Bearchats by Bearworks #1: David Lanstein's Lessons from Chamber Music, the NFL & Silicon Valley

Let's just jump into it. Hi, David. How are you welcome to the podcast. Doing great. Doing great. Thanks for having me. Yeah, so happy to have you here, I guess, David. Let's just jump into it. Could you tell me a little bit about your sales journey and how you got to be where you are today? For sure, I'm not entirely sure myself, but you know some things that happen along the way. I started out as an orchestra musician. That was my first career. That's what I went to, to high school and college for, and then played with folks from a lot of the world's great orchestras, studied with a tempest at the end of Philharmonic. And then, you know, in trying to figure out what I wanted to do next, my dad had gotten us a computer when we were kids. So we had five kids, and that was our Christmas present, I think, to all the kids one year was this used? And so, you know, we'd done some programming. And so I was looking for what to do next. Ended up getting a job basically as a sort of a glorified intern, formatting Word documents. And so I kind of figured out how to automate my job enough so that I could spend all day reading O'Reilly books, and so I kind of taught myself a little bit how to program, got somebody to give me a job, and then eventually ended up in Silicon Valley as an engineer working for a company called Splunk. Back in early time, was a Splunk, for a number of years, was kind of looking for what the next thing to do was. And, you know, for lack of a better way to put it, I mean, I just felt like, I felt like sales would be really useful as a skill. I felt like, if you took somebody who understood the products and was technical and could speak to people who are technical buyers, and you could, you could, you know, have some of the sales skills that that would be, that would be kind of advantageous. And so I went to work at a company called pager duty as the first sales hire. And that was sort of our experiment, right? I was technical mark, who's now my co founder at a totally to jump forward a little bit. He was, he was an intern at the time. He was an electrical engineer. And so our experiment was basically, can you take two technical people and build the foundation of a sales team and kind of make that work? And so after the founders, Mark and I did the first 7 million in revenue or so by ourselves, and then helped scale that company, and eventually went to the IPO process there. That's phenomenal. Yeah, what an incredible it was very random, but we got there, no, I mean to go from, you know, a musical background to then, like a coding, engineering type background to a sales excursion. And that journey, I think is really interesting, and we're really excited to learn a little bit more about, I guess, where you are now as well. But before we jump into the present, I guess, tell me a little bit more about or tell us a little bit more about jumping into sales and stay in for long, something you thought you'd enjoy, or was it just kind of the next logical step for you? Yeah, it definitely wasn't the next logical stuff. I mean, the next logical step, if I wanted to do sales, was kind of like, move from engineer to sales engineer, which I think, you know, you do see, I just kind of felt like, frankly, I felt like I would be doing all the work, and then you'd be paired up with with a sales rep who would, who would essentially make all the money, to be perfectly honest. And so it just seemed like there was room to potentially change that model. And I thought that if one technical buyer worked with one person on the sales team who knew what they were talking about, then that would kind of, then that would work. So that was sort of the genesis of how we got to this idea of, you know, can we have, you know, the SE and the architect and the salesperson as, kind of like one person? So I guess that's how I ended up there. Sorry, what were the other parts of the question? You're okay, I guess if it was the next logical jump, and I mean, based off of how you've answered so far, like considering that you did the, you know, next 7 million after the founder led sales, it obviously made a lot of sense at the time. Yeah, I mean, we chat, great, that's a good question. I mean, I think, you know, the thing that motivated me was, you know, we helped take Splunk public, and that was great. But really, I wanted to kind of go back, really as far to the beginning as possible, so I joined pager duty before the a and it was kind of like, can we take it all the way from one or so to 100 and go public? This dive bar in San Francisco used to be called zeeks, and that was called Local tap, and I made everybody pinky swear that we were going to get this thing to 100 million in revenue, is going to take seven years, and we're going to go public. And I think even Alex, the CEO, who'd CEO from, you know, think until like, 50 million in revenue, he kind of like, looked at me, I think there was a little bit of an oh, this is what we're doing moment where it's like. Okay, like, we're gonna try to make something really great here. And that, to me, is my that was my motivation, more than, you know, money along the way, which is great, but it was a lot more of like, you know, Do you can you figure out how to build one of these things from really early, like, like, can you actually do it, right? The analogy that I make with these startups is it's sort of like, you know, it's, it's like, fishing, right? And so you go out and you have a boat, and you get out there and it's you and the fish, and nobody really cares if, like, somebody else got up earlier than you did and cut the fish, or, you know, you had the wrong bait on there, or you almost got the fish, but then the line broke. Like nobody cares. It's you got the fish. You didn't catch the fish, yeah, the