Investing Unscripted

In this back-to-basics episode, Jason and Jeff break down the foundational rules of portfolio construction, asset allocation, and true risk diversification. The hosts explore how to blend an index fund baseline with individual stock picking, examine the mechanics of position sizing and rebalancing, and debate different cash-deployment frameworks. To cap it off, both hosts reveal brand-new stock purchases made during the recording: Jeff's starter position in Brad Jacobs' roll-up vehicle QXO and Jason's opportunistic buy of The TJX Companies.

00:59 Welcome to Investing Unscripted

03:25 Portfolio Basics Setup

04:47 Why Portfolios Matter

08:32 Diversification and Allocation

10:16 Risk Factors Explained

15:29 Beginner Diversification Tips

17:15 Cash and Time Horizon

22:24 Big Picture Diversification

24:27 Mindset and Risk Tolerance

27:55 Simple Starter Portfolio

28:19 Building a Stock Base

29:17 Know Your Investor Style

31:07 Buy Market or Companies

33:22 Index Funds First

35:17 Automating Early Investing

37:57 DCA vs Loose Cadence

39:35 Avoid Cash Timing Traps

41:58 Rollover Deployment System

45:35 Opportunistic Buys and Trims

46:52 New Positions TJX and QXO

49:24 QXO Strategy and Competition

Companies mentioned: ASML, DDOG, ENPH, FSLR, HD, LOW, NVDA, QS, QXO, SBUX, TJX, TSLA, TSM

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 August 2026 Mailbag, Jason and Jeff tackle listener questions on high-conviction stocks gone wrong, unpacking the deceleration and agency friction at The Trade Desk. They explore how co-host overlap can lead to borrowed conviction, discuss what to do when you feel "stuck" in a frothy market, and analyze QuantumScape's shift toward data center power storage and licensing partnerships with Honda and Volkswagen.

04:24 Trade Desk Conviction Lessons

14:01 Valuation Regret And CEO Signals

18:52 Portfolio Overlap And Bias

22:57 Public Disagreements And Recent Buys

23:57 Valuation Debate Winmark

25:03 Rocket Lab Regret

26:02 Building Positions Slowly

27:51 Selling Rocket Lab Puts

30:02 Feeling Stuck Investing

32:56 Do Nothing Discipline

35:31 QuantumScape Honda Red Flag

36:18 QuantumScape Licensing Model

39:55 Verticals Mission Creep

44:50 Position Sizing Fun Bets

Companies mentioned: AMZN, APH, GLW, GOOG, GOOGL, HMC, KNSL, META, MRNA, NFLX, NNI, NU, QS, RKLB, SE, SOUN, TTD, VWAGY, WINA

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

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

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

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 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