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The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures

56m 6s

The First Sales Hire Mistake That Sinks Startups w/ Rafa Jara-Simkin, Partner @ Theory Ventures

In this podcast episode, Rafa Jarasimkin shares insights from his extensive career in sales and venture capital. He began at Looker during its early days, growing from a 25-person company to a 1,000-employee organization before its acquisition by Google. His experience selling to developers taught him that authenticity is paramount—buyers in technical audiences reject anything resembling a sales pitch, requiring sellers to genuinely empathize and engage with their challenges. After Looker, he joined Monte Carlo and later transitioned to Theory Ventures, where he advises portfolio companies on go-to-market strategies. Jarasimkin identifies common mistakes founders make, particularly hiring sales teams prematurely without evidence of product-market fit or repeatable pipeline. He emphasizes that salespeople don't solve pipeline problems; marketing and brand-building must occur simultaneously. He also discusses the evolving AI landscape, noting how open-source models like GLM and Kimi are disrupting frontier labs by offering comparable performance at drastically lower costs, forcing enterprise buyers to scrutinize vendors' margin sustainability. His advice for hiring sales leaders is to seek hungry, hands-on managers rather than pedigreed executives accustomed to large teams. He also highlights the importance of niche application-layer solutions that require domain expertise, which AI giants are unlikely to replicate. Finally, Jarasimkin touches on executive coaching, emphasizing that most challenges are interpersonal and rooted in psychology, and he encourages creative, fun outreach tactics to stand out in crowded markets.

