SaaStr, every mention
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every year anyone Harry Stebbings 133Jason Lemkin 124Sam Blond 6Jason Calacanis 6Beezer Clarkson 6Nicolas Dessaigne 4Ara Mahdessian 3Scott Dorsey 2Ryan Petersen 2Ivan Mazour 2
Verbatim, from the transcripts: the passages where SaaStr comes up
NVIDIA Crushes Quarter | OpenAI Cuts Off Cursor | Instinct Hits $2.5B Valuation
- ▶ 1:06:50 Jason Lemkin And the marketing annoyed me that every CMO, um, at like Sastre annual two years ago was buying clay.
Should American Enterprises Work With Open-Source Chinese Models? | Only 10% of Neo-labs survive
- ▶ 1:13:26 Harry Stebbings My dear friend Jason Lampkin from Sasta, who we do a weekly show with on News with Rory, um, said that we'll give a 100,000 dollars of tokens to our best engineers.
OpenRouter CEO: Why Chinese Open Models Are Beating the US | Why Enterprises Fear OpenAI & Anthropic
- ▶ 40:59 Harry Stebbings I literally just had my dear friend Jason Lankin, you run SAS to come back and be like, couldn't figure out what time Starbucks opened on Deep Seek.
Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
- ▶ 26:18 Jason Lemkin So I'm building an app for the Sastra community.
- ▶ 26:21 Jason Lemkin It's called Sastra Connect to help with recruiting.
Should the US Ban Chinese Open-Source Models | OpenRouter's Chance To Sell | Stripe Buying PayPal
- ▶ 39:33 Jason Lemkin I've been building this agentic recruiting app just to recruit from the Saster community.
Enterprises Fear Frontier Models | Sam Altman Offers Trump 5% of OpenAI | DeepSeek Builds Own Chips · 20VC with Harry Stebbings
- ▶ 1:08:16 unnamed speaker This is a public company said, you're going to have to wait three weeks to fix a fact that your AI is still talking about SASTR, 2026, which already happened. 2 times in the scene
Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
- ▶ 1:05:07 Jason Lemkin Go to Sastrad AI.
DeepSeek Raises at $50B | The Rise of Open Source vs OpenAI & Anthropic | OpenAI Builds Own Chip · 20VC with Harry Stebbings
- ▶ 43:37 unnamed speaker We just got, we had a human that for Sastr AI annual this year, Aurora was at, forgot to invoice 80,000 dollars of revenue we had to write off. 2 times in the scene
Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
- ▶ 43:46 Jason Calacanis I would take, we've already made that choice at Sastra.
- ▶ 45:46 Jason Calacanis CS Summit at our Sastry annual event.
- ▶ 1:17:09 Jason Calacanis And this is where, and Andrew Bilecki, CEO of Klaviyo, he came to Sastor AI annual this year, and he talked about what they're doing in AI.
OpenAI & SpaceX S1 Drops | Layoffs at Cloudflare & ClickUp | OpenRouter & Polsia Raise Mega Rounds · 20VC with Harry Stebbings
- ▶ 1:03:27 unnamed speaker It researched sastardoc.ai.
Why Anthropic Are Causing a Comp Crisis & Why You’d Never Hire From Salesforce or ServiceNow · 20VC with Harry Stebbings
- ▶ 15:41 Harry Stebbings Well, this was going to be one of my questions, which is, uh, Jason Lamkin from SAS, a kind of famous SAS investor, said on a show recently with me, multi-year contracts, but they mean less than ever, because if you don't have usage,…
Anthropic Raises $30BN at $900BN Price | SpaceX Files S1: How Does it Trade | Cerebras Smashes Day 1 · 20VC with Harry Stebbings
- ▶ 14:32 Jason Lemkin On the other hand, I do think, I hate to use myself as a N equals one case, Stace, but, but at SAS for itself, Amelia and I have, now we have 21 agents of which three are autonomous, okay? 2 times in the scene
- ▶ 40:55 Jason Lemkin We had a little Napa retreat break after Sastry annual this year, and it, the, the, the, the Tesla took us the long way through the South Bay, which I haven't done in a while, rather than the bridge.
