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

In this episode of The Investor's Guide to Joy, Tino Madyara, a seasoned tax professional and real estate investor, shares expert advice on tax strategies for business owners and investors. He highlights the importance of aligning personal and business tax plans to maximize savings, avoid surprises, and navigate complex tax structures. Tino also offers a success story where proactive tax planning saved a business $500,000 during an acquisition, demonstrating the power of strategic decisions in tax management.

Tino Madyara discusses common pitfalls in real estate partnerships, particularly around tax structures and depreciation, and stresses the need for business owners to work closely with a tax professional. Reflecting on his own real estate journey, he encourages investors to find a strategy that aligns with their personal values and long-term goals. This episode provides actionable insights into tax planning, real estate investing, and making informed decisions for financial success.

Highlights of the Podcast

00:08 - Introduction

02:40 - Business Owners' vs. Individuals' Tax Strategies

04:14 - Challenges for Smaller Businesses

07:50 - Success Story: Tax Savings in Acquisitions

09:50 - Advice for Business Owners

12:59 - Real Estate Partnerships and Common Mistakes

15:10 - Working with a Tax Professional

22:26 - Timeline for tax planning

23:50 - Choosing the right tax professional

25:17 - Tino’s real estate investment journey

30:05 - Due diligence and market risks

32:40 - Mindset for investors

In this episode of The Investor's Guide to Joy, Paul Graham and Christion Sadler dive into the secondary real estate market, exploring how it provides investors with the opportunity to unlock equity before the typical 3-5 year lockup period. Christion explains how the Pre-iShare platform facilitates these transactions, offering a marketplace where buyers and sellers can connect. He shares insights into why liquidity is important for investors, whether due to life events or portfolio adjustments, and discusses the challenges of pricing and due diligence in secondary market transactions.

The conversation also delves into the creative possibilities within the secondary market, including structuring deals and negotiating terms, as well as the importance of being an accredited investor. Christion emphasizes the need for transparency, thorough communication, and understanding the risks and opportunities involved. With a focus on secondary market investments, he offers valuable advice on how investors can navigate this evolving space to unlock potential upside and achieve long-term success.

Highlights of the Podcast

00:07 - Introduction

02:32 - Christion's Role & Investor Profiles

04:25 - Investor Situations & Liquidity Needs

07:38 - The Need for a Secondary Market in Real Estate

12:24 - Due Diligence & Market Confidence

13:45 - Valuation & Pricing of Secondary Market Shares

15:44 - Process, Timeline, and Costs for Secondary Sales

18:30 - Buying and Selling Secondary Market Shares

19:16 - Due Diligence in Secondary Market Investing

22:39 - Benefits of Vintage Investing

25:27 - Types of Real Estate on the Platform

27:55 - Negotiating Secondary Market Transactions

32:43 - Accredited vs. Non-Accredited Investors

34:08 - Accredited Investor Status

35:41 - Secondary Market Benefits

39:08 - Preacher Liquidity Fund

41:45 - Operational Risks

45:18 - Personal Investment Advice