The Latest News From Oak Street Investments

By Jacob Milder, CFP®, ChFC® | Jan 30, 2024

In my 3rd quarter newsletter for 2022, I mentioned that models from Bloomberg Economics put the odds of a recession within one year at nearly 100%.  I’m not much of a gambler, but I believe those are good odds. Oops. 2023 ended the year with a bang!  No, that doesn’t mean the economy was exceptionally…

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Chaos and Bloodshed

By Jacob Milder, CFP®, ChFC® | Oct 27, 2023

Staying disciplined and invested can be difficult in times of chaos and market turbulence. History tells us this is the right time not to act.

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1Q2023 – AIn’t (Quite) Ready for Prime Time

By Jacob Milder, CFP®, ChFC® | May 3, 2023

Please excuse the delay in this quarterly newsletter, I was watching Tucker Carlson and Don Lemon…get canned.  Too soon?  Don’t worry, this quarter’s post isn’t about the rise and fall of the prime time television elite: it’s about the rise of AI tools in our everyday life.  In a flash of brilliance (or laziness), I…

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2022AMR

2022 Annual Review – Everything Will Be Okay

By Jacob Milder, CFP®, ChFC® | Jan 24, 2023

Ouch.  Let me be the first to admit I thought we had another six months to a year before the markets woke up from their years-long drunken (on easy money) binge.  After all, 2022 began the year with a strong labor market, easy money and record low interest rates, and Elon Musk still wealthy (I…

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green shoots

Green Shoots Amid the Economic Rubble

By Jacob Milder, CFP®, ChFC® | Oct 19, 2022

My apologies for the delay in getting this 3rd quarter review out. I was busy combing through the financial rubble that is the global economy for some glimmer of hope, and it turns out there are some sprouts beginning to grow.  But first, the storm.    For the 3rd quarter, US markets were off 4.46%, with…

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Kevin Bacon and Sidelined Cash – 2Q2022

By Jacob Milder, CFP®, ChFC® | Jul 14, 2022

As 80s heartthrob, loose-footed, and distant-relative-to-all Kevin Bacon asked in the classic 1978 comedy Animal House (based on Harold Ramis’ experience at my alma mater WashU), “Thank you, sir, may I have another?”  After a difficult 1st quarter, the US markets delivered another blow to investor portfolios, ending the first half of the year down…

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Predictions, Money and Mattresses

By Jacob Milder, CFP®, ChFC® | Apr 15, 2022

I don’t usually make short-term market guesses – my crystal ball has been in the shop for almost 20 years; at this point I can’t remember if it was cracked or just fogged. I believe in the power of long-term markets, good diversification and poor performance as a result of short-term market prognosticating. 

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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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