- ▶ 1:10:04 Harry Stebbings Jason, Rory is a celebrity at Sasta.
Anthropic Buys Compute From Elon & Commits $200BN to Google | Cerebras IPO | Ramp Raises at $40BN · 20VC with Harry Stebbings
- ▶ 10:23 Jason Lemkin This is a classic Sastra post.
- ▶ 59:38 Jason Lemkin Yeah, I, I, I, you know, certainly we're going to rebuild our financial stack after Sastra annual and, and we will move from Brex to ramp if it is the most agent friendly and automating procurement is a huge bonus.
- ▶ 1:04:46 Harry Stebbings Sasta this year, who will be the best speaker?
- ▶ 1:11:16 Jason Lemkin This was one of the first Sastra posts I ever wrote right when I got out of Adobe, and it took me a while to realize this.
Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings
- ▶ 2:38 Jason Lemkin It's up 60% this year, the highest ever, the highest ever.
- ▶ 57:52 Jason Lemkin So, but a funny thing is, so we built this AI VP of marketing and AI VP of customer success at Sastra.
- ▶ 59:35 Jason Lemkin It's gonna be a little higher this month because of Saster Annual, but not much, man.
- ▶ 1:18:10 Jason Lemkin I mean, I met Tom once through you when he was at Sastra London.
- ▶ 1:30:49 Jason Lemkin So last night we had our AI VP of customer success reach out to 120 sponsors for Saster Annual, asking them exactly what their issues were, telling me everything they had to do and get it done.
Inside Clay's Sales Playbook | Becca Lindquist · 20VC with Harry Stebbings
- ▶ 52:42 Harry Stebbings I am friends with Jason Lemkin from Sasta.
Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
- ▶ 1:19:01 Jason Lemkin Can I put them on the Saster Fund website if I do the, the, the, uh, the underlying entities?
Replit CEO: Why the SaaS Apocalypse is Justified & Why Coding Models are Plateauing | Amjad Masad · 20VC with Harry Stebbings
- ▶ 3:34 Amjad Masad You know, we were talking about Jason Lemkin earlier from Sastr.
Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
- ▶ 23:19 Jason Lemkin This might be, and I remember back in the day at Saster Annual, Ryan Smith came and, um, Qualtrics had just been acquired for seven billion and our jaws dropped back then.
- ▶ 56:35 Jason Lemkin Jason, how come I can't unsubscribe to your goddamn Saster newsletter?
- ▶ 1:14:32 Jason Lemkin And so for example, like after Sastre annual in May, we're going to build our own AI VP of finance, our own.
OpenAI Kills Sora & Hits $100M ARR on Ads | Oura Going Public & Whoop Raises at $10BN · 20VC with Harry Stebbings
Why You Need a $1B Fund To Do Series A | SpaceX at $2TRN & Data Centers in Space | Groq's $20BN Deal · 20VC with Harry Stebbings
- ▶ 11:56 unnamed speaker We have like 200 sponsors for Saster and all the humans would quit because it was too much work.
- ▶ 59:11 Harry Stebbings I mentioned meeting him for the first time at SAS to Jason, if you'll believe it, 10, 1011 years ago, uh, in a side room.
NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
- ▶ 10:40 Jason Lemkin This is not a unicorn trying to figure out what to do with the last twenty million that Saster scale and 20 VC gave it.
- ▶ 20:38 Harry Stebbings In terms of how you run Sasta. 2 times in the scene
- ▶ 26:27 Jason Lemkin I mean, I remember, I guess it was maybe Saster annual 23.
Anthropic vs The Pentagon: Who Wins? | The Data Center Arms Race | The Ultimate Stock Picks · 20VC with Harry Stebbings
- ▶ 1:02:08 Jason Lemkin Go to saster.ai and make me a better version.
Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
- ▶ 36:01 Harry Stebbings Dude, I, I'm very good friends with Jason Lemkin from Sasta, who on a show with me very recently said, oh, this picking winners early stage stuff.
