Podcast Summary

Podcast: Youth Inc. with Greg Olsen
Episode: Jackson, Ethan AND Matt Holliday | How the Holliday Family is Taking Over Baseball
Date: July 11, 2025
Host: Greg Olsen
Guests: Matt Holliday (former MLB All-Star), Jackson Holliday (MLB player), Ethan Holliday (top high school prospect)

Episode Overview

This highly anticipated episode gathers a true powerhouse baseball family—the Hollidays. Host Greg Olsen explores the family’s multi-generational journey through America’s youth sports landscape. The episode delves into youth baseball’s shifting culture, family dynamics, coaching philosophies, the realities of travel sports, and the values guiding one of baseball’s most successful modern families. Through stories and candid advice, the Hollidays share what has shaped their remarkable path.

Key Discussion Points & Insights

1. The Holliday Family "Barn": The Origin Story

[01:29]

• Recording takes place in the Holliday family’s multi-use barn—a former basketball space, now outfitted as a batting cage and pickleball court.
• Matt Holliday: "We spent a lot of time here... this is our best bet at quiet... here we are in our batting cage, pickleball arena."
• Sets the scene for discussing origins, practice environments, and the family’s commitment to building a space for development and togetherness.

2. Father vs. Sons: Baseball Bragging Rights & Family Records

[03:14]

• Greg asks Jackson and Ethan which one is going to surpass their father’s records.
• Jackson/Ethan:
  • "Hopefully both of us... We kind of have a loose goal of, like, having the most home runs in a family..." [03:17]
  • They joke about family bets on performance.
• Memorable moment: Banter about fantasy bets and keeping score within the family.
• Matt Holliday: Open to a “batting cage bill” or repayment if his records hold: "I'll start keeping tabs. I'm gonna write them a bill at the end of their career..." [05:56]

3. The Pressure & Joy of the High School Baseball Experience

[06:56]

• Greg: Asks Jackson what advice he gives to his brother Ethan (and listeners) about handling fame, expectations, and enjoying senior year and high school baseball.
• Jackson Holliday:
  • Emphasizes enjoying high school and playing for the love of the game:

    "High school baseball is really the last time that you get to just go out and play and you’re not playing to earn someone’s approval... it’s really fun." [07:35]

  • Stresses value of good coaches who teach more than just baseball—highlighting character, effort, and fundamentals.

4. Parental Guidance: Knowing When to Push and When to Support

[10:34]

• Greg: Asks Matt about finding the balance between challenging kids to achieve and protecting them from burnout.
• Matt Holliday:
  • Focuses on letting passion lead:

    "If this is what you like to practice, then I’m all in... it’s got to be your idea." [10:38]

  • Advocates that intrinsic motivation and joy sustain success—not parental pressure.
• Greg: Shares struggles as a parent-coach, highlighting difficulty finding coaches who mirror family values.

5. Choosing Coaches & Building the Right Team Culture

[12:43]

• Matt Holliday:
  • Recommends seeking out coaches who care about players’ growth as people, not just statistics or highlight reels:

    "Teaching them how to play the game and teaching them the right way... That’s the sign of where we are... everything is the best on social media." [14:08]

  • Warns against coaches obsessed with individual stats or wins over development.
• Relates to the increasing tension in youth sports between personal branding and team values.

6. Travel Ball vs. Community Teams: What Really Matters

[18:35]

• Jackson Holliday:
  • Remembers most the camaraderie and shared experiences—road trips, hotels, "ding dong ditch," and off-field memories over trophies:

    "Honestly, when I was 10 through 12, most of my memories are like going on different trips with our team... that's what I remember the most." [18:35]

  • Believes strong local/traditional teams taught him the most, not just elite showcases.
• Greg: Echoes importance of team continuity, development, and local community over simply chasing rankings or exposure.

7. The “Recruiting Myth:” The Role of Showcases, High School, and Summer Baseball

[23:01]

• Greg: Challenges the idea that only summer circuits or big showcases matter for recruiting.
• Matt Holliday: Clearly states the importance of high school baseball and relationships:

  "The idea that you only get recruited if you play in every single Perfect Game or PBR tournament is not true. It’s actually quite the opposite." [24:49]

  • Emphasizes contacting college programs, building rapport, and shining in diverse settings—especially high school games, where character is visible to coaches.

8. High School Baseball as a Crucible for Character

[27:47]

• Greg:
  • Shares that scouts and recruiters look for leadership, behavior, and relationships—traits exposed during high school games:

    "I could learn more about him in two innings watching him play high school baseball... than if he flew in to play on the best team in the country..." [28:09]

• Matt & Jackson: Agree. High school baseball is a better barometer of who a player is as a teammate and person.

9. Behind the Scenes: A Day in the Life of a Top Baseball Prospect

[30:15]

• Ethan Holliday: Describes his current routine:
  • Does online schooling (a legacy of Covid), common for several teammates.
  • Spends much of the day on baseball-specific training—speed, agility, hitting, lifting—plus family/faith, and healthy living.

  "We get after it... I love getting better every day... I like to think, like, earning my shower at the end of the day." [33:13]

  • Highlights family discipline, nutrition, and love of competition as distinguishing factors.

Notable Quotes & Memorable Moments

• Greg (to Ethan):
  "So, Dad's going to be in third?" [03:17]
• Jackson Holliday:
  "That's probably the latest. I didn't end up playing really travel baseball until I was about 15, 16... I was on the later side..." [20:53]
• Matt Holliday:
  "If your kid has a passion to practice... then you have a chance to do this at a high level." [10:34]
• Jackson on coaching:
  "Outside of him, obviously. He was fine. Yeah, he was all right." (playful jab at his dad) [08:58]
• Greg on recruiting:
  "I couldn't agree with you more, man. High school sports is where you learn who you are, what you're about." [29:24]
• Ethan on hard work:
  "I like to think, like, earning my shower at the end of the day." [33:13]

Timestamps for Important Segments

• [01:29] Introduction & setting the scene in the family “barn”
• [03:14] Family banter on surpassing dad’s records & bets
• [06:56] Advice from Jackson to Ethan & others on handling pressure
• [10:34] Matt discusses balancing encouragement and restraint as a parent
• [12:43] How to choose coaches and building healthy team environments
• [18:35] Jackson recalls youth travel ball memories
• [23:01] The myth of recruiting: high school vs showcases
• [27:47] Why high school baseball matters to scouts and families
• [30:15] Ethan breaks down a day in his life and training regimen

Episode Tone & Takeaways

The Hollidays’ conversation is warm, insightful, and playful, combining deep family loyalty with a grounded, real-world perspective on youth sports. They stress intrinsic motivation, community, and character over hype. The hosts and guests challenge common myths about recruiting and overspecialization, offering a vision of youth sports that’s both ambitious and fundamentally healthy. From practical routines to motivational advice, the episode is a must-listen for parents, coaches, and aspiring athletes.