A deep dive into the biggest AI rounds, the future of venture capital, and why California’s wealth tax could trigger a founder exodus We just wrapped another 20VC + SaaStr pod with Harry Stebbings and Rory O’Driscoll from Scale Venture Partners, and this...
A Cautionary Tale from 2025/2026 Here’s something I never thought I’d have to write about, but after watching it happen three times in a single year (really more than that), it’s time we talked about it openly. I’ve now seen three separate VC...
Ryan Anderson, CEO of Filevine, shared their AI transformation playbook at SaaStr AI London. Here’s the thing: their new AI revenue now exceeds their SaaS revenue on a quarter-over-quarter basis. This is the roadmap. The Filevine Story: 10 Years of Grinding,...
Dear SaaStr: Is It Worth Working as a Sales Rep? Absolutely. Being a sales rep is the hardest job that almost anyone can get and at least try to do. But boy, you will learn. You will learn: How to hear “No” 100 times in a row. If you can turn 100 “No’s” into 1–2...
“For Freemium and PLG to work at scale, you probably need millions of folks to use your product. If it’s 1000’s … then go sell it.” Freemium is back. In fact, it’s never been bigger. The Age of AI is build on freemium. ChatGPT is the...
ElevenLabs will probably be worth more than Twilio by mid-2026 Really seems like a missed opportunity there — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) January 13, 2026 ElevenLabs is on track to match Twilio’s current market cap in under 5 years from founding,...
Dear SaaStr: What’s The Lamest Thing You See Sales Reps Do To Close a Deal? The “lamest” is Fake FUD. But the thing is, it works. Up to a point. What is Fake FUD? FUD is Fear, Uncertainty and Doubt … that isn’t true: “They just lost Google as an...
I felt something interesting for the first time last week. Something I haven’t felt yet in my AI Agent journey. I felt like an AI tool was… expensive. Not because it actually was expensive. But because my expectations have fundamentally shifted. Let me...
Dear SaaStr: How Much Money Does a VC Make If Their Investment Sells for One Billion? Often not as much as you’d think. Each general partner might make $5m here on a $1B exit. And a non-true general partner might make quite a bit less. Let’s say: The fund owns 10% at...
Most folks deploying AI SDRs and similar tools are doing it all wrong. They think the tool can magically on its own figure out how to sell for you. It can’t. At least not today. None of them can. Here’s what nobody tells you when you’re shopping...
