Opening And Madhu’s Career Snapshot

Hitesh Chudasama 0:01

Welcome back to Career Journeys Revealed. Today's guest doesn't just build products and companies, he builds mental models for navigating change. We're joined by Madhu Chamarty. Madhu is a repeat founder, technologist, advisor, and a writer. With four successful exits and more than 20 years in enterprise software, his career spans research labs to high-growth startups with deep experience across Enterprise SaaS, HR Tech, healthcare, and customer success. Today he advises global startups and emerging venture capital managers while building human AI productivity platforms as a founding partner at HKMC and a founding team member at Learden. His journey includes helping grow Dynamic Signal into an employee communication platform that had an amazing $400 million exit, heading up customer success at Descartes Labs that leverages machine learning and cloud computing to provide actionable insights based on petabyte scale data. He later went on to be the founder and CEO of Beyond HQ, a distributed workforce planning company, initially seen as unscalable until it proved critics wrong by scaling up during the pandemic and ultimately acquired by Ladcast, a part of KKR investment firm. Throughout his journey, Madhu has played a key role in scaling multiple enterprise SaaS companies that serve Fortune 500 customers, as well as advising companies on the go-to market and growth strategy. Madhu is a technologist who loves to express himself through writing. His work has appeared in Forbes, Business Insider, Fast Company, and on the front page of Wall Street Journal. Titles and exits are only part of Madhu's story. In this episode, Madhu reflects openly on the inner journey behind the work, growing up across cultures and continents, learning to get comfortable with uncertainty, and realizing early on that meaningful careers are rarely linear. We dive into why hard work often matters more than raw intelligence, and how prolonged discomfort, those so-called troughs of despair, are often where the most important growth happens. We also touch upon how he thinks about decision making, risk, failure, perseverance, and AI, not just as a technology, but as a force that could give us something increasingly rare time. Time for creativity, relationships, and meaning. This episode is packed with tried and tested insights and practical advice that apply not just to careers, but to life more broadly. Han and I are excited for you to hear this one. Let's get into it. Hey Madhu, really excited to have you on our podcast. Welcome to the show.

Madhu Chamarty 3:16

Thank you very much. Thank you both, uh Hitash and Han for having me. Psyched to be here.

Han Yuan 3:20

Welcome.

Early Life Across Continents

Hitesh Chudasama 3:21

Thanks for taking the time to talk with us and sharing your knowledge with our audience. It's fascinating to see how your career has progressed and how it's truly defies straight lines. I mean, looking at the career, it seems like you've gone through different types of roles, especially uh you've been a repeat founder for four with four exits, early operator at our high growth SaaS companies, and a global strategist who has built and scaled companies across various industries. But before we go and dive into all of that, tell us a little bit in regards to who you were growing up and what shaped young Madhu.

Madhu Chamarty 4:02

Yeah, I love that question. Thank you. Um what shaped me? So maybe I'll give you a sense of my upbringing, and then that'll hopefully surface some insights. Um I was born uh in India to a uh very kind of academic family. Uh probably not surprising. Uh given given India at the time, uh my parents are both doctors, work took them from uh India to Saudi Arabia, from Saudi to Ireland, Ireland to Canada. And so they were always away. Uh, ever since I was a three-month-old baby, I was handed to my paternal grandparents to be raised while parents finished up school. So as long as I did well in school, I didn't have to learn any basic life skills. So I learned how to use the rice cooker when I was 21. Um and the washing machine also when I was 21. Um and uh that academic bent or the intellectual bent meant that I was uh sort of a bookworm and and just the pursuit of knowledge was a reward in itself. So that definitely continues to date uh um as a as a characteristic. And then I was also um the only male child uh and I had maybe like eight or nine girl cousins growing up. So I was the older brother for so many uh uh so many, uh, and then they're all girls. So there was a sense of responsibility that you can only do what you want to do after everybody else had done what they want to do. And that continues to this day. I I tend to want to take care of the room or the venue or the group that I'm with uh before I prioritize myself. And sometimes that's you know great, uh, but sometimes that's self-detrimental. But these are a couple of characteristics, like pursuit of interesting things that challenge you mentally, and then make sure that those around you feel that they're um taken care of uh are probably the two traits that I seem to have kind of captured as a result of watching people around me growing up.

