5 Interesting Learnings from Zoom at ~$5 Billion in ARR: Modestly Re-Accelerating Growth, Real AI Monetization, a $27B Market Cap, and a 25x Anthropic Windfall
Almost everyone wrote Zoom off a few years back. The innovative app everyone loved before 2020, but then almost a COVID one-hit-wonder that peaked in 2021 after going from $1B to $4B in ARR in one year. That would slowly bleed out as people went back to the office...
Dear SaaStr: Do Any Top B2B Events Give You “The List”?
Dear SaaStr: Do Any Top B2B Events Give You “The List”? No, no good ones do, and for good reason. Top tier B2B events, especially ones focused on quality over volume, deliberately don’t hand over attendee lists to sponsors as a blanket data asset. If...
20VC x SaaStr This Week : Apple Sues OpenAI, the Token-Maxing Era Begins, and the TAM Question Hanging Over AI Coding
With Harry Stebbings, Jason Lemkin, and Rory O’Driscoll Apple sued OpenAI for trade secret theft this week, and the details are ugly: a six-year Apple employee allegedly walked physical prototypes out the door for show-and-tell, encouraged by a 24-year Apple...
Three $3B B2B Acquisitions in 30 Days: Intercom/Fin, Cognite, and MaintainX. They All Bought the Same Thing: Data for AI
Three $3B B2B Acquisitions in 30 Days: Intercom/Fin, Cognite, and MaintainX In about a month, three B2B companies recently were acquired for right around $3 billion each. On the surface they have nothing to do with each other: Salesforce bought Fin (the company...
The Bay Area Now Takes 51% of Every AI Venture Dollar. And 53% of Every B2B Dollar.
We all know SF is back, and the center of AI and AI+B2B. Carta’s latest data reinforces it. Carta just released its Startup Ecosystem Leaderboard covering the $124 billion invested into startups on its platform from July 2025 through June 2026. The Bay Area took...
Is Software Dead? No. It Just Got a Lot Harder to Win. The SaaStr AI Deep Dive with Rory O’Driscoll
You already know Rory O’Driscoll from our weekly 20VC x SaaStr podcast, where he, Harry, and I go back and forth on exactly this stuff. He’s also been investing in software for 30+ years. Long enough, as he put it on stage at SaaStr AI, to have stayed...
An Hour With Our Top AI Agent Cost $13.42. You Can’t Hire Anyone For That.
Amelia our Chief AI Officer pinged me this morning with a screenshot and three words: “10K making less than … minimum wage.” This is what she was looking at. 10K, our AI VP of Marketing, had just wrapped a focused work session. The summary read: Time...
Dear SaaStr.ai: At What Point Should We Hire an Internal Recruiter?
Dear SaaStr.ai: At what point has a start up do you hire a recruiter internally versus paying recruiters 20% fees? Hire a full-time internal recruiter once you’re hiring 5+ people per quarter consistently. Here’s the math: If you’re paying 20%...
$500M ARR, 60 Engineers, Cash-Flow Positive: How Higgsfield Actually Runs, With CEO Alex Mashrabov
We use Higgsfield almost every day at SaaStr AI. If you’ve watched any of our short videos, the intro to The Agents with me and Amelia, the event promos, the sponsorship teasers, all of it is built on Higgsfield. We’re also a proud early investor through...
Do You Have a “Pricing Gap” Holding Back Sales? Many Do
So recently we had a B2B buying experience that led to a No that is very common but many don’t realize is there, or at least is there that much: A B2B Pricing Gap We went to buy Riverside, a podcasting tool, after years of being on Zoom. We wanted to move to...
Don’t Put AI on Your Hot Leads. Put It on the Ones Your Reps Will Never Call. There’s Millions in Revenue There.
From The Agents, our weekly podcast on how we deploy and run AI agents at SaaStr, and how to do it yourself. The other night I was talking with an AI CEO and their head of marketing, and they told me the same thing I hear constantly: “We tried AI agents on...
Should You Visit More Of Your Prospects In Person? Almost Certainly
I remember the first customer I lost due to not showing up in person. They were a Fortune 50 customer. We did a CSAT survey, and every user loved us. The implementation was flawless. There were zero issues. And … we lost them at renewal. Our buyer was kind...
Dear SaaStr: Should Both Founders Come to VC Pitches?
Dear SaaStr: Should both founders be at investor pitches, or just one is one? Both own 50% BTW. The CEO should always be at every VC pitch. The other founder? It is nice to have them there, especially if she or he can answer certain questions (e.g., product,...
SaaStr Takes on This Week’s 20VC: Why OpenAI Giving the Govt 5% Might Make Sense, the Death of Block Risk, and Why Frontier Models Are the Cheapest
A few days after every 20VC x SaaStr pod, I’m gong to write up the stuff going foward I went deep on, and wanted to go … even deeper on. We covered a lot this week with Harry Stebbings and Rory O’Driscoll, from Washington lifting the Fable 5 ban to...
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