Citrini Research Breakdown: Agents, "Ghost GDP", Consumer Spend | Figma Earnings Beat · 20VC with Harry Stebbings
- ▶ 40:29 Jason Lemkin Our 10 agents at Saster generate millions of revenue, but they buy nothing.
- ▶ 1:19:05 Harry Stebbings Jason, would you leave SAS to do a five hundred million fund with me and Rory?
OpenAI's Codex Lead: Why Coding as We Know It is Over · 20VC with Harry Stebbings
- ▶ 16:07 Harry Stebbings One of my dear friends is Jason Lemkin from Sasta, and he says that actually inference is the new sales and marketing.
Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings
- ▶ 40:11 Jason Lemkin That won't, that wants to do a six-figure sponsorship at Saster on its own.
a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
- ▶ 25:34 Harry Stebbings Um, Jason Lemkin's a very good friend of mine from Sasta.
20VC: From $6.2BN Market Cap to $2.8BN: What Is Not Translating About Navan's Public Story | Are Any Public Company CEOs Actually Happy? | Why Navan Built It's Own Customer Service AI and What it Could Mean For Customer Service AI with Ariel Cohen
- ▶ 37:05 Harry Stebbings Jason Lemkin said on a show the other day to me, I'm sure you know Jason from Sasa.
The SaaS Massacre: Public Market Collapse |Microsoft Lost $360B & NVIDIA’s $100B Dispute with OpenAI
- ▶ 35:52 Jason Lemkin Um, they ended up being small sponsors for Sastra because they made millions, but I really don't get any benefit out of it. 2 times in the scene
Groq’s $20BN NVIDIA Deal | Why Sam Altman Doesn’t Care About Dilution & Invisible Unemployment 2026 · 20VC with Harry Stebbings
- ▶ 51:14 Jason Lemkin But I've put so much of my life into Claude over the last, every, every, every, every 20 VCs in it, every Saster thing is, is in my Claude and it can search all of that history for 14 months and self named itself.
Predictions for 2026: Top Buy & Biggest Short | Why Salesforce Could Win & NVIDIA’s Challenges · 20VC with Harry Stebbings
- ▶ 24:06 unnamed speaker I went back, we did a Saster annual during the Corona, during the pandemic in 20, 21.
- ▶ 26:11 unnamed speaker Like when we were at, we were in Sastra London a couple of weeks ago, um,
- ▶ 31:17 unnamed speaker You know, when I go back, I was thinking the earlier days when I started investing, I remember Byron Dieter came up to the old Saster office by, you know, ran the cloud practice at Bessemer.
Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
- ▶ 1:13:55 Jason Calacanis I can tell you, we do work closely with the, with a lot of the folks at Google Cloud with Saster.
Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings
- ▶ 11:53 Jason Lemkin I mean, when we had, uh, when we had the CEO of Snowflake at Sastre Annual in May, just starting to talk about how they were going to use agents, right?
Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
- ▶ 54:49 Jason Lemkin I can tell you, this is like an old saster lesson.
- ▶ 1:04:18 Jason Lemkin Cause I look at going to, if I just pull them up in my little tier on Sastrad AI, if you're growing less than 20% of a, of a cherry pick basket, 5.1 X AR, Wix is lower.
- ▶ 1:09:34 Jason Lemkin So listen, Sastr itself, we're multi, we're not as big as TwentyVC, but we're multi-channel. 2 times in the scene
- ▶ 1:20:26 Jason Lemkin I tried to write it up on Saster.
Peter Thiel and Softbank Sell NVIDIA - Why? & Why VC Will Hit $1TRN and The Opening of Retail · 20VC with Harry Stebbings
- ▶ 3:52 unnamed speaker So if we were talking earlier in the year, even if we were at Saster in May, we'd be talking about, I was at, we were talking about productivity boosts, right?
- ▶ 28:16 unnamed speaker We essentially have 12 AI agents running now at Sastra more than humans.
- ▶ 1:12:53 unnamed speaker You know, just one, since we have Tom here, um, uh, I don't want to go over, but I, I just wrote it up today on Saster.
