How much do the top marketplace businesses take per transaction? Some charge more than you’d think… “Take rate” is a function of: Purchase frequency × ticket size × platform labor intensity The more work you do, the more juice you get. Three takeaways from the research: 1) 100% of the marketplaces I looked at charge the Supply (Seller) side. This makes sense, as they are bringing them (hopefully net new) business. 2) Of the 25 marketplaces I dug into, more than half monetized both sides of the transaction. For some, this more than doubles their effective total take rate 3) Some marketplaces may be going too far. To quote Bill Gurley “In order for your platform to be the “definitive” place to transact, you want industry leading pricing – which is impossible if your rake is the de facto cause of excessive pricing.” Shutterstock and Class Pass are examples. H/T Dan Hockenmaier and Lenny Rachitsky for their prior marketplace research which I leaned on Read the full marketplace take rate analysis here: https://lnkd.in/g6AaZSNG
if Indiana can go from losingest team in NCAA history to undefeated and CFP champion in two years, you can get to 3x DPI on the late stage SaaS portfolio you invested at 97x ARR in 2021
Sand Hill has done a great job selling their capital. But if you don’t fit a certain “archetype” (either in demographics, category, or geography) and strike out on Sand Hill, then there’s plenty of other investors elsewhere. For example: look...
What are the basic phases of a process (M&A or capital raise)? 1. Pre-marketing Complete the marketing materials (information packet and buyer list) and get your house in order. 2. Marketing Reach out to buyers, execute NDAs, and share marketing materials. 3. First-round bids Receive Indications...
It’s scary when a startup competitor becomes well-funded. But what I’ve noticed is that while they may be able to overpay on customer acquisition in the near term, it catches up to them. If you can weather the storm for...
I had a wide ranging chat with Eléonore about Intercom, Fin, and a variety of topics * Why did we need to drop everything and run to AI immediately, and do so regardless of the cost. * Building reliable AI...

Introducing Fast Round. We built a tool to help founders fundraise. How it works: • Enter your X username • See which investors follow you • Send a DM • Get $$$ But seriously, I hope it's useful. If you want to give the beta a try, the...

A good business in a bad market often sells for nothing. A great business in a strong market can sell for something that actually changes your life. That’s where we are right now. > Strategic buyers are buying tech to move faster. >...
The best B2B companies are now running with 30% humans and 70% AI agents. Or even higher. The old GTM playbook is dead. At SaaStr AI 2026, we're going deep on what the new playbook actually is. And what really...
“Can your team ship AI features that make you truly smile? If you don’t smile — your customers won’t either” Traditional enterprise software and SaaS is under assault. The leaders are all still growing, but in many cases slower than ever....
AI is changing every GTM role. You can run from it. You can argue with it. Or ... you can learn to dominate the new world at SaaStrAnnual.com 2026. Join us.
VC autism contest: Who can name the most startups that have raised a Series B. If you get a single one wrong, you’re eliminated at that number. Whoever gets the highest wins.
Even without a lot of data points, often founders truly know whether customers love their product or not. But it’s easy to delude oneself. Mostly because of sunk costs. But if you’re really honest with yourself, you know your answer.
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...
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
📰 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...
🧠♻️ https://lnkd.in/gGt8wQmK
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...
If the company was going well, a lot of founders I know who sold their companies later regretted it. Because success compounds, they lost out on the revenue compounding over the next several years. AND, when you start a new...
I wonder how much of Stripe’s margin comes from junk fees that aren’t on any of the pretty dashboards, only the CSV that takes 24 hours to generate.
How do we see vertical Software M&A and fund raising shaping up for 2026? A lot of founders we speak with are trying to figure out what 2026 might actually look like if they're thinking about raising capital or selling....
Today, if there’s a good idea, prepare to see 100s of it. There’s a lot of sameness. In this market, leadership excellence wins. @marissamayer's experience is a major edge, but so is her ability to know how to put it...
The first 3 years of starting a company really wears you down. Finding product-market fit is hard. But once you get some success and push through that wall, that’s when it gets good. Unfortunately, too many people run out of...
I got so much positive response to my previous post about hosting a VC AI tool show and tell that I created a form to capture interest - if you'd like to stay in the loop please fill this out...
Postscript 's Chris Brubaker is not afraid to color outside the lines of finance. In fact, it may be his superpower. As a master at partnering with sales and an advocate for finance leaders to have tech skills past the...
One of the things that surprised me about YC is how long we continue to advise founders. We thought we'd just help them get started and then hand them over to later stage investors, but in fact we're still talking...
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
I see this pattern over and over in great exits. Founders don’t start by trying to sell. They start by solving a real problem well. Arman Iranpour (@ArmanIranpour) and Matt Aleali (@aleali_mahdi) were real estate investors frustrated by how slow and...
The strategic problem for openAI is that if the input box isn’t the product, then either the product is dozens of new apps or dozens of features in existing apps, and that means they’re competing with every startup on earth...
The Mega-Fund Math vs Reality Below is a simple case study on fund math. People are asking if a16z can really do a 3-5x on a $15B fund. To 3x net on $15B, you need ~$45B back. Assume ~5% ownership at exit. 👉 That...
I caught up with a portfolio founder who is doing super well. Profitable. Throwing off $1m+ in annual cash. Growing quickly. Doesn’t need to raise. But he didn’t take a holiday break - because he’s the bottleneck. If your company...
1/ The Back Door Is Open How Acute Infection Could Make Anti-Infectives Investable Again Anti-infectives never died. The business model did. Low prices. Short courses. High resistance risk. Pharma walked. Now look at Alfasigma stepping into HSV encephalitis. Small deal. Narrow indication. Big implication....

