The speaker begins by framing life as a fleeting opportunity, choosing "interesting adventures" over comfort. This philosophy extends to business, where early bets on companies like Infinitus and Weights & Biases provided first-mover advantages. However, he argues that while initial speed and execution are vital, long-term success depends on innovating and "changing the rules of the game," as seen with Amazon's creation of AWS. Competitors can learn from mistakes but cannot instantly replicate deep foundational work. Reflecting on his startup journey, including ventures like Mogad and Choice Vendor, the speaker values the internal conviction of discovering market "secrets" and the profound fulfillment of entrepreneurship, despite its stresses. He concludes that career decisions should prioritize enriching experiences and learning, as life's brevity makes the pursuit of mere stability or wealth less meaningful.
Most of the universe exists without me. Most of the universe will exist without me. The span of my lifetime is like Like this, right? It's like infinitesimally small, right? So the analogies here in a dark room is just pitch black There's one window the wind blast the window opens it stays open for a second and then what slams a backsearch, right? Only thing that matters is is the scenery interesting for the millisecond that your windows open, right? And so at least for me that's how I run my life, right? So it's like if I'm given the choice between an interesting adventure and like comfort and stability I will pick the interesting adventure Hi, I'm Juben operating partner a Kleiner Perkins and I'm excited that you're tuning into grip The goal of this is not for it to be a highlight reel of how successful my guests are rather a candidate exploration of how art It is both personally and professionally to create build and scale world-class organizations If you're a fan of the show, please subscribe, leave a review and make sure to follow us on LinkedIn or Twitter. Thanks The bet that Ilya made and then that you made on infinitus Was contrarian at the time. Maybe it wasn't contrarian, but it was early Now it's the moment this bet was years ago and now the market has caught up and So when you feel that and you already have very well articulated product market fit you start to think oh my god because then Everybody else is gonna start ankle-bike. Yeah, but they can't move as fast that we're seeing the same thing in weights and biases We're like it's all the years of work prepping every other competitor has to replicate that shit You have that lead time that you can keep pushing and it's about not overplaying your hand I think you think so you want to be aggressive, but you don't want me stupid But do you not think listen if either of us had the perfect answer to this would be probably not doing the best Yeah, exactly, but don't you think that at some point The only advantage you have is speed of distribution No, so the advantage is speed, but it's not necessarily speed of distribution The counter-take of this is Bob Muglia who had on like two weeks ago who is a snowflake founder. Yeah, of course. Yeah, well CEO, but yeah That's right man CEO. So funny because they just conflate the two now who is the CEO? He was like look every company is different every market is different So it's actually very difficult to paint broad strokes on anything which is why I think Venture capital is get honestly a bad rap because they just try and reapply one learning to another and the companies are just very different But his point was we knew At some moment that the only thing that we had was speed But I think snowflakes a different story right because snowflake you were the market was known Amazon already had a product it was a sleep of the switch But the minute Amazon woke up snowflake was fucked and so snowflake had to be big enough before the hyperscalers woke up Because they already had something the strategy in that market is very different like the strategy is basically like an Innovation of like snowflake seeing that market to be bigger than Amazon thought it was but the market existed before him I think in the infinites case it's a fresh build no one has this shit like everyone is building it from scratch Yeah, the person running after you is gonna run faster than you because you've already like kind of like laid the track or whatever But they can't like teleport they still have to run not thinking clearly about the next step Can also be a failure man. That's fair But the person that is chasing you down the company that's chasing you down They can't teleport but they can learn from your mistakes 100% and some of those mistakes could be distribution Maybe you decided to go top-stand when you should have gone bottoms up some of those mistakes could be architectural Some of those mistakes could just be features and functionality that they see that you don't run it That's that's why I think I think a competitive advantage is speed for sure But it's not necessarily speed or distribution Yeah, if you pause for a second and make the right architectural choice which feels slow but actually is really helpful It doesn't seem Fast at the moment, but then you know helps you leap forward on the next bit Do you think there's a tipping point where it is speed of distribution? I think it comes in spurts In general like every big business like even massive businesses like Amazon or etc Like constantly reinventing themselves by like changing the rules of the game They're not just playing the game faster or better and in fact the companies that tend to do that for too long without Rear-contacting like end up in kind of a like a pretty shitty Denon spot and then they have to like do some like innovation to like pull themselves out of that hole We're seeing it with Oracle right now for like the first time in like 30 years And so I think it's like speed of execution for a while and then it's like you got to change the rules of the game Otherwise like people eventually like have all the same weapons you do and then it's an astute fight Yeah, Amazon did this by like AWS right? It was just like okay, you could be a better and better and better marketplace But eventually somebody else was gonna catch up and you were just gonna fight the marketplace fight with like eBay and Etsy and whatever The then they changed the rules of game and now it's like oh we didn't think about like selling compute You know, it's like they created completely new categories. Yeah, I think that's fair When I was at my previous startup Before it got acquired by Paul Alto There's a bunch of reasons why things probably ended up happening the way that they did But we were first to Securing public cloud infrastructure, which was like so sexy of a place to be and Everyone's just moving workloads to the cloud and everyone's screwing up leaving S3 buckets wide open to the internet and It was freaking everybody out and so it was basically a Default standard that if you're going to the public cloud you had to do something now Maybe that something was native AWS services, but maybe you're on multiple clouds or maybe you're on Azure whatever it is And I remember probably around the 10 to 12 million of AR We started seeing this new competitor that we'd never seen before and It started with us losing a deal. I'll never forget the deal. I'll never forget the deal and That was the first time where I Remember going to the CISO and asking why did we lose the deal and There was some fundamental architectural decisions that this company made they were sub like two million of AR they just watched what we did and so quickly they started winning a sequence of deals and It's weird because as I reflect back on that time the treadmill had slowed down for us already we were not iterating in the way that we used to and It completely caught us on our heels and we were very flat-footed and I think that was a catalyst to ultimately end up selling I think maybe slack had a similar moment Yeah, I think slack well I mean listen like my wife was early at Slack so I've seen this from like the close bit. I will say it is very hard to compete with the Microsoft distribution cannon. I think if slack had lost to anyone other than Microsoft teams or whatever and it's not even clear that they lost right? It's just like if the main competitor that came out of nowhere wasn't like oh We'll just bundle this in with office the most widely like distributed pieces of from the planet. I might say that's true And the honest truth is like you know you've built this awesome bazooka and somebody rolls in with a Flax of tanks. You're like oh shit You know like where did they build these tanks? I had Scott cook on the Intuit founder. Yeah, and he was relaying a story to me when he was talking to John door Who was on the board at the time it was when? Intuit was gonna sell to Microsoft and Scott was conflicted on whether or not he should do it and John was like look only damn fools getting the way of a runaway train. Yeah, that train is obviously Microsoft But listen like you know Facebook had that offer to chose to decline and build a massive business that continues to To evolve I think the difference there is they continue to reinvent themselves if Facebook had just the Facebook Flagship app today it would be a much different company than what's up an Instagram and threads and VR and Genie and all the stuff they like it's not just running fast It's pausing and being like okay What's the unanticipated next step that our competitors that are competing with us on the current business aren't thinking about But we have the wherewithal the pause and be like we're not just gonna win this game setting up a board over here That they don't even know about yet and we're gonna start playing that game by the time they realize it We've gotten like more headroom there. We can do this on a smaller scale of weights and biases like we built this experiment tracking solution like 2018 Today there are a bunch of other experiment tracking competitors that compete with us and we see them in deals But for the last two years we've been building production monitoring and customized visualization solution that we just released and all of those Companies that are doing the experiment tracking stuff. They're looking. They're like oh shit We didn't know that was also happening. It's like we've been fighting this like chess board over here We didn't know these guys were constructing this other chess board on the side that actually might be the next act of the business That no one else was ready for because it was happening Altaniously, isn't it fun? So you were a partner at Cotou. Yeah, and so you were on the venture side then before that You'd sold four companies and four I started four companies. I sold two. Okay, okay One's still going one one the way of Dodo. It's funny. It's the one we're like
