Caleb Pressley | This Past Weekend w/ Theo Von #686

Episode Overview

• Comedian Theo Von and Sundae Conversation host Caleb Pressley explore how internet personalities navigate modern culture, viral misinformation, the college football NIL era, and independent business ventures while maintaining genuine human connection.
• The conversation weaves through personal anecdotes—including Caleb living in a Florida retirement community, a joint DJ set at Stagecoach, and a near-fatal medical emergency—while examining how small daily choices compound over a lifetime.
• Theo and Caleb conduct real-time fact-checks on viral political clips, popular urban legends, and medical claims, investigating topics ranging from the gut-brain connection to the alleged link between acetaminophen and autism.
• The episode highlights the transition from creator content to entrepreneurship, detailing Caleb's independent media company and his equity ventures in the beverage and footwear industries.

Key Concepts

• The Compounding Groove of Micro-Decisions: Caleb theorizes, based on living in a 200-unit 50+/65+ retirement building north of Boca Raton, that a lifetime of small choices wears people into a permanent psychological groove. By old age, there is no middle ground: individuals have either compounded decades of grumpy decisions into total bitterness or compounded kind decisions into becoming the happiest people alive.
• The Enteric Nervous System ("Second Brain"): While Caleb initially claims that 30% of the human brain is in the stomach (hedging to check if it is true before retracting it), live research clarifies that 0% of the actual brain is in the stomach. However, the gut contains a separate network of 100 million to 600 million neurons—comparable to the brain of a cat or fruit bat—known as the enteric nervous system, which produces 90% to 95% of the body's serotonin.
• Evolving Incentives in College Football's NIL Era: Name, Image, and Likeness (NIL) funding has shifted athlete priorities from pure competition to asset protection. Theo notes that Vanderbilt called him asking for NIL money to fund two white wide receivers (which he declined), while Caleb predicts that just as players sit out bowl games to protect NFL draft stock, players at smaller programs like Mississippi State will soon sit out the remainder of a season after two great games simply to protect their transfer portal NIL value for a bigger program like Alabama (though Theo hedges that two games would not be enough).
• Evaluating Confounding Variables in Medical Claims (Circumcision, Tylenol, and Autism): In response to a C-SPAN clip of Robert F. Kennedy Jr. and Donald Trump claiming early circumcision and Tylenol double autism rates, the hosts examine the underlying data. Newborns are typically circumcised within 1 to 2 days of birth, reducing first-year urinary tract infection (UTI) risk from 1 in 100 (uncircumcised) to 1 in 1,000 (circumcised). While a small 2016 observational study by Stephen T. Schultz and Georgianna G. Gould noted ASD regression in 38% of cases and an association with pediatric acetaminophen use, it could not prove causation due to confounding factors like genetics and illness severity. A 2024 JAMA study of over 2 million Swedish children found that when comparing full siblings to control for genetics and environment, the association between maternal acetaminophen use and autism disappeared entirely (a hazard ratio of 0.98), a finding reinforced by a 2026 systematic review and meta-analysis.
• Foundational Gastroenterology via Gastric Fistula: The foundational medical discovery that human digestion is primarily a chemical process rather than a mechanical one stems from an accidental shooting on June 6, 1822. When 19-year-old French-Canadian voyageur Alexis Bidagan dit St. Martin was shot in the stomach at close range on Mackinac Island, U.S. Army Surgeon William Beaumont kept him alive for 17 days via nutrient enemas until the wound healed into a permanent hole (gastric fistula). Between 1825 and 1833, Beaumont conducted 238 experiments by lowering food on a silk string into St. Martin's stomach and pulling it out to observe digestion.
• Ethical Controversies in Anatomical Plastination: Theo highlights how science and entertainment can cross ethical boundaries, citing a 2004 Der Spiegel exposé on Dr. Gunther von Hagens' Body Worlds exhibition. After establishing a plastination lab in Dalian, China in 1999 near three prison camps, von Hagens was found possessing corpses of Chinese citizens—at least two of which had bullet holes in their skulls suggesting execution—forcing him to return 7 corpses to China and cremate others.
• Consumer Market Mismatches and Creator Entrepreneurship: Both hosts disclose various business ties—Theo is sponsored by PrizePicks (promo code TPW) and Quo (quo.com/theo), while Caleb runs Sundae Conversation (independent for 1.5 years) and is a partner in Chica Chida and Stoke. Caleb explains that successful consumer products solve overlooked market gaps: Chica Chida peanut butter tequila is 100% allergen-free (containing no real peanuts) and scaled across ~33 states (with Wisconsin as its largest market) to reach its 1,000,000th bottle sold within 3 years of launching in New Jersey; similarly, his shoe brand Stoke targets the discrepancy that standard men's shoes are made in size D (narrow/regular) despite a study showing 75% of American men have wide feet (size E or bigger).

