Wall Street Secrets for Tax-Efficient Investing

Author: Robert N. Gordon with Jan M. Rosen
Price: $31.50


When looking at a monthly brokerage statement, an investor’s eyes go straight to the bottom line—the account value. But there’s a catch. If you have big gains and decide to play it safe and take some of that money off the table, taxes will take a hefty chunk of those profits. Brokerage firms know how to handle such risk for their own accounts, hedging holdings, for example, to iron out volatility instead of incurring taxable capital gains. Savvy individual investors can use the same techniques to protect themselves. In this indispensable guide, Robert Gordon, a Wall Street veteran, shares the strategies of an insider to demonstrate how you can use the tax laws to your advantage. Written in plain English, this book explains federal and state tax considerations that investors need to know to make the most tax-efficient choices and to protect their portfolios. The emphasis is on practical application, aimed at guiding you to specific, accessible tax-saving goals without having to wrestle down the entire Internal Revenue Code. Thanks to the talents of Gordon and respected journalist Jan M. Rosen, this book is clearly organized along transactional lines, offering easy entry for busy readers and allowing investors to zero in on a powerful array of proven, tax-minimizing techniques and strategies. By the time you finish reading Wall Street Secrets for Tax-Efficient Investing, you will be on your way to reducing your tax bite to a nibble and enjoying the full benefit of your investment earnings.

Author Biography

Robert N. Gordon is the president and owner of Twenty-First Securities Corporation, which provides investment advice and financial management for corporate, institutional, and individual clients. He was formerly a partner at Oppenheimer & Company and chairman of the Securities Industry Associations Tax Policy Committee. He is also an adjunct professor at New York Universitys Graduate School of Business and is a much sought-after speaker at industry conferences.

Jan M. Rosen, a long-time editor and former tax columnist in the financial news department of The New York Times, has been responsible for that newspapers annual tax section for many years. In addition, she is a contributor to Tax Hotline and other newsletters published by Boardroom, Inc.

Table of Contents


PART 1: Taxable Investments and Strategies for Protecting their Value.
Choosing Your Investment Tools Carefully.
The How and When of Harvesting Your Losses.
Techniques for Utilizing Your Losses.
Smart Choices for Fixed-Income Holdings.
Hedging to Avoid Capital Gains Tax.
The Quest for Tax Efficiency in Mutual Funds.
PART 2: Tax-Advantaged Investment Opportunities.

Structuring Your Retirement Portfolio.
Savvy Ways to Save for College.
The Double Life of Life Insurance.
PART 3: Special Situations.

Making Prudent Elections.
Managing Your Employee Stock Options.
Avoiding Tax Traps for Closely Held Businesses.
Planning for Often-Overlooked State Taxes.
PART 4: Your Annual Opportunity.

Year-End Planning Strategies.

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