20VC: Why Too Many People Give Up Too Quickly, Why You Should Never Start A Venture Without Owning The Underlying Data & Why We Have Over-Estimated The Ability of Automation with Dennis Mortensen, Founder & CEO @ X.ai

Dennis Mortensen is the Founder & CEO @ X.ai, the startup that realises scheduling sucks and provides ridiculously efficient AI software that solves the hassle of meeting scheduling. To date, Dennis has raised over $44m in VC funding from the likes of Firstmark, IA Ventures, Lerer Hippeau, DCM and more fantastic names. As for Dennis, he is an expert in leveraging data to solve enterprise use cases and prior to X.ai he was the Founder & CEO of 3 companies, 2 of which were acquired and one which went bust or as he describes a rather expensive MBA. Dennis is also the author of Data Driven Insights, on collecting and analyzing digital data. In Today’s Episode You Will Learn: 1.) How Dennis made his way from Copenhagen to New York, the world of startups and came to found one of the hottest AI companies of our day in X.ai? 2.) What were Dennis' biggest lessons from enjoying 3 successful exits prior to X.ai? What were Dennis' learnings from his one failed startup? What would he do differently if he were to start another company? How does Dennis navigate the balance of between pursuing a vision and miss vs when something is just not working? 3.) Does Dennis believe that there really is such a thing as an AI first company? What is the right mentality to approach a company solving a problem through AI with? How does Dennis view the standardisation of AI tools today (Tensor Flow, libraries etc etc)? Does this remove barriers and defensibility for AI companies? What is the key to success for all AI companies? 4.) What does a truly differentiated data acquisition strategy look like? How can one determine the different utility value between different sizes of data? At what point does Dennis believe utility value of data diminishes due to the sheer size of existing data? 5.) Does Dennis believe that conversational UI is truly a paradigm shift in the way we interact with our devices or an iterative improvement? What have been some of the biggest lessons for Dennis in designing conversational UI products? What have been some of the fundamental challenges? Items Mentioned In Today’s Show: Dennis’ Fave Book: The Narrow Road: A Brief Guide to the Getting of Money, Shoe Dog: A Memoir by the Creator of NIKE, Mike Tyson: Undisputed Truth As always you can follow Harry, The Twenty Minute VC and Dennis on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back to the 20 Minute VC and Founder's Friday with me, Harry Stebbings. You can find me on Instagram at H Stebbings 1996 with two Bs, where you can suggest both questions and guests for future episodes. It'd be awesome to see you there. However, to the show today, and another episode which makes me very grateful to do the show, a friendship that would never have happened without the first episode that we recorded, and now thrilled to welcome back the very special Dennis Mortensen, founder and CEO at X.ai, the startup that realizes scheduling sucks and provides ridiculously efficient AI software that solves the hassle of meeting scheduling. To date, Dennis has raised over 44 million in VC funding from the likes of First Mark, IA Ventures, Lira Hippo, DCM, and more fantastic names. As for Dennis, he's an expert in leveraging data to solve enterprise use cases.

• 0:45Harry Stebbings?

  And prior to X.ai, he was the founder and CEO of three companies, two of which were acquired and one of which went bust, or as he describes it, a rather expensive MBA. Dennis is also the author of Data Driven Insights: On Collecting and Analyzing Digital Data. However, before we jump into the show with Dennis today, and I want to spend a minute to talk about Brex, the first corporate card for startups. Brex founders Enrique and Pedro built a payments business in Brazil, but found themselves rejected for a corporate card when they were in Y Combinator. They decided to build Brex with instant online signup, no founder liability required, and limits 10 to 20 times higher than standard cards. Pretty incredible, I know. And you can sign up for Brex today and get fees waived by entering the code HARRY during signup. Honestly, it really is such a special service.

• 1:29Harry Stebbings?

  And with Brex in place, we now need a team to really use the cards. And that's where Terminal comes in. Terminal is a startup that appreciates hiring amazing developers is really hard. Plus, it's even harder if you're only looking in a 25 mile radius of your office. So Terminal is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Well, Terminal does this by focusing on everything necessary to successfully source, set up, and support these teams. From physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this. Take the word of Eventbrite, former 20 VC guest Hims, and DialPad, all of whom customers and love Of terminal and you can find out more today at terminal.io.

