# AI to AE's: Grit, Glean, and Kleiner Perkins' next Enterprise AI hit — Joubin Mirzadegan, Roadrunner Latent Space · 2025-12-12 Joubin Mirzadegan, a Kleiner Perkins partner who incubated Glean and now leads its next bet, Roadrunner, argues that AI-native CPQ can fix the broken quoting workflows that plague enterprise sales. Starting the CRO-only podcast Grit as a hiring wedge, he built relationships that later helped Glean and Windsurf scale. He explains why technical founders need sales leaders with a chip on their shoulder, not just fancy logos, and why Windsurf succeeded by marrying Google-class product with Salesforce-class distribution, hitting $100M ARR in months. Roadrunner rebuilds CPQ's data model from scratch, co-develops with four hairiest design partners, and aims to use LLMs to recommend deal structures, automating the Slack-channel chaos of deal desk. ## Questions this episode answers ### What is Roadrunner and why is Kleiner Perkins incubating it? Joubin Mirzadegan says Salesforce CPQ is excruciatingly slow and CIOs at companies like Uber and Box independently rate CPQ as their top problem. He realized LLMs can reason with deal data, but incumbents can't easily rebuild broken data models. Roadrunner is rebuilding CPQ from scratch, co-developing with four design partners that have the hairiest pricing models to create an infinitely flexible data model, and plans to use LLMs to recommend deal structures. [39:01](https://addtry.com/d1728182-04b3-4aba-b1ef-c30df2051f8a?t=2341000) ### What anti-patterns should startup founders avoid when hiring their first sales leader? Joubin Mirzadegan warns founders not to be fooled by shiny logos like Snowflake; sales hires must have experience at similar-stage companies because early-stage sales is more art than science. He shares that at KP's top eight portfolio companies, 38 out of 40 executives reported to the CEO for the first time, proving that context and growth potential matter more than résumé credentials. He also stresses that AI salespeople must be more technical than ever. [30:30](https://addtry.com/d1728182-04b3-4aba-b1ef-c30df2051f8a?t=1830000) ### What techniques does Joubin use to make podcast guests comfortable and get authentic conversations? Joubin starts recording as soon as a guest sits down with no 'Are you ready?' prompt to prevent clamming up. He keeps the room cool and lights pointed up to avoid a spotlight feel. He reads everything about the guest to build a mental model but never sends questions in advance, because that leads to rehearsed conversations; if a guest demands questions, he'd rather skip the interview. These touches make the conversation feel real and human. [13:51](https://addtry.com/d1728182-04b3-4aba-b1ef-c30df2051f8a?t=831000) ## Key moments - **[0:00] CPQ Hell** - [0:00] Joubin Mirzadegan: 'Salesforce CPQ to create a quote, get it approved, is horrific' - [0:52] LLMs can abstract away CPQ complexity similar to coding and legal use cases, says Joubin Mirzadegan - **[1:24] Zuck Interview** - [1:51] Swyx: 'If Priscilla Chan gets half of what she wants done, she will have more impact on humanity than Mark Zuckerberg' - [2:11] Swyx wasn't nervous interviewing Mark Zuckerberg thanks to extensive prep by CZI team - [2:59] Swyx reflects on Latent Space's journey from independent creator to top-tier AI podcast - [3:30] Swyx praises Joubin's podcast Grit for getting real founder stories - [3:48] Joubin Mirzadegan shifted Grit from CROs to founders because founders can speak more freely - [4:52] Swyx recommends Joubin's raw interview with Coinbase's Emily Choi on politics - **[5:08] Podcast Origins** - [5:24] Joubin Mirzadegan: 'The minute I stop looking forward to sitting down with someone, the show should be over' - [5:36] Joubin Mirzadegan had to justify buying a Roadcaster to Kleiner Perkins early in his podcasting - [6:01] Joubin Mirzadegan grew Palo Alto Networks' public cloud business from zero in central US before joining Kleiner Perkins - [6:35] Joubin Mirzadegan initially thought venture capital was a later-career move - [7:02] Working with Arvind Jain at Glean made Joubin realize he needed a CRO podcast to build his network - [8:07] The genesis of Joubin's Grit podcast: an excuse to meet CROs and help founders hire - **[15:44] Glean** - [15:45] Q: How did Glean overcome the dead category of enterprise search to become a successful AI company? - [16:05] Enterprise search was the 'eye roll of the industry' for decades until Glean, says Joubin - [17:53] Glean had to overcome skepticism, permissioning complexity, and deployment hurdles in its early days - [18:55] Arvind Jain built Glean using Rubrik as the core design partner, giving early credibility - [19:39] Glean's early success relied on a co-development design partner model, says Joubin - [20:17] Selling enterprise AI is like passing a bill through Congress, requiring multi-stakeholder alignment - **[22:56] Windsurf** - [22:59] Joubin Mirzadegan's career priority stack: people, people, market, product, money - [23:26] Q: How did Windsurf's go-to-market succeed and what was Joubin's role in sales training? - [23:56] Joubin Mirzadegan's KP charter: help technical founders with sales, hiring, and demand generation - [24:22] Kleiner Perkins invests in technical founders who often lack sales experience, so Joubin helps fill that gap - [25:51] Windsurf's Varun is an amazing engineer but needed help building a sales machine, says Joubin - [26:09] Swyx praises Windsurf's sales machine as one of the best he's seen in coding companies - **[38:39] Roadrunner** - [38:39] Joubin Mirzadegan unveils Roadrunner, a new KP incubation rebuilding CPQ from the ground up - [39:01] Joubin Mirzadegan's frustration with Salesforce CPQ's loading screens inspired Roadrunner - [39:45] Modern pricing models with consumption, bundles, and SKU sprawl broke legacy CPQ data models - [41:04] AI will force all pricing models toward consumption-based billing, says Joubin, compounding CPQ complexity - [42:04] In CIO dinners, CPQ was unanimously the number one pain point across companies like Uber and Box - [43:23] GPT 3.5 convinced Joubin Mirzadegan that LLMs could abstract CPQ complexity, leading to Roadrunner - **[59:36] High Performance** - [59:37] Q: What is Joubin's philosophy on high performance and personal habits? - [59:53] Joubin Mirzadegan works out every day without fail, reducing cognitive load on deciding when to exercise - [1:00:34] Joubin eats salad for lunch every day to eliminate decision fatigue and simplify his routine - [1:01:11] Swyx echoes Tim Urban: 'It's much easier to do something 100% of the time than 90% of the time' - [1:01:43] Swyx wonders why VCs don't enforce founder health and fitness like HFZero or Cognition's optimized environments - [1:02:37] Joubin Mirzadegan describes a founder's time demands as a pie-eating contest where the prize is more pie - **[1:06:26] Grit Defined** - [1:06:32] Joubin's podcast Grit is named after Angela Duckworth's definition: passion plus perseverance - [1:07:34] Joubin Mirzadegan: caring deeply makes work feel like play and enables out-sustaining others - [1:08:39] Swyx's dream guest for Latent Space is Andrej Karpathy, a long-time mentor and inspiration ## Speakers - **Swyx** (host) - **Joubin Mirzadegan** (guest) ## Topics Enterprise, Startups ## Mentioned Glean (company), Kleiner Perkins (company), Roadrunner (company), Salesforce (company), Windsurf (company), GPT-3.5 (product), Grit (product), Salesforce CPQ (product) ## Transcript ### CPQ Hell **Joubin Mirzadegan** [0:00] During my sales career, probably the number one thing that used to break my back was that the underlying software with like, uh, Salesforce CPQ and others just to like create a quote, get it approved, is horrific. Like, you think- if you think you've seen bad software, you haven't until you've seen a 30-second loading screen to get from one page to another when you're trying to close a deal with like two days left in the quarter. This is just like standard across the industry. This is how it worked at every job that I was ever at. I used to get yelled at because I would like be asking people to like turn something within a day or two because I needed to get a quote out the door. I was like, "Oh my God." I actually think you can abstract away a bunch of the complexity with these LLMs, and it's, you know, a unstructured and structured text that you can reason with and do stuff with, right? Like, that's why coding is such a great use case. That's why Harvey is such a great use case because you have like all this case law, and then you can point the LLM at it and you can reason with it, then you build a bunch of enterprise features and functionality and workflows on top of that. This is a very similar problem in nature. And so that was like the light bulb moment of like, okay, I think we can actually build something better. I feel good. I feel comfortable in this seat. Uh- **Swyx** [1:20] How's my levels? **Joubin Mirzadegan** [1:21] What's that? **Swyx** [1:22] How's my levels? **Joubin Mirzadegan** [1:22] Yeah, you're good. **Swyx** [1:23] All right. **Joubin Mirzadegan** [1:24] Um, ### Zuck Interview **Joubin Mirzadegan** [1:26] I gotta ask you, how was the, how was the Zuck interview? **Swyx** [1:31] Yeah, it's very interesting. Are we recording? **Joubin Mirzadegan** [1:33] Yeah, yeah, just rolling. **Swyx** [1:33] Yeah, yeah. Um, I think they kind of obviously had an, an agenda coming in, which was basically to raise the profile of CZI and Priscilla Chan, with Zuck being supporting character, right? And I think they accomplished their mission, uh, because, you know- **Joubin Mirzadegan** [1:51] Okay **Swyx** [1:51] ... my, my quick hot take in, in a single sentence is, if Priscilla Chan gets half of what she wants t- to do done, she will have more impact on humanity than Mark Zuckerberg, right? The- **Joubin Mirzadegan** [2:02] Yeah **Swyx** [2:02] ... Facebook will just be a funding mechanism for the greatest bio research work done in human history. **Joubin Mirzadegan** [2:08] Wow. Were you nervous? You must've been nervous. **Swyx** [2:11] No. Uh, I, I wasn't nervous because- **Joubin Mirzadegan** [2:13] Come on **Swyx** [2:13] ... of the sheer amount of prep that the CZI people put into us, which there's like, honestly, like low-key, to understand what it's like with the executive staff of a hundred billionaire, I've never dealt with someone like that. **Joubin Mirzadegan** [2:26] Yeah. **Swyx** [2:27] They are so good. They, they like, they prepped us so well so, so that like I felt like I knew exactly- **Joubin Mirzadegan** [2:34] You mean Zuck's team isn't randomly letting people walk in off the street and just ask whatever without any pre-base, pre-basing knowledge? **Swyx** [2:41] I've had to like interview three times to get even in that room. So yeah, it was, it was very, it was very fascinating. Uh, we were very honored to be picked by them because we're not a bio-focused podcast. **Joubin Mirzadegan** [2:50] No. **Swyx** [2:50] But the whole point was to reach out to engineers, and what they're, they're aware on the stronger footing. **Joubin Mirzadegan** [2:54] Yeah. That's awesome, man. I mean, it feels like a breakthrough, doesn't it? You've had some studs on. **Swyx** [2:59] Yeah. Uh, we just had Fei-Fei Li today. Uh, the- **Joubin Mirzadegan** [3:01] Today? **Swyx** [3:01] ... just re- yeah, just, just released. **Joubin Mirzadegan** [3:03] From, from, from... You came from that? **Swyx** [3:04] Well, Labs. Uh, no, I think we just released it. **Joubin Mirzadegan** [3:06] Oh, you did. **Swyx** [3:06] So that was- **Joubin Mirzadegan** [3:07] Oh, nice **Swyx** [3:07] ... it was a couple weeks ago. **Joubin Mirzadegan** [3:08] Who else have you done? **Swyx** [3:09] There's a bunch. Greg Brockman. **Joubin Mirzadegan** [3:10] You've done- **Swyx** [3:11] With AI **Joubin Mirzadegan** [3:11] ... you've done some amazing people. Is it surreal? **Swyx** [3:13] Yeah. It's, it's surreal for me, who started out as just like an independent creator, let's see where this goes, to now we're legitima- leg- legitimately in that tier of podcast that gets invited to everything. So that is very surreal. **Joubin Mirzadegan** [3:25] Yeah. It's pretty exciting. Who would've thought, you know? **Swyx** [3:30] I mean, I think like for you, I've been following your progress for a while. I don't think when you were still like a CRO podcast, I don't think I, I was caught, caught on yet, but I think like anyone following top founders who really wants to get real stories, they e- eventually find their way to you, and you get really good stuff, so congrats. **Joubin Mirzadegan** [3:48] I appreciate that. I, um, I think the, the transition from the CRO to the founder, whatever happened to like what episode seventy or eighty when I was like... 