I care, I mean, I care deeply about all the investors and my companies, but I have this like deep affinity for Michael Deering who invested my third startup, and it's the only one where I lost all the money and I was like, oh man, this sucks. But anyway, started for company Solter. So what I was gonna say, and actually wanna talk about some of the experiences, 'cause I think they're very instructive, isn't it a cool feeling being at a startup, feeling like you have a secret that most of the world doesn't actually know yet? - It is the best feeling. And like at a startup or in VC, like I feel like I live for that feel, like I like money as much as I like power and success as much as the average bear or whatnot. The thing that makes me the happiest is like figuring out a secret about the world before anyone else, people thinking I'm an idiot, and then two years later being like, oh shit, you were right. - But the period of EDSC, that's the hard part. You gotta have the internal conviction, otherwise it's not a secret. You really feel like you were clued in to a bit about the way the world works that people aren't seeing yet. Like I think if it's too consensus, it's not interesting enough. Obviously, ton of my predictions are also wrong. But I've had this in a gamut of areas. So like betting on weights and biases in 2019 where like ML, there were maybe 10,000 ML practitioners total in the world. Everybody was like, this seems like a niche business. What are you doing? Now it's like a unicorn on a roller coaster. But also like at a Twitter argument with Stuart Butterfield because I was like, Trump is gonna win the 2016 election. And I bet this in, I don't know, I go but look it up in Twitter, like at least two years when he was like not even the Republican nominee. There's a public thread that's like dated on Twitter of the stuff and everybody was like, this is crazy. Like you're totally wrong. America's not gonna vote this way. It's I don't like, I have strong conviction that this is gonna happen. And not that I like Donald Trump, by the way. Like let's just be super clear. Or COVID, right? I remember convincing, like having a conversation with my partners at Koutu being like, listen, we should buy like work from home stocks and we should like stock up on masks. And this thing is gonna go for like a lot longer than anybody expects. And everybody was like, no, he's like, dooming or whatever. And I can walk you through the arguments of the time where I like, I thought that was the case. But those are the funnest parts. You can call me all kinds of names. I know I'm right. And then it's like, it takes a while for the correctness to manifest in those satiations. Because if you were too obvious, it'd be too obvious. The four companies that you're involved in starting, how much do you think looking back external forces influence the way that you made decisions in hindsight? I would say some yes others know that we can get philosophical 'cause I do Buddhist meditation as well. Like I'm not sure the difference between internal and external forces. And like I'm not sure that necessarily that, I think the world is interconnected in a pretty intrinsic way. What is the boundary of an internal versus an external force? Go far enough and everything's an internal or an external force or both. That kind of gets like too hypothetical. Like let's get back to the concrete bit, which is like, so I think in the case of Mogad, the first company, I would say the impetus of starting it was mostly internal. I wanted to start a company when I was in business school and I had no good ideas and no good co-founders. And so then I went to Google but I wanted to start a company. And so I was working on pet projects with friends on the side like stupid shit. And then through those pet projects I found this guy who liked I really liked and we both wanted to start a company and then we kept working on pet projects 'cause we didn't think any of the things that we were starting were really companies. And then at some point we kind of decided like the only way we're gonna do this is if we burn the bridges. And so he left this job I left mine and we had no startup idea but we're just like, we're gonna hold ourselves up in brainstorm stuff. That was the impetus of Mogad and actually it was the fourth or fifth idea. We tried a bunch of stuff that we were just making little prototypes and we're like, nah this seems stupid. We eventually iterated our way to something that we wanted to use, that we wanted our friends to use. It started out as building something for ourselves and then it kind of grew from there. So I mean there's always external force. Like I wanted my friends to use it where like is that an external force kind of yes, probably mostly no. You know I contrast that to Choice Vendor where I was in EIR at battery ventures. I was sitting in on pitches. I was seeing other companies in a certain pattern be successful. I had advisors who were like, I built a marketplace for this and it worked this way and I built a marketplace for this. I built this way. I had an internal need which is like when we were starting Mogad I had all these questions like how do I find a lawyer and a marketer and all this other stuff. But it was like not the only problem. I basically kind of like retrofit this pattern into my own need. And so I feel like that one was kind of more influenced by external forces where I was like, oh, if I were to start another company I would have all these questions about like who my B2B vendors should be. And then oh I'm hearing these marketplaces are like good businesses. Maybe I should build a marketplace for B2B vendors for startups, right. Choice Vendor was born. But like it felt less of like an organic like, oh I built something like truly for myself and more like I had like the kernel of a need and then I just slammed this like successful pattern into it. And once you sold Mogad to. We sold it to ice-goot while ice-goot was getting bought by Qualcomm so it was kind of like a fish chomping situation, you know, like that graphic, you know, the little fish eating the little, you know, anyway. And were you made after that? No. That acquisition was like basically for like a bag of potato chips. I mean it was like my co-founder and I spent almost two hours with a CEO of ice-goot trying to convince him that he didn't need to buy us. Like we were just like, oh this is a little bit of technology. Like there's no user base, et cetera. Like this is like you shouldn't buy this thing. And actually like I think it like it affected him in the reverse psychology. We're good friends. So like a joke about this. But like I think it affected him in reverse psychology terms. Like I don't know, he paid us like a couple years of worth of salary. It was like a small amount of money. But did you, did you, did you, you caught the bug? I was hooked. Yeah, that's for sure. Like my worst day in Mogad was better than my best day at Google and Microsoft. And like that's saying a lot. Because you left Google at the heyday. Yeah, I mean, listen, like I think there's something about charting your own destiny, whatever that means, right? Because I also don't necessarily believe that we have free will and destiny anyway. Like the idea of just like feeling like you're a protagonist as opposed to like a soldier is really fun. It's really cool. And I was hooked. And I was just like, you know, the day to day of that first startup we meet every mistake in the book. We had co-founder conflict. We had a third co-founder who was a very close friend of mine who ended up hurting ways with. And I was like a difficult event. We're now friends again, but there were months where we weren't friends. And despite all those things, I was like, oh man, this is like so much fun. Like why have you-- Do you think you look back at that retrospectively with Rose-colored lenses? No, I literally knew when I sold that thing for bag of potato chips that I wanted to do it again. Had I just stated Google for the period of time that I did Mogad, I would have made like five times more money. And I was like, I don't care. I just want to do this again. It's interesting because that pattern continues to show up basically throughout every career decision that you've made. Yeah, because I think-- Here's my perspective on life, right? The span of my lifetime is like this, right? So the analogies here in a dark room is just pitch black. There's one window. The wind blasts the window open. It stays open for a second and then it slams up extra. Only thing that matters is the scenery interesting for the millisecond that your window's open, right? And so at least for me, that's how I run my life, right? So it's like, if I'm given the choice between an interesting adventure and comfort and stability, I will pick the interesting adventure, right? In work, happily married, love my wife, love my dogs. Like that part is like the rock, right? But in terms of career choices, I'm like, oh, if a window opens and I can learn something really cool or experience something really interesting or beyond the edge of some curve, even if I make less money and less have less power and whatever, like I will pick that thing because it's just like, why not? I'm gonna be gone in like the blink of an instant. I can't take all this cash with me to the grave. (laughs) But the problem is life is an experience that way. Meaning when you're going through a couple years worth of startup life as an example and let's use your metaphor of the window being open for a second. Yeah. It feels longer than that. Yeah. Yeah, I know I told you. Like the lived experience is much more elongated when you're living in it. And so I think it's easier said than done. I agree with you and I've like spent a decade of my life like stressed out on my mind, like working crazy hours and like we can talk about my psychology that contributes to this, et cetera. And yet still despite all those things, right? It just feels more fun and more interesting. Like as a kid, I remember having this conversation with my parents and my, I think my mom and my dad was like, "Oh, why can't you just be happy like being an ordinary child?" And I was like, "Oh my God, that's like the worst insult I've ever heard." I will take anything except like an ordinary life. Like please don't give me an ordinary life. Like that seems like so bland, right? And so like if you take the unordinary path, it's gonna come with like some real downsides, right? But like when you're in it, it (beep) sucks. But do you consider yourself a happy person? Do others consider you a happy person? (laughs) So I think the answer to the latter question is it depends on how well they're doing.