challenge and the just, you know, dealing with factors outside your control too, right? Like, it doesn't matter if the ocean was too warm and the fish didn't come that day. Like, it doesn't matter you didn't catch the fish. And so I think that that's part of what's what's fun about the whole thing too, is like, you know, there's 30% that you control. And I mean, you look at the factors that have gone on since Alber and I have been building our businesses like, you have a pandemic and you have your bank explodes and there's a war, and, you know, just, it's just on and on everything with AI, just these, whether they're good, bad, neutral, like there's very large forces outside your control. And you know, you have to balance riding those waves with executing on your own business. And nobody cares about reasons anymore. It's just you succeeded or or you didn't. Think it's the most exciting and terrifying aspect, right? You're you're fully in control of your own destiny, but like you said, you're not. And you know, you're always worrying about your time and making the most impact and all the million other things that you're supposed to be doing that you know you don't have time for. So, so I'm kind of curious, kind of going back to how you landed at pager duty, like, tell me about maybe tell tell us a little bit. You know what pager duty is, but how did you know this was the team you'd be excited to work with? This is the right company. You know, all the different horses you could have jumped on. How did you know this was the one you wanted to get on? Yeah? Yeah. Close deals with those two. It turns out that those work really well. Nobody wants to violate a pinky swear, yeah. I guess this is, this is sort of a relevant piece here. So in between, in between Splunk and PagerDuty, there was a company called blogly that was founded by a bunch of ex splunkers to basically build Splunk in the cloud, so predecessor to sumo logic and so on. And that's kind of how I ended up getting out of Splunk CEO there used to be Chief Evangelist Splunk he had recruited me over back then I was too young to realize what he was doing when he invited me over for for a beer at lunch. And it says, pretty naive at that point. And so anyway, you know, he said, Hey, Dave, I want you to, you know, come work here. And I said, Well, okay, but I don't want to be an engineer anymore. And he's like, okay, that's fine. What do you want to be? I said, Well, I want to be in sales. He's like, Great, let's do it. I was like, great. And then he's like, but there's this alerting system that I need you to write, and there's this thing called pager duty that you need to integrate with Jesus, all right, fine. So that was sort of like my, I don't know penance is the right word, but that was, that was my, my toll for getting to into sales as I had to write this thing. And so ended up working with the pager duty folks. You know, this is back in 2011 ended up working with the team there on this connector that we build around the system. And then pager duty was our client as well. So I was pager duty sales rep, and so got to know Alex a little bit through that. And, you know, spend more time with Alex, and then, you know, and this is going to be a recurring theme here, Alex invited me out for coffee to get some sales advice, and me not realizing what he was actually up to. It's like, Sure, sat down, talked about sales, and he's like, I've got this problem. Like, you know, we're, you know, seven figures in revenue, and we're growing 10 to 20% a month. But I just like, I don't know what to do, you know, I don't know. It's like, I need a salesperson. And, yeah, eventually, kind of stop what he was up to and and we figured it out from there. But that was, that was the very unplanned transition of how I got, got to pager duty, and got to know those folks. And so I'd love to know more about that sales transition, right? So did it feel natural? You know? How did you learn the basics? Learn the ropes was, you know, we're travel by fire. Were, you know, mistakes, tell me about that kind of curious. Oh, tons of mistakes. I mean, it's, but, yeah, I would say, like, on balance, you know, there was sort of this element of, like, it did feel like, you know, this is kind of what I was supposed to be doing, because it's, I think it feels a little bit like, you know, how I would describe product market fit, where it's like, oh, all of a sudden everything just gets really easy. Where it's like, instead of like, writing an alerting system, I just have to talk about how this system sends alerts, and that we have three telecom providers, and it's ultra reliable, and our customers are like, Netflix and Disney and apple. Not that I could ever say apple, and that was it. And then they just buy the product, and it's like, Oh, okay. Like, this is, yeah, this is kind of a lot easier. I do think that, you know, I do feel like I know what I'm talking about in terms of, like I know the product and yeah, I think that the ability to be in pretty much any situation with any level of executive and not not feel like I'm necessarily out of place, does help. And also, like early at pager duty, you know, Andreessen letter A and one thing that was really transformative for me was, you know, I had the opportunity to do all of the CIO briefings. They have a CIO brief, etc. Andreesen that we've kind of largely replicated for ourselves at atolio. And, you know, you have these meetings that you could never, you just could never set for yourself like I had. I had a couple come to mind. One was with Jeremy Derek, who is the CEO of sky and his whole exec team. They do these sort of pre briefings at eight o'clock in the morning. And so it's like Jeremy and his whole exec team flown in from London, and on the other side of the table is me, and, you know, Jeremy looks over and he's got this pink shirt on, unbuttoned