In this August 2026 First Fridays live stream, Jason and Jeff break down the latest earnings season chaos, exploring why Lemonade dropped despite hitting its lowest gross loss ratio ever. They analyze Twilio’s massive 35% post-earnings pop, debate whether The Trade Desk's open internet thesis is officially broken, and review their 2026 Portfolio Contest standings. Plus, the duo discusses Kinsale Capital’s underwriting discipline, speculative quantum computing plays, and potential market black swans.

00:31 Splitting Wood Talk

02:30 Podcast Intro Bits

03:28 Jeff Has Girl Hands

05:02 Show Agenda Setup

05:49 Market Vibes Check

09:36 Hydration Hat Jokes

10:25 Lemonade Earnings Breakdown

16:31 Twilio Pops Off

20:40 Juiced Earnings Debate

25:13 Short Interest Downturn Risks

26:47 Leverage Crash Scenarios

27:40 Rate Hikes and Inflation

29:33 Hair Dye Poll Break

32:34 Portfolio Contest Update

37:52 Trade Desk Postmortem

44:45 Surprising Contest Winners

47:19 Kinsale Insurance Debate

51:04 Quantum Computing Bets

54:44 Options Put Selling Rules

55:52 Poll Results and Sign Off

Companies mentioned: AFG, ALL, AMZN, APH, BRK.B, CRWD, DAVA, DDOG, GOOGL, IBM, IONQ, KNSL, LEN, LMND, MELI, MRNA, NOW, NVDA, PGR, PYPL, SOUN, TREX, TTD, TWLO, UPST

Find where to listen & subscribe, portfolio contests, and contact information at https://investingunscripted.com

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Listen to the Chit Chat Stocks Podcast for discussions on stocks, financial markets, super investors, and more. Follow the show on Spotify, Apple Podcasts, or YouTube

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