I passed on Airbnb in 2008. My note to the founders said I had "concerns about travel-oriented startups." A masterpiece of missing the point. Here's what I got wrong: https://t.co/syj5L8gRxz
I think the truth that few investors like to swallow is that the best companies really never needed them. Either for their money or their advice and connections. Those companies would’ve been great anyway.
Retell AI is one of the strongest companies we've invested in -- they've got an incredible team and product, and outlandish growth. They're hiring their first product manager if you or anyone you know might be interested: https://lnkd.in/gvRtGBXw

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...
Congrats to Tracy Young Ralph Gootee and the TigerEye Team. So proud to work with this team all these years and can't wait to see what they do as a part of Lennar.
As a founder, I found that one of the hardest things about fundraising is managing the fundraise and the business at the same time. Both are full time jobs. And doing both haphazardly is the worst of all worlds.
New Job 2026, part X No, not for me, *for you*! Thread AI is based out of NYC and has built the platform the help companies and public sector actually use AI. Two amazing founders - Mayada Gonimah and Angela...
🚨 Lean AI Leaderboard Update A new speed record was just set. Higgsfield AI went from $100M → $200M run-rate in 2 months. Let that sink in. Here’s what makes this unprecedented 👇 • $200M run-rate in < 9 months...
Most founders don’t realize how exposed they are until they’re already in a deal. One buyer, one offer, one path forward. At that point you’re not negotiating, you’re just trying to get to the finish line without losing it. The buyer feels...
I've had a lot of fun sharing AI-powered tools I've built to help us run Precursor, and I have learned a lot from folks like Sarah Smith and Chang Xu based on what they are doing. I am thinking of...
If you’re struggling to raise, I think it’s sometimes helpful to ask yourself how someone would’ve built this business when the venture capital industry didn’t exist. Some of the techniques founders used back then were GOAT. Reading business / startup...
The first startup ideas tried to build were awful. We built too much. We built without close rapport with customers and built the wrong things. This was pre Lean Startup. Fast forward. Now that everyone knows about the Lean Startup...
In 2008 / 2009, when founders said they couldn’t raise money, they meant they literally couldn’t raise anything. Now when people say they can’t raise money, they mean they can’t raise more than like $100k.
What does it mean to be a founder-focused investment bank? Founder-focused means that a bank is fully unconflicted and focused on the interests of founders. In other words, the bank doesn't accept revenue from anyone that could be a buyer...

Sometimes, it takes a little dilution to reach Trillionaire status Where will you land? Try https://t.co/NlPWFTrkQ8 https://t.co/kU3hxso4IY
Much has been said about the challenge of standing out in VC, amid a growing pool of competing capital. Nothing works better than actually doing the work, delivering, performing. Thank you @dunn for your trust ⭐️
Startup people reach for the word “pivot” when they want a decision to sound intentional. I’ve seen teams use it for everything from a careful course correction to quietly walking away from a plan that stopped holding up. Same word....
Stop waiting for your startup’s product to be perfect because it never will be and that's okay so launch, get feedback, improve.