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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