The Ledger

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Insight
Grady: Early SaaS was a business model shift, not a UX revolution
“If you look at the last decade or so of software, the transition has been from on-premise to SaaS or on-premise to cloud, and that's been a wonderfully impactful transition, but at a very fundamental level, it's been a transition in the business model, not a t…”
Pat Grady Mar 13, 2017 ▶ 8:23 20VC: Sequoia Partner, Pat Grady on Why Data Is The New Oil, Why We Will See The Return of The Apprenticeship Model in VC & The Defining Characteristics of The Next Generation of Great Software
Insight
Soltero: Open-source software cannot be sold via traditional top-down enterprise models
“They were doing a sort of typical top-down sales approach and the type of go to market dynamics usually reserved for the Siebels and you know, oracles of the world, and you couldn't do that then, you can't do it now.”
Javier Soltero Sep 6, 2015 ▶ 5:01 FF 012: Acquired by Microsoft for $200m with Javier Soltero @ Microsoft
Insight
O'Driscoll: AI Software Automates Actual Work Rather Than Just Updating UIs
“Salesforce was rebuild Siebel in the cloud, and it was fun, and we made a lot of money, but you're right, somewhat boring. What is really exciting now is you're not just talking about rebuild Salesforce exactly the same, but with a slightly modern UI. You are …”
Rory O'Driscoll Nov 13, 2025 ▶ 1:12:01 Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
Opinion
Kurtz: Legacy security resembled Siebel instead of cloud-native Salesforce
“Everything to me looked like Siebel, and I thought it should look like Salesforce.”
George Kurtz Oct 14, 2021 ▶ 3:35 20VC: Crowdstrike Founder, George Kurtz on Scaling to a $60Bn Market Cap, How to Acquire and Retain the World's Best Talent & The Right Way to View Competition in Today's Market?
Opinion
Grady: Salesforce was garbage compared to on-premise Siebel in 2007
“Salesforce.com circa 2007 was garbage compared to on-prem Siebel system.”
Pat Grady Jul 8, 2024 ▶ 1:07:48 Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174 · 20VC with Harry Stebbings
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