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Scaling to $3B: How Clio Built a Vertical SaaS Powerhouse with AI and Innovation with CEO Jack Newton
Oct 24, 2025
The 17-Year Journey: From Cloud Pioneer to AI-Powered Platform When Jack Newton and his elementary school best friend Ryan Wong founded Clio in 2008, they were building the very first cloud-based practice management system for lawyers. It was a radically different...
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder … Who Was Once a Friend?
Oct 24, 2025
Dear SaaStr: What's The Best Way to Fire Your Co-Founder Who Was Once a Friend? It's pretty common that a co-founder doesn't work out, unfortunately. I've been a part of all versions of this: I've had a great co-founder that went the distance with me. I've had one...
20VC x SaaStr This Week: The Great VC Shuffle, TAM Exhaustion in AI, and Why a Billion in ARR Is “Still Early”
Oct 23, 2025
We're back!! Jason Lemkin, Harry Stebbings, and Rory O'Driscoll diving into the startup and venture capital conversations that actually matter—from Benchmark's masterclass in talent acquisition to why billion-dollar ARR companies are "still early" in today's elongated...
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Scaling to $3B: How Clio Built a Vertical SaaS Powerhouse with AI and Innovation with CEO Jack Newton
By Jason Lemkin | October 24, 2025
The 17-Year Journey: From Cloud Pioneer to AI-Powered Platform When Jack Newton and his elementary school best friend Ryan Wong founded Clio in 2008, they were building the very first cloud-based practice management system for lawyers. It was a radically different time: cloud computing was still novel, SaaS was an emerging model, and convincing lawyers…
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Blog Posts, Q&A
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder … Who Was Once a Friend?
By Jason Lemkin | October 24, 2025
Dear SaaStr: What’s The Best Way to Fire Your Co-Founder Who Was Once a Friend? It’s pretty common that a co-founder doesn’t work out, unfortunately. I’ve been a part of all versions of this: I’ve had a great co-founder that went the distance with me. I’ve had one that quit less than a year into…
Continue Reading
Blog Posts
20VC x SaaStr This Week: The Great VC Shuffle, TAM Exhaustion in AI, and Why a Billion in ARR Is “Still Early”
By Jason Lemkin | October 23, 2025
We’re back!! Jason Lemkin, Harry Stebbings, and Rory O’Driscoll diving into the startup and venture capital conversations that actually matter—from Benchmark’s masterclass in talent acquisition to why billion-dollar ARR companies are “still early” in today’s elongated exit environment. This week’s discussion gets refreshingly honest about stage specialization, the anxiety economy of modern VC, and whether…
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