Catching a Falling Knife: The Truth About Software Stocks Today | The Real Eisman Playbook Ep 54

Catching a Falling Knife: The Truth About Software Stocks Today | The Real Eisman Playbook Ep 54

From The Real Eisman Playbook by Steve Eisman

April 13, 2026 · 59 min

About this episode

Steve Eisman interviews software analyst Rob Oliver to discuss the challenges and future of the software sector amidst significant valuation declines.

On episode 54 of The Real Eisman Playbook, Steve Eisman sits down with Rob Oliver, software analyst at Baird, to break down why the software sector has been obliterated over the past year. Rob shares which companies he believes have the moat and innovation culture to make it through to the other side, and why despite valuations being cut in half, most software investors still aren't ready to buy. 00:00 - Intro 01:16 - History of the Software Sector & Where We're At Now 16:19 - What Makes a Successful Software Company Today? 18:10 - Looking Ahead Two Years 26:43 - How Far Has Valuation Fallen? 29:34 - Stock Based Compensation 33:14 - Vertical Software Companies 37:15 - Private Equity & Private Credit 43:05 - Feedback From the Buy Side 46:00 - AI Native Strategies 50:13 - Nobody Loves Software Right Now 54:21 - Outro Subscribe 👉🏻https://www.youtube.com/@RealEismanPlaybook?sub_confirmation=1 Connect with Steve Eisman and access all things The Eisman Playbook: 🌐 https://linktr.ee/realeismanplaybook → Follow on socials, watch episodes, and get the latest updates — all in one place. Disclaimer: The financial opinions expressed are for information purposes only. The opinions…

People in this episode

Host: Steve Eisman

Guest: Rob Oliver

Topics covered

  • software sector analysis
  • investment strategies
  • valuation trends
  • company innovation
  • market outlook

Keywords

  • software stocks
  • investment
  • valuation
  • private equity
  • AI strategies

Mentioned in this episode

Organizations: Baird

Books & works: The Real Eisman Playbook

More episodes of The Real Eisman Playbook

Explore listener stats, chart rankings, contacts and more on the The Real Eisman Playbook podcast page.