Canal Street Dreams - Episode Summary

Episode Title: Joshua Topolsky Becomes a Sports Podcaster on C$D
Hosts: Eddie Huang & Natashia Perrotti
Guest: Josh Topolsky (co-founder of Vox, The Verge, and Outline, now at Sherwood)
Date: October 31, 2025

Overview

In this episode of Canal Street Dreams, Eddie and Natashia are joined by digital media veteran and Sherwood editor-in-chief Josh Topolsky for a conversation that veers from existential malaise, the realities of modern media, and political corruption to the deeply personal realities of relationships, parenting, gambling, and—more than anyone expected—sports fandom. Beneath the banter, the trio navigate how passions, compulsions, and love shape both their professional and private worlds.

Key Discussion Points & Insights

1. The State of the World and Political Corruption

• Opening Tone: The episode kicks off with sardonic banter about "pro-fascist views," immediately subverting expectations in classic Eddie & Josh fashion.
  • [00:21] Josh's Friend (Topolsky): “We’re living in very dark times... America is used to regular corruption... We are dealing with a different level... a different level of political and societal corruption at the highest levels right now.”
  • [01:19] Conversation about political radicalization in families since Trump.

2. Mental Health, Media, and the Rise of Podcasting

• Podcasting as Therapy: Both hosts and guest reflect on podcasting as a therapeutic outlet, especially for men.
  • [03:44] Josh Sapolsky: “Me doing a podcast is a sign that I’m not okay.”
  • [03:47] Topolsky: “That’s why there are so many, because we have a mental health crisis in this country.”
• The Struggles of Writing vs. Speaking:
  • [04:30] Topolsky: “I hate writing... when I have to sit down and try to organize the thoughts... Like, my brain feels all the time.”

3. Relationships: Passion, Hate, and the Sports Complex

• Dynamics of Desire & Resentment:
  • [06:03] Josh’s Partner (Natashia): “He’s undersexualizing me on a daily basis... I would like to be lusted for.”
  • [06:41] Topolsky: “The best passion has got a little bit of hate in it.”
  • [07:08] Natashia: “My hate is informed by how much you love sports.”
• Routine and Resentment Linked to Sports:
  • [07:10] Josh Sapolsky: “Monday to Wednesday, very nice. Thursday night football... silent treatment on Friday. Sunday comes along and it’s like, dude, I hate you. We beef, hot sex.”
• Sports Betting and Compulsion:
  • [09:00] Josh Sapolsky: “I bet on every game. If there’s a rec league down the street, I’ll watch it and put a regular game on my phone.”
  • [09:55] Natashia & Josh riff on high-stakes betting.

4. Fanaticism & Gendered Hobbies

• The Place of Sports in Identity:
  • [13:20] Topolsky: “This does not matter at all. These guys... will never change anything for me. If I just don’t pay attention, I don’t have to feel this horrible feeling.”
  • [14:30] Josh Sapolsky: “Sports teams are an extension of family community. That’s our team.”
• Reality TV vs. Sports – Gendered “Recreation”:
  • [14:34] Natashia: “I wish women had things like sports... the Real Housewives a little bit, or I guess like the Bravo universe... But sports is like... this thing that you guys go do.”
  • [18:06] Josh Sapolsky (about a hypothetical Housewives ‘Red Zone’ channel): “Imagine if they had red zone for reality TV Housewives…she’s about to throw a leg. She’s about to flip a table. Red zone for Housewives. Crazy.”

5. Compromise, Respect, and Taking Up Space

• Natashia’s Perspective:
  • [20:53] Natashia: “I have a problem taking up space... I grew up with just a vibe of... if my mom was listening to music, I just wouldn’t go in there and be like, we’re gonna listen to Doja Cat.”
  • [21:32] Josh Sapolsky: “She was dating dudes with self worth.”
• The Hidden Truth of Addictions:
  • [21:50] Natashia: “He was basically hiding his drug addiction from me...'
  • [22:41] Josh Sapolsky: “Honestly, the clues were there... 75% of my closet is nylon clothing, he may like sports.”
• Mutual Acceptance of Flaws:
  • [24:13] Josh’s Friend (Topolsky): "We’re really talking about relationships here is what we’re doing."
  • [24:21] Natashia: “You’ve accepted a lot of, like, insane things about me. Like, I want a $100,000 handbag.”
  • [27:08] Josh Sapolsky: “If you hit a six-leg parlay, you will feel just love, life, energy. Eat, pray, love.”

6. Consumerism, Capitalism, & The Search for Meaning

• Addictive Personalities and Dopamine Chasing:
  • [27:22] Josh’s Partner (Natashia): “It’s the immediate dopamine rush. And then it goes away. And then you’re like... I need another parlay. That’s why you have to keep laying parlays. That’s why I have to keep shopping every week.”
  • [27:35] Topolsky: “Sometimes cataclysmic happen, bro.”
• Material Obsessions:
  • [25:10] Topolsky: “I do get that now. I get that actually. A lot more than sports, in a way.”
  • [25:34] Topolsky: “Shopping is the American... pastime... For Americans, it’s shopping.”