Transcription

13336 Words, 70573 Characters

English
There's just no tolerance for any BS or any sales pitch, you just need to actually empathize and be curious and passionate about what they're doing and what they're going through. It really matters even more when you're selling to developers than these types of audiences, because they want anything to do with the sounds like a marketing or sales pitch or anything like that. Just wrapped a great conversation with Rafa Jarasimkin. We got into a couple topics where founders are getting early stage and hiring wrong. You go and hire four people in one quarter with like, you don't have any evidence that you have the multiplier and there's not even really repeatability or clear product market fit or pull yet. That's just kind of a disaster waiting to happen. It's like it sucks for everybody. We're the most common combos he's having with early stage founders. I think that a lot of founders just don't understand how marketing and brand works. I built something amazing. All we have to do is go talk to the people that I built it for and then they're going to be like, wow, this is amazing and they're going to want to buy it. But that's not how it works because they're in a sea of like thousands of other tools that all say the AI, this, that and whatever. And they're like, I don't know what you are. And I'm busy. And so this is like default as no. And a lot of topics that touch on the intersection of AI, start ups and sales. All these new models, you've heard of like GLM and like Kimmy that basically like as good as like Claude Fable. It's freaking out like Dario and Sam Altman. They're like, you know, trying to talk to the US government saying, oh, I've got to cut off these Chinese models because it's threatening to their business. I hope you enjoy it and now on the episode. Welcome to the crew podcast where we have conversations with the top go-to-market leaders at AI Natives and SaaS startups. I'm Chris Bolescheris, co-founder of crew. I'll go to market recruiting media and investing firm, helping seed through series D AI Natives grow now on the episode. This episode is brought to you by parallel parallels where AI agents find answers. They've indexed the web from the ground up for AI specifically so agents can get accurate, low latency, token efficient web data. They power agents at the fastest growing AI native companies and Fortune 500s. And if you sell for living, most of the people listening do, go to market engineers use parallel to run real-time monitors on their accounts, catching funding rounds, exact changes, and products launches as they happen in real-time, and automate account research and enrichment at scale. Get started for free at parallel.ai. Big thanks to our sponsor, Attention. Sellers were hired to sell not to fill in the CRM. Attention records and understands every sales call that automatically updates your CRM, sends follow-ups, and scores reps against frameworks like medic, bant, or your own custom methodology. Next best actions are proactively generated from there. You get a clean pipeline, coaching on every call, and forecasting you can actually trust without asking reps for more admin. Turn your call recordings into a GTM operating layer with attention. Try them today at attention.com. Raf, it's great to have you on me. I'm like making my rounds around that dinner we did at. It was a foreign cinema, like almost a year ago now. Yeah, it was good. You and Tom, and we're having him on again. Yeah, I totally got dinner with him last night. I know you were with him as well. He's just like ripping on jokes all night. Just it was so funny. Yeah, I could just listen to that guy talk for like two and a half hours. I know you and I were chatting a little bit of getting on something like this. There's like a couple of different profiles of people for like this pod that we want to have on. There's like the person who was at like the Kyle Parrish, the world in a sense. Well, no, he's in VC, but like had a big run and like a SaaS company and then hasn't been doing AI company just yet. And then there's the folks that are active in operators at AI and natives. And then there's like the VC folks with a, it was like 10 on my list of that have former GTM backgrounds. You're one of them. So I think for this it'll be interesting to hear a little more like what you're hearing from your port codes. You can make some of my LinkedIn posts. I know you're commenting on kind of hustle pushing a hustle culture. But before you do that, like big, you know, big, rounded looker, which was like a GTM off you for sure back in the 2010s. And then I've been in VC now for three years at theory ventures. But why don't you give the audience a quick look just a little background of of your own up in sales and then now in VC. Yeah. So I got into sales sort of unintentionally. I was like graduated college SF state. I wanted to be an economist originally. And then I realized like, I don't want to do that at all. And then everybody's wearing hoodies, making money, you know, tech. So I was like, I guess I got to try this thing. So I worked as a data analyst for a year or something like that first. Bootstrap startup for the CEO building a bunch of like reports and charts and like excel. Basically, it was like really simple stuff pricing model. It was fun. It was really good. But I realized like, I don't want to be stuck behind a screen all day. Like this is going to drive me crazy. I'm like, way too social. So how did the transition work? I think there was a small like really transactional inbound team that they were running. It was like kind of like pick up and close in the same call stuff. And the leader at the time was like really not working out in a big way. You didn't have any replacement, but they knew working with me and like they kind of just took a bet on me to run the team. So I got promoted to a manager of a job that I hadn't even been at IC for at first. And I did that for like half a year. And it was actually like really good a good learning experience. And that was this weird lateral transition into like getting into sales and tech that I wasn't expecting. But they, you know, they took a bet on me and I was working. But then I my first, what I would consider like my first real sales job was that looker. I joined the end of 2013. They were like 25 something people small still wasn't even attending on that move. But I was like living in San Francisco going down to home to Santa Cruz to surf and see like my family and my mom and whatnot. And I was just reading a paper. There's like no tech companies down there at the time. Still there's like very few. And it was like local tech company raises a million some dollars from Red Point Ventures. And I was like, what the heck? I must be wrong. There's no tech companies here. And so I started just, you know, started exploring that more and then snuck in the back door through this like little user, like meet and greet thing they were running in San Francisco. And they thought I was going to be a customer. So I was kind of playing that part because they were choosing me. I got to meet the VP sales who was there. All kinds of people. And then I called the rep at the time who's like still friend of mine. That's got Jeff Garcia. And I was like, Hey, buddy, listen, like thank you so much for inviting me. I love meeting everybody. I'm going to tell you some bad news and then some news. Well, maybe good. I was like bad news. Like we're not going to buy from you. Like unfortunately, I was just like never going to pay for this stuff. I think it's amazing. No, and I would love to work with you guys. And he's like, it's kind of expecting that. And so then I then I got to interview there. And actually the head of sales, Lambert, him and that would be my mentor for a long time. He wouldn't talk to me for a while because it's like no go zone because I was like a customer. I was a prospect in pipeline, turning into a candidate. And then eventually he just was like, I fuck it. I'll just talk this guy clearly. I don't buy. Like, I'm not a real deal. So that's kind of how I like flopped into sales. And then from there, the rest of history, I can go into detail if you want about look here. But yeah. Yeah. It's awesome. You were there to 25th employee, roughly, were you there? Yeah, something like that. Were they 20 and Santa Cruz? Yeah. Okay. I put it to Santa Cruz the whole time. Not many of you that are. Google still has a office down there. Yeah. Yeah. Interesting. Yeah. And your big surfer, it sounds like from that story. I wouldn't say big, but yeah, like sort of off and on to town. Yeah. Yeah. Yeah. And the, yeah. Like, look, I feel like I heard through the grapevine. I remember when I was at Salesforce, we had a couple of folks like I believe Matt Glenn went there before the acquisition. Oh, yeah. Totally. Yeah. I actually golfed with him a few weeks ago. Yeah. Matt Glenn, he was on my team. Yeah. Yeah. And awesome, dude. And I just remember a lot of really sharp people that were going there. Yeah. She seemed like incredible. Maybe we can dive into a little bit. But like, okay. So you have this run at Looker. You also are Monte Carlo. I guess under like Jordan. Like Jordan. Yeah. So you have a, what was this? Six year run, seven year run at Looker. I see into leadership. Tell us a bit more. Like, how would you describe the Looker sales culture? I feel like I was hearing a lot of rumblings of it being like, you know, a town hub and like, tell us more about that run there. And like, maybe some learnings you took away. Yeah. Man, that could be a whole novel. You know, so I'm trying to summarize as best I can. I mean, again, I was there for six, six years before that acquisition my Google. And then I was there, like, within Google for almost years after that. And every year, the company was just exploding. And so like, it'll look like a new company every quarter. And that's like kind of not an exaggeration. Like processes change, people change. You're interviewing all the time. You're having to like, redo positioning what you're doing, like the motion. I mean, there's obviously like, repeatability was getting established. But we were adding new stuff all the time. And so you're just constantly learning and going with the flow. So the first year I was a rep and I just kind of dialed in my like sales rep fundamental skills in Santa Cruz as an IC. And then that was 2014, 2015. I moved to New York. Originally, it was just going to be like a one year stint to help out with like, training some reps there and I come back. But I just love New York City. It wasn't expecting too as much. And then I stayed there for a long time. I started building out the sales team there. And so like every quarter, I think I started first years out there, like blew up my quarter of the beginning of the year. It was like running around from office to office. I had like a killer territory and all the startups in New York City. And then by the end of that middle of that year, I got the promotion to like lead a team. I think I like eggs of the year with like five or six reps. Two or three, well, I think like four of those people ended up becoming managers over time, you know, fast forward, you know, four more, five more years in New York. There was like, you know, several mid four managers under me and like, you know, maybe 30 something 40 reps rolling up to them. And the company went from again, I joined at 25 moved to New York. We were about a hundred and then Google acquisition around a thousand employees. So, you know, to try to summarize what I learned is like kind of impossible because this like everything from