Annika Hedstrom's medical finance crisis and insurance importance

Here's what nobody tells you about building wealth: it's not about finding the perfect investment or timing the market. It's about doing boring things consistently until they're not boring anymore—they're just your life.

In this Greatest Hits episode, Joe Saul-Sehy and OG revisit a 2023 conversation with Jonathan Clements, the beloved former Wall Street Journal personal finance columnist and founder of Humble Dollar who passed away recently. We're resharing this episode to honor Jonathan's legacy, his gift for making complex ideas simple, and the joy he brought to every conversation about money.

Jonathan's book, My Money Journey, features 30 real stories from real people who built financial freedom—and the lessons are surprisingly simple (which doesn't mean easy). In this conversation, Jonathan breaks down what separated the people who made it from the people who kept spinning their wheels: steady habits, ruthless simplicity, and the kind of resilience that lets you keep going when life throws curveballs.

From emergency funds that actually saved people to the rent vs. buy debate that reveals more about your priorities than your budget, this conversation cuts through the complexity to show you what actually matters. Jonathan's wisdom feels even more valuable now—a reminder that the best financial advice isn't about chasing trends, it's about building a life that works for you.

Joe and OG also tackle listener questions, including whether to relocate for a better job and how to balance saving for tomorrow without sacrificing today. Plus: Doug's trivia, a Key & Peele-inspired TikTok minute, and proof that the best financial teachers leave lessons that last long after they're gone.

What You'll Walk Away With:

• The money habits that showed up in almost every success story from Jonathan's book (spoiler: none of them are sexy)

• Why simplicity beats complexity in investing—and how to stop overcomplicating your portfolio

• The rent vs. buy question reframed: it's not just about math, it's about what kind of life you want

• How to balance aggressive investing with the safety net you actually need (not the one Instagram tells you to have)

• Why emergency funds and health insurance are the unsexy heroes of every financial success story

• What "margin for error" really means—and why it's the difference between surviving setbacks and being destroyed by them

This Episode Is For You If:

• You're tired of chasing the next "hot" investment strategy and want to know what actually works

• You feel like everyone else has figured out money except you (spoiler: they haven't)

• You want to hear real stories from real people, not just theory from talking heads

• You're trying to balance living well now with saving for later—and feeling stuck in the middle

• You believe the best teachers are the ones whose lessons outlive them

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

Learn more about your ad choices. Visit podcastchoices.com/adchoices