• 2:13Harry Stebbings?

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• 2:53Harry Stebbings?

  Just go to lattice.com/20vc. That's L A T T I C E dot com forward slash two zero VC. Build an award winning culture with Lattice, the number one people management solution. But I'm now very excited to hand over for a very, very special round to Dennis Mortensen, founder and CEO at X.ai.

• 3:17Speaker 01

  You have now arrived at your destination.

• 3:20Harry Stebbings?

  Dennis, it's such a pleasure to have you on the show today for a second time. What can I say? I so enjoyed having you on the first time. I had to have you back. So thank you so much for joining me again today, Dennis.

• 3:29Speaker 02

  Thanks much for having me. This is gonna be awesome.

• 3:31Harry Stebbings?

  It is indeed, but I want to kick off today. And for those that made the cardinal sin of not listening to our first episode, I'd love to start by how did a native Dane make his way to New York and come to found one of the hottest AI startups of the day in X.ai?

• 3:45Speaker 02

  The very short story in my very short life, given I'm only 46. It's one for where I did a few ventures back home in Denmark, then moved to England for a while, then moved to Budapest for a while, where we spent four years doing a analytics venture. And that one got acquired by Yahoo and part of the acquisition terms were that I moved to New York. And I thought I'll just spend a couple of years in New York and that was 10 years ago. Now the kids are in school in New York and really anything I'll do in the foreseeable future will be from Wall Street where I live and I've spent the last 10 years. Now, how did I get started on X dot A I? I think it's one of those things and it's gonna sound like that eBay story, which is kind of not really true.

• 4:29Speaker 02

  Whether they started the whole thing based on that sort of pest expenses, but you know what? I actually did start this whole venture by going back into my calendar and seeing exactly how many meetings that I did. And as I looked at that, I just thought a thousand meetings a year, which you sit and schedule yourself in your underwear at eleven P M. Is that your life, Dennis? And I thought, that can't be my life. There needs to be some sort of escape and we're working on that escape right now.

• 4:54Harry Stebbings?

  Well, I mean, it's no longer my life, thanks to Amy, but I do wanna ask Dennis, you mentioned there are a couple of your ventures beforehand. Three companies before X dot A I as founder and C E O and C O O at another. Success ranges from acquisitions to Yahoo to, as you said, going bust, which you describe as an expensive M B A. I did love that. But tell me, what did you learn from the success first?

• 5:15Speaker 02

  I like a little bit of extra money in my pocket, but that's not the good part of it. I think the good part is that when you do see success, then you dare to do something slightly more brave next time. As in anything for where you do a ten mile run in your head, I could do a fifteen mile run, or you do a three K swim. I can do a five K swim and before you know it, you're swimming the English Channel. Those son success breeds bravery to do something even more grand next time. That's certainly what I'm fond of, because if you do five things and none of them are working out, you could end up being just slightly timid in your ideas and your approach and your attacks. And I'm certainly fortunate in having started out this whole journey with a win.

• 5:58Harry Stebbings?

  Yeah, absolutely, but I'm not so sure about the fortunate. I think more skilled. But as we know, ups come with downs and as we said, the expensive M B A with the company that didn't work. On the flip side, what did you learn from the failure?

• 6:10Speaker 02

  If I were to go back and redo anything, not to kind of pretend I could have made it work. In my mind, obviously, when I go to sleep, I still think I could have made it work had I just changed two or three decisions. But the one thing I would really have changed would be the closing it down. I think I could have closed it down better, but I. fought so hard to the very last day, then another three weeks, then another two months for where, hey, Dennis, this thing died three months ago and somehow you kept it on life support and everybody would have been a little bit happier. Had you just not tried to kind of keep it alive and it's okay to lose, but when you lose the first time, kind of like drowning. You don't want to drown, right? So you kind of splash around a little bit for where this party is over.

• 6:54Speaker 02

  So certainly in hindsight, would have done that better, spent a little bit more time on it. And just accepting the fact that being an entrepreneur or being in the startup game, it's just a game. And if you lose, you're an equally good human being and hopefully you learn something and you go play another game. But at that moment, perhaps being a little bit younger, I just didn't want to drown. And what happens when you drown is that you start to kind of lash on to other people for where leave them the fuck alone. I said, they're swimming, they're kind of okay. Don't kind of drag them down with you, Dennis, but you're not thinking super clearly in that setting. I think, or I would like to believe that in my older version, slightly more mature perspective, I would just die respectfully.

