Payman

@lennysan investors. they love it.

Question on my mind right now: What role is least impacted by AI (so far)?

@dharmesh love this!! But also cannot help thinking this is probably a very low risk decision for you, given your overall wealth. The real high risk decision you have already made is to continue leading HubSpot even after 20 years.

BREAKING NEWS: HubSpot co-founder/CTO buys $1.8M of his own company's shares. Disclosure 1: Yes, I'm that guy. (And no, I'm not used to talking about myself in the third person -- will not make a habit of it). Disclosure 2: This is not investment advice. Please do not buy or sell $HUBS shares based on this. So, why am I sharing this and writing about it? Well, for one, at least in my little world, it's noteworthy. It's been a while since I've bought HubSpot shares (I think it was back in 2022). Also, instead of answering the common questions from friends, family and colleagues, I figured it would be easier and more efficient to just answer them just once, here. 1) Why buy more HubSpot shares? Simple. I'm a big believer in the long-term vision of HubSpot and the team driving it. 2) Why do this now? Hasn't the stock been falling? Yes, the share price has dropped considerably despite what was a pretty strong quarter (results reported publicly last week). We added 10,800 net new customers in the quarter (well above the expected range), growing to about 300,000. Revenue, as reported grew 20%+. 2) Why $1.8M? That's an odd number. I purchased 10,000 shares at whatever the market price was. 3) Isn't HubSpot going to get disrupted by AI and agents? I"m biased, but I don't think so. For AI agents in GTM (marketing/sales/service) to do their work they're going to need a platform that can provide the context they need and a work engine that can take action on their behalf. They need a customer platform they can *operate* to do what they need to do and drive outcomes. They're not going to reinvent/rewrite a CRM. They're way too smart for that (and getting smarter). They're going to use what's out there. They'll bias towards systems that have a great Agentic Experience -- not just a great User Experience. (HubSpot will have both. Headless is great, but we don't think completely humanless is a good idea). 4) I heard that others bought shares on the same day. True? Yes. Our fearless leader Yamini Rangan bought shares. Our board chair Lorrie Norrington bought shares too. 5) It's been almost 20 years since you started HubSpot, why don't you slow down a bit?! (That may or may not have been from my wife). :) Answer: I love HubSpot. I love what I do. I'm a builder at heart. I'm up 2am most nights learning, tinkering and building. There's never been a more exciting time to be a builder and to serve small and medium sized businesses. I think we are going to see *millions* of entrepreneurs start businesses leveraging the power of AI. HubSpot's mission is to help them grow better. If you have other questions, leave a reply. Can't promise to answer all of them because...laws and regulations, but I'll do what I can. Cheers.

proud of our teams contribution to this major launch. A privacy win for consumers.

@Chillestdotcom @Nick_Davidov true and you would always know the total fee/carry across layers upfront. You dont have to do your own math to figure it out. I think people are making a bigger deal than they should with this.

Secondary SPVs are not Russian nesting dolls where every layer recharges fresh fees and carry on the same capital. Most of those economics were already borne by earlier investors. The downstream buyer is purchasing an existing position with a negotiated waterfall and exposure profile. The math in this post treats secondaries like newly syndicated primary deals, which is not how most of these structures actually work.

You invested $100K via a 3-layer Anthropic SPV at $380B valuation. Third layer takes 15% management/set up fees and no carry Second layer takes 10/20 First layer takes 10/20 So your real investment is 100*0.85*0.9*0.9=$68.85K. Given nobody scammed anyone in the matryoshka An exit at $1.4T IPO gets you a MOIC of ~2.8x after dilution. That’s $192K on the first layer. The first layer takes 20% carry, you have $167K left The second layer takes 20% carry ($36.4k), you have $130.6k left So you have made a $30K return on a $100K investment in a year. So layered SPV investment got you a 68% Anthropic exposure. Buying Google stock gets you 14% and Amazon - 18%. AND a multiple on all the money Anthropic spends on compute (most of their money). AND exposure to a money-printing business with a strong AI component that rivals Anthropic. AND no scam risk. While the 32% lost in SPV fees just fund someone’s coke habit in Miami. Same $100K put in AMZN and GOOG over the same time period would also get you the 30% return. You’re welcome.

