#686 - Caleb Pressley

Episode of This Past Weekend w/ Theo Von · September 30, 2026 · 2 h 8 min

Theo Von and returning guest Caleb Pressley riff on retirement-community life, Tommy Tuberville's furry claims, their Stagecoach DJ set, college football, and Caleb's business ventures.

Summary

Comedian Theo Von hosted interviewer Caleb Pressley, host of Sundae Conversation, for a loose, comedic conversation. Pressley recalled living in a 65-plus retirement building in Florida, where he developed a theory that old people become either very happy or very grumpy through a lifetime of small decisions. He described his peanut butter tequila brand Chica Cheetah, which he said launched in New Jersey three years earlier and was on track to sell its millionth bottle, and shared his trick for getting strangers to agree to street interviews.

The pair mocked a clip of Senator Tommy Tuberville claiming many airline workers are part of the furry community, with Von questioning why a senator would spend time on it and Pressley arguing such stories signal the world is in decent shape. They discussed SEC football and NIL, with Pressley predicting players might sit out to protect transfer value, and the 2026 World Cup, which Pressley found structurally uncompetitive and Von attributed partly to tournament expansion. Von told a story of convincing Rob Gronkowski that a drunk Australian at the World Cup final was the head of WME.

They recounted their Stagecoach DJ set at Diplo's honky tonk as the "Tonkin' Honkies," admitting they did not know how to DJ, and Pressley praised Von's performance with Ella Langley. Later segments covered a clip of Robert F. Kennedy Jr. and Donald Trump linking early circumcision and Tylenol to autism, which Von checked against published research; Von's speculation that tech leaders with autism are shaping an emotionless future, to which Pressley countered that real human connection remains available offline; the historical case of Alexis St. Martin and William Beaumont; and Lane Kiffin's coaching persona. Pressley closed by discussing his independent media business and gifting Von shoes from Stoke, a wide-foot shoe company he is involved with.

Chapters

0:00
Opening banter and the 'word escrow'
Von and Pressley joke about a mediator for unsaid remarks, phone cameras that follow users, and Glenny Balls's weight loss and food videos.
9:44
Street interviews and influencer culture
Pressley shares his 'I got to ask' trick for securing man-on-the-street interviews and they discuss everyone becoming an influencer.
12:52
Life in a Florida retirement building
Pressley recalls living among seniors near Boca Raton and his theory that old people become either very happy or very grumpy.
17:58
Chica Cheetah tequila
Pressley describes his peanut butter tequila brand's taglines, growth to 33 states, and approaching a millionth bottle.
28:02
Nashville and SEC football fandom
They discuss Nashville's weather and Von's multiple college football allegiances including LSU, Vanderbilt, Tennessee and Ole Miss.
37:51
Tommy Tuberville's furry claim
They play and mock a clip of Senator Tuberville claiming airline workers are furries and discuss media claims about unfounded claims.
44:38
NIL, the World Cup and a Gronkowski prank
Pressley predicts NIL-driven sit-outs, both criticize the 2026 World Cup, and Von tells of fooling Rob Gronkowski at the final.
59:37
The Stagecoach DJ set
They recount DJing at Diplo's honky tonk at Stagecoach without knowing how, and Von's onstage moment with Ella Langley.
1:11:37
Circumcision, Tylenol and autism
They react to an RFK Jr. and Trump clip linking early circumcision and Tylenol to autism and read research on acetaminophen.
1:30:21
Autism, technology and human connection
Von speculates tech leaders' lack of emotion shapes society, and Pressley describes how X makes him feel bad versus offline experiences.
1:39:12
Hospital story and Alexis St. Martin
Pressley recalls being intubated after choosing a closer hospital, and they watch a video on Beaumont's digestion experiments and Body Worlds.
1:50:07
Man rankings, Lane Kiffin and Stoke shoes
They rank current 'men,' debate Lane Kiffin and Curt Cignetti, and Pressley discusses his independent business and gifts Stoke shoes.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