'Cause it was only CROs for a while. The thing that I found refreshing, I'm curious if, if you've seen this, is that founders and CEOs have an authority to speak in a different way than somebody on the executive team. **Swyx** [4:13] Yeah. **Joubin Mirzadegan** [4:13] Where they can just talk. **Swyx** [4:15] Yeah. **Joubin Mirzadegan** [4:15] And so much of what I wanna do is have like an earnest and honest conversation. **Swyx** [4:20] Yeah. **Joubin Mirzadegan** [4:20] And it's harder to do that when you're thinking, "What is my boss gonna think?" **Swyx** [4:24] Yeah. **Joubin Mirzadegan** [4:24] Whereas if you're the founder, you can just speak. **Swyx** [4:26] It's cleared by comms. **Joubin Mirzadegan** [4:27] You can, you can just speak, you know? **Swyx** [4:30] Yeah, I think y- yes, and it's also nice for distribution because obviously that's the more famous or public-facing person, so people do want to tune in. So you probably caught my attention for one of those episodes. I don't even, I don't even re- remember which. But um, you know, you've had so many. And even the non-CEOs, I think I would highlight for listeners, uh, your Emily Choi episode with, with, uh, from Coinbase. **Joubin Mirzadegan** [4:52] Yeah. **Swyx** [4:53] Um, yeah, it's like so raw and so like you, you went there with all the politics questions, you know? **Joubin Mirzadegan** [4:59] Yeah, the first one. Yeah, yeah, yeah, yeah. Yeah. I, I did. I, I, um, I appreciate it, man. It's, uh, as you know, it's a labor of love. **Swyx** [5:08] Mm-hmm. ### Podcast Origins **Joubin Mirzadegan** [5:08] Doing anything every week for six years. **Swyx** [5:12] Yeah. **Joubin Mirzadegan** [5:12] I mean, I guess it started every other week, and then it became every week after the s- transition from chief revenue officers to, to- **Swyx** [5:18] CEOs **Joubin Mirzadegan** [5:19] ... yeah, exactly. Doing anything for that long- ... every week, you better enjoy it. **Swyx** [5:24] Yeah. **Joubin Mirzadegan** [5:24] You know? Like I've always told myself, the minute I stop looking forward to sitting down with someone and talking to them is probably the minute the show should be over. **Swyx** [5:34] Well, it hasn't happened yet. **Joubin Mirzadegan** [5:35] Hasn't happened yet. **Swyx** [5:36] I was talking with Ali, uh, one of your partners, and they said they-- you even had to justify your purchase of a Roadcaster just to support your work. Doesn't Kleiner see the value in this, like... **Joubin Mirzadegan** [5:47] So in the early days when I, um, when I joined Kleiner Perkins, uh, I was quite young. **Swyx** [5:53] Yeah. **Joubin Mirzadegan** [5:54] And, uh, I was definitely figuring out like what is going on in venture. **Swyx** [6:00] And can you say a little bit what you did before? **Joubin Mirzadegan** [6:01] Yeah. I, I grew up in startups and then, uh, in sales and then- Had a great run. Those startups ultimately ended up getting acquired, the last one by Palo Alto Networks, which is like a big cybersecurity company. They asked me to move to, uh, the central US and build out their public cloud business in the central US. Took that business from zero to, uh, quite a bit in a short period of time. Kleiner heard about the work that I was doing, and then got in touch to see if there was an opportunity for me to kinda work with founders on once you've built the product, like, what do you do? **Swyx** [6:35] Yeah. **Joubin Mirzadegan** [6:35] Right? And I remember thinking at the time, like, no way. Like, venture, like venture sounds amazing, but like isn't that the job that I'm supposed to do, like, at the end of my career? **Swyx** [6:45] When you're retired, yeah. **Joubin Mirzadegan** [6:46] You know? Like, this sounds incredible, but like maybe later on. So anyway, we got to talking and it was, um, it was, uh... It became very obvious, like, there was a unique opportunity here. Fast-forward, one of the things that, um, that ended up happening was, uh, I was working really closely with Arvind at Glean. **Swyx** [7:02] Mm-hmm. **Joubin Mirzadegan** [7:03] It's actually the last incubation that we've done here, and Arvind is maybe the most genius product and technical mind that I've ever worked with. He definitely... I would say go-to-market is not native to him, and so he and I were doing a lot of work together to figure out, like, all right, we've built this incredible Glean product. At the time it was called Sio or Sio. I still don't know how to r- I still don't know how to pronounce it. And we were running all these routes together of like, "I think you should do this. I think you should do this," and then eventually it became very clear to me that we actually need somebody to run the routes, okay? Because, like, I couldn't do it and he couldn't do it. And so long story short, I started figuring out, well, like, what leaders do I know? What sales leaders do I know? And for me, I didn't know that many relative to a bunch of other people that were doing the job that I was doing, who've been in the industry for 30 years, who are at the tail end of their career, who do have this, like, coaching tree of leaders. And so I couldn't really help him hire somebody, and I realized then that I needed an excuse to get to know people that I do not know today. **Swyx** [8:07] Mm. **Joubin Mirzadegan** [8:07] And so that was the genesis, was like, how do I figure out a creative way to get to know these chief revenue officers and help them tell their story? You know, like, KP was like, "Uh, you know, uh, maybe. Uh, prove it." **Swyx** [8:23] They came to you, you came to them? They came to you. **Joubin Mirzadegan** [8:25] Who? **Swyx** [8:26] KP. **Joubin Mirzadegan** [8:26] Oh, no. I went to KP and I was like, "I think we should start- **Swyx** [8:29] Ah **Joubin Mirzadegan** [8:29] ... a podcast, uh, that interviews CROs." And they were like... I mean, it was... Skepticism would be generous. It was, uh, it was, uh, you know, we don't do a lot of talking as a firm. We l- generally let our portfolio and our founders, uh, speak on our behalf. Uh, and so, you know, there's definitely, like, other venture podcasts. Most of them are, like, pretty cringe, if I'm being honest. KP was skeptical and I kinda realized I also didn't do a very good job articulating what I thought it could be, so I recorded an episode anyway with my old boss at the time, and I sent it to some of my partners here and I just said, "Hey, this is what it would sound like. If you're interested and I still have a job here, like, let me know. This is what it would sound like." And they were like, "Oh, this is actually better than we thought." Like, they had to feel it. You know, it's like a, a product that they had to actually feel. **Swyx** [9:14] Mm-hmm. **Joubin Mirzadegan** [9:15] To Ali's point, we were like, "All right. Let's just do 10 and see how it goes." And then after 10 we were like, "Oh, this is actually, like, kinda working. I'm getting to know these CROs. It's getting easier to get to know them." And then I made a commitment to myself that I was gonna get to 100. Like, I just told myself, like, I will not make a judgment on what this is or isn't until we get to 100. **Swyx** [9:34] Yeah, it's the same... It's r- really weird that this number also appears when Marques Brownlee talks about how to start being a YouTuber, because you just don't know what you are until you just give yourself the room to experiment. **Joubin Mirzadegan** [9:46] My observation is that, I don't know if you feel this way, but, like, it's a very vulnerable feeling. Like, uh, even if you're the one asking the questions, not answering the questions- **Swyx** [9:56] Yeah **Joubin Mirzadegan** [9:56] ... you're really, like, out there. You feel very exposed. **Swyx** [9:59] Yeah. **Joubin Mirzadegan** [9:59] And the comments are a vicious place. And so, I don't know, for me, I was like, all right, until you get to 100, you don't really know what the quality of the work is and you kind of are making a pre-commitment that you're gonna tune out the noise, 'cause otherwise you start overreacting to what any single person thinks about any given episode. And then usually, I think that's why most podcasts m- you know, don't make it past five episodes- ... is because people start to be like, "Oh, maybe it's not good." Like, they start reacting, right? Uh, each of these slights feels more real, and so that's why I made the... Yeah, that's why I decided to do it. **Swyx** [10:38] Yeah. Uh, you started audio only, right? So you didn't... Well, then the beauty of podcast is nobody can talk back in the comments, 'cause there are no comments. I guess- **Joubin Mirzadegan** [10:46] With audio **Swyx** [10:47] ... iTunes reviews or- **Joubin Mirzadegan** [10:48] With audio. **Swyx** [10:48] Right, right, right. **Joubin Mirzadegan** [10:49] Yeah. Yeah, it was audio only. It was e- actually easier when it was audio only- **Swyx** [10:53] Yeah **Joubin Mirzadegan** [10:54] ... in many ways. **Swyx** [10:54] And now everyone has to be video. **Joubin Mirzadegan** [10:56] Actually, I think the core reason why we wanted to do video was it became very obvious, like for me, I listen to more podcasts than most. Like, I'm quite voracious about- **Swyx** [11:07] Same **Joubin Mirzadegan** [11:07] ... listening to podcasts, and I realized my behavior changed once I got YouTube Premium, where if you turn your phone off, you know- **Swyx** [11:18] Background **Joubin Mirzadegan** [11:18] ... off or whatever- **Swyx** [11:18] Yeah **Joubin Mirzadegan** [11:18] ... it's just ba- it's just noise. And then when you turn it back on, you, you flip the home screen up, it's video. **Swyx** [11:23] Yeah. **Joubin Mirzadegan** [11:24] And so I kinda wanted the multimodality where, for example, if I'm cooking, you know, it's, the video's open, or if take a shower, the video's open. And then, you know, if I'm on a run or something, I just click it off and then it's just the audio. It was, I think, more, more and more obvious to us then, I think quite clear now, I suspect you'd agree, that, uh, that y- you need both. **Swyx** [11:46] You do need both. I think the question is, can you do... Can you just transition to video without any change in the format whatsoever? And I think that has difficulties for me. I notice anecdotally that... So, so for example, there's a couple things, right? One, well, we are a technical podcast, so we can show code, we can show diagrams, we show ... demos of, of the product. And so, like, do we, do we spend the editor effort and money to put that into the video on the off chance that, like, the 5% of our audience watching on YouTube actually sees it? I don't know. It's not, it's not, like, super clear. The