The Latest News From Oak Street Investments

2021 Review

Remembering the Good Times

By Jacob Milder, CFP®, ChFC® | Jan 24, 2022

It’s often said that the market takes the escalator up and the elevator down.  For concrete evidence, simply look at the performance of the indexes the past few weeks.  A close look at the headlines or nightly news (caution: this may be bad for your health and is proven to be bad for your portfolios) and you may think it’s only a matter of time before the indexes hit an all time low!  And no, that’s not really a thing!

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Dealing With Fluctuating Markets: Q3 2021 Quarterly Market Review

By Jacob Milder, CFP®, ChFC® | Nov 8, 2021

Whether you’re a long-time investor or you’re new to the market, fluctuations – and losses – can feel jarring. In fact, we know from research that losses are significantly more painful than gains of a similar size are rewarding.  Yet successful investors continue to invest because they know that over long periods of time, investing…

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grandparents 529 plan

Don’t Let Your Parents Start a 529 for your Kids

By Jacob Milder, CFP®, ChFC® | Sep 20, 2021

If you have parents who are offering to help you with college planning for your kids…lucky you! With college tuition increasing 7-8% every year, most of us can use all the help we can get. However, there is a right way and a wrong way to accept this assistance. While your parents might want to…

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tech professional financial planning

If You’re Doing This, You Might Not Get the Financial Results You Want

By Jacob Milder, CFP®, ChFC® | Jul 7, 2021

As someone who works in the tech industry, chances are you’re going to relate to the scenario I’m about to describe.   Someone walks into your office and says, “I’ve been wondering about _____, so I Googled it and now I think I can do it on my own, but I’m not quite sure.”  …

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tech professional financial planner

What Makes Financial Planning for Tech Professionals Different?

By Jacob Milder, CFP®, ChFC® | May 12, 2021

Almost every client who walks through my (virtual) door these days has one thing in common: they’ve realized their time is better spent doing something other than dealing with their money. Many of us hit that tipping point at some time. You can change your own oil, but that could take you five hours, so…

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2021 Q1 Quarterly Market Review

You Only Live Once: 2021 Q1 Quarterly Market Review

By Jacob Milder, CFP®, ChFC® | Apr 14, 2021

You only live once! Social media investors have banded together on unconventional platforms to drive up the prices of a handful of “meme stocks,” seemingly without traditional evaluation of investing risks and rewards. They made headlines with their “short squeeze” of GameStop (GME), and, as they garner media attention, their tactics continue. While it’s not…

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GameStop investor

Game-Stop Right There!

By Jacob Milder, CFP®, ChFC® | Apr 13, 2021

In the previous blog, GameStop, Blackberry, AMC: How “Dud” Companies are Suddenly Worth Billions, we discussed the origins of the GameStop and meme-stock fiasco. Now let’s take a look at some of the other players (read: enablers) and the possible outcomes of this type of trading.   Reddit As GameStop’s stock price was going vertical,…

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gamestop stock

GameStop, Blackberry, AMC: How “Dud” Companies are Suddenly Worth Billions

By Jacob Milder, CFP®, ChFC® | Apr 7, 2021

As shocking as the whole GameStop/Blackberry/AMC activity felt…in the world of commerce it’s actually nothing new.   Today’s investor would call this type of trading “meme stock” – “a stock that has seen an increase in volume not because of the company’s performance, but rather because of hype on social media and online forums like Reddit. For…

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bitcoin

Does Bitcoin Have a Place in Your Investment Strategy?

By Jacob Milder, CFP®, ChFC® | Feb 28, 2021

In 2013 I bought my first Bitcoin. I was a financial advisor at a not-to-be named wirehouse in Clayton, Missouri and a friend tried to explain to me what blockchain was. At the time, Bitcoin was around $50 per coin.   In 2013 I sold my first Bitcoin.   After all, how high could this…

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