Hitesh Chudasama 6:15

Nice. I mean, reverse from a career perspective, if you could just maybe walk us through what are some of the different things that you've actually have had, you know, opportunities to go ahead and work on.

From Stanford To Startups

Madhu Chamarty 6:28

Yeah, absolutely. Um I think you said it well, Hitesh, that uh it defies straight lines. And as I'm sure many of us will agree, uh narratives are built in hindsight. And so they all sound nice and polished when you describe. But I'll I'll kind of speak to it not from looking back and giving you nice sentences, but instead what actually drove me at that point in time at various times. Um I so I finished my undergrad in Ireland. Um, I was the the one or two, I should have one other friend who's also Indian who happened to end up in Ireland. So we were two brown kids in a class of 200 engineers who were all extremely white and extremely Irish. And so um that was exciting and built a lot of friendships, et cetera. And then I didn't really know where to go after undergrad. It was electronic and computer engineering and math and lots of, you know, uh getting good grades or not so great grades, but the pursuit was very, very fun. And because I didn't know what to do afterwards, all my friends were thinking about, uh, let's go into banking, IT and banking. So London, the financial district in London paid really well for engineering graduates from Ireland. And so that's where people went, and I wasn't quite feeling like it. And I was like, oh, I'm just gonna go to grad school. Uh everybody's supposed to go to America, so I'm gonna go to America. And uh ended up uh somehow by some miracle uh at Stanford. And so um after that same problem, I was promised this path of unlimited potential when I was a student, like you can conquer the world and you can do great things. And but then every job felt like it's a a very, very um closed-off kind of quarters where you're just one of many people. And so I struggled with my first couple of years uh being uh a sort of a at a boutique management consulting firm that planted me at Microsoft up in Seattle. What I learned was interesting, but I just felt like the pursuit of uh impact and and uh making a mark wasn't quite evident. And so I was trying to run back to school again. Uh, got into Cambridge in England. I thought, this is it, this is my answer. I'm gonna go to academia. Uh, but then uh a family member at the time said, no, no, you should you should stay here and grow some roots and um not pursue, you know, uh ivory towers and whatnot. So that prompted my work into uh startups, and it was completely accidental. A friend from college said, Hey, there's this company that's doing interesting things. Would you come join join me? And that kicked off what is now 20 plus years uh in in pursuing kind of challenging environments where you have to grow in 50 different directions with very little guidance. And the next morning you have to wake up and do the same thing. So comfort with uncertainty, comfort with uh uh uh sort of rapidly moving targets, uh, and the promise of great scale if you can get things right, uh, really kind of spoke to that continuous pursuit of interesting things part of me. Um, maybe it's so C D ADHD, maybe it's something deeper, but um, that's sort of what led my career uh through multiple companies and different industries. There was always a key theme of how do you do, how do you bring technology to provide some novel value to large, complex uh industries. There was so much challenge in that sentence to me that every time I took a role, it was just that. It's like, oh, this is interesting, this is interesting, this is interesting. Uh, without really thinking about any other impact of like, oh, maybe you should consider a better approach here. Maybe these guys are offering, obviously, uh paying you more, any of that stuff didn't really resonate. Uh, but looking back, I realized I was chasing that intellectual high. And if I can expand my comfort zone with a new skill, uh, that made it all worthwhile. So um, yeah, that that's uh that's kind of the pursuit I I I went through. And I'm happy to go into specific examples, but uh uh just wanted to set the stage on how I see my career today.

Han Yuan 10:57

Startups can can be kind of challenging though, right? Because uh in the pursuit of novelty, there's this incredible, effectively, trough of despair that every startup inevitably goes through. And I'm I'm curious, given your experience, um dur especially during this time, how did you how did you manage the trough of despair? Because it's it's easy to just give up.

