Who I Am and Why I’m Here

October 19, 1987. Black Monday. I was 26, eight months into my first job as an equity analyst at a multi-billion-dollar trust company, sitting in an office full of people who were supposed to know what they were doing.

The Dow dropped 22.6% in a single day — still the largest one-day percentage decline in market history. And I watched it happen in real time: the people who were paid to see it coming, credentialed, experienced, titled, doing this for twenty years while I’d been doing it for eight months, said nothing useful. Not before. Not during. Not after.

What stuck with me wasn’t the number on the screen. It was the silence. Because I realized something that day I’ve never unlearned: sounding like you understand an investment is not the same as understanding it. Those two things can look identical right up until the moment they don’t.

I’ve spent the four decades since watching that gap show up again and again - not in trading rooms this time, but in ordinary conversations between an advisor and a client. Someone says “diversified alternative-income strategy” with total confidence, and the person across the table nods, because pushing back feels like admitting you don’t belong in the room. I’ve sat on both sides of that table. I know exactly how convincing confident language sounds, and exactly how little it sometimes means.

This newsletter, The Ward on the Street, exists to give investors a strategic framework for their thinking and their portfolios. You can find stock tips and hot takes anywhere, I give you a deeper understanding of what you should be doing.

If you want a more tactical look at investing, especially if you already pay financial advisory fees, please check out my “12 Questions To Ask Before You Invest A Dollar”. You can get your free copy at Ask Better Questions: Investments.

Thanks for reading and I hope you find something you can use - either today or in the future.

~ Ward