know me. I would say if you don't know me well the answer is very clearly no. One I present kind of like resting bitch face or whatever. I have a coltone, I'd speak fast, I kind of like don't smile a lot, etc. I think if you know me better, it's a mix. I get affected by stress and anxiety like a decent amount and like in those holes I'm less happy because just stress is overwhelming. But I think generally like I have some really happy points. And then I think for myself it also depends on the context. Like I actually think that my emotional range feels narrower. And so like in some sense I'm like less super happy and less super sad. Yeah that makes sense. Which I think also you know is part of this like yeah I'm in a down spot and I'm kind of down but like I'm never like crazy down or crazy up. Continuing with your metaphor of the beauty of the scenery. Yeah. Looking outside the window. Yeah. You could optimize for that. Which is what you've chosen to do. Yeah. There's a school of thought that says maybe there's a cohort of people that don't even really notice the window opening or closing at all. Like they're actually just kind of okay in the dark room. You know like actually the dark room is the thing. Yeah for sure. And I think by the way like everybody should run their life the way they I'm not suggesting that there's like an optimal way to yeah to run the life. I just think that like my I've made decisions based on like I came across this quote actually in business goal like this like regret minimization quote. I don't know if you've heard this thing this I think it's attributed to go to I'm not sure if it's actually him who said it he said something that's like regret for the things I've done can be tempered with time. It's the regret for the things that I haven't done that's unconsolable. It's almost like kind of a ridiculous quote right because for everything that you choose to do there's something you don't do right so there's always like a regret for the thing that you've done and the regret for the thing that you haven't done. But then the question is just like okay which thing would you regret more not doing do that thing right at least in my own mind right everyone has their own kind of like value calculus like that's mine I like it it might be completely suboptimal globally or for other people but I'm not them they're not me who cares like what's interesting is so you did choice vendor after Mo Gad after Mo Gad exactly you did that for like two years yeah and I read a quote a some news article yeah or like who must be walking away from a larger amount of equity is leaving the company for personal reasons we've also heard that LinkedIn CEO Jeff Weiner is not particularly thrilled about this latest development Weiner himself admitted that choice vendor was primarily a talent acquisition on LinkedIn's part yeah for sure yeah I mean I did leave a I walked away from them like it was in a huge win for you I mean it would have been if I'd stayed what happened my mom got sick that was one factor I think the other factor is I think I didn't like working at big companies you know we sold this thing kind of on the hope of like oh this would be part of LinkedIn and it was gonna be awesome and LinkedIn is a fantastically well-run company and I think everybody there on the executive team is awesome I just didn't enjoy the day to day and he kind of goes back to like I'm being a protagonist yeah not dissimilar from your feeling on Google yeah exactly I kind of felt like I was back at Google and then I think I probably would have stuck it out a little bit longer but then like some personal stuff happened at the same time and I was like oh I've never prioritized my personal life I'm gonna go to France and spend like a few months with my folks and I think I asked for a leave of absence and they're like no you can't you just sold this business and I was just like whatever you can I just and how old were you ish let me think that was 2011 born in 78 to 31 31 yeah you're still young yeah and I kind of thought I was like well listen I can make a bunch of money by working at LinkedIn for a bunch of years or I can go spend some time with my folks and then make a bunch of money by starting another company but did you think that maybe did the equation ever cross your mind of like look couple years here kind of like see through the vision of choice vendor give myself a buffer yeah it give myself a little bit of latitude here yeah like the inevitable was still you starting another company for sure it did like maybe fund the company yourself yeah whatever right I mean and by the way like you know between us right like I made way less money in the time that I was out starting happiness engines which is the company that failed then if I stayed for the same amount of time at LinkedIn so from a cash maximization perspective you made less money yeah oh for sure like if I had just stayed at LinkedIn for the two years that I built happiness engines I would have made way more money at LinkedIn than spending the time doing what I close yeah not even close right I mean you probably lost money on happiness engines yeah I mean a little bit yeah but like the main thing was actually like the money like the opportunity cost of the money I didn't make a link to it right for sure but from a money maximization perspective mistake like clearly mistake yeah sure to stay right would I make the same decision again knowing what you know knowing what I know now I ask myself this question sometimes and the answer more often than not is I probably would which is kind of weird right because I learned a bunch of other stuff and I made a bunch of other friends I'll give you one perspective I met my wife shortly after leaving LinkedIn like I went to Paris and I came back and I met I sent something like that or like I met her we went on a date and then I went to Paris and I came back we started dating right if I stayed at LinkedIn I'm not sure what a matter right I was like kind of a different mindset I was like I've got no incumbrances I'm gonna go spend some time in Europe with my folks yeah it put me in a certain mindset that I wasn't in when I was working at LinkedIn and so like let's say I would have had like 10 million bucks or 20 million bucks more but not be merit and mercy like would I take that trade absolutely not I just wouldn't it's kind of like yeah okay I'm less rich than I would have been otherwise but like it's not the only thing that matter you know what's funny is we're a hundred and fifty episodes in at this point right like I've talked to a bunch of people and I'm trying to think as you're talking and I talked to all of them about career decisions what did you do why did you do it yeah do you regret it would you do it very very seldomly do I hear someone say that they regret the decision that they made yeah very rarely yeah and it's kind of got me thinking like if there is a reason for everything that whether or not we're rationalizing it because we want to minimize our regret retrospectively or whatever the reason when we look back if we rarely ever regret most of the decisions that we make in our life yeah then why the fuck do we care so much about every decision that we make in our life so here here's I think I think the interesting thing is like why is everyone so caught up in the anxiety of everything yeah I have an answer for you but I'm not sure you'll like it which is the yanda who left LinkedIn and met mercy and got married is a different human being than the yanda that would have existed if he stated LinkedIn and so explain well it's just I'm just a different person I like different life experiences different decisions different judgements different I would have been twenty million dollars richer I would have probably done different things hung out with different people met different friends like all this like if you actually could walk the tree on both decision paths the person you are in both of these outcomes is a different human and so the problem is before the decision you are the potential of both of those humans that's why we agonize right but after the decision you're only one of those people and you're like yeah I mean the right call I like who I am you know I never are gonna go to the counter factual be like I like the other guy that I quite a lot it's like I don't want to be this other person I like being me right and so I think it's like after the fact you look back and you're like all this thing that happened made me who I am today I like who I am today great calls I never want to be like I want to be someone else that sounds like a really deeply like unsettling view to have about like like you know there's there's aspects of myself that I don't like or whatever but like I wouldn't wholesale trade myself for for some other human being versus like before the decision you have this like oh no I have a chance to become two different humans which one do I want that's a really hard decision to make yeah and so are you saying that before the decision we appropriately weigh the options because we want to optimize for the best future self or for yourself yeah I think so I mean it's like past me trying to decide which future me deserves to exist in some sense that's a pretty heavy decision like imagine you actually like in the hypothetical imagine instead of like at the end of the decision somebody like shot you and they were like okay well whatever person material like you you get to materialize a new human and you can choose like LinkedIn yanda or like happily married yanda but then like you die but like one of these people like appears right which one do you like better that seems like a really heavy decision to bear on your shoulder with this kind of what's happening right like the yanda that made the decision no longer exists right only this yanda exists the yanda that say to LinkedIn also never got to exist from that perspective now I'm like yeah great call I like me you know I like existing so great great I think I have the coolest job in the world today and I'd say the way my life is designed
