Dear SaaStr: As a Founder, When Did You Realize You Were Limiting Your Company’s Growth and Success? As we approached $10m ARR, we were doing very well: growing 100%, cash-flow positive, with 100%+ NRR. But I did see that certain of my weaknesses still were...
The Reality: Most AI Video Tools Are Still Stuck in the Prompt Era. Higgsfield Said “Click-to-Video” Instead. AI video generation technology has been impressive for the better part of a year, but the UX has been challenging for many B2B use cases. E.g.,...
Dear SaaStr: What advice would you give to an entrepreneur who has never pitched before but has a pitch scheduled with venture capitalists? A few basic tips for your first VC pitch: #1. Practice With The Best You Can Find a founder that you know that has raised VC...
Dear SaaStr: What Was the Toughest Rejection You Ever Had in Sales? The hardest rejection I’ve had in sales was around renewals. Especially ones I thought we really had earned. But still lost. In particular, in the early days of EchoSign / Adobe Sign, we had a...
The State of AI + Software: Where It’s Going – Fast This deep dive is from Jason Lemkin at the LIVE AI Workshop Wednesday. Sign up here for the next one. I was talking to a founder recently who’s running at $50 million ARR. Classic SaaS guy turned AI...
Dear SaaStr: My Startup Was Acquired and The Energy is Gone. What Should I Do Next? My first suggestion is: Learn. My second suggestion is: If Not, Then At Least Be Cool. I know you probably sort of hate working in that BigCo corporate environment. I sort of hated it...
One of the most common questions I get from SaaS founders and operators is: “What AI agents are you actually using at SaaStr?” Everyone’s trying to figure out what actually works in this new era. So we put together a quick summary of our AI agent...
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? 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...
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...
