JL
Jason Lemkin
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Jason Lemkin

Things Jason Says on Podcasts

Founder of SaaStr, a community and media platform for B2B software founders, and managing director of SaaStr Fund; he previously co-founded EchoSign, acquired by Adobe. Hosts The Official SaaStr Podcast and appears often as a guest on The Twenty Minute VC, in addition to occasional spots on shows like Lenny's Podcast and My First Million.

“I think agents are an existential risk to DoorDash. … Hey, Harry, did you know that Lemkin's Curry down the street will actually deliver for $2 and you don't need to go through DoorDash? An agent can figure that out for you.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch “Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right?… Anthropic… owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution… They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives… talk about own goals, right?” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch “A billion today is the new $100 million, right? A billion is just the entry point for like a classic B round. In the old days ... Series B investors used to say, as long as it's 100 million or less, it didn't matter because the classic Series B wanted a billion dollar plus IPO.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch “When agents pick you, it's a force of nature right now ... I'm literally building eight to 10 hours a day. And man, my agents have opinions and they're really hard to argue with. And if they want to use a vendor, it's a lot of energy. I know I'm anthropomorphizing it, but it's powerful when an agent decides something.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch “What's the killer app? Another reservation at a Cheesecake Factory or TGI Fridays? We need to see the VisiCalc of Muse.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Where to Find Them

Jason Lemkin hosts and writes The Official SaaStr Podcast: SaaS | Founders | Investors , hosts The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch and hosts and writes SaaStr AI: How To Sell, Scale, and Win . They have also been a guest on The Dave Gerhardt Show (from Exit Five) (2 times) , Lenny's Podcast: Product | Career | Growth (2 times) , My First Million (2 times) , Turpentine VC" | Venture Capital and Investing , Marketing Against The Grain , This Week in Startups , TBPN and StrictlyVC Download .

Recently: “20VC: OpenAI Cuts Valuation to $1.25TRN | Public Market Meltdown: GOOG Loses $500BN in 12 Hours | DoorDash Buys Instacart for $17BN | Kalshi Raises $1BN and Cognition Eyes $80BN Valuation” on The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (November 2026); “20VC: Anthropic Files S1 Ahead of $2TRN IPO | Instinct's Rumoured $30 Billion Fundraise | Microsoft Laysoff 27,000 While Meta Taps Equity Markets for $95 Billion Capex Spending Spree” on The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (October 2026); “SaaStr 883: The AEO Playbook: How to Get Picked by Agents (The Agents #017)” on The Official SaaStr Podcast: SaaS | Founders | Investors (October 2026); “20VC: Trillion or Bust: The New VC Game | Coreweave Sell-Off Creates Panic | Town at $1B, Anduril at $90B: Revenue Multiples Out of Control | General Atlantic Eyes IPO & Modal Raises $750M at $15.75B” on The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (October 2026); “20VC: The Pro-Rata Battle: Valar Atomics Sues Day One Ventures | Meta Returns to the AI Frontier With Muse Wonder | NVIDIA Eyes $30B Reflection Deal & Jev Raises $870M at a $7.5B Valuation” on The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (October 2026); “20VC: Cognition vs Factory: Vinod Khosla Creates a Storm | OpenAI Nears $70B Run Rate: Anthropic Under Threat | ElevenLabs Doubles Its Valuation to $22B & Salesforce Buys Listen Labs for $2B” on The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch (October 2026).

What They Said

“I think agents are an existential risk to DoorDash. … Hey, Harry, did you know that Lemkin's Curry down the street will actually deliver for $2 and you don't need to go through DoorDash? An agent can figure that out for you.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Discussing DoorDash buying Instacart, and DoorDash's remark that AI agents placed only a few hundred orders against millions of daily deliveries, Lemkin argues an agent could route around platform fees by finding restaurants' own delivery.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-11-05 Permalink → Listen →
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 28:08 into the episode
Speaker 2

…behavior happen more and more? And then how does DoorDash respond to it? You know, they're all doing versions of the same thing, which I mean, I could totally see for some of your standard food orders, just it's not that much easier for the record. I mean, telling your agent to order your dinner,

Rory O'Driscoll

it's just as easy as to just go click on the DoorDash app.

