Paper Trails

Possible Ways to Avoid Taxes Legally

Small Business Big World Episode 11: Legal Tax Avoidance – An interview with Joshua Holt from Steward Partners

This is Small Business Big World, our weekly podcast prepared by the team at Paper Trails. Owning and running a small business is hard. Each week we’ll dive into the challenges, headaches, trends, fun and excitement of running a small business. After all, small businesses are the heartbeat of America and our team is here to keep them beating.


Watch the full episode here.

Listen to the full episode here.


Running a small business is like juggling multiple balls at once. You have to keep your customers happy, manage your team, and make sure the finances are in order. One of the biggest headaches for small business owners is figuring out how to handle taxes. It can feel overwhelming and confusing, and the fear of making a mistake looms large. But don’t worry—there are some potential legal ways to avoid paying more tax than you need to, and understanding these strategies can help secure your business’s future.

In this article, you’ll learn about some possible methods of legal tax avoidance for your small business. We’ll break down complex ideas into simple terms, covering everything from the importance of having a good advisory team to specific tax strategies. Please be sure to ALWAYS seek legal guidance when making any decisions when it comes to tax decisions.  At Paper Trails, we’re passionate about helping small businesses overcome their payroll, HR, and management challenges. Our goal is to inform and educate you, so you can focus on what you do best—running your business.

In this episode, we are joined by Joshua Holt from Steward Partners to discuss the interesting topic of legal tax avoidance.

Why You Need Professional Advice for Legal Tax Avoidance

Navigating tax laws can be tricky. That’s why having a reliable team of professionals, including an accountant, a wealth manager, an attorney, and business consultants, is crucial. In our podcast episode “Legal Tax Avoidance,” Josh Holt emphasizes how a strong advisory team can transform the daunting task of financial planning into something manageable and even beneficial.

How a Team Can Help You Save Money

A good advisory team helps you make informed decisions, ensuring you take advantage of all possible tax benefits. They can guide you through the complexities of tax laws, helping you to avoid costly mistakes. The cost of professional advice is often outweighed by the long-term savings and peace of mind you gain from knowing your finances are in expert hands.

Real Estate and Legal Tax Avoidance

Owning real estate can be a smart way to build wealth and reduce your tax burden. Josh Holt discusses how engaging with a professional team can help you manage risks and maximize tax benefits from real estate investments. Regular consultations with your accountant ensure you’re making timely decisions that bolster your financial strategies and enhance your investment returns.

Qualified Charitable Distributions

Another strategy we discussed in the podcast is using qualified charitable distributions. This allows you to support your favorite causes while optimizing your tax situation. By donating directly from your retirement accounts, you can reduce your taxable income and make a positive impact.

Retirement Planning and Tax Efficiency

Planning for retirement is a crucial part of financial management. In this podcast episode, Josh highlights various investment options available to business owners, including cash balance plans and Employee Stock Ownership Plans (ESOPs). These plans not only help secure your future but also offer significant tax advantages.

Tax Loss Harvesting

Tax loss harvesting is another effective strategy for legal tax avoidance. It involves selling investments at a loss to offset gains in other areas, reducing your overall tax liability. The recent legislative updates, like Secure 2.0, offer new opportunities for tax-beneficial savings, making it more important than ever to stay informed and proactive.

The Impact of Alternative Minimum Tax (AMT)

For those invested in municipal securities, understanding the impact of the alternative minimum tax (AMT) is essential. Josh delves into the nuances of bond taxation, highlighting how legislative changes can affect the marketability of tax-exempt securities. Being aware of these subtleties can help you make well-informed decisions and avoid unexpected tax hits.

Staying Informed on Legislative Changes

Tax laws are always evolving, and staying updated on these changes is crucial for effective tax planning. Our podcast episode serves as a reminder of the importance of continuous learning and consulting with professionals who keep up with these updates.


Legal tax avoidance is not about evading taxes but about being smart and strategic with your financial decisions. Our podcast episode with Joshua Holt is a treasure trove of insights and practical advice for small business owners. By understanding and applying these strategies, you can secure your financial future and focus on growing your business.

At Paper Trails, we are dedicated to assisting small businesses through their payroll, HR, and management challenges. We believe that with the right guidance and strategic planning, financial independence is not just a dream but a realistic goal. Absorb these insights, apply them, and ensure your financial future is as secure and prosperous as your business.

Remember, the key to successful financial management is not just working hard but also working smart. Legal tax avoidance strategies are tools that can help you achieve that, providing peace of mind and a solid foundation for your business’s growth.

This podcast is a production of Paper Trails. We are a payroll and HR company based in Kennebunk, Maine, and we serve small and mid-sized businesses across New England and the country. If you found this podcast helpful, don’t forget to follow us at at Paper Trails Payroll across all social media platforms and check us out at for more information. As a reminder, the views, opinions and thoughts expressed by the hosts and guests alone. The material presented in this podcast is for general information purposes only and should not be considered legal or financial advice. By inviting this guest to our podcast, Paper Trails does not imply endorsement of or opposition to any specific individual, organization, product or service.