other more relevant thing is when you look at people like All-In, uh, or DoorDash, they start video and then they went audio or, you know, like, it's kind of like a video first mentality. Uh, and I feel like somehow when you start video first, it translates better to audio than the other way around. **Joubin Mirzadegan** [12:37] My only knock on video is that it's default more produced. **Swyx** [12:42] Yeah. **Joubin Mirzadegan** [12:42] And so much of what I wanna do is just have a conversation, and the minute that you have cameras everywhere with lights all over the place illuminating something, it feels more noticeable to the guest. Do you know what I mean? Like, it just feels more produced, therefore they start to imagine themselves as they're like- **Swyx** [13:02] They're on TV. **Joubin Mirzadegan** [13:03] Yeah. **Swyx** [13:03] They're- **Joubin Mirzadegan** [13:03] "Here's what I want to sound like when I'm on a podcast," as opposed to, "Here's what I just sound like." **Swyx** [13:09] Yeah. **Joubin Mirzadegan** [13:09] You know? And I think as soon as you see cameras and you just start acting differently. It's like, well, this is not how you are in real life. Like, what? You know? It's just a different thing, and so that's my one knock on the, on the video format. **Swyx** [13:20] Yeah. I noticed, you know, you, you also did the thing to me where you just start the conversation, right? You don't have a, "Well, here's the intro, here's the birth story, here's the origin story," uh, which I try to do sequentially a little bit, but y- that's one of your tricks, right? Which- **Joubin Mirzadegan** [13:33] Well, I would say I go through an extreme level of detail to make sure that the guest feels very comfortable when they sit down. So one example of that is, you know how you're greeted at the door, water, all those things. The second is recording just starts. There is no like, "Okay, are you ready?" 'Cause the minute that somebody says like, "Okay, are you ready? Go," you clam up. You're like, "Okay, I'm gonna be the- **Swyx** [14:00] That's it **Joubin Mirzadegan** [14:01] ... guest that I wanna be." It's like, you know, when you're sleeping at night before you go onto a podcast, you're like, "Okay, how am I gonna sound? What am I gonna say that's gonna make me feel smart?" You know what I mean? Make me sound smart. **Swyx** [14:11] Yeah, yeah. **Joubin Mirzadegan** [14:11] And so you start to build this, like, idealized version of yourself that you wanna project to the world- **Swyx** [14:17] Yeah **Joubin Mirzadegan** [14:17] ... which is, like, not real. And so start talking as soon as you sit down. The temperature of the room, like I like the temperature to be cold. I don't want people to feel like they're sweating or hot. Feels, like, kinda cool in here, right? Uh, the way that the lights are, you'll notice the lights are all up, not down. **Swyx** [14:31] Mm-hmm. **Joubin Mirzadegan** [14:32] Like, I, I think- **Swyx** [14:32] 'Cause it bounces off. **Joubin Mirzadegan** [14:33] Yeah, I think it's important to not make it feel spotlighty- **Swyx** [14:36] Yeah **Joubin Mirzadegan** [14:36] ... if that makes sense. **Swyx** [14:37] Yeah. **Joubin Mirzadegan** [14:37] Um, the way that I do prep, and then, and then for the guest prep, like for example, I will have read everything about them, right? And so I'll build basically my own mental model of who I think they are, and then I'll spend the conversation kind of poking at that mental model, and then I never give the guest the questions. Because if you give the guest the questions, well, all of a sudden it's like a rehearsed set of conversations, which is not how real life goes. **Swyx** [15:02] Mm-hmm. **Joubin Mirzadegan** [15:02] And so, like, I go through, I guess, kind of a lot to make sure that it feels real. **Swyx** [15:08] Yeah. It's funny 'cause like I- we get asked a lot for questions up front. Uh, for example, the Zuck pod was very, very, very well prepped and, and screened. Sometimes you just don't get to get the interview if you don't do that. **Joubin Mirzadegan** [15:19] I won't do it. **Swyx** [15:19] Yeah. **Joubin Mirzadegan** [15:20] I just won't do the interview. **Swyx** [15:21] Yeah. We're, we're more flexible there. Um, and I, I guess- **Joubin Mirzadegan** [15:24] Okay, if I had Zuck... Okay, if I was like- ... if, if, if you told me, "Joubin, you can have Zuck, but he has to see the questions before," I'd probably- **Swyx** [15:31] Because, like, look, the, the secret is the PR team's gonna screen the questions, but you can go off script. **Joubin Mirzadegan** [15:36] Yeah. **Swyx** [15:36] You can ask follow-up questions. **Joubin Mirzadegan** [15:37] Yeah. **Swyx** [15:38] So it- it's really not that bad. **Joubin Mirzadegan** [15:39] That's true. **Swyx** [15:40] It's really not that bad. That was Creator Corner. I, I do wanna obviously get you on the sort of professional side. ### Glean **Joubin Mirzadegan** [15:44] Yeah. Yeah. **Swyx** [15:45] But obviously I, I love to indulge in Creator Corner. Coming back to Glean, Glean is obviously KP's most recent incubation and success, and it's, it's gone, it's done super well. What's something that you realize working with Arvind that made you understand, well, here's what works in applying AI to the enterprise or whatever, like selling AI to enterprise? **Joubin Mirzadegan** [16:05] Yeah. I think, um, at the time, in the early days of Glean, it... When Arvind came to Mamoon, this pitch of doing enterprise search was like the eye roll of the industry, meaning, like, if you ask any chief information officer, if you ask any venture capitalist, they've been hearing that same pitch for a couple of decades now- **Swyx** [16:31] Yeah **Joubin Mirzadegan** [16:31] ... where everybody has promised, Google included, like the best companies in the world, that they're gonna solve enterprise search once and for all. And so, um, you know, I give Mamoon a bunch of credit because he realized that if this problem is gonna be solved once and for all, it's probably gonna be somebody like Arvind that can do it. On the technology side, like AI, this was, whatever, 2019, 20- 2018, 2019. This was not like... LLMs had not been birthed yet, right? And so I think in the beginning, like, it was a pretty serious slog with Glean because you're asking these systems to basically crawl through an organization's entire corpus of data, do it with all of the permissioning, do it with, uh, all of the auth, like this multi-layered cake of protections to make sure that I never see what I'm never supposed to see, right? Like, I never see Swix's, you know, like comp data, for example. And so getting that right is, like, insanely hard. Then let's just assume, which in Glean's case they did, that you get the technology right. Then you have to figure out how do you get past the, like, eye roll of all the people that are, like, just default skeptical. **Swyx** [17:51] Yeah, like the category's just dead to them. **Joubin Mirzadegan** [17:53] The category's completely dead to them. **Swyx** [17:54] Yeah. **Joubin Mirzadegan** [17:55] Then you gotta figure out, like, how do you deploy that, right? Do you deploy it on their premise? Do you deploy it in the cloud? **Swyx** [18:02] Sure. **Joubin Mirzadegan** [18:02] All the security. Then you gotta go through an insane amount of hoops because this is, like, pretty sensitive information- ... that you're indexing, so you gotta go through all of that. I would say The thing about Glean is now it's become one of the, like, obviously great AI companies that's, like, in the heart of the hurricane. Back then, it was, like, extremely unobvious. Like, extremely unobvious. **Swyx** [18:30] So, so let, let's... I wanna double-click on that and then, uh, because I feel like we just did the b- the breadth of the problem, but let's talk about getting past the category is dead, um, sort of default rejection. **Joubin Mirzadegan** [18:43] Yeah. **Swyx** [18:44] So what do you do there? What do you, what do you learn? **Joubin Mirzadegan** [18:47] Yeah, I mean- **Swyx** [18:47] What did you try and didn't work? **Joubin Mirzadegan** [18:48] The advantage that Arvind had was that he was previously the co-founder of Rubrik. **Swyx** [18:54] Yeah. **Joubin Mirzadegan** [18:55] So he noticed this problem at Rubrik, left Rubrik to start Glean, and he basically built Glean for Rubrik, right? And the bet that he was gonna make was, like, rough and tumble what Rubrik wanted is probably what the rest of the world was gonna want. So it was like their core design partner. So I think, like, he had access to all the right people. He knew all of the systems. That was, like, really important, like, having these early, early believers that are willing to basically co-develop this solution with you, that you have, like, unfettered access to get things done. It was still an insane effort to do it, but I think it made it a lot easier, and that way at least you can show, "Hey, this is, like, working in production for somebody." **Swyx** [19:39] Yeah. **Joubin Mirzadegan** [19:39] Right? I'll pause there. Does that make sense? **Swyx** [19:41] Yeah, it's a design partner process. **Joubin Mirzadegan** [19:43] Yeah. **Swyx** [19:43] So I think it's a pretty common go-to-market for early-stage, uh, enterprise, I guess. **Joubin Mirzadegan** [19:48] Right? Like, that's your ability to communicate what have you built, and then how do you get that through an organization? It's like, um, it's like passing a bill through Congress, right? Like, you, you have this thing, Glean, and you gotta get all of these stakeholders inside a customer aligned, get 'em all up to speed on, like, what's in the bill, like the product, make sure everybody else, like, you're helping them manage their own process and organization, right? It's no joke. It is no joke. I don't think people realize how hard it was back then. **Swyx** [20:22] I, I think it still is very hard, you know. And it's-- What's, what, what's weird is you have a special expertise. I think, I think the engineers that are listening maybe don't have the appreciation of the work that this, this, this involves. It is a little bit of almost like a military mapping of the organization that you have to sort of understand who your champions are and who the, where the resistance is and how you want to sort of prosecute a campaign to go to market, I guess, in, in a, in a very, very targeted way. **Joubin Mirzadegan** [20:53] I think if you're an engineer, it's even harder now than it used to be, and the reason for that is this technology is so new for organizations that they both have to figure out, "How do I use LLMs and AI within my own org?" and, "How do I use your product within that ecosystem?" **Swyx** [21:11] Yeah. **Joubin Mirzadegan** [21:12] Right? So, like, they're first trying to figure out, "How do I use the, like, underlying sand that's changing underneath it?" And then, "How do I use your product on top of, like, quicksand?" Right? That's, like, a really hard problem, which is why you see so many companies doing, like, this forward deployed engineer motion where what they're going in and doing is saying, "Okay, number one, like, here's how we think about LLMs and where you can get best use of it. Number two, here is this engineer that we're gonna forward deploy into your environment, that we're gonna, like, basically, like, co-develop this solution custom fit- **Swyx** [21:44] Yeah **Joubin Mirzadegan** [21:44] ... for this org." So you have to do, like, a lot of hand-holding, and the reason is because, like, we're just so early to AI right now that, like, of course you have to do a lot of hand-holding. Like, of course you have to, like, surround these customers with a bunch of technical