Jason Hall and Jeff Santoro

Investing Unscripted

Business EN ↓ 269 episodes

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.

Author

Jason Hall and Jeff Santoro

Category

Business

Podcast website

investingunscripted.com

Latest episode

Jul 8, 2026

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Episodes

44. What's Jacob Goldstein's Problem? 18.03.2023

Jacob Goldstein knows a lot about money. He wrote Jason's favorite book (apologies to Morgan Housel) about it, called "Money, the True Story of a Made-Up Thing". Jacob also hosts "What's Your Problem," the podcast where he talks to really smart people about problems they're trying to solve.  This week, Jeff and Jason sat down with Jacob to talk about the failures of Silicon Valley Bank and Signatu...

43. March Mailbag 11.03.2023

Time for another mailbag! We answer a handful of great questions from listeners, including concerns about a dividend trap, set-it-and-forget-it investments in renewable energy, our favorite boring stocks, selling stocks on fundamentals, and more. Have questions you want us to answer on a future mailbag? Contact us via the ways below. In the second part of the show, Jeff and Jason also share the re...

42. Investing is Funny: Comedian Mitch Fatel 04.03.2023

What does our own Jeff Santoro have in common with comedian Mitch Fatel? Despite Jeff's insistence, it's not being funny. Like Jeff (and many of you), Mitch began his investing journey during the Coronavirus pandemic, and now counts picking stocks and learning about the companies he owns as one of his favorite pursuits. Jason and Jeff recently had a wide-ranging conversation with Mitch about his i...

41. Semiconductors with Nick Rossolillo 25.02.2023

Semiconductors are an interesting part of the investing universe so we dedicated an entire episode to them. Listen to an interview Jason did with Nick Rossolillo, one of our favorite investors who knows a lot about the semi space. Then, Jason explains the semiconductor industry to Jeff like he’s 5 years old. Companies discussed: AAPL, AMD, ASML, INTC, NVDA, SSNLF, TSM, TXN Connect with Nick on Twi...

40. Stocks We Hate That We Love 18.02.2023

Everyone loves a great story. The problem is that great stories don't always make for great investments. Jeff and Jason share their stories of seven stocks they love, but that they hate that they love.  It's a story as old as time: The portfolio gets what the heart wants. In the second part of the show, Jeff and Jason play Change my mind, the game where they each bring a stock, and the other perso...

39. Maxfield on Banks and January Portfolio Update 11.02.2023

John Maxfield may be the most under-the-radar expert on banks in America, an industry Jason thinks investors are missing out on if they don't understand. In this episode, Jeff and Jason have a wide-ranging conversation with John about banks as businesses, investments, and what you need to know to get started making the most of your new-found bank knowledge – including where you can find that knowl...

38. How Many Stocks Should You Own? 04.02.2023

How many stocks should you own? Like many of the hard investing questions, there are a lot of right answers. And the number that's right for one person may be completely wrong for someone else. There's also a good chance the number that's right for you today could change over time. In this episode, Jeff and Jason talk through this challenging topic, share their own experiences and offer some ideas...

37. January Mailbag 28.01.2023

Mailbag! This week, Jeff and Jason answer questions about valuing companies who've gone through major changes in their business, a group of renewable energy stocks, the chances some really beaten-down stocks can recover, stock-based compensation, and some interesting data about stock returns. After the ad break, we play "tell me I'm wrong," and now Jason is going to blow up his portfolio. Stay tun...

36. What Are You Retiring To? 21.01.2023

Many people look forward to retiring, often with dreams – or even plans – of days filled with leisure. But the reality is, after years of working or running a business, people need something to fill their time, replace the lost companionship, and provide a sense of fulfillment. And for people planning to retire early, often you need to bridge the lost income and benefits not available until full r...

35. 5 Stocks for 10 Years 14.01.2023

Five stocks. 10 Years. That's all you can own. Jeff and Jason go through this thought exercise and learn that there's a lot more to it than just the stocks they came up with. In this episode, they discuss the things they focused on, the characteristics they prioritized in the companies they chose, and most importantly, what they learned about themselves as investors as a result. Can this framework...

34. Investing Resolutions You Can Stick To 07.01.2023

People do two things every year: Make resolutions, and then promptly fail to achieve them. When it comes to financial resolutions, it's usually because they are too vague and not actionable, and people don't really plan for success. In this episode, Jason is joined by financial planner and investor Matthew Frankel, CFP®, to discuss why people fail at resolutions, and what they can do to move from...

33. Thank God That's Over: 2022 Review 31.12.2022

It’s been a year, people. In the last episode of the year, Jason and Jeff talk about the biggest stories of 2022 and what they mean for investors in 2023. Companies mentioned: AMZN, BIP, LCID, NEE, OXY, SBUX, TGT, TSLA, WMT We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/@TheSmat...