Quotes

• At 0:04:05 - "Apple's iPhone Center Stage feature allows your iPhone to automatically pan, zoom, and keep you centered in the frame during video calls and selfies, God." - Theo Von confirming why Caleb's stationary phone camera appeared to track him through a steamy shower door.
• At 0:10:49 - "I found out if you say this, people always will say yes. You say, 'I gotta ask.' And they're like, they're just curious about themselves. They're like, 'What is it? You gotta ask what?' And it's an in every time. 'I gotta ask.'" - Caleb Pressley sharing a street-interview technique learned from over a decade of approaching strangers.
• At 0:17:01 - "And my theory is, I feel like by that time of your life, you've made so many like small decisions about how you're gonna like approach stuff, that basically you just get so worn into those decisions that you're like slowly, every time you make a decision, you're slowly heading one direction, and 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, or you've made like kind of like nice person decisions your whole life, you've turned into like the happiest grandma or grandpa of all time." - Caleb Pressley explaining why residents in his Florida retirement community fell into two extreme emotional camps.
• At 0:19:52 - "Dude, we started as just a very small, it was like me and like four other guys, we like launched in New Jersey, that was like our launch state, and we've been kind of matriculating state by state. I think we're in like 33 states now, but that was three years ago when we did that, and we're, this year we're gonna sell our millionth bottle." - Caleb Pressley detailing the growth metrics of his allergen-free peanut butter tequila brand, Chica Chida.
• At 0:28:34 - "An oppressive heat dome centered over Tennessee in mid-September 2026 drove temperatures to record-breaking levels, making the atmosphere above the state temporarily taller and hotter than the air over the Sahara Desert." - Theo Von reading an AI overview about a record-breaking Tennessee heat wave where the atmosphere's midpoint rose to 19,465 feet.
• At 0:29:03 - "Nashville, Tennessee gets more rain than Seattle, Washington. 47 to 50 inches verse 37 to 38 inches." - Caleb Pressley verifying a counterintuitive geographical weather statistic.
• At 0:34:43 - "Well, they wanted NIL for two white guys. I'm like, two more white guys? Uh-uh. At least get one of those Japanese kickers, I'll fucking put in on that." - Theo Von recounting why he turned down a request from Vanderbilt University to contribute to their NIL collective.
• At 0:37:09 - "Zero percent of your actual brain is in your stomach, but your gut contains a separate network of about 100 to 600 million neurons known as the enteric nervous system." - Theo Von fact-checking Caleb's long-held belief that 30% of the human brain is located in the stomach.
• At 0:37:57 - "Many airline pilots, flight attendants, and air traffic controllers are part of the furry community. Lord help us. It's terrifying when you think about this. When you walk onto a commercial flight, it's possible that the pilot flying your plane could have a deranged fetish of dressing up like an animal. You can't make this up." - Sen. Tommy Tuberville in a C-SPAN2 Senate floor clip, which Theo later notes was presented without any evidence or source.
• At 0:44:33 - "When are we gonna see the first player pop off for like, I hate to say it, but like Mississippi State, the quarterback from Mississippi State, when are you gonna see him sit out the rest of the season, not to go to the NFL to protect his NFL value, but to protect his transfer NIL value to go to Alabama?" - Caleb Pressley predicting the next evolution of player opt-outs in college football.
• At 1:02:36 - "We made our set, but we made it beforehand, because we don't know how to DJ. And that was one of the biggest drawbacks of DJing the event is we didn't know how to do it." - Caleb Pressley admitting that Rob from Lost Kings pre-made their "Tonkin' Honkies" DJ set at Diplo's Stagecoach event in front of 9,000 people inside and 5,000 outside.
• At 1:11:38 - "There's two studies that show children who are circumcised early have double the rate of autism, and it's highly likely because they're given Tylenol." - Robert F. Kennedy Jr. in a C-SPAN Cabinet meeting clip discussing pediatric autism rates.
• At 1:11:55 - "But you know, there's a tremendous amount of proof or evidence, I would say, as a non-doctor, but I've studied this a long time." - Donald Trump responding to RFK Jr.'s claims during the same Cabinet meeting clip.
• At 1:14:40 - "Circumcised baby boys are significantly less likely to develop a UTI in their first year of life. An uncircumcised baby boy has about a 1 in 100 chance of getting a UTI, while circumcised has about a 1 in 1,000 chance." - Theo Von reading medical statistics from the American Academy of Pediatrics and CDC regarding newborn circumcision.
• At 1:16:52 - "In our own data, regression was featured in 38% of cases, and we were able to show an increased likelihood for ASD from acetaminophen use, which was higher in children with regression." - Theo Von reading from the 2016 observational study by Schultz and Gould before contrasting it with a 2024 JAMA sibling study of 2 million children that showed no causal link.
• At 1:30:43 - "They have autism. They don't understand an emotional edge of things. They don't understand it. So of course the businesses they create, they're not factoring any like, a lot of human emotion into it." - Theo Von discussing why certain tech founders build platforms and AI futures devoid of emotional warmth.
• At 1:32:44 - "If anything, while it's available, we should take advantage of it, because it's still 100% available to have real human connection, not be a part of this scary future, which could happen, it could not, but it could, but like right now it is 100% still available to be like a real living human with real human experiences." - Caleb Pressley emphasizing the importance of logging off social media to engage in real-world friendships.
• At 1:40:57 - "It was a seven-minute drive to Vanderbilt, and it was five minutes to Saint Ascension, and I was like, I'm going to Saint Ascension. And bro, I was there on an intubator for four days." - Caleb Pressley recounting how choosing a hospital based on a two-minute Uber difference during a swallowing emergency led to four days of intubation.
• At 1:42:55 - "He tied pieces of food to a string and lowered it down into his stomach, and then he'd pull it out and see how much had been digested. And he didn't do this just one or two times, he did it over 200 times. And his work helped establish that digestion was largely a chemical process, and it became foundational to the study of the stomach." - Shawn Reed (@Life on the Pond) explaining William Beaumont's 238 digestion experiments on Alexis St. Martin.
• At 1:58:32 - "This is a real stat because I've seen the study: is 75% of American men have wide feet. 75% of men in America. And so like a regular shoe is not a wide shoe. It's just a regular narrow shoe, like a regular shoe is a D, a size D. A wide shoe is a E. 75% of men in America should be in an E or bigger." - Caleb Pressley explaining the anatomical data behind his wide-fit shoe company, Stoke.