resources to, like, make it successful. **Swyx** [22:01] Yeah. **Joubin Mirzadegan** [22:02] Are there regrets, like buckets of regrets that you have? **Swyx** [22:04] There's also, like, the, did you spend your life working on things that you think are, you care about? That you're like, yeah, I mean, you know, even if the finances didn't super work out, I'm still happy I worked on it. If I did not like the mission or the job or, like, the people I worked with, that would be a bigger regret than the, than the pure finance side. **Joubin Mirzadegan** [22:26] Mm. **Swyx** [22:26] Obviously, finance does matter. I always think about it as like, well, in, in terms of ranking, you should probably put people, products, and money in, in sort of roughly that order. **Joubin Mirzadegan** [22:35] If you're evaluating a company? **Swyx** [22:36] Yeah, as an employee, obviously, if you've, if you start something. **Joubin Mirzadegan** [22:40] People, product, money. Okay. **Swyx** [22:42] 'Cause product is easier to shift than people, and then the money, um, if, if the first two don't really work, then no- basically no amount of money will really make up for it. **Joubin Mirzadegan** [22:54] Yeah, okay. **Swyx** [22:55] Right. **Joubin Mirzadegan** [22:55] I can buy that stack rank. ### Windsurf **Swyx** [22:56] Yeah. **Joubin Mirzadegan** [22:57] I would maybe re-swizzle it a little bit, but I could buy that. **Swyx** [22:59] Yeah. **Joubin Mirzadegan** [22:59] Like, maybe I would say, like, people, and then I would double people. Like, I would probably add it again. **Swyx** [23:06] Sure. **Joubin Mirzadegan** [23:06] Uh, and then maybe market, product, money. **Swyx** [23:10] Yeah. Market's really good. Well, I guess, you know, I, I maybe bundle market with product- **Joubin Mirzadegan** [23:14] Product, yeah **Swyx** [23:14] ... or, or just assume that market is given, given I o- only work in dev tools. But, um, yeah, that's, that's, that's important distinction. Coming back to you, or just, this is general learnings from KP before we go into Roadrunner. Yeah, I just wanted to also touch on the other conversation that you had with Varun from Windsurf, which I also, I really enjoyed. Shout out to him. He's gonna listen obviously. Um- **Joubin Mirzadegan** [23:34] Love that guy **Swyx** [23:35] ... another interesting company that I was finding parallels to Glean in a sense that kind of you have to just get people to hand over their entire code base. Um, and a, a very tough go to market. I've heard from multiple Windsurf folks that you went there and did, like, sales training, cheerleader sessions. What is it you do? **Joubin Mirzadegan** [23:56] At Windsurf or in general at KP? **Swyx** [23:58] You use, use Windsurf as an example, but use that to tell the story of what you- **Joubin Mirzadegan** [24:01] Of KP? **Swyx** [24:02] Of, yeah. **Joubin Mirzadegan** [24:03] When I joined six years ago, my charter was kinda twofold at KP. Number one was, "Hey, we have this group of CIOs and customer networks. Can you help us manage it?" Right? Number two was, "Hey, our founders Need a lot of help on sales and distribution. Where you can, can you help them there? **Swyx** [24:23] Mm-hmm. **Joubin Mirzadegan** [24:24] That was, like, the core charter, right? Then I realized that in order to help founders with go-to-market, like, we needed to help them hire. So that was the excuse for the podcast, right? It was like, "All right. I need an excuse to get to know these people so I can help these founders hire great CROs." Uh, then that all started to work and we were like, "Great, let's double down on helping founders with sales." So we hired somebody on my team, Liam. Then we were like, "Great, let's double down on helping folks like Varun get access to world-class customers." So we doubled down on that and hired, uh, hired somebody else. And we're like, "Great, let's help founders with building their demand gen funnels and a bunch of stuff on the marketing side." Okay, hired Suzanne. So that was kind of the first three years, was like, how do we... W- like, KP generally invests in technical founders. That's, like, I'd say a majority. Not all, but a lot. And those technical founders are generally exceptional at product and eng, and usually have never closed a deal before. Or usually have never created, like, a pop-up funnel, like, demand flow, right? And so we wanted to, as a firm, really help that muscle for KP founders, okay? Like, Varun is a great example. He's an amazing engineer. **Swyx** [25:51] Yeah. **Joubin Mirzadegan** [25:51] But, like, he's never had to actually build the machine that is sales and marketing go-to-market. **Swyx** [25:57] Yeah, yeah. So I, I think this is something that people don't appreciate about Windsurf, is that they look at the product and they understand, they understand it's a, you know, it's agentic IDE. But actually there's a sales machine that is one of the best I've ever seen. **Joubin Mirzadegan** [26:09] Yeah. **Swyx** [26:09] And you helped to build it, so I'm like, "Well, tell me more about it." **Joubin Mirzadegan** [26:13] I think, um- **Swyx** [26:14] And, and maybe we can quantify as well, right? I think, like, something like zero to 100 million ARR in seven months or something like that, eight months. **Joubin Mirzadegan** [26:22] It was the most torrential growth I think I've ever seen in a KP company. It was insane. **Swyx** [26:29] That's a high bar because- **Joubin Mirzadegan** [26:30] It was insane **Swyx** [26:32] ... you have some pretty good companies. **Joubin Mirzadegan** [26:33] It was insane. **Swyx** [26:34] Yeah, tell me more. **Joubin Mirzadegan** [26:34] We're seeing companies like Harvey and others doing, following a similar path, but like, I mean, you know better than anybody, like, uh, coding is an incredible use case for AI right now. **Swyx** [26:46] Right. But I don't expect, like, government, Fortune 500 to adopt at this, at this kind of rate, and that's why, and that's why I was seriously miscalibrated on. Like, I was with them, I, I did a podcast with them on the day of Windsurf's launch, and even then I was like, "Eh, I don't know. This seems like a cursed clone." **Joubin Mirzadegan** [27:02] I think what Windsurf got right was probably a couple things. The first was a commitment from the founders that they wanna both build Google-class product and Salesforce-class distribution. **Swyx** [27:15] Yes. **Joubin Mirzadegan** [27:16] Like, it was a true commitment from the beginning. **Swyx** [27:18] Okay. **Joubin Mirzadegan** [27:19] And most founders, okay, a lot of founders will say, "The product will sell itself. As long as we build a good enough product, people will come." **Swyx** [27:30] They'll come, they pay the $20 a month. **Joubin Mirzadegan** [27:31] Exactly. **Swyx** [27:32] And then they'll, they'll just love us so much, we'll-- they'll magically upgrade. **Joubin Mirzadegan** [27:34] Exactly, which usually doesn't work that way. So that was like, I think number one, was like a real commitment to doing it up front and knowing that if you can marry those two things, like, it's magic, okay? I think the second was that they were in a great market that was getting pulled. Generally speaking, the coding market still today is just getting dragged by the industry because it's such a good use case. Engineers are expensive. Having a copilot for them is, like, makes a lot of sense. The technology is there to be able to take the structured nature of code and reason with it to then produce outputs that are great for, for engineers. So, like, that was kinda number two. And then I think the third was probably just, like, they moved fast. They hired great and they hired fast. **Swyx** [28:21] Yeah. **Joubin Mirzadegan** [28:21] And- **Swyx** [28:21] Were, were you involved? Like Graham, Jeff? **Joubin Mirzadegan** [28:23] I would give more credit to Liam on my team, who was, like, intricately involved in building out that entire go-to-market. That team, I guess, is now at... **Swyx** [28:33] Cognition. **Joubin Mirzadegan** [28:34] At Cognition. **Swyx** [28:35] Yeah. **Joubin Mirzadegan** [28:35] So you've seen it firsthand. **Swyx** [28:36] Yeah. No, like it, it- **Joubin Mirzadegan** [28:38] It's no joke **Swyx** [28:39] ... this is why, like, I mean, I, I put it as far, as part of my, like, why Cognition thesis. Core Cognition, Devin Cognition is very good at product and eng, but they didn't really have that much of a sales team, and here's the most crack sales team I've seen in, in coding, at least in dev tools, and you just bring them together. Like the, the... Like, how hard can this be? Like, it's like a really good formula for success. **Joubin Mirzadegan** [29:02] Yeah. I don't wanna understate how serious Windsurf was- **Swyx** [29:07] Yeah **Joubin Mirzadegan** [29:08] ... about distribution, not just product. **Swyx** [29:11] Okay. **Joubin Mirzadegan** [29:12] The lesson that I take away from them is, like, they were as serious about building an incredible product as they were about building incredible sales and go-to-market. **Swyx** [29:22] Yeah. **Joubin Mirzadegan** [29:22] And it's easier said than done. **Swyx** [29:25] Yeah, you can't be serious about everything, and everything's the number one priority. **Joubin Mirzadegan** [29:29] That's right. That's right. **Swyx** [29:29] So what the hell? But they did, they, they, they pulled it off, uh, which is in- in- inc- impressive. Uh, the one anecdote I guess I'll share on the distribution side is they're the first company I've seen with, like, a real one floor of the, of it is just dedicated to their video production, uh, one, one floor of the sort of, uh, office down in Redwood City, and I've never seen that. I, I'm like, you know, you're a pretty young company. You're, you're mostly developer tools, but, like, here's, like, a whole studio set that you can do anything out of and make it interesting on video, and it's 'cause you really care about getting this across, you know, even though you're just selling software. **Joubin Mirzadegan** [30:02] Totally. **Swyx** [30:03] Like Gle- I'm sure Glean doesn't have it. I don't think I've seen a, a video from Glean that's not just a screen share. **Joubin Mirzadegan** [30:08] Totally. **Swyx** [30:09] Okay. G- give me one more thing on just, like, your... Like, how do you hire a sales team like this, right? We have founders listening. They're building interesting AI products. They don't really know how to go to market. Do you have to offer an arm and a leg to hire your first sales leader? Do you have to only work with Kleiner to, to do that? Like, what is the actual principle that you advise founders to follow? **Joubin Mirzadegan** [30:30] Uh, I'll give you some anti-patterns. The first is- Do not just go on their LinkedIn and look at all the fancy logos that they have gone and worked at and immediately assume that because they were at Snowflake or because they were at Databricks, they must be good for your AI company. It just doesn't work that way. In fact, in many cases, it's the inverse is true, where if you had to sell the number three product in a market and you had to fight tooth and nail and you were still successful there, you're probably, like, if you go to a great company, gonna have a much higher proclivity to do well, right? Whereas if you were, I don't know, if you joined Snowflake at 100 million of ARR, and you join, like, their enterprise team in the Bay Area, it's like, yeah, I get it, but, like, that's not that impressive. No offense to anybody that joined Snowflake at that time. There were some diamonds in the rough. So I think that's, that's one. **Swyx** [31:29] Well, well, it's, like, more like they're a fit for exactly that scenario if you're in