Courage and Vulnerability in Listening

Be honest: When someone's talking to you, are you actually listening—or just waiting for your turn to speak? Joe Saul-Sehy and OG welcome executive coach Katie O'Malley, who's here to expose how terrible most of us are at paying attention—and more importantly, how to fix it. Whether you're trying to connect with your spouse, navigate a tough conversation with your kid, or just survive Thanksgiving dinner without the crypto uncle derailing everything, Katie's got the framework that makes you a better listener (and weirdly, a better decision-maker too).

Here's the thing: better listening doesn't just improve your relationships. It improves your money decisions. When you're actually present instead of distracted, you catch the details that matter. You ask better questions. You make choices that align with your values instead of reacting on autopilot. Katie breaks down the reflective listening technique that changes every conversation—at work, at home, and yes, even about money.

Joe and OG also dig into financial literacy for younger Stackers (because the skills you wish you'd learned earlier are the ones you should be teaching now), plus new research on all-stock portfolios and whether they're brilliant or just reckless depending on your risk tolerance.

And Doug? Doug's got Halloween-adjacent music trivia and commentary that reminds you not everything needs to be taken seriously.

What You'll Walk Away With:

• The reflective listening framework that immediately improves how you communicate (with everyone)

• Why "listening to respond" instead of "listening to understand" sabotages your conversations

• Simple techniques to break free from distraction loops—especially the ones involving your phone

• How better communication leads to better financial decisions (they're more connected than you think)

• What the research actually says about all-stock portfolios and whether they fit your risk tolerance

• Ways to teach young people the financial skills they need—even if nobody taught you

• Strategies for staying present during stressful family moments (holiday season, we see you)

Before You Hit Play, Ask Yourself:

• When was the last time you listened to understand instead of just waiting for your turn to talk?

• What relationships in your life would improve if you were actually present instead of mentally writing your grocery list?

• Are you teaching the young people in your life the money skills you wish someone had taught you?

• Does your investment strategy match your actual risk tolerance—or just what sounded good on TikTok?

• What uncomfortable conversations are you avoiding because you don't know how to navigate them?

Got a communication breakdown you're trying to fix—financial or otherwise? Drop it in the comments. The basement's got your back.

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

Enjoy!

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