In the April 2026 First Friday livestream, Jason and Jeff break down the current "market vibes," debating whether the market's resilience is masking a hair-trigger sensitivity to AI hype and PR spin. They announce the Q1 winner of the listener portfolio contest—congratulations to Discord member Vinny G!—and review the progress of their own 2026 picks. The duo dives deep into the executive turnover at The Trade Desk, the slow-moving turnaround at PayPal, and whether Kinsale Capital is simply a cyclical price taker or a highly efficient operator. Plus, Jason reveals his new Roth 401 (k) strategy, and Jeff vehemently defends his "lazy" personal finance choices.

03:01 Market Vibes Resilience

06:26 AI Hype And Volatility

09:54 Cybersecurity Rumor Debate

12:19 Cringey AI Promo Clip

14:35 Portfolio Contest Rules

16:31 Q1 Winner And Charity

21:09 Patreon Standings And Long Game

24:22 Portfolio Reflections And Trade Desk

28:00 Board Sale Speculation

30:49 Backing Jeff Green

32:19 Position Sizing Rules

32:45 Founder vs Operator Debate

37:11 Kinsale Competition Pressure

38:40 Kinsale Underwriting Edge

42:23 Specialty Insurance Tailwinds

45:30 PayPal Value Trap Risk

52:15 Roth 401k Moves

55:20 Roth Optionality Strategy

57:46 Favorite Dividend Picks

Companies mentioned: BIP, BIPC, BORR, CTRE, EPR, GOOG, GOOGL, KNSL, MA, MELI, NOW, PLSDF, PLTR, PYPL, RBRK, RKLB, SECYF, TTD

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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