Welp, that happened faster than I predicted. Thought it would be end of 2027, then early 2027, but agentic traffic growing so fast that bots have now passed human traffic online for the first time in the Internet's history. https://t.co/2zX5bHdhsa
This is easy to dunk on but regular reminder that Brookline should not exist. None of this tax revenue will help Boston whatsoever, which surrounds like 90% of Brookline.
Liberals in Brookline, an affluent suburb of Boston, voted by a 20-point margin to RAISE their property taxes by 18% - a $23.25 million tax override. And they’re CELEBRATING it! Massachusetts residents already pay some of the highest property taxes in America. INSANE! #mapoli
Ramp TOP SAAS VENDORS MAY 2026 @tryramp
1. FIGMA is a fastest growing vendor, and the only publicly traded company on our list. Now competing with Claude Design.
2. AI inference platforms grew as businesses opted for cheaper models to combat exploding token budgets.
3. It's a great time to be in web deployment (Vercel, Netlify, Lovable)
We are cooking, y’all, come join.
I’m also looking for someone to own our fintech product lines from a growth perspective, and someone to lead the PLG product team.
SEGMENT, ALWAYS SEGMENT
Most confounding business problems have the same root cause: you haven't segmented your customers.
You look at the top-line number. It's flat, or weird, or inconsistent with what your gut tells you. You poke at it and you can't figure out why. The answer is almost always that you're staring at an average that's hiding two or three very different stories.
A few places this shows up:
1. When your high-level metrics look wonky or divergent, break them out by segment. A flat retention curve often hides one cohort churning out violently and another expanding aggressively. A "meh" NPS usually has one segment of fanatics and one segment of detractors cancelling each other out. The average is a lie. The segments are the truth.
2. When your product is trying to be everything to everyone, you need to tailor it per segment. If your roadmap has SMB founders, mid-market IT buyers, and Fortune 500 procurement all fighting for features in the same backlog, that's three products in a trench coat pretending to be one. Pick the segment you're actually building for, and ship accordingly.
3. When your pricing or positioning feels wrong no matter where you set it, it's because one SKU or pitch is spanning segments with wildly different needs or willingness to pay. Enterprise will pay 10x what a startup will for the exact same thing. A single price point either leaves money on the table at the top or closes the door at the bottom. Segment the packaging. Segment the price.
The pattern holds every time. Whenever a business problem is hard to reason about, break the population into segments and look again. Nine times out of ten, the fog lifts.
Importantly, you don't need to use standard gender or demographic segments. You can build your own! (And AI is a superpower here).
One of the best segmentations in real life was done by @davidweiden at TellMe Networks in the early 2000s. TellMe was selling phone automation software into financial services: a half-billion dollar market, and they had almost no traction. David built a custom segmentation framework called Rifle, which scored every prospect on five weighted criteria. Where the customer was in their buying cycle (engage before the RFP, not after). Whether their long-distance carrier was compatible with TellMe's deployment model. Three more criteria with explicit weightings, including negative scores that disqualified prospects outright. The whole company aligned on the scoring. Sales stopped chasing bad-fit accounts. Product stopped building features for customers who would never close. Marketing stopped spraying the market. Over two years, Rifle drove $20M in ARR inside the qualified segment and took TellMe from a loss to a profit. They literally would have failed without the segmentation. .
Founders: when a metric confuses you, when your product feels scattered, when your sales pitch or pricing won't land, segment. Segment, always segment.
A pretty rough article came out today re the Massachusetts economy (see in reply). While I agree with a lot of the problems, a lot of the builders in Massachusetts are working very hard to make it not just a great place to start companies, but also a great place to scale companies. Recent progress:
1. YC - There are a lot of folks helping fog the runway for a YC return to Massachusetts. In @agupta we trust.
2. DeltaV - This is MIT's incubator that got a $6million infusion of cash and programming reboot from @abialecki and @edhallen of @klaviyo fame.
3. TechWeek - This is going to be a major event in Massachusetts this year. Big boost happening.
4. Sequoia - Running programming in Massachusetts. Thanks to @abhishekm1636
5. Mass AI Coalition - A major initiative across all of tech in the state led by @willahmed and @durkin
6. Government - The mayor, governor, @epaley and @Barry_Finegold are starting to face reality and are engaging in the problems. Green shoots include a statewide partnership with OpenAI and a citywide initiative to teach AI in all the schools. I'm really hoping to see real "action" from our representatives on building housing and improving transportation.
7. MIT - MIT's president and provost have kicked off their CATE CATE (Committee for Acceleration Translation and Entrepreneurship) initiative that I'm hopeful will have a big impact.
I'm sure I'm leaving out a ton more. What am I missing @lindahenry, @alexwg, @patk, @HenryLSchuck, @mikey, @BillAulet?
Major League Baseball is aired in the morning for Japan. So technically they eat breakfast with it being on television.
Here’s their #openingday commercial. No hyperbole, when I say this, it might be greater than any US MLB commercial I’ve seen. Well done and worth the watch for any baseball fan.
Also true for PMs, at least at @Rippling...
- No more planning decks, only markdown pushed to a git repo
- Customer issues identified in ~realtime using LogRockets scanned via MCP
- PMs fix your own damn copy slop 🤣
really crazy how much it has changed