And right now is a lot of work. And I like it that way. It's good. And I'm pretty sure that when I look back on, if I was in your seat and someone was asking me, the question is that I'm asking you, which I often think about, because that's what I ask people, is this job is gonna be the coolest, most awesome job I've ever had. I'm pretty sure about that. And I'm also pretty sure that if I was giving myself advice, I'm going through this job again. And maybe I'm in this job forever. That'd be awesome. Is that I wish I gave a little bit less of a shit about more things. I wish that I wasn't so acutely cut by all the little things along the way, because I'm pretty sure in hindsight, my story is just gonna be like, that was a sick job. And I'm basically not gonna remember, it's like a bunch of windows opening in the dark, like sequentially over and over and over and over again. Yeah. And every time I look outside the window, if that makes sense. Yeah, for sure. And I'm quite sure that I won't, yeah, you won't remember all those little things. No, and I'm quite sure that I'll regret. I will regret not just being a little bit more laissez faire about more things. So maybe I feel the same way sometimes too, but I will, like, if this gives you any psychological ease, the person who is more or less a fair about those things, wouldn't be you, be someone else. Yeah, I think it's really well said. And so, like, ultimately, like you like being yourself. So like, okay, there's some downsides, but that's part of who you are. Like, you know, I have anxiety about work. It's like, well, the person who didn't, I might cure myself of that in the future, but if I didn't have it in the past, I wouldn't be who I am today. So it's like, it's part of what I, part of why this is. You already are. Yeah, it's part of not even where I am. It's who I am. Like, if I had not been anxious as a kid, a different human might or might not be sitting at this table. Probably wouldn't be sitting at this table be doing something else, different job, different, whatever, right? Like, I don't know. You think that anxiety was developed young and just stayed with you? 100%. Yeah. 100% Yeah, 100% developed young and stayed with you. Do you think you can shake it? Do you even want to shake it? I do want to shake it, or at least like, attenuate it a little bit. Can I? It's a good question. I don't know. I hope so. I think there's a certain point where too much of something is like, you know, you want just enough to something to get the value out of it and then not too much. And I think, like, I don't want to have no anxiety, because I think anxiety actually is quite productive, et cetera. But I think there's like, could I have like less, like, yeah, I think I would benefit from that. But I think I'm also like now in the mind state where I could reap the benefit of producing my anxiety without affecting my life in a way that I wouldn't have been, like 10 years ago. I ask because you say that you'd like to maybe reduce that anxiety, but the reality is every decision that you make throws yourself in the deep end of anxiety. I don't know if that's true. It throws me in a lab that could cause anxiety. The demons in my head, it's not in the environment, right? Like, there's tons of people who go through the exact same environment I do with the same level of like bias for action or whatever, without feeling necessarily like the process is stressed in different way. - But you're telling me that you're at Koto, great venture firm, cushiest job ever. I mean, like, whatever, cushier than operating. - But different, but also high, it can be a very high stress job. And I think that the issue with though is just like, I don't think if I were to flee and become like a goat herd or something like that, I would probably find a reason to be stressed about like the milk production of my goats or whatever, right? The demon is in my head, not in the world, right? I think the way to kind of do this is actually to take a high stress job and figure out a way to like process that productively as opposed to like fleeing. If you flee the problem, like falling. Which is like going to like a lower stress job. Like a categorically lower stress job. Like I don't know if that's the answer, right? Like that's not a way to kind of like solve the problem. There's a way to avoid it. Like I kind of want to solve it. I think the way to solve it is you put yourself in an environment that like would generate that behavior and then you work on it to handle it in a better way. At least that's for me, that's what I, that seems like a fun challenge to kind of take on. - I actually think that's pretty profound. I don't disagree with that. - I don't disagree with that. - At Happiness Engines, you mentioned earlier at the top of the show that you lost, you said a name, somebody's money. - Yeah, Michael Deering, I'm sorry Michael. You raised like what, 500 K total? - Yeah, exactly. - Total. - And Michael, who is someone important in your life? - Yeah, he's a mentor and he's like just a lovely human being. - This is startup number three at this point. - Yeah, yeah. - And it just failed. - First of all, how did it feel to lose his money? - Yeah, off, I mean, it still is a big regret. And by the way, he was lovely about it. He was like, listen, I have a portfolio, this should happen. I hope for you that you find like a next thing that you that excites you. Like he behaved in the way that like a dream investor behaves when a founder, like when a startup fails, right? Like this stuff happens, don't beat yourself up. You tried everything, et cetera, right? But from my perspective, I was like, oh man, this like person who I respect was given me such great advice throughout my life. For most of the other startups, like they got a decent chunk of money, right? And this one, nothing, right? And I was just like, oh man, not this one. Like really, this sucks. - Did you startup number three failed? - Yeah. - Now startup number one. Now startup number two. Start number three. This is when you're supposed to have all the skills. Tools in your tool belt, all the skills, you know, all the knowledge, your battle tested, were what happened? How did that feel? - Must've (beep) - It sucked. - It sucked. Yeah, it really did. Yeah, it sucked. - It was just been a lot of doubt. I just imagine that there would be seeds of doubt that get sown. - Yeah, it's interesting, 'cause like, you know, then I went off and started fourths, or clearly not enough doubt, or whatnot. But yeah, it just, like pretty bad autobiographical memory, like in terms of like vividness, and we can talk about that as well. But like, it was a really shitty feeling. And we also, like, we really did try, like, a lot of different approaches. And it really did suck. Like it was like, especially like ending the startup before it had been like, you know, pretty decent outcome. And it felt like this one was like a clever idea, and could be bigger, and it just wasn't. Fortunately, what I would tell you is, it failed because of new mistakes. So I think that's what gives me some comfort. Like it's not like the stuff that I learned in the previous startup, I just like then unlearned. It was just like, oh, turns out actually every startup. - But did you, were you convinced that we're gonna do another one after that? - Every startup I started, I was hoping it would be my last and I would just run that into the sun. - Oh, really? - Oh yeah, for sure. Yeah, yeah, yeah. I mean, I kind of, I still have a chip on my shoulder of like not having started a company that I still run. - Like you never, the idea of selling. - No, it felt like a failure. I mean, not quite as bad as obviously the one that really actually failed. But like, yeah, I think, you know, when I set out on these things, I was like, oh, cool, I'm gonna start a thing, and it's gonna, you know, either I'm gonna run it as a private concern forever, or it's gonna go public, kind of for a company, CEO, et cetera. And like, now I'm in my mid 40s and like, that dream is very unlikely to happen. Like, I think the closest I will get to is I will get to be a public company sea level executive on a really cool company that I joined, which is amazing, right? You know, I spent 10 years trying to chase that dream and I was like, oh, maybe I'm not that good at this. You know, I should go, I should go after a different job. - Well, the third one, the possible, sorry, with the fourth one. - Yeah, portable, right? - That's right. - Ended up, got to what, 150, like you got into some serious ARR here. - Yeah, yeah, it grew big. That startup also had like, its fair share of challenges. I mean, it's kind of interesting, like we started out. - It raised many, many. - Yeah, I think it's on series D now. I certainly, like I was there. - What was the last valuation? - Ish. - I don't know, close to a billion, if not a billion. - Like, yeah. - Like, it's a meaningless company here. - No, no, no, no, no. - Right. - And it's still going, right? It's still going. It's had its fair share of struggles, right? It's selling into industrial, into the industrial realm, which like, certainly in COVID, like certainly got some headwinds and me, but even before then, some headwinds as well. But yeah, it's a real concern. It's still going, you know, it's now on its third CEO. There's been issues, but also like progress there. I think will that thing be meaningful at some point? Like it, it very well, might be. Like it still definitely has a chance to be a significant business. - Why'd you leave? You were the founder. - Yeah, it's one of the three founders and the CEO. - You did it for four years. - Five. - Five years? - Yeah, yeah, 20, we started the business in 2013. And I left in late 2017. Yeah, it's about five years. Yeah, about half, like half the, whatever. I was there for about half the life of the company. Man, where did I leave? It's such an interesting question. I think there's a couple things. Like why did you honestly leave? - Yeah, yeah, yeah, no for sure. Yeah, there's a couple things. So like one, I'm a product and technology nerd. And so part of it was, we started out actually, like when we started the business, it was called wearable intelligence. We were gonna build like software on top of Google Glass for industrial workers. I could have cool tech, cool, etc. We ended up building like a pretty lucrative, but kind of meeting potatoes business, building checklist on iPads.
