Harry Stebbings. Rory ODriscoll and I have done 37 podcasts together this year (!). We didn’t miss a week. But man, the world changed in those 37 weeks. My top learnings… and what’s changed: #1. I Won’t Do a T3D2 Investment Again I know this...
Most of what you hear about sales hiring is recycled advice: look for humility, avoid blamers, hire for grit. Fine. True. Not interesting. But buried in a recent conversation with Harry Stebbings and Maggie Hott — OpenAI’s GTM leader who built ChatGPT Enterprise...
Dear SaaStr: I am running out of runway and in our fundraise we so far have had no luck with termsheets. when is the right time to call it a day? It’s tough, but here’s the reality: you call it a day when you’ve exhausted every reasonable path to survival and growth,...
Can you really grow in B2B in 2026 if you aren’t tapping into AI budget? The short answer: Probably not. Here’s the real data. It may in fact be your last, best change to tap into it. Something fundamentally different happened in 2025. AI budgets stopped being...
From -19% Decline (1st half year) to +47% Growth (2nd half year): What Actually Happened That’s a 66% swing in growth in SaaStr readers over the course of 2025. Over less than 12 months. At the start of the year, SaaStr website traffic while still substantial...
Dear SaaStr: What Was the Moment You Knew You Had to Break Up With Your Co-founder? It’s happened to me twice, that “moment”. It was the same thing both times: When they just didn’t show up to a critical meeting. Founder conflict is unfortunately pretty common. I was...
We talk a lot about what’s driving the fastest-growing AI startups. Is it the technology? The timing? The TAM expansion? All of that matters. But it’s also something that’s easy to overlook because it’s almost too obvious: The best AI B2B startups...
There’s a lot of advice out there about how to get rich. Start a company. Invest in crypto. Build a personal brand. Have multiple revenue streams. But if you want to understand how generational wealth is actually created for tens of thousands of people at once,...
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
The classic sales plays do still work. Hard work, knowing the product cold, showing up. But the classic 2021 playbook? It’s close to dead in the Age of AI. And here’s one example of why. The other day I did something that should make every sales rep reach for the...