Linked moment · 10:49Skip to 10:49 using a listen link in the info box.
Caleb Pressley
Pressley says the reliable way to get strangers to agree to a street interview is to open with 'I got to ask.'
“I found out if you say this, people always will say yes. You say, I got to ask”
Listen from 10:49 · Man-on-the-street interviews
Caleb Pressley
Pressley theorizes that people become either very happy or very grumpy in old age as a result of accumulated small decisions over a lifetime.
“you've done it so many times by that age that you've either made grumpy decisions your whole life and you've turned into a total grump”
Listen from 17:09 · Aging
Caleb Pressley
Pressley says Chica Cheetah launched three years earlier and expects to sell its millionth bottle this year.
“But that was three years ago we did that. And this year we're going to sell our millionth bottle”
Listen from 20:05 · Chica Cheetah
Theo Von
Von questions why Senator Tuberville is spending time on whether airline workers are furries.
“Who gives a shit, Tommy? Why are you wasting your time on this?”
Listen from 39:45 · Tommy Tuberville furry community claim
Theo Von
Von argues that media outlets criticizing Tuberville for unfounded claims have themselves made many unfounded claims.
“But first of all, every media outlet has made unfounded claims about absolutely fucking everything”
Listen from 42:27 · Tommy Tuberville furry community claim
Caleb Pressley
Pressley predicts college players will eventually sit out the rest of a season to protect their transfer NIL value rather than their NFL value.
“When are you going to see him sit out the rest of the season, not to go to the NFL and protect his NFL value, but to protect his transfer NIL value”
Listen from 45:03 · College football and NIL
Theo Von
Von argues FIFA expanded the World Cup field to grow its audience and build stars, which contributed to boring games with few upsets.
“The reason I think they did that was because they're trying to grow more of an audience”
Listen from 47:25 · 2026 FIFA World Cup
Caleb Pressley
Pressley says he enjoyed hosting the World Cup but finds soccer's structure, stoppage time and feigned injuries uncompetitive.
“but like the game itself to me, the way it's structured is super... It's almost like non-competitive at heart or something”
Listen from 48:03 · 2026 FIFA World Cup
Theo Von
Von recounts that at the World Cup final he falsely told Rob Gronkowski a drunk Australian guest was the head of WME.
“And I just made up that the guy was the head of this huge agency”
Listen from 51:39 · 2026 FIFA World Cup
Caleb Pressley
Pressley argues that trivial news stories like Tuberville's claim are a sign that the world is in a relatively good place.
“I think stories like this are like a sign that things are okay in the world”
Listen from 54:43 · Tommy Tuberville furry community claim
Caleb Pressley
Pressley admits that the biggest problem with their Stagecoach DJ set was that neither of them knew how to DJ, having pre-made the set.
“And that was one of the biggest drawbacks of DJing at the event is we didn't know how to do it”
Listen from 1:03:45 · Stagecoach Festival DJ set
Caleb Pressley
Pressley jokes in response to the Tylenol claim that one should avoid anything requiring Tylenol, including circumcision.
“But you shouldn't be doing anything that you need to take a Tylenol for, including circumcision”
Listen from 1:13:36 · Circumcision and autism claims
Theo Von
Von reads that a small 2016 observational study linked acetaminophen use in toddlers to autism but cannot show causation.
“a small 2016 observational study reported an association between acetaminophen use for fever in toddlers and autism, but its design cannot show that the medicine caused autism”
Listen from 1:19:43 · Acetaminophen and autism
Theo Von
Von advises against visiting too many places when traveling abroad because the transit ruins the trip.
“You try to do too many places, and it ruins it because you spend all your time traveling”
Listen from 1:23:42
Theo Von
Von claims many people driving technology businesses have autism and therefore build products that do not factor in human emotion.
“a lot of the people who are running a lot of these businesses who are forwarding technology and moving it into the future have autism, right?”
Listen from 1:30:21
Caleb Pressley
Pressley says using X quickly gives him bad feelings that can ruin a day or more.
“there's a the platform X to me is like, it's immediate, like, bad feeling. It gives me bad feelings”
Listen from 1:32:32 · Social media and self-presentation
Caleb Pressley
Pressley argues that genuine offline human connection remains fully available and should be taken advantage of.
“it's still 100% available to have real human connection, not be a part of this scary future, which could happen”
Listen from 1:32:32 · Social media and self-presentation
Caleb Pressley
Pressley recounts choosing a closer Nashville hospital over Vanderbilt when he could not swallow and being intubated for four days.
“I was like, I'm going to St. Ascension. And, bro, I was there on an intubator for four days”
Listen from 1:42:03
Theo Von
Von wonders whether Kiffin's celebrity walkouts risk making the program about ego rather than the team.
“I can't tell if you run the risk of things becoming more about ego and energy than they do about the team”
Listen from 1:53:24 · Lane Kiffin
Caleb Pressley
Pressley argues coaching success depends on players, citing that few Hall of Fame NFL coaches lacked a Hall of Fame quarterback.
“in the history of the NFL there's been I think maybe three total Hall of Fame coaches that haven't had a Hall of Fame quarterback”
Listen from 1:53:52 · Lane Kiffin
Caleb Pressley
Pressley says Kiffin's high-energy approach is not sustainable long term, though it currently makes college football fun.
“It's 100% not sustainable. You can't do that”
Listen from 1:56:48 · Lane Kiffin
Caleb Pressley
Pressley regards Curt Cignetti as a commanding, young coach likely to be a lasting force.
“I feel like Cignetti's like a monster looming in the corner who's young for coaches. He's going to be around for a while”
Listen from 1:57:40 · Lane Kiffin
Caleb Pressley
Pressley says his team is about a year and a half into being an independent media business and still figuring things out.
“Like, only a year and a half, really, into being independent”
Listen from 1:58:31
Caleb Pressley
Pressley claims, citing a study he has seen, that 75% of American men have wide feet, the market Stoke targets.
“This is a real stat because I've seen the study. It's 75% of American men have wide feet”
Listen from 1:59:36 · Stoke shoes

