Ruthless Investor Podcast
by Ruthless Investor
Ruthless Investor is about investing, money, decision-making, and the ideas that shape how we think about all three. No theatrics, no borrowed convictions—just digging into the numbers, questioning the assumptions, and making up your own mind. ruthlessinvestor.substack.com
Episodes
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PRGS: The Cash Flow Is Attractive. Debt Is the Risk.
Progress Software (PRGS) generates substantial cash flow, but its acquisition of Domo has added significant debt and integration risk. In this episode, I explain why I bought shares, what needs to go right, what could go wrong, and why I'm keeping my position small. You can also find me at...
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Can a Machine Produce Art?
Photography didn’t destroy painting. It helped change what painting could become. Could AI do something similar? In this episode, I explore whether we’re too focused on what AI might replace and not enough on what it might make possible. And whether we’re protecting what’s valuable or simply...
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Dollar General (DG) Stock Analysis: The Turnaround Is Working. I’m Selling Anyway.
In Episode 1 of Ruthless Investor, I break down Dollar General (DG), the risks that still matter, and the valuation that pushed me to sell. At today’s price, am I being paid enough for the things I might be wrong about? Full analysis: RuthlessInvestor.com Subscribe: ruthlessinvestor.substack.com...
About this show
Ruthless Investor is about investing, money, decision-making, and the ideas that shape how we think about all three. No theatrics, no borrowed convictions—just digging into the numbers, questioning the assumptions, and making up your own mind.
ruthlessinvestor.substack.com
Hosted by
Ruthless Investor