leadership skills to sales skills to how do you actually like forecast and navigate the like explosion of a company that's like on that path. So many personal things. I mean, it's just it was incredible, right? Like I, you know, it was a lot of work. It was really good. All right, to 25 to a thousand employees. What was like the revenue when you joined in an exited roughly? Like, what was that round? It's a good question. I think it was around, it's like somewhere like around a million when I joined. It was really pretty low. And I think we exited somewhere over a hundred. Oh, awesome. So, yeah, that's like the run that I mean, the SaaS era. That was great. You're like, "Do you need to get $100 here?" Well, there was a tweet that was like, "500's the new $100 million," or something like that, of course. - I think a lot of that stuff is a little overblown. I'm like, "Yeah, yeah, yeah." - It might miss my, like, maybe a candidate, 'cause we're experiencing this, like, intense, like, call it a bubble or what you want, but it's like, "Hey, I just hit the market." So, clearly, there's just so much money coming in and these, like, numbers are getting insane. But there's gonna be, my expectation is there'll be an equilibrium at some point. In prices, we'll adjust, apply it a man to justice to how markets work. Nobody was expecting what was gonna hit recently. And so, that's why you're seeing these, like, reps and teams that have these quotas and these numbers that are freaking insane. And that'll probably keep happening, but it's not gonna keep happening forever. - Yeah. - It just doesn't, like, to me, like, doesn't make economic sense why that would keep happening. - Yeah, you know what's funny? We just, I don't know. It's really interesting. Like, we don't know what the limit is on this. So, I'll give you an example of a couple of years ago, I was interviewed and I didn't throw up, I got an $18 million valuation. And guess what a lot of my friends said. You idiot. You're gonna make no money if you do that. But, and I know Anthropics, like, the edge case, but it is, now I wouldn't have probably got it, just to be clear, even though I backed out when we ended up starting to launch crew, but still, it's just like, we don't know what some of these limits are. Everyone keeps saying, like, and eventually it will come down from it. - Yeah, yeah. - I'm wondering what that'll be. - It doesn't matter. - So, great around, I mean, this is like the around, like, a lot of people like want one that are out. You know where I also got word of looker? It was, bunch of my friends started going to retool. - Yeah. - And retool was pushing a lot of looker people. - Yeah, totally, yeah. - Where else did the looker mafia go do? - They went to a lot of the data companies, like a DT or something. - Yeah, DBT was a big one. You know, some group of Domani Carlo for a little bit. You know, a lot of them are now at Omni, which is like, looker too. They probably hate that, but you know, basically it's just like a way better looker. Yeah, I'm probably missing some data bricks, et cetera. - Yep. - They were already a little big at that point, but yeah, any of these, like, data team focused startups that like hire the same kind of caliber and type of person. I mean, I think one learning to share was like, hiring people, it's basically like hiring people that are like developer focused, very friendly, easy, disarming, want to geek out with people that you're, you know, like actually care about the technology as if you're a buyer almost and want to build with it and learn with it. I'll also say like, I'm gonna credit at least half if not more than half of our success in sales, the sales engineering team at looker, honestly. They were just incredibly good. They were just the partners on every single deal. They would get into the weeds with our champions. They would make the champions love us and then not that it's like layups or the sales team, we still have to do a lot of hard work and stuff, but like without that team, there's absolutely no way we would have done that. But a lot of the reps saw how that worked and they learned how to partner with sales engineers in a way that's extremely effective for like buyers at a developer audience at a data audience or whatever. So that was like a big kind of learning for, I think, everybody that came up in that in those years. How do you view those to be a different sort of persona? - As a seller. - Yeah, that's a good question. One thing that worries me, it's hard for me to answer is I've only sold the developers at a data analyst. So I've been pitched things as an app layer buyer technically and like on the sales side. I think naturally I and I'm imagining other go-to-market folks you're selling to have more of like a patience and like a respect to certain degree and like a sort of like social resonance with like sellers that if you're selling to developers or engineers, they don't talk to you a lot of times. There's no, like I don't wanna go through you or rather just download the thing, like why am I talking to you? So you're immediately going through a barrier of trust. And so the ability to disarm and the way that you're mentality and your mindset needs to be often, needs to be different. Particularly if you actually have to build champions at like an IC level. If you're selling like VPN engineering or somebody higher up, they're kind of more used to it. Like it's actually easier in some ways in that way, but you're trying to like disarm like a kind of pessimistic hole poking like developer audience. That takes a really specific skill set. Not every seller to like an app layer audience is gonna have. - I've learned that it's important to match your energy with that sort of a buyer too. You don't wanna come in like two salesy. - Totally. - Not at all actually. - Yeah, yeah. - What does that mean? Like, okay, I don't wanna be too salesy. I think the way I define it after like many learnings and then eventually selling to developers at Metronome from being more of an app layer seller was, I'm more of a high energy guy. I sold like a lot of sales and marketing people early in my career where it's very like vision casting and it's like a lot of like just raw raw stake data. - Totally. - And. - None of that works. - Yeah, yeah, yeah. You have to just like just match it. And sometimes you would get like a very friendly developer and you know, put it back, you know, flag it back up, but it's like most of the time it was just like, hey, meet them where they're at and then like. - Yeah, I mean, I think, you know, people have probably different responses. The way I think about it is there's just no tolerance for any BS or any sales pit. You just need to actually empathize and be curious and passionate about what they're doing and what they're going through. - Yeah. - Great. And I think that applies to like sales of anything anywhere, but it really matters even more when you're selling to developers than these types of audiences. Because they just, they want anything to do with the sounds like a marketing or sales bitch or anything like that. But if you are the type of person that has the mindset that like listen to the end of the day, this is somebody that is like trying to solve a problem, or they're not going to learn if they have a problem. And I want to do them a service. And I want to help them evaluate that. I want to help, you know, I'm going to get curious. I'm actually passionate and interested in what they're doing day to day. They don't need to buy from me. I'm not, Ego's not going to get it. But I don't have my, I'm not going to close this deal or whatever. I just want to like learn about what they're doing. I kind of geek out with them. And if that's not your mentality and that's just not who you are, you're not going to really do well in this types of jobs. In my experience, unless it's really a top-down sales thing. So again, there's some like developer tools or technical audience tools that are really top-down motions where you're really talking to like director VPs often and you're not rarely having to go down in the weeds. I think it's rare. But like those ones, you could probably more get away with not being as disarming. But if you're having to build champions again at like engineer level, you need to really just like geek out like a homie with them. Yeah. They're just not going to want to talk to you. It's this concept to what I've seen is like, there's somewhat of a blank, there's a blank or canvas in the sense of like they're trying to build every use case still a little bit different versus like if you sell zen desk or I sold the service cloud and sales for service cloud. Yeah. It's a managed package of sorts. It's like, hey, there's like specific guardrails that if you do X, it will do Y. And I think that ambiguity allines to people who, honestly, you can't be intellectually curious in the app cell. There's plenty of my friends who are at those that especially like AI native companies. But in the developer cell, it was always just so ambiguity. There was a lot of ambiguity with what it is they were trying to build. And because of that, you had to problem solve. And I think for a lot of people, that's kind of why they like the developer sound. On top of that, I think that like in the south-- We're interesting. Yeah, well, whatever, yeah, it's interesting in that way. I found it to be. Yeah, I agree with that. It took me like too long to-- I also think that it's kind of a cheat code in the sense. I almost feel like a lot of my friends went into it because it naturally, a lot of times would have a PLG motion and call space. It's just easier. It's like, of course, if you're just trying to top down brute force, sometimes in the market, which we'll get into some of the mistakes that you hear founders making or at least some like advice that maybe you would do. But so after like, OK, you have the run that everybody wants. The 25 to 1,000 employees, the 1 to 100 mill, when did you-- was it just like, OK, we got acquired now? I got to go back to doing it. When was it like, hey, I need to start looking and like, how did you end up at Monte Carlo? Yeah, so we got acquired by Google. I was pretty burned out at the time, to be honest. And I was just like, I need a freaking break. I've just been like, you know, burning the candle at both ends for many years. So I moved into a less stressful role but that I was still learning in, which was an IC strategic account rep role. So I had like five accounts in media or something whatever my patch was. And I was just piggybacking on the key account directors at Google Cloud, who were like, you know, had these hundreds of millions of dollars budget that they were renewing. And, you know, I went in there to just learn that. And then I left to go to Monte Carlo after work. But that was really like-- it was a really good process to see how these bigger deals get formed and go in meeting the, you know, CIO CDOs at Verizon, for example, closes the Hey Figure Deal there, which is awesome. And I just wasn't even expecting that. I like rolled all my dice on one account and went deep in and it worked. So that was a good learning experience. But I always knew I was going to leave. And I was like, I'm going to do this to learn the strap kind of bigger enterprise larger deal motion. And I need to get out of here. So I was a little checked out. I was even talking to my boss at the time. He was like, dude, you don't want to be here anymore. I know. So I talked to Tomas early, who's, you know, a founder at theory. And he told me, you're a startup guy. Like, you're not going to want to be at Google. Come work at