7. Boundaries, Work-Life Balance & Public/Private Personas

• Appropriate Contexts for “Crazy Opinions”:
  • [32:22] Topolsky: “We need to return to a time when you can think it and not say it.”
  • [35:25] Josh Sapolsky: “I’m fine with people having crazy opinions. Have a crazy opinion in a group chat, at a barbecue... But in the public domain, social contract, be cool.”
• Media World Anecdotes:
  • [36:09] Josh Sapolsky tells the story of getting kicked out of TED for going on a risqué podcast with Asa Akira instead of networking with donors.
  • [38:46] Description of Sapolsky’s TED Talk and media attitudes.

8. Parenting, Family and Routine

• Integrating Sports, Friends, and Parenting:
  • [41:31] Topolsky prompts questions about including children in hobbies. Josh notes how his son enjoys the “homies” and the home-centric sports routine.
  • [42:22] Josh clarifies team allegiance (Commanders) and the code among sports gamblers.

9. Relationship Conflict & Communication

• Intimacy and Arguing Over Needs:
  • [48:19] Sapolsky: “They’re always just one of us feels that someone is doing something that makes them feel unloved. And all we have to do is just reconfirm... I do love you and I’m here.”
  • [49:23] Topolsky: “It is really hard to express what you really want... If I have to say it, then it doesn’t matter if I get it. Because, like, the fact that they didn’t know that I needed it is what is making me feel aggravated...”
  • [50:34] Natashia: “To be seen is to be loved. And sometimes we can lose sight of the little things with our partners.”

Notable Quotes & Moments (with Timestamps)

• On Corruption and Dark Times:
  • “We are dealing with a different level, I think, of… political and like, societal corruption at the highest levels right now.”
    — Josh's Friend (Topolsky), [01:19]
• On Mental Health and Media:
  • “Me doing a podcast is a sign that I’m not okay.”
    — Josh Sapolsky, [03:44]
• On Addictive Personalities:
  • “If you hit a six leg parlay, you will feel just love, life, energy. Eat, pray, love...”
    — Josh Sapolsky, [27:08]
  • “It’s the immediate dopamine rush. And then it goes away. And then you’re like, oh my god, I need a new one. I need another parlay. That’s why you have to keep laying parlays. That’s why I have to keep shopping every week.”
    — Natashia Perrotti, [27:22]
• On Public Discourse Boundaries:
  • “We need to return to a time when you can think it and not say it.”
    — Josh Topolsky, [32:22]
• On Relationship Needs:
  • “It is really fucking hard to one to like, experience that in yourself and to recognize it. But it’s also really hard to figure out a way to say to a person… this is the thing that is bringing me to this place.”
    — Josh Topolsky, [49:23]
  • “To be seen is to be loved. And like, sometimes I think we can lose sight of the little things with our partners, especially long term.”
    — Natashia Perrotti, [50:34]

Rapid-Fire Segment: “Five” Questions for Josh Topolsky [54:35–59:40]

• Best News Outlets?
  • Topolsky recommends The New York Times (“despite many problems”), Semaphore, and his own Sherwood for young market coverage.
    — [54:49 – 55:37]
• AI or Touch Grass (and sub-question about grooming):
  • Prefers moderation, “crank down our interest and reliance on AI in the ways that we’re using it right now… it’s not fully formed...”
    — [56:19]
• iPhone vs. Samsung:
  • Android gets the nod: “Android’s a better platform…more enjoyable and more useful.”
    — [57:22 – 57:30]
• Marry, F, Kill: Sam Altman, Elon Musk, Mark Zuckerberg:
  • Kill Zuck (“so much more subtle and… widespread [damage] than Musk”), marry or F Altman. “Musk has, like, a sly twinkle in his eye…”
    — [57:44 – 59:00]
• If you had to play and bet on a sport—what sport?
  • Basketball (tall, played before); F1 if not; enjoys basketball culture best.
    — [60:11–60:41]

Tone and Style

• The episode is unfiltered and humorous, characterized by rapid-fire exchanges, playful roasting, and deep honesty.
• The hosts’ and guest’s willingness to self-deprecate and share neuroses about relationships, addiction, and aging keeps the mood lively, even as serious points land about modern anxiety.

Key Takeaways

• Passion, obsession, and love are complexly intertwined in relationships—sports gambling and consumerism are just the surface manifestations.
• Modern media and politics feel broken, but finding meaningful escapes and honest conversations are pillars for maintaining sanity.
• Communication, boundaries, and mutual respect underpin long-term relationship health—even when fights are “horrendous.”
• Keeping it real is better than keeping to the script; authenticity, even chaotic, is the podcast’s north star.

Recommended Segments to Listen To

• Discussion of Modern Corruption & Diagnosis of “Dark Times”: [00:21–02:43]
• Sports as Proxy for Identity/Family: [13:20–15:11]
• Gambling Addiction and Big Bets Stories: [09:13–10:35; 27:08]
• Reality TV vs. Sports—Gendered Hobbies: [14:30–18:32]
• Communication and the Dynamics of Long-Term Relationships: [48:19–50:43]
• Rapid-Fire Q&A with Topolsky (Pop culture and Tech hot takes): [54:35–59:40]

Canal Street Dreams continues to deliver on its promise: real talk for grownups, creators, and anyone muddling through the modern condition with humor, candor, and a bit of chaos.