Outsiders' Corner

Outsiders' Corner

Inside the Corner - July 2025

Reflections on Position Sizing and doubling Down on Winners

Ole's avatar
Ole
Jul 18, 2025
∙ Paid

The photo below was taken during my holiday this week in the Norwegian mountains - my favorite place to run, relax, and reflect. We all have our own approach to investing, but for me, stepping away from the noise is what helps me think for myself.

But during one of these runs, I realized a mistake I’ve made. It’s about diversifying my focus, spending to much time on new ideas, and position sizing wrongly. Not one that has necessarily cost money directly—but one that may have an indirect impact over time, through opportunity cost.

That reflection is the key focus of this letter. While it might not resonate with every reader, I want to share why position sizing and focus remain two areas where I likely have a lot to gain - and the steps I will take trying to improve this. Maybe you have some experiences here worth sharing as well?

Position Sizing

When it comes to the topic of Position Sizing, this piece from The Intellectual Edge covers it better than I could. It’s definitely worth a read (includes video lessions from the likes of Howard Marks etc.)

The Intellectual Edge
The Most Underrated Skill in Investing
“Position sizing and portfolio construction still do not get the attention they warrant…
Read more
10 months ago · 83 likes · 14 comments · The Intellectual Edge

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