Investing Unscripted

Hosted by Jason Hall and Jeff Santoro

Business Investing

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Episodes

276

Latest episode

Aug 2026

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About the show

Welcome to Investing Unscripted, where we ask the hard questions about investing, the stock market, and personal finance. We don't have THE answers, we only have OUR answers.

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60 recent

August 19, 202658 min

219. How to Survive a Bull Market

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

August 12, 20261 hr 2 min

218. How AI is Changing Everything About Startup Investing with Joe Magyer

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

August 9, 20261 hr 1 min

First Fridays 33. August 2026

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

August 5, 202659 min

217. I Still, Still Gotta Think About That One

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

July 29, 202655 min

216. July 2026 Mailbag

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

July 22, 202655 min

215. Jason Explains Banks

Why do banks count your deposits as liabilities? We're breaking down how banks actually buy and sell money, plus how to evaluate loan books and bank earnings.  00:49 Why Talk Bank Stocks 03:41 Banks Buy And Sell Money 07:24 Bank KPIs That Matter 09:36 Why Banks Look Revenue-Less 13:26 Deposits As Liabilities 18:53 Interest Rates And Margins 22:41 Fixed Rate Loan Squeeze 24:11 Deposit Rates Lag Reality 25:04 Net Interest Margin Basics 25:55 Types of Banks Explained 29:15 Universal Banks And Mergers 30:40 Specialty Models Live Oak Schwab 33:19 Loan Book Risk And Bank Runs 35:31 Collateral Versus Unsecured Debt 39:20 Screening Tools And Valuation Cycles 43:00 Common Investor Mistakes Fintech Hype 46:28 Where We Are In The Cycle 48:45 Bank Picks And Closing Thoughts Companies mentioned: AX, BAC, C, COF, GS, JPM, LOB, MS, PNC, SCHW, SOFI, TFC, WFC 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

July 15, 20261 hr 9 min

214. Is it Time to Buy the Mag 7?

Are the mega-caps officially a buy? We're breaking down the valuations, moats, and hidden risks for every Magnificent Seven stock. 00:42 Why Mag Seven Now 05:04 Market Benchmark Setup 05:38 Alphabet AI Optionality 13:40 Apple AI Strategy 21:10 Amazon AI Adjacent Case 35:18 Nvidia Expectations Shift 40:22 Index Fund vs Stock Pick 44:28 Meta Bear Case 51:34 Tesla Hype vs Reality 55:44 Microsoft Copilot Monetization 01:00:23 Portfolio Contest Callback 01:02:32 Buy or Short Mag 7 Companies mentioned: AMD, AMZN, AVGO, GOOG, GOOGL, INTC, MSFT, NVDA, TSLA 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

July 11, 20261 hr 4 min

First Fridays 32. July 2026

In this midyear live stream, Jason and Jeff look back at a chaotic first half of 2026, dissecting how the broader market continues to push ahead despite global geopolitical tensions. The hosts dive into a data-backed re-evaluation of their personal portfolios, checking in on massive year-to-date winners like Datadog and Texas Instruments, while reflecting on painful laggards like The Trade Desk. They outline exactly how to value speculative, pre-revenue plays like QuantumScape following its fresh Honda partnership, crown a new winner in the monthly portfolio contest, and deliver a harsh warning on consumer-packaged goods like Celsius as they face private-label replication from big-box competitors. 01:21 Welcome and Community Chat 03:27 Today’s Agenda Midyear Check 06:25 Market Vibes and Sector Moves 17:41 Top Portfolio Winners YTD 23:49 Adding to Winners Debate 30:21 Worst Performers  39:04 QuantumScape Buy Debate 47:03 Portfolio Contest Winner 52:58 Celsius Stock Breakdown Companies mentioned: ASML, CELH, COST, CRWD, DDOG, FTNT, HMC, ISRG, LLY, META, MRNA, NOW, NVO, PEP, QS, TTD, TXN 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

July 8, 20261 hr 4 min

213. What the Hell is Going On? With Nick Rossolillo

What the hell is going on with tech valuations?  Nick Rossolillo joins us to break down the trillion-dollar AI infrastructure cycle and why "commodity" hardware is running wild. 02:04 Chip Stock Investor Process 05:00 AI Trade Big Picture 06:18 Hyperscaler CapEx Wave 10:24 Who Pays For AI 11:16 AI Beyond Consumers 16:58 Valuations And Risk 22:40 Memory Stocks Spotlight 26:13 Is Memory A Commodity 28:21 Upgrade Cycles And Stickiness 32:00 Making Memory Less Commodity 35:04 OPEC Analogy Supply Control 36:43 Flash Memory Challengers 38:52 Apple Micron China DRAM 39:56 Portfolio and Research Ads 41:44 Power Generation Constraints 44:03 AI Labs and IPO Rumors 45:57 LLM Risks and Regulation 52:24 SpaceX Valuation Debate 57:52 Where to Find Nick Companies mentioned: AMD, AMZN, ASML, MU, ORCL, QS, RKLB, TSLA Check out https://chipstockinvestor.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

July 1, 202659 min

212. Stocks We Haven’t Bought…Yet

We're opening up our watchlists! From luxury supercars to social media platforms, we break down why we haven't bought Ferrari, Reddit, or Rocket Lab…yet. 03:48 Watchlist Episode Setup 06:14 Ferrari Luxury Thesis 11:27 Lululemon Value Debate 19:15 Options Lessons Puts Calls 23:44 BBB Foods Watchlist Pick 29:29 Rocket Lab Valuation Debate 34:16 Options Strategy For Volatility 35:32 TransMedics Mission And Doubts 42:01 Reddit Business Model Fears 47:48 AI Data And Growth Metrics 51:22 Pick One Stock Today Companies mentioned: ISRG, LULU, MTH, RACE, RDDT, RKLB, TBBB, TMDX, TOST 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 (https://open.spotify.com/show/4SBtOWGEOmD9pmltgIXO8r?si=6213b1574ff04bce) Apple Podcasts (https://podcasts.apple.com/us/podcast/chit-chat-stocks/id1437766060 YouTube https://www.youtube.com/@ChitChatStocks ***************************************** Join our Patreon: https://www.patreon.com/investingpod Subscribe to our portfolio on Savvy Trader (https://savvytrader.com/investingunscripted). Use code Unscripted2026 for 30% off a one-year subscription! 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