some of the portfolio companies that you want to bring me into other companies. Actually, I met Bart and Lee early, like, right when I joined Google before Jordan or any of those people were there. I think there were like four people. And Bart was like, really interested in meeting me. He's like, oh, maybe come here, head of sales, whatever. And I was like, Bart, thank you so much. I appreciate that you're interested in talking, I'm going to be honest, like, I need a little bit of a break. Let's talk in like a year or two. But I'm stoked for you. Stoked you on the founder journey, you got fun. And then when I started to actually open the doors and start looking, I hit up Tomas. And, you know, he was introduced to me some other companies I was meeting other founders. And then I think, I forgot who was. Either Bart Jordan reached directly out to me to like run their mid market teams. I think it was a regional role. And I was like, oh, cool, Jordan, you got the job that I was going to go for. I was like, good job. No, I'm cool. You already took the job. And he's like, no, but there's another job. I'm like, I don't want that job. And then, and I was just like, this guy seemed great. But I was like, I'm going to go be a head of sales somewhere. Like, I know I can do it. All my mentors are like, you can do it. Cool. So I'm meeting these other founders. They're kind of trying to cord me. I'm a little blowing them off. And I'm like, hey, go meet my brother. And because my brother is a killer, a kind executive enterprise kind of. So he went over there and he was in interviews. And then he ended up actually joining Monte Carlo. Oh, no way. So your brother joined Monte Carlo. He joined Monte Carlo while they were trying to like kind of poach me when I was like, I don't know. And I was meeting this guy and then it'll look at it. And the funny thing. The funny thing is that he ended up joining and bars talking to me and Jordan is talking to me more and to meet some other people. I'm kind of keeping my arms distance, but my brother joins and I'm like, "Oh, fuck, man. That's my brother's there." And then some other of our looker friends went over there. And then this was like, my heart was like, "Oh, my family's over there." I said, "I really want to go over there." Plus, it was a great company to join regardless of the title and Jordan seemed great and bar and everything like that. So that was kind of just a funny way that I sort of got into that company. And it was a great run. It was different motion. It was much more topstown. It was selling a new category. The process that I like kind of absorbed and got educated on from Jordan that came from segment, like the kind of standard med pick, command of the message stuff, forced management stuff. That was great, which was different from what we did at looker, but like really complimentary and get a different angle. So learned a bunch there and that was a good one. So you're there for almost two years. It sounds like you didn't mean to get into VC. Obviously, you had a relationship with Tomas, so you're operating. It sounds like, yeah, I want to keep growing in a revenue executive type of role. I think a lot of people that are listening do app goals of angel investing or getting into VC. How did you actually get into the VC track? Yes. I think after Google acquired this, I started getting introduced to some founders through people in my network to do some light advising. I don't know what the hell I was doing, but I was like, sure, so I met some founders and I started learning that a little bit. I was like one or two advising gigs I would do here and there just on the side, maybe invested in angel checks at a few companies. Most of that didn't go anywhere. Some of them go okay, but I had a little bit of that experience, but I wasn't seeking to go do that full time or at a VC. It just wasn't really coming up on a rate. I wasn't sometimes interested in. Then after Monte Carlo, something that I learned for myself, this was a personal thing, was I really felt like I was in my element and loved leading teams in person. When I was in New York City and like every day on the floor, ringing the bell, it was high-fiving people, like in the meetings, clapping hands, celebrating stuff, going on walks, a mass and square park. It was just like the glory days. There was something about remote environments that really killed the vibe for me. It was just like 30 zoom squares trying to feel passionate. It just doesn't work for my system in that same way. Then I was like, okay, I had moved to Santa Cruz. This is like a separate personal thing in my partner and I at the time were pretty locked in there. Once things opened up back up after COVID, there was an option to go move back up to San Francisco or wherever I wanted to go into a city to build it for turn-to-office, like in-person culture, but it wasn't the right timing for me. It was like, what are my options now? I'm like totally changed careers. I could keep doing this remote, but it wasn't really feeling inspiring. I did love the one-on-one stuff, though. Right now, it's way cooler that we're in person, but this would be diluted if it was on a phone caller over Zoom, but it's not nearly as diluted as a group call over Zoom. It's still pretty good. I really liked the one-on-one coaching mentorship, advising stuff, even remotely. It's like, well, what kind of job is that? It's either advising or coaching. I went through executive coaching program at Berkeley, and I started opening up a little practice, and I really just started getting that going. It was actually really fulfilling and fun. I called Tomaz, and I said, "Hey, you've always been a mentor of mine. Thank you for the opportunity." It's just a heads-up because I knew he was probably going to want the place to meet one of his portfolio companies. I'm not looking for my next head of sales role right now. At least, I'm just trying this executive coaching advising thing. If you have any founders in your portfolio or senior leaders that could benefit from that, he's like, "Oh, I think you'd be great to that, but I just started my own VC. Do you want to come and help me?" He just plopped it on my plate. It's funny. I've mentioned this to people who come and interview at Theory Ventures. I love Tomaz so much. This guy is so brilliant, such a lovable human. If he opened up a restaurant, I'd be like, "Gain." It wasn't about VC. I just really connected with this guy. We're like friends. I was like, "Oh, my God. It doesn't matter what type of role it is, how long it's going to be before I have to say yes." He's like, "We'll make it half-time. You can do your coaching thing on the side and then once you have your coaching thing, that takes off. You can rotate out." EIR, executive and residence. That was a plan originally. It was kind of roll up sleeves and do whatever the business needed. I was starting with customer community stuff and then maybe some light advising. They only did a few investments at the time. A couple seed rounds, maybe one a round. There wasn't a whole lot there. Within four to six months or so, I started getting more and more involved with the founders and what they were doing and go to market and sales and how's it going, et cetera. I was mostly focused on our customer community at the beginning. Looking under the cover, looking under the rug, it was very clear that there was a lot that was needed there. I started leaning a lot more. Tom, I need to be focused on this. We did more investments. I got more involved with the founders. For the last few years now, it's just been that. That's great. I've heard him. I went to dinner with him last year with you guys, but he had a lot of podcasting. This is a genuine guy and I would echo that. You're advising quite a few companies now. It's been there almost three years now with theory. I'm very interested in the mistakes that you're seeing or what are the maybe misguided advice that founders are coming in and getting from a lot of different sources and all that. Two or three things that are most top of mind for founders that they're engaging you on to help them solve. Yeah, I mean, it's usually all the stuff you think of like building out the initial sales team. When you hire first rep, when you hire her first set head of sales, some mistakes to avoid there. What does initial team, what are the partners they need and that team look like? How do we know that we're, how are we forecasting accurately? Do we have enough pipeline? How do we know we have enough pipeline? What does a qualified deal even mean? It's just a lot of like kind of junior sales rep type stuff because they're new to it. Then wanting to make sure they're aggressive with the plan, but not like hiring too aggressively and making mistakes. Those are the flavors of things that it always comes down to and then helping them diagnose like where the problem is. All right, y'all quick break. If you're getting value from this, do me a favor and hit the follow button on YouTube, Spotify, and Apple. It helps way more than you think now back to the episode. What do you see as the most common mistakes maybe then? The founders are coming to you with that they've already made it than they're coming to you with. Maybe advice that you say, oh, they're getting this, but I come in and constantly say like, hey, think about this way like anything like that. I mean, yeah, it's stuff you've heard before. It's like wrong hires and hires are made on pedigree or like there's somebody's network. You've heard great things. Oh, they were the best rep. So and so that company that worked out was great. They blew their quota out. Cool. You know, founder doesn't, you know, they haven't hired last salespeople before. They're just like, sounds great. They meet them. The person's the salesperson. They seem really great in the call. They hire them. Some's not working out. Them just not knowing what to do to really go investigate and inspect whether somebody's really ready for the job that early, whether it's right person, whether they still have like fire in the belly to be hungry to actually obitiously like crush it or not, whether they're even the right fit for the market. They're selling it to you. There's just like things that they're just not going to know. So there's a mistakes often that like, I help them come and kind of clean up. Maybe when we're first investing if there's those are being made. And then I think thinking that hiring salespeople is going to solve your pipeline. And you've mentioned this many times on like podcasts and stuffy roads. It's like it's just it keeps happening. Shout it from the rooftops. Yeah. Exactly. Investors and founders and everybody at Con this trap where it's like, okay, I got like I empathize because you're building a product in an intensely competitive accelerating market. And you need to do everything you can to differentiate yourself and to like build a bigger brand than your competitors who are like trying to move as fast as possible. Well, how do you build a bigger brand? Obviously there's a whole lot of marketing stuff you need to do in in DevRel if it's like an app tool or developer facing tool. But then also you just need boots on the ground. People talking to people shaking hands, going to conferences like you do need people. So there is an argument that I can understand that they get kind of latched into, which is like, if I don't have people going to dinners, going to these things, like putting our brand out, they're talking, giving conversations, demos, educating the market. When it's a sales led, you know, model, then we're going to fall behind. Our competitors are going to out