Michael Burry Shorts NVIDIA and Palantir & Has Defensibility Died in a World of AI? · 20VC with Harry Stebbings
- ▶ 16:24 Jason Lemkin I can tell you what I learned from both, but we use Gamma at Saster. 4 times in the scene
Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
- ▶ 21:57 Jason Lemkin I, hold on, let me put it in the Saster AI, eight billion, the Saster AI, uh, valuation calculator says. 2 times in the scene
- ▶ 1:04:20 Jason Lemkin And that, that's why I think agent force is so important because, you know, we've, we, we have this thing on Sastra, Sastra.ai.agents where we share all the agents we use.
OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings
- ▶ 45:19 unnamed speaker I also read, Jason, your blog, the blog post on Sastr, and I think your characterization of the, your characterization of spray and pray is wrong.
Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
- ▶ 17:56 Jason Calacanis We have four humans and 12 AI agents at Saster, but my gut tells me,
- ▶ 1:23:28 Jason Calacanis He said he would share all the data at Saster.
20VC: The Startup Adding $1M ARR Every Week | Competing Against OpenAI's Codex and Claude Code: Who Wins | Why Gemini is Failing and GPT-5 Is Winning | Do Margins Matter in a World of AI | The Ugly Truth About AI Coding with Zach Lloyd, Warp
- ▶ 14:55 Harry Stebbings One of my friends is Jason Lamkin from Sasta, and he says that we'll get to a stage where it could be up to, like, 10,000 dollars per month.
Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings
- ▶ 36:56 unnamed speaker I Vibe Coded eight apps in a hundred days, and we have 12 AI agents working at Sastra now.
OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings
- ▶ 1:13:18 Jason Lemkin You know, I remember when Michael Cannon Brooks came to Sastra, which was a long time ago, Sastra Annual, and he said, we had the CEO of Trello interview him right after he got acquired. 2 times in the scene
Are Burn Multiples BS in an AI World? & Sam Altman Needs $1TRN of Energy · 20VC with Harry Stebbings
- ▶ 1:11 Jason Lemkin I wrote it up on Sastr, uh, this week.
The Impact of H1B Visas on Startups in the US & NVIDIA Invests $100BN Into OpenAI · 20VC with Harry Stebbings
- ▶ 1:16:50 unnamed speaker I'll, I'll, I'll bet you that Saster tattoo. 2 times in the scene
Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
- ▶ 57:43 Harry Stebbings This is like the PLG for Sasta.ai. 2 times in the scene
Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
- ▶ 27:14 Jason Lemkin They bought, uh, scale seven or SASTR one at a 20% discount, immediately marked it up because the, uh, to, to, to, to mark to market, and the funds up 20%.
Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings
- ▶ 57:45 Jason Lemkin Now it's Aster up from zero at the start of the year. 2 times in the scene
- ▶ 1:24:09 Jason Lemkin If we're lucky, it's not as easy, but if we're lucky, Saster Inc. will do twenty million this calendar year with two people. 4 times in the scene
- ▶ 1:33:51 Jason Lemkin Well, look, for what it's worth, Alex Karp's always been my dream since the beginning of Saster.
20Sales: $0-$3.7BN: The Databricks CRO's Playbook to Build the Fastest GTM Engine in SaaS History | How Databricks Beat Snowflake | How To Build a Sales Org of 5,000 and Close $190M Deals with Ron Gabrisko
- ▶ 38:40 Harry Stebbings I am with dear friends with Jason Lampkin from Sasta.
Why Apple Needs a Management Overhaul & Why Google is Catching Up with Hyperscalers · 20VC with Harry Stebbings
- ▶ 4:23 Jason Lemkin We actually had brands, quirky brands, Sastron, 20 VC, but we under, I think, especially today, we underestimate how powerful it is to meet a founder and say, you're from benchmark.
- ▶ 34:22 Jason Lemkin Until I ran like four different AIs for Saster.
- ▶ 1:07:14 Jason Lemkin I just remember September, 22, September, 20, 22 Saster annual was in September then, and the Adobe deal acquisition happened and it, no one talked to 10,000 people talked about nothing but Figma.
