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
08:54 Burning the first batch
09:21 Kervin's strong will
11:18 The steak-choking story
13:06 Adrenaline and instinct
14:06 Growing up with a high-bar dad
16:21 Living up to his father
17:02 Parenting patterns we repeat
19:51 Deciding to have a third
20:35 Fear of the unknown gender
21:15 What changed with a daughter
22:24 Raising Josie differently
23:08 Daddy-daughter dates
27:37 Building a community, not just friends
30:07 Teenage independence and curfews
32:20 Parenting never really stops
33:49 Teaching kids the hard way
36:41 Setting red lines, not rules
37:24 Teaching responsibility with alcohol
40:05 Advice for hesitant dads
41:17 Finding your way without a manual
43:37 Final wisdom for new dads
44:53 A message to Kervin