Stripe just released its 2026 annual letter, and as always, it’s packed with data. But a lot of the letter covers stablecoins, agentic commerce protocols, and macro-economic commentary. All interesting — but let me pull out the 5 metrics that matter most if...
Dear SaaStr: How Do You Know When It’s Time to Leave Your Current Company and Move On? There are a lot of valid reasons to leave your job for a potentially better one. But — if your job isn’t bad, and your boss is pretty good, it’s worth...
I was in a board meeting last week for a breakout AI B2B leader at $100m+ ARR and the team was excited … but stressed. Why? So many of their largest customers were happy to sign relatively large checks for their AI Agent. Six figures. Some even seven. The product was...
Everyone said 2025 was the year the IPO window reopened. And technically, it did. 174 companies raised over $31 billion in the first half alone — the highest since 2021. But here’s what nobody wants to talk about: most of the B2B and tech IPOs from 2025 are now...
Dear SaaStr: What’s It Really Like to Be CEO of a Startup? Let me just throw out a few things I’ve learned that being a CEO of start-up isn’t, or isn’t as you’d expect: It isn’t glamorous until you are At Scale and Hot, at the very minimum. At...
I get it. A lot of jobs in tech just aren’t that rewarding anymore. If they ever were. At least in 2021, they were kind of easy, and you got to work from home, often < 30 hours a week. These six figure jobs honestly aren’t all that great, in many...
Anthropic just published a breakdown this week of where AI agents are actually deployed across nearly 1 million real production tool calls. Software engineering sits at 49.7%. Sales and CRM is at 4.3%. Finance at 4.0%. Legal at 0.9%. At first it might seem to say AI...
Dear SaaStr: What Are The Top 5 Things I Should Know Before Starting a SaaS Startup? My Top 5: It will take you at least 24 months to really get anywhere. Everyone mentally budgets 10–12 months. It’s never enough. At least, not to get enough paying customers from Code...
Dear SaaStr: What is The Biggest Pain for a CEO? Competition is stressful. Raising funding can be hard. Partnerships can be frustrating. But the hardest part is always recruiting. And it never gets easier, not really. Every CEO I see past $2m in ARR or so, be it...
There’s been a massive SaaS sell-off since mid-2025. Multiples compressed. Growth stocks punished. The “SaaS is dead” takes are everywhere again. B2B isn’t dead. Software is still eating the world. Businesses still need tools. Enterprise...
