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Tim Weichselbaum is a media mogul, comedian, podcaster and karaoke singer from Chicagoland. He is also his own agent, promotor, hype man, bodyguard, and driver (despite having epilepsy). Some day he will be a massive success. Or, he’ll stop doing it altogether suddenly, before becoming anything. That will be awfully embarrassing, considering some of the things he says about himself on this podcast. I don’t think there is a more self-confident person in the Austin comedy scene right now than Tim Weichselbaum. His whole act depends on it. He doesn’t do corny jokes about how he hates himself, and that is what makes him stick out compared to most comics. Very recently treated for crippling symptoms of ADHD, he is now in the process of becoming the super-comedian he always knew he had in him. All it took was doing this podcast about fifty times before he discovered that untreated ADHD was the only thing stopping him. This podcast is not just meant for entertainment or even necessarily to be consumed. It is a journey. A document of a short man’s long life. Should someone ever write a biography about Tim Weichselbaum, be rest assured that this podcast will be the most quoted source. Unless it’s a really sh*tty biography. Tim is an introvert. He rarely commits to friendships with anyone, and that is why he lives in a hobbit hole in near total isolation. Sure, he doesn’t scoff at the idea of interpersonal relationships, but it just isn’t a priority for him. He’s more invested in himself at the moment. When he finally reaches his full potential, then it will be time to start finding the real kind of friends and family he’s look for. Topics covered on the show primarily revolve around becoming a professional stand-up comedian, and the trials and tribulations that go along with that process. It took Tim ten years to decide if he was really good enough to be an entertainer. He isn’t just a stand-up comedian after all, he also can sing, dance, and act. But does Tim believe in himself? Let’s find out on this show. He also covers other interests such as mental health, self improvement, and finance/investing. He performs stand-up comedy in real life using the stage name Timmy Gusto, as an attempt to conceal the fact that he’s slightly Jewish. I wonder if it’s possible to get canceled from iTunes just for the description. Any who, you can follow @TimWeichselbaum on Instagram, his current social media platform of choice, to see reels and other enjoyable snippets of his creative output.

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Check latest episodes from The Tim Weichselbaum Show podcast

Ep. 123 | The Passion of the Crypto Bro

2026/09/22

Tim returns to revel in the financial ruin of a crypto-gaming YouTuber who accidentally created a $2 million tax liability right before the rest of his portfolio cratered. It serves as a beautiful cautionary tale about the perils of tech-stock hubris, tax drag, and the delusion of infinite money. Along the way, the monologue covers why Warren Buffett only reads annual reports for the prose, the crushing disappointment of learning Jeffrey Epstein was just a glorified tax evader instead of a trading wizard, and why universal basic income is just trickle-down economics for people who refuse to climb a telephone pole in a thunderstorm. Ultimately, if you are complaining about billionaires while refusing to utilize a Roth IRA, you deserve your tax drag. As Tim explains, Jesus won't endorse your life or your portfolio anyway, and if you ignore basic tax-advantaged compounding, the dead-eyed ghost of Patrick Swayze will just silently watch you descend into financial hell. Watch on YouTube: https://youtu.be/STvzwlAATYU

Ep. 122 | Materialism is for Amateurs

2026/09/14

Tim dismantles the amateur delusion of an objective, material world that exists independently of the observer. The reality is far less comforting: ontology and epistemology are identical, meaning nothing actually exists until you bother to measure it. From the physical illusion of solid walls that are actually just probability clouds, to space-time as a single coin with only one side, the basement of existence isn’t physical matter crashing together like bumper cars—it’s just indifferent mathematical equations running logic in an unanchored vacuum. Watch on YouTube: https://youtu.be/fUX7DA37Zx8

Ep. 121 | From Feudalism to FinTech

2026/08/26

This episode starts with an explanation of human trafficking and extracting materials like teeth and molecules from bodies. The topic then shifts to finance and retail trading. Tim talks about his work as a vibe coder building an options screener app and why he looked into getting a Series 65 license to give investing advice. He discusses a trading strategy he calls the flexi-wheel for peeling out of credit spreads. The episode also covers how the modern class system relies on net worth and cash flow instead of titles, comparing it to feudalism. It ends with a discussion on short-term capital gains taxes and trading Japanese stocks to access another market session. Watch on YouTube: https://youtu.be/a2tuGsKg8ic