Setbacks, Acceptance, And Long Slogs

Madhu Chamarty 11:24

Yep, yep, absolutely. And uh so my answer is probably not very glamorous at all, right? Or even noteworthy, but it is my answer, nonetheless. Uh it's true. Uh, I do think before I give you my answer, that we as humans love to paint the best possible narrative on an outcome or a situation that suits us, right? We always try to polish it. History is written by winners. History is also written by the winning perspective in your own mind. So it's always uh I always say that the human brain is an opportunistic bastard. It'll always try to optimize dopamine or or you know uh uh uh endorphins or or what have you. So uh having said all of that, um, my reason partly was that giving up felt like uh failure. Like I have this deep sense of judgment that is partly from coming from the continent of Asia and the upbringing that Indian households generally and a lot of Asian households generally have. Part of it is the less grammar one is if I left any job, I had to leave the country because I was on a work visa, right? So I was in this place where my the spirit of pursuing something novel, other than this trough of despair I'm in now, was not accessible to me. If I leave, I have to leave the country. So I the way I I I have uh told myself that in in looking back is this was a way for the universe to teach me the importance of patience and pushing through. It like the universe prevented me from leaving when things got hard. Partly I didn't want to leave because of my own, like I want to succeed and then walk away versus walk away when it's hard. But partly, even when I really got to the edge of like, ah, you know, F this, like I don't want to, I don't want to do this anymore. Well, what are you gonna do, buddy? You cannot go anywhere. And I could have, arguably, I could have really tried to find a gig or some other pursuit where my visa wouldn't have been a problem. But I kind of told myself that, and and partly it was objective. Like it is very difficult to go jump around jobs when you're on a work visa, especially 15 years ago, 20 years ago. But part of it was just no, you you are going to not walk away when things fail. And it's a it's an ugly feeling, right? It's it's not glamorous, it's painful, and you're kind of pushing through the trough of despair. There's nobody telling you, oh, this is just a stage, and then you're gonna come out the the the you ride the enlightenment wave over time. Maybe. Or maybe you'll just constantly always be the oh, it didn't work outside of startups. And I and so many brilliant people that we all know have faced that time and time again. They just ended up. I had a friend, I have a friend who went through three uh failed startups for different reasons. And I he would come to me and talk about them, and I would feel gutted for him. But then he went through three really good ones. Uh, and there's no other than luck, I can't tell you anything different. He didn't pick any differently. He wasn't a smarter person or dumber person. He just it just worked out. So, to your question, An, I think partly I was sort of trapped procedurally, and partly my own insecure ego was like, you can't give up now. Uh and it came at a personal cost as well.

Han Yuan 15:11

I mean, your last you know, statements around just entrepreneurship are um interesting because I I think we've all kind of noticed that in a lot of cases the individual comebacks are all uh predicated by setbacks. And both the setbacks and the comebacks are part of the the master narrative. Were there were there certain setbacks during this time that you felt like set you up for comebacks?

Inflection Points: Hard Work Over Raw Talent

Madhu Chamarty 15:42

Yeah, I think um there's a few different categories I would say, but maybe the top two that stay in my mind are uh there is a a few instances of prolonged setbacks that really played an influence because there was no way out for a year and a half, for instance, of this feeling. And that's when within that year and a half, there is the oh, I can get past this difficult phase. No, wait, I can't. Uh, no wait, I can, uh, no wait, I can't. And so if like the the the fight against status quo is beaten out of you sometimes, it's just gonna be hard for the next whatever period of time. So just accept it, right? And once I accepted it, some seemingly indeterminate amount of time passes, and you start seeing things are a lot easier. And then you realize, man, you gave up on fighting this uncomfortable feeling a long time ago. And that's amazing. And the the it was uh, I think is it the Navy SEALs or the Marines have this thing that they said they tell recruits they go through Hell Week, there's no reason in fighting this, guys, because tomorrow morning it's gonna suck just as much. And it's gonna suck again. So don't fight it, you know, and there's some there's there's a profound wisdom in that, uh, where whether it's Eastern religions or stoicism, the ability and the mental toolkit to accept what you have now is such an underrated skill. Radical acceptance, that doesn't mean that you're okay with it, right? You are just accepting if I have a headache, and I'm just gonna accept the fact that I have a horrible headache. It's gonna end at some point. I'm gonna try to take some tablets or massage my head or whatever, but I have a headache and it just sucks. And it's an extremely liberating feeling once you truly internalize it. So I feel like one period that taught me a lot was there were periods. Uh, for example, when I was running Beyond HQ, um uh before the pandemic, people thought saw the company as a as a as a sort of a services business. Hey, we're gonna help you figure out how do you open up a remote office. It's like, what's the software play there? After the pandemic or during the pandemic, where every company started thinking globally distributed, we said, oh, this is what we've been talking about. We're gonna build a piece of software that lets you evaluate locations based on their merits. And suddenly we were the new hot, new hotness. You know, I was in the front page of the Wall Street Journal, top 20 startups that are gonna be doing amazing things, same story, same person, same pitch, completely different market reaction. So that's another uh example of like if you feel like you can accept the current situation based on your conviction, based on your desire to kind of want to push through, whatever the drivers are. So that's one category of setback that I felt is um is really character building. Like it's just it's not a three-month, six month, it's like a prolonged exposure to pain. Uh actually is an amazing skill set to develop uh comfort for.