compete us. But we got to stay ahead. So like I empathize, I understand that. But there is a balance point, right? It should always be a little uncomfortable. You're hiring people before you quite have the pipeline for them and you need to like be cranking on marketing and everything top of funnel as you're hiring them. But there's a difference between that and then like you go and hire four people in one quarter with like, you don't have any evidence that you have the multiplier and there's not even really repeatability or clear product market fit or pull yet. You know, fortunately, it's not happening that often on a portfolio, but I have seen it happen. And it's just rough, you know, and there's not really, you know, you try to talk as much logic into it as a can. But people make decisions and make decisions. So there's three types of founding a roles that I've seen two or good ones. Awful. The one that's great is like, hey, we have too much inbound and like we're dropping plates. Amazing. We love working on those. It's like we're recruiting firm. The other one that's like good, but not as good as that. It's the kind of like one B or maybe just B is, hey, we're figuring this out. And if you don't hit your number at a quarter that we're going to put out, not your fault. We haven't proven out that this can be predictable. Yeah. So third type that is like disaster zone where it's like we're going to just back out of a revenue number or a valuation or revenue projections that we said based on that. And then we're going to hold you to that. And if not, we're going to say that you suck at sales. Well, to be fair, they're not going to always blame it on the salespeople. They might actually admit shit. We kind of blew that. But still, it's like it sucks for everybody. You know, it sucks for them to have to own it if they even are mature enough to do so. It's actually the salespeople. They're like, fuck, I was kind of sold on the story that was basically a spreadsheet model based off of a pitch deck or somebody thought was a good idea. Totally. Yeah. You know, I was an AE and I have a lot of, that's like what I speak to whether it's like what I podcast blog and then how I speak is a recruiter. And I just see these stories when we get inbound from this. And it's just like, oh, are you leaving it's like, oh, they're putting a lot of pressure based on a number that's like just so insane. And shit, you know, it was my fault. I didn't ask questions now. They want to with us to be like, okay, how do we diligence this a little bit? So, why do you think that it happens that way, though? That's more often than not, I have seen. It's a lot of times we're like, we need to hire salespeople before we think of, like, demand-gen. I've mostly been exposed to both happening at the same time. Rarely, we're just not even doing anything marketing before we hire salespeople. But it's usually, like, simultaneously, we're going to start building the marketing engine as we're hiring the sales team. Before the marketing team has actually had enough time to experiment and actually build a brand and get some top of funnel going. So, like, those first reps are the ones essentially building a lot of the top of funnel. And I think it happens because of the hype right now, right? I mean, the hype and the pressure of, whoa, there's, like, you know, four other founders that the VCs that gave you money were talking to that know that they're building pretty much the same thing. And you're building a product, presumably, in, like, a multi-unicorn space. And everybody's running as fast as they possibly can in it. And obviously, your competitors are also hiring big sales teams. So, if you're the one that has, like, a dinky, one, two-person team, they hire really great reps from one of the best companies to coach them from, like, you just missed your whole early-go-to-market team. So, put yourself in the psychology of the founder. Like, I get it, dude. It's like a hard thing to balance. And then for the sellers joining those companies, right? You know, you want to be asking about evidence of, like, what product market fit traction do they actually have right now or not? And how are they thinking about, like, how do they actually back into, like, hiring these next reps? What is your philosophy behind it? - Yeah. - I think it's just, like, human nature. It's like, there's a dopamine hit of, okay, we want to, we want to grow revenue. - Yeah. - It might not be the most effective way, but it feels good to just hire a bunch of, just a couple of reps, throw them in the pit, and just be like, hey, let's, like, go out and get us deals. Versus, like, it's not as satisfying to say, like, you know, it's the whole, like, planning seeds for fruit daily in six months. And I think as humans, it's, like, hard for us to, to think of that sort of, like, long term, or, like, the short-term gratification, long-term gain sort of thing. - There's just so much urgency and excitement and, like, pressure and desire to move faster. So generally, like, that's a good thing. You want a founder that wants to crush and move really fast. And, you know, it's, like, okay, you know, want to slow down a little bit. It's just kind of like a, like, a junior enterprise seller that's trying to close a deal, like, too fast, maybe. And it's like, gonna burn bridges and piss people off. - Totally. - Yeah, there's a little bit of slowing down because it's maybe, so it's like, where's the Goldilocks zone? That's all it is. - 100%. - What conversations are you having with your portfolio companies in the last quarter or two that are new compared to what you had three years ago? - That are new. I think, I don't know if there's, like, any terribly, like, fundamentally new. I mean, there's new things that are coming up. Like, it's all about open source models now. Like, we're producing inference costs and margins and explaining that to customers. - Yeah, tell us more. - That actually is an interesting takeaway, yeah. So that's the thing for what? A CTO, like, top of mind that they're coming and saying, hey, that, now, like, we're just token, we're token maxing. And now we need to, like, actually, drive down these costs, but, yes, tell us more about that. - So I mean, it depends on the product. You're selling, like, one of our, one of our companies, which is invested in an analysis of Lama. So they're in the open source space. And so, like, this is right in their wheelhouse, which is people who wanted to shift off a frontier labs to expensive data going to anthropic, and then then rebuilding a product and, like, wiping you out is scary. But I don't want to send my data to China. It's, you know, by, like, having DeepSeek hosted over there. So, like, Aloma is offering that as a solution. And, you know, like, all these new models, and you've heard of, like, GLM and, like, Kimmy, that basically, like, as good as, like, Cloud Fable. That's just becoming, like, this is a whole thing right now. And it's freaking out, like, Dario and Sam Altman, and they're, like, you know, trying to talk to the US government saying, oh, I've got to cut off these Chinese models because it's threatening to their business. So that's, like, a whole shift that's going on, and it's like getting increasingly louder this last quarter. I think on the sales side, like, I think that the way I might come up is enterprise buyers can be suspect of, like, AI native vendors that they're buying from, and how they're actually managing their token costs and their cogs, a lot of them are, like, burning money and might, like, crash. And so they're really, they actually want to understand how sustainable is your business model. Because everybody has so much pressure, basically, to run at, like, negative margins, assuming that token rates will go down, will explain to me your strategy for, like, so if I buy your software, and then you fail, 'cause you, like, token maxed yourself out of your capital, now I have to find another vendor. So, like, these are the types of things that are, like, in the nitty-gritty conversations that can come up. - So I get why a CTO, I didn't know this, that, like, now it's actually like a diligence question, hey, if I'm going to bring you on, what's the strategy? And those people can't say we're going to send it to China, so that there, it's a trickle down. Then those companies are trying to do this open-source slash. It's probably why companies, like, base 10 and fireworks are taking off in the end for this layer. So, you brought something up with Dario, and you're open-air and anthropic. This is on the prop cheap out this week of what's the difference in cost per million tokens? Fable and, like, open-air eyes close, it's, like, 45 and 50 bucks every million. Kimmy's, like, 87 cents, totally. - Dude, that's insanely interesting. - And it's like, it's performing as good as Fable. - Yeah. - This is why everybody's- - But didn't just happen a year ago, why, like, there was all these streets of, like, what was it, deep-seek came out. - Yeah. - Why now? - But I don't get the more- - The performance was as high. It was still a little behind. I mean, it was still really impressive, right? Like, I think it was, like, several months behind, where, like, the most recent OpenAI and Cloud models were. But now, the thing that's changed is, it's actually caught up and potentially surpassed some of the most recent Frontier Labs models, which is, like, wait, what the heck? That wasn't supposed to happen. - Yeah. - So, that's, like, now reorienting, like, everybody's forecast at the entire market. And these are way cheaper, and they can be hosted in private data centers that aren't going to these, like, behemoth Frontier Labs or to China. - Do you think it's a wrap if you were evaluating a company or a sales leader, you would ask or ask about the market? - The reason why I'd say, like, the margin profile being important is because we had on, actually, this morning, Stevie K, Ciro, Vanta. - Oh cool. - And I was asking, like, what was the biggest, like, learning from Twilion? She's like, our margin profile was not as ideal as you would hope for, like, a long-term sustainable business. And I think that it hurt there overall, valuation and growth and all that, how competitors catch up and limited their valuation because of it. Do you think that reps and leaders, if they're joining a series A, series B, should care about this? Or should it, you just hope that it, everything that happens, like, at Uber, it's like eventually they'll catch up with positive. Like, to a certain extent, you need to bet on that. - Yeah. - You know, you're betting on, like, the market and, like, the dynamics of this market. You're entering, you know that it's risky, you know that all this is being, like, figured out. Everybody knows and assumes that, like, token spend and all these new, like, AI, like, specific part of cogs are gonna get better. And I think what it comes down to is, like, your belief in your trust and conviction and the expertise and execution of the executive team, the CEO, the CFO, like, the investors, like, are these really the right people that are gonna be really aggressive, make sure that we're having the lead and whatever market we're competing in, and native, but aren't, like, dummies and just gonna blow, you know, our capital out of the water before we can fund raise. And, like, you know, they're able to forecast as best as you can. 