Ep. 120 | Resevoirs Are Glorified Puddles

2026/07/16

Tim dusts off his analog gear once a financial quarter to deliver another highly esoteric monologue. This time, he goes on an impassioned rant exposing the dark truth about reservoirs, arguing they are just glorified, man-made puddles full of rotting trees that could never compare to natural lakes. The episode then pivots to the absurdities of the music world, examining the uncomfortably high barrier of entry for playing the flute and why The Beatles were smart to avoid it. Finally, Tim questions Louis C.K.'s claim that he doesn't do comedy for audience approval, sharing his own blunt thoughts on the true motivations behind stand-up before unceremoniously signing off for the rest of the quarter. Watch on YouTube: https://youtu.be/CdNSphoDN-w

Ep. 119 | Using Statistics to Justify Bigotry

2026/05/26

This episode consists of a continuous monologue that begins with an explanation of why the host deliberately mispronounces his own last name. The conversation then moves into a series of unfiltered personal theories regarding genetics, human sociology, and the nature of physical laws like friction and gravity. It also covers the host's experiences with long-term sobriety, including the lingering post-acute withdrawal symptoms of quitting weed and how a depleted baseline of dopamine has altered his daily outlook. In the second half of the episode, the focus shifts to financial markets and personal trading strategies. The host details a recent failed attempt at building an automated SPX trading program and the psychological challenges of managing a stock portfolio. He explains how his preference for the instant gratification of selling credit spreads and covered calls ultimately led to significant missed profits during the recent artificial intelligence market boom. Watch on YouTube: https://youtu.be/GQjDzyU0IgY

Ep. 118 | Society is Built for Addicts

2026/03/01

If you're the kind of person who likes to go kayaking, hit up a coffee shop, and dabble in the ukulele, you're obsolete. Society isn't meant for well-rounded people with varied hobbies anymore. It's designed specifically for isolated addicts who engorge themselves to the point of losing their relationships. We also get into the afterlife bureaucracy. Social hierarchies absolutely follow you when you die. If you don't have any earthly clout or a few billion dollars to grease the wheels, get ready to sit in a purgatory waiting room for 80,000 years just because they don't know who you are. Other stuff I talk about: vibe-coding an options trading algorithm with GPT-5.2 , losing tens of thousands of dollars on 0 DTE SPX trades , why DJs are going straight to hell even if they cure diseases, and why people who complain about "bad takes" are nobodies. Watch on YouTube: https://youtu.be/OoKM7i9pTq0

Ep. 117 | Bullish on Soup

2025/12/08

In this episode, we open up by checking in on the psychology of the elite and the Jeffrey Epstein files, before pivoting to a lesson on inflation and vocabulary: if you only have $45 million, you aren't a millionaire—you are just a "thousand-thousandaire". Later, we tackle the branding crisis of the cosmos. "The Solar System" is a boring name, and we investigate whether the galaxy owes trademark royalties to the Mars candy company for the use of "Milky Way". We also brainstorm better corporate sponsors for the universe, like Nabisco or Chiquita. Finally, we get into the "guru" section. I give an update on my trading app, OptionsAware, which "still sucks" but helps me rank daily opportunities. I explain why I'm selling puts, hedging my bets, and why—despite everything—I remain incredibly bullish on Campbell's Soup. Watch on YouTube: https://www.youtube.com/watch?v=qt85u2Dmoro

Ep. 116 | For the Pain of the Game

2025/11/05

After battling through numerous false starts, Tim records this episode while feeling "rusty" and dealing with a headache, jaw pain, and debilitating fatigue. This episode is a candid look at the grind of a solo developer, the frustrations of building a new product from scratch, and the personal toll it takes. Watch on YouTube: https://www.youtube.com/watch?v=xHM_I8eCz74

Ep. 115 | From ALS to AI Stocks with Mike Dragon

2025/09/22

Tim is back! After more than a month away developing a new app, he returns for Episode 115 with guest Mike Dragon for a sprawling, deep-dive conversation. The discussion starts with a surprisingly frank and personal look at ALS disease before spiraling into a grand theory of everything, where Tim posits that all complex systems—from DNA and viruses to Bitcoin and financial markets—are fundamentally a form of language. From there, they dissect the psychology of wealth, recent political events, the culture of the Austin comedy scene, and the intricate details of Tim's new FinTech application. Watch on YouTube: https://www.youtube.com/watch?v=G1940gPwvmY