Hitesh Chudasama 19:11

Um I think you touched upon this a little bit. Um, all of us have our inflection points in life. Maybe if you could walk us through those moments for you, like you know what they were and what did you discover about yourself during that transition?

Madhu Chamarty 19:27

Yeah, absolutely. Um I like this question because I I always try to I don't know, I I always try to sort of present the the not so pretty side in the hopes that this makes people more comfortable with with life. So one example is uh this I'll give you maybe two examples, one work-related and one sort of college and school. Um uh first one is when I got into grad school, um, ended up at Stanford. Up until that point, I was always the, you know, in the top two or three smart kids in class, right? I didn't take that for granted, but that was just what it was. I just didn't find that there was a lot of challenge and I enjoyed it. You know, sometimes I'd be rank two, rank three, sometimes rank one. But nothing like getting punched in the face within a few weeks of coming to a school like Stanford. I, for the first time, realized there is nothing I could do to dig deeper and deeper into my abilities and my intellect. There are people that are way smarter than you. They just get it. And you have to work really hard just to pass. And that is a reality. That's not a reflection on you. That's just you just entered this avenue and this arena. And the name of the game here is survival and go. And so uh that completely reframed uh what I thought I knew about myself. It's like going from a shallow end of the pool to the deep end of the pool, and that's when I realized um sort of working hard uh is probably a better skill set to wish for than just being extremely gifted in life. And so I uh stopped underestimating sort of uh working hard and diligently listening and taking all the notes in class, and because that's the only way you're even gonna stay afloat. Um, and now people say, you know, if you had the choice of picking hard work or intelligence, you pick hard work. I didn't understand that up until then, but that hit me like a ton of bricks. Like the value, and there's always going to be somebody doing something better than you. But are you able to truly invest in the best of your abilities and diligently, methodically pursuing a discipline? Um, and you can surprise yourself uh and survive. More than you can. So that's that's one thing that I continue to think like the it's not the coursework, it's not any of the stuff at Stanford for me. It was the fact that for the first time, I was not at the top. And there's nothing I could do that's gonna bring me to the top. It's just a quantum leap from where I was. And there are kids from all over the world. It was just not just the US, right? So that's one one interesting infection point for me. And I I became a lot more humble, a lot more student of the craft, rather than just walking in and assuming things will just work out, as which I did uh uh up until then.

Hitesh Chudasama 22:35

Okay.

