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Podcast Episode Notes: The Pull to Build: Joubin Mirzadegan on Grit and Starting Roadrunner
Podcast Overview
- Title: Grit
- Description: Grit explores what it takes to create, build, and scale world-class organizations, featuring leaders making a difference.
- Host: Joubin Mirzadegan, Partner at Kleiner Perkins
- Episode: Special reverse episode with Joubin as the guest, hosted by Mamoon Hamid.
- Focus: Joubin’s transition from advising founders to becoming a founder himself with the launch of Roadrunner, an AI-native CPQ platform.
Key Participants
- Joubin Mirzadegan: Co-founder & CEO of Roadrunner
- Mamoon Hamid: Host and guest in this episode, discussing Joubin's journey.
Episode Highlights Joubin’s Background
- Joubin has a diverse educational background with a BA in International Relations and Anthropology, influenced by his Iranian immigrant family's journey.
- He has held significant roles in sales and leadership, including positions at Bracket Computing, Evident.io, and Palo Alto Networks before joining Kleiner Perkins.
Transition to Entrepreneurship
- Joubin's entrepreneurial spirit emerged from a desire to create solutions to problems he faced in sales, particularly in the CPQ (Configure Price Quote) space.
- The inefficiencies in existing software systems drove him to develop Roadrunner, which aims to modernize the quote-to-cash process using AI.
Roadrunner Overview
- Core Focus: Building an AI-native CPQ system that simplifies the deal-making process for sales teams.
- Pain Points Addressed:
- Outdated software causing inefficiencies in sales operations.
- Complicated pricing models that complicate deal closures.
- Technological Innovation: Utilizing large language models (LLMs) to create a system that can quickly structure deals and provide business intelligence for pricing and approvals.
Joubin’s Co-founders and Team
- Joubin partnered with engineers AJ and Eugene, both with impressive backgrounds in technology and previous startups.
- The team is focused on building a capable product that meets the demands of early customers.
Reflections on Grit
- Definition of Grit: Joubin defines grit as the ability to persistently pursue goals over a long period, regardless of obstacles.
- He reflects on his journey in the podcast, recognizing the importance of resilience and long-term commitment in both building a startup and succeeding in sales.
Insights on CPQ and Future Vision
- Importance of CPQ: Joubin emphasizes that CPQ is the cornerstone of the sales process, impacting revenue generation directly.
- Mission Statement: He is cautious about traditional mission statements but believes in solving concrete problems to earn the right to build a successful company.
Key Takeaways
- Transitioning from advisor to founder presents unique challenges and opportunities.
- Roadrunner aims to disrupt outdated sales processes through innovative AI solutions.
- Building a startup requires resilience, adaptability, and a clear vision of the problems being addressed.
- The synergy between Joubin's experience at Kleiner Perkins and his new venture illustrates the potential for impact when leveraging networks and expertise.
Closing Thoughts
- Joubin views entrepreneurship as a chance to test one’s capabilities and grow personally and professionally.
- He celebrates the journey of building a company that not only aims for financial success but also has the potential to change lives by creating job opportunities and fostering community engagement.
Call to Action
- Roadrunner is actively hiring to expand its engineering team as it continues to develop its cutting-edge platform.
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This structured summary encapsulates the key discussions from the podcast episode, providing insights into Joubin Mirzadegan's journey, the vision behind Roadrunner, and the concept of grit as a fundamental trait in entrepreneurship.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Transcript
Automatic transcript. May contain errors.0:00The entire life cycle of business processes, you deliver a product. in order to deliver that product, you need like a piece of paper that says, what are you delivering? And in return, you get money. There is an underlying operating system that enables all of that to happen. That all happens in very, very, very old and bad software today. And so that's like what we're solving first. And we think it's like pretty important. Imagine a world where if you're a customer, every quote that goes through Roadrunner has a series of tags that are associated with that quote. And so an account executive in natural language can say, this is what I want.
0:35And the system will basically say, you know, what you want to do, we have done a deal like that before. You should structure it just like this. Perfect for their comp plan, maximizes their commission, perfect for the business. All of that, LLMs, a central nervous system that can just tell you right when you say it exactly how to structure the deal, and then be able to on the fly, give you all of the benchmarking around the discounts to get these things approved very quickly. And this is the tagline of the company, we can put revenue back in motion, because right now it is stuck.
1:29Today on Grit, we're doing something special. This is a role reversal episode. Jubin is normally the host of this show, but for the first time in over 270 episodes, we're turning the table and putting him in the hot seat. We'll cover everything from his childhood, building startups, then joining Kleiner Perkins to help founders build their companies and launching this podcast along the way. And now stepping into a new chapter as co-founder and CEO of Roadrunner, the first company KP has incubated since Clean. You wanna do this? Yeah, let's do it. Showtime? Let's roll. Let's do the role reversal.
2:02Let's do it. Yeah? Let's do it. Well, in the true Jubin form, I'm going to read back your own background to yourself. And then you correct me if I got this right. Great. Okay. Great. And then we'll go deeper, obviously. We're going to go back to the early Jubin days. You have a BA in international relations and anthropology from UC Davis with a minor in Spanish. You grew up Iranian immigrant family. Parents divorced when you were five. you split your time between two households, weekdays with mom and stepdad, and then weekends with dad here up in the Bay Area. Your first job was as a BDR at Bracket Computing in inside sales, and Bracket was an early cloud security company.
2:51Then you went to Evident.io, where you were a mid-market AE. Wow, like you upgraded, huh? From inside sales to mid-market AE. You were the top performing AE. Yeah. And became a hiring leader. Doubled the company and logo count in your first full quarter. That's what closers do, right? And then you went to Palo Alto Networks, where you became a central U.S. sales leader. Moved to Chicago, right? Moved to Chicago. We'll have to talk about Chicago a little bit and your tradition in Chicago. Built the region from small renewal space into a major ARR engine for the company. And then finally, in 2019, you joined us here at Kleiner Perkins as a go-to-market partner.
3:34And now you're obviously a partner running our portfolio operations. And you decided along the way to start this podcast in 2020, not too long after you joined us here as an experiment to talk to a bunch of CROs at the time. And then you've had now over 270? Yeah. conversations with CROs, CEOs, and go-to-market leaders. Some incredible guests, not including me yet. Oh, you think it's because I haven't tried? We'll have to try again. And now you're the founder and CEO of Roadrunner, the first incubation that we've done here at Kleiner Perkins since 2019 when we incubated clean in this same building.
4:21Is that all accurate? That's all pretty accurate. Can I like put some color on one or two things? Yes, please. The first startup that I joined, Bracket Computing, raised$130 million from many of our peers on Sand Hill Road. And it was like very, very early cloud security. Like the only people that were on AWS at the time were like Goldman Sachs and maybe one or two banks. I used to get on a bike in the mission. I had a shared sliding door with me and my roommate. I would bike in a blazer to the Caltrain station, put the bike on the Caltrain station and then be like pouring sweat and then start ripping cold calls and doing emails on the train down.
5:03I used to wear a blazer because like I want it to be taken seriously. By the way, I wore the blazer when I joined KP too. Yeah, yeah, yeah. There's two things actually I picked up in our interview when I interviewed you. Two things that just came through. One is you wore the blazer. You're very like, look the part, right? And the other thing was you kept calling you man or dude. How does someone in an interview just call someone dude and man? I didn't know what to make of it to be honest. My read was, I actually didn't think our interview went very well. And now that you say that I kept calling you man and dude, it kind of makes sense why I didn't think it went very well.