that scenario. **Joubin Mirzadegan** [31:33] That's right. **Swyx** [31:34] But you're not. **Joubin Mirzadegan** [31:34] That's right. That's right. **Swyx** [31:35] You know? **Joubin Mirzadegan** [31:35] Especially for startups, right? The problem with that is that you have to actually interview them. Like - **Swyx** [31:42] Okay **Joubin Mirzadegan** [31:43] ... like, you can't just see what they did on their LinkedIn profile and know if they're good or not. Like, you have to, like, actually dig in, and even more, it's not necessarily all of the things that they have actually done- **Swyx** [31:56] Yes **Joubin Mirzadegan** [31:56] ... that make them good. **Swyx** [31:57] 'Cause you're hiring for potential. **Joubin Mirzadegan** [31:58] It's like all sorts of intangible things that you have to, like, feel, right? Like, all the same things that we would, you know, wanna feel with a founder, right? Like, do they have a chip on their shoulder? What are they motivated by? Is it money? Is it, you know, living in the shadow of their brother or sister? Is it that they grew up in, you know, a first-generation immigrant household? Whatever it is, right? **Swyx** [32:21] I see. So, so but you go really deep on the background. **Joubin Mirzadegan** [32:23] Really deep on understanding, hey, there's gonna be a million things that go wrong here. When they do, what is the driving force that's actually gonna push you over the hump? And especially in sales, like, you get told no way more than you get told yes. After you get told no enough times, internal, some, like, flame within needs to continue to burn to continue to push you, right? And hiring for that, like, this is why, like, every exec recruiter and everything is like they've got it so wrong in most cases 'cause they just go to the fanciest LinkedIn profile- **Swyx** [32:58] Right **Joubin Mirzadegan** [32:58] ... and are like, "Oh yeah, this person has, like, all of these great logos. This is the person that you should hire." I'll give you an anecdote. Inside the KP portfolio, okay, our top eight companies, let's take five exec roles across the top eight companies, companies like Rippling and Glean, okay? 38 out of 40 of those roles, okay, those executives report to the CEO for the first time in their career. **Swyx** [33:23] Mm. **Joubin Mirzadegan** [33:24] Okay? So what does that tell you? Like, well, generally, it's like their experience is not the thing . Like, it's the context that they've built. It's the trust that they have. It's their ability to, like, learn fast and grow with the company. It is not like what have you done at your last five companies. **Swyx** [33:44] Yeah. **Joubin Mirzadegan** [33:44] Does that make sense? **Swyx** [33:45] Yeah, it totally makes sense. Uh, i- it's very first principles thinking is the way that, uh, Scott Wu would put it. **Joubin Mirzadegan** [33:50] Yeah. So I'd say that's, like, probably one, um, one big failure mode. I think the other, especially in AI today, is that the bar for how technical you are is going up. It's just going up, default. **Swyx** [34:05] So, so salespeople have gotta be technical. **Joubin Mirzadegan** [34:07] Much more technical. **Swyx** [34:07] That's- **Joubin Mirzadegan** [34:07] Like, uh- **Swyx** [34:08] That's a tough one **Joubin Mirzadegan** [34:08] ... like more technical than they used to be. **Swyx** [34:10] Yeah. **Joubin Mirzadegan** [34:11] And what do I mean by technical? Like, you don't have to, in my opinion, understand, like, every intricacy of- **Swyx** [34:19] The transformer **Joubin Mirzadegan** [34:20] ... I don't know. The, like- **Swyx** [34:20] Yeah **Joubin Mirzadegan** [34:20] ... exactly, the transformer. But you should be able to go over to an engineer's desk and ask the right questions to get a depth of understanding that you can actually communicate and articulate effectively to a customer, right? And I think, like, that matters a lot. That matters a lot, and so, like, that bar has started to raise more and more for me, um, on, like, can you actually describe the product and what you do and how it fits into a broader ecosystem without relying on, like, some sales engineer to do it for you? **Swyx** [34:52] Yeah, but, like, in a, in a, in an interview, sometimes you just don't get that because you, that's what sales training is for. It's, like, people prep battle cards. They, they get time with the product. They take time with the founders. Then they get it, right? It's, it's hard to get that in the interview. **Joubin Mirzadegan** [35:07] Yeah, but it's, it's not hard to look at somebody's background and understand were they willing to do that. **Swyx** [35:13] Yeah, yeah. **Joubin Mirzadegan** [35:13] Did they actually want to do that? **Swyx** [35:15] It's, what's really funny is, well, one of my core memories as an engineer learning the, the, the, the ropes in startups was our new head of sales coming in at Netlify, which is a KP company, coming in saying, you know, I also was very stressed. I was like, "Well, you know, our competitors have these, these, these, these things. We need to match them and exceed them." And he's like, "Nope, that's engineering thinking. Like, give me anything. I'll sell it," you know? And I was like, "Wow, that's a good sales guy." But I think to some extent, s- sales guys, salespeople who can sell regardless of the product, that's the old school way kind of that where they just know how to do the steak dinners and golf things and whatever else they do, uh, to make their number versus now I think the, the rise of the more technical sales hire who really has to care actually about the product and explain and, and get, and get in the weeds with people. I think that that's, that's the shift that I'm seeing. **Joubin Mirzadegan** [36:07] I'll add one more thing that really, really matters. Have they worked at a company that is similar in size? **Swyx** [36:16] Yes. **Joubin Mirzadegan** [36:16] So for example, if you're a seed or Series A founder and you're evaluating sales leaders and AEs that have only been at companies that have done, like, 50 million or more of ARR when they joined- It's probably gonna be really difficult for them. And the reason for that is because they've had a brand their entire life, they've had inbound leads that just come to them, right? Uh, they, um, they generally can, like, lean on the credibility of the company to be able-- They've had a playbook that they just have to execute and run, right? So there's like all these things that make the feeling of being, call it like first sales leader, first AE, where you're way more of an artist- **Swyx** [36:59] Yeah **Joubin Mirzadegan** [36:59] ... than you are, like, a scientist. Like, it's not this medic-type playbook in the very beginning. And then when you get to, like, where Windsurf was or is now, it's, like, very systematized, right? Um, it is a machine. **Swyx** [37:12] So, so much. There's boot camps- **Joubin Mirzadegan** [37:14] It is a machine **Swyx** [37:14] ... there's battle cards. **Joubin Mirzadegan** [37:15] But in the early days, like, it is-- um, it's creative ways of getting something done. **Swyx** [37:22] Yeah. **Joubin Mirzadegan** [37:23] It's creative ways of getting something done, and it just looks more like art than it does in science. And so if you've never had to do that before, it's gonna feel quite foreign to you. **Swyx** [37:31] Yeah. It's, uh, it, it really is. Uh, but this is why, you know, people with more experience can, can come in and show the, show us the ropes. **Joubin Mirzadegan** [37:39] Like, by the way, I would not probably be a good, uh, salesperson at Windsurf today. I just probably-- like, I am not the person- **Swyx** [37:47] You're not, you're not deep enough in the product **Joubin Mirzadegan** [37:48] ... that's gonna, like, execute this, like, perfect playbook that was handed to me- **Swyx** [37:52] Right **Joubin Mirzadegan** [37:53] ... where I'm, like, qualifying criteria per letter of the playbook. You know, this is not my thing. You know? Um- **Swyx** [38:00] But y- I think you were-- you, you kind of made a good fractional sales leader, I would say. **Joubin Mirzadegan** [38:05] Yeah. **Swyx** [38:06] Because people still talk about you internally. Uh, I don't know what you did. You just, like- ... you just did, like, mo-motivational sessions or something? **Joubin Mirzadegan** [38:13] Uh, honestly, they did, they did most of the heavy lifting. I probably, like, went in there and did some, like, random rah-rah stuff. **Swyx** [38:20] Yeah. **Joubin Mirzadegan** [38:21] Uh, and then- **Swyx** [38:21] Which they need **Joubin Mirzadegan** [38:22] ... and then introduced Varun to a bunch of, a bunch of customers. But the KP team, my team, did a majority of the heavy lifting, and so I give Liam, Lauren, uh, Suzanne a bunch of credit for the work that they did there. **Swyx** [38:35] Yeah. Okay. So now we come around to your current thing. **Joubin Mirzadegan** [38:39] Mm. ### Roadrunner **Swyx** [38:39] Few months ago, I think two months ago, you, you sat down, you told me, "I'm working on a new thing, and it's, like, su-super stealth and secret, but it's gonna be the, you know, hottest new KP incubation since Glean." And I'm super interested in it. All I know is it leans on basically everything you've done- **Joubin Mirzadegan** [38:56] Yeah **Swyx** [38:56] ... you know, everything we talked about. But can you introduce Roadrunner and the thesis? **Joubin Mirzadegan** [39:01] I would say you're right. Like, during my sales career, probably the number one thing that used to break my back was that the underlying software with, like, uh, Salesforce CPQ and others, just to, like, create a quote, get it approved, is horrific. Like you think-- if you think you've seen bad software, you haven't until you've seen a 30-second loading screen to get from one page to another when you're trying to close a deal with, like, two days left in a quarter, okay? And this is just, this is just, like, standard across the industry. This is just how it works. It's how it worked at every job that I was ever at. I used to get yelled at because I would, like, be asking people to, like, turn something within a day or two because I needed to get a quote out the door. It happened when I was leading teams. They would always be getting yelled at because they were trying to move too fast for these systems to work, okay? And the reason the underlying systems do not work is basically pricing models went from a world where it's like, all right, Swix, like, you wanna get a Netflix account. You have, like, one seat, you, that maps to one person, okay? And then it's like ten ninety-nine a month. Very simple, right? Then you're like, "Okay, actually, I want a family plan." Okay, well, now you can add five people, no more than that, and it's like eight ninety-nine a month. That's, like, how pricing models have generally worked. In the B2B context, it's like, I wanna sell a thousand licenses of, you know, pick your product. LinkedIn, right? That maps to a thousand people at an organization, okay? What has happened is that we have now done, you know, like, companies have, like, 30 products more, 50 and 100 in some cases. Uh, those products scale by volume, and then there's discounts associated with them. Then you have to do renewals. Then you wanna do early renewals. Then you wanna do expansions. Then you wanna do them across, like, 15 different product lines, right? So the complexity has just started to, like, increase exponentially. Then you're like, "Actually, um, I wanna just-- I want the customer to pay as they go." That might be how you guys are using-- uh, how you guys are selling today. It's like, well, I actually just like, like, make sure they pay a minimum