A podcast for people who want to win with money without losing themselves in the process.
Before you press play
Why you shouldn't listen to me
- Brought over $60,000 of debt into my marriage
- Lived in a basement suite with $5 left in the budget each month
- Ate chickpeas five nights a week
- Took a warehouse job right after our honeymoon
- Pretended to be someone I wasn't, until Emily stopped talking to me for a week
- Wore $5 thrift-store boots a size too small
- Had six months of numb toes
Why you should
- Paid off that $60,000 in seven months
- Retired Emily before either of us turned 30
- Top 1% banker, with 8+ years in banking
- Top 40 Under 40 (2025) and Business Leader of the Year finalist (2026)
- Bought two properties in one day
- Two-time #1 Amazon bestselling author
- Now owns boots that fit
Recent episodes
See every episode →-
EP39
She Spent 16 Years Climbing the Ladder. Then She Pivoted. Dr. Tristin Brisbois
What does it actually cost to walk away from something you spent eighteen years building? Dr. Tristin Brisbois has spent her whole career, in wildly different settings,…
60 minSeptember 21 -
EP38
You're Running Two Races Every Day (And You Only Trained for One)
Are you actually done when you walk through your front door, or does it just feel that way because you're exhausted? Justin Whitmel Earley finished a 10K Tough Mudder…
8 minSeptember 14 -
EP37
Our Filmmaker Breaks Down Every Step of Making Currency of Happiness
Behind the Scenes Dion WiebeEver wonder what actually happens before and after we hit record on this show? For this episode, I sat down with Dion Wiebe, the filmmaker behind The Currency of…
25 minSeptember 7 -
EP36
Why Successful People Are Secretly Unhappy (3 Questions That Explain It)
Are you happier now than you were ten years ago? Not richer. Not further along. Happier. Harvard professor Dr. Arthur Brooks has spent years studying that question, and…
19 minAugust 31 -
EP35
Addiction Recovery in Canada: What Actually Happens Inside a Treatment Centre
Darryl Wilkie CEOWhat do you do the night you've decided this is either going to be the night you get help, or the night you don't wake up? Darryl Wilkie is the executive director of the…
56 minAugust 24
Turn Your Dreams Into Reality
The free goal-setting framework Emily and I actually use. Look at your whole life first, then pick a few goals worth chasing.
- The Six Fs: finances, family, friends, faith, fitness and freedom (the one most people forget)
- SMARTER goals, which add Exciting and Risky to the usual SMART
- Worksheets that turn the big picture into no more than three goals at a time
- Why your goals don't have to match your spouse's, and other things we learned the hard way
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From the blog
All posts →Why Hitting Your Money Goal Feels Like Nothing (and How to Define Enough)
Ever hit a financial milestone and felt almost nothing? A Wall Street cautionary tale, the research on moving goalposts, and how to define enough…
From the show · March 31, 2026The Guy Under the Orange Tent Had No Idea He Was Building Something
Reading didn't change my life in one dramatic moment. It worked slowly, the way your eyes adjust in a dark room. What it's done for me, and how to…
From the show · March 2, 2026Can Money Buy Happiness? Only If You Use It This Way
How much money you have matters less than what you use it for. The five places every dollar goes, and which ones actually make people happier.
Hi, I'm Andrew.
Emily and I paid off $60,000 of debt in seven months. I've now spent eight years in banking, and I keep watching people hit the number they've been chasing and sit down across from me more anxious than before they got it.
So I stopped asking how to make more money and started asking what it was for. Now I get to ask it every week, sitting across from people who've built something or been through something hard. And every conversation ends with the same question: what does happiness look like to you?