Right. The part of that business that excited me more was the kind of product innovation part of it, less the sales and marketing part of it. So already I had kind of doubts on whether like I was the right guy to run this thing. Right. And then on top of that, I had conflicts with both my co-founders who I think probably they had their own doubts on whether I was the right guy to run them. You guys talk about it? We did, but not productively. Why not? Hmm. That is a good question. I think we're just different enough people that we couldn't effectively communicate with each other. And do you think your doubt and their doubt was a competence based out that you weren't. Well, I think their doubt for sure in me was a competence based out. Like hey, this company is big enough now where we're not sure you're the CEO for the job. Correct. And then I think my doubt internally was honestly probably pretty similar. Like one, I'm not sure. Do you think they were wrong? Well, I don't know. I think. I don't know. Yeah, I don't know. I mean, they honest. Again, like the Yanda who was here before you today is not the CEO of that company. So like, in that sense, yes, right, they're not wrong, right? Like where they were correct, right? But at the time, I would tell you I felt like conflicting emotions. So the first emotion was, f*** these guys, I'm going to show them, right? But the other emotion was, I don't know. I don't love running this business. I don't feel like I'm in like my power alley of expertise selling software to giant oil and gas companies. Maybe they're right. And so I think it got to a point where it was just like they presented me with this like, oh, you know, we think you shouldn't be the CEO of this business. And realistically, if I wanted to fight it, I probably could have. And did one of them take the CEO job? No, no. So we had hired a. Which is like kind of. Well, usually you would think that. Yeah, but I think that actually made it more poignant in some sense. It did. We had hired. It didn't feel like a. Oh, cool. A cool, like you suck. I want to be the guy, right? Like we had hired a CRO before who had sold into the industry. Promoted him or her. Yeah, exactly. We had hired CRO before who had sold into the industry. Like new, head of roll attacks, etc. It felt like it became a more sales and marketing business. And they basically were like, hey, Yanda, we don't think you should be the CEO. Like this guy who was the CEO should be CEO. I was like, yeah, the guy kind of does seem like he knows the shit better than I do. Like here I am, like founder in a space that I don't really know. Because the question at that point was distribution. Yeah, distribution and winning in like complex like big whale, hunting sale. All my experience previously had been like in consumer businesses or in B2B businesses that were like velocity kind of SMB, like PLG type businesses, right? This was like a let's orchestrate the challenger sale of a giant oil and gas company, right? Which at the time I was just like, well, yeah, you're probably, you know, like this guy does seem like he knows a lot more than I do. And he seems competent and he presents really well to our customers. And even my co-founders are telling me this. And so like, you know, part of me was like screw you. I deserve this or whatever. And then part of me was like, I don't know, maybe the right. And honestly, I sat with it for a bit and I chose to kind of like go along with it, right? I was just like, hey, it seems like there's a lot of smart people telling me that I probably shouldn't be running this business for the long haul. So let's make a peaceful transition. I'm still a major shareholder. I want this business to be successful. It seems like this guy's going to build a big business up. It was very bittersweet. You know, it felt like, I don't have kids, but it would feel like a little bit like you've taught your kid and then you send them off to college and you're like, oh man, like, I'm so much more to teach them. But also like, I'm not the person that teach them the next thing, you know, like I don't know. Like it's that those feelings together. I don't know. I have two Australian shepherds. I hope I never get to that with my dog. So they are really smart. But yeah, that was like, I don't revisit that decision wishing I'd done something different. But I do revisit that time and still feel the bittersweetness of it. Especially I think afterwards because that CEO that we promoted probably didn't do as good of a job. Well, now you're on number three. Exactly. Yeah, exactly. Like, in retrospect now, I'm like, oh man, maybe I could have done a better job than that guy. You know, like, I don't know. Sometimes founders CEOs have that doubt. Yeah. And a lot of the time, it's like, well, maybe there's someone better than you as the CEO, maybe, but like, you have a lot of like domain expertise and like tribal knowledge of the business and the customer and you kind of got it to this point. Like, here's the funny thing, right? Like, and now I'm the CRO of an ML developer tools company. And I run these complex L cycles, like not in industrials. And I think I'm pretty good at it, you know? Like, actually, like today, I'm like, okay, with all the things that I've learned, like, we're closing deals with like pretty awesome logos. Like, you know, I have a sales team that respects me even though I like it didn't come up through a career in sales, etc. And so I project myself back and I'm like, oh, man, maybe I had all these hidden talents that I like didn't like play into. But at the time, that's not what I felt like. I felt like I was like, oh, I have a lot of self-doubt. And then I'm getting, I'm seeing a lot of that doubt, like reflected at me from people who I might not be like super close friends with, but whose like opinions I respect, I started business with them. And this kind of comes back to like I judge myself very harshly. So it's like if presented in an environment where I'm given the opportunity to just be like, oh, Yanda, you're not good enough. I'm like, I probably choose that option. And I'm like, you know, I totally that situation manifests itself. And, you know, we are, we are. But like, the funny thing is if I hadn't done that, I wouldn't have had the time at Coutue, I wouldn't have the time to wait some like, again, it'd be a different Yanda, right? So like, so like, am I glad I made that choice now? Yeah, I love my life. You know, it's awesome. Would it feel fun at the time? No, it was like awful. It's interesting because after those experiences, the three, the four, keeps saying three. Yeah. You want to Coutue? Yeah. Became a GP at Coutue. Yeah. Spent almost three years there. Almost four, almost four years. Almost four years. May of 2018 to July of 2021. So I can't do it. And when you were there, did you get the feeling that you had at LinkedIn and Google? No. I mean, Coutue's small and like tons of agency. Like it felt like building a startup for me. So you felt like the protagonist. Yeah. I got pulled into this and like the story's really funny because there's like all kinds of random stuff. But like, I got an opportunity to help start a practice for Coutue, right? The venture practice. Yeah, the venture practice for Coutue, which like didn't exist, right? It's like we started that fund in December of 2018 and like very clearly like Philippe and Thomas and all the folks that could do like very important protagonists in the decision of making that thing. And in fact, they had started working on the stuff before I joined. But I felt like I was like there at the starting block of this thing and had influence in like the strategy and the portfolio construction and the early investments and like was there in the LP meetings and wrote the first deck and wrote the like it really felt like we were starting a startup inside of Coutue and I was like one of the co-founders. Like I was not the founder CEO, but I was like one of the co-founders helping build this thing. It was awesome. It was like an awesome experience. Part of me is like we can go back like because I started angel investing after choice vendor. But I always been like a little bit between two worlds where I'm like, oh, I like operating and founding things, but I also like investing. Like how can I merge those two worlds and like that experience at Coutue, the starting experience. Like the founder of Adventure Fund, you know, like not quite, but like also like pretty close. Totally. And it was like, oh, cool. I get to do both of these things at once. Like what an amazing feeling. So yeah. Anyway. When Lucas, the CEO and founder of Wights and Bias, yeah, approached you to do the series B series A. Series A. Yeah. Well, you did it. You like it. Yeah. Yeah. In fairness, I know Lucas for like almost a decade. Totally. Totally. I think my long standing friendship with Lucas, along with my nerdiness and my love of AI, afforded me the opportunity to lead around. And can you give the skinny