'Cause ultimately, you're trusting your leaders or marching to war with. - Yeah. - And then the rest is up to the universe, so. - Yeah. - What do you guys invest in right now? What is the thesis of theory? - We try to get, we try to get involved in anything like data, AI, infrastructure. The more, like, complex often, developer-focused tools are, like, a big niche of ours, but we do operate into the application layer of, like, domain-specific expertise, building these end-to-end, like, agentic solutions that are maybe, like, not on the radar of everybody, but are clearly gonna be a huge market. So, AI-native companies and, like, data is a big foundational layer behind all of AI, you know, before it was a big market, and it's gonna be even bigger. I know that's a little bit broad, but it's, like, enterprise B2B software, and then we're going into the A-round. We're doing as much research, and the reason that's called theory is we do a lot of research and market mapping of, like, all the companies and vendors and what is being built in which market? Moreover, where do we, and what is, like, our customer community and our executive community actually see the market going? And what is our thesis on that? And what are probabilities of that being a big market? And then, who is building in that space, such that, when we find the founder that's building that, like, bizarre AI infrastructure layer that hadn't even been thought of yet, we already have a strong conviction on our thesis, and we preempt an offer when we try to get in before the VC is, like, you know, hell, like, vultures. - Yeah, so, yeah. - All right, so on the app layer, any sub-verticals or any issues that you ask is because some of the people listening are gonna be A-E's that are, like, some of them are worried about the app layer, like, oh, is this gonna be cooked by a anthropic? Or are there any, like, sub-verticals that excite you that, like, your bullish have, like, the next six to 12 months? - Yeah, I mean, I think the app, any app layer that it requires a very kind of niche domain expertise to do it right. So, like, give me one example. One of our portfolio companies is called BackOps, and they're gonna build a platform that does much more than this, but the first use case, one of the first use cases was automating with agents, the process for, like, supply chain and logistics managers at grocery stores to be able to file and get, like, refunds on goods that spoiled on, like, trucks that, like, didn't get delivered on time or something like that. It's, like, really, like, weird, bizarre thing. What they learned, 'cause somebody was, again, domain expert in the niches of that space, realized it's so heinous to do that manually that literally doesn't get done. You don't actually file all these, and then you have to lose millions and millions of dollars that, like, technically, on the terms you sign, will get refunded. - Right. - So, they're now agentifying that, and actually saving these companies, like, millions and millions of dollars a month. - Interesting. - And then you just, you know, there's the price to value on that. So, that's one example of the types of app layers that we get excited about, which is, like, anthropics not gonna go by that, and the, like, supply chain logistics engineering team is not gonna have the savvy to go replicate and build that with Claude. - What's the spectrum of, it's like a little bit of a dance of, like, yeah, you wanted to be niche, but you want the tandem to be big enough. You almost want it right below the layer that it gets too anthropic of when they, Because if it's such a big thing, like coding, they went into cloud code. 'cause they're like, "Oh, we have to head to the end of this." But you don't want it so niche and so small that it's like the tam is love, right? 'Cause as an investor. So it's like that sweet spot of like, okay, good size tam, but maybe they're not gonna, yeah, yeah. - Exactly. - You know, and frankly, if it's like big enough for cloud to get excited about it, I mean, they would have to like, at a certain point perceive it as a threat to like their overall business to do something as good if it really has to be like a full end-to-end agent system for very niche thing. It's just kind of like, obviously it's different with like cloud code and what's possible there these days to replicate something similar. But, you know, the reason why for example, Google is like going full head on with Gemini is because it literally is an existential threat to their business if anthropic and open. I take the market. So that same thing could happen for cloud and therefore yeah, there's a certain like, level of bigness that you wouldn't want to do. But I don't think that's gonna stop us, probably. - Yeah, super interesting. Any other things that founders are coming to you that they've heard somewhere else that you have to like debon for? Any other like issues that they're running into that they come to you to help solve as like a partner at theory. - Yeah, I think one. I mean, I think I have a couple thoughts on this one. Like any generic advice that's not taken in the context of their specific situation, I just get wary of, you know? Like a little see a lot of stuff on LinkedIn and other places like, oh, you gotta do this a series A. And I mean, reality is like sometimes there's some things that are repeatable and transferable to almost anywhere. But there's always nuances with like, what is the founder like? What is a team like? What is a market like? What is a motion like? Like where are the chips laying right now? One of the things that comes up in that category is hiring sellers and selling beside them as like founder led sales and getting a repeatable motion and selling with them in the trenches as the founder before you hire ahead of sales. I think that is great advice for a lot of startups and a lot of founders. It's not great advice for some startups and some founders. And it doesn't necessarily mean that they have to fail. You know, for example, if you have a technologist or a team of technologists that built like something crazy, amazing and valuable to, you know, engineering audiences and they just don't really have the go to market aptitude or chops or even like passion or interest to do that side of the business. But there's clearly something extremely valuable there. And it's not like there's other teams that are gonna be building this 'cause it's so niche and complicated to build. Well, if they are like mature enough to understand that's not what they want to do. They go hire a CEO alongside them, you know, or some sort of like CRO or, or, I'm not like a CRO like you normally think of, but it's some sort of go to market lead to help them build up a team and execute even early on. Otherwise, like they're gonna be spinning tires trying to experiment themselves and something that they don't have any experience in. And more importantly, they just don't really have like a general interest or passion or aptitude for. So they kind of need almost like a co-founder buddy at that point when they realize that there's real, like, potential here. Most of the time, a lot of people say like, hey, hire the ICs first, hire the AEs. In the case you just mentioned was, hey, it's okay to hire the sales leader first for some of these edge cases. Yeah, what's two senior and what's two junior of that sort of role? I mean, you know, what you want to avoid is somebody that's like just been used to running big teams with managers on the dashboard and they've been in like internal politics mostly. And they like, that's the type that you want to avoid. I would say that there's like a very small percentage of those people that like they've kind of only been doing that for a couple of years, but they were in the, but they still like to get in the trenches even today. Like they're skip leveling down and like going on site to help close deals at the end. Deal drunk here. Yeah, and they like are addicted to like negotiating and the win. They just can't get out of the system. I can't like get, you know, that you literally can physically see them like you can't sit in their seat. And those people are just, I think, actually, you know, even though their pedigree would almost look like, whoa, they're way too overqualified. If they're that small percentage that's still just extremely hungry to like be in the trenches with reps, they might actually work that early on in typical profile. It's probably a little safer in the goalie luck zone is like somebody's been an incredible frontline manager. Maybe they got a little bit of second line leadership or like quasi second line with like a dotted line manager somewhere and they, you know, grew up in an org with incredible VPs that they got to learn from. Yeah, but they haven't had that shot and that ability and they really want to prove themselves and they're still really hungry. And they want to get in the weeds with reps. Like that's usually the type of person that you want to bring in. But a lot of it comes with like characteristics and hunger and ambition and that kind of stuff. Yeah, so yeah. All makes sense. Before we move off this, like talking about like type gen how you see companies like building marketing, any creative ways that you've seen some of the porcos that you've worked with. Like maybe it's like they have a TikTok account or a founder just as like has a hundred thousand followers. What are some unique ways that you've seen people build pipe gen when they come to you already and they have a ripping business? Yeah, man, I wish I could think of some of the top of my head that are good. I can't think of a specific idea. Like what I can remember is the profile of the A's or the SDRs often who are the ones to think of the creative fun things. Because they genuinely have fun doing it and they're in a culture that it accelerates and like rewards it and makes it fun. There's like, I don't know whether it's some like weird gift campaign that they're doing or they're like sending like socks or like it doesn't matter. There's like an experimentation and like a fun with it and like sharing emojis on Slack about what they're trying. Those are what's coming up to me versus like a specific idea. But like that I always encourage. And like, yeah, that is the thing because you can't just repeat what somebody else did that was interesting and I think it's gonna work in your market. But you can use the pattern of being really like fun and creative with it. I love that. Yeah, 'cause like that's the stuff that'll stand out. You know, there's a really good job. This I've heard about podcasts like Sam Blond. What are you building at Brex and then we're about to have one of the VPs of sales at Monaco on. And so I was doing some prep for that. And it was like, this is exactly what he says too. He's like, just have fun with it and like get creative and you can't ask chat to be this stuff. 