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Investing & Retirement

Should you be hand-picking stocks? Timing the market? Or taking the “lazy portfolio” way out?

Investing and Retirement are complicated and consequential topics. The articles below address these complex ideas.

I hope you enjoy them! And let me know what other questions you’d like me to dig into.

person riding on red parachute

Room For Error

What one famous writer, two famous investors, and a pack of famous dogs can teach us about avoiding big mistakes.

baked orange pie

Is Investing a Zero-Sum Game?

“Jesse – when you zoom out on investing as a whole, isn’t it all zero-sum game? Can’t we only have winners when other people are losers?” Let’s dive in!

ocean wave at blue hour

Rogue Waves, Rogue Markets

Until 1984, the sailing world dismissed the existence of “rogue waves.” Oops. It’s an interesting story, and relates to an important lesson about today’s stock market.

cute siblings resting in green garden

Gardeners and Diners

This will piss off some advisors, but not everyone needs professional financial help. Here’s the analogy I use to explain it.