Episode Guest: Brendan Sullivan, Founder & CEO of Head First

In this episode, host Rob Carmichael is joined by CBT therapist Betsy Carmichael (Alvord Baker & Associates) and Flagstar founder Carl Ehrlich ("the commish") for their first-ever guest interview: Brendan Sullivan, a DC native, former Stanford baseball standout, and pro pitcher who built Head First from one-on-one pitching lessons into a multi-division youth sports, camps, and college-recruiting organization — plus an unexpected music-touring business, KI Concerts.

The conversation moves from Brendan's origin story (getting paid $850/month in the minor leagues, writing a painfully honest column for The Washington Post about his own struggles) into the heart of the show's mission: how youth sports can build — or erode — resilience.

What we cover:

• Brendan's path from Stanford and the minor leagues to founding Head First, and how the youth sports landscape has transformed since 1996
• The "arms race" dynamic in youth sports: how well-meaning, rational parents get pulled into over-scheduling out of fear of falling behind
• How to actually talk to your kid about doing too much — reading behavior (not just enthusiasm), protecting unstructured "boredom" time, and being honest about trade-offs
• Whose decision is it, anyway? Reinforcing that parents "drive the bus," even when it feels like the system is driving them
• The genetics-versus-grind debate: Carl's take on why hard work matters but isn't the whole story
• Coaching your own kid: Brendan on parenting through effort lapses, benching his son, and resisting the instinct to shield kids from disappointment
• Clear lines for coach-parent conversations — what's in bounds (behavior, effort, life stuff) and what's not (playing time, lineup decisions)
• Teaching self-advocacy: how to help a kid have the hardest conversation of their year — asking a coach directly what they need to improve
• The "Super Six" resilience skills Head First builds its curriculum around: hope and goal-setting, optimism, emotional mastery, grit and determination, self-efficacy, and resilience itself
• The difference between a "professionalized experience" and a "professionalized childhood" — and why healthy competition (including keeping score) still matters for development
• Why parent-sideline behavior has changed since COVID, and Brendan's (only half-joking) dugout cone barrier