The Latest News From Oak Street Investments

picture about market volatility

A Note On Market Volatility

By Jacob Milder, CFP®, ChFC® | Feb 28, 2020

Surprise! Stock markets can be volatile. Ask your fee-only financial advisor to help you remain disciplined.

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Investment Performance

Evaluating Portfolio Performance – Part 1

By Jacob Milder, CFP®, ChFC® | Feb 25, 2020

This article will help you understand the risk/reward trade-offs inherent to investing, and put your portfolio performance into context so you can have a better, more informed and smoother investment experience.

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5 SECURE Act Changes

5 SECURE Act Changes…and How You May be Affected

By Jacob Milder, CFP®, ChFC® | Jan 17, 2020

In December of 2019, under the cover of darkness and impeachment hearings, some of the most significant tax legislation of the past 20 years passed in unusual bipartisan fashion: the Setting Every Community Up for Retirement Enhancement Act, or SECURE act.  The name- which undoubtedly took weeks of debate to come up with and agree upon, speaks to the purpose, though not the entirety or sweeping nature of the act; a rare legislative accomplishment for an otherwise gridlocked Washington.  While the act addresses a number of retirement chads left hanging after the Tax Cut and Jobs Act (TCJA) of 2017, it also makes changes to 529 plans, medical expense deductions, kiddie taxes and more.  The focus of the plan is clear, however, in its attempt to modernize and streamline retirement savings for Americans.

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2019 a year to remember

2019…A Year to Remember

By Jacob Milder, CFP®, ChFC® | Jan 9, 2020

As is often the case following a negative year, (the US Markets lost over 5% in 2018), 2019 was (globally) a banner year with total US Market returns over 30%, International markets over 20% and even the US and Global Bond market’s joining in the celebration with returns of over 8.5% and 7.5% respectively.   In fact, US Stocks were THE place to be in 2019; they were the tickets to Hamilton, U2 and BTS (Boomers, find the nearest Millennial and ask them) wrapped up into one beautiful gift basket!

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10 end of year actions for reducing taxes

10 End of Year Action Steps to Potentially Reduce Your Tax Burden

By Jacob Milder, CFP®, ChFC® | Dec 3, 2019

It’s the most wonderful time of the year…to take advantage of tax savings opportunities. 
As we begin the final weeks of the year, consider the following action items to potentially reduce your tax bill and improve your financial footing in 2020 and beyond. 

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bull banter snaps

When Batting .700 Isn’t Good Enough…

By Jacob Milder, CFP®, ChFC® | Oct 14, 2019

You’re smarter than the average investor, right?  You’ve done the research and despite hearing how difficult it is to predict the market’s direction over a specified period of time, you’re confident you know better than the CFAs, Ph.Ds and Quant’s building the algorithms on Wall Street.  You even understand that, by definition, if the stock market…

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computer screen of denver financial advisor Jake Milder

Riding High… 2Q2019 Review

By Jacob Milder, CFP®, ChFC® | Jul 9, 2019

The sky is falling mentality has just pushed the stock market to record highs. That the housing market is slowing, wages are stagnant-or negative in real terms, and you can get a higher return investing your money in 3-month government debt than 10 year debt (yield curve inversion) doesn’t seem to matter and the markets…

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paper markus spiske

Using Covered Calls to Generate Income and Hedge Concentrated Stock Positions

By Jacob Milder, CFP®, ChFC® | Jun 10, 2019

Deciding to sell a stock you’ve inherited or held on to for 25 or more years can be difficult and even emotional, and increasingly I find myself suggesting alternative strategies than an outright sale for the purposes of diversification. 

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Portfolio Picture

Zoom Out

By Jacob Milder, CFP®, ChFC® | May 9, 2019

“Why should I invest money in the market when it’s near all-time highs?”  – Investors, c. 2015, 2005, 1997, etc

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