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In this episode of The Threshold, Matt, Brent, and Rich reunite after more than a year apart to talk about how much life can change, and how the things designed to make life easier don’t always make it better.
Matt opens up about divorce, grief, losing his father, and navigating dating again in a world of apps, endless choice, and what he calls the “convenience trap.” Brent reflects on balancing a thriving business and family life with health, a move toward farm living, and the feeling that midlife may offer a rare combination of experience, freedom, and clarity. Rich shares his return to jiu-jitsu, the pressure of adapting a business in an AI-driven world, and why genuine human connection may become even more valuable as technology gets better at imitating it.
The conversation moves through dating, masculinity, marriage, parenting, co-parenting, changing expectations between men and women, and what happens when you reach a stage of life where you know yourself better and become more deliberate about where you spend your time.
Along the way, they explore why convenience can sometimes work against us, whether it’s swiping instead of meeting people in the real world, relying on technology instead of conversation, or choosing the easy option over the experiences that actually create meaning.
It’s part reunion, part therapy session, and part midlife reality check. A conversation about relationships, resilience, real human connection, and why the harder path can sometimes be the one worth taking.
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