“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...
Dear SaaStr: What Happens if a VC Loses All Their Money on an Investment? It’s OK — if it’s not too much. As long as the founders did everything they possibly could to make it work. Everything. And were honest. There are two types of losses for VCs...
There’s a temptation in AI to always reach for the biggest, most powerful model. The latest release. The premium tier. The one with the best benchmarks. Especially given the incredible pace of competition and innovation in AI + B2B today. And sometimes...
Dear SaaStr: We lost an enormous RFP because we are too small. Any advice? This is indeed a big bummer. But it truly does make you stronger — if you commit to winning the next one. Six thoughts on how to do better next time: First, move them into your Lost Now...
I know this is advice you probably don’t want to hear. We’ve all been told that micromanagement is bad. That great leaders hire great people and get out of their way. That autonomy is the secret to building high-performing teams. And that’s 100% true. For...