32. Smattering Portfolio 2023 Reveal 24.12.2022

Time to draft our stocks for the 2023 Smattering Portfolio! In this episode, Jeff and Jason discuss the stocks viewers picked for the listener portfolio, draft their own stocks for the competition, and pick three more stocks together that will go towards the viewer-nominated charity. If you're looking for more insight into some of the stocks Jason and Jeff like, this episode will be right up your...

31. Reckless Predictions for 2023 17.12.2022

Let's get Reckless! Jeff and Jason are joined by three guests to talk about the coming year, and make a wide range of predictions about stocks and the markets broadly. Wondering what Zoom will do with all its cash next year? Whether Bitcoin will outperform bonds? What will Salesforce's Marc Benioff try to buy? We try to answer some of those – and a lot more – with the help of Tyler Crowe, Travis H...

30. December Mailbag and Introducing the 2023 Smattering Portfolio Contest! 10.12.2022

December mailbag! In this episode, Jason and Jeff answer listener questions about companies the market has right and wrong, how Jeff decides what to buy each week, valuation metrics, and more. Then, Jason and Jeff reveal the Smattering 2023 Portfolio, a fun stock-picking competition that will benefit multiple charities and include stock picks from listeners! Companies mentioned: ABNB, ASAN, BOC, L...

29. Tyler Crowe: Investing For Humans 03.12.2022

Between financial media built to attract and retain audiences often using sensationalist headlines and hype, and a financial services industry built for the uber-wealthy, it can feel inaccessible for individuals. In this episode, Jeff and Jason have a conversation with engineer-turned investor and analyst, Tyler Crowe, about cutting through the noise and focusing on your goals to build wealth. As...

28. What Emotions Make You a Better - or Worse - Investor? 26.11.2022

Investing is driven by emotions and understanding your own emotions is a the heart of your own success. In this episode, Jason and Jeff dive into this important topic and talk through their own emotions, how they impact their decisions, and what they do to combat -- and leverage their emotions to be better investors.  We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter:...

27. Is it Time to Sell Stocks? 19.11.2022

Deciding when to sell a stock is an important decision. Building on episode 4 of the "How We Invest" series, Jason and Jeff discuss reasons to sell, including some recent stock sales of they made. We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/@TheSmatteringShow Learn more about...

26. Mistakes Were Made 12.11.2022

Even the best investors make mistakes. In this episode, Jason and Jeff discuss their biggest investing and personal finance mistakes and what they learned from them. We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/@TheSmatteringShow Learn more about your ad choices. Visit megapho...

25. Jim Gillies: Tales From a Cash-Flow Investor, Part 2 05.11.2022

In part 2 of our conversation with Jim Gillies, Jason and Jeff discuss options trades and strategies, and how Jim thinks options can be best used for most investors. Jim also shares his best and worst stock picks, why he’s actually a Southerner at heart despite being born and raised Canadian and shares his 30 favorite bands.  We would love feedback on the show: Email: thesmatteringshow@gmail.com T...

24. Jim Gillies: Tales From a Cash-Flow Investor, Part 1 05.11.2022

In part 1 of this conversation with Jim Gillies, an engineer-turned-investor who has spent the past 17 years picking stocks and options trades for The Motley Fool, Jeff and Jason discuss his professional training, how he thinks about investing, and the framework that’s made him one of the best. If you want to be a better investor across any market environment, give this episode a listen.  We would...

23: What's the Hardest Part of Investing? 29.10.2022

We asked, and you answered. In this episode, Jason and Jeff discuss what listeners told them is the hardest part of investing. The short answer? Everything.  We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/channel/UCbM5n0xiN64xJlUqJcQB2Eg Learn more about your ad choices. Visit m...

22: What is Risk? 19.10.2022

In this episode, Jason and Jeff discuss what risk is, what it isn’t, and how to think about it in your investing and personal finance. We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/channel/UCbM5n0xiN64xJlUqJcQB2Eg Learn more about your ad choices. Visit megaphone.fm/adchoices

21. Mailbag: Three Listener Questions 12.10.2022

In the October mailbag, Jason and Jeff answer listener questions about when to be a contrarian, if it's ever too late to start investing, and how stock buybacks work. We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/channel/UCbM5n0xiN64xJlUqJcQB2Eg Learn more about your ad choices...

20. How to Get Through a Down Market 08.10.2022

Let's face it, the market's been bad. In this episode, Jason and Jeff discuss their mindset in down markets and how they use their investing frameworks to weather the storm. We would love feedback on the show: Email: thesmatteringshow@gmail.com Twitter: @smatteringshow Check out our YouTube channel for more content: https://www.youtube.com/channel/UCbM5n0xiN64xJlUqJcQB2Eg Learn more about your ad...

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