5:45I'm just not used to being called dude and man in an interview. While wearing a blazer trying to be taken seriously? Yeah, it was just like two like - Yeah, it's good. That's good. That's good. That's real nice, Jubin. Yeah, it was like two different sides of Jubin all coming through. So anyway, long story short, I remember falling in love with startups, even though we never found product market fit. Never. We had closed like barely any revenue. And at like 21, after like making, spending a year making way too many cold calls, they asked me to hire an inside sales team. I hired the team. Then three months later, I had to fire basically the entire team.
6:24I remember this like crazy feeling of like, man, this sucks because it doesn't work. But oh my God, like I can just hire who I want and we can just call anybody in the world and like pitch them our product. Like it felt like make-believe business where I was like, you can literally just do anything you want without like any oversight. And that was like startups. Like I didn't realize like that's how startups work, where you just like get to put your will into the world. Yeah. And some of it's like very messy. A lot of it's like very wrong, but like you get to just do what you think is right. And so like that seed was the thing that has basically stayed with me my entire career, which is like, I want to be in startups no matter what forever.
7:05So like even fast forward to KP, I remember thinking, I have no idea what this job is. I have no idea how it's going to be. That's how we felt. At Kleiner Perkins. I had no idea, but I was like, you know what? They're around startups all the time and they're around founders all the time. And that felt right to me. You know what I mean? I don't know if you remember this, but two weeks into the job, we sat down and I was having like a existential crisis. Oh yeah, I remember this. I was like, Mamoun, like, I think this is, I don't think we made a wrong decision. I'm like, what are you talking about?
7:41I'm like, I don't know. I just, I can't get over this feeling when I'm sitting across the table from entrepreneurs and people building companies that I'm on the wrong side of the table. Like, I feel like I should be building with them. Yeah. It's the conversation we have every month, our monthly one-on-one. It's exactly like, I think I'm in the wrong job, but it's a recurring conversation. And so maybe let's just tell me more about the BA in international relations and anthropology. Yeah. Interesting set of majors. I wanted to take majors that had as few science classes as possible. And the reason for that is because growing up at my dinner table, my mom and stepdad were both scientists, PhDs in chemistry and biology, respectively.
8:23And they worked together at Roche, what is now, I guess, VMware. And so they worked together and they were both like, you know, in the same field. The conversation was always around science. Okay. And work. and I remember falling in love with the like work part. I just thought it was cool that they were like talking about work, but then I hated the science part. Okay. So I chose the majors that I did not have to take any science in. This is your way of revolting. In some ways. And then after like a year of school, I was like, I am not like, I cannot sit still in a classroom. Like I am not, this is not how I'm going to learn.
8:56And so I stayed at Davis every summer, just taking classes so I could get out of there as quickly as possible. So I graduated early, like three and a third year. Okay. and so I could go work. We have not talked about this before. So I could go work. I was so eager to work. No, this is the, both of us. I finished college in three years because I could not sit still in classes and I wanted to get out of school. I didn't know that. Yeah, yeah, finished college. Yeah, three and a third. I did the last summer so I could get out in three years. I couldn't wait. Yeah. When I graduated Bracket, I fell in love with like this cloud security thing.
9:29It just felt like the next thing at the time. And I was trying to convince them that I was worthy of being a BDR, like an inside sales rep making cold calls. And they kept saying, you know, you're too raw. I just, you know, we want someone that has like a year or two of experience. And so I went and I would get BDR job offers. And after every offer, I would send them the offer letter. And I would say, hey, like, you know, Yelp thinks I'm worthy of a BDR, like you don't. I did that 16 times. And so I sent them 16 offer letters. And that was over the course of like three months going into summer because I was early.
10:06And then eventually I signed the 17th one. By the way, crazy, crazy. The company was Aptus, which is like who we're now in some ways kind of like trying to build the next generation of it. Roadrunner, insane. And then I sent it to him. I'm like, I'm starting Monday. I appreciate everything. Just wanted to let you know. Hopefully our paths crossed again. And they called me the next day and they were like, come in, we're going to make this work. So anyway. Wow, I thought I knew you. I'm knowing more, getting to know more of you. That's how you do podcasts. That's how you do podcasts. That's your trick.
10:40How you get to know people better. That's right. All right, well, let's go back to the four, the five-year-old Jubin who grew up, you're splitting time in two different locations, two different homes. Yeah. Iranian immigrant family. Yeah. Imagine you're speaking in Farsi at home. Take me back into five-year-old Jubin's home. I didn't speak English until I was in first grade. It was pretty awkward having a name like Jubin and not speaking any English when I was young. When my mom and stepdad moved to San Diego when I was a freshman in high school and growing up, they were in the South Bay and my dad was in San Bruno.
11:13And so basically the way that it worked out was I would spend most of the week with my mom and then usually Sunday and then Monday, my dad would drop me off at school. It was two extreme versions of the world that I would live every week. Like one was my mother who was very like strict and disciplinarian, school, studying, grades, jobs. And then my dad who would basically let me do whatever I wanted. And so like I kind of held both of those things together where I think in some respect, I grew up pretty quickly with my dad at a pretty young age. Is this like the suit jacket and the dude man, like two extremes?
11:57Yeah, that's probably true. I've never thought about it that way. But yeah, that's probably true. Where in some ways, like, I take things very seriously. And in other ways, I take things extremely unseriously. And so anyway, like, I held those things together for a while. I find that you're very particular about the attention to detail, how you show up. And is that something you've developed? Or if you look back again, like the child, the 10-year-old version of yourself now, And one thing that always comes to mind is whenever we, you always wear a watch because you always need to tell time and you're always in a rush.
12:34Like, where did that come from? I certainly think that I have ants in my pants. So like that, that has never changed. My youth soccer coaches used to call me Spunky. That nickname probably is still relevant today. Like, I cannot sit still. It's just that thing. I won't call you Spunky. It's just like, it's just the ants in my pants. You know, like I have too much energy, which is why I work out every day. I have to like walk the dog exhausted. I think my mom taught me like this extreme discipline. Like I am, as you know, like kind of psychotic about the things that I do every day. Yeah. And I'm very consistent in how I do those things.
13:10And then I think if I was being honest with myself, I think my dad taught me some level of irreverence where you use the word lash out. I think I have this thing about me where anytime I'm told what to do, I want to do the opposite. Anytime I feel like somebody's making a decision that's not right, I'm not afraid to say it, I will confront the situation pretty cleanly. I try not to overly formalize things. And I think that comes from him. Even in our interview, I think I try and be authentic in myself. And I think that's balanced with a lot of what my mom gave me, which is like pretty hardcore discipline What are the three words then you you'd use to describe yourself as a kid Anxious you know, I moved to san diego when I was a freshman in high school My parents divorced when I was young.
13:59I'd never been to san diego until we moved there. I didn't know anybody there Lived with my dad on the weekends and my mom. My mom was a single mom Raised me Alone until my stepdad couldn't really afford the mortgage very well. You can feel that TV dinners with my dad most nights. There was times where, you know, we wouldn't pay rent and you'd stay in, you know, places you probably don't want to stay. And I think as a kid, like when I say growing up fast, like you feel that. Yeah. And that's how you grew up with your dad on weekends. Yeah. And with mom, it was a bit more structured. Yeah. Structured.
14:33But you got to feel the other way of life. Yeah. And you can feel mom like striving, right? Like she didn't finish her PhD till 35 years old. Like didn't start making a dollar until she finished her school and came out in debt. How old were you then? Maybe like three or four. Okay. I think I internalized that angst a lot. So I say that's probably like one thing. The second is competitive. Like I think I had a spirit of competitiveness that has shown up basically my entire life. When I was young, I was very undirected in what I wanted to do. I think if people ask me now, Like if you asked me over the last six, seven years of getting to know each other, you'd probably say like, I'm driving pretty hard.
