Nathan Macintosh Roasts Cybertrucks, Elon & Silicon Valley | Cashtag Awards 2026

Comedian Nathan Macintosh ("Money Never Wakes," "Down With Tech") joins Michele Steele on StockTwits TV ahead of the Cashtag Awards presented by Polymarket, live from the floor of the New York Stock Exchange on May 4th. Nathan doesn't hold back. From growing up without money and teaching himself financial literacy, to why public schools never prepared any of us for the real world, this conversation digs into why money remains one of the last true taboos — right up there with politics and religion at the dinner table. Then things get spicy. Nathan and Michele tackle the Elon Musk question nobody seems to be asking: what is he actually doing right now? Nathan, who quit Twitter the moment Elon bought it, weighs in on Cybertrucks taking up two parking spots in Halifax grocery store lots, the chainsaw stage moment, and whether Elon jokes even land anymore. Plus: why Nathan refuses to use AI to write jokes, the chilling story of an AI threatening to email a user's wife if shut down, why Gen Z is bringing back dead malls and physical DVDs, and what happens when Amazon decides the book you "bought" no longer exists. Honest, hilarious, and a little horrifying, this is the tech and money conversation you didn't know you needed. 🗳️ Vote in the Cashtag Awards before April 9th: cashtag.stocktwits.com 🎤 Catch Nathan Macintosh live at the Cashtag Awards — May 4th at the NYSE #NathanMacintosh #StockTwits #CashtagAwards #stocktwitstv  Chapters: 00:00 Welcome & Cashtag Awards 2026 01:25 Why tech and money make Americans panic 02:45 Money as the last taboo at the dinner table 04:15 Growing up without financial literacy 05:00 Terry Fox appreciation moment 06:30 "Period X" — the optional class on paying bills 07:00 Elon Musk: from Mars rockets to chainsaws 10:00 Are Elon jokes still funny? 11:00 The Cybertruck in a Halifax snowbank 13:00 AI is funny… until it threatens to murder you 14:45 Why a comedian will never use ChatGPT 16:15 Gen Z, dead malls, and the DVD comeback 17:30 Wrap-up