In this episode of The Investor's Guide to Joy, host Paul Graham sits down with Bob Boeshaar to tackle the often-daunting topic of taxes. Bob shares invaluable insights on navigating tax challenges, including how to avoid common pitfalls like poor recordkeeping and hobby losses, and provides practical tips for business owners, investors, and individuals facing audits or back taxes. The discussion highlights strategies for staying compliant, leveraging tax laws, and understanding your options for resolving tax debt, ensuring you can focus on achieving financial success and joy.

Whether you're a seasoned investor, a small business owner, or someone simply looking to better understand the IRS, this episode delivers actionable advice and key takeaways. From managing payroll taxes to addressing liens on properties and businesses, Bob’s expert guidance empowers listeners to approach taxes with confidence and clarity. Don’t miss this opportunity to demystify taxes and learn how to turn them into a tool for financial growth.

Highlights of the Podcast

00:07 - Introduction to Taxes and Joy

03:03 - Meet Bob Boeshaar

04:07 - Why People Don't Pay Taxes

07:59 - Audits and Recordkeeping

09:19 - Hobby Losses vs. Business Losses

18:35 - Types of Audits

27:12 - Liens and Asset Management

34:06 - Options for Tax Debt Resolution

37:03 - Key Takeaways for Investors

39:31 - Final Thoughts