Parenting like a Superdad

Episode 26: How High School Sports Really Work (Inside CCS with Commissioner David Grissom)

In this episode, I sit down with CCS Commissioner David Grissom to break down how high school sports actually work behind the scenes.
We talk about how decisions are made, the challenges schools face, and what parents and athletes need to understand as they move from youth sports into high school.
If you have a child in sports—or plan to—this conversation will give you a clearer picture of what to expect.

Episode 25: Inside MLB Without Playing: Alex Slater on Careers in Sports & Youth Development

Right in time for Opening Day, this episode takes a different look at youth sports.
Most kids who play sports dream of going pro—but very few actually do. So what should parents and kids really be focused on?
In this episode, I sit down with a high school classmate of mine, Alex Slater, who built a career inside Major League Baseball, working his way from an intern to Vice President and Assistant General Manager of the Los Angeles Dodgers.
We talk about the reality of careers in sports beyond playing, what it actually takes to work in professional sports, and how youth sports should be developing more than just athletes.
If you have a child in sports—or you’re thinking about their long-term future—this conversation will give you a different perspective on what success can look like.

Episode 24: Pat Hankin — Rethinking Single Parenting

Summary:Pat Hankin, author of The Field Guide for Single Parents, joins Derrick to discuss the realities and misconceptions surrounding single-parent households. Pat shares practical strategies for managing time, money, and stress while raising resilient kids—along with why traditional advice often fails single parents.
From the “15-Minute Parent” concept to building support systems in unexpected places, this conversation offers clear, practical guidance for parents trying to balance family, work, and life.

Episode 23: How Parents Build Confidence (Even When They Feel Uncertain) with DJ Stutz

In this episode of Parenting Like a SuperDad, Derrick sits down with DJ Stutz — a lifelong caretaker, foster and adoptive parent, and mom of five — to talk about the imperfect, meaningful journey of parenting.
They explore what it means to build confidence as a parent, improve communication with children, navigate discipline and emotions, and support healthy sibling relationships. DJ shares insights from her personal experience and her work with families, reminding us that parents don’t need to be perfect to make a powerful impact.
This conversation is for any parent who has ever wondered if they’re doing enough — and wants encouragement to keep showing up and growing.

Episode 22: There Is No Perfect Path — Just Better Questions (with Randall Tom)

This episode of Parenting Like a Superdad is a reflective conversation in which Randall Tom asks Derrick thoughtful questions about parenting, values, and decision-making when certainty fades.
Randel, a Bay Area native, aspiring broadcaster and journalist, and a sophomore at Syracuse University, brings a curious, generational perspective that helps surface deeper reflection around listening to the child, choosing values over nostalgia, and how confidence is built through trial, discomfort, and ownership.
The conversation explores the tradeoffs parents face when circumstances change and the importance of staying aligned while remaining open to adjustment.

Episode 21: Raising Boys in a World That Keeps Changing

Many parents today aren’t worried about raising perfect kids — they’re worried about raising kids with character.
But when it comes to raising boys, the guidance can feel conflicting, outdated, or incomplete. Strength versus sensitivity. Discipline versus understanding. Independence versus connection.
In this episode, Derrick sits down with Shaun Dawson, host of Raising Men, to talk honestly about why raising boys today feels harder than it used to — and what parents can focus on when there isn’t a clear playbook.
They discuss emotional resilience, healthy masculinity, the role of modeling over messaging, and how parents can guide boys through pressure, screens, and modern expectations without losing the values that matter most.

Episode 20: Sports, Screen Time, and Raising Resilient Kids

Sports, Screen Time, and Raising Resilient Kids
In Part Two of this conversation, Derrick continues his discussion with family therapist Angela Caldwell by shifting the focus to sports, competition, and the digital world kids are growing up in today.
Drawing from Angela’s background as a competitive athlete, they talk about how sports can teach resilience, accountability, and optimism — and where families sometimes struggle to find balance. The conversation also explores how parents can think more intentionally about screen time and social media without fear, overreaction, or avoidance.
This episode closes out 2025 with a reflection on growth, boundaries, and raising kids who are prepared to navigate both challenge and change.

Episode 19: It Takes a Village — Why Parents Feel Alone

It Takes a Village — Why Parents Feel Alone
Parenting was never meant to be a solo effort — yet so many parents today feel like they’re doing it alone.
In Part One of this conversation, Derrick sits down with family therapist Angela Caldwell to unpack what people really mean when they say “it takes a village.” They explore why modern families often struggle to find support, how misalignment (not failure) creates isolation, and what shared values have to do with feeling truly supported.
This episode is a thoughtful reflection on connection, communication, and why building a village is less about having more people around — and more about clarity, trust, and intention.
In Part Two, the conversation continues with a focus on sports, screen time, and social media.

Episode 18: Building Happier Families With Anil Gupta

In this episode, world-renowned relationship expert Anil Gupta — The Love Doctor — joins us for a parent Q&A. Anil has coached families in 18 countries, spoken on TEDx and major media outlets, and created tools like The Happiness Formula and The Relationship Score. Together, we talk about practical ways parents can build stronger connections, support their kids, and bring more love and intention into family life.

Episode 17:Coach Joey Curtin | Building Champions at Riordan and Beyond

Coach Joey Curtin has helped bring new life to one of San Francisco’s most storied basketball programs at Riordan High School. In this conversation we talk about his path from player to head coach, what it means to build athletes with both skill and character, and how he sees middle school sports shaping kids today. From the energy of the Crusader Forum to lessons that last beyond the court, this episode is about tradition, growth, and raising young people to compete with purpose.
Music in this episode provided by our friends in the Riordan community.