15:13Yeah. I think I was relatively rudderless when I was, when I was a kid, just trying to figure things out and honestly, like find my place in the world. Like I was the five, two kid in the center of every class picture, you know, like in every, every childhood picture from first to eighth grade, I was front and center because I was the short, the shortest kid in the class. You know, they always put the shortest kid in the front, which is kind of crazy if you think about it. You were short growing up? I was short growing up, yeah. And you know, like - You're like six feet. Yeah, six feet now. Yeah.
15:43Yeah, late growth spurt. Yeah, same by the way. You were? Yeah, I was like five, seven when I graduated from high school. You're kidding me. Yeah. And you're like six foot now? Yeah. Huh. I was 16, but when I graduated from college, I was 19 and I was still growing. Dang. Yeah. So yeah, got to six feet in my late teens. Dang. Yeah. Yeah. So I always felt like I was like trying to prove myself. Like I always felt like I was trying to fit in somehow. Like I wasn't the short kid, you know, I always felt like I, you know, wanted to belong in some community. Were you popular? No, no, I want it to be.
16:24I want it to be. And then I think, especially when I moved to San Diego, like I didn't know a single person. My first week of school in San Diego, I used to walk around with my lunch in my hands and I would eat while I was walking because I didn't want anybody to see that I was like eating alone. Or eating kebabs and kubaday and Zeresh polo. I literally did a while. I just like, oh, okay, I'll walk around so nobody knows that I'm like eating alone. And so, yeah. So you're not popular. You were short. Actually, if you just go back to like first grade, you barely spoke English. Did that leave a mark on what you wanted to be and do in life?
17:03In other words, did it build grit? One of the things that I ask a lot of my guests on the show who are all like successful CEOs and executives is how do you with your kids, how do you impose grit? I'm sure you think about this. You're not going to introduce them to intentional hardship in ways that just develops grit. Right. So how do you do that? Right. And I think the blessing in disguise for me in hindsight was like, yeah, there was a bunch of random things across how I grew up that created a coat of armor and a fire in my belly that feels like I can't extinguish it. And sometimes that fire burns too hot, you know, but like it's there.
17:53The thing that I got right, even when I was going to college, was I've always tried to do things that I've actually enjoyed to do, because then I could like be great at them. So like even getting into sales, even, you know, my major not choosing science, like I always had this intuition that I should just do the things that gave me energy and that I could do those things very well. Grit to me is being able to do things consistently for a long period of time. And I think the only way you can do that is by doing things that actually give you energy and that you enjoy. And so over time, like hearing about work from my mom, hearing about science and knowing like, I don't want to do science.
18:30Like I've always kind of had a internal compass to follow things that I wanted to do. Is there a defining moment in your life that encapsulates your early childhood? I'll tell you two stories. I'm just like, these are random stories, but these are stories that my dad used to tell me when I was a kid about me. The first is when I was, I think, nine years old, I was in a soccer game. We were in the finals. Last minute we lost and everyone started going to their parents and I just ran. I just like ran into like the forest next door because I was like so mad that we lost. So I think I was definitely always competitive.
19:05And then the other story that my dad tells is we were at a party once and there's a piano and I go and sit up in front of the piano and somebody goes, oh, Juban, I didn't know you know how to play the piano. And I was like, I don't. I just feel like I can figure it out. And like those, like they always tell me those stories because they think it's like, you know, funny and probably who I am. And I think that's probably like, both those things are probably pretty true. You know, I don't know if it's a defining moment, but I think those stories are probably, you could pull those threads all the way to today.
19:35Yeah. So down in San Diego, first job was working at Subway. I heard you got fired. I did get fired. What happened? I was closing up the shop. I love the Subway chocolate chip cookies. story for another time. I put them in the toaster oven. I put them in for 30 seconds. I went to the back. Turns out I put them in for 30 minutes. The cookies caught on fire in the toaster oven. Turns out the toaster oven is like the most expensive thing that Subway has. Close up shop. Next day, the owner comes in and is like, dude, like you broke the toaster oven. Like, you know, you're fired basically. Okay. And I went home and I was like so relieved because I was like, man, that job sucked.
20:15And then my mom was like, get in the car. Get in the car. And do what? Bring your resumes. We're going to go drop them off. And I'm like, where? And she's like, whatever you see. And so we just started driving around San Diego, dropping off resumes. Yeah. Because she's like, you're not getting off that easy. So anyway, that's how I ended up at Vons. I was a bag boy because they were maybe the only ones that would hire me. You know, my first job was bag boy. Was it? Yeah. It teaches you a lot. Yeah. Yeah. No, I actually wasn't even a job. I did it to raise money for my first trip to the US for a competition that I was part of.
20:53But we had to raise money to buy plane tickets, pay for hotels. But I was bagging and people would leave a tip. And I'm not sure if they do this anymore. I don't think they do. But yeah, you could drop a quarter into a little tip jar. And the tips are what paid for your trip? Yeah. Over a course of like two months, I made like$1 ,000 to pay for my plane ticket and hotels. Yeah. That's awesome. No tips. Tips are gone. Tips are gone. No tips. No tips. Too bad. Yeah. I spent the rest of my summer bagging groceries. No tips. No tips. Well, let's fast forward to bracket computing. You talked about first job out of school.
21:27That's what got you to fall in love with startups. Why sales? I was so infatuated with this company that I originally applied for the office manager role. Because I was like, I need to just get - How did you learn about this company? Through a friend, his dad was working there. Okay, and at the time, were you reading TechCrunch and other tech things? Because you're, I'm just thinking about like international relations, anthropology, you go work at, I don't know, IMF or some job in DC, UNESCO. It isn't tech that I'm thinking about as someone who has those majors. Yeah, I think maybe a series of things happened that got me excited.
22:05One was when I spent time in the office, I was like, like startup, like ping pong table, like people, smart people. What year? 2014. Okay, so it's like, you know, the cloud era and mobile and you've got Uber and Airbnb, consumer companies, the rise of consumer companies, but not necessarily the rise of a lot of hot enterprise. No. Maybe like Box was like interesting company at the time, Dropbox. And by the way, like in hindsight, my choice was wrong. Like, like it was, we were too early to the market, but I just fell in love with the people. Then I became convinced that the public cloud was going to be a thing.
22:48Like even then it just became obvious to me that like these early customers that were using AWS, it was like magic to them. Yeah. So I was like, okay, well, like there's probably going to be a thing here. I had no idea it was going to be as big as it was. But I mostly just fell in love with the people and the culture and the startup. And you had a choice, you said, between this and Yelp? Yelp was one of the offers that I got for the SDR job that I sent to them to kind of be like, hey, Yelp will give me a job. Very different company. There were a lot of salespeople at Yelp. There was a kind of a boiler room culture there.
23:18I'm sure you would have learned a lot because a lot of those folks have gone on and done some great things. But yeah, it's quite different. Consumer company versus a cloud computing company. Very different. Very different. I, for some reason, I cannot even explain to you to this day, I became fixated with working at this company. And maybe it was because they kept telling me that I was not ready to go work at that company. Like maybe if I was being honest with myself, just the fact that they told me that I was not a fit and wasn't qualified, made me want to prove to them that I was a fit. And maybe like in retrospect, going and getting all of the other offers was to both prove to them and myself that other people were willing to validate that I was good enough for a role like this at a different company.
24:00Yeah. And maybe that's the driving force behind it. But I just had this fixation that I had to go prove them wrong. Yeah. Well, it turns out Bracket did not find product market fit. When did you feel like, hey, this dog's not going to hunt? So after like a year, it became very obvious that it was just a slog. I had to lay off my team. I was, you know, whatever, 22 years old, like in sitting in a room, telling people with families that they don't have a job. Like it was pretty gnarly. And at that point, it became obvious to me that it was time to do the next thing. I still wanted to be in cloud security because what's funny is even though we tried to build like a hypervisor called the metavisor and like it was such a classic building way too much and falling in love with the technology for the technology sake and not treating the customer as the first class citizen and treating the tech as the first class citizen.