Learning Customer Success And Patience

Madhu Chamarty 22:36

And on the work front, gosh, like many inflection points uh that continued to do it. I think the first work infection point was when I joined uh my first startup Adify. Um I had joined it in 2007. And uh up until then, I was my first job was uh uh uh at a management consulting firm that put me at Microsoft. And so we were paid to think and give really interesting frameworks to execute, to be executed by the receiving team, right? Oh, there's a project that needs to be thought about. So give me a beautiful 10-slide deck and somebody's gonna go implement it. And I enjoyed it. I thought I was getting rewarded for something that uh came out of my brain and something on the whiteboard. But Adify's job to me was you're going to be kind of a part sales engineer, part account manager. And my boss at the time was a brilliant guy. He's he knew this propensity of me, of mine, to want to only think cool things and not actually implement it. So he said, Madue, you are qualified for this job, but I'm gonna call out one thing for you. This job involves long, quote unquote, boring periods of relationship building, and you truly have to nurture this over time. And that sounded awful to me, but I desperately wanted the job because I need to stay in the country and I have to take this job because I'm too tired of looking around and I kind of don't want to take it. It was a good salary. So he said, wait a minute. And then my thought was wait, I have to do the very thing I feel I hate, which is patiently helping somebody grow over time versus drawing some beautiful formula and walking away. And I said, Mm-hmm, yeah, sure. Yeah, I'll I'll totally do this. I understand it. And I reg, I kicked myself for saying, You fool, why would you do this? This is not what you want to do. But that is the first example of one of the best decisions of my life, of teaching me, just like Stanford taught me the value of kind of not being the smartest person in the room. Atify taught me the value of patient, kind of get your hands dirty, uh, relationship building with customers through thick and thin. And I kept that methodical, diligent pursuit of like things are just gonna take some time and you're not gonna see progress. And one fine morning you're like, holy cow, how did we do all these amazing things? Um, I was not that guy at the time. And so then I became a customer success manager, then I ran customer success, then I built a company, and then the size of deals went up. All of it was like the airline pilot mindset that was so not me. Be calm and to steady and grow this deal over time. So uh that's another example of like what I thought I was was completely not the job that was asked of me. And I thought I was a fool for taking it, but I that that has come to define me as a as a professional now. It still shocks me. Like in my head, I'm like this crazy 12-year-old on caffeine. But my persona in the workplace is oh, diligent, methodical, kind of, you know, funny guy, but you know, give him patient long-term tasks. And I chuckle to myself still, wow, who this is still an interesting skill set that you developed, and it's been beaten into me over 20 years, sometimes to my uh to my uh uh uh discontent. Anyway, uh I hope I answered your question, Nitesh, but uh those are definitely inflection points for me to realize that I could grow into such a role.

Han Yuan 26:23

Maybe you can elaborate a little bit uh on something for me, um, going back to hard work. And I think you touch on this a little bit with respect to you know your last story, which is one could argue you could work very hard on the wrong things and eventually effectively go nowhere.

Madhu Chamarty 26:42

Yeah.

Han Yuan 26:42

And so I'm wondering how how you think about decisions in general, whether or not you make decisions based on gut or or logic.

Madhu Chamarty 26:52

Yeah.

Decisions, Failure Rates, And Checkpoints

Han Yuan 26:53

Because the decision itself may dictate whether or not you have the outcomes that you want in life. Um hopefully fueled by working hard, but you could you know work hard and then just go on a road to nowhere.

Madhu Chamarty 27:06

Yeah. Yeah. Excellent point, actually. So uh there's a famous Michael Jordan quote, right? Of he's being celebrated for success, but he the quote lists all the times he failed. Failed to be picked for the high school basketball team, failed to make playoffs, failed to win trophies. Uh I have my own minuscule version of that. Like, much like everybody, and I and I hope folks can relate to this, like uh my professional life is littered with failures of investment in directions that I shouldn't have. And so after seeing that for many, many years, I came up with two observations that really help me think about how to optimize for decisions in the wrong direction. One is you're I I feel like when I like something, my personality is I'm gonna go 10,000 miles in that direction. One of the things I feel I have, I have discovered is I can go really, really far, really, really fast before I put my head up and realize, wait, how did I run to to this this town next town over? I just was gonna go for a jog. Um, so that's not gonna go away for me. And I kind of celebrate that personality of my, that trait of myself, right? I like it and you have to wield it carefully, but I like that I have it, I'm grateful for it. As a result of that, I will always be pursuing new things. I will always be chasing interesting things. Um if I can just reduce my failure rate, then I'm making progress every every few years. The number of pursuits I invested in should be that completely failed, and I could have seen signals or I could have cut my losses. Can I reduce those number of pursuits compared to last year versus this year? And this is a relatively new codification of my thinking, right? Five years ago, this is not how I was thinking. Now I feel like keep tracking every year or so. And if you can describe the number of things you failed at and you did it faster than you did last year, and you have a better way of teaching yourself the lesson than you did last year, man, good good work. Good, you're making progress because you're definitely not gonna not fail. And if I took uh there's there's a startup that I worked on, it was a mobile gaming company that uh basically asked you to solve a bunch of puzzles to reveal a photo. Uh, this was in the 2017 timeframe. And I like maniacally worked on it without any idea about how to monetize it or how to build a company out of it, just because I thought the technology idea was cool. I spent a year and a half on it before realizing I spent a ton of my own money and time not thinking about how to truly grow this into a company. And that somebody was willing to give me a half million dollars uh seed, but I had to shut it down to come back uh to California from Canada, mainly because my girlfriend at the time, now wife, said, enough of you living far away, come back. Um, but that was a complete looking back, I was like, man, I was clueless working on it. It felt great at the time. I was interesting things, but it was completely a bad portfolio allocation example. And I thought, you were whatever, I was in my mid-30s, and I should have known better, but I didn't. So many such examples, and now I feel like don't blame yourself for pursuing things that don't bear fruit. Try to build checkpoints where you can exit faster than you did before. And as long as you can show progress, if it's not a year, every two years, every three years, some notion of I am reducing my exposure to risk is probably the better thing to optimize. Um, and some people might find spend their entire lifetime thinking about it, right? But I think people don't think about uh reduction of exposure to risk. They just feel like they should judge themselves harshly for failing and therefore never try again. No, no, no, no, no. Just just fail less or hurt yourself less. That's okay. That's a that's a better way to think about it. Uh anyway, that's my framework, and uh, I'm I'm willing to pursue that forever, as long as I can show myself I'm making progress.