'Cause there's gonna give you the average of what everybody has done that doesn't stand out. So yeah. So this way you wanna like you think of something that's like funny and different. You had an exact coaching business and you mentioned, you know, your surfer, you, hey, I was burnt out. I needed to like, you know, it sounds like you care a lot about whether it's wellness or the inner game a little bit of a lot of this stuff. Yeah. I know I post it on LinkedIn yesterday of how like, would I say like a piece of advice and you know, I have to keep it a little bit spicy. Yeah, of course you do. But it's, you know, I just think I overused piece of advice and I'm probably gonna regret this one day. It's just like people on your deathbed, you'll never say I wish I were a tartar. Right. And I think that plenty of people have regrets that they didn't work harder, you know? I don't disagree, but I think that I'm probably taking this in a different way than what it was initially. Yeah. I worked too hard and then I missed my kids' games or something like that. But what I would say, yeah, I mean, again, first off, neither of us, fortunately have been like on our deathbed. Yeah. So we can only go by like, you know, evidence of what we've heard has been passed down to us or people that have gone through that. I think there's a difference between like, middle or even maybe like later life regrets where you're like, geez, you know, just I had, you know, your ego's still in it and you're just like, God, I wish I did that or like I could have done so much more with my life. I'm sure that happens probably up until some people get a lot older if they don't get over it. I think that's very different than you're literally taking your last breaths with your family at the hospital. Fair. That's not gonna matter. Fair at all. 100% yeah. That's what I mean. That I agree with. That's what I mean. That's what it is. Yeah, it's totally totally totally totally. Yeah. What did you hear when you had an exact coaching business? What are the things that execs would come to you for? Like what are the things was just to be like, a thought partner was specific for sales, was it specific for like trying to get the next realm of leadership, like what are the things that are in their head? Yeah, very common pattern. So first off, it's usually something situational and tactical that they want to work through. And often the situational and tactical thing almost always is something interpersonal or relational. It's something with their employees, it's something with their investors, it's something with their peers, if they're an executive team of other peers or whoever it might be, commonly that is the crux. And I'm not all cases, but that's often was the crux of the majority of the coaching conversations that I've had and continue to have. Obviously there's going to be a degree of just tactical, go to market, guidance and advice that they'll want to squeeze in. But executive coaching and peer coaching is not really advising. I'm not there to give you advice. I'm here to coach you through figuring out your own problem. And I'm going to ask you really candid direct questions often that you don't want to hear me ask. Because those are the ones you need to hear. And then they often have the answer inside of them. And when I say that's the first thing is very tactical and interpersonal relational, the deeper thing is something beyond interracional. And it goes to just core human experience psychology things. Whether it's just struggles with imposter syndrome or they still feel ashamed about that or they're not quite sure if there even should be running a company right now. It just gets to core things. And I'm not here to go and get them into a therapy childhood stuff. That's not what I do. But I just want people to be aware of what is actually going on in their body and inside of their mind and what are their options? And what can they do about it? And how can they move forward in a way that actually feels aligned so that they're going to be happy and motivated and confident, clear on whatever they want to do? Whether that's continued what they're doing now and finding specific ways to resolve that situation or having an honest look in the mirror and maybe changing some plants. What was the motivation for why you-- I think you briefly mentioned it earlier in this. But for you to go get coaching to be an executive. Yeah, I mean, I think a couple things. One I mentioned earlier, which is one on one stuff remotely just felt like a way better thing that I like. And so when I get into kind of coaching, ask mentorship, ask outside of even work conversation topics with employees or even some other co-workers my last company before I did that, those were some of the most fulfilling hours. I went down, I literally created a sheet of like what was it called gains and drains? - Where you're like, what do I gain energy doing during the day? Like, which hours of my day? - Very saw hillblum of you, like the color coordinated, like, red, yellow, gray. - Totally, it's really helpful. - And then like, not things that I look forward to or not, 'cause again, you might not look forward to going to the gym, but you feel better afterward. - Totally. - So it's after I do the thing, after I have the one-on-one call, after I have the team call, how do I feel afterward? And it was pretty clear, man, after these big team Zoom calls with many squares, I'm just like, I feel kind of drained. But if I had a one-on-one with somebody, I'm like, I feel energized. And so that's what kind of initially sparked it. I think the other thing is like, I've just gone through a whole lot of shit myself. It's like chronic health stuff and just, and are just like tons of things that like, I think a lot of people middle age will start going through. And I've received a lot of support, and a lot of guidance through coaches of my own. And so I know what it can feel like to be alone in like this chaos of mess, you know, at a certain point in your career and life, and not have the right support. And I know what it can feel like to have the wrong support. And be like, God, this is not useful at all. So there was a little bit of passion in there that kind of combined with that. - Got it. - Any AI tools that you're using that you like recently got put on to that you're like, oh, this creates some good leverage. - Uh, personally, could be professionally or what you've seen from others, that I-- - Oh, yeah, yeah. I wish I could say there's like a tool that's really cute. I mean, honestly, it's just like the stuff that you talk about all the time. It's like it's whisper flow with clawed and projects that you have skills running for and your transcripts. And then, you know, I use like 11 reader on my phone a lot. So if there's something-- - I know what that is, so what is that? - Like 11 labs has, 'cause, and maybe there's a better way to do this. You might know this, but like there'll be articles that don't have like a listen button yet and whatever website it is or like a post. And like, I'm just a slow reader. And sometimes I'm like, on the go. And so I just copy and paste the text or the URL. I just post it into 11 reader on my phone, and it just reads it to me in a killer voice. - I see. - I pick some cool voice. - Okay. - So I just get to like consume more interesting content. So that's been like professional use and personal for random things. That's been a fun one. - Is that through 11 labs? Is that okay? - Yeah, two 11 labs mobile. - Oh, it is. - And they released in last quarter or something, yeah. - Got it, got it. - Interesting, okay. - All right, what other like sales teams do you admire from like when you would, you know, your looker days or maybe ones that you've seen from the sidelines that could be sass or a native? Like, what are some of the GTM teams that you think have been pretty elite over the last 10, 15 years? - Yeah, I mean, MongoDB, obviously I'm in a lot of those people, segmented how to really good sales team. And then a lot of the teams that those people went to and built from there, Snowflake had a pretty killer sales team and I think some sections of the business. I would also say, so number one, I've only been exposed to like a fraction of all the killer sales teams out there. So like, I don't know where the best ones are out there, I'll be on those. I also say that something I have conviction on is that like a great sales rep or a great sales team is not universally applicable to all markets and teams and motions. You know, like, if you took like the team that was at Snowflake and tried to replicate them in the years that they were crushing it and put it into looker and their glory years, it would have failed miserably and vice versa. Like, lookers team would have failed miserably in like different contexts. And so this is where I think like generic advice on this is the way you run a team and this is how people like to think it's that simple, but it's this BS. It's like, it's actually more complicated and you have to think and compare. - Yeah, I knew it's all that, man, that's why when I posted, I can't let nuance get in the way of a good postman. - Exactly, you look back, you look back, you look back. - That's a lot of that hits. - I mean, at the end of the day, you got to ship it. - Do a lot of people, when you break down what they're trying to say, it's a lot of the same. Example, this is like, the best reps are not coin operating. Like, I have a, - Totally. - I take on this though, like, I truly believe that. It's not the same money doesn't matter. - I believe that too. - Yeah, yeah. But do you ask 50% of the sales reps that are out there and they'll say, that's the most absurd statement of course, funny matters. And it's like, I think core of what we're all trying to say is actually somewhat similar. Like, everybody just wanna be somewhere where they are solving a problem, a product that has product market fit. And because of that, the output being are gonna be financially successful and you're gonna feel like you're winning. Everybody agrees with that lineage. And in fact, if you're at, no one, no one in sales, if they were at a company not making money, if they would stay. Like, they would just, like, - Of course, of course. - Yeah. - So that's why like, that's something where I could put a polarizing LinkedIn post. But then when you really, like, go grab a beer with somebody and you talk about like, okay, what is everybody like intrinsically motivated by it? So a lot of it converges. - Well, this is just a politics. - Yeah. - It's just like perfect examples. - It's just the exact same thing. - Perfect. - Oh, this is how you do it. No, this is like a thing. - Totally, totally. - You wanna be happy and safe, wanna be stoked. - Totally. - Like, yeah, totally. - Rafa, this is great, man. Awesome to have you on. Excited to keep working with you guys in the Theory Ventures team. And what's the most creative way that somebody's ever gotten your attention on LinkedIn or anything, like Loom video or if they wanna connect with you after it, like, what's a. - Probably like getting my number through a friend and then it texted me out of the blue saying, "Hey, I got your number from so and so." You know, like, this is like, tactics like that. - Yeah. - I will say one thing, the thing that popped in my mind wasn't to me, but it was really funny is the VP sales that looker early on, somebody sent him a cake from Costco with his name, like, with, you know, yeah, written on it, whatever they put on top, didn't work. But it was a creative way of getting attention. So please don't send me a cake. - Yeah. - But I thought it was funny. - One that was going viral on Twitter was people vend milling people, you get the number and then you'd vend mill them two cents. - Yes. - I love that idea. - See, I know. - I like the creativity. - Exactly. - It hits for the first, for the early adopters and then like, they're like, oh, go. - Something I used to do was like, kind of unrelated, but I would send, I wanna do this again. I'd send friends, like, out of the blue, an annual friendship renewal fee request for like five bucks. - And like, some of them would pay it and they'd be like, "I love you." - That is so good. - It's such a unique way to keep me talking so many. - Yeah. - It's like kind of saying, "Hi, I haven't seen them for a while." - Totally. - Oh, that's funny. Well, sweet man. Great having you on and excited to keep working out. So. - Appreciate it. - Yeah. - Sweet. - Thanks for hanging with us. If you liked this one, follow the show on Spotify, Apple Podcast, and YouTube, and we'll see you next week. Cheers.