24:52And so anyway, went to another startup with my then boss at the time. I was like rabid to get into like selling. Cause I remember thinking that the AEs, the salespeople, they weren't like working hard enough. And like, I was setting up all the meetings for them just so that they could just like, you know, fly to these meetings and like do these dinners. And I was like, it just felt wrong to me. And I just felt like I could do this better. And you did. So anyway, yeah, I joined Evident. I was whatever, 23. At the time the company had, you said it, like 15 closed deals. My first full quarter there, I closed 16 deals, double the logo count of the company.
25:30And basically at that point became the poster boy for like all things recruiting and hiring. They, I said, Hey, tear up my comp plan. I don't want to actually even be a rep. I want to be a leader. Like I enjoyed being a leader when I was at bracket managing people and the inside sales team. And then I just told my story, every recruit that would come in, I would just tell them like, yeah, this is what happened. And so built that team. And then at whatever, 23 years old, they were like, you're too young to be like leading this size of a team. And I was like, well, now what? And they're like, well, we can, you know, you can go back to this and that.
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26:02And I was like, no way. Like, come on. Like, I feel like I've earned my keep here. And I said, all right, I'll cut you a deal. Make me an enterprise rep. Like the, you know, I thought of that as like the creme de la creme, like go do big deals. I want to do big deals and don't change my comp plan. Keep my, keep my comp the same. Put me in whatever territory you want. But if I succeed, then I want to be rewarded for that. And they were like, all right, fine. And I said, if I don't, you can fire me. Like no, no, no problem. And then I became the top enterprise rep within six months. Then the Palo Alto, like the Palo Alto Networks thing happened, closed the deal with them.
26:40Then they acquired us. And then I go to Palo Alto Networks. That was like the last acquisition of Mark McLaughlin, who's, I love that guy, Like unbelievable. What a treat and honor to be able to now like get to know him through the podcast and become friends with somebody that I used to look up to so much. What a treat. That was the last acquisition that he did. And it was the first acquisition for Palo Alto Networks in the public cloud. They were a firewall company until then. And same conversation, by the way, I get there and they were like, you know, you're, you can't lead like you're whatever.
27:12At that point, I was 25. You can't lead all these people. You know, we, we do things a certain way here. It's like all the things that really like, yeah, ground my gears. Too young. Yeah. Ground my gears. Yeah. How did that, like, how do you turn that feedback, maybe even some resentment into like energy into fuel? Yeah. Well, I think, um, in, in that case, like I just wanted to find an op, I just wanted a chance to prove them wrong. And so it was the same conversation as I had it at Evident going into the enterprise job. I'm like, hey, listen, give me whatever territory and let me build it out.
27:48And if it doesn't work, like fire me. And so they were like, all right, well, we have the central U.S. business, which, by the way, like at the time it was securing public cloud workloads. Nobody was doing anything in public cloud in the central U.S. It was all like on the coasts. Right. I'm like, great. Where is the central U.S.? And they're like anything from Chicago to Texas and in between, you can move there. and I'm like, all right, perfect. I'll go to Chicago. I'd never been to Chicago. I didn't know a single person in Chicago. I moved there in November, which was like, you know, a gnarly time to move to the Midwest.
28:25And yeah, like you said, at the time, the business had 100K of renewals. I built out the central US and within four quarters, we were doing 56 million of ARR. We became the top district in the company. I felt like I had stamped all of the things in sales. Like I had been the IC across all of these different things. And then I got to lead those teams. And then we met. Then we met. And then we met. But you also fell in love with Chicago. I did fall in love with Chicago. And I fell in love with a gal in Chicago. That's right. In Chicago or? In Chicago. Okay. Well, you had this amazing tradition that you told me about in Chicago, where you'd go to the same place every once a week for dinner.
29:05The restaurant's called Bavettes. But that's if you're listening, I've never had a single free meal or anything before. So maybe this is my my golden ticket. No, but the restaurant's called Bavette's and it was a block away from my apartment at the time. And same thing, like when I got there, I just wanted some form of consistency, community, like something that made me feel like this is I'm a part of something. And I like stumble on this steakhouse called Bavette's. It like it's a scene straight out of the Goodfellas, dimly lit jazz music, no white tablecloth, like all the things that I'm like, oh, this is right in my strike zone.
29:46And they have like this long waiting list. And I'm like, put my name down. They call me four hours later, have like a 10 o 'clock dinner. And I sit down and my server, his name is Julio. And I don't know what happened, but I just fell in love with this place. And again, it was like the seed that I just couldn't shake. Like I was like, okay, I'm like now obsessed with this place. I guess that's the deal. After dinner, I told Julio, I'm like, hey, this is going to sound crazy, but I want to come here every week, every Wednesday at 630. I want to have a standing reservation with you in your section at Vivette's.
30:22And he was like, that is crazy. I've never been asked that before. It's like a fancy steakhouse. And he was like, you know, let me go check. He goes and checks. Front desk is like, you know, the next few weeks are crazy. like, cause they book out like a month in advance. Let me see what we can do for the next few weeks. But like, if you're being serious after that, we can have a standing weekly for you. It's like your early version of the podcast. You would have dinner with someone different, I imagine every week and have a conversation. So this podcast thing was happening way before you got to Kleiner Perkins.
30:53It was, it was. Was it different people you'd have? Different people. Oh, by the way, it was the biggest hack for work because everybody found out that I had a Bivets reservation. And so senior leadership that I had no business like hanging out with, always wanted to host meetings, bring clients. And I would always say, sure, but like, you know, it's my reservation, I have to be there. Yeah. You know, and so, so yeah, it was great. Well, let's jump to KP. I think when we interviewed you, you were still living in Chicago, right? Yeah. Yeah. Can I interrupt you for a second? Did the interview go bad?
31:27Like now that I'm thinking about it? Yeah. Like it was not obvious that we should hire you. Were you a no? I was not a no, but I was a question mark. I got thrown off a little bit. By the dudes and the fans. Yeah. Because, you know, like try to show up like. Proper. Proper. But then at the same time, you really vibe with founder energy. Like in, you know, here we work with founders and it is how do you relate to founders? How do you befriend? How do you make them feel like they trust you? Maybe I was thinking a little different. My calculus, I'm very curious to hear what you think, was I just thought like, all right, I've been talking to these folks from Kleiner Perkins for a little while.
32:17It originally started because they were like, maybe you could be the CRO of some of these portfolio companies. Turns out like I wasn't getting the CRO looks of rippling and Figma, you know? And so I was like, all right. Then the conversation changed tone into like, you know, actually like, why don't we figure out a way where you can help our founders with some of this stuff and you can do some of these things. It was very, very nebulous. Like there was no job description. And I remember thinking, all right, the bear case here, which is the most likely, is that I'll probably spend like 18 to 24 months and hopefully do some good work and then find my favorite portfolio company.
33:00Hopefully have built enough goodwill with Mamoon and the rest of the partnership where they would advocate for me. Hopefully built enough goodwill with a founder where they say, yeah, come in. And then go like join them. Yeah, to be honest, we thought the same thing. Okay, cool. So you had the same evaluation. Yeah, like, yeah, this is, who knows where this goes? You know, we're going to bring you on. You have great knowledge of building out sales teams, which is what we need help with for our portfolio. companies. We also have this amazing CIO group that we've had for the last 30 years and making sure we connect the right companies at the right time with these CIOs.
