Ep 30: Michael Prince On Community, Chaos, And Raising Three Kids

A chance seat on a flight from Denver turned into a decades-long friendship, and a crash course in fatherhood. This week I sit down with my longtime friend Michael Prince to talk about the early terror of parenting a firstborn, the night his son started choking on steak at the dinner table, and why staying calm matters more than having the right answer. We get into raising a daughter after two sons, building a family culture around community and hospitality, teaching teenagers responsibility instead of just rules, and the regrets that come with parenting on the job. Michael's honesty about what he'd do differently makes this one worth sharing with any dad figuring it out as he goes.

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Key Takeaways:

Staying calm in a crisis matters more than having the perfect response; overreacting fuels the fire.Parenting a firstborn often means learning through trial and error with no real playbook.Building community with other parents can be one of the most valuable supports of early fatherhood.Raising a daughter after sons requires learning new sensitivity and intentional one-on-one time.Teaching kids the "why" behind a task matters as much as giving them the easy solution.Discipline works best with clear boundaries paired with real communication, not control.Parenting doesn't end when kids move out; it just changes shape.Growing up with a highly accomplished parent can create a bar that's hard to know you've cleared.Family culture, whether it's music, hospitality, or hosting, gets passed down whether you plan it or not.Every parent carries regrets; what matters is staying self-aware enough to adjust.00:00 Cold open

00:42 Meet Michael Prince

01:18 How Tony and Michael met

02:05 The flight that changed everything

03:10 Becoming each other's sanity

04:13 Babymoon gone sideways

04:52 The terror of a firstborn

06:02 Self-conscious in public with kids

07:16 Learning to stay calm