on what does Wights and Bias is giving you 30 seconds? What does Wights and Bias is do? Yeah. So we build basically like an AI developer tools platform. So if you think about, there's a new type of software engineer, the ML practitioner, and they are responsible inside their organization to build ML models. And so that could be the person building GPT-4 at OpenAI, but it could be the person building a drug discovery model at Genentech or an autonomous tractor at John Deere or a self-driving car at BMW or something like that. Their job, they sit all day like trying to build an ML model. They often work in teams building ML models. The practice, that practice of software engineering is sufficiently different from the practice of software engineering from non-ML, like traditional software, right, that it needs a new set of tools. So you're not using GitHub and debuggers or something like traditional debuggers to do this, work using a new set of tools. And Wights and Bias has basically built that set of tooling, like almost like the premier set of tooling for the ML practitioner, which again, when we did the investment in like 2019 or like January 2019, there were probably 10,000 of these people in the whole world working in organizations. And today there's like, I don't know, almost a million, like three quarters of a million of them. So it was like a new nascent profession. It just like happened. Yeah, it's the secret that you knew that nobody else did.
Yeah, that ML was like finally, I mean, the funny thing is like, you know, when I was 13 years old, I read this book on ML, like, so my father's a computer scientist. Retired not with computer scientist. I read this book on ML. I was like, "Oh, I want to do this. This is so cool. Teaching machines how to learn. This is amazing." And I remember my dad saying at the time, he's like, "Hey, Yanda, you should absolutely study computer science. It's an amazing profession." But like, stay away from this ML shit. It's always five years away. And he was right for 30 years, right? But somehow something felt like slightly different in 2017 that I was like, there's something about the way Lucas is telling the story and the customer calls that we've done and the market traction and the rise of data science and GPUs and cloud computing, the internet, like it felt like all the like somehow this all the puzzle pieces were like in place that like, it was going to happen. And the funny thing is like, you know, and like, it still took, they really realistically happened, I don't know, with the launch of GPD three and a half like a year and change ago. But it felt like the window was like, it's like now, like you want to build a business now to be ready. Then. Do you think we're in the middle of the hype cycle? If you put your investor hat on? Yeah, no. I think AI is under hyped still, which is crazy. But it explained. Well, I just think that we have an opportunity to build not just a technology, but like almost like a new being that is going to, if we play our game right, could transform like human productivity and solve a bunch of like human scale problems and give us more livelihood and more free time and like help us solve like really complex problems, all this other stuff, right? And he were seeing the early signs of it, but we're like nowhere close to like the rocket ship acceleration of it yet. I think in as much as we're seeing AI be super powerful today, like way more powerful than was a year ago and even powerful than it still feels like it's like every day it's getting better. And like I think that's you're still in the upswing of like the potential that this thing has. I think that's what's the most exciting is that the secret right now is I think most people think that like, oh, we've hit the peak, but I'm like, no, no, we're just like at the elbow of the jaker, like we're just starting the ascent. Those that are saying we've hit the peak. Yeah, which by the way is not that many people in our circles, you know, yeah, yeah, yeah, yeah, totally. Yeah, some officials maybe, but yeah, but they would say that because the it's improving like it's compounding exponentially in a rate that we've never seen before. Exactly. Any technology. And the question that people are asking themselves would be, can this continue at this rate? Yeah, well, not forever, but I think for quite a while. I think every new technology compounds at an exponential that we've never seen before, right? Like you look at like how long it took computers to go everywhere, right? It was like 20, 30 years, right? And at the time, people were like, oh my god, this is so fast. Like Microsoft is like Microsoft's logo is like a computer on every desktop. Like that's ridiculous. You know, and it's like, well, whoops, you know, they were right. That happened pretty fast. And then mobile started happening. Steve Jobs was like, oh, everyone's going to have a computer in their pocket. That's ridiculous. I was like, wow, that happened like four times faster than the computer. And then every one of these things always surprises us. I think in part because like these technologies build on themselves and also like the people building these things are like they grew up basking in the previous technology. And so they thought they come in like kind of prepped to like accelerate the next thing. And so I don't necessarily buy the argument of like, oh, this is like faster than last time because like, yeah, like everything has I think the crazy thing that's throwing folks off for this one is the technology is improving itself in a way that we haven't seen before. Yeah. Like it's that's the coolest part of it. Like it's with such a low lift of human intervention. I think it's actually a pretty decent lift of human intervention. We're just not seeing it. Okay. Maybe but compared to the previous. Oh, yeah. But I mean, look at the lift of human intervention to develop the wheel and then like less for the industrial revolution and then less for like shipping trade and then less for the telephone and like every one of these things has become easier and something like more leverage, right? Because the technology from the previous era provides the leverage to create the technology for the next era. So we're forgetting that we're building on the shoulders of these advances could not happen if Nvidia hadn't created the GPU if the internet hadn't happened, right? Like these things in the massive amounts of compute, massive amounts of training data and really novel architectures. The building blocks that enable this to be easy took also time to build and then those things took and the internet couldn't have happened without computers, which couldn't happen without electricity. Again, this kind of goes back to the start of the conversation like external versus internal forces like where do you draw the line, right? Like you go back to the creation of the universe, right? In some sense. But what I would say is like I think the reason it's easy is because it's important. It's like the tip of the iceberg on top of like all the stuff under the water lines. You made the investments. Yeah. And then you became a board member and you were friends with Lucas the CEO and everything. I understand that. But like that's venture. It's some degree like you develop a relationship with the founder basically every time. Unless it's like 2021 in which case, maybe not. But when did the idea of like all right, I'm going to go back into the arena. Yeah, of joining. Yeah. Creeping to your head. Yeah. So listen, I think that was probably one of the hardest decisions because I loved my job that could do. You know, I had this like amazing vantage point I was making. I think weight devices is one of many, I think now successful or the predicate successful investments, right? Including an infinitesit we talked about, but also like in abacus and raycasts and other companies, right? And I really enjoyed the investor job. And I think given a sufficient time horizon, I'll probably go back and do that again. At the same time, I go back to like 13 year old me like really wanted to do AI and happiness engines, the company that failed was an AI startup that failed because it was too early, right? And so I went on this walk with Lucas where he was looking for like another intelligent entrepreneurial minded kind of athlete to take an executive level role to do a set of things that I felt like, you know, my life experience, the good and the bad had like prepared me pretty well for. And part of it was like this AI thing that I've been waiting on for like most of my life is happening. It could have just as well happened 40 years from now when I'm retired, but it's happening now when I can still work. There's this company that I invested in that I where I know the people, I know other mission and super aligned with like how they want to help manifest better AI in the world. The customer base is amazing. It's just like this amazing vantage point to see and help transform this