• 7:35Harry Stebbings?

  Now Dennis, I did expect to go off piece, so to speak, with the schedule, but I didn't expect to go off piece quite this early. But I have to ask, combining both the success and the failure, how do you determine when something's not working? When to follow the vision and the mission, so to speak, versus when to really just realize that you're drowning and fighting a losing game? How do you make that decision and fight the balance?

• 7:57Speaker 02

  That's an awesome question, right? And I'm not sure any one of us have a really good answer. I do think though, and this is pure opinion, that most people give up too quickly. I certainly believe that there's a real dramatic cost when you give up too late. And you try to kind of find that equilibrium. And I certainly much rather err on the side of giving up a little bit too late than giving up a little bit too early. Because the whole most likely outcome of any startup is that we will die. But the only way to kind of figure out that you will not die is to take it so far into the future that you find something that was not visible in the beginning. And you have to kind of keep pushing forward. So I would certainly suggest, not based on my prior commentary, that People kind of keep plowing forward.

• 8:41Speaker 02

  Now, the signal, I think, is having at least determined upfront what you would agree is some sort of end to this, which could be no more money in bank, but not necessarily. No more money in bank might just mean that you're not paying yourself any salary anymore. Then it could be not paying myself salary for eight months, or not paying me and my co-founders any salary for eight months, or not paying me and my co-founders any salary for eight months and not paying taxes for four months, or however aggressive you want to be. But I think the best way to do it is to do it upfront while you're still sober and sane, not while you're fighting the good fight.

• 9:15Harry Stebbings?

  No, I completely agree, and I think you're absolutely right in setting that benchmark. But I do want to move away from the deep self-reflection. I'm sorry for that one. But I want to start with the theme of AI. And through many conversations I've had with LPs, they ask, do you focus on AI, Harry? And I always respond that AI is this enabling technology that powers the verticals we know already. So I'm looking for some validation here, my friend. I want to ask, is there really such a thing as an AI-first company, Dennis?

• 9:42Speaker 02

  I can certainly see startups take advantage of specific technologies at certain moments in time. I'm not sure I'm a fan of companies using that as an excuse to begin the journey. I think any company should be based on some really solid foundation of pain, something or some set of things that are not working in the universe, and you're trying to fix them. You might then figure out that, hey, does this particular technology, which we can use to fix it, faster, better, cheaper, more optimal? And it happens to be that the pain we are trying to solve or trying to remove is the pain of setting up meetings. And it certainly looked like when we started that the conversational UI and the intelligent agent,

• 10:26Speaker 02

  and thus AI, would be a good way to remove it. But it's not one for where we want to be an AI-first company. Now, we want to be a meeting-scattering company that happens to use AI. So I'm very much in agreement with you that you shouldn't try to be mobile-first or AI-first or cloud-first or big data or whatever the term might be of the particular era. You should just really latch on to that customer pain because that's That is the truest thing that you can let on to.

• 10:52Harry Stebbings?

  Well, I'm so pleased to hear that and I'll be sending this episode to all our LPs. But I do want to ask then, given that, there's a lot of talk about the standardization of tools, libraries, what TensorFlow allows, et cetera, et cetera. But will this largely remove much of the barriers and defensibility? And how do you think about this as a company that is powered by AI?

• 11:12Speaker 02

  I'm certainly a fan of good, strong libraries. And I'm a fan of things being standardized. And I'm not sure that by those things being commoditized, that there's no room for startups. If anything, I actually don't even think that is the biggest obstacle. For me, and if I look at all of the time and energy and money that we spent over the last good four plus years, that went into defining the universe that we exist in. I said, go pick up any self-driving car project right now. It is not their ability to build a model that makes a prediction. It's trying to figure out, what am I even trying to predict here? Am I trying to predict whether there's a pedestrian or whether there's people? Whether there's a sign or what am I even trying to predict?

