Caleb Pressley
Interviewer, content creator and host of Sundae Conversation
Caleb Pressley (Interviewer, content creator and host of Sundae Conversation) has appeared as a guest on 1 episode in TMT. Topics they speak about most include Lane Kiffin, Social media and self-presentation, Stoke shoes.
In their words
Positions and remarks grouped by topic, each with the exact quote and where it was said.
Lane Kiffin
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:57:40
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:56:48
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:53:52
Other remarks
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:58:31
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:42:03
Social media and self-presentation
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:32:32
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:32:32
Stoke shoes
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:59:36
Circumcision and autism claims
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:13:36
Stagecoach Festival DJ set
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 1:03:45
2026 FIFA World Cup
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 48:03
College football and NIL
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 45:03
Tommy Tuberville furry community claim
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 54:43
Chica Cheetah
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 20:05
Man-on-the-street interviews
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 10:49
Aging
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”
This Past Weekend w/ Theo Von: #686 - Caleb Pressley (Sep 30, 2026) · Listen from 17:09
Appearances
#686 - Caleb PressleyThis Past Weekend w/ Theo Von · Sep 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.
Often appears with
- Theo Von · 1 shared episode