Thoughts Before the (Next) Bear Market 🧸


Good morning!

Scenes of summer here in Upstate NY. Our elder daughter loves to swim.

It's hard to go wrong with a pool + a grilled cheese sandwich.

Today's email includes:

🧸 Some thoughts before the (next) bear market.

🫙 What you might be missing on your investment account statements.

👀 Some interesting news about what the IRS is paying attention to

...and more=


Jesse on Some Other Podcasts...

Many thanks to Paul Lambert and Chris Hill and Joe Saul-Sehy for inviting me on their excellent podcasts over recent weeks...

Jesse on Paul Lambert's

FiLighter

Jesse on Chris Hill's

Money Unplugged

Jesse on Joe's

Stacking Benjamins


Thoughts Before the (Next) Bear Market

A quaint ~15 months ago, the global stock market rippled with the "tariff tantrum."

President Trump snipped and snapped over tariffs for a few weeks, and we all watched our portfolios dip and dive and recover and dive again.

I wrote the following blog post on April 8, 2025 - about one week into the tariff tantrum.

Now that our portfolios are in a state of "calm" (knock on wood) - I'd encourage you to go back and read through these mid-crash thoughts.


What You're Missing on Your Account Statements

Your monthly investment statements show what you own, how you've done, and some basic info.

But there's so much info NOT included on your statement, and that's what we're diving into today!

Investment statements tell only a fraction of your portfolio's true story, and investors who stop at account balances and performance figures may be missing some of the most important risks, costs, and planning opportunities hidden beneath the surface.


The Top 3...

I enjoyed these. I think you will too.

1) Worth remembering - the IRS pays attention to the "tax planning" that we all do.

2) Predicting the stock market vs. predicting a deck of cards.

3) An expert's thoughts on the 7 sins of active management


What Are *Your* Questions?

I love answering your questions!

My most popular podcast episodes are the "ask me anything" episodes, created using questions from people like you.

Submit your question for a future episode here:


I Help People Retire Better

I'm a Partner at a fee-only fiduciary retirement planning firm. We work with clients all over the USA.

We help answer questions like...

  • Can we retire yet?!
  • Is our portfolio invested the right way?
  • Have we saved enough?
  • How do we minimize taxes?
  • How do we plan for healthcare - especially before Medicare?!
  • ...and the list goes on!!

If you know someone who could use good help, visit PlanWithJesse.com and let's start a conversation.


Until Next Week...

Thank you for reading, listening, and writing back.

People like you send me questions every day.

I'd love to hear from you. ​​

Until next week,

Jesse Cramer

Jesse Cramer

Retirement is a different game. You’ve spent decades building wealth. Now comes the harder part - turning it into a paycheck that lasts. I’m Jesse Cramer. I help DIY investors turn their savings into a clear, cohesive retirement plan. Join 4000+ weekly readers and 20,000+ podcast listeners.

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