Podcast Summary – The Dan Le Batard Show with Stugotz

South Beach Sessions - Max Greenfield
Released: November 20, 2025
Host: David Jacoby (for this session)
Guest: Max Greenfield

Episode Overview

Recorded at the Elser Hotel in Downtown Miami, this episode features a candid, in-depth conversation between David Jacoby and actor/writer Max Greenfield. The discussion explores Greenfield’s unconventional path to success, his struggles with traditional education, the roots of his children’s book series, forging a creative life, the joys and anxieties of balancing family and career, and his experiences working on the Netflix show "Man on the Inside" with Mike Schur and Ted Danson. The conversation is warm, humorous, vulnerable, and deeply reflective, offering listeners meaningful insight into Greenfield’s journey and the broader challenges of choosing an artistic life.

Key Discussion Points & Insights

1. Setting the Tone for an Intimate Conversation

• Greenfield requests a more intimate discussion, wishing the audience could've heard their off-camera chat (01:58).
• Jacoby introduces Greenfield and the Netflix project "Man on the Inside," created by Mike Schur (02:25).

Greenfield: “Mike Schur’s the greatest. I’ve known him for a very long time… it was spectacular, as you would imagine.” (02:57)

2. The Genesis of Writing Children's Books

• Greenfield explains how the COVID-19 pandemic prompted him to be more involved in his daughter’s education due to school closures. He admits schooling was always challenging for him, both as a student and parent (03:33).
• This struggle and public vulnerability led to him documenting the experience via Instagram, which unexpectedly created a supportive online community—especially among frontline workers (05:20).

Greenfield: “Using social media in the way that I think it should be used, which is we’re scared, we’re overwhelmed, we feel very alone. We want to connect with other people and see hopefully, that other people are feeling the same way as we are. And we got this tremendous response…” (05:20)

• A literary agent noticed the Instagram posts and pitched Greenfield on creating a children’s book. The concept, "I Don’t Want to Read This Book," humorously tackles kids' reluctance to read and is reflective of Greenfield's own struggles with learning (08:33).

3. Struggles with Education and Finding Support

• Greenfield shares openly about his academic challenges, eventual decision to drop out, and the supportive but concerned response from his family (12:56).
• The experience inspired his approach to children's books—being honest about struggles and opening conversations between kids, parents, and educators about learning differences (10:34).

Greenfield: “The books… are not like, solving childhood literacy in our country, but it’s another tool for teachers… trying to get kids to open up and talk about what’s going on with them and what struggles they might be having in a classroom that they’re unable to articulate.” (11:40)

4. Parental Expectations, Taking Alternative Paths

• Both Jacoby and Greenfield discuss the difficulty of departing from their fathers’ expectations—Jacoby’s father wanting him to become an engineer, Greenfield’s father being in finance—and the fears involved in pursuing creative careers (16:12–17:46).
• Greenfield recounts a humorous story of his dad interacting with rapper KRS-One at Warner Brothers, illustrating his parents’ complicated but ultimately supportive view of his artistic pursuits (17:59).

5. Hollywood Hustle: The (Very) Long Road to ‘New Girl’

• Greenfield debunks the myth of "early success," detailing 10-12 years of odd jobs, including delivering pharmaceuticals to retirement homes and various side gigs, while grinding for acting roles (20:00–27:55).
• He describes near-misses and the emotional rollercoaster of being a working actor without big breaks, with bits parts and no lasting roles for more than a decade (22:49).
• The realities of financial and emotional strain hit especially hard with the responsibilities of impending fatherhood, almost leading him to quit acting (31:14).

Greenfield: “I was running around on audition to auditions, and I thought, I don’t want to be the guy who’s like, bringing the car seat into an audition… It just felt like a very selfish choice at that point to put this career ahead of what was so obviously now important.” (31:14)

6. Crossroads: Family versus Artistic Dreams

• Both Max and his wife Tess go through career upheaval as she loses her casting executive job and he considers giving up on acting; both are unemployed while expecting their first child (33:09).
• Max emphasizes the profound effect of becoming a father—it changed his priorities and perspective on what mattered most in life (35:34–36:32).
• Ironically, letting go of his need for a "big break" and embracing his family responsibilities paved the way for him to land his breakout role on "New Girl" (36:32).

Greenfield: “It was probably because of that shift in perspective that I was able to approach what I was doing in a different way. And then was very lucky a New Girl came out.” (36:24)

7. Work, Success, and Sustaining Joy

• Discussion of “enoughness”—how neither host nor guest fully planned their careers, but instead followed what inspired them, pivoting when necessary and embracing unexpected opportunities (40:27–43:52).
• Both stress the importance of community, joy, and gratitude as engines for creativity.

Greenfield: “...the thing that I love the most in life is discovery… moments that feel like discovery to me are the most fulfilling.” (47:44)

8. Therapy, Self-Judgment, and Kindness

• Jacoby and Greenfield candidly discuss therapy and the lifelong challenge of being overly hard on oneself. Jacoby notes his biggest struggle has been learning how to be kinder to himself, especially after loss and hardship (51:50–54:33).
• Greenfield shares how he’s working to reduce self-judgment and find greater self-acceptance.

