Just got an investor update from a 10+ year old vertical SaaS company I invested in a looong time ago. Founders never quit, know space cold, but man it’s been a grind. And they are far, far from “AI Native”. However … They finally used AI late last year to automate a critical type of data collection and analysis that could never properly be done before for their customer base. The customers love it. Love it. It makes the product radically more valuable. Interest exploded. They had 5x the attendance at their webinar than ever before. And now, for the first time since founding, they are back to 100% growth. Not Harvey-ElevenLabs-Replit growth. But back to 100% growth for the first time since … maybe 2017? This can be you, too.
Strange World Indeed, 2026 January edition: - The worst time in our history to be invested in public software stocks - The best time in our history to be invested in private hot (AI fueled) startup stocks
You can scale infinitely as a CEO or VP if you are relentless in recruiting people truly better than you to work for you You will slow down within months if you recruit VPs and execs under you that aren't
📰 Top AI+B2B News - Sun, Jan 18 https://t.co/MWFHfEuzpm Top Stories: 1. Musk Seeks Up to $134 Billion Damages From OpenAI, Microsoft 2. ClickHouse Lands $15 Billion Valuation in AI Database Race 3. Figma (FIG) Is Down 13.2% After AI Deal With OpenAI Top SaaStr...

The video tackles the hype around turnkey AI sales agents, debunking the claim that simply turning on a product will instantly generate revenue. It stresses that successful AI‑driven go‑to‑market requires feeding the system the language and tactics of a company’s...
"When you have 5, 10, 20+ AI GTM agents ... you need a hub. And for the most part, that hub is @salesforce today. It's a Renaissance for @salesforce." with @kylecnorton CRO @owner https://t.co/IaEh5Zt3Gh
10 years ago, VC was optimized around $1B+ outcomes, for the most part. 5 years ago, VC was optimized around $10B+ outcomes. Today, VC is optimized around $100B+ outcomes. It’s exciting and bold and startups in the Age of AI...

The short video argues that artificial‑intelligence agents can now close sales as easily as a text message, positioning AI as the next frontier in revenue generation. It spotlights LennyBot, a conversational AI that can converse by text and voice, and...
So this year we’ve built an AI VP of Marketing for SaaStr. The v1 at least. We didn’t want to, we wanted to buying an AI agentic solution that does what we need in marketing. But we just couldn’t find...
Before $20,000,000 in ARR Maybe even before $50,000,000 in ARR Do not hire anyone with "strategist" in the first few lines of their LinkedIn bio

The video argues that traditional, email‑driven Sales Development Representative (SDR) positions are on the brink of obsolescence, with AI expected to replace roughly 90% of those roles by next year. It frames the shift as inevitable, suggesting that the classic...
"Which AI Agent vendor should you pick?" with @kylecnorton CRO @owner "The lowest hanging fruit is adding AI to Inbound. To instantly qualify deals, instantly answer customer querstions, and instantly set up a meeting with a human AE." https://t.co/TUcLRTLEiB
When I started using @Replit last summer, agent v1, you didn’t really know if anything you told the agent to do … would really work in practice when it created the code. You hoped. But you just didn’t...

Back in the day, folks talked about Sand Hill VCs going to Bucks and doing deals over breakfast But the hipper VCs were in Palo Alto. And they did breakfast at Il Fornaio Another one that couldn’t make it in...
This is also true with GTM agents The very best agents for sales, marketing, support, post sales can also function as strong general agents with just a bit of work That means all are going to compete with each other to win...
"You can't just hand an AI Agent to the sales team or marketing team to deploy. Not if they don't have the skills to implement the agent, train it, manage it." with @kylecnorton CRO @kylecnorton "You have to find that GTM...
250,000+ B2B founders and operators in the SaaStr community. For 3 days in May, we're all going to be in the same place. SaaStr AI 2026. May 12-14. SF Bay Area. If you've ever gotten value from SaaStr—this is the...
One thing that has really really accelerated the past 12 months is your partners competing with you. Expect the trend … to continue even more, and much faster, in 2026. The pace of the AI Age is leading to partners becoming competitors...
I think the hype around “vibe coding” has confused what it really does, and why it’s actually so disruptive. It’s not about “one shotting” Salesforce or Notion. That’s just not possible. You can’t build anything like that in 100 days...