Han Yuan 31:40

It's it's fascinating because what I'm hearing from you is to reduce risk, that's not to decrease your turn rate. Actually, you need to increase your turn rate. So increase your turn rate, but in exchange, think very deeply about decreasing your failure rate.

Perseverance, Inertia, And Founder Reality

Madhu Chamarty 31:58

100%. That's exactly right. Right. I mean, this is also you could you could pursue as many scientific frameworks as needed to uh formalize this. But the the crux of it is this allows you to be a lot more forgiving toward yourself. And that is, I get an F minus in that skill set. And I struggle with it despite therapy, despite all of these things. It's just this deep sense of judgment that we all live with, particularly today, where uh stories of success and stories of speed are given all the mind share in the world, um, the room for not doing things uh the right way is is so so compressed. And so can you be more forgiving? And I and I think it's actually got a the way I look at it is this isn't just a uh kind of a go soft and be kind for the sake of it kind of thing, right? I actually think there's actually a sort of a selfish motive here. You really want to live the best version of your life, then allow yourself the room to truly blossom, and you're not going to blossom if you curse yourself, if you you know hurt yourself with judgment. So the best way is to say to the to the inner critic, hey man, that's fine. Yeah, yeah, it's okay. We're gonna we're gonna have a cheerleader counterpart to the critic in your own brain. That's how you optimize that big goal that you're going for, that promotion you're going for. So this isn't just go easy, honey. This is, dude, you really want to go to do great things, you've got to be more forgiving. Because you gotta go back to you need more ad bats. If you don't get more ad-bats, then what are you doing? The goal is not to go cry in the locker room, the goal is to get back. So, what can you do to get back? Is give yourself uh some grace, as uh somebody I know says. It's not easy, but uh it's a secret, maybe it's a sort of a secret uh tactic, I feel, that is not pitched enough.

Hitesh Chudasama 34:11

Yeah. No, this is great, Malu. So it's based on some of the things that you talked about. I mean, you talked about hard work, you talked about curiosity for you to be able to pursue all the different things, but I think um, as you mentioned, having empathy for yourself, making sure of the fact that as you're going through failure, being able to go ahead and be able to reflect on it, but being able to move forward quickly as well. So, which is great. It kind of leads me to the next question. It's you've had four successful exits, and I know you've gone through the different kind of journey in regards to building uh companies. What what what is some of the hardest part of being a founder that no one kind of talks about?

