Christopher K. Winn

Chris has been providing holistic tax and wealth management advice to his busy clients for more than 20 years. He operates on a simple philosophy: help people achieve more out of life. Professionally, that means giving his clients more time to focus on the things they love and helping them achieve their goals faster through his holistic tax and wealth management services.

Mr. Winn has been quoted in TheStreet.com’s sister magazine MainStreet, a featured Fee-only financial advisor in Kiplinger’s “Jumpstart Your Retirement” and given numerous presentations to a wide range of groups from the Oregon Trial Lawyers Association to Intel.

Chris enjoys golfing, wood working, cooking and chasing his Great Dane around the neighborhood.

Professional Associations

> Estate Planning Council of Portland
> World Future Society

Author's articles

How Realistic Is Early Retirement With Financial Independence?

The dream of early retirement often paints pictures of global escapades, embracing personal passions, or simply savoring the joys of life without the daily grind. But how attainable is this goal, particularly when desiring a cushion of financial independence? Here’s some hopeful news: In the U.S., while the traditional retirement age hovers around 65, a…

Author
Christopher K. Winn
Sep, 24 2023 · Financial Planning
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IRA Savings vs. IRA Investments – A Comprehensive Guide

By mid-2022, over 40% of US households had already recognized the value of Individual Retirement Accounts (IRAs) in their financial planning. Thinking of joining them? You might position yourself for a more secure retirement. One of the big perks of IRAs is their attractive tax breaks that can help your savings grow. But remember, not…

Author
Christopher K. Winn
Sep, 24 2023 · Investment Management
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Navigating the Retirement Paradox: The Fear of Tapping into Savings

Retirement is a cherished milestone marking the end of decades of work and preparation. Yet, it comes with a psychological challenge — the reluctance to spend hard-earned savings.  According to research conducted with the Employee Benefit Research Institute (EBRI), most current retirees still have 80% of their pre-retirement savings after almost two decades. This means,…

Author
Christopher K. Winn
Aug, 29 2023 · Financial Planning
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Taxes in Oregon for Small Business: The Basics

Located in the scenic Pacific Northwest, Oregon is celebrated not only for its breathtaking landscapes but also as a haven for businesses. Boasting over 396,925 small enterprises, this state has firmly established itself as a premier destination for business in the U.S. However, if you’re an entrepreneur eyeing Oregon as your business hub, it’s essential…

Author
Christopher K. Winn
Aug, 29 2023 · Business Owner Planning
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Navigating the Age Landscape: When to Open an IRA

Planning for retirement with an Individual Retirement Account (IRA) is all about timing. The sooner you begin, the better positioned you’ll be for a financially secure future. But are there age limits on Roth IRAs? At what age can you open a Roth IRA? What retirement account options will best serve your goal? Well, stay…

Author
Christopher K. Winn
Aug, 29 2023 · Financial Planning
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The Four Types of Individual Retirement Accounts (IRAs)

Individual Retirement Accounts (IRAs) are attracting unprecedented interest. As of the first quarter of 2023, the total assets held in IRAs soared to an impressive $12.5 trillion, marking a 4.3 percent increase from the previous quarter.

Author
Christopher K. Winn
Jul, 25 2023 · Financial Planning
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6 Rules for Successful Dividend Investing: Maximizing Returns and Building Passive Income

Dividend investing is a popular wealth accumulation strategy for many Americans, with trusted insights revealing that the investment vehicle has maintained an average payout ratio of 56.3% over the last 96 years.

Author
Christopher K. Winn
Jul, 25 2023 · Financial Planning
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Unlocking the Power of IRA: Building Wealth, Securing Your Future

Individual Retirement Accounts (IRAs) are a popular investment vehicle for self-employed individuals or working folks who don’t benefit from employer-sponsored plans. This strategy allows you to start saving for your golden years as early as possible and accumulate enough to foster financial independence when retirement comes.

Author
Christopher K. Winn
Jun, 23 2023 · Fiduciary Financial Planning & Wealth Management
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How Does an IRA Generate Income and Grow Your Money?

Individual retirement accounts are reliable vehicles for accumulating funds over time. They foster substantial growth through tax-free earnings on investments and play a significant role in long-term financial planning. Unfortunately, not many people understand how this individual retirement arrangement works. In fact, according to a 2020 survey by The American College of Financial Services, about 80%…

Author
Christopher K. Winn
Jun, 22 2023 · Fiduciary Financial Planning & Wealth Management
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A Guide to Restricted Stock Units (RSUs): What They Are and How to Maximize Their Value?

RSUs are used by many companies to reward and retain employees. Explore key considerations to help you make informed decisions about your Restricted Stock Units.

Author
Christopher K. Winn
May, 23 2023 · Business Owner Planning
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