Weekly Round-Up -- May 21, 2026

Good morning! We hope everyone had a wonderful long weekend and enjoyed the beautiful spring weather (finally!).

This week Dave sits down with Dr. Daniel Crosby — psychologist, behavioural finance expert and bestselling author — for a fascinating conversation on the psychology behind investing and why emotions so often drive financial decisions. From investor overconfidence and social-media fuelled speculation to the “gamblification” of investing and Daniel’s “three E’s” framework for better decision-making, this episode is packed with insights on how people can make smarter long-term financial choices.

PODCAST
Daniel Crosby: How to Overcome Your Financial Biases

Our guest this episode is Dr. Daniel Crosby — psychologist, behavioural finance expert and Chief Behavioural Officer at Orion Advisor Solutions. Daniel is the bestselling author of several books on the psychology of money, including "The Behavioral Investor" and "The Soul of Wealth," and is the host of the popular podcast "Standard Deviations." His mission is to help investors and advisors understand how psychology shapes financial decisions and what true wealth really means.

In this episode, Dave and Daniel dive into the psychology behind investing and the behavioural biases that quietly sabotage even the smartest investors. They break down the four major investor biases, why overconfidence is the most damaging of the bunch and Daniel's "Three E's" framework for overcoming them. They also explore why money is emotional rather than purely mathematical and the role behavioural fintech design can play in helping people make better long-term decisions.

The conversation also explores the rise of the "gamblification" of investing, the impact of social media on young investors and why personal benchmarking tends to serve people far better than chasing the S&P 500. Along the way, Daniel shares his framework of believing, belonging and becoming as the keys to a good life, his perspective on managing anxiety in uncertain times and why so many investors still fall into the trap of buying high and selling low.

Whether you're a seasoned investor or just starting to think about your relationship with money, this episode is packed with insights that will help you understand yourself as much as the markets. Tune in now on our website, YouTube, Apple Podcasts, Spotify and all other podcasting platforms!

THROWBACK THURSDAY
Employees: Stop Leaving Benefits on the Table

⏪Throwback Thursday: One of Dave’s biggest teachings over the years: take advantage of the benefits your employer already offers. A lot of Canadians still aren’t doing this!

“Many Canadians are leaving a lot of free money on the table. C’mon!!”

ESTATE PLANNING
A Creative Idea for How to Fairly Share a Family Wedding Ring

Daniel Glazier shares a creative solution for families struggling over who should inherit a wedding ring.

INVESTING
How to Invest Better with the “Three E’s”

Daniel Crosby breaks down the “Three E’s” of better investing: education, environment and encouragement.

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