@lennysan @GoogleAI so true! If I was not building/coding, that would be the only AI subscription I would pay for.

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@antoniogm I can understand being stuck in traffic but what is a needless loop? I think it is great feature to cut the ride short and pay for the portion you took + an additional fee :) humans get pissed but AVs should not.

When Waymo is stuck in traffic or doing a needless loop, I just open the door wherever and walk away. Is it smart enough to know the ride is over?Does it travel empty to the destination? I dunno….but I’m outta here.

@jasonlk @Replit @amasad Is this human allowed to sleep?

Ok we're hiring a human to report to the AI VP Marketing we built on @Replit Is this crazy? Is this the future? Could it be ... better to report to an AI? @amasad and I will discuss next week at SaaStr AI Annual 2026! May 12-14 in SF Bay!! Bring your team. Leave agentic experts. For real.

@pitdesi I feel like this is a great way for governmental and non-profit organizations to get funding (a lot less controversial than taxes), everyone is happy. Why doesn't this happen more often?

UofM invested $20M in OpenAI during the same round Khosla invested (Khosla did $50M)… Michigans $20M check is worth $2B, almost 10% of their endowment is now in OpenAI. Heard of another endowment that has a similar exposure to SpaceX

@Jessicalessin @danprimack I think it has already changed a bit in bay area.

@danprimack I hear this everywhere too and I think it is just vibes. They will change again.

Something I heard over and over while in LA for Milken was praise for Anhropic and pessimism toward OpenAI. At lunch, I made a comment referencing GPT. Guy next to me: "You still use GPT? Do you also still have a Hotmail account?"

@a16z not surprising!

@OdyLUNCHBOY @a16z I was gonna ask the same :)

@a16z why is the y axis in $?

@jasonlk @jerseejess @Work_Bench I a human needs to decide whether to use your new software or not it is extremely hard to win. I think the future is to convince the agents to use your software and recommend it. It is a different GTM strategy.

I get that GTM is more important than ever. With 2x-100x more, stronger competitors than 1 year ago. And so many competing for attention of same buyers. But … Was talking with perhaps the best head of GTM I know yesterday coming to SaaStr AI Annual last week, at $10B+ AI leader She said they have no moat

This 👇👇👇!! The only moat we believe @Work_Bench is GTM!!

@philippehebrard totally agree. and I keep reminding myself to tell the agent remember this for all future interactions and sessions. It doesn't always work. Also I feel like the agents should be smart enough to know what is temporary vs. permanent or I am expecting too much :)

@PMohassel The context loss is frustrating. What usually helps is externalizing the key decisions outside the session before they get compacted away. The harness matters, but so does having a durable record of "what was already decided" that survives context resets.

Is it me or is Claude code getting worse? I kept getting frustrated by CC forgetting context and making wrong decision on a personal project. switched to Codex a few days ago. Significantly better! Have not had a single issue yet. I am not sure it is the model or the harness!

@jasonlk why do you think cloudflare sled after hours?

