In this episode of The Free Lunch Podcast, Greg and Jacob reflect on how the reality of wealth advising differs from what’s taught early on.

Technical knowledge matters, but it isn’t what ultimately sets wealth advisors apart. Listening, understanding, and guiding people through uncertainty are what define the work.

Throughout the episode, they explore the lessons that only experience teaches, and what it really takes to build a career that lasts.

If there’s one lesson that kept showing up over nearly 300 episodes, it’s this:

being reasonable beats being brilliant.

In this episode of The Free Lunch Podcast, Colin reflects on five themes that have shaped the show over the years, starting with why behaviour matters more than intelligence, forecasts, or clever strategies.

It’s a reminder that long-term success rarely comes from bold moves. It comes from consistent, disciplined decisions made over time.

When markets move, our instincts kick in fast. ⏱️

In this episode, Colin and Greg share a real example of a new investor reacting to a small short-term loss, and use it to explain why checking your portfolio too often can do more harm than good.

They break down volatility, time horizons, and why investing isn’t meant to feel like watching a savings account.

We’ve become far more comfortable with debt than we used to be.

In this episode of The Free Lunch Podcast, Rob Carrick, one of Canada’s most trusted personal finance journalists and longtime columnist at The Globe and Mail joins Greg and Colin to talk about how consumer culture has reshaped our relationship with money.

They discuss frictionless spending, social media pressure, and why debt often builds quietly, without a clear moment where things go wrong.

We procrastinate on taxes for the same reason we avoid the dentist. We know it’s important, it just feels uncomfortable.

In this episode of The Free Lunch Podcast, Colin and Blair talk about tax optimization, early planning, and why contributing sooner to your TFSA or RRSP can be one of the most underrated financial habits.

It’s step four in their “12 Steps to Greatness in 2026” list, and they cover all 12 to help you start the year with clarity.

Is there really a free lunch when it comes to investing?

According to Greg and Colin, there is one: diversification.

It’s not exciting. It doesn’t make headlines. But it’s one of the few strategies that has improved outcomes while helping reduce risk over time.

In this episode, they explain why diversification works, why investors resist it, and why it matters right now.

Where would modern thinking about markets be without the people who pushed it forward?

This week on the Free Lunch Podcast, Colin and Greg reflect on the thinkers and researchers who reshaped the way we understand economic behaviour. From evidence-based approaches to frameworks that bring discipline and clarity to decision-making, the way we view the world today exists because a few pioneers were willing to challenge old assumptions.

We buy everything else on sale, but with stocks we do the opposite?

In this episode, Colin and Greg talk with Mark Eibel about the strange way human behaviour shows up around money. The market rises more than 70% of the time, yet fear in the 30% often pushes people out at exactly the wrong moment.

It is one of the few areas of life where people get more interested as prices rise and more nervous as prices fall, even though history shows that downturns are usually shorter than they feel.