20VC x SaaStr This Week: Navan’s “Disappointing” $5B IPO, VCs Getting 6% Instead of 20%, and the Fire-Half-Your-Team AI Test: The New Venture Reality
We’re back! Harry, Rory and Jason this week. The venture landscape has fundamentally shifted. A $4.5B exit is no longer enough for mega-funds, ownership targets are getting crushed across the board, and if your SaaS company didn’t see AI-driven...
You Can Hide From a Lot of Things as a Founder. Cash Burn Isn’t One of Them.
I’ve been doing this long enough now – 8 years on some boards, 100+ investments across two funds – to have seen every flavor of founder challenge at least 10 times. The VP Sales that isn’t working out. The product roadmap that’s six...
10 Coolest Things You Can Do on the New SaaStr.ai
So we’ve been building the new SaaStr.ai for a while now, and the traction has been pretty wild. 500,000+ valuations run. 30,000+ new users. 1,600+ VC pitch decks analyzed every month. And we’re just getting started. But here’s what I’ve...
The Problem(s) With T3D2 Venture Deals. They’re Still Great. But They Might Get You Fired.
Is Triple Triple Double Double good enough in B2B venture deals anymore? You know the path: $1m ARR → $3m ARR → $9m ARR → $18M ARR → $36m ARR → rocketship. Here’s the thing. On the one hand, of course it is. That compounds to 50%+ growth at $100m+ ARR....
Dear SaaStr: I Don’t Really Feel Confident Enough to Call Myself “CEO”
Dear SaaStr: As a startup CEO, I don’t feel confident to call myself CEO even though our company makes positive revenue and goes in the right direction, Is it normal? Yes, it’s pretty common. We’ve all felt this way, myself included. The CEO of Atlassian shared...
Dev Steps Down as CEO of MongoDB: The Beginning of the End of an Era?
When the Board asks if you can commit for another five years, and you can’t answer — that’s the signal MongoDB announced that Dev Ittycheria is stepping down as CEO after 11 years at the helm. CJ Desai, formerly of Cloudflare, takes over as the next CEO....
Your Seed Round Now Needs to Last 3+ Years: What 3,365 Startups Tell Us About the New Series A Timeline
The TL;DR: If you raised your seed round in the past few years you have a 39% chance of taking 3+ years to raise your Series A. That’s double the rate from just three years ago. Carta just analyzed 3,365 US startups that raised a Series A between Q1 2018 and Q3...
AI Wins When It Does The GTM Work … People Won’t
Our AI SDR just booked a sponsor meeting for us (six figure deal) on Saturday night at 6:02PM while we were out to dinner 0 humans would do this pic.twitter.com/dJ8vAFolhC — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 19, 2025 The Customer Meeting That...
How to Price Your AI-First Product: The Death of SaaS Pricing and the Rise of Transactional Models with Defy Ventures’ Medha Agarwal
Medha Agarwal is a Partner at Defy VC, where she focuses on investments in AI-first and vertical SaaS companies. She shares insights at SaaStr AI Summit 2025 from the front lines of AI-first product pricing, exploring why traditional SaaS models are declining in favor...
Nasdaq Reaches Another ATH. Nvidia Tops $5T. But Navan’s IPO and JAMF’s $2B Exit Show B2B Still Isn’t Easy.
Times are good But Navan IPO’ing at ~$5B at ~$800M ARR run rate And JAMF selling for ~$2B at 3x ARR Well, they do make me wonder about some VC rounds these days — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) October 31, 2025 The Nasdaq hit another all-time high this...
AI App of the Week: Assistant UI – The React Library That’s Eating the AI Chat Interface Market
Why 450K+ monthly downloads and Y Combinator backing signal this is the developer tool AI product builders have been waiting for Here’s a question every B2B founder building with AI has wrestled with: How do you get ChatGPT-quality UX into your own product...
Why The Top Quartile in Venture is Brutal Today: When “Doing Great” Isn’t Enough to Raise Money
We’ve been running SaaStr’s AI-powered pitch deck analyzer for a few months now, and we’ve graded and analyzed over 1,600 (!) pitch decks. The pattern is clear and honestly pretty brutal: founders are building fundamentally strong companies that...
Dear SaaStr: As a Co-Founder, When Do You Know It’s Time to Quit?
Dear SaaStr: As a Co-Founder, When Do You Know It’s Time to Quit? You don’t. Why? Because 50% or more of the time, it’s because you are tired. And when you’re tired, you don’t always make the right decisions. Before you quit: Talk to 2–3 mentors you trust. See...
VCs: Want More Dealflow? Sign Up for SaaStr’s AI Dealflow
SaaStr’s new AI VC has been a big hit already with founders: they’ve already uploaded, 1542+ VC pitch decks to it we’ve done over 556,387 (!) startup valuations And … we’ve also been quietly doing founder <-> VC automated AI intros...
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