Runway, Macro Theses, And Pivots

Madhu Chamarty 34:51

Uh wow. There's a lot of things that are hard about being a founder. I I will start with something that that is the is the first kind of counterintuitive way to describe what's hard about being a founder that I experienced. And then I'll I'll kind of touch on maybe one or two other things. This was um Dave McClure, who launched 500 startups. Uh, this was uh uh he was talking about it, he was talking about 500 startups. They they had an event at uh somewhere at at Stanford, one of the weekend events for startup aficionados, uh maybe 15 years ago. And he has this very famous deck uh that he calls Metrics for Pirates. And these are like metrics that uh you have to show. And he mostly focused on consumer startups at the time. And one of the companies he had with him was uh Evernote, uh Phil Libben, who founded Evernote. This was just early on in Evernote's life, like maybe a year, year and a half or so. So Phil was one of the guest speakers, and Phil was certainly not a you know well-known name at the time because Evernote was very young at the time. And he presented, uh, they presented a set of slides that made you realize I'm here to scare you out of being a founder. I'm a venture fund, I'm an incubator, I want you to, of course, I want more startups, but here's 10 reasons why you should not be a founder. Something to the effect of you're stupid if you want to be a founder. This is an unglamorous life, and it's going to be very difficult, blah, blah, blah. And then if you're still standing at the end of the 10 slides, let's talk. But I'm here to convince you not to do this. Right. And I thought, what a wonderful sort of quirky way to present it. And so much of that, as we all know, is true now, uh, being a founder. I think so. Then let me get to my philosophy. So that was my first exposure to, man, like I this is an interesting way. Um any founder trying to build something, forget in tech, you are trying to bring some idea to life. It's a bookshop bookshop or it's a lemonade stand, it's a some digital product. You are fundamentally choosing to fight inertia. You're saying, I'm gonna come up with something, and I want you to take time out of your busy day and pay attention to me for 10 seconds or 30 seconds. The entire planet's inertia is working against you. It's just physics. That's just how it is. You want me to take left when everybody has been used to taking right? Well, I'm gonna I uh involuntarily am gonna come at you with the force of the universe to dissuade you from doing this. Of course, why wouldn't I? Inertia is in this way, and you're saying I should look this way. So one of the one of the the most uh powerful traits that that is valuable to develop is just the perseverance to stay the course. Uh the course of not just your idea, but just the course of I want to will something into existence. And that is underestimated, right? There are so many startups that have kind of quietly lived on a plateau for years, um, growing steadily, but whatever, not up into the right. And then bam, some inflection happens in their product or their market or something, and they take off. And if you look at companies like that and their journey, so I'm not talking about companies that have the benefit of market timing, right? I'm talking about companies that are most startups that are kind of they grow, but then they kind of plateau and they have to find another inflection point, inflection point, and then eventually they're successful. The the 10-year overnight success companies, not the cursors of the world. Um, if you look at the ones that succeeded, there's so many stories where the founder says it is pure happenstance or luck that we ended up pushing through. We got a consulting contract on the side, or we did this and we just wanted to push. So, can you stay in the game for long enough for you to see some kind of an event where you become the inertia? You're not fighting inertia anymore. So that's what I learned. I learned that markets change faster than you think, and they're only going to get faster in the course of human history because of technology as an accelerant. Um, uh, people's choices are fickle and are subject to change. Technology stacks are subject to erosion. What is one macro theory that your company is pursuing? Do you have one? Do you feel like most people are going to be on their mobile phones level of theory that can guide your work? Not the I want to open up a, I want to create a new iPhone app. So if you can ask yourself that the reason I want to pursue being a founder is because I have this notion uh that I think is going to be true for years to come. And I want to draw strength for perseverance from that macro belief, then you're already doing better because you're going to withstand lack of funding. You're going to withstand uh your teammates leaving, you're going to withstand customers changing preferences because you're chasing this idea. Dennis Crowley was one of the founders of Foursquare. And he said Foursquare was an idea in his mind for 10 years before he founded the company, which is mind-blowing, right? Uh, and I'm sure there's many other ideas out there like that. But um, so perseverance, I think, is understated and get the market right, you know, of course, don't underestimate luck, all that aside. If I were to pick one thing, it's the can you stick to it in some form or another, because you have a macro thesis enough, uh strong enough to guide your path forward. That's what I'd learned from time and time again. All the startups I've been part of is if you're clever with managing your staying power, good things will happen.

Han Yuan 41:22

But I suspect therein lies the the asterisk, right? Because you're what I'm hearing from you is that perseverance is key. But perseverance doesn't come for free. No. So for example, if I have an idea and it's burning cash, then you can't pursue it indefinitely. And so I do you have a sense of what's a reasonable metric before you need to be EBITDA positive or at least have enough gas in the tank to be able to keep raising money? Because that's that's ultimately what's going to drive your runway, right?