down to here, and pink cufflinks. And he, like, kind of leans in. He's like, Look, you want to be like a big company. We want to be like a small company. So let's just have a conversation. And I was like, okay, you know, here's this person running this, you know, global media company, and I don't really need to be intimidated, I guess, right, because he's trying to learn from from what we're doing. And then another one was talking to satchi Nadella right before he became CEO, and said, Okay, well, have you ever heard of pager duty? He's like, of course, I've heard of pager duty. Who hasn't heard of pager duty? I was like, right. Okay, well, here's what we're working on. And I think one thing that was really helpful is like, you have these experiences, and there was another one where we met a four star general, and you talk to these folks, and it's like, okay, I guess I'm sort of past the point where I need to be kind of intimidated by somebody's title because of the way that, you know, some of these really senior people treat me as sort of like, okay, well, you know, you're just another person trying to do Good work. I think that that was really helpful too. Yeah, I think that's definitely one thing I learned to get over my hump. It's just, we're all people trying to do our jobs, and, you know, you're trying to make a connection, but ultimately, trying to solve a problem for that person you're you're working with on the other side. Um, I think one thing I'm hearing is that you have a really multifaceted background, and the fact that you've been in enterprise sales, right? You're selling a fairly technical product to a very technical user. I'm kind of curious, for people who want to go into that route, right, selling for technical products. Do you need to have? Do you think sales people should have that experience to take what it succeeds or like? Let's say you're selling, I don't know, dog food. You know to pet owners, should you have a dog as an example? Like, should you have that experience or persona? What do you think a prerequisite to do well, yeah, I think that, you know, it's less important to be great at being technical as it is, to know what you're good at and leverage that. And ideally, I mean, ideally, you are, like, really, there's, there's something that you're really good at, like somebody who I hired. It's one of the, really one of the great choices of my life. I hired this guy named Eric out of the NFL. So he played seven years in the league. He had played college or not college. He played high school football with a friend of mine from Splunk. And so this guy, Brandon, said, Hey, my friends, retiring from the NFL. Do you want to talk to him? I said, of course, sit down and he, you know, he starts it out with like, you know, I go work at Salesforce and blah, blah, blah. I said, No, you're going to be my assistant, and we're going to figure it out from there. And so, basically, he, he came in, not entirely sure if he knew how to type at that. Point. But, you know, he developed into this great enterprise rep. He moved, he was the first enterprise rep for pager duty in Sydney. And just, he's, he's done amazing work. And I used to bring him to to these clients, and he would show up, you know, looking like The Incredible Hulk, and start talking about, you know, start talking about page, review, APIs, and you know what the parameters were and what the output was, and, you know, you just, you see the reaction that people just like, can't comprehend, like, what what they're hearing. And what was it about him that made you take that, that leap, like, did he have? You know, it sounds like he didn't have enterprise sales experience. You know, was he passionate about alerting was he passionate about SLAs? You know, how did you, how did you know that this was, you know, a superstar in the making? Well, I mean, you never know. But, I mean, he, he's a grinder like he, he was not a superstar. He didn't go to a great school. He got cut a bunch of times and still, like, managed to survive seven years in the in the NFL. I remember the story. I can't remember who the teams were, but, you know, I asked him, I said, who you're rooting for in this game? He's like, Well, like, these guys cut me twice, and these other guys only cut me once, so I'm rooting for those guys. And it's like, you know, if you can get through an NFL training camp, you can get through selling software for eight hours a day. And so my theory was, you know, it wasn't terribly complicated. I just figured anybody who has the grit to make it through that could probably send some emails. Love it. David, I have a question for you just about, you know, this hire, specifically when he was going into meetings, and he was, you know, absolutely crushing it. I guess, was that a result of you training and being a part of that, like, were you implementing what you've learned through your different roles into him? Or, I guess, how did he become that to go into those teams or into those meetings and be able to sell a product? I mean, he worked really hard. He did. He did kind of what I did when I first showed up at Splunk, which is, you know, I've I found one of the most senior engineers who would spend as much time with me as possible. And we spent four hours a day together after work talking about programming, who's now my co founder at a totally up. And so it was very similar. I mean, he we would just sit in a room and work together for three, four or five hours a day, and he would just ask a zillion questions. And so his success is really entirely due to his curiosity and grit and grind and really willingness to go back to the bottom. And that's that's really hard. I mean, there's, there's a lot of, you know, I'm friends with one of his teammates who, you know, doesn't want to do this candidly, right? Like, he doesn't want to use a starting left tackle