Investing Unscripted

Bull markets can be just as dangerous for your portfolio as market crashes! Jason and Jeff share how to navigate all-time highs, avoid FOMO, and manage your big winners.

01:06 Markets At New Highs

02:36 Survive A Bull Market

03:48 Recent Crises To Endure

06:30 What Is A Bull Market

08:47 Sidelines And Opportunity Cost

13:44 Fear Vs FOMO

16:37 AI Wave And Market Pockets

20:40 Trade Desk TAM Reality Check

22:12 Datadog Vs SoFi Trimming

25:47 Portfolio Concentration Mindset

27:33 Trimming Winners Wisely

28:32 Position Size vs Age

30:28 Rebalancing Asset Allocation

32:59 Framework Over Emotion

33:26 Lessons From 2022

36:01 Dry Powder Strategy

38:55 Cash Psychology Differences

44:07 Bull Market Mistakes

47:44 Regret Minimization Framework

49:38 When Everyone Asks

Companies mentioned: CRWD, CSCO, DDOG, MSFT, NVDA, SOFI, TTD, ZM

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

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To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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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In this episode, Jason and Jeff sit down with Joe Magyer of Seaplane Ventures to explore how generative AI has completely rewired the startup investing landscape. The trio discusses how tools like Claude and ChatGPT have drastically lowered the cost of building software, the heavy consolidation of capital into frontier labs like Anthropic and OpenAI, and why genuine domain expertise and network effects are more valuable than ever for venture capitalists navigating an AI-native world.

01:36 Why AI Changes VC

03:55 VC Concentration Shift

06:05 Cheaper Startup Building

08:42 More Pitches to Sift

11:24 Using AI for Diligence

14:28 Human Edge and Alpha

20:41 Culture and Expertise Future

27:38 Apprenticeships and Jobs

32:06 AI Jobs History

34:19 Venture Hit Rates

37:52 Defensibility Network Effects

40:07 VC Consolidation Debate

43:14 Founder Leverage Value Add

46:20 Portfolio Support Metrics

49:36 AI Costs Falling Fast

54:47 Next Trillion Giants

57:24 Where To Find Joe

Companies mentioned: AAPL, EBAY, GOOG, GOOGL, META, UBER

Find Joe at https://www.seaplaneventures.com/

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

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices

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

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices

In this recurring segment, Jason and Jeff let an AI randomly select six stocks from their personal portfolios for a rapid-fire review. The hosts deliver a one-sentence thesis, a bear case, and a final "buy or pass" verdict for Arista Networks, Ferrari, Rocket Lab, Alphabet, Mercado Libre, and Starbucks. They debate the risks of AI slowing down for Arista and Alphabet, weigh Ferrari's massive operating margins against its valuation, explore Rocket Lab's upcoming Neutron launch, and discuss whether Starbucks can reclaim its former glory.

01:25 Rules and Stock Randomizer Setup

03:20 Who Goes First AI Coin Flip

04:49 Arista Networks

05:37 Arista Risks Valuation and Space Bet

12:49 Jason Weighs In on Arista

15:00 Ferrari Thesis and Bear Case

22:30 Rocket Lab Thesis and Risks

03:24 Rocket Lab Bull Bear

32:30 Alphabet Thesis Risks

36:38 Alphabet Valuation Debate

38:51 MercadoLibre Credit Risk

45:03 Starbucks Thesis Turnaround

54:49 Wrap Up Listener Call

Companies mentioned: AAPL, ANET, CMG, COST, CSCO, F, GM, GOOG, GOOGL, HOG, KO, MELI, NKE, NU, NVDA, RACE, RKLB, SBUX, SE, UAA, VZ

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

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices

In this July 2026 Mailbag, Jason and Jeff tackle listener questions on when logic should yield to emotion in debt payoff decisions, how to accurately benchmark dollar-cost-averaged portfolios, and which modern stocks fit David Gardner's "Rule Breaker" framework. Plus, they explore AI's real-world robotics data bottleneck and evaluate Southern California industrial REIT Rexford Industrial (REXR).

01:05 Ratings And Mailbag

02:17 Soccer Clip Goes Viral

05:34 Incentives And Ragebait

07:09 AI Disruption Debate

17:46 Rule Breakers Picks

22:53 Whose Picks Are Winning

23:27 Feelings Versus Logic

25:09 Regret Minimization Framework

28:17 HELOC Tradeoffs And Two-Way Doors

31:20 Money Talks With Partners

33:13 Build The Investor Muscle

35:08 Eyes Wide Open Decisions

36:15 Consider A Fiduciary Advisor

38:59 Benchmarking Weekly Deposits

44:34 How To Track Performance

46:30 Rexford Industrial Outlook

Companies mentioned: AAPL, CRWD, DDOG, F, GM, GOOG, GOOGL, MELI, META, NVDA, PLD, QXO, REXR

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

*****************************************

To get 15% off any paid plan at fiscal.ai, visit https://fiscal.ai/unscripted

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

*****************************************

Join our Patreon

Subscribe to our portfolio on Savvy Trader. Use code Unscripted2026 for 30% off a one-year subscription!
Learn more about your ad choices. Visit megaphone.fm/adchoices