amount, and then anything above that, we'll just bill them, right? It's like how Databricks- **Swyx** [41:14] Very custom function. **Joubin Mirzadegan** [41:15] Exactly. Like, that's how a lot-- like, that's how Cursor and others are too. It's like amount of tokens that I consume, just pay, just bill me for that. So, like, these pricing models have gone bananas, okay? And by the way, this has barely even started, and the reason it's barely even started is, like, with AI, all of these pricing models are minimally gonna start to look like consumption-based pricing, right? That's, like, how you consume- **Swyx** [41:35] Because of tokens. **Joubin Mirzadegan** [41:36] Exactly. That's how you consume Anthropic, and that's how you con-consume OpenAI. **Swyx** [41:40] Yeah. **Joubin Mirzadegan** [41:41] And so the problem is about to get way worse, okay? And so it was a problem that I kind of, like, was feeling because I was like, oh, the underlying data model is just breaking because 20 years ago, Salesforce CPQ was not designed for, like, all of these permutations, right? **Swyx** [41:57] Yeah. **Joubin Mirzadegan** [41:57] It was like a static world where one person is a Netflix license. The most you could do is a family account, right? **Swyx** [42:03] Yeah. **Joubin Mirzadegan** [42:04] Okay, so that happened. Then I joined KP, and, um, uh, Lauren on my team and I started a group of tech CIOs, 35 tech CIOs, okay, companies like Uber and Box and others, okay, that meet twice a year. And this was, like, four years ago, so, like, pre-LLMs, pre-anything. Uh, I, um, I asked them, "What is the number one problem that you have in your company right now?" So I was at a dinner with, like, five CIOs. And they were like, uh, "CPQ." And I'm like, "No way." And they were like, "No, I'm not kidding you." They said, "We are getting yelled at by our chief revenue officers and salespeople all the time because the underlying software that we're delivering to them doesn't work." Fast-forward six months later, we have a second dinner, okay? Different group of CIOs in this, in this network, okay? So now I'm with five other CIOs. I ask them, "What's the number one problem you have in your company?" All of them said the exact same answer. And I was like, "Whoa." Like, that's pretty rare. Like, you just don't... Pain does not grow on trees like that. And so we as a firm got very excited because we were like, it's pretty rare and unique to have this many customers that have this bad and, of a kind of uniform pain. **Swyx** [43:22] Yeah. **Joubin Mirzadegan** [43:23] So we did a full market map. We were trying to invest in a company, didn't find anything compelling, okay? Just like could not find any great companies, okay? Um, then GPT 3.5 comes out, and I was like, "Oh my God, I actually think you can abstract away a bunch of the complexity with these LLMs, and it's, you know, a unstructured and structured text that you can reason with and do stuff with," right? Like, that's why coding is such a great use case. That's why Harvey is such a great use case, 'cause you have, like, all this case law, and then you can point the LLM at it and you can reason with it, then you build a bunch of enterprise features and functionality and workflows on top of that. This is a very similar problem in nature. And so that was like the light bulb moment of like, okay, I think we can actually build something better. Then I started asking myself, "Well, like, why is nobody... Like, why is nobody fixing this?" **Swyx** [44:18] No, no, no. No, so in those dinners- **Joubin Mirzadegan** [44:19] Yeah, yeah. Why is nobody fixing this? **Swyx** [44:20] Okay. All right, yeah. **Joubin Mirzadegan** [44:21] Right? Like, that's the question. Like, why has the incumbent, Salesforce anybody else, not fixed this? Why is this still an issue? Okay? The reason is because, um, all of these tools were basically built in a pre-LLM era. Their data models are broken because they did not see consumption and a million SKUs and the sprawl that comes with that coming. In order for them to basically build a product that handles all of the complexity and permutations, they'd have to rebuild their entire data model and architecture from the ground up, which is the same thing that basically most incumbents have to do today. **Swyx** [45:00] Mm-hmm. **Joubin Mirzadegan** [45:00] Right? Which is why there's, like, so much frenzy around early-stage startups in VC because in order for an incumbent to go do what an, like, a Harvey is doing, you have to literally rebuild that company from the ground up. Like, you have to build the entire architecture differently. Like, it reminds me when I was in the public cloud, like, my career was in the public cloud before this. In the very early days, everybody was moving from on-prem to AWS, okay? And initially, everybody was like, "Great, we'll just lift and shift our application and just throw it into the public cloud." And all of a sudden you realize, like, oh no, like S3 buck- S3 buckets can just, like, disappear, right? So like, no, well, you actually have to rebuild this stack cloud native from the ground up. That's like the same thing that's happening in, in, in AI today. And so that's like the classic innovator's dilemma, right? Which is like, what do you do? **Swyx** [45:50] Yeah. Do you rearchitecture or do you wait? **Joubin Mirzadegan** [45:53] Do you, do you ar- okay, so that, that happened. Then I come to find out, okay, uh, in this case, Salesforce, which is, like, the gorilla in the room, they have, like, 95% market share, they have end-of-lifed their CPQ solution, and they are making everybody move to a new product, okay? **Swyx** [46:09] Ah. **Joubin Mirzadegan** [46:09] So they are trying to do this. That product does not exist yet. If it does, it's incredibly flimsy. We've talked to some of the people that are trying it right now. And so we basically have a two-year window where we have to beat them to the punch. And we love, we love that, and the reason we love that is like, boy, would I rather compete with, like, whatever, 100,000-person Salesforce that I don't even know what kind of engineers may or may not still be there, versus, like, OpenAI. **Swyx** [46:37] Yeah. **Joubin Mirzadegan** [46:37] You know? **Swyx** [46:38] Yeah. **Joubin Mirzadegan** [46:38] Uh, like, that's just like, that's who we wanna outsprint. Then I started asking myself, "Well, like, why hasn't anybody done this yet?" And the short answer is, one, I don't think the technology was there, and the second, going back to your earlier question, Swix, is this is a very complicated go-to-market and distribution question. It is up-market. The problem is more up-market because that's where the complexity is. And, um, and in order to, like, do something elegantly up-market, you need to, like, know what you're doing in the enterprise. **Swyx** [47:09] Yeah. **Joubin Mirzadegan** [47:09] Right? Uh, and it just so happens that you need early believers, like Glean had with Rubrik, that are willing to take a bet with you in a, like, design partnership to co-develop it with you. And it just so happens, going back to our earlier conversations, that episodes one through 80 were interviewing CROs- **Swyx** [47:29] Exactly **Joubin Mirzadegan** [47:29] ... who are the people that have the pain. **Swyx** [47:31] You've been preparing this the whole time. **Joubin Mirzadegan** [47:32] Then the other thing that I was, like, responsible for the KP was, like, these CIO networks, who are the ones responsible for delivering software to these people to alleviate their pain. And so it's like, I just so happen to know basically all of the key stakeholders in this problem. **Swyx** [47:48] So you're the guy. **Joubin Mirzadegan** [47:49] So actually, at that point I was like, "Oh man," like, "do I really wanna..." Like, life's pretty, like, KP, life's, you know, like, I've s- I know, I have seen what a company, what it looks like, the bite out of your life that it takes to, like, build a company. So anyway, um, point being, um, after talking with, uh, my partner at home and, like, understanding, like, is this a commitment that we're willing to make, uh, and talking to, uh, my partners at Kleiner Perkins, like, uh, folks like Mamoon and Ilya, to be like, "Hey, if we do this, like, I think, I think I have to do it." Like, I, I don't think, I don't think it's gonna really make sense for us to hire somebody off the street right now- And then I'll build a co-founding team that is, like, technically excellent and world-class. So anyway, that was the thing, or I should say the million series of things that, that tipped us over the edge. **Swyx** [48:50] Well, where are you today? What are you ready to share in terms of what the product is, what, what p- the people you're working with, the problems you solved? **Joubin Mirzadegan** [49:00] Yeah. So I will work backwards from the list- **Swyx** [49:04] Yeah **Joubin Mirzadegan** [49:04] ... that you used of how you would evaluate companies- **Swyx** [49:07] Sure **Joubin Mirzadegan** [49:07] ... 'cause it's the same thing as me. **Swyx** [49:09] Wait, money first? All right, let's do it. **Joubin Mirzadegan** [49:10] Team, team first. **Swyx** [49:11] Oh, okay. Oh, yeah. **Joubin Mirzadegan** [49:12] Team was your first, wasn't it? **Swyx** [49:13] Yeah, but you said, you said backwards. **Joubin Mirzadegan** [49:15] No, no, no. Work... I'll work top-down. **Swyx** [49:16] Okay. All right. **Joubin Mirzadegan** [49:17] Team first. **Swyx** [49:18] Yeah. **Joubin Mirzadegan** [49:19] Uh, we're at, uh, nine people today. Two co-founders, AJ and Eugene. AJ went to Caltech at 15 and finished second in his class. Like, the guy was in diapers when he was in school. It's absurd. Met Eugene his first day of school. They've been working together basically ever since. AJ went to Robinhood. Eugene went to Meta. They went to NASA together, built a bunch of the software for the rover, the Mars rover. Then they started a company together called Athena, uh, which was an LLM for college students to send their applications. It would grade it, tell them how is it, all that. Uh, then they realized, like, the TAM or end market of EDU is not that compelling. **Swyx** [50:03] Depends. Like, some- sometimes- **Joubin Mirzadegan** [50:04] It depends. They were not that inspired by it. They wanted to go build- **Swyx** [50:07] If you're a capital and, like, you, you can do a sustainable business. **Joubin Mirzadegan** [50:10] That's it. **Swyx** [50:10] Yeah. **Joubin Mirzadegan** [50:10] They wanted to go build a giant company. They independently found this problem, independently got excited about it. **Swyx** [50:18] Sales- salesforce CPQ? **Joubin Mirzadegan** [50:20] How do you deliver better software for, for AEs? Yeah, CPQ. **Swyx** [50:23] Yeah. **Joubin Mirzadegan** [50:24] Okay? Because they were asking their founder friends, like, "What's the number one problem at your company?" And they kept answering this question. So anyway, then we met. It became very obvious that what I had was, like, unfair distribution, an understanding of the problem coming from sales, and what they had was extraordinary technical chops. So anyway. **Swyx** [50:45] That's team. **Joubin Mirzadegan** [50:46] That's team, plus, uh, some killers, uh, across the board. By the time this comes out, we'll have soft launched. The only other interview that I'm doing besides you is with Mamoon interviews me on Grit, where we'll talk, we'll talk about it. We're co-developing the solution with design partners. I was very inspired by what Glean did. So Glean built for Rubrik. We're building for four design partners, shared Slack channel, weekly stand-ups. Like, we are taking the same bet that basically Glean made, which is that