in the NFL. He doesn't necessarily want to, like, go all the way back to the bottom and, you know, make X dials or send why emails per day, or learn an entirely new field. It's way more fun to, yeah, go, have your three houses and go, you know, do what you're doing. So I think that Eric's success is entirely due to, you know, his willingness to to really reinvent himself and find what he wants to do for the next period of his life, absolutely. And I think you, you know, nailed it on the head like it's the grit when you see it in a person and what they've done and what they're doing now, I think that says a lot about their tenacity, as well as probably how they'll be in sales and their success there. I think it's great. Yeah, there you go. That's the mental model I'm in. It never occurred to me, but you're absolutely right. You want to talk about getting knocked down. It happens every play. Yeah, I think that founders kind of go in, you know, especially, you know, if you've had the good luck and fortune to start early, you go in kind of thinking that you might know 30% of what you need to know to do one of these. And I think I don't know Albert, curious what percentage you would give I would I would put it around 2% I think you know about 2% of what you need to succeed draw that experience. One of the things I learned as a product manager, you're in meetings all the time, and so you learn to show up semi prepared, but you have to go with the flow. I think you never know what you're gonna get. You're gonna go in expecting to close a deal. You're gonna get a roadblock, or you go in thinking it's a long shot, and it turns out it's a six or seven figure deal. You never know what's gonna happen. Yeah, yeah. That sounds about right. It's and they're just, I think the thing is, they're just, they're more levers and no guardrails, really. I mean, you know, you have lot like the laws or your guardrails. Everything else is, you know, laws and ethics. Beyond that, you just have a lot more levers, like if you're a salesperson and the product does a thing. And that's not what the clients want. There's nothing that you can do right? You can maybe position it differently, or try to work with marketing to come up with a battle card or differentiators or different messaging, or, you know, something, but like, fundamentally, there's there's nothing that you can do to change that reality of the product does this thing is not this other thing. As a founder, you can just make the product do something else. Now, there's a cost to that, right, like you don't want to be the leader who's making people run in a different direction every week. But you just you have a lot more there are a lot more lovers. You can go raise more money, you can sell more product, you can focus differently. You can write code yourself, you you know, but that's also, you know. I think it is disconcerting for it's disconcerting when you just realize that you know, nobody cares if it like, why it doesn't work, and nobody like it's ultimately your decision on what to do, and there's no you can have investors who can try to give you advice and input and perspectives from their experience, but fundamentally, it's like you're there because you need to make the decision. And that's Yeah, exactly, exactly. And that's a, you know, it is, it is lonely, right? Like, yeah, it can be that can be hard. Great, great. So we're very much solving our own itch, scratching our own itch with what we're building. So the thing that we always felt like should exist is Google at work, companies have been trying to crack this for 25 years now, I think it's in the original Google business plan. And so, you know, we we always wanted this thing. It's like, how do I find knowledge at work? How do I answer questions that I have, and how do I understand who knows about the thing that I'm interested in? But I think, you know, well, one fortunately, my co founder, Gareth, came to me one day and said, like, Hey, I just figured out the the answer to relevance and, like, how this whole thing is supposed to work, and why none of these other systems actually work. And so that was really helpful. But two, you know, I think you know, when you look at this problem and you look at, essentially, okay, well, you know, Google's tried to solve this problem, and Microsoft has tried to solve this problem. I think if you're, if you're smart, anytime that you think that you're going to solve a search problem that Google has not been able to solve, you should, one, reconsider your line of work. And two, you know, assuming you're still sufficiently insane, assume that this problem is much harder than it appears. Even though it appears really hard, it's harder than that for reasons that aren't clear, because lots of companies have tried to solve this, and have, you know, the ships have sort of run aground. And so the first thing that we did was really we talked to around, not around. We talked to seven companies before we launched our product, because we wanted to basically build a better understanding of what this thing actually looks like that than really anybody else had. And so those we learned a few things that were really critically important, but a couple of those are one, when people think about knowledge, it's more about they think more about information. Like the assumption is that you know what you're looking for. When you see search results, you know what they are, and that you're fundamentally looking for text, things I can read, or what have you. And it's as much about the people and who knows what, and how do I get answers to questions as it is, you know, I'm looking for a specific piece of content. And so, you know, we kind of reframed the problem as, how do we help you better work with knowledge at work, regardless of how much context you have, so basically, from your first day at work. And then the