Jason Lemkin

Well, but there's a thing. DoorDash has two competitor, big competitors. It has Uber Eats, right? And it has the restaurant. The restaurants don't want to use DoorDash or Uber. So most restaurants have self-pickup. At least they have to-go pickup where they can avoid most of the fees, right? Or self-delivery. An agent can figure that out for you. Hey, Harry, did you know that Lemkin's Curry down the street, actually, it will deliver for $2 and you don't need to go through DoorDash or whatever they have in London? I did not know. Thank you, Muse. Thank you, Instinct. I'll take that. That'll save me $14 on my order. What's the pub right behind your office that I really like, Harry? The Grazing Goat. Love that place. Five out of five, okay? Maybe they could just drop it off at the next time we do the pod for free. I don't have to pay 20% and plus tip plus this. You think I'm kidding? I think agents are an existential risk to DoorDash Buys their number three competitor is nobody. Can

Harry Stebbings

I put out a cultural difference between us? You guys pay 15 bucks a burger and it gets delivered at 50. And there's like federal charge, state charge, delivery charge, service charge. It's ridiculous. In London, it's kind of like 15 quid is 15 quid. It's fascinating to see the difference in like…

Speaker 2

Yes. And that's

Rory O'Driscoll

why these businesses are widely profitable. They figured out exactly how to extract every dollar of rent from the person who wants to sit on their couch, press a button and get the meal an hour later.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right?… Anthropic… owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution… They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives… talk about own goals, right?” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Lemkin's reaction to Anthropic's S-1, after Rory O'Driscoll said OpenAI's leadership should be reflecting on decisions that let Anthropic pull ahead. Lemkin lists what he sees as OpenAI's self-inflicted wounds, above all ceding coding for about a year.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-10-29 Permalink → Listen →
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 13:27 into the episode
Harry Stebbings

Fasamultman reading this, thinking about Q1 going out himself, do you think he takes away anything from it, changes anything as a result of it?

Rory O'Driscoll

…away from you and do better. If there's any self-reflection, there should be a ton of that going on. Nothing you can do about it. You just got to get your business together and converge and get out yourself. And in the meantime, obviously compete aggressively on price to try and screw up their Q3.

Jason Lemkin

Never has such a successful startup maimed itself so poorly that I can think of as OpenAI. I mean, it would have killed almost any other startup what they went through, right? With the CO drama, all the other nonprofit to profit drama, the spike startup doing better than them. They basically let Anthropic control part of the market for almost a year, which is like five years or 10 years in AI time, right? There is a certain amount of parity with Astra and the OpenWaits models today, the best, but Anthropic fucking owned the playbook for the chessboard for almost 12 months. There was no point in using any other coding solution. And coding is the killer app, as Rory said 100 times. The math is true. They literally letting Dario walk out the door rather than build it in-house and then firing the CEO and bringing him back over the night of long knives. I mean, my God, I mean, it's all going to be okay. But talk about it, talk about own goals, right? I mean, every startup's full of them. This is just, these are some epic ones.

Harry Stebbings

I had the joy of having Sachinadella on 20 VC earlier this week. Great show. It was a fantastic guest to have on. Warden Orner. Microsoft had some pretty big news. That they were offering voluntary buyouts to 60,000 of its 223,000 employee base. It's an enormous amount of the employee base to get…

Jason Lemkin

First of all, Rory may have observed more of these than I have. Maybe he hasn't. I hope he hasn't. But it's not like all 27% are going to take it. Right. And they've already been through, I already think they already went through a 10% layoff round, right? So they've done, it's some sort of…

Rory O'Driscoll

Yes. I don't know. Whether 7%

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“A billion today is the new $100 million, right? A billion is just the entry point for like a classic B round. In the old days ... Series B investors used to say, as long as it's 100 million or less, it didn't matter because the classic Series B wanted a billion dollar plus IPO.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

In a mock investment committee, Harry Stebbings asked whether they would back a Series B at a $1 billion valuation. Lemkin passed, calling it a classic early-stage bet "with a bow tie," while saying he regretted passing on a much larger round in Modal.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-10-22 Permalink → Listen →
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 37:08 into the episode
Rory O'Driscoll

Probably in some simplistic who's the winner, you're probably right, those are the three biggest. But maybe the stimulus is, I don't think it's like the hyperscalers where no one else mattered.

Harry Stebbings

…to decide that you're probably going to do modal at 15.7 billion. Yeah. And so if we call an investment committee, there was another round that was announced, which was town at a billion dollars. I think it was $108 million Series B. Are we going to do this from our growth fund, Jason? Well,

Jason Lemkin

…Even if the margins never hit the 40s, we make money on this deal. Like, there's just no question that the markets crash. Town, I'm going to pass on, Harry. And if you and Rory and the rest of the team want to do it, I'm fine with it. You know, a billion today is the new $100 million, right? A billion is just the entry point for like a classic B round. In the old days, when the three of us met, Series B investors used to say, as long as it's 100 million or less, it didn't matter because the classic Series B wanted a billion dollar plus IPO. They wanted their 10X, so 100 million, 80 million. They didn't care, right? So a billion is the new 100 million. Town has no data. It's sort of interesting revenue. It has a smart team. This is just a bet. This is just an old classic Series A, Series B with a bow tie at a billion. And if you want to, if this is one of the 10 you want to make in the next 12 months, just do it. I just consider it…

