Double Down on Winners: Increase Ownership Every Round
I'm a co-investor with a mega VC fund we don't talk about as much here but they are wildly successful in many top IPOs and top decile returns. And they have a really simple way they do follow-on checks: ✅If the company is doing well, they increase their ownership in each round. Period. They don't need to be on track for a $100B exit ... at that time. They don't need ElevenLabs growth ... at that time. They just need Very Good Growth, and to be doing better and better than before ... and they increase ownership in every round. Period. No debate, no drama. And they just tell the founders that. Does this make sense on paper vs concentrating all reserves in your 1-2 proven winners? I don't know. It's contrary to much VC advice out there. But I can tell you it works for them. Or at least, it doesn't not work.
Zoom Jumps 10% as Anthropic Stake Finally Priced
Zoom is up 10% today, or about what its Anthropic position would be worth (I'd guess closer to 50x than 85x). It's trading at a $28B market cap as of right now, and its Anthropic position is probably worth ~$2-3B. Insane this...
Free Ultimate Guide for First-Time Angel Investors
We wrote the ultimate angel investing guide to help first-time angels. And it’s 100% free. More>> https://t.co/IiGiQKSHBR
Lower‑Middle Market M&A Thrives;
I’ve had so many conversations with founders who tell me they almost sold during ZIRP, then decided to wait because they were sure the market would only get better. They expected multiples to keep rising, capital to stay cheap, and buyers...
Stop Talking, Start Building AI Solutions
There’s an AI GTM startup I really like the founders of, they’ve been asking us for 6+ months to try them. I appreciate the emails, calls, DMs, etc. And the endless offers to “get on the phone” to see a...
Deal Flow Quality Trumps Picking Skill for VC Success
Deal Flow Quality beats “picking skill” The figure below is a reminder that most VC chest-thumping is aimed at the wrong variable. In venture, outcomes are driven by two levers: >Pool quality (base rate): how many real winners exist in what you see >Picking...
Customer Success Benchmarks: Pay, Staffing, and P&L Guidance
“How the hell do I plan for customer success?” -How should I pay the CS team? -Where should it go on the P&L? -What ratio should I use to staff it? -How big should the team be? Here are the...
Entrepreneurs Often Run Jobs, Not Independent Businesses
Many entrepreneurs think they’re independent simply by starting their own business, but if you have a complex cap table, a bank loan that’s always on your mind, or silent (or loud) partners who see things different ways, there’s a very...
Full-Team Commitment Fuels AI Startup Success
🤷♀️"AI Native" startups don't have access to better LLMs 🤷They often don't have smarter engineers 🤷♂️They don't know the space any better 🤷♀️Their sales team are often tiny and mediocre So why do they win? 100% of their team wants to do, and are willing...
AI's Rapid Progress Outpaces Bubble Concerns, Driving Profits
"There’s pockets of bubble-ish dynamics. But the technology is improving so fast, there’s so much more room to improve, and companies accelerating in AI are printing money."
AI Era Triples ARR per Employee, Winners Pull Ahead
Per @a16z, the gap in ARR/employee has widened dramatically in the Age of AI $700k per FTE vs. $200k per FTE You're either pulling away here, or falling way, way behind https://t.co/6CD2h5yM6X
Investors Diverge, Favor B
Five founders pitched, and these investors came to wildly different picks. Maxwell Weiss, of Pacific Bays Capital, and Fred Almeida, of American Medical Intelligence, chose B2B SAAS startups building for air quality testing and supply chain risk.
AI Generates Real‑Time Investor Flow Reports From X
How much value is locked up here on X? Or, what is the money doing in AI? I had @blevlabs's AI (a state of the art cognitive architecture that works a lot better than Grok or ChatGPT for these kinds of...
Data Room Activity Reveals Buyer Seriousness for Better Negotiations
All of our clients use a data room. A data room is a secure, online document repository to host important resources related to selling a business/raising capital. The primary reason for utilizing data rooms is to stay organized and make...
AI Startups Outperform Non‑AI: Higher ARR, Faster Growth
👨🦳Non-AI startups: - Lots CSMs (vs FDEs) - AI agent is slow / not truly great, not #1 focus of company - Not gaining market share - Customers don’t want to pay 2x-10x more for AI Agent (honest truth: not great) - Still very large...
PE Shifts Away From Vanilla SaaS, Seeks AI Growth
There’s a tough topic that it’s time to be honest about in 2026: PE is no longer coming to the rescue. It was a great run. From 2012-2023 or so, almost any B2B or SaaS company that hit $20M ARR,...
