explores key tax categories like income and self-employment taxes and emphasizes the value of hiring a trustworthy financial team to avoid costly mistakes.

Then in 'Extra Points,' Josh shares his thoughts on Netflix’s decision to build a $900 million studio in New Jersey. What does this mean for small businesses in the area? And how do these massive tax breaks stack up against what everyday entrepreneurs face?

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What’s the cost of procrastinating on your taxes? Josh explores this with CPA, attorney, and financial strategist Mark J. Kohler, host of The Main Street Business Podcast. Known for helping entrepreneurs and families navigate tax, legal, and wealth-building strategies, Mark breaks down actionable tips like leveraging S Corporations, family board meetings, and Roth IRAs for kids, while sharing his expertise on year-end tax moves and financial planning essentials.

Together, Josh and Mark dig into why S Corporations can be a game-changer for cutting self-employment taxes, how to turn family board meetings into tax deductions, and ways to use Roth IRAs for your kids to save now and build their financial future. The two also cover year-end moves like buying vehicles or equipment for bonus depreciation, leveraging HSAs for tax benefits, and making sense of crypto taxation as it continues to evolve.

Check out more from Mark Kohler on his website and his educational platform for small business owners.

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What does it take to build and sustain a thriving small business in today’s economy? Josh breaks down the challenges small business owners face, from inflation and competition to tax strategies and cash flow management. Drawing from his own experience as a young entrepreneur, he lays out actionable steps to create a strong financial foundation for your business and navigate the complexities of running a company in a competitive market.

Then in 'Extra Points,' the conversation turns to Starbucks and its recent struggles in maintaining its foothold as a giant in the coffee world. Josh and the team examine what’s going wrong for the company and what small businesses can learn from their missteps.

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What’s the real cost of following mainstream financial gurus? Josh brings back bestselling author David McKnight to unpack his latest book, The Guru Gap: How America’s Financial Gurus Are Leading You Astray, and How to Get Back on Track. They dissect "advice" from popular figures like Dave Ramsey and Suze Orman, highlighting why their broad strategies might not work for everyone—and what you can do instead.

Josh and David dig into nuanced financial strategies, including Roth conversions, annuities, and life insurance, explaining how these tools can help mitigate longevity risk and take advantage of current tax laws. They also discuss how Trump-era tax cuts impact Roth planning and why personalized advice beats generic rules of thumb every time. Plus, the two bond over the joys and challenges of raising seven kids each.

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Everyone's Talking About Their 'Roman Empire'—But What Does It Mean for America's Financial Future? Josh dives into the resurgence of the Roman Empire in today's cultural zeitgeist, questioning what this fascination reveals about our own era's concerns with debt, inflation, and the potential decline of the American empire. He draws parallels between ancient Rome's fall and the current fiscal challenges facing the United States, such as unsustainable debts and the erosion of international trust, which could threaten its status as a global superpower. Josh also examines the rise of digital currencies like Bitcoin as modern society's response to traditional currency manipulation.

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Are taxpayer-funded sports stadiums a financial blessing or a burden? Josh dives into this hot-button issue, exploring the true economic impact and cultural significance of iconic arenas like Yankee Stadium and Fenway Park. He scrutinizes whether these massive public expenditures truly benefit the communities they claim to uplift, or if they merely line the pockets of billionaire team owners. From Milwaukee to Buffalo, Josh breaks down the promises of job creation and neighborhood revitalization, challenging the role of politicians in facilitating corporate welfare.

Plus, in "Extra Points," Josh and his team debate the practicality of Ubering versus driving to a game and explore how stadium naming rights play into the larger financial picture.

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Are you ready to draft the ultimate financial strategy? Josh kicks off this episode by breaking down how to build a well-rounded financial team, focusing on diversification and managing risk. He guides you through the importance of balancing offensive and defensive investments, ensuring that your portfolio is set up for long-term success, especially as retirement approaches.

Then, it’s draft day! In the second half of the episode, Josh teams up with Producers Jim and Fisher to dive into the 2024 Financial Draft. Together, they compete to select the best financial assets—picking everything from stocks and bonds to alternative investments—as they each build their own dream portfolios. It's a high-stakes financial showdown, where the goal is to craft a winning strategy for future wealth and retirement security.

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The Island of Misfit Toys is taking over the Financial Quarterback! Josh and the studio team—his self-proclaimed band of misfits—dive into Christmas and Hanukkah spending, gift-giving, and the surprising financial lessons behind the season. With Josh leading the pack like Rudolph, they break down how to balance budgets, navigate the quirks of family traditions, and find value in what truly matters. It’s a fun and spirited take on the most wonderful (and expensive) time of the year!

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