The Real Eisman Playbook

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


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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


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Disclaimer: The financial opinions expressed are for information purposes only. The opinions expressed by the hosts and participants are not an attempt to influence specific trading behavior, investments, or strategies. Past performance does not necessarily predict future outcomes. No specific results or profits are assured when relying on this content.


Before making any investment or trade, evaluate its suitability for your circumstances and consider consulting your own financial or investment advisor. The financial products discussed in ‘The Eisman Playbook' carry a high level of risk and may not be appropriate for many investors. If you have uncertainties, it's advisable to seek professional advice. Remember that trading involves a risk to your capital, so only invest money you can afford to lose. Derivatives are unsuitable for all investors and involve the risk of losing more than the amount originally deposited and any profit you might have made. This communication is not a recommendation or offer to buy, sell, or retain any specific investment or service.

Copyright ©2025 Steve Eisman

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