33:35And you are going to help us manage those relationships and make sure the right connections are happening at the right time. And so, yeah, it was a bit of an experiment, but thought that you could do a couple of those things, which is help on the sales front and help on the BD front. And I think actually very quickly you realize like you can't just give the advice. You kind of have to go in a bit more than just give the advice. Can I actually tell you what I found most refreshing when I joined? It was very obvious when I started to work with these founders that the quality was like really high.
34:09And, you know, I've worked with founders before and I had some feel and it was very obvious to me that some of these folks were different, like Arvin. Like some of these folks that like Glean, Arvin Glean. started in this office right here. Right here. Like different. Yeah. Right. And so, you know, so much of that is because for those who are just listening, Arvin is a founder of Glean. Of Glean. Yes. And so much of that is that, you know, like we have this incredible legacy that you and I are kind of standing on the shoulders of the giants that came before us. And that gives us access to work with amazing founders.
34:48And so that was like part one was like, okay, the people here are amazing. And part of that is because we have this rich tradition at Kleiner Perkins, part one. Part two, which I was very refreshed by, was we did not have any of what I felt like were the sacred cows. And that was like, as I underwrote my bowl case, it was like, all right, Mamoun, Ilya, like this new guard has come in. And they're taking the reins of this historic firm. And I was optimistic, but doubtful that maybe there wasn't going to be that many rules. Maybe they were going to let things kind of run for a while. And then we were going to define our own culture, our own sets of traditions, our own sacred cows.
35:40And that was the thing that was like quite amazing because it's very rare to have that combination of tradition, history, amazing entrepreneurs that we get to work with. I never heard, hey, we do this because this is how we've been doing it for the last 50 years. Like I never felt that and I never heard that. And that worked well for me. Yeah, I think there are a few very sacred cows in our business and that have extended, you know, 53 years of us being around. Those sacred cows are the trust you have with founders, the trust you have with your LPs, and then the trust you have with each other as colleagues.
36:24And part of that trust as colleagues is one of our values, as you know, is assume positive intent. Anyone that comes to work over here, we assume that they are doing their best job and the job they've been hired to go do. And you assume that they have positive intentionality in terms of what they're going to do next that is in the purview of their job, which is one of the things that you did, which was start this podcast. I remember you coming to me and say, hey, I'm going to start a podcast. And this is at the peak podcast era of VC in 2020. We meant right before the pandemic, because I think it's when we had our first podcast episode.
36:59I guess now might be peak VC podcast, folks will say. But even at the time - It felt like saturated. It felt saturated. Even at that time, we talked about like, wow, there's so many podcasts. Why have yet another podcast? It wasn't a sacred cow. It was just a, let's try this. Walk us through sort of the ideation of the podcast and why you wanted to have that as another quiver. The podcast was like, I mean, first of all, the story is hilarious. Like when I brought it to you, I mean, skepticism would put it lightly. Like it was like, you know, all the things, right? Like, hey, every firm has a podcast.
37:37Oh, you're like the youngest guy here. You know, you just started. in so many words, like, don't you have anything better to do? You studied anthropology in college. What do you know about tech companies and the history of tech companies? And to interview a bunch of CEOs and CROs. I'm not really sure I trust your ability to articulate quite clearly on a podcast, like the questions you want to ask. There was resistance. Like it was like, it was, I would say, it was a test of conviction. It's like how I would think about it. Like how bad did I actually want it? Totally. Because like you and others were like, come on, basically.
38:10And I remember like licking my wounds that night, like almost embarrassed because I was like, man, maybe that was a bad idea. Like I actually, I think maybe they're right. And I was just talking about it. I remember just talking about it. And then the next day I'm like, you know what? I need to show them. I can't just tell them. Like I need to actually like give them something that they can feel. And so I recorded an episode with my old boss at the time, previous to KP and - First episode? First episode. and I sent it to, I think you and Ilya. And I remember saying, hey, like, I don't feel like I did justice to what I thought this could be.
38:52If I like still have a job here and you all like this, like, let me know. And I think like that was important for you to like feel it. And I think it like went from maybe a lot of skepticism to a little skepticism. I don't think we were like, oh my gosh, we have to go do this right now. But I think it was enough to give me some rope and say like, yeah, go like do 10 episodes. Yeah. I think I remember like first five, you had Jim Herbold from Box. I think you had Bob Frady. Bob Frady. From Slack. Yeah. So you had some really awesome - Hannah Wilson. Hannah Wilson. Yeah. Modern Health, now Nooks.
39:27So you had some greats. Yeah. And the whole point of it, just to be clear, was not that I wanted to have a podcast for podcast sake. It's because I realized that like so much of this job is helping our founders build their teams because like startups are just an accumulation of great people doing hard things for a really long time. And the like key variable is great people. Yeah. And folks like Arvin were asking me like, hey, how do I hire a sales leader? Where are they? Right. What are the things that we should be doing. And I remember reaching a limit where we would run routes together. This is how you should close this deal.
40:09I would kind of give him some thoughts, structuring deals. And then eventually it became very clear, we need somebody in the seats leading sales. Yeah. And here you could actually do it. You could walk down the hall and go see Arvin talk about. That's right. That's right. About deals, right? That's right. But how do you do it as a Monday morning quarterback from a VC firm on Sandhill road, you know, across a bunch of portfolio companies, it was impossible. And what I realized, because I was like interviewing other people that did this job at other firms and frankly, like no shade, but many of them are at the tail end of their career and they go to venture as like kind of a retirement job.
40:47And the good thing about that is that they have like 30 to 40 years of experience where they have the sales leader tree of people, right? Like they've hired all these people that have now gone on to become sales. So they just go and pick the people that they've worked with. And I was like, I do not have that. Right. But I'm still being asked to help our founders with that same problem. And so this was my kind of maybe creative solution to be like, how do I get to know these sales leaders? And I just thought, you know, like there is not a very good platform for them to be able to tell their story authentically.
41:20And so that was the genesis. it worked because I did get to know all these sales leaders intimately. And we did start putting them into our portfolio companies. And so, you know, like at some point we just realized, man, like whatever, it was like 80 episodes in, I've interviewed 80 CROs. I'm like, I know every CRO, like I know every great sales leader in the Valley right now. It was insane. Yeah. So that was the like, that was the Genesis. Yeah. I know it's been incredible to build out our network of CROs and help place a few of them, help place people that work for them. Just all in all, it's been an incredible success.
41:58But you obviously didn't stop there and you built that a whole portfolio operations team here at Kleiner Perkins. Maybe do your best version of the marketing of that team. My disclaimer on the marketing of the team, which you can disagree or agree with me about Kleiner Perkins is I actually think we're quite good at doing the work and we don't really do a lot of talking about the work. Yeah, so now's your chance to market it. So I'll say - Now's our chance to market it. I will say, actually the arc of the podcast resembles a lot of the arc of how the team was built. Meaning like the podcast from episodes one through 80 was CROs, then we did some CMOs, then we did COOs.
42:41And then after like episode 90, it was like Ariana Huffington. And then it was like John Doerr and then Al Gore and then CEOs that used to be CROs. And ever since it's basically only been CEOs. And so like it kind of like our TAM expanded over time. As we started to see success, we kept doubling down on it. And I actually think in many ways, like the story of the operating team here at Kleiner Perkins mirrors, like us seeing early versions of success and then doubling down on it. Like it was just me. And I was helping founders with sales stuff and we talked and we were like, this is working. We should double down on it.
43:18And I'm like, yeah, I agree. You should meet this guy. I've been thinking the same thing. You meet Liam. And then we bring on Liam on the sales side. And then it's like Liam, the guitarist, the bass guitarist, you know, this is like the you're Chris Martin now. We're going to go, let's do the Chris Martin thing. That's right. So, so we bring in Liam. And then on the customer side, like I had, you know, managing this group of 50 of the Fortune 100 CIOs. And I was making a bunch of introductions because of the podcast and because of this. And the portfolio was like getting a lot of use out of it.