Podcast Summary

Key Points:

  1. Rafa Jarasimkin, a former Looker sales leader and current VC at Theory Ventures, discusses his transition from sales to investing.
  2. Selling to developers requires authenticity, empathy, and curiosity—no tolerance for sales pitches or BS.
  3. Common early-stage founder mistakes include hiring sales teams too quickly without product-market fit or repeatable pipeline evidence.
  4. Founders often misunderstand marketing and brand, assuming great products sell themselves, but buyers are overwhelmed with options and default to "no."
  5. AI-native companies face new challenges around token costs, margins, and sustainability, with open-source models like GLM and Kimi disrupting frontier labs.
  6. Theory Ventures invests in data, AI infrastructure, and niche application-layer solutions requiring domain expertise, avoiding spaces too large for AI giants to replicate.
  7. Hiring advice
  8. Executive coaching focuses on interpersonal issues and core psychology, not just tactical advice.
  9. Creative sales outreach, like personalized gifts or humor, stands out more than generic tactics. 1
  10. Rafa uses AI tools like 11 Reader for content consumption and emphasizes that great sales teams aren't universally transferable across markets.

Summary:

In this podcast episode, Rafa Jarasimkin shares insights from his extensive career in sales and venture capital. He began at Looker during its early days, growing from a 25-person company to a 1,000-employee organization before its acquisition by Google. His experience selling to developers taught him that authenticity is paramount—buyers in technical audiences reject anything resembling a sales pitch, requiring sellers to genuinely empathize and engage with their challenges. After Looker, he joined Monte Carlo and later transitioned to Theory Ventures, where he advises portfolio companies on go-to-market strategies.

Jarasimkin identifies common mistakes founders make, particularly hiring sales teams prematurely without evidence of product-market fit or repeatable pipeline. He emphasizes that salespeople don't solve pipeline problems; marketing and brand-building must occur simultaneously. He also discusses the evolving AI landscape, noting how open-source models like GLM and Kimi are disrupting frontier labs by offering comparable performance at drastically lower costs, forcing enterprise buyers to scrutinize vendors' margin sustainability.

His advice for hiring sales leaders is to seek hungry, hands-on managers rather than pedigreed executives accustomed to large teams. He also highlights the importance of niche application-layer solutions that require domain expertise, which AI giants are unlikely to replicate. Finally, Jarasimkin touches on executive coaching, emphasizing that most challenges are interpersonal and rooted in psychology, and he encourages creative, fun outreach tactics to stand out in crowded markets.

FAQs

You need to genuinely empathize, be curious, and passionate about what developers are doing, with no tolerance for BS or sales pitches. This matters more than with other audiences because developers avoid anything that sounds like marketing.

Hiring four salespeople in one quarter without evidence of a multiplier, repeatability, or clear product-market fit is a disaster waiting to happen. It's important to hire only when you have proof of pull and a repeatable motion.

Hiring salespeople won't solve pipeline problems. You need to balance hiring with marketing and top-of-funnel efforts, ensuring you have enough demand before bringing on reps to avoid a painful situation for everyone.

Look for someone who is still hungry and wants to get in the trenches with reps, often a former frontline manager with strong training. Avoid those used to running big teams with managers, as they may not fit the early-stage chaos.

Enterprise buyers are questioning how AI vendors manage token costs and COGS, as many are burning money and could crash. A sustainable business model is crucial because if a vendor fails, buyers must find another solution.

Companies that require niche domain expertise, like automating supply chain refunds for grocery stores, are attractive. These solutions are too specific for frontier labs like Anthropic to replicate, making them defensible.

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