Ep. 114 | Semantic-Phonon Condensate

2025/07/24

This was a pseudoscience-heavy episode where I lean heavily into the ChatGPT psychosis I've been cultivating for over a year. It was a long episode where I introduce a hypothesis on intracellular communication, which could possibly shed light on ALS and other neurodegenerative diseases. At least that's what I'm telling myself to feel like I'm doing something important. Watch on YouTube: https://youtu.be/EumCuHWGHQw

Ep. 113 | A Thousand Songs on One Soap Bar

2025/06/16

This episode kicks off with a take on marketing — not as a weakness, but as something Tim believes he could excel at, if only he had a product worth pushing. That launches a long-form, semi-improvised dive into the mind of Steve Jobs: not just the public myth, but the obsessive, detail-driven version that cared as much about keynotes as he did about hardware. There's admiration here, but also satire, with a focus on why Jobs' ideas actually landed — and how most people completely miss the point. From there, the monologue expands into a chaotic but intentional meditation on logic, genius, and cultural mythmaking. Van Gogh becomes a case study in misunderstood brilliance. Jesus is examined as a PR story with missing context. Even Trump shows up, framed as someone who operates (however messily) according to internal logic. It’s loose, fast, and unapologetically nonlinear — but underneath the tangents, there’s a steady argument about what it means to speak truth in public. Watch on YouTube: https://youtu.be/s6NEM2q7Pio

Ep. 112 | Solving the Binding Problem

2025/06/01

In episode 112 of The Tim Weichselbaum Show, Tim dives deep into a complex neuroscience project he's spearheading. The project aims to experimentally test a hypothesis about how the brain unifies sensory information from different modalities, like vision and language, into a cohesive understanding. Tim explains that this in silico experiment utilizes fMRI data, computer modeling, AI, and machine learning to investigate where and how the brain creates a "unified semantic workspace." The core idea is that diverse inputs, such as watching a movie or listening to a story, are ultimately translated into a common "language" within the brain. Tim notes this interdisciplinary project draws on cognitive neuroscience, data science, computer science, and AI. He also suggests that understanding these fundamental brain processes could eventually contribute to research on brain disorders like Alzheimer's disease. Watch on YouTube: https://www.youtube.com/watch?v=d0P2NlZbVIc

Ep. 111 | Crashing Out as a Polymath

2025/05/05

So, Tim hit record for Ep 111 and just let his brain spill out. We're talking identity crises right out the gate, the weird science of music and reality, and the frustrating life of a "polymath" who knows a bit about everything (and isn't afraid to say it). He covers old business wins, why self-help gurus piss him off, the illusion of separation, and somehow ties racial realism to astrology (don't ask). It's chaotic, opinionated, maybe a little arrogant, but definitely honest. Basically, Tim processing the world in real-time. Give it a listen if you're up for the ride. (Warning: unfiltered language inside) Watch on YouTube: https://www.youtube.com/watch?v=GPR4VUQRRsQ

Ep. 110 | Meaning Between The Voids

2025/04/16

In this milestone 110th episode, Tim Weichselbaum takes a reflective break from his usual content format to look back on the podcast's journey over the past 3+ years. He shares his personal experience with sobriety and how quitting alcohol has transformed both his social interactions and creative process. The episode explores how alcohol previously served as a social facilitator in his comedy career and discusses the challenges of performing and connecting with audiences without it. Tim dives into his unique way of perceiving patterns and meaning in the world, touching on how his thought processes differ from typical approaches. Throughout the episode, he weaves in philosophical musings about semantics, reality, and how everything is defined by its distinctions from other things. He briefly explores scientific concepts like brain lateralization and information theory while acknowledging the burnout he's been experiencing from working on various intellectual projects. The conversation flows in a stream-of-consciousness style with personal anecdotes from childhood and his time in comedy, culminating in reflections on perception and the nature of reality. While Tim admits to feeling tired toward the end of the recording, he continues sharing his thoughts with the raw authenticity that longtime listeners have come to expect. Watch on YouTube: https://www.youtube.com/watch?v=6q_DXt0fNSs

Ep. 109 | Listen to Your Future Self

2025/03/31

You are currenty living in the future and past simultanously. You are receiving and sending messages to your future and past self subconsiously. Your best role model is your future self. The secret to reaching your goals in life is in learning how to honestly communicate with these two other parties, and doing so as often as possible. Watch on YouTube: https://www.youtube.com/watch?v=eu8n6Trt0JA