• 11:56Speaker 02

  And if I'm trying to predict something, on what data am I trying to predict it? How do I get that data? If I get it, do I need to label it? If I need to label it, how do I label it? If I do label it, in what application? Because it's obviously not in Microsoft Word, but if not that, where? So there's a ton of challenges before you're trying to kind of craft your first model. And I think many of the models that we've done here, if that's based on some output of a TensorFlow installation, fine, because that is the least of challenges. So no, I don't think that is an obstacle for a good entrepreneur to kind of jump into the pool and play along. All of the kind of examples I gave, that is where you're really fighting.

• 12:37Harry Stebbings?

  No, absolutely, I agree. And I always think, and again, please correct me, that differentiation occurs really in the data acquisition strategies and kind of the moats that one can build around the proprietary data that they collect. How do you think about data acquisition strategies today? And whether that is a proprietary mode that startups can and should leverage in the future?

• 12:55Speaker 02

  So you and I are certainly very much on the same page. And it sounds like we've chatted before and I can. A test of the fact that we did not, but I very much agree with what you said. And I would never, and I'm underlining this, never start any venture for where I didn't own the underlying data on which my venture operated. I said, I couldn't in good faith start a venture for where, oh, the data set is based on, say, the Twitter files, but Dennis, that's not your data. Somebody else now got a lease on your future. And if they decide that you shouldn't exist, you don't exist. And that's just not a setting I want to be in. Now, if you need to own the underlying data, that sometimes ends up being really painful,

• 13:36Speaker 02

  complex, burdensome to figure out where do I get it, at what cost? And how do I store it? And how do I get more of it tomorrow? And is there some sort of built in data acquisition loop in my product itself for where the more I do, the more data I get? And that is certainly something which I personally tried to spend a lot of time on in the very beginning. Because if I can't justify that, I'm not sure this is something which I should get going with. And if you look at kind of what we do here, for every meeting we do, we get a little bit more data. For every tiniest set of data we get, which we label, we get a little bit smarter. The smarter we get, the more likely is I'll get another customer. If I get another customer, the more likely is that he's going to do another meeting and there is my loop.

• 14:18Speaker 02

  And if you can't, at least even in fantasy, kind of come up with some sort of loop, you are perhaps up for a struggle for where there is not really any winning. Perhaps in a short span of time, you might win a little, but then when somebody wakes up, they'll take it away from you. So you must really try to figure out how to own this.

• 14:36Harry Stebbings?

  And Dennis, I have to ask, after four years, you must have a ton of data. With that in mind, how do you think about giving inflection points in the utility value of data sets? Once you reach a certain quantum of data?

• 14:47Speaker 02

  I think it's very difficult to know exactly how much data you need. Because if you know exactly that I need seventeen million emails for where thirteen percent of those emails will have a new meeting intent and seven percent will have a cancellation intent. If I get those intents labeled, then I have enough accuracy to kind of have a product in market. I said, those Answers aren't clear on day one, you can certainly make some sort of projection, get a little bit of data, see what the curve bends towards, and there will be a moment in time where there's a diminishing return on that extra piece of data which you get, which is fine. So we certainly tried very quickly

• 15:29Speaker 02

  in kind of the four years that we've been at this to see what are the intents we're trying to pick up in our universe, intents like new meeting, council meeting, reschedule, running late, adding participant, your manager and so on and so forth. What is the one that happens the most? Because the one that happens the most, if I can get a curve for that, that might be an indicator of what I need for the remainder. If I can see how often the remainder happens, then I know exactly how many meetings I need to do all in all to get to the end. So we quickly had a set of projections, not necessarily proofs, but certainly projections on this is how many emails we need all in all, this is how many meetings that I kind of add up to, and this is how many customers I need to kind of have in my network to make that happen.

• 16:09Speaker 02

  And that became the basis for the kind of ask both in our A and B round for where we certainly believe this is how much we need to get to the other side. If we only kind of have capital to get half, then I think we are on some sort of suicide mission and that doesn't sound healthy. So certainly agree that you should try to project, but it's very hard.

• 16:27Harry Stebbings?

  For sure. No, I understand the difficulties in prediction there, but you did mention the element of intent. And I want to dive one layer deeper into the application of AI and really the delivery mechanism behind it. For you firsthand, you've experienced that kind of boom of the conversational UI, and we've seen that from Alexa to Google Home. The big question for me here is, is this conversational UI, is it truly a paradigm shift in the way we as humans interact with our devices? Or is it really an iterative advancement in our communications?