Takeaways

• Step away from outrage algorithms to reset your mental perspective: Spending even 20 minutes on platforms like X can induce a lingering, multi-day sense of dread about the future; immediately counter this by logging off and doing simple, present-moment activities with friends, as genuine human connection remains 100% accessible.
• Use curiosity hooks to initiate conversations: When approaching strangers for interviews, networking, or conversation, open with the phrase "I gotta ask" to trigger their natural curiosity and self-interest, almost guaranteeing they will engage.
• Audit your daily micro-decisions for long-term emotional compounding: Treat small daily choices in how you react to minor annoyances as investments in your future personality, consciously choosing kindness over bitterness so you do not wear yourself into a permanent grumpy groove by old age.
• Fact-check long-held "trivia" and viral political claims in real time: Do not repeat unverified claims—whether personal myths (like 30% of the brain being in the stomach) or sensational political speeches (like commercial pilots being furries)—without checking primary sources and scientific consensus.
• Look for sibling-controlled studies when evaluating medical headlines: When encountering alarming health claims (such as acetaminophen causing autism), look beyond small observational studies to large-scale sibling-comparison studies and meta-analyses that control for family genetics and environmental confounding.
• Prioritize hospital capability over minor transit time in medical emergencies: During an acute health crisis, do not bypass a premier university medical center (like Vanderbilt) for a smaller local hospital just to save two minutes in an Uber.
• Disable or verify automatic camera tracking features if you value privacy: Be aware that Apple's "Center Stage" feature on supported iPhones automatically pans and zooms to keep you centered during FaceTime calls—even through steamy shower glass—and adjust your settings accordingly.
• Over-prepare and secure expert backup when stepping outside your skill set: If you agree to a high-stakes performance outside your expertise—like Theo practicing a vocal part ~176 times for Stagecoach or Caleb and Theo DJing for 9,000 people—pre-plan the material with professionals (like Lost Kings) and keep an expert (like Diplo) on stage to handle technical failures.
• Verify foreign-language brand names before launching a company: Always run proposed business names through translation tools yourself rather than trusting a co-founder's slang translation (e.g., discovering Chica Chida translates to "cool girl" rather than "cool bitch").
• Build consumer businesses around overlooked anatomical or dietary realities: Look for massive, underserved market gaps where industry standards ignore consumer reality, such as formulating peanut-free peanut butter spirits for allergen safety or manufacturing size E+ wide shoes for the 75% of American men who do not fit standard size D footwear.
• Track personal habit streaks openly to maintain accountability: Whether taking a break from pornography (like Theo's 52-day streak) or changing digital habits, keep a clear count of your progress and discuss it candidly with trusted friends to reduce stigma and stay grounded.
• Protect your leverage and value in rapidly changing markets: Taking a cue from college athletes navigating the NIL transfer portal and creators taking their media companies independent, recognize when your market value peaks and structure your contracts or career moves to retain ownership.