Harry Stebbings

we're not doing it, Jason. Well,

Jason Lemkin

I mean, the good news is the team only predicts it needs about 500 million of inference over the next 12 months. So that's much better than the Instinct team, which needs 5 billion. So in a sense, I like it for the fun because we're a little more conservative than our peers. So all we need to do is…

Harry Stebbings

you rather do Instinct at 30 billion or town at a billion? All

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“When agents pick you, it's a force of nature right now ... I'm literally building eight to 10 hours a day. And man, my agents have opinions and they're really hard to argue with. And if they want to use a vendor, it's a lot of energy. I know I'm anthropomorphizing it, but it's powerful when an agent decides something.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

The panel is discussing a hosting company said to be getting half of its new business from AI agents, up from 3% at the start of the year. Lemkin's point is that software agents now choose which tools to build on, and that as the human in the loop he finds it takes effort to overrule them.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-10-08 Permalink → Listen →
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 47:40 into the episode
Dev Ittycheria

We're doing about 100. So 9x. Which, by the way, was right on the heels of the GFC. So the market was getting quite skittish in 2008.

Harry Stebbings

…up from 3% at the start of the year. Jason, I always find you quite mind-expanding for me when you talk about these topics. How do you think about this? How much budget we should give to agents for 2027? What's the takeaway for us from Versal now getting 50% of new business from agents up from 3%?

Jason Lemkin

…at 600 million from 20% increase in customers or something. I mean, the expansion revenue is astronomical. And it's just the thing is when agents pick you, and I'm sure Dev's thinking a lot about this, right? On the database side, when agents pick you, it's a force of nature right now. And agents, what I've learned from, well, you have 21 agents. We're building all day. Between me and Amiel, I'm literally building eight to 10 hours a day. And man, my agents have opinions and they're really hard to argue with. And if they want to use a vendor, it's a lot of energy. I know I'm anthropomorphizing it, but it's powerful when an agent decides something. And Vercel is a major beneficiary of this. Even last year, it looked great, but it never seemed it would be as important as it is today. Oh, that's just, that's just where I'm going to stick my code, right? Important, but back office infrastructure. But man, this is where so many agents and apps are running. And I would only want, I would take this one to the IC too.

Dev Ittycheria

I think this is really interesting about the point that Jason made is that agents are picking, making decisions, right? But for the last 25 years, every marketing person, every company has optimized how you show up on page one of Google, right? You educate human buyers. Now you have to make sure…

Harry Stebbings

You know, when I look at this market, we too have a company, Dave, Peak, and everyone's like, well, this is just like a next generation of SEMrush. Is it just a next generation of kind of SEO analytics providers with your profounds and your peaks? Or is this actually a much larger category?

Dev Ittycheria

I think the opportunity is more than just analytics by telling you where you're missing and all that. I think the opportunity for these companies is not just tell you what you're missing, but to help shape the content and create the content to help you solve that problem. If they can close the…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“What's the killer app? Another reservation at a Cheesecake Factory or TGI Fridays? We need to see the VisiCalc of Muse.” — Jason Lemkin, The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch

Lemkin is skeptical of Meta's Muse agent. He says every horizontal platform has needed one killer app, that OpenClaw never found one, and that restaurant bookings and carpool scheduling are not it. A moment later he admits Muse is beautiful and fun to use.

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · 2026-09-17 Permalink → Listen →
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch Around 23:48 into the episode
Harry Stebbings

What do you mean, does it matter? Sorry.

Rory O'Driscoll

Yeah.

Jason Lemkin

What's the killer app? Another reservation at a Cheesecake Factory or TGI Fridays? We need to see the VisiCalc of Muse. We need to see what is the killer app. Every horizontal platform needs a, you know, traditionally needs some sort of Killer app, right? I'm just skeptical. I'm just wondering, right? I don't think in this whole thing, I don't think there was a killer app for OpenClaw. And I don't know if there is a killer app for Muse because, or Instinct, because there wasn't one for OpenClaw.

Harry Stebbings

Is it not being your discovery mechanism to shopping? Like a WeChat, a super app? You know, Zuck has spoken about taking portions of transactions as being the business model as well.

Jason Lemkin

The model's good, but what are his examples? Scheduling his daughter's carpool. Is that really what a trillionaire needs to do with a general? He can't even come up with a good use case of Muse for himself. He's making up consumery things. I had to schedule ballet lessons from my daughter. I mean…

Harry Stebbings

I don't know if it needs to be. And I know that sounds stupid, but no, but I use Instinct in a similar power user way. I think latency is a real problem with Instinct, by the way, which might not be with Matt. I wait for responses. Minutes. It's like the first days of Chat GPT. It's a real problem.…

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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