How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings
- ▶ 31:37 Jason Lemkin Tell me about Saster and where it's going. 2 times in the scene
Windsurf x Google x Cognition: Full Breakdown: Who Made Money, Who Did Not · 20VC with Harry Stebbings
- ▶ 46:57 Jason Lemkin And we already use Lovable at Saster, don't get me wrong.
20Growth: The Death of Growth Teams? | How Hubspot Use AI to Triple Email Conversion | The Future of AI SEO | Why Prompt Engineering is the New Coding | What Every CMO Needs to Know About AI in 2025
- ▶ 27:53 unnamed speaker I didn't mean that badly, but like with that ratio, holy shit, me and Jason at SAS to talk about this a lot.
Figma’s IPO: The Full Breakdown & Why Melio’s $2.5BN Acquisition is “Discouraging” · 20VC with Harry Stebbings
- ▶ 47:59 Jason Lemkin Yeah, I had them even present at Sastra Annual this year.
- ▶ 1:04:13 Jason Lemkin We're writing Saster Fund to copy this.
Navan Files to Go Public and Canva Pulls the Brakes: Why and What Happens? · 20VC with Harry Stebbings
- ▶ 27:59 unnamed speaker Well, all the legal work I do, both for the fund and for Saster Inc., everything, I run through my AI and Claude, and then I run it by my counsel to see if it's correct.
Elon’s Empire: SpaceX, Tesla, Neuralink After the Storm & Anduril’s $2.6BN Power Move · 20VC with Harry Stebbings
- ▶ 1:16:05 Jason Lemkin And that's a big, that's probably a 48% gamble because it's, it's easy to see them coming down on the side of the content providers and maybe Sastra gets a check. 3 times in the scene
Fiverr CEO & Founder, Micha Kaufman: "If You’re Not Adapting to AI, F* You. You’re Done!" · 20VC with Harry Stebbings
- ▶ 9:42 Harry Stebbings My subsequent question then, without sounding bleak is, yeah, I'm very friends with Jason Lemkin from Sasta, who has quite a bleak summarization on this, but he says, yeah, and no one wants to work today.
Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
- ▶ 54:08 Jason Lemkin She's, Erin and Yamini at Sastor this year.
- ▶ 56:06 Jason Lemkin My, my son helped us at SAS Granul this year.
OpenAI’s $6BN Jony Ive Deal & YC Is Both Chanel and Walmart, and Has Officially Won! · 20VC with Harry Stebbings
- ▶ 49:24 Jason Lemkin I mean, literally out of SAS Daniel this year, one of the, one of the, one of the folks that helped put us on, he rewrote the best summary of the day that day of his day.
- ▶ 1:03:27 Jason Lemkin You know, I thought when I, when I read that, um, I, it sounded to me like every backstage conversation I had at Sastre annual this year with public company CEOs, which is.
Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
- ▶ 1:01:19 Jason Lemkin There was literally 50 times more energy at Sastr this year than last year.
OpenAI, SBF & Perplexity: What VCs Know That You Don’t · 20VC with Harry Stebbings
- ▶ 1:00:51 Harry Stebbings Uh, and then Jason's got Sasta. 2 times in the scene
- ▶ 1:08:13 Jason Lemkin Literally, we were at a Sastra pre-event last night, and I'll tell you everything I heard about Clay.
- ▶ 1:19:49 Harry Stebbings Jason, good luck for Sasta, dude.
Benchmark vs a16z: Why Stage Specific Firms Win · 20VC with Harry Stebbings
- ▶ 33:06 Jason Lemkin I mean, literally, we, even at Sastra, we've gotten rid of five people in our team in the last 90 days due to AI. 2 times in the scene
What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
- ▶ 35:12 unnamed speaker You know, it's funny, Harry, when you and I were in London this last summer at the Sastre Europa, there was a CEO speaking, um, and he told me that he's in a WhatsApp group of, and they're at scale, they're at nine figures in revenue.
- ▶ 44:40 unnamed speaker We've had over a 100,000 on Sastra AI.
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