I love a good quote. Here's one I came across recently that I had never heard before: "People can only understand us at the depths in which they have met themselves." What's a great undiscovered quote you've come across?

Pro Tip: When you're looking for a financial advisor, one of the best questions you can ask is how many clients they work with. Here's why ...

Spoiler alert: Trading in the markets is the most competitive game there is. Most institutional money managers (with the smartest minds working on it full-time) can’t beat the markets. So no, your financial advisor John from Burlington won’t beat the markets either.

Creativity isn’t bestowed, it is unlocked. And notice, I didn’t put quotes around that sentence? That’s because I made it up tonight. Go ahead, google it. I’ll wait … And ya, I’m pretty proud.

Many people, even professionals like accountants, lawyers, and investment managers, don’t know what a financial planner does. For a long time, I didn't either. How can that be? It has to do with the history (or lack thereof) of the profession. 🧵Here's the story ...

Impact investing isn't just investing in companies that make you feel good. It requires you to fundamentally rethink the why, what, where, when, who and how of investing.

If active investing is a bad bet, what’s a good one? Financial planning. Most people radically underestimate how much value a great financial plan can add. Let’s break it down. 👇 1️⃣ Active investing is a zero-sum game. For one investor to win, another has to lose. And after fees? The average investor loses. But financial planning isn’t about beating anyone. It’s about optimizing your wealth using tax rules, legal structures, and smart money strategies. The upside isn’t just possible—it’s predictable. 2️⃣ There’s more room to add value. Everyone’s financial situation is unique. And almost everyone has inefficiencies—decisions that are costing them money without them realizing it. But most people have no idea where these inefficiencies are hiding. Why? 👇 3️⃣ Wealth optimization is more complex than it looks. Some decisions seem simple—until you dig deeper: - Who should be the beneficiary of your RRSP, LIRA, TFSA? - How should you fund (and withdraw from) your RESP? - RRSP vs. TFSA vs. FHSA vs. RESP—where should your next dollar go? - How and when should you take income from your business? - When (and how) should you use life insurance? Each question has hidden complexity that can cost you thousands if you get it wrong. 4️⃣ Financial planning isn’t just “budgeting” or “retirement planning.” A great planner can help with things most people don’t even realize matter: ✅ Tax & estate planning ✅ Investment structure optimization ✅ Risk management & insurance ✅ Retirement withdrawal strategies ✅ Complex financial decisions 5️⃣ The best part? Unlike active investing, financial planning isn’t a gamble. It’s not about beating anyone. It’s about understanding the system and making better choices within it. Smart money moves aren’t about luck—they’re about strategy. 🔜 Next, I’ll share some real life examples of the ways we've surprised our clients by finding money they didn't realize they were leaving on the table, like: 💰 Using a currency broker to save $6k on a large USD/CAD exchange. 💵 Securing $1,200/month in GIS payments to help ease the financial burden of caring for an elderly parent. 🏦 Taking advantage of promotional offers to earn $15K+ in cash rewards and $5k/yr and $5k/year in additional credit card rewards points for moving to a new trading platform and credit card rewards card. 💳 Finding $500/month in subscriptions clients didn't realize they were still paying for. These aren’t maybes. These are real, measurable results.

Our drug laws are precisely backwards. Any impartial, evidence-led observer would have to admit that we'd be far better off banning alcohol and tobacco (cigarettes) over psychedelics or cannabis. Consider the data 📊 ...

Late capitalism, in a nutshell.

Here's a shocking confession from a CFA charter holder who has worked in financial services for over 25 yrs: I didn't know what a financial plan was for the first 15 yrs of my career. The reason I'm not embarrassed to admit that now ...

Let's all normalize talking about mental health. I struggle with it like everyone else. I'd love to see a world where we normalize regular mental health checkups like annual physicals are normalized.

I often talk about the distinction between investment management and financial planning and how financial planning is more valuable than investment management (which is increasingly becoming a commodity). If you're shopping around for financial advice, be careful ...

Herein @Frankcaprio_ proves that any job, even administering justice can be done with kindness.

I love visualizations like this that help us comprehend incomprehensibly large figures. Here's my own spin on Regan's great framing: If you had a stack of thousand-dollar bills in your hand only four inches high, you’d be a millionaire. A billion dollars would ...

I read a quote recently that floored me: “People can only understand you at the depth they’ve met themselves.” It’s been living in my head ever since. Here's why 👇

How ESG challenges our understanding of Modern Portfolio Theory In Ep 33, I sit down with Jon Lukomnik to discuss his book: Moving Beyond Modern Portfolio Theory (co-authored by James Hawley). 🧵1/ Here's the crux of what we discussed: davidoleary.ca/the-impact-in…

Sports boils down to one kid looking over at another kid, saying, "I bet I can do that better than you."

When it comes to investing investing, the difference between professionals and amateurs essentially boils down to risk management.