• 16:55Speaker 02

  So I'm a believer, so anybody who listens to this should expect me to have some bias, but no more bias than tomorrow, 10th of October, we're going to do this grand relaunch of X dot AI, Amy and Andrew, and then kind of being mixed in UIs. But let me just take a couple of steps back. So I'm certainly old enough to have some memory of having taken my CS degree on the command line, and that being Pretty much the primary UI for any type of access to compute back in the late eighties. And certainly years prior to that. And I certainly also remember the introduction of the graphic user interface and my mom getting access to word processors and a whole lot of other people who didn't have kind of a specialized

• 17:39Speaker 02

  education, understanding how to use computers. And I certainly also remember the mobile UI and my kids getting access to touch interfaces. And that probably being a distinct UI in its own right. And having said that, I do believe that the conversational UI is a distinct UI in its own right. And I think it's very important to kind of make a distinction between a UI and what happens on that UI. The conversational UI does put different demands on the user. If anything, I actually think it might finally fully democratize access to compute. So even the least tech savvy person can now figure out what the time is in Singapore without knowing how to boot up a browser and go to Google and search for it. But can I actually just ask some assistance?

• 18:23Speaker 02

  Though I am very bullish on this being a very dominant UI of the future. Not the one for where every prior app that we've had up until this point will move over to this newer UI. I don't think that's the case. I think we'll still have a mix of UIs. Just like most of my engineers manage all our servers on the command line on AWS, I said, they didn't move into other UIs. And certainly my visual UI designers still sit at a big ass monitor and use a graphical user interface and my salespeople still, you know, running around the city with mobile phones trying to kind of add things to Salesforce. But I do believe this conversational UI is so distinct that we'll see a change in behavior and a new set of apps. And the one thing that I'm certainly seeing happening is that all of the prior UI paradigms

• 19:08Speaker 02

  had one thing in common, that they assisted you in doing a task, doing that task a little bit faster, a little bit more accurate, doing the task in such a way that you couldn't really do it by yourself to begin with. As in, you're trying to do a pivot table on paper, it's kind of a mess, but you can do that in Excel. Now, that is something where you do the job and you take credit for the job. Now- In the conversational UI, for the first time, it became very easy to describe objectives. Things you want done that might require multiple subsequent set of tasks done for where you are not a participant in any one of them. So even in my little world here for where, hey, Amy, can you set up a meeting with Harry come first week of December? When he's in Manhattan at my office on two hundred Broadway?

• 19:52Speaker 02

  That's something which I want done, but I don't know when you're gonna be in Manhattan. You don't know exactly where on two hundred Broadway I live. Is that on the first floor, on the nineteenth floor? And that means I've now described the objective where I certainly know what I want done. It's now up to Amy, the agent, to figure out, okay, I know the job and I'll have to figure out what are the number of steps I need to go through. But it also depends on what Harry kind of responds with. And that conversational UI is just such a good UI to take in objectives. I'll give you one example, take a recurring meeting. That is actually a little bit of a mess to describe in a UI, but it's very simple to describe in text. I should do a monthly finance meeting come first Wednesday every month with Joss.

• 20:35Speaker 02

  And I can easily kind of describe what I want, but trying to kind of do that in dropdowns and Google Calendar? Not impossible, it's just not the best interface. So those objectives, I'm just a huge fan of and super excited just gonna see happen. And I can certainly see even with Amy and Andrew, which is kind of a small attack on this, just for scheduling meetings. What people love the most is that initial description. That is where we really add a ton of value.

• 20:58Harry Stebbings?

  For sure, and I promise you, Dennis, when we do next meet, it will be in a cocktail bar with a mojito, not in your office. But I love that suggestion, that kind of augmentation of kind of human ability there with the agent, as you said. I do have to ask, how do you envision that the human machine collaboration moving forwards? In these very first beginning stages of kind of the AI revolution, so to speak?

• 21:18Speaker 02

  So hand on heart, I had certain beliefs, if you go back four years ago, that turned out to be not true or way too optimistic. So here's a version of Dennis from four years ago. I would initially have told you, you ask Amy to set up a meeting with me first week of December. Amy emailing you anything, any question, any clarification.