what these four design partners want is probably gonna be what the rest of the world wants. **Swyx** [51:22] Do you want diversity in the, in those four? Like, you know what I mean? **Joubin Mirzadegan** [51:25] What you really want is we had to make sure that our data model is infinitely flexible. **Swyx** [51:30] Yeah, exactly. **Joubin Mirzadegan** [51:30] That we don't run into the next permutation that we haven't seen. And so what you want are the hairiest design partners that have every SKU, hardware, software, SaaS, consumption. Like, you want the mess- **Swyx** [51:46] Okay **Joubin Mirzadegan** [51:46] ... to throw that at your data model to make sure that nothing tips it over. And so those are the types of, of, of design partners that w- that we wanted, and it's helpful. Like, I know the CIO, I know the CRO. In most cases, I know the CEO, and so, like, you don't have to deal with the, like, normal big company BS of, like, legal and procurement and all these things. They can, like, you know, help shepherd you through the org. **Swyx** [52:10] Yeah. Let's talk about data model. H- Did you get it right from the start, or what was the biggest changes that you've done since you started? **Joubin Mirzadegan** [52:19] Yeah. The team probably spent only doing data model. That is it. Like, late nights. **Swyx** [52:27] And what does do data model mean? Like- **Joubin Mirzadegan** [52:28] For example, there are rules that every customer has where it's like, if you're a AE in the UK, you can only quote certain SKUs that have certain discounts on them. Like, you can only have so many... There's only a max discount that you can present a customer, right? If you're doing a deal through a channel partner, and you're doing it out of Canada, there's all these rules that are connected to it. So imagine, like, all of these SKUs, all of these rules, all of this thing is like this extraordinarily interconnected system that has to be accounted for. And so making sure that we threw as much of the real-life information, rules, and permutations as possible to, like, not tip over the data model was incredibly, incredibly important. So, like, that's where we spent a large, large portion of the time getting right. Does that make sense? **Swyx** [53:24] Yep. And I also know that, you know, best laid plans run into reality, and then they get screwed up with the first contact, right? **Joubin Mirzadegan** [53:31] For sure. Like, you know, even if you get consumption right, for example, where you're like, "All right, they can do it," how do you represent that on the UX, right? Or cognition or Windsurf? Like magic. And if you get that right, which is, I think, what we're about to get right, then you earn the right to go build a big company. **Swyx** [53:53] That's... I, I like the way that you phrase that. I love earn- earning right to do bigger things. Like, you don't, you don't... What-- Something that makes me uncomfortable with founders saying, "Oh, we'll build a compound startup" in, as early as you are, is, while the ambition's very big, but have you earned it? **Joubin Mirzadegan** [54:08] Hundred percent. Can I actually tell you one other thing that kind of annoys me? I think a lot of times, uh, in the Valley, founders will pretend like the mission that they have is, like, bigger than it is. For example, if you're doing what we're doing, I think we're solving a really important problem for a certain set of people, okay? **Swyx** [54:30] High-value people? **Joubin Mirzadegan** [54:31] Yes. **Swyx** [54:31] Yes. **Joubin Mirzadegan** [54:32] But, like, we're not helping a mental health crisis. We're not, like, feeding people in other countries, you know? Like, we're not doing what, what the Chan Zuckerberg Initiative is doing. And I think it's really annoying when people pretend like what they are doing is like this revolutionary thing. It's like, no, what you're doing is solving a really hard problem for a specific set of people. If you're able to solve that problem and those people are delighted, then you earn the right to go solve the next problem. If you solve enough problems in perpetuity, then you earn the right to go build the big company, and when you go build the big company, then you get all of the cool things that come with that. People taking on bigger roles and responsibilities than they ever had, engineers owning new product initiatives, soup to nuts, ICs that then become managers that have no business becoming managers. Of course, all the financial stuff that comes with that. In my mind, I'm like, "That's a mission that I can get behind." You know? I still think the problem that we're solving is interesting and cool, but I think it's really annoying when you're like, "Oh my God, this is like the thing that I've been thinking about since I was one years old," and everybody else also has to feel like this... I don't know. I, I find that annoying. **Swyx** [55:46] Well, sometimes you have to just pump- puff yourself up for the fundraise- **Joubin Mirzadegan** [55:50] Yes **Swyx** [55:50] ... but there's always, like, sort of two versions of the story. AI findings. Uh, you know, we are- we're an AI engineering podcast. We do care about how AI's being utilized to transform and rev- revolutionize things. I think you're gonna find it in small little ways, but any surprises? **Joubin Mirzadegan** [56:06] I think if you dream the dream, um, where LLMs will be a superstar in, um, in this company is, like, if you're one of our customers and all quotes go through Roadrunner, okay? Basically, you can imagine a world where it just recommends, like, just do this deal. Like, oh, you're doing a deal at Costco? Great. We just did a deal with Nordstrom that looks a lot like this deal, okay? Uh, you should adjust these things and then- **Swyx** [56:33] Ah **Joubin Mirzadegan** [56:33] ... deliver it this way. And so the system- **Swyx** [56:36] Like proactively suggesting things? **Joubin Mirzadegan** [56:37] Exactly. The system will basically have all of the historical information about what have you done, and once it has all of that, it will then tell you, "This is how you should bundle it up." And by the way, today, that's all human in the loop. Today, if you're a new rep at Glean or a new rep at Cognition and you wanna, like, put one of these deals together, you're, like, calling deals desk and finance. You're, like, calling the top AEs at the company and be like, "How do you even, like, put this together?" Right? And then if you're using Salesforce CPQ, which most people are, you, like, then go into, like, loading screen hell. Then you've built a bunch of custom software on top of that because the data d- model doesn't work, so you have to, like, fits around with it to, like, actually make it work. Like, it's a complete nightmare. **Swyx** [57:18] Yeah. **Joubin Mirzadegan** [57:18] Um, and so, like, that is where the magic of, of Roadrunner will, will come. **Swyx** [57:24] So you're... Maybe if I can abstract a little bit, you're kind of automating the deal desk and not the AE. You're extending, you're augmenting the AE. You're improving ramp-up time for the AE or productivity of the AE. **Joubin Mirzadegan** [57:35] How would I describe it? I would say we are- **Swyx** [57:37] Like, whose job are you taking away? **Joubin Mirzadegan** [57:39] Like, I would say, um, very specifically, AEs are quite expensive, and they spend a ridiculous amount of time doing administrative work trying to get these hackie systems to go. **Swyx** [57:51] Perfect. **Joubin Mirzadegan** [57:51] And right now the amount of bouncing around and ping-ponging that they have to do inside of an organization just to get a quote created and approved is a nightmare. We should solve that. And by the way, guess what? Deals desk and all these people should not be doing that either. **Swyx** [58:06] Yeah. **Joubin Mirzadegan** [58:06] You know? **Swyx** [58:07] Yeah, yeah. **Joubin Mirzadegan** [58:07] Like, there's way more strategic things that they could be doing. **Swyx** [58:09] Yeah. I mean, in, in, in Cognition it's just, like, a really active Slack channel where everyone's just throwing stuff at each other all day long, and it's, it's a mess. **Joubin Mirzadegan** [58:16] Yeah, it's mayhem. Yeah, it's complete mayhem. **Swyx** [58:19] Um, interesting. Okay, so any- anything else you wanna cover on just Roadrunner in general, like your vision? I think we covered a lot of it. Just any part of the story that, uh, you know, you wanna get on the record. **Joubin Mirzadegan** [58:34] No. I would just say, like, we are not demand constraint. Like, I know every customer, and they're all, like- ... banging down my door right now. The only fight that I've ever had or have with my co-founders is that I'm like, "Hey, these 10 customers wanna come and join us and, and work with us," and they're like, "We do not have engineering bandwidth." Like, our roadmap is being dragged out of us. **Swyx** [59:00] Yeah. **Joubin Mirzadegan** [59:01] It's very clear what we have to go do. There's no, like, surprises from here on the things that we need to go actually build. Obviously, the strategy is the same. The tactics will bob and weave. And so, um, yeah, we're, um- **Swyx** [59:14] You need product and eng **Joubin Mirzadegan** [59:15] ... we are meaningfully bandwidth constrained on amazing talent that wants to go through the grind of building an early-stage company. **Swyx** [59:25] Yeah. Well, we'll, we'll, uh, get you that. Kleiner is very good at getting that, uh, and I don't think, I don't think there's any doubt there. Okay, so just zooming out a little bit, I was prompted a bit earlier, you're, you like running a lot. ### High Performance **Joubin Mirzadegan** [59:36] Uh-huh. **Swyx** [59:37] Just tell me more about, like, just the, the general overall philosophy of high performance, right? I guess, like, it kind of, what does that mean to you? I think we had this conversation about this. What does that mean to you from, like, your personal life into work? **Joubin Mirzadegan** [59:51] I'll be like, I'll try and be tactical- **Swyx** [59:53] Yeah **Joubin Mirzadegan** [59:53] ... rather than abstract. So physically, to your prompt on running, I work out every day no matter what. I- **Swyx** [1:00:01] First thing **Joubin Mirzadegan** [1:00:02] ... sweat every day as soon as I wake up. **Swyx** [1:00:04] Home gym. **Joubin Mirzadegan** [1:00:04] It's either... So Mon- it's, it's pretty consistent. Mondays I bike up Hawk Hill, which is, like, over the Golden Gate and up into the Headlands. It's, like, a nice way to start the week. I'll run twice a week. I'll usually lift weights twice a week. Uh, usually play a sport or something. **Swyx** [1:00:19] So what sport? **Joubin Mirzadegan** [1:00:20] Basketball has been the sport of choice recently, although every time I pick up a ball, I'm, like, pretty convinced I'm gonna, like, you know, like, tear my ACL or something, you know? Uh, anyway. **Swyx** [1:00:32] Depends on how hard you push yourself. **Joubin Mirzadegan** [1:00:33] Yeah. **Swyx** [1:00:33] I guess you push, push pretty hard. **Joubin Mirzadegan** [1:00:34] Yeah. Physically, I, I will, um, work out every day, salad for lunch every day. I've been do- it's just easier. I've just found that if I can just do the same things over- **Swyx** [1:00:44] Yeah **Joubin Mirzadegan** [1:00:44] ... and over again, my life is just easier. I don't have to think about it. Like, for example, on the working out thing, it is way easier to know that I am gonna work out every day rather than have the cognitive load of, like, what days am I gonna work out this week? **Swyx** [1:00:57] Yeah, yeah. **Joubin Mirzadegan** [1:00:57] Or when am I gonna do it? Or, like, for lunch. I'm just gonna have a salad. **Swyx** [1:01:01] I have salads for lunch. **Joubin Mirzadegan** [1:01:02] Yes, there's no choice. I don't wanna make the choice. **Swyx** [1:01:04] The way I phrase it, I think Tim Urban says this, it's much easier to do something 100% of the time than it is to do it 90% of the time. **Joubin Mirzadegan** [1:01:11] 100%. **Swyx** [1:01:12] Right? **Joubin Mirzadegan** [1:01:12] Like, think about if you were deciding, "I wanna work out four days a week," then you have to figure out, like, what are you gonna do? **Swyx** [1:01:17] Yeah. **Joubin Mirzadegan** [1:01:18] You know? **Swyx** [1:01:18] Like, you know, did I skip yesterday? Does that mean I can skip today? Or, you know. **Joubin Mirzadegan** [1:01:22] Exactly, and even to your question on, like, the style of workout, like, I'm just doing whatever I feel like, besides Mondays, like, I feel like doing that day. And even if I go and, like, lift at the gym, it's just full body, whatever I feel like is next, I'll compound every exercise and I'll just run through it. Like, I don't have, like, a set... 