like next revolution in technology. And then I go back to like which thing would I regret more or not doing, right? Staying and helping Koutou make more investments or taking this shot at this thing that is like felt like a once in a lifetime opportunity that like if passed like another thing wouldn't manifest. And I struggle with it. And then ultimately I made this decision and I love this job. I love the Koutou job, but I love this. This is an amazing job. And it's more work and it's more stressful and it's I'm learning new things that I didn't know before and all of the above. And yet it's like the coolest job I've ever had. Now that you're the what's the I mean, you're a bunch of different titles. I mean, I'm predominantly the chief revenue officer though I joined a COO. The COO job was kind of like executive janitor or something like that. My promise to Lucas was like just give me the thing that keeps you up at night. Let me help you fix it. You know, there are many things that I'm bad at, but one of the things that I recognize that I'm pretty good at is I like to re figure things out from first principles like take apart the toaster figure out how it works pull it back together so works better, right? And so like I kind of like these problems where it's like give me the hairball problem and let me on hairball it. And in that COO role, I've run a bunch of different departments at Wets and Bises over the last like two years that I've been there operationally. But once a CRO a year and change ago and then again now as of like two months ago. And so I run like my predominant job as I run the good marketing. Yeah. Doing this job like not being the CEO for the first time in quite a while obviously the sands go to when you see the CEO today. Are you like a f*** maybe this whole time this like entire drive that I had to build start run maybe exit as the CEO was like somewhat miss got like maybe that wasn't my superpower for sure. I mean I think I'm a much better sea level lieutenant to Lucas than I ever was founder CEO before. Man that's a good question. I think one of the things that I would tell you is it feels like Lucas was put on this earth to make the lives of ML practitioners better. He did ML at Yahoo. He did ML at power set. He started a category defining day labeling company in ML that he sold for I think enough money that he doesn't need to work again. But then he just turned around and started another ML developer tools company which is Wets and Bises.
In retrospect, when I look at the greatest founder CEOs that I've seen, they have this like, I exist to make this thing amazing, right? I look at Mark, at Facebook, and Sergei, and Larry, and then Eric, at Google, and like, I don't know, we can just go through the list. Like it feels like there's this kind of like, this inner drive of like, oh, this is the problem I was put on earth to solve, you know? I never really had that. I like solving puzzles. I like when somebody's like, here's a giant mess, fix it. And I think that here's a giant mess, fix it as a CO, that might not be the right fit versus like in the role that I'm in today, like I get to do that all day, and it's stressful because they're a giant mess when they start, but like, man, it's really fun to fix them also, right? So we're like, here's a complex system. Like, here's a problem, make it better. And I think part of it, I thought that that was like a founder of Trader Joe, so I was like, oh, I see the world in the lens of like, I see problems as opportunities and all this stuff, but I don't think that's just it. Like there's, I think there's this like, drive for a particular problem that I think makes founder CEOs like particularly effective. And I'm like, give me a sufficiently interesting problem, and I will sink my teeth into it and like, really enjoy it. But not any particular like, I'm not like, oh man, there's this thing I think about at night all the time that I feel the need to fix. Like I'm like, I'm like happy to fix any sufficiently complex thing. - When you revbed back up to get into operating, after almost four years, did you change anything on the personal side? Life is very different. The pace of life is different. The way your calendar is organized is very different. Did you do anything different? - One, my wife and I got married in 2017. So we'd been married for like four years. I'm doing math right, made five years. I asked her for permission. She obviously would. - It was a team decision. - Yeah, for sure. - Because it's like, well, because it's gonna affect my hours and my attention and my stress level and all this other stuff, right? - Can you tell me how that conversation went? - Yeah, for sure. - I guess, can I tell you why I asked that? - Yeah, of course, yeah. - I think there's a lot of people that enjoy the show. Because I obviously, for obvious reasons, romanticize startups and company building. - Yeah, yeah, yeah. - And I get to talk to all the people that are building the companies. - Totally. - And one of the reasons why I wanted to talk to you was because you've seen and are very honest about the dark side of company building, which is that like, I say dark side, like you're not like-- - It's mixed. - You're not talking about how you just hit home runs on every single thing. I think that there is a hidden cost that comes with it that's very personal in nature. That's why I ask. - Yeah, so I've pretty bad autobiographical memory. So I think you've talked to Mercy. She has incredibly good autobiographical memory. So probably her recollection of this is better than mine. But I think it went something like, hey, darling, I'm thinking of taking this CEO role at Wade's and Biasis. I've known Lucas for a long time. The team that I've met is really great. I've sat there on the board for a long time. The cons are we're probably lapping order of magnitude off of our income. I'm gonna be more stressed and I'm gonna have less time to spend on personal stuff. The pros are like I really want to do it and like I'm gonna regret not doing it. And she was like, go nuts. We're here to support each other and that's why we've felt this partnership. And we'll go through the ups and downs and I'll tell you when you're too stressed or I need more time or whatever. And that certainly happened at certain points. Like she's been like, hey, you know, we need to spend more time together or whatever. Like it's, you know, she's a very good partner. And then that was it. I mean, she did the same. She was in Venture and she went back into operating. We had the same conversation on the reverse and I was just like, listen, like, life is not about collecting gold coins that we take to the grave. Like life is about living experiences that we want to experience. So go do it. Like the good and the bad, right? And so yeah, I'm curious. I mean, if you ask her the same question, I'm curious if the history is diverged. But yeah, I think it was like broadly. - Yeah, I think the answer that she gave or what gave is not to similar from that in the sense that there's a very clear right picture of what that means. And I think people in your life generally recognize that you live with a regret minimization framework and the challenge with that is that everything is that way. Right? And so if you always are minimizing future regret, then you're always taking the generally path that's harder, in some ways, and the riskier path. And I think that leads to a more action-packed and fulfilled ultimately life when you look back. But I also think that there's a wake that gets created like a ripple effect of the hard thing. - I totally agree. It's funny, 'cause it's also like, I think, Mercy and I have like very long conversations about this. I'm very grateful. I honestly feel like the biggest hack or luck in my life is to go through life with a great partner. In that regards, of all the things that happened or didn't happen, the thing that I'm the most grateful for having happened is having met Mercy, which again, it's a bit tied to like, okay, well, I left LinkedIn, left a bunch of money on the table, I was like, I don't care. I would take that trade to meet Mercy any day. I've heard my life and I have like few very close friends because the way I've constructed my life has spent a lot of time on work and I spend a lot of time thinking about work. And so I try to allocate my personal energies to like, mostly her, and then what remains to like a small set of very close friends. - I was just talking to someone about this and they were asking me about the significant others and partnerships of the guests that I've had on the show. And they just assumed that everyone was divorced basically. And honestly, when I started this, I always just assumed everyone was divorced. I just thought that was the cost of greatness. And I have been shocked at how many people are still in like very strong happily married relationships. It's undeniable. - It's a super power. - I mean, it's crazy. - It's almost like it's a