People

In the conversation

Theo VonAmerican stand-up comedian and host of the podcast This Past Weekend
Caleb PressleyInterviewer, content creator and host of Sundae Conversation

Discussed

Tommy TubervilleU.S. senator and former football coach Haywood accused of trying to overturn NIL
Glenny BallsCo-host of Sundae Conversation with Caleb Pressley
DiploAmerican DJ and producer mentioned in connection with Stagecoach
Rob GronkowskiRetired NFL tight end used as Goldsberry's aging analogy for Giannis
Robert F. Kennedy Jr.Health secretary whose appointment Jesse Kelly cited as coalition-building
Donald TrumpPresident of the United States whose conduct of the Iran war is the episode's main subject
Lane KiffinLSU football head coach, formerly at Ole Miss
Curt CignettiCollege football head coach
Josh HeupelHead football coach of the Tennessee Volunteers
Ella LangleyAmerican country singer-songwriter from Hope Hull, Alabama
Alexis St. Martin19th-century Canadian voyageur whose gastric fistula enabled digestion experiments
William BeaumontU.S. Army surgeon who conducted digestion experiments on Alexis St. Martin
Gunther von HagensGerman anatomist behind the Body Worlds plastination exhibitions
Andrew HubermanAmerican neuroscientist, professor at Stanford School of Medicine and host of the Huberman Lab podcast
Mike TysonFormer heavyweight boxing champion who fought Jake Paul

Topics

From the publisher

Caleb Pressley is an interviewer, content creator and host of the show “Sundae Conversation”. Caleb returns to talk about why he lives in a Florida retirement community, the ascension of Glenny Balls, and what went on behind the scenes at their Stagecoach DJ set. Caleb Pressley: https://www.instagram.com/calebpressley/ ------------------------------------------------- Tour Dates! https://theovon.com/tour New Merch: https://www.theovonstore.com ------------------------------------------------- Sponsored By: Celsius: Go to the Celsius Amazon store to check out all of their flavors. #CELSIUSBrandPartner @CelsiusOfficial https://amzn.to/3HbAtPJ Prize Picks: Go to ⁠https://link.prizepicks.com/LME0/TPW⁠ and use code: TPW Quo: Go to http://quo.com/theo for 20% off your first 6 months. Perplexity AI: Ask anything at https://pplx.ai/theo ------------------------------------------------- Music: “Shine” by Bishop Gunn Bishop Gunn - Shine ------------------------------------------------ Submit your funny videos, TikToks, questions and topics you'd like to hear on the podcast to: tpwproducer@gmail.com Hit the Hotline: 985-664-9503 Video Hotline for Theo Upload here: https://www.theovon.com/fan-upload Mail stuff to: ATTN: TPW PO BOX 40137 Nashville TN 37204 ------------------------------------------------ Find Theo: Website: https://theovon.com Instagram: https://instagram.com/theovon Facebook: https://facebook.com/theovon Facebook Group: https://www.facebook.com/groups/thispastweekend X: https://twitter.com/theovon YouTube: https://youtube.com/theovon Clips Channel: https://www.youtube.com/c/TheoVonClips Shorts Channel: https://bit.ly/3ClUj8z ------------------------------------------------ Producer: Zach https://www.instagram.com/zachdpowers Producer: Trevyn https://www.instagram.com/trevyn.s/ Producer: Nick https://www.instagram.com/realnickdavis/ Producer: Andrew https://www.instagram.com/bleachmediaofficial/ Producer: Halston https://www.instagram.com/halstonrays/ Learn mor…

Summary, chapters and key points were generated from the episode transcript on October 24, 2026. Quotes are checked word for word against the transcript.

Categories: Comedy Interviews·Football