Staying Alive with Jon Gabrus & Adam Pally

Episode: Output Vs Input (w/ Jake Woolf)

Release Date: February 19, 2026
Guest: Jake Woolf
Producer: SmartLess Media

Episode Overview

This episode of "Staying Alive" features fashion writer, influencer, and lifewear enthusiast Jake Woolf, who joins hosts Jon Gabrus and Adam Pally for a candid and fun conversation about personal style, fashion’s influence on self-esteem, balancing creativity with content demands, and the realities of being a modern "taste-make," especially in the menswear world. The discussion weaves between lighthearted anecdotes, deep reflections on authenticity, and broader questions about how people approach dressing, creativity, and mental health as part of staying "alive" in every sense.

Key Discussion Points & Insights

Spontaneous Guesting and Social Media Connections

• Jake was a last-minute guest, stepping into a podcast slot and a lunch date at the same time.
• The hosts discuss the awkwardness of "knowing" people via Instagram, and the blurred lines between real friendships and digital acquaintances.
  • Notable quote:
    "I feel like I've seen... Now I gotta, like, follow up and just know a little bit more about him for real."
    — Adam, on social media friendships (01:21).

Early Fashion Memories and Personal Style Evolution

• Jake reflects on how, even as a little kid, costumes gave him an early understanding of the link between how he dressed and how he felt or was perceived (03:17–04:25).
  • Jake’s words: "Remembering that feeling...if I wear something that's cool, like, I'll sort of get attention or...people will want to talk to me" (04:09).
• The trio swap stories about their teen style identities—Adam’s skate-and-surf, Jon's grunge, Jake’s J.Crew-infused preppy look (05:08–06:25).
  • Funny moment: Adam dreams aloud of wearing a J.Crew gray roll neck sweater to impress the "Belles" of school (09:14–09:49).

Social Pressures and Self-Expression as a Young Man

• Adam and Jon open up about the judgments and sometimes homophobic taunts directed at "stylish" boys in their eras, with Jake admitting it was tough, especially commingled with being a musical theater kid (14:22–15:14).
  • "If you liked anything too much that you would get called [gay]...It didn't matter." — Adam (15:25)
• The guys agree that having the ability to express yourself authentically through clothes is important for confidence and mental health.

The Work of a Modern Fashion Writer/Influencer

• Jake shares the realities of content creation—balancing exclusives, picking the right format (video or writing), and resisting the relentless push from platforms for "more" (20:58–22:58).
  • "The nature of Instagram wants you to feel that way. Like, hey, cool post, where's the next one? And they're like, wake up Jake, it's time for another post." — Jake (22:13)
• Discussion explores the joy (and minor exhaustion) of being asked for style advice at parties or online, and how this compares to the classic “tell me a joke” request for comedians (26:06–27:56).
  • "It's like being a doctor at a party...There's a man, The Rock, is in the front. Does anyone have size 15?" — Jon (27:03)

Authenticity: Dressing for Yourself vs. Dressing for the Internet

• Jon explains his journey from seeing clothes as a chore to embracing style that feels authentic—citing his love for "Tevas or some whack shit like that," and the liberating advice from Adam to wear what feels good, not just what's "in" (24:52–25:45).
  • “If you like bright colors and that’s what you want to wear...that’s going to do better for you than anything that is quote unquote stylish.” — Adam (24:56)
• The crew grapples with the reality that even as a "taste-make," Jake must strike a balance between personal taste, audience expectation, and the exploitative "endless novelty" grind of social platforms.

Mental Health and "Staying Alive" Rituals

• Jake’s main wellness strategy: Therapy. He talks openly about weekly sessions, how his therapist is always available, and the importance of keeping mental health routines flexible (29:28–30:16).
  • “A big one is therapy. I do therapy to stay alive.” — Jake (29:38)
• Walking—especially in Central Park for Jake, and hiking for Adam and Jon in LA—is praised as both exercise and a potent mental reset (32:24–34:11).
  • “You sort of hit a groove and just mentally...you could be listening to a podcast...taking [the dog] through Central Park...good for the body and the mind.” — Jake (32:30)

Navigating Output vs. Input: The Creative Cycle

• The hosts and Jake discuss the dangers of too much "output" (daily posting, viral chasing), and not enough "input" (living, learning, experiencing).
  • "We're kind of talking about output versus input at this point...at some point you have to be putting fuel in there." — Adam (39:27–40:09)
• They reflect on the ways some creators lose their original passion, shifting from authentic voice to whatever content grabs attention (40:09–40:34).
• Jake prefers Substack as a more sustainable, direct connection to a genuinely interested audience, not shortcut by algorithms or viral trends (37:29–38:32).