other piece of this is, you know, we talked to 100 of the Fortune 1000 as we're building this product, and no real company is going to send their data to somebody else's cloud, right? And so whether the entire solutions hosted on a public cloud, or just the front ends hosted on a public cloud, that's not acceptable for large enterprises, right? Because they have no, no real idea what's in these systems. And so we had to build something that runs entirely on the private cloud of the client to be able to service, you know, serious enterprises. And so we were fortunate in having a lot of these senior execs, I think we talked to a few 100 CIOs and CTOs of large companies, we were fortunate to have that input as we were building the product, to make sure that we built the right thing. And then with llms and applying, applying those per question, answering the same thing applies like there are come. Companies that have Enterprise open AI, Azure OpenAI licenses, where they're okay sending using that for question answering, where they can answer questions on their internally, private and public data using open AI, there are companies that want to keep that entirely private and use the models and run those locally, because the theory is the models are how they make better decisions, and so those become part of the crown jewels. So we felt like it was very, very important to align how we build this product and how we deploy it to how large enterprises want to run. And we definitely feel like the problem is biggest at the largest enterprises in the world, with most people creating the most knowledge over a long period of time, and specifically where that knowledge retains its value. It's definitely exhilarating, and we're very grateful to our you know, our fortune 50 folks and hyper growth companies like cribble and adaptivist that have bet on us and have been with us from the super early days. There's a slight anecdote. This doesn't have to make the cut, but it just reminded me, David, when you mentioned and correct me if I'm wrong, because it kind of cut out a little bit. But Google and Microsoft were looking at trying to do something like this, and maybe they couldn't figure it out. And that's where you guys jumped in and are solving it. Do I have that right at least? Yeah. I mean, Google had the search appliance that was deployed back sorry, the Google Search Appliance that was deployed in data centers, Microsoft has tried to solve this a bunch of times. They have SharePoint search. They've tried to make, tried to kind of unify search across their own ecosystem. But the problem is also that, like you know, companies are heterogeneous in terms of the tools that they use, right? Like no enterprise is entirely all in on Microsoft. They have stuff from Microsoft, they have slack, they have JIRA and Confluence from Atlassian. They have, they might have GitLab deployments. And so part of the challenge is, how do you unify the knowledge from all those different vendor silos, centralize it understand the permissions on all the underlying objects in those systems, so, you know, hundreds of millions of documents and conversations and so on, and then be able to build a rag system so that you can have question answering across all that data, while taking into account a set of knowledge that any given user has access to at that moment where they're where they're asking The question, I mean, that's and then deploy all that on infrastructure you don't control. That's basically what you have to do. So powerful, yeah, and it it like reminds me of my own, like, I used to work at HubSpot, and our whole thing was single source of truth, right? Like, everything in one place, and like, that is such a selling point, because otherwise you have all these siloed areas that if someone leaves, maybe you lose access to something. Or, I don't know, a bunch of new hires Come on, and they need access to everything. So that single source of truth and having the ability to access everything is incredibly powerful. So that's very cool. Thank you. Of course. Yeah, that's my one point for all I think, David, we have a quick set of lightning questions for you. David, what's your favorite beer? Partake, non alcoholic. Pale Ale out of Canada. If you're into non alcoholic beers, partake. Brewery. Awesome. Lifesaver, delicious. 10 calories. Sounds very healthy and tasty. What's one sales tool you can't live without airplanes? It sounds like TSA Pre and clear as well. Yeah, yeah, yeah, one A and 1b Wait, that is such a good answer because I literally thought you were talking about. I was like, What is airplanes? But you mean, like, literal airplanes? Yeah, literally airplanes. I'm on a plane probably 48 weeks a year. Oh my gosh, there's just, there's no, there's no other way to do the job. Do you have a favorite airline? Sorry, Albert, I have an airline that I fly a lot, which is united. Nice, cool. David, you should share. How many miles Have you collected in the last five years? I've, I don't know, I have about 3 million left. Yes, okay, in person or virtual meetings. In person, it's just, there's again, there's there's just no, there's hard negotiation or building rapport. I think that when people think about negotiation, they don't think of they don't think they don't know what they want, right? So step one of negotiating is you have to figure out what it is that you actually want, and so you can negotiate. I mean, I'm going to cheat and say both, because, like, you can't not have rapport, and you can negotiate hard, so long as you know what it is that you want, because when you know what you want, then you can figure out what the other person wants, and then you can negotiate hard for what you want, but still give them what they want. It's when you don't know what you want, and you go in and you can try to negotiate everything, every point. That that's, I