43:49And we were like, well, that's working. We should double down on that. And so we brought in Lauren. Our drummer. That's right. And then, and by the way, I tried to hire Lauren, like three different companies. So I guess it took Kleiner Perkins to get her to team up. And then we were like, wow, okay. Like there's like a go-to-market thing here where like we have sales, we have customers. Well, I think there's an opportunity to help our portfolio with a lot of things around marketing and demand gen and how do you build a funnel and what does that look like? And so we hired Suzanne to kind of round out the go-to-market side of the team, right?
44:26Then I would say like mirrors the podcast in many respects, where it was like, all right, we were like rode that for a while. That like was working. I don't know how else to say it. Like it was just really working. Working as defined by founders would tell us all the time, this is magic. I have a lot of other VCs on my cap table, and this is magic. And the reason why go-to-market was such a good wedge for us to help founders most impactfully is because so many of the founders that we work with are technical in nature. And so their experience and biases around product and eng, and so if we can help them fill the gaps on the go-to-market stuff with operators at the primes of their career, not the folks that I used to work with when I would work with other VCs that were at the tail end of their career that had the energy, like you were saying earlier, of a founder or of the people that would be working at these companies.
45:18Like you could actually do something special. Now, in order to do that, you needed to have a firm that had the appetite to bring in people at the primes of their career. Right. So like there was a lot of like shape-shifting that we had to do internally to like be able to do that. And like we had to make a real investment in doing that. the way, like each one of these people is truly in the primes of their careers, which is demonstrated by the number of offers they get every year to come join one of our portfolio companies, which is by design. If they weren't active and so good, they wouldn't get these offers from our portfolio companies or CEOs coming to me and saying, Hey, like I would love to hire Suzanne or I'd love to hire Liam.
45:58Yeah. And would you be upset with me? You can try. I dare them. By the way, I tell them all the time, like your success metric is if CEOs try and hire you. Like that's like the highest compliment that they could they could give you, which is that they want you to lead this function within their organization. And that means they can like see you as a part of their team. That's like the essence of what we're going for. Yeah. So like maybe one more thing is that these are all very senior people were actually doers and ICs here. Just square that for folks. I mean, like, let's just take Suzanne, who was like employee 30 at Miro, spent four years there leading enterprise marketing, had like this giant team, and then joined us.
46:47She has no direct reports. And she is like deeply, deeply in the weeds, like in some cases, like fractionally CMO of some of our companies, like literally running their standing Monday meetings and stuff. And that is like a very rare person that is what I call a dolphin. And a dolphin like goes up in the air and then underwater. And what's happening is like, they can operate in the air at like 10 ,000 feet, very, very strategically with founders. They can start breaching the water at like 5 ,000 feet. And that's like, you know, like all the mid-level stuff. and then they can go all the way underneath the water at a thousand feet and very, very tactically get in the weeds.
47:31And the ability to oscillate back and forth between very, very tactical and very strategic, it's like my love language. Like it's magic. It's like the thing that I always interview for in leaders. It's like the core thing. And it especially is useful in this job because there's such big swings of responsibilities where one founder is like, tell me about this comp plan and what it should look like. And another founder is like, help me architect what a sales or marketing org should look like. And that's like quite a range, you know? And so I would say like, that is like probably some of the magic of these people.
48:08And the people defines the strategy. And we have incredible people that can do these things at all of these different altitudes. Does that answer the question? Yeah, totally. And then maybe just play it out for the rest of the team. Play it out. So then we were like, great, this is working. This is obviously working. I think one of the core insights that we had was going back to the Arvin needing a sales leader thing. In order to help Arvin hire a sales leader, I needed to have like a very nuanced, context-rich understanding of his business. So first I had to be an effective extension of his team as an advisor, which then earned me the right to help him with things like hiring sales leaders and talent recruiting.
48:53And that like embedding yourself into a business to then actually have the context required to do the talent work was like a big shapeshift for us and how we think about these roles. And so the next iteration was great. Let's pair these incredible operators with recruiters that can go in and do all of the things together. Otherwise, you end up looking like every other recruiter and venture firm in the Valley, which is like, go find the fanciest logos because you have no context on their business. And all you want to do is hire the person that's gone from X to Y at these three logos. And, you know, like Glean is a very specific culture.
49:34Figma and Harvey are very specific cultures. And so like what you have done is only one piece of the puzzle, but there's a lot of other things that you have to understand about that business to like effectively put these pieces together. So to make a long story short, that was like the insight that rolled in the talent and recruiting function and embed them within these within these roles. And then we did engineering. Right. So we brought in Tomas. He was like amazing. And so basically, like to to to put a bow on this, like we have created our own like dream early stage executive team that founders can basically omakase into.
50:09And when they need, when they have a pressure point on their business that they need solved, whether it's across hiring, talent, advice, recruiting, somebody to shoulder to cry on, engineering, finance, product, sales, marketing, whatever it is, they can tap into an operator at the prime of their career that feels like an extension of their team across all of these different functions. And so, you know, it took us six years to get to this point, but that's, what we've been building towards. And I think of it as our job as early stage VCs, partner with founders who have incredible vision, passion, and dreams to create really history-making companies is to help them in those early days, really get them on the rails, get that freight train going.
50:58And if we can create as little friction as possible for the the rails that they're on and help them with the hire their first sales rep or be their, their fractional CRO or fractional CMO. There's so much leverage in that for the company and us as investors, because once it's going, then, you know, momentum builds and you become a market leader and then you're anointed to the leader in space and, and things just work so much more smoothly. And candidly, it requires less time and energy from us as companies mature, because at At that point, if a company doesn't run itself and doesn't have key leadership inside the company, you don't want a fractional CMO of a company that's 100 million of ARR.
51:41Totally. You really want to help them when they're at zero, one, two, so that they can push really fast to 100. And I think that's where we really have, I think, done an incredible job. And your team has done that is to really help with those really early innings. And then, you know, you go deep for that first year with companies at that Series A stage. and you get to 10 million and it's like, you know what? Like, I think you got this. You built a team now. They've left the nest. They've left the nest. And so, you know, think about your time with Arvind when the company was zero, one million of ARR and how much time you spent with them at the time versus how much time you spend with them now.
52:17And it's just different, right? And that, because it's working and they've got the internal resources to do everything that we were helping them with early days. Can I connect two random dots? And maybe you disagree with this, but like, I think this take in like conventional wisdom is that venture firms cannot help startups. And I actually generally agree that in most cases, when you surround startups with people that are like at the end of their career, that haven't actually operated in 10, 15 years, that a founder would never hire as the executive in that respective function. Like, yeah, probably not that helpful.
52:58I do think that if you can have people that are an extension of their team that are actually at the primes of their career, I think it's real leverage. I think it's real leverage. And I think hopefully our founders would say the same. I'm really proud of this effort over the last six years under your leadership to really build out the portfolio operations team and provide real results. It's definitely like a important part of what we are able to offer to our companies and is really differentiating. And I know other folks have tried or are trying to replicate what we've done here and they should because it really helps our companies.
53:38And can I tell you why it helps our company? Like, why does it help our business too? Like it helps our companies because I do think we're inflecting outcomes more positively, but also 95 % or more of the entrepreneurs that we partner with come from referrals from other entrepreneurs that we have worked with. And so like, talk about doing the work and not talking about the work. Like they feel that. And I think part of why they say, hopefully I want to work with Kleiner Perkins is because we can help them across a bunch of different areas. Yep. Win. Yep. It's not just the pitch. I think it's, I get to see it in action.