We're back. The B2B Reacceleration Is Real. Twilio, Atlassian, Datadog, Cloudflare, and Palantir just proved it. HubSpot and Shopify still have to. Seven of B2B's most-watched names released earnings this week. Growth is back: 🟣 Datadog: First $1B quarter ever. 32% growth. Stock +28%, biggest pop ever. 5 products at $100M+ ARR. Anthropic on an 8-figure deal. 🔴 Twilio: 4% → 20%. Highest growth in 3 years. Voice fastest in 19 quarters. 🔵 Atlassian: 32% growth, stock +30% in a day. Cloud reaccelerated to 29%. Rovo customers grow ARR at 2x non-Rovo. 🔵 Cloudflare: 34% growth + 1,100-person workforce cut on the same day to "go AI-first." Revenue accelerating, headcount restructuring on the back of internal AI productivity. First time I've seen this combo at this scale. 🟡 Palantir: 85% growth. Highest ever as a public company. US revenue +104%. Rule of 40 = 145%. 11 straight quarters of acceleration. 🟠 HubSpot: Beat the quarter but the "reacceleration" disappears in constant currency. Held the line at 18% CC for 5 straight quarters. Bears were wrong, seats + customers strong. But AI reacceleration hasn't started yet. 🟢 Shopify: $100B GMV quarter. Strong, but pinned in the same 27-34% band for 7 quarters. Q2 guided down to high-twenties. AI commerce is still a slide, not a dollar. 3 things this tells founders: - The "AI is killing B2B" narrative peaked at the bottom. Even the names that didn't reaccelerate held. - Reacceleration shows up as a step-function, not a trend. - AI products tied to measurable revenue lift get rerated. AI features and positioning get a multiple haircut. Atlassian (Rovo +2x ARR), Twilio (voice acceleration), Datadog (Anthropic deal), Cloudflare (workforce restructure on internal AI), Palantir (entire company) all got rewarded. HubSpot and Shopify got sold or held flat. The bottom seems in. For those that have found how to tap into AI budget. Per-seat pricing isn't dead. Vibe coding didn't kill these leaders. But the agents are still coming.

@jasonlk I was not brave enough to hold :(

Datadog destroys earnings, growth keeps accelerating. True AI beneficiary. HubSpot is later today. If it projects acceleration (harder than Datadog to pull off, admittedly), then the SaaSpocolypse is official over. We will see.

@Austen he obviously does not take no for an answer. and that makes for a good CEO!

In retrospect it’s absolutely mindblowing that Sam came back as CEO after this. Reading these threads I would have said 0% chance.

@awilkinson I have had the absolute opposite experience recently.

I want to love Codex, but holy mother of god did they cover the GPUs in molasses? I swear to god it takes 25 min to do something that Claude Code could do in 5 minutes (and yes, I'm using fast mode).

@jasonlk Matches my experience. On every personal project I am building these days with coding agents, I end up needing the first 3 besides the foundation model APIs.

Who's UP in B2B + AI the last 12 months: Digital Ocean +353%: became a real AI cloud with GPU droplets and inference workloads Cloudflare +95%: Workers AI turned Cloudflare into the edge layer for agents Twilio +89%: AI voice agents reignited the communications platform thesis MongoDB +54%: vector search made Mongo the default AI database DataDog +38%: every AI workload needs observability, and Datadog owns it Shopify +13%: agentic commerce and merchant AI tools driving GMV Palantir +9%: AIP became the enterprise AI deployment layer Crowdstrike +8%: AI-native security agents replacing legacy SOC tooling The pattern: every winner has a clear AI infrastructure or AI agent story. Everything else is red.

@0xdoug increasingly, autonomous agents are calling those APIs not individual software workers and agents do not sleep. I would not be surprised if that is a major contributor to exponential growth of revenue. humans do not scale this way.

I’m really struggling to see how the back of the envelope math on this works out… There are generously 4 million characterized “software workers” in America. That’s pretty broad and includes a lot of people who aren’t really classical engineers don’t produce that much code. That comes out to nearly $1k per month of average Claude spend across every dev in America. Yes, there’s some international usage, but it can’t be that much. Yes there is some non software Cowork usage, but that doesn’t use that many tokens. Yes, some non engineers are using Claude to vibe code, but I really doubt many are spending hundreds per month on. Even if we assume 50% of all software workers are using Claude, that comes out to $2k spend per month per Claude user. Thats 10X more than the highest tier Max subscription. So almost all of Anthropics revenue has to be API billing So the only explanation is that something like 20%+ of software engineers are not only Claude users but on API billing and regularly spending thousands per month. At $5/m Opus tokens that means the average API user has to be going through something like 25 million tokens per day. *OR* the other possibility is API revenue is heavily power law dominated. Maybe there’s just something like 100k super users who are making up the majority of the revenue. For that to work the typical super user would have to be spending on the order of $50k/month and guzzling nearly 1 billion tokens per day.