Sometimes, it takes a little dilution to reach Trillionaire status Where will you land? Try https://t.co/NlPWFTrkQ8 https://t.co/kU3hxso4IY
If your AI feature, your AI product, your AI team, your AI copilot didn’t materially boost revenue … 👎 It doesn’t count Try again
"My CEO says we need to do AI, but my CFO won't give my budget. What do you we do?" with @kylecnorton "The answer: start with one AI Agent that solves a high ranking problem ... that is easy to deploy."...

Typical equity rich, cash poor founder on https://t.co/E5wtQ9xial $370B net worth, but only $19M liquid https://t.co/oF2st2owCX
ElevenLabs will probably be worth more than Twilio by mid-2026 Really seems like a missed opportunity there
So at the end of the year I wrote an investment down to $0, my biggest write-off so far. $4m to $0. But my co-investor? He marked up his investment. From about $15m to $30m. How is this possible?...
For a long while, you probably aren't a great CEO But you know the customers The software The feature gaps The roadmap The competition How to sell it How to market it How to build it So maybe as flawed as you are You are still the best CEO
"AI can't beat the best sales teams," like CRO @owner + @kylecnorton. "No way." "But can it beat the sales folks that less hot startups hire? The 'mid pack' sales folks? The ones that never really learn the product? Yes....
Hot take: 90% of "AI features" shipping in B2B right now are terrible. The companies winning are doing something completely different. Come to SaaStr AI 2026 May 12-14 and learn what actually works from founders with the receipts. https://t.co/Ff7DKVt1H2
Yes, VCs often have a “liquidation preference” But there is also a “founder preference”. It’s called retention payments, which can often be eight figures on top of any return from common. And are often structured in a way to...
Old rules: Around Year 5, the Competition Catches You in Whatever Made You Special Around Year 10, you have an Existential Threat. The tech world has changed so much, what you started with is sort of irrelevant. Today, with AI, often happens...
If you're a VP of Sales, CRO, CMO, or Head of Product at a B2B company and you haven't figured out your AI strategy yet... May 12-14 is your deadline. SaaStr AI 2026. SF Bay. Come with questions. Leave with...
My take on California’s “One-Time” Billionaire Tax. It’s much worse than it looks. 📉 Will it pass? Yes, likely. It only needs 50%+1 voter approval. SEIU + CTA have done this before—Prop 55 won 63% in 2016. ⚖️ Will it...
"If I had 2 more great humans, I'd hire them tomorrow. If they were truly great. But a Pretty Good AI agent is better than ... hiring a human that isn't great. We don't need placeholder hires anymore. AI Agents...
Never hire anyone in sales that doesn't care about money You'll see
Everyone’s focused on Brin and Page fleeing California. But there’s a ticking time bomb buried in the billionaire tax: Mark Zuckerberg may be facing a $49 Billion tax bill he literally cannot pay. 🧵 The California billionaire tax has a provision that...
The one hire I don't need, and none of my portfolio cos need, is a "Strategist" I know at certain stage in many folks' career, that's what they want to do Advise on strategy more than do work themselves No criticism But most startups...

Alphabet completed a $32B acquisition of Wiz (cloud security with AI-powered threat detection) in March 2025, expanding its cloud and AI security capabilities. The deal is cited among the largest AI-driven strategic acquisitions of the past 12 months.
Omni has received strategic funding from ecosystem players Snowflake and Databricks to accelerate go-to-market and partnership credibility. The investment is described as a strategic alignment to speed up integrations and market entry; financial terms were not disclosed.
OpenAI completed a roughly $10 billion secondary sale, creating significant liquidity for insiders and early investors and generating numerous new millionaires. The secondary underscores strong late-stage investor appetite for AI assets and intensifies competition for AI talent.
The article references Anthropic's oversubscribed $10 billion funding round for its foundation-model business, highlighting massive investor demand amid broad AI investment trends. The raise is presented as a major capital event underpinning growth in AI infrastructure and products.
CoreWeave secured an $11.2 billion debt package to help finance roughly $22 billion in capital expenditures for AI data center capacity. The raise positions the company as a bellwether for AI infrastructure demand, hinging on long-term customer commitments to match...