Trends, Tastes, and the State of Men’s Fashion

• Jake champions the rise of small independent designers and responsible consumption, highlighting favorites like Evan Kinora and boutiques like Venspace (42:12–43:06).
• There's a shared satisfaction in supporting local crafts and knowing precisely who benefits—a more ethical, rewarding shopping experience (44:16–45:00).
  • "For me, shopping...feels better to be like, oh, I'm, you know, giving money to this guy who has this one store in Brooklyn, and then in turn, he's buying clothes..." — Jake (44:42)

Role Models and the Career Arc

• Jake underscores the importance of designers like Aaron Levine, who model the path from working at big brands to forging independent, authentic creative identities.
  • "He seems to be nailing it on all fronts...the way that he's been able to...go out on his own and build his own path is also something that...I really admire." — Jake (46:20)
• Adam and Jon point out the parallels with their own comedy/entertainment careers: grinding in obscurity before gaining autonomy to create work true to their own sensibilities (50:08–50:46).

Notable Quotes & Memorable Moments

• On Social Media Friendships:
  “If I ever run into the guy, I’m going to feel uncomfortable.” — Adam (01:50)

• On the Ritual of Personal Style:
  “Remembering that feeling...if I wear something that's cool, like, I'll sort of get attention or...people will want to talk to me.” — Jake (04:09)

• On Parental (and Societal) Judgments in Youth:
  “If you liked anything too much that you would get called [gay]...It didn't matter.” — Adam (15:25)

• Content Creator Struggles:
  “The nature of Instagram wants you to feel that way... Like, hey, cool post, where's the next one?...They’re like, wake up Jake, it's time for another post.” — Jake (22:13)

• On Finding Style Confidence:
  "If you like bright colors and that's what you want to wear and you feel good in it, then that's going to do better for you than anything that is quote unquote stylish." — Adam (24:56)

• The Centrality of Walking:
  "You just sort of hit a groove...walk through Central Park...good for the body and the mind." — Jake (32:30)

• On Output vs. Input:
  “We’re kind of talking about output versus input at this point...at some point you have to be putting fuel in there.” — Adam (39:27)

• On Small Brands and Conscience:
  “It just feels like, for me, shopping...feels better to be like, oh, I’m…giving money to this guy who has this one store in Brooklyn, and then in turn…he’s buying clothes from this one guy in Queens making the clothes.” — Jake (44:42)

Timestamps for Key Segments

• The Spontaneous Guest and Social Media Friendship — 00:47–02:14
• Early Fashion, Style in Youth, and High School Stories — 03:17–06:25
• Influence and Confidence: From “Uncool” to Style Inspiration — 10:03–10:56
• Content Creation, Publishing, and Mental Exhaustion — 20:58–22:58
• Authenticity: How to Dress for Yourself — 24:52–25:45
• Therapy and Walking as Wellness Habits — 29:28–34:11
• Output vs. Input in Creative Work — 39:27–40:34
• Men’s Fashion Now: The Indie Designer Wave — 42:12–45:00
• Mentors, Models, and Building a Career as a Taste-Maker — 45:41–49:44
• Closing Reflections on Passion as the Key to Health — 54:41–56:18

Closing Thoughts

Gabrus and Pally wrap the episode with reflections on passion—how having a genuine, sustaining interest (in clothes, comedy, neuroscience, or anything) keeps you "alive." For Jake Woolf, style is both self-expression and self-care; for the hosts, that lesson stretches well beyond menswear.

Summary by PodcastSummarizer.AI
For listeners new and old, this episode delivers laughter, sharp cultural criticism, and valuable life advice—whether you're getting dressed, recording a podcast, or just taking a walk.