Anthropic Just Passed OpenAI in Revenue. While Spending 4x Less to Train Their Models
Both OpenAI and Anthropic dropped major revenue disclosures within days of each other this week. OpenAI confirmed $2 billion in monthly revenue alongside a $122 billion raise at an $852 billion valuation. Anthropic confirmed $30 billion in annualized run-rate, up from...
How Databricks Sells to Dozens of Industries Without Building a Single Vertical Product
The “Industry Imperatives” Framework That Replaced Personas and ICP as Their Core GTM Strategy From a SaaStr AI Annual session with Madelyn Mullen (Sr. Industry Solutions Manager – Digital Natives, Databricks) and Samantha Sawyer (Principal Industry...
10 Things I’d Do Differently as a Founder Next Time
Dear SaaStr: What would you do differently to succeed, if you were to start again? My top list: Don’t start a startup if the founders aren’t 100% aligned, especially on how committed you all are. I’ve done this, and it worked out OK, but not even close to as well as...
It’s Sunday on Slack. No One Told Our AI Agents They Didn’t Have to Check In.
I woke up Sunday morning morning, grabbed my coffee, and opened Slack. No one’s working. Except … well that’s not quite right anymore. Two highly detailed reports were already waiting for me. Posted at midnight and 9:00 AM, respectively. Our...
OpenAI’s $122B “VC Round” Is Vendor Deals, Contingent Capital, and a Guaranteed Return It Arguably Can’t Afford
The three anchors are a cloud vendor, a chip vendor, and a holding company with a circular revenue deal. The actual VC-style capital is a fraction of the headline. OpenAI closed $122 billion at an $852 billion post-money valuation on March 31, 2026. But it’s not...
Dear SaaStr: As a Startup Founder What Was The Worst VC Meeting You Ever Had?
I pitched 150+ entities over the years as both a start-up exec and a founder. And now I’ve been on the other side of far more than 150 meetings as part of SaaStr Fund. Nothing in fundraising really phased me as a founder — for the most part. Except one set of...
Come to SaaStr AI Annual in May, and We’ll Teach You How to Build an AI VP of Marketing. For Real.
We get asked some version of this question 10x a week now: “Jason / Amelia, how do I actually build an AI agent that does real work? Not a chatbot. Not a demo. Something that actually runs part of my company.” There are 10,000 AI agent demos on YouTube....
We Can Never Go Back to Working Without AI Agents
Amelia, our Chief AI Officer, and I had a conversation the other day that felt like stating the obvious. But maybe it’s worth saying out loud. We literally could not go back to running SaaStr without our AI agents. Not “wouldn’t want to.” Could...
Dear SaaStr:Â What Was The Best Advice You Ever Got From an Angel Investor
Dear SaaStr:Â What Was The Best Advice You Ever Got From an Angel Investor The best advice I ever got from one of my angel investors:Â Stop feeling sorry for yourself. I went to meet with one of my angels and mentors when things were probably toughest at my last...
What CIOs Are Most Looking to Replace with AI Today
The question every B2B exec should be asking right now is not whether CIOs are looking to replace software with AI. They are. The question is which software, and how fast. Redpoint surveyed 141 CIOs in March 2026 and asked a direct question: in which software...
Why Every Tech Company at Scale Should Be Looking at Deals Like OpenAI + TBPN
OpenAI just acquired TBPN, the daily live tech talk show hosted by Jordi Hays and John Coogan. You probably saw the news, and we’re TBPN super fans at SaaStr since Day 1. We’ve done a lot of media, events, and more over the years and to us at least it...
Dear SaaStr: Did it Ever Take You a Year Or More to Close a Sale?
Dear SaaStr: Did it Ever Take You a Year Or More to Close a Sale? Absolutely. It took us about 18 months to close Google, for example: Need identification and discussions with project manager over several months About 6 on-site meetings to review need identification...
How We Built Our AI VP of Customer Success, “Qbee” — And How You Can Build Yours
We’ve now built 20+ AI agents and 12+ vibe coded apps used 800,000+ times at SaaStr. We’ve shared how we rolled out our AI SDRs, and how we built / vibe’d our AI VP of Marketing as well as a bunch of AI-powered VC tools that have done almost a million...
We’ve Crossed 4,000 (!) VC Pitch Decks Graded With SaaStr AI’s Pitch Deck Analyzer. Here’s What It’s Taught Us About Fundraising in 2026
Last year we launched the SaaStr AI VC Pitch Deck Analyzer at saastr.ai/pitch-deck-analyzer. 4,000+ VC pitch decks reviewed free later, we’ve learned a lot. But more importantly, thousands of founders now know exactly where they stand before walking into a VC...
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