Ruthless Investor Podcast

Ruthless Investor
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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

  1. Oct 24

    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 ruthlessinvestor.substack.com and ruthlessinvestor.com. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ruthlessinvestor.substack.com

    PRGS: The Cash Flow Is Attractive. Debt Is the Risk.

  2. Oct 16

    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 defending the way things have always been done. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ruthlessinvestor.substack.com

    Can a Machine Produce Art?

  3. Oct 12

    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 This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ruthlessinvestor.substack.com

  • 3 Episodes

About

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

Information

  • Creator
    Ruthless Investor
  • Years Active
    2026
  • Episodes
    3
  • Rating
    Clean
  • Copyright
    © Ruthless Investor
  • Show Website
    Ruthless Investor Podcast