• 21:40Speaker 02

  Would be a sign of weakness or failure. All you need to see from Amy is an invite. As in, I asked you to do a job and you just do your fucking job. And that means me getting my invite. And that is it. That is very aspirational and I can certainly see why I leaned into that. But I'm not sure it's a good reflection of how the world works. And what we've found over the years where there's not really many books you can buy on best practices for conversational UI design. And that's something where we've suddenly been forced to come up with some of our own best practices. And what we can see is that the agent going back, asking for clarification, is not a sign of weakness. It might actually just be exactly what you want.

• 22:20Speaker 02

  Where say Harry have set up a multi-participant meeting with the folks over at SoftBank because you want them to be an LP in your fund. And seven people are participating, then one of them choose to kind of decline. Do you want Amy to decline the whole meeting and start over? Or do you want her to say, hey, I can see that one of the associate counsel, do you want to keep the meeting intact? And your answer will be, yeah. But if one of the partners counseled, then you might want to say, hey, you know what? Let's find another time later in this month. So this whole idea of asking for clarification is certainly something that we've learned and that works very well. We've also found that some things work very well in the conversational UI, but some answers don't necessarily need to be typed out. So Harry and Dennis are meeting.

• 23:05Speaker 02

  Somehow you're a little bit squished for time and you email Amy saying, hey, can Dennis come up to the hotel in Midtown? And Amy will then kind of take your hotel, write it back to me and say, hey, can you meet up at Harry's hotel? I could write back, sure, we can meet at Harry's hotel. Or we could just include a button where you click and that means yes, right? So that is what you'll see us doing this kind of launch tomorrow on October 10th, where we are willing to kind of include a button for where if the answer is Boolean, as in yes or no, just click here, man. Don't make it more complex than it is. And you suddenly kind of experience this even just speaking to your Alexa or Google Assistant at home, where some things are, hey, just turning a little bit too cumbersome for something which is kind of rather simple. And that is where I think mixing.

• 23:50Speaker 02

  The UIs, it's not a bad idea.

• 23:52Harry Stebbings?

  Can I ask Dennis, do you feel a little bit like Elon Musk in terms of overestimating the role of automation? And now appreciating the importance of human interaction and interjection?

• 24:02Speaker 02

  Well, first, if you say Elon Musk and my name in the same sentence, what I feel is impotent. I say, and I'm not doing things important enough. And Dennis, man up, do something real. So there's that. But in regards to automation, I think I certainly also overestimated the ability for an intelligent agent to do every little single detail. Where it seems simple, but any human negotiation very quickly turns super complex. And it's very subtle. It is so subtle that really only Harry knows. And there's no clue, there's no amount of NLP, there's no amount of accuracy that could have figured that out. Your willingness to go downtown to meet Dennis on Wall Street.

• 24:48Speaker 02

  I said, only Harry knows. So I've certainly, again, hand on heart, overestimated that a little bit. But I think I swung the pendulum back a little and I figured out where do I mix the UIs? And we can see for every one of these things that we've done for where if you go ask my PMs, they'll say, yeah. Dennis wasn't necessarily a fan because he had this kind of utopian idea of the future. And we had to kind of push him into current reality while keeping his version of the future alive. But they have worked very well. I said, we've never had better retention than this week. We've never had more meetings per host set up than this week. We've never had a higher NPS than we've had this month.

• 25:30Speaker 02

  So all of these things have certainly worked towards being more aligned to November, October of 2018 and not Dennis's version of 2021.

• 25:40Harry Stebbings?

  Dennis, you spoke there about the change in mentality for you. I spoke to many of your investors before the show, from David at DCM to Brad at IA. I wanted to ask, because the commonality amongst my conversations with them was your ability to retain your entire founding team, which has been with you since 2013. Obviously, I don't need to tell you how rare that is, but I do want to know. Dennis, what is the secret to not only hiring these managers, but also scaling and retaining them over time?