Founders Overraise, Ignoring YC’s “Default Alive” Wisdom
YC’s best advice is “default alive” - have enough cash to survive without the next raise. Great advice… nobody f*cking does it. Paul Graham (the founder of YC) once said he’d raise $500K, get ramen profitable, and probably never raise...
Venture Funding Hits Decade Low Amid AI Optimism
For decades, venture capital has expanded practically by default. More funds, more managers, more capital. Today, fundraising, firm formation, and LP participation are all moving in the same direction: down. After 20+ years, we are now facing the first meaningful...
AI Agents: Cost‑Effective Workers Who Never Quit
"Why did we go all-in on AI Agents?" with @kylecnorton CRO @kylecnorton "I just got tired of paying folks six-figures, letting them work from home with plenty of agency ... and still quitting. The AI Agents aren't perfect. But they...
Cracking B2B AI Pricing: Experts Share Proven Models
How do you price AI features in B2B? Per seat? Per outcome? Usage-based? Founders are still figuring this out in real-time. At SaaStr AI 2026, we're bringing together the ones who've cracked it. May 12-14. SF Bay https://t.co/4l6Rm5He3B
GitLab Spurs 12.8% Rally, SaaS Index Up 3.
📊 https://t.co/D1x4RaX5t7 Market Pulse - Thu, Jan 22 The https://t.co/D1x4RaX5t7 Index delivered a strong performance on January 22, 2026, with an average gain of 3.47% as 23 out of 25 stocks advanced. GitLab led the rally with a remarkable 12.82% surge,...
Gain Control in 2026 with a Simple Cash Flow Forecast
A simple forecast lets you see what’s coming before it arrives. It helps you test scenarios, plan hiring or investment, and make choices without holding your breath. If 2026 is the year you want fewer surprises and more control, start here. We’ve...
Growth Trumps Efficiency in AI Era IPOs
A tough truth: getting more efficient, getting profitable, might have been necessary the past few years for many. But it also got you … nowhere. The markets still reward growth far more than efficiency. You do need both now when...
Deep Dive: AI Trends and Investment Strategies with Nathan Benaich
Fun convo going deep on all things AI and how to invest in it with the 🐐 @nathanbenaich
The Term “Seed Round” Is Officially Retired
We are now officially retiring the term "seed round". Thank you for your attention to this matter. https://t.co/NzL2sy9dUJ
SMBs Trade Higher Volume for Lower NRR than Enterprises
In theory, SMB > Enterprise More customers, much faster sales cycles, faster PLG and viral cycles But even 100% NRR is tough to hit with SMBs, While 120%-140% common in Enterprise Most SMB SaaS goes at least bit enterprise or at least into more...
VC Success Lies in Platforms or Specialists, Not Verticals
This is actually a very interesting discussion. It's near consensus now that the only strategies that make sense in VC is large platform or small specialist. So it's kind of a hot take to say that verticalized venture doesn't work. A couple...
Most Series A Founders Overestimate Their $50M Worth
I talk to delusional Series A founders every day. I now just send them this post. If your company does under $10m ARR, burns over $200k/mo and has low Gross Retention, you are not worth $50-100m dollars to ANYONE despite...
Clean Data Rooms Accelerate Startup Sale Success
Selling your startup isn’t just about finding a buyer. It’s about being ready when they show up. Due diligence kills deals every day. But the real reason isn’t product quality. It’s when buyers hit sloppy org, missing docs, unclear metrics, and they...
AzimutGroup Pours €110M Into D‑Orbit Space Logistics
Italian asset management co #AzimutGroup invests EUR 110M ($129M) into space logistics/transport perovider @D_Orbit - EUR 45M as part of D-round capital raise, + EUR 65M in purchases of D-Orbit shares from existing shareholders. https://t.co/m03h44pTbC
Capital Efficiency and Aggressive Growth Can Coexist
Today NextView’s portfolio company Hatch was acquired by Yelp for $270M. Having led the company’s seed round and served on the board, I’m grateful for the journey – and the lessons learned from founders Chris Bache and Bill Violante 👇...
Khosla and Rabois Reveal How Tech Titans Collaborate
New Uncapped with two of the greats, Vinod Khosla and Keith Rabois . I don't think I've seen them on a podcast together so I was especially excited about this. I asked them about how they work together, how they...
AI Cuts Sales Headcount, Supercharges Top Reps
GTM tools made the mid-pack reps more effective. That was the story from 2005-2024 or so. They created repeatability and efficiency so that 50%, 70%+ of your team could run the exact same playbook and at least hit quota. Many...