54:15And of course, I'm biased here, but it really has moved the needle for many of our great companies. So you talk about helping entrepreneurs. You have become an entrepreneur and a founder yourself in the last few months. And I reflect back on our one-on-ones and the ants in the pants, the anxiety, anxiousness. There's always a desire to do more. And I probably told you like, yeah, that's cool. Like you want to do more, but the more has to be done in the right place. Like it has to, you know, be applied in your zone of excellence, at least. So you decided to start a company. It's called Roadrunner.
54:53Tell us more about Roadrunner and really more importantly, the why of starting a company. As I was growing up in my sales career, this is the problem that basically haunted me my entire career. The company was legitimately, I don't know if you remember this, almost called Casper because of that. Like it's been the ghost that has been haunting me. And very specifically, what was haunting me was when I was, my team or I were trying to get deals done, whether it was mid-market or enterprise, the underlying software systems would not permit me to do them. And the reason for that is because we have built these custom Frankenstein things on top of Salesforce CPQ and other solutions that just don't work.
55:33The data models do not work. And so I knew that, like I knew that like I was getting dragged through days of back and forth, trying to get the software to work, going back and forth with people internally. Come to Kleiner Perkins, CIO group that we mentioned. Lauren and I on my team started a second CIO group of 35 technology CIOs. CIOs from companies like Netscope and Box and Uber. And over a series of several dinners, I asked them, what is the number one thing that is broken in your company that you are responsible for? And I swear to you, uniformly, all of them said the same thing, which is that they are getting yelled at by their sales leaders because the underlying software that they're trying to use to get deals done does not work.
56:22And the reason it does not work is because pricing models have gone crazy over the last 20 years, where it used to be in your early days of investing, you sell a seat, that seat equals a license, that license equals a person. Okay. Now over the last 20 years, you have hundreds of products, all of these SKUs, some of which are priced as consumption, some of which are priced as, well, it's like, it's gotten crazy. Right. And now you have like open AI, Databricks, Anthropic that all price, you know, it's like a, it's a new era of pricing models that have completely broken the underlying systems. The architecture is completely broken.
56:56It reminds me of, of when we went from on-prem to the public cloud, like when I was at bracket and everyone was like, yeah, you can just like lift and shift this application from on-prem to the public cloud. And then you realize like, oh no, like S3 buckets can just like blow away. You need to refactor this entire architecture from the ground up. And by the way, I think we see that more broadly across many of our portfolio companies, which is like, there needs to be an AI native version of a lot of these products. They have to like rebuild from the ground up. So that's like the tee up. We as a firm get very excited because we're like, great, like pretty obvious.
57:30Like it's very rare that you hear this much pain from this much buying power. Let's go invest in a company, right? So me and a few folks internally like go and investigate this entire space. And we come back and we're like, Nothing. Like there's nothing compelling. All of a sudden GPT 3.5 comes out and we realized, oh, wow, like this is actually a pretty good problem for LLMs. Not dissimilar from our portfolio company, Harvey. Anytime you have structured and unstructured text in nature that the LLM can point to and then reason with and then produce something thoughtful on the other side, that's a good use case for these LLMs.
58:09It's also a good use case like encoding, right? like where there's structured things in nature. And this is a very similar problem. You have price books and discounts and approvals and all these things. Then I come to find out that the gorilla in the room, Salesforce, that probably has 95 % market share in this space, has end of life and stopped supporting their incumbent CPQ solution. So they have now abandoned 8 ,000 customers. And by the way, like all of those customers are calling me being like, Jubin, what's the deal? Like, what do we do? Like, can KP help us find a company that can like fill this void?
58:41because this is like a key business process for us. Then I started to think about like, well, why hasn't anybody done this? And I think the short answer is like technology wasn't there. And this is like a pretty complex go-to-market and distribution problem because there's a lot of hands in the cookie jar. And it's like an upmarket problem where as you get more complexity and volume and reps and SKUs and products, that's where things start to break. And like, just so happens, like that's what I was brought to do at Kleiner Perkins. And that's what I've done my entire career. And it just so happens that I happen to know every CRO and CIO in the industry, because we have two groups of CIOs that I'm responsible of here at the firm.
59:26And I happen to have started a podcast that interviews 80 CROs. And so, you know, like, if we could make this thing work, like we had a very, very unfair reason to win. That's was I think what pushed us over the edge. And then I don't know if you remember this, but I think you and I were like, kind of like, okay, this is like kind of starting to make sense. You know, like this is making sense. And then I went to a wedding in Monterey and I basically didn't leave the house except for the wedding itself. And I spent the weekend vibe coding the initial product. Basically like the product that I as an AE would have wanted.
1:00:07This is like what, four months ago? This is like, yeah, four or five months ago. Yeah. Like, I think June. June, okay. July. And built it. And then I think like maybe the tone internally shifted to like, oh yeah, yeah. Like this, this makes a lot of sense. Is that fair? Like, no, I mean, I think you had a blank check. Okay. Yeah. You actually did tell me that and that meant a lot to me. Yeah. I appreciate that. And I meant that. I appreciate it. So along the way now, you brought on amazing co-founders and you built what I think is an incredible team already in just a few months of from vibe coding to saying, we're going to start this and incubate this here, pairing yourself up with folks who can help make this into reality.
1:00:54Tell us more about your co-founders. So we incorporated the company 13 weeks ago, not that anybody's counting. And we immediately brought on several paid design partners, customers that we're co-developing the solution with. And during that time, I was like, kind of like dating all sorts of technical talent across all oscillations because the core risk is obviously like, I'm not hands-on keyboard. Like I am not an engineer. And AJ and Eugene, former KP fellows, were introduced to me. They had, they're amazing. AJ went to Caltech at 15 years old, met Eugene, his first day of school there. They have been literally roommates ever since, to this day.
1:01:42They went to NASA, built a bunch of the software testing for the Mars rover. AJ went to Robinhood. Eugene went to Meta. They started a company that was an LLM for college students to send their applications and essays, and it would grade them. The business is actually cash flowing. Anyway, they started asking their founder friends, like, what's the thing that's most broken in your company? and lo and behold, CPQ, CPQ, they were like, they, but they didn't put a word on it. They were just like, I don't know, like our sales teams are just yelling at us because like they can't get deals done because like the software just like doesn't work.
1:02:16And they were like, what is that? So they spent a week. Then they got independently excited, met me. And I had like this, like lovable, like this deck, like this, like we had this like thing built out. Right. And it became very obvious to them like, all right, if we're going to do this, like we should probably like do this with Jubin. And it became very obvious to me that if that if I'm going to take this really seriously, these are absolutely the co-founders of Dreams, really. The team is seven about to be nine. You saw a demo last Friday. Pretty good, right? Yeah. Pretty insane how fast that happened.
1:02:51Yeah. Also still inside of KP. We're still, you haven't kicked this out yet. Yeah. Yeah. Taking over the second floor of South Park. Taking over the second floor. Yeah. It's happening. Yeah. Can I give you like one other answer about like your blank check comment? Because we had a lot of conversations behind the scenes of like me. I don't know. Would you describe it as thrashing? Like me feeling the itch to go build. Yeah. I really felt the itch to go build. You asked me at lunch one day, like, why? I think my answer was that starting a company and doing an early stage startup is like the ultimate test of what you're made of.
1:03:38Seeing it in the podcast, seeing it in Kleiner Perkins with our founders, like it's one of the hardest things I've ever seen be done. And after a while, I kept talking to people that did it. You know, I kept seeing it happen. And I think I realized a few things. One was like, that is the most impressive thing that I see somebody doing to push themselves to their potential. Like, man, do you see what you're made of? And then two, most people have no idea what they're doing. Meaning like, it doesn't matter how many companies you've started, every company is unique. And it's like this own thing where like you put one step in front of another and you have to like figure out the problems at hand right in front of you.