• 26:06Speaker 02

  So you of all people, perhaps even more than me, know the few reasons for why many startups end up not succeeding to the extent you had hoped for. And certainly, one of them is that the founding team either couldn't figure it out together, can't stay together, that were super happy on day one, a whole lot less happy on day eight hundred. It certainly makes it a little bit easier if you find a team of people that you know you work well with. So of the four founders, where I'm one of them in X dot AI, three of us already worked together in our prior ventures. So we worked together for, yeah, about ten years. So we're not surprised by all those kind of little kinks that comes along with being

• 26:48Speaker 02

  a human being. And we're together because we have specific qualities where there's a little overlap, but not much. As in, I know exactly what Alex is good at. He knows exactly what I'm good at. We know exactly where, Dennis, don't fiddle with that. Just leave it to Alex. And he knows exactly, nah, that's not my responsibility. Dennis will fix it. I don't even need to look at it. But it doesn't mean it's easy. So any, any startup is just hard. As in, sometimes surely you win the lottery and you stumble into an Airbnb. And if you're Brian, good for you. The rest of us, we just have to plow through a ton of shit years on end and see if we can get out on the other side. And that is hard.

• 27:33Speaker 02

  I do certainly think that if you can keep a real good idea of where you are headed. As in, if you six sack too much, that is not a fun journey to be on. If you're fighting the good fight and you're fighting the same fight and you can see the destination, you might only over the last three months have ins for a few basic steps. Okay, that was fucking hard. But hey, we move forward. And I know we move forward because we've all agreed on where we're headed. We also also agree that we might not make it, but we are moving forward. And that certainly is, if I was gonna give. One indicator, if you can let's answer something where everybody accepts that dying is okay.

• 28:15Speaker 02

  Change the direction is not okay. So we never use words like pivot or what have you. We are just very comfortable in dying on the idea that setting up meetings using an agent like Amy and Andrew. Or any one of the other kind of UIs that we're using now, if we can't do that well and we die. Hey, we'll go home and say, we played, you know, a good game. We think we gave you the best we had, but it wasn't our time. But we didn't zigzag, we leaned into it.

• 28:41Harry Stebbings?

  But I do wanna finish with a quick fire round, Dennis. Yeah, I say a short statement and you give me your immediate thoughts. Are you ready?

• 28:47Speaker 02

  I am ready.

• 28:48Harry Stebbings?

  Okay, so sixty seconds per one. What does the morning routine look like?

• 28:52Speaker 02

  Three K run, forty five minutes on the weights.

• 28:56Harry Stebbings?

  Nice, like it. No wonder you're fit and I'm not. What's the biggest productivity tip or hack for you?

• 29:01Speaker 02

  Inbox zero and keeping a very anal calendar.

• 29:04Harry Stebbings?

  What's the favorite book and why?

• 29:06Speaker 02

  I'm gonna add a few here and you're gonna hate me for it. Here are three non-obvious entrepreneurial books. So you all read the same books, The Hard Thing About Hard Things, Zero to One and so on and so forth, and they're wonderful books. I'm gonna give you three books with a different perspective. One, The Narrow Road with Felix Dennis. Which will teach you about how much you should value your equity. And how much of a fight you should put up if you want to lose one of your shares. It is a rude book and he's an awful human being. And there's nothing from him as a human being that you should take note of, and he says so himself.

• 29:45Speaker 02

  And the one thing that gets to you at the end is, I gotta keep my shares, man. I gotta keep my shares. Now, that's the first book. The second book would be Shoe Dog by Phil Knight. Read that book, which is a wonderful story and you can read it for the story and see, damn, that's how Nike came about. And there was at least kind of seven reasons for why Nike shouldn't have existed at all. But it'll teach you about one thing, that the sacrifice is probably gonna be way bigger than you're willing to accept. If you really think about it, major sacrifice, as in, I'm not sure. Phil really wanted Nike in the end. And third, go read the biography of Mike Tyson. Again, probably an awful human being, but it'll teach you about who to trust.

• 30:30Speaker 02

  As in, if you as a single individual can assemble three hundred million dollars and everybody tries to kind of take it away from you, how do you figure out who are your friends, who to trust? Those are three books. Sorry for the extended sixty seconds.

• 30:42Harry Stebbings?

  No, I love those suggestions and I I haven't had two of them before. So I look forward to to reading them, especially the first one. He sounds like a delightful human. Tell me, if you could do the X dot AI journey again, what do you know now that you wish you'd known at the beginning?

