Investing Unscripted

Jason Hall and Jeff Santoro
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Sep 21, 2022 • 9min

15. Stock Ideas: Does Upstart Need a Recession to Prove Itself?

Upstart (UPST) has had a very up-and-down existence as a public company. The good news is it could still be a massive winner for patient investors. In this episode, Jason and Jeff discuss the big questions the company still has to answer. 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
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Sep 17, 2022 • 24min

14. How We Invest, Part 2

In episode 2 of this 4-part "How We Invest" series, Jason and Jeff each explain their process for buying stocks and discuss what every investor should consider before making a purchase. 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 
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Sep 14, 2022 • 9min

13. Stock Ideas: What Shopify Has to Do to Become a Big Winner Again

Shopify has been an enormous success, and a great investment for long-term holders. Over the past year, it's been brutal. What's next? Jason and Jeff discuss how the company's hardest work may be ahead of it, and how it has a lot to prove to investors. To watch the video version of this episode, check out our YouTube channel: https://youtu.be/5uLm9Ic396g
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Sep 10, 2022 • 19min

12. How We Invest, Part 1

In episode 1 of this 4-part "How We Invest" series, Jason and Jeff talk about where to find investment ideas to begin the process of deciding what to buy.
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Sep 8, 2022 • 14min

11. Stock Ideas: The Real Estate Trend That’s a Sleeping Giant

America is getting older. In this episode, Jason and Jeff discuss CareTrust, a Real Estate Investment Trust (REIT) that’s poised to benefit from the aging population.
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Sep 5, 2022 • 23min

10. Origin Stories

In this episode, Jason and Jeff tell the stories of what made them the investors they are today.
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Aug 30, 2022 • 28min

9. Mailbag: Should I Buy I Bonds? How Do I Build a Stock Position?

In this episode, Jason and Jeff discuss some listener questions about I Bonds and position sizing in a stock portfolio.
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Aug 28, 2022 • 11min

8. What is Jason's Worst Stock Investment?

Peloton (PTON) has been a terrible investment so far, and one of Jason's worst stocks ever. But there's another one that proved even worse than Peloton. In this episode Jason and Jeff discuss Jason's two worst investments, and share some lessons that can help you avoid making similar mistakes.   
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Aug 26, 2022 • 23min

7. Will There Be Another Market Crash This Year?

Jason and Jeff discuss the possibility of another market crash in 2022, and what investors can do to prepare both their portfolios and their mindset for the next market downturn.
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Aug 23, 2022 • 8min

6: Why is MercadoLibre Jason's Biggest Stock Holding?

More than 20 years after its founding, MercadoLibre is still one of the best growth stocks to own. In this episode, Jeff and Jason discuss its position, how it's already been a big winner for Jason, and why he's continued to buy shares even after earnings more than 12X returns on his initial investment.

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