1:04:23and that like generally was very exciting to me. Like that gave me a lot of energy and then paired with like this thing that's been haunting me for a while, that conversation stuck with me. Yeah, well, I guess my job is to ask questions and the Socratic method of trying to get people to find their own real answers and why they're doing what they're doing. And now that you're in it, you're doing it. This is, you actually have two jobs. one at Kleiner Perkins and one being the CEO of Roadrunner. Maybe just before we go more into the job of being the CEO now and building a company, CPQ is not the sexiest, maybe we'll start with like, what is CPQ?
1:05:09You described like it was like a hair on fire problem for a lot of folks. But for those uninitiated on this topic, help us understand why it is so interesting and critical as a problem that you want to go solve and make it also your life's work. Because everything that we back at Kleiner Perkins, we're like, hey, how can this be a generational company? How can this company make history in the words that we use here internally? How can Roadrunner make history? The entire life cycle of this business process is from quote, an AE generates a quote to cash, like money in a company. And by the way, like that's kind of the like core competency of any business, which is like you deliver a product.
1:05:51In order to deliver that product, you need like a piece of paper that says, what are you delivering? And in return, you get money, okay? So like that's the like how businesses run. There is an underlying operating system that enables all of that to happen. The beachhead of that operating system is CPQ. The like first part of that process is called configure pricing quote, which is how do you as an account executive put these products together, the discounts that you're doing across a bunch of different SKUs? How do you get those discounts approved inside of the system? That all happens in very, very, very old and bad software today, okay?
1:06:31And so that's like what we're solving first. There's a series of other things that we want to go solve within the quote to cash bucket, but we're solving that thing first. And we think it's like pretty important. And then let's bring in AI, okay? because we're not backing too many things that are not using the powers of LLMs and AI today. And you said that this is actually a particularly useful application of LLMs and AI. Tell us more about that. I don't know if you agree with this, but it does feel like a moment in time where AI seems to be the panacea for everything. Like we see a lot of companies that are applying AI to things that I have my own sets of skepticism about because it's a amazing technology shift and like people are just excited.
1:07:13In this case, imagine a world where if you're a customer, every quote that goes through Roadrunner has a series of tags that are associated with that quote. And so an account executive in natural language can say, this is what I want. They can say it, they can type it, whatever it is. And the system will basically say, you know, what you want to do, we have done a deal like that before. You should structure it just like this. And by the way, just like this is perfect for their comp plan. It maximizes their commission. It's perfect for the business. It creates a set of approvals that instantly get done with a bunch of business intelligence around it.
1:07:54And today that process is, and has been since I started in sales, I get on the phone, I call deals desk, I call rev ops, I call finance. Hey, here's what we're thinking. We negotiate back and forth or AE calls one of their friends. that just did a deal like this. Hey, how did you put that deal together? All of that should be LLMs that basically become a central nervous system, like an omniscient central nervous system that can just tell you right when you say it exactly how to structure the deal in exactly that way and then be able to on the fly give you all of the benchmarking around the discounts to get these things approved very quickly so that, and this is the tagline of the company, we can put revenue back in motion because right now it is stuck.
1:08:43And so if you fully play out the mission of the company, well, actually, you don't believe in mission statements. Maybe just pause there for a second. Okay. Why? Okay, okay. This is like maybe an annoying hot take, but there are a lot of companies in Silicon Valley that make their mission broader than it needs to be. And it implies like they're doing something. some of our portfolio companies, like let's just say Modern Health or Watershed are like right in the slipstream of trying to solve mental health crises and global warming and climate change. And I'm like, yes, that is a serious mission that you are solving.
1:09:27But like, we're not doing, like we're not solving mental health. You know what I mean? Like we are solving a very important problem for a specific group of people that if we solve those problems well in perpetuity, then we earn the right to go build a big company. And that is a mission that I get very excited about, which is solving enough problems that are meaty enough that we earn the right to build a big company. And why do I think building a big company is amazing? It's because growing up, startups changed my life. Like it was literally the number one thing that changed my life. It gave me more money than I ever thought I would make.
1:10:06It gave me jobs and responsibilities that I never thought I deserved. It gave me an access to a community that I basically craved my entire life. And as they grow, you just keep putting people in these positions to literally change their life. And that is a mission that I get excited about. You know, CPQ is something that is important, but I'm not going to make it, I'm not going to pretend like it's something it's not. I'm particularly excited because I get to work with you on this now. and it's really fun to see your co-founders and your team at KP building. The energy is palpable and it's great to just see stuff getting built at Kleiner Perkins.
1:10:44Are you hiring? We are hiring. If you go to our website right now, roadrunner.ai, you will probably get the feeling that we are solving for one very specific thing, which is not customer demand. We have more of that than we know what to do with, which is not venture capital dollars. It is purely to humanize the people behind the company. because so much of my evaluation criteria when I was deciding where I wanted to go work was the people. And so there's fun interviews where everybody talks about what they're working on and who they are. And so we are hiring. The number one bottleneck of this company is today and I suspect will remain for several, several years, engineering, great, great engineering talent.
1:11:25Our roadmap is being dragged out of us right now, quite literally. And so we are hiring. It is in San Francisco. I think by the time you hear this, Mamoun will have probably kicked me out of the Kleiner Perkins office. And so we will probably be downtown in San Francisco or South Park or something, but we are hiring and we're in San Francisco. You know, I'm a softie man. You know how long Glean was here. They were here for 18 months. Yeah. And like 20 people. 20 people. Cool. And then what does grip mean to you? Yeah. You'd think that after like whatever, 270 times of asking this question, I would have like some beautifully prosaic answer.
1:12:02Angela Duckworth's definition of passion plus perseverance over a sustained period of time. Grit to me is doing something for a very long time, come hell or high water. And like even this podcast, like there's a lot of reasons why I wanted to stop it. And, you know, 99.9 % of podcasts never make it past 10 episodes. And it's because they just cannot stick with it. And so for me, it is putting myself in places, whether it's Roadrunner, whether it's my role at Kleiner Perkins, whether it's this podcast where I genuinely feel like I can do this for a sustained period of time. That's great. So the podcast is not going away.
1:12:44So, okay. So the podcast is not going away. We will likely modulate it down. It used to be biweekly, then it became weekly. It'll probably become biweekly again. The thing that I am most excited about in this journey of working together is that I do believe you're the longest term thinker that I've ever met. I mean that. I have never met somebody as patient as you. In the spirit of yin and yang, I may be the most impatient person alive. And so I thought it was really important to do this inside the firm and with you in a way that hopefully represents us well and is a partner for us, I think can help us go the distance.
1:13:24Well, I look forward to the decade plus journey ahead. That's at least as long as some of these great companies take to get built. So we've got a lot of time ahead of us working together. That's right. It's really a joy and really an honor to partner up with you. Appreciate it, man.
1:14:03We'll see you next time.
From the publisher
What does it take to go from advising founders to becoming one?
On this week’s special Reverse Grit episode, we flip the script and put our Grit podcast host Joubin Mirzadegan in the guest seat.
Joubin recently founded Roadrunner, where he is now co-founder & CEO. Roadrunner is building an AI‑native CPQ to modernize the quote‑to‑cash stack, drawing on years of conversations he’s had with enterprise revenue leaders.
Stepping into the host role, Mamoon Hamid joins Joubin to talk about his transition from sales leader to founder, how Roadrunner came together, and why it became our first incubation since Glean.
Roadrunner is hiring! Check them out: https://www.roadrunner.ai/
Guest: Joubin Mirzadegan, Partner, Kleiner Perkins
Connect with Mamoon
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