• 30:56Speaker 02

  I would spend less time on building the first models. As in, none of them survived anyway. And I would spend more time in trying to define what data to collect and how to label it. Two, I would have leaned into a mix of UIs quicker. Not have spent three years leaning into only the conversational UI, but have figured out where and how far can it take me? And when do I need to mix some button or some other element into it? Those are certainly two very kind of clear things I would have changed.

• 31:28Harry Stebbings?

  And then I want to finish, Dennis, and I'm super excited for this one, given the exciting news tomorrow. What are the next five years for you and for X dot AI? Paint that picture for me.

• 31:37Speaker 02

  So here's what I dream of, and I think I told you before, I live down on Wall Street. I can see the exchange from my kitchen window. As in, there's not a company going public for where the thirty by twenty meter banner is not in my face. So what I want is some Dropbox story for where they spent ten years and kind of certainly figured out how to become a standard for saving files in the cloud. I just want to spend ten years and become the standard of how to set up a meeting. As in, if you look at your calendar in five years, whoever you are, at whatever level, and those events weren't inserted by me, then I've still got work to do. And I would love along the way to have a big ass blue banner saying X W I down on the exchange.

• 32:20Speaker 02

  Then I'll invite you, we could do a high five, and I can go home from there. That's really what I want in the next five years.

• 32:27Harry Stebbings?

  Well, I'm gonna hold you to that. You've said it now to two hundred and fifty thousand people. So they all hold you to it too, but Dennis, I couldn't be more excited. I cannot wait to sign up tomorrow. I will be ready at the computer. So thank you so much for joining me again today.

• 32:39Speaker 02

  Thanks, Wilson. Thank you very much for having me again.

• 32:43Harry Stebbings?

  Now, a couple of closing notes. I do want to say that I have absolutely signed up to X.ai and I'm absolutely loving it. And then, secondly, Dennis is such a special member of the ecosystem and I cannot thank him enough for coming on the show. Likewise, a huge hand to Brad and David for the fantastic question suggestions. I would love to see you on Instagram to show all things behind the scenes here at the show. You can do that on Instagram at HDeblings1996. It'd be great to see you there. But before we leave you today, and I want to spend a minute to talk about Brex, the first corporate card for startups. Brex founders Enrique and Pedro built a payments business in Brazil, but found themselves rejected for a corporate card when they were in Y Combinator. They decided to build Brex with instant online signup, no founder liability required, and limits 10 to 20 times higher than standard cards. Pretty

• 33:27Harry Stebbings?

  incredible, I know. And you can sign up for Brex today and get fees waived by entering the code Harry during signup. Honestly, it really is such a special service. And with Brex in place, we now need a team to really use the cards. And that's where Terminal comes in. Terminal is a startup that appreciates hiring amazing developers is really hard. Plus, it's even harder if you're only looking in a 25-mile radius of your office. So Terminal is your dedicated partner in rapidly standing up world-class remote technical teams. How do they deliver both speed and quality? Well, Terminal does this by focusing on everything necessary to successfully source, set up, and support these teams. From physical elements like beautiful workspaces and equipment to ongoing resources like HR, payroll, legal, professional learning and development. But don't take my word for this. Take the word

• 34:12Harry Stebbings?

  of Eventbrite, former 20VC guest Hims, and DialPad, all of whom customers and lovers of Terminal. And you can find out more today at Terminal.io. Finally, we now have the team in place. So as a founder or operator, your next crucial job is people operations. That could be hiring execs, developing managers, retaining that top talent, and building a high-performing culture. And that's where Lattice comes in. Lattice is the number one people management solution for growing companies, helping the likes of Asana, Reddit, and Cruise build a really strong company culture. And with Lattice, it's easy to launch 360 reviews, share ongoing feedback, facilitate one-on-ones, set up goal tracking, and even run employee engagement surveys. And Lattice is the only solution that combines both performance Employee engagement, so operators can really make sure top performers are happy.

• 34:57Harry Stebbings?

  And Lattice is giving away three months of Lattice free to 20 VC listeners. Just go to lattice.com/20vc, that's L A T T I C E dot com forward slash 20 vc. Build an award-winning culture with Lattice, the number one people management solution. As always, I so appreciate all your support and I cannot wait to bring you an exceptional set of episodes next week.