prerequisite. Like I've almost come full 180 on this thing. - The funny thing is like, I think it is an almost a necessary for men. Women I think might be able to pull this off like without like supporting partnerships 'cause like I feel like they do more work in relationships than men do. I can't imagine doing what I'm doing now without like a happy partnership with mercy. Like I just-- - And you don't have kids. - And I don't have kids. Yeah. - I have two Australian shepherds which I don't know. - Yeah. - Kids-ish, in quotes. I don't know if kids make it easier or harder. We have this conversation. Mercy and I have this conversation all the time, right? So I think like that one's like TBD. But I think a happy partnership is for sure a superpower. I'm pretty pleased with like if you're like, oh, you know, I live in a nice house. And if you told me tomorrow like, you gotta lose your house, live in a two-bedroom apartment and like, fine, whatever, right? It was like, we live in a great city. It's never to go. If you told me tomorrow like, you gotta move to like, wherever, some hot and musty place. I'd be like, yeah, whatever, fine. Like, well, it's just, you know? It's like, oh, I have this great job. And you're like, ah, you gotta be like a laborer now. I'm like, ah, I'm all adjust. If you're like, I'm gonna take mercy away. I'm like, no, I'm gonna fight you to death. Like, it's like no chance. Like, that's the one where I'm like, nope, not negotiable. You know, like-- - I recently had Carl Sianbach on. - Yeah. - And it was Sequoia not too long ago to go back to operating. He came to see you of work days. He's like, I'm sure you know. And I was having a similar conversation with him about this exact same thing. And he had a conversation with his wife. - Yeah. - And she knew what that meant. - Yeah. - Like, she knew. Like, it's very different. - Yeah. - It's so cool. - It's very different life. - Yeah. - And she also knew, like, she could see the dog in his eyes. He's gotta go. - Yeah. - Like, she just knew it. - Totally. - Which I'm sure is probably similar to you. Like, you can just-- - Yeah. - You just know. At that point, what are you gonna do? Say no. - You can't say no. - Yeah, kids like that. - When the microphones turned off, and we were just sitting there talking, he was like, "Jubin, everybody's gonna f**king disappoint you. "Your colleagues, your friends, your family, everybody "is gonna let you down. "The only relationship that you just can't give up. "The one thing that you cannot underinvest in, "because you think you have this incredible community "around you of people that will support you "no matter what, through thick and thin. "It's not true. "It's just one person." - Yeah. - And-- - Yeah. - It's really stuck with me. - I totally agree. - I'd say really stuck with me. - I totally agree. - And I never heard it put that way. Like, everybody except for this person will really genuinely disappoint you. - Yeah, or at least, like, I think the bond that you have with a great partner is not replicable. I have great friends who will be there for me if you think of them. And I think the same is true in reverse as well. I've been there for friends in some of their darkest hours. And I think the same has been, I've been gifted that as well. But nothing compares. I think this idea of just like being going through this weird experience of life with like a buddy, the whole time, like from some point onwards, it's just awesome. against it really. And like,
You don't realize how much of a superpower it is until you find the right person and then it's just like, it's just absolutely incredible. What's the thing? Would you fight a bear for this or something? There's a lot of things where I'd be like, "Yeah, the bear can have my house and my car and whatever." I'm going to fight the bear. If the bear wants mercy, I'm fighting the bear. What a heartfelt note for us to end it on. I appreciate you doing this, dude. That's my adventure. I can't wait to see what you guys do. I'm really excited to see what weight and biases does in this space. Me too. I'm stoked for it. And thanks again for the honor of being on here. I mean, you're being mentioned in the same sentence as folks like Carl Eschenbach. I feel like I have some big shoes to take off. Dude, I thought you had something to say. And I thought you had something to say and unique. I don't generally get to have these types of conversations. I have a lot of conversations with people that tell me the up into the right retrospective narrative. You know? That's just not how most people's like careers and lives go. Yeah, yeah. I mean. And so that's why I want to talk to you. I'm in the middle of it. I hope it goes up into the right, but like TBD, you know? Yeah. I conclude these the same way every time. The first, are you all hiring? Absolutely. Yeah. What? Any key roles, any things that are top of mind for weights and biases? You know, I should have asked for sure. I know for a fact on the go to market organization, we're looking for strategic sellers. And actually honestly, sellers of any kind. I suspect though I should have asked our head of product and end that the same is true. I'd be shocked if you're not hiring across the org right now. Yeah, exactly. Yeah, exactly. If you go to 1b.ai/site, there's a jobs page with a bunch of jobs listed. I feel bad that I don't have them all memorized. But when you hear the word grit, what do you think of what comes to mind? Standing up one time more than the number of times that you're punched in the face. Yanda, thank you. Cheers. Likewise. That's it. Thanks for tuning in. Feel free to come back every Monday morning to listen to a new guest or go back into the archives when we've done more than a hundred episodes. This podcast is a Client Republicans production and the episode was edited by Eric Johnson from LightningPod. Thank you all.
Podcast Summary
Key Points:
The speaker emphasizes living life as an "interesting adventure" over comfort, using the metaphor of a brief window opening in a dark room to illustrate life's fleeting nature.
In business, early competitive advantages like speed and first-mover status are critical, but sustained success requires periodically "changing the rules of the game" through innovation rather than just executing faster.
Reflecting on startup experiences, the speaker highlights the importance of internal conviction in discovering unique market insights ("secrets") and the personal fulfillment derived from entrepreneurship despite its challenges.
Competitive dynamics involve both leveraging initial leads and continuously innovating ahead of competitors who can learn from early mistakes but cannot instantly replicate foundational work.
Personal career choices are driven by a desire for meaningful experiences and learning, prioritizing interesting paths over stability or maximum financial gain.
Summary:
The speaker begins by framing life as a fleeting opportunity, choosing "interesting adventures" over comfort. This philosophy extends to business, where early bets on companies like Infinitus and Weights & Biases provided first-mover advantages. However, he argues that while initial speed and execution are vital, long-term success depends on innovating and "changing the rules of the game," as seen with Amazon's creation of AWS.
Competitors can learn from mistakes but cannot instantly replicate deep foundational work. Reflecting on his startup journey, including ventures like Mogad and Choice Vendor, the speaker values the internal conviction of discovering market "secrets" and the profound fulfillment of entrepreneurship, despite its stresses. He concludes that career decisions should prioritize enriching experiences and learning, as life's brevity makes the pursuit of mere stability or wealth less meaningful.
FAQs
The speaker views life as a brief window of opportunity and prioritizes interesting adventures over comfort and stability, believing that meaningful experiences matter most in the limited time we have.
Speed is a competitive advantage, but it's not just about distribution; it involves execution, innovation, and sometimes pausing to make strategic architectural choices that enable future leaps.
The speaker learned that competitors can learn from your mistakes and quickly catch up, emphasizing the need to continuously innovate and avoid slowing down iteration to stay ahead.
Changing the rules, like Amazon did with AWS, allows companies to create new categories and avoid prolonged head-on competition where others eventually match their capabilities.
The speaker lives for discovering 'secrets'—insights about the world that others overlook—and enjoys the internal conviction and eventual validation when those insights prove correct.
Despite making many mistakes and earning less money than at a corporate job, the speaker was hooked on the autonomy and excitement of building a company, leading them to pursue entrepreneurship repeatedly.
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