Wall Street Secrets for Tax-Efficient Investing: From Tax Pain to Investment Gain

Table of Contents viii

List of Illustrations xv

Preface xvi

Overview 1

Part 1: Taxable Investments and Strategies for Protecting Their Value

1 Choosing your Investment Tools Carefully 13

2 The How and When of Harvesting Your Losses 27

3 Techniques for Utilizing your Losses 39

4 Smart Choices for Fixed-Income Holdings 47

5 Hedging to Avoid Capital Gains Tax 55

6 The Quest for Tax Efficiency in Mutual Funds 75

Part 2: Tax-Advantaged Investment Opportunities

7 Structuring Your Retirement Portfolio 95

8 Savvy Ways to Save for College 113

9 The Double Life of Life Insurance 129

Part 3: Special Situations

10 Making Prudent Elections 143

11 Managing Your Employee Stock Options 157

12 Avoiding Tax Traps for Closely Held Businesses 167

13 Planning for Often-Overlooked State Taxes 177

Part 4 Your Annual Opportunity

14 Year-End Planning Strategies 201

Appendix 1: Historical Tax Rates 217

Appendix 2: Key Points for Investors from the 2001 Tax Act 221

Notes 227

Glossary 229

Index 250