'Cause I just wanna reduce friction as much as I can to just, like, get those things done. **Swyx** [1:01:43] On a personal reflection, like, there's a real reason I'm asking this question, but as just a side comment, and you, you can comment if you want. I feel like this is so important, like, your personal health and your fitness and your sort of peak productivity practice, that I find it interesting that VCs don't do that to their founders. Like, "Hey, I'm gonna lock you in a room." Basically, only HFZero does this. "Hey, I'm gonna lock you in a room, um, you know, like, make, make you, make you eat healthy, make you, like, like, you know, take care, take care of everything so you can go work on a company." Cognition has a engineering sort of basement, and I've advocated pumping oxygen into there because that is, like, a very valuable thing to have and, like- **Joubin Mirzadegan** [1:02:21] The, the problem is- ... that it kinda has to come from within, meaning, like, it kinda has to be a habit that you've had that you can then carry on to founding a company. Because, like, the amount of demand on your time, it's like a pie eating contest and the, the prize is just more pie. And so, like, there is no limits to how much has to be done. And so I think I just got lucky where I had some of these habits before- **Swyx** [1:02:45] Yeah **Joubin Mirzadegan** [1:02:46] ... and then I was able to just, like, carry them on. Otherwise, like, even now, I'm like, I feel very constrained being able to do some of these things. **Swyx** [1:02:53] No, totally. Kind of the real reason I was gonna ask was you listen to a lot of podcasts while you're doing all this. **Joubin Mirzadegan** [1:02:58] Mm-hmm. **Swyx** [1:02:58] What are your favorite other podcasts? **Joubin Mirzadegan** [1:03:00] Oh, man. **Swyx** [1:03:01] Just shoot- **Joubin Mirzadegan** [1:03:01] Do you listen to your own pod- **Swyx** [1:03:02] Shoot us some recs. Yeah, I do. I'm very critical. I sh- I send notes to my editor, my co-hosts, um, yeah. **Joubin Mirzadegan** [1:03:07] I used to listen to every one, and then my editor was like... 'Cause it was like r- before we would release, I would have, like, a litany of notes, and eventually they're like, "Dude, we've been doing this for, whatever, 200 plus episodes. Like, you don't have to listen to every one and send notes. Like, it just bogs down everything. Just, like, trust us." So I've stopped. **Swyx** [1:03:25] But it's also- **Joubin Mirzadegan** [1:03:25] I've created some space. **Swyx** [1:03:26] Yeah, right. Anyway, so I wasn't asking about our pod, but just, like, just other pods that you enjoy and recommend to others. I'm just giving people recs. **Joubin Mirzadegan** [1:03:34] I think some of, uh, O'Shaughnessy's Invest Like the Best are pretty good. **Swyx** [1:03:38] This whole thing with Colossus. **Joubin Mirzadegan** [1:03:40] It's, yeah, it's interesting. **Swyx** [1:03:41] Yeah. **Joubin Mirzadegan** [1:03:41] I think some of Joe Rogan and some of Tim Ferriss is good. **Swyx** [1:03:46] Uh-huh. **Joubin Mirzadegan** [1:03:47] Some. **Swyx** [1:03:47] Yeah. **Joubin Mirzadegan** [1:03:48] Some of Shane Parrish is good. **Swyx** [1:03:49] Yeah. **Joubin Mirzadegan** [1:03:50] Like, uh, I have guests that I like when they interview them, but I don't follow... I personally don't follow any host religiously. **Swyx** [1:03:59] Yeah. **Joubin Mirzadegan** [1:03:59] Like, I get interested in guests- **Swyx** [1:04:00] Yeah **Joubin Mirzadegan** [1:04:00] ... and then I'll go down the rabbit hole for, like, what shows have they been on, and then I'll just listen to those, and then if I like the interviewer, then I'm like, "Oh, this is a new show. Maybe I'll go check out one or two more." But I'll go like, like, for example, like, I've gone as deep as deep can go on Elon. Like, there's probably... I have probably listened to... And he does a bunch of them, you know? I've probably listened to a bunch of them, and if he's been on- **Swyx** [1:04:23] He's not the easiest speaker to follow. **Joubin Mirzadegan** [1:04:25] No, it is a bit jumbled. **Swyx** [1:04:27] Yeah. **Joubin Mirzadegan** [1:04:28] Uh, so I'll go deep on a guest. I'll go deep on a guest. **Swyx** [1:04:32] Have you done speaker training? **Joubin Mirzadegan** [1:04:34] No. **Swyx** [1:04:34] Coaching? You know, uh, we're considering that. Just 'cause, you know, you basically do public speaking as part of your job, right? And well, you should probably get coaching for it, just like anything else. **Joubin Mirzadegan** [1:04:44] You know, my reflection doing this with you now is that asking the questions is way easier than answering them. And so- **Swyx** [1:04:54] How's it feel, huh? **Joubin Mirzadegan** [1:04:54] I would say, I would say on the... You have way more control over a conversation when you're asking the questions. **Swyx** [1:05:01] Yeah, sure. **Joubin Mirzadegan** [1:05:02] And- **Swyx** [1:05:02] I'm just, I'm just loving stuff here **Joubin Mirzadegan** [1:05:03] ... yeah, exactly, and you're usually speaking, whatever, like 20% of the time, and the guest speaks, like, 80% of the time, and you, like, have a general sense of where you wanna go. And so- **Swyx** [1:05:11] Yeah, I got the plan here. **Joubin Mirzadegan** [1:05:12] Yeah, and, and like, you know, uh, maybe if I were to do more on this side of the table versus yours, I think speaker training might make sense. **Swyx** [1:05:20] Yeah, well, you know, spe- speaking comes in all shapes and forms, including running a company. **Joubin Mirzadegan** [1:05:23] Yeah. **Swyx** [1:05:23] So, so, uh, I do view it as a very general use case. For me, I run a conference, and so I do the keynote every time, every conference, so it really actually does matter 'cause I set the example for my speakers. **Joubin Mirzadegan** [1:05:33] My favorite definition of sales is an ability to transfer enthusiasm from one person to another. And I think that when you're recruiting, when you are on stage at your conference speaking, when you're an interviewer or interviewee, when you go home for the holidays and hang out with your family, like, I think all of that, I really like this definition of, like, how do you transfer enthusiasm? And I think it has to be raw and I think it has to be organic. Uh, I think that's, uh... If I were to, like, train or be trained, I would really try to get to the essence of, like, how do I help transfer my enthusiasm about whatever it is that I'm talking about into those that are listening? **Swyx** [1:06:16] Yeah. Uh, uh, the challenge for you is you're pretty naturally good at it. So it's gonna be hard to find someone who's better than you to- To train you. So- ### Grit Defined **Joubin Mirzadegan** [1:06:26] Appreciate it **Swyx** [1:06:26] ... you know, a bit of a compliment. Uh, speaking of definitions, my favorite closing question, what is the definition of grit to you? **Joubin Mirzadegan** [1:06:32] The namesake of the show came from Angela Duckworth's book, Grit, who I had the, the honor of flying out to, to Pennsylvania and interviewing- **Swyx** [1:06:40] Yeah **Joubin Mirzadegan** [1:06:40] ... which was amazing. **Swyx** [1:06:41] This thing's cool. We... So the background also is that Penn invented positive psychology, or pioneered positive psychology, and she came from that line of thinking. **Joubin Mirzadegan** [1:06:50] Yeah. And her definition is... I mean, she wrote a book about it, so it's hard to define it quite narrowly, but passion plus perseverance over a sustained period of time. And I think the, like, natural tendency when you think about grit is, like, literally gritting your teeth. Like, how do you just endure? And I think the, like, operative word in her definition is passion. The way that I think about it is, like, how can I put myself in positions where the thing that I'm doing, the thing that I'm working on, the job that I'm doing, the company that I'm building, the relationship that I'm in, how can I be in the-- more of those situations where I really care? Because if I really care, then I can transfer my enthusiasm to others. If I really care, then it'll feel like play to me when it feels like work to everybody else. If I really care, like in the podcast example, I'll just do it for longer than anybody else and just, like, out-sustain you. But I think it's all because I really care. And so I think this idea of passion is probably the thing that I love most about her definition, which is like, I don't know, I just try and do things that I really care about, and therefore it's just-- like, it feels light for me, and then I don't have to feel like I'm always gritting my teeth to do things that matter. **Swyx** [1:08:12] It's probably a superlative form of grit that really captures that. It's gonna-- flow state grit or passion grit or whatever adjective you wanna add to it- **Joubin Mirzadegan** [1:08:21] Totally **Swyx** [1:08:21] ... that would be nice. But thanks for being on Lean Space. I, I feel like I've been a little bit experiencing the grit ex-experience myself, and thanks for, um, joining us. **Joubin Mirzadegan** [1:08:30] It was hard for me not to- **Swyx** [1:08:32] I know **Joubin Mirzadegan** [1:08:32] ... ask you too many questions. **Swyx** [1:08:34] I know. **Joubin Mirzadegan** [1:08:34] I tried not to. **Swyx** [1:08:35] But you get one. You get one. What, what, what's, what's, what's on your mind? **Joubin Mirzadegan** [1:08:37] Do you have a dream guest? **Swyx** [1:08:39] Dream guest I would say is a supporter of ours that is-- that has promised to be on at some point, uh, Andre. He's a- **Joubin Mirzadegan** [1:08:48] Karpathy? **Swyx** [1:08:49] Yeah, yeah. He's, uh, been a mentor for a long time. He's, he's a teacher. He's, he's very authentic and very super knowledgeable, and I think an inspiration for a lot of us who are trying to figure out, you know, like, from, from trusted sources, like, the truth of what is possible with LLMs. And he's very autodidactic as well, which is something I strongly identify with. Um, you don't really know something unless, unless you've really taught it to yourself and, and built everything, a, a version of it for yourself. And he does represent the simplicity and clarity that I want to see in the world that I try to represent with Lean Space. **Joubin Mirzadegan** [1:09:25] Really cool, man. I appreciate you doing this. **Swyx** [1:09:27] Yeah, you too. **Joubin Mirzadegan** [1:09:27] It's, uh, first time I've been- The tables have been turned on me. Crazy experience. **Swyx** [1:09:32] First of many. **Joubin Mirzadegan** [1:09:33] Thanks, man. --- This library is powered by PodHood (https://podhood.com), the podcast website platform.