Greenfield: “It’s like discovering that I have so much power over… I’m giving myself so much power over myself. It’s weird. It’s a weird thing to discover this late in life.” (54:33)

9. On Confidence and Collaboration with Heavyweights

• Greenfield reflects humbly on his career, admitting to entering new projects "terrified" but relishing the opportunity to work with the best (“Man on the Inside” w/ Mike Schur, Ted Danson). He credits his ability to collaborate well, serve the vision, and learn from those around him (55:35–58:53).

Greenfield: “Being with those folks and being able to collaborate with them and not feel…scared enough…that it takes away from what we’re trying to do and have an understanding about what they’re talking about and what they’re asking from you. Being in that situation and feeling like you are adding to what they’re doing, that’s a really good feeling.” (55:35)

• He shares an amusing story about screwing up his one line during a complicated camera shot on his first day, and how welcoming and collaborative the environment ended up being (58:53–61:53).

10. Artistic Process: Playfulness and Growth

• Max and Mike Schur developed a playful working relationship, experimenting with bits and gags—some making the final cut—and deepening both their friendship and the creative quality of the show (63:18–64:56).

Greenfield: “It became a full playground… I may or may not have begged him to let me do [bits], which he then reluctantly allowed me to do. One of the things ended up in the show.” (64:21)

Notable Quotes & Memorable Moments

• "I can't believe I'm here. I was on stage… at this thing. And they were like, well, you know, we had Bill Nye a couple years ago, and Maya Angelou… LeVar Burton… I'm so sorry." — Max Greenfield, on being invited to educator conferences (12:16)

• "Who’s going to pay you to do that?" — David Jacoby quoting his father's reaction to his desire to be a writer (17:11)

• "Most actors get jobs as waiters, but I was too scared to be a waiter because I didn’t think I could remember people’s orders… so I got this job delivering pharmaceuticals to old age homes…" — Max Greenfield (27:11)

• "I don’t know that my dreams were ever gonna fulfill me in the way that this child has. Those all seem futile now." — Max Greenfield on fatherhood changing priorities (35:34)

• "I just took the joy of doing that. And then the next thing you know, they were like, ‘You’re the guy we want to hire.’ And then I thought, well, I’ll never get it. And, you know, the rest sort of…" — Max Greenfield on how he landed "New Girl" (36:32)

• "The thing that I love the most in life is discovery… it can be as simple as walking down the Sunset Strip and discovering that in this moment I feel really grateful…" — Max Greenfield (47:44)

• "Are you hard on yourself?" — Jacoby

• "I’m trying to ease up. I’ve been so much better lately." — Greenfield (51:13)

• "I understand what you’re saying. I get, like, the self-deprecating thing and everything. Maybe, again, maybe it’s the wrong way to articulate it, but it’s the thing that I enjoy most in life and which I try to stay connected to always. I love that we’re having this conversation. It’s really nice. I didn’t think we were going to go down this route, but the thing that I love the most in life is discovery." — Max Greenfield (47:44)

Important Timestamps

• [02:09] – Greenfield's desire for intimacy, his path to working with Mike Schur
• [03:33] – How the pandemic led to creating content with his daughter
• [08:33] – The children's book idea and its origins
• [10:34] – Reflection on learning struggles and access to resources
• [12:56] – Dropping out of school; family reactions; finding acting
• [20:00] – Greenfield’s “10- to 12-year grind” before major career success
• [27:03] – Delivery work in retirement homes; emotional impact
• [31:14] – Fatherhood, career crossroads, almost quitting acting
• [36:32] – Shift in priorities leads to “New Girl” opportunity
• [47:44] – On discovery, gratitude, and maintaining a childlike sense of wonder
• [51:13] – Both reflect on being hard on themselves and the journey toward kindness
• [55:35] – Working with Mike Schur and Ted Danson, creative collaboration
• [61:02] – The anxiety and humor of screwing up on set (“First take, really?”)
• [63:18] – Creative playfulness within show production, enhancing friendships

Tone & Style

The conversation is heartfelt, vulnerable, and frequently laced with humor and self-deprecation. Both Jacoby and Greenfield share deeply personal stories while bantering about their respective neuroses, proving that vulnerability and comedy can coexist in discussing life's hardest (and best) moments.

For Listeners

This episode is an engaging, often funny, but ultimately moving exploration of resilience, the messiness of creative careers, the power of support and community, and the profound effect of embracing joy and discovery—in art, in work, in parenthood, and in life.

Recommended for:

• Anyone feeling uncertain about their own unconventional path
• Creatives struggling with self-doubt or impostor syndrome
• Fans of "New Girl," Mike Schur's oeuvre, or Max Greenfield
• Those interested in honest talk about family, gratitude, and growth

Listen on your favorite podcast app, or catch “Man on the Inside” on Netflix.