Build for the Problem, Not the Solution
In the late 90s founders raised hundreds of MILLIONs for new fax technologies… But when was the last time you faxed a document? Startups need to be PROBLEM-centric, not solution-centric. Fax technology was focused on making faxes work better, rather...
High‑growth SaaS Firms Thrive While Low‑growth Tumble
Will designers design first in a world where AI can code software immediately, or just describe the design? Will large enterprises pay for premium observability when AI can migrate & monitor open source competitors? As Michael Mauboussin writes , there’s...
Founder Resilience Beats Funding: Mission over Money
When investing in founders, do you check for their karma? Shinichi Takamiya of Globis Capital Partners says he does just that. Looking for spiritual motivation, NOT moneyed interests. Shinichi points to how the best founders are deeply rooted to their...
Real AI Value Lies in Unglamorous, Time‑Bleeding Work
Enterprise AI strategy is backwards. Most people are focusing on Chief AI Officers and pilot programs, when the real value is in the unglamorous work where organizations bleed time. More thoughts:
Upsell & Cross‑sell Boost M&A Valuation
As a SaaS company, the benefits of being able to up-sell or cross-sell a customer go beyond just growing your revenue base. When the time comes to start conversations with strategic buyers or investors, your ability to grow the average...
Sell to the Buyer Who Gets Your Vision
Maxime Berger (@MaximeMB_) didn’t sell BlogBuster to the highest bidder on @acquiredotcom. He had a lot of options and fit was the deciding factor. Some buyers came from totally different industries. Nothing SaaS. Nothing product-led. And Maxime kept thinking about his...
OpenAI Shows U.S. Can Lead AI Through
OpenAI's work here is proof that America can win the AI race and invest in the communities that house the infrastructure to make American AI exceptional.
Learn How to Build True AI-First B2B Companies
Be honest: Do you actually know how to build an AI-first B2B company? Or are you just bolting GPT onto your existing product and hoping? SaaStr AI 2026. May 12-14. SF Bay. Come learn from founders, execs + leaders who've...
Shifting Focus: Exploring Consumer AI After Diverse Investments
our last 10 investments were: - 3 dev tools/infra - 3 vertical niche b2b - 2 deep tech - 1 consumer hardware - 1 general agent would be fun to look at some consumer AI this quarter
Sarah Lacy Unveils Decade-Old Pando Videos, Including Thiel Talk
Sarah Lacy is putting her Pando video archives online, for the first time in YEARS. She just dropped a 2012 discussion with Peter Thiel, and also has an interesting 2026 reaction video from her (which i'll thread in comments below)...
Consistent AI Bull: From Early Bets to 2026 Momentum
me/air street 2014: begin investing in ai startups 2016: what wall st misses on nvidia 2017: why go long on ai 2021: the ai revolution is just starting 2024: ai is not the dot com bubble 2025: a monumental 12 months in ai 2026: lesgooooo ref:...
Pre‑ vs Post‑Money SAFEs Can Crush Returns
That SAFE you signed might tank your returns 😅 If you’re new to angel investing, you’re about to hear “SAFE” a LOT. Here’s the tiny detail that can quietly crush your math: pre-money vs post-money. 🧵 https://t.co/J3udlaBTtA
Expert M&A Advisory Guides Founders to Maximize Exit
What sets @acquiredotcom apart? Our M&A advisory. We guide you through every step of your acquisition to maximize your exit. This M&A Insights Call showcases how Rainier Nanquil leads calls and gives guidance to founders. Learn more here: https://t.co/5hGUQheGfG https://t.co/6GklAPQyK5
Balance Finite Wins with Infinite Growth Strategies
Businesses must play both finite and infinite games. Finite games have known players, rules, and objectives - the goal is to win. Landing a sale. Hitting a milestone. Infinite games are timeless and have unknown players, rules, and objectives - the goal...
AI Powers the Next Evolution of Data Stacks
After a decade of success, the modern data stack has entered consolidation. What comes next? The postmodern data stack is AI. The modern data stack created more than $100 billion in market cap with a simple promise : move the data via...
Visible, Honest CEOs Accelerate Startup Growth
What I see CEOs at struggling start-ups do: - Go dark - Hide - Lash out - Tweet about lots of things non-work - Invest time on tiny expenses - Argue internally What should do: - Be Present - Be Honest - Be the Rock - Be Realistic/Optimistic You just plain grow...
Fintech Secures 11% Venture Funding, Second to AI
Fintech is quietly back in the spotlight. It now captures 11% of global venture funding, second only to AI. Rounds are getting larger, and investors are focusing less on hype and more on business models that actually scale. The signal matters. As...