Long Arcs In An AI-Driven World

Human Maximalism And Time Affluence

Madhu Chamarty 41:59

Yeah, 100%. Yeah, so I wish I had uh a clear answer on because then I would pursue that all the time and never have to struggle with perseverance. But but what I did learn though, I will say, is um uh myself included, like specifically for myself, the way I think about starting companies now is very different than the way I think about starting companies 10 years ago for for many reasons, but specifically for the following reason. Um I never used to think about what is your macro thesis. I never had one for my entrepreneurial pursuits like 10, 15 years ago. An idea sounds good now. Let's go raise money now and try to sell it now. And arguably a lot of people are probably thinking about it that way because we are we overestimate the short term as a species and underestimate the long term. So most founders probably are building for something today. That already, in my mind, uh is is a potential handicap for you. Because it now, when I think about companies, I think about what is the macro trend. I'll give you an example of a macro trend. I believe this is part of my work at Laroden and my advisory work at HKMC. I believe that uh every company's workforce is going to be a combination of people and machines and AI. Whether I build Laridan, whether I build some other company, that reality is here to stay. So one of my drivers for entrepreneurial pursuits is are you pursuing that that kind of macro thesis? So that's step one of my advantage, right? I'm gonna, if for whatever reason the company I'm working on now looks like it's bleeding cash or something, the the the North Star of last resort for me is what can I do to pivot in the direction of this thesis? Is there anything Else I could do that can help the human robot thesis. That's the kind of thinking I tried to think about. And if the answer is no and immediately it's not working, then I go go after my loss prevention framework, which is oh, it looks like I'm not able to hook to my North Star. It looks like it's bleeding cash. Um, I do believe that people can start new things all the time faster than ever before. Cut it, cut it faster because you're trying to find your next at bat. Cut it now. And it's it's it's it's the most non-natural or non-intuitive feeling, right? Cutting something is not intuitive, always being on the lookout, always being paranoid about needing to pivot is an unnatural feeling. Because humans love to fall into zones and keep moving forward. You get comfortable with the status quo. And uh, who said I think uh Lou Gershner, one of the IBM CEOs, uh he was like, I'm constantly paranoid, and that's also something that's very difficult. So perseverance on one side, but paranoia on the other side, right? And these are not good friends at all. Um, so that's the the combo that I feel is is you kind of know that you have something that you're pursuing, and and I would really encourage anybody thinking about starting a company to not think about it in terms of product um or market, think about it in terms of like directionally what are you getting at? Because you're gonna have to have some anchor that's gonna keep you locked into this idea moving forward. There's plenty of reasons to start a company. You can start a company because you can quickly sell it in the next year and make uh uh you know a couple bucks. You can start a company because you know it it it like uh is exciting and you just get to spend some money for a few years and put founder on your resume, or you start a company because there's some uh macro thesis that is is is kind of hooking on your attention. Uh, I recommend people think about that because we are accelerating toward shorter attention spans, and we as humans are not sort of optimized for it. So if you can try to think about slightly longer time frames and then how to build a vehicle that can adapt constantly toward that longer time frame, you have more staying power in my mind, whether it's through the current incarnation or not. Um uh so yeah, that that that's uh I'll give you another example. The guy who one of my lecturers at Stanford, his name was Mark Leslie. He was the I think the first kind of professional CEO for Verasign back when Verasign was a company uh 20 20 plus years ago, 25 years ago. He said there's three reasons I think people start companies. You start a company because you want to make a lot of money, you start a company because you want to build a great company and culture, and you want to work in a place where you like people you work with, or you build a company to change the world, right? And he said, I joined VeraSign because I just wanted to build a great company. He didn't want to care about he at the time it wasn't changing the world thing, it wasn't making a lot of money, he just wanted to be, you know, build a great company. So that version of some version of that stayed in my mind for me. The career stage I'm in now, I tend to want to pursue directionally uh uh uh uh relevant ideas and story arcs. Pursue the story arc, don't pursue the market or the the idea because all of that's subject to change. And I think that with AI proliferation, everything is gonna erode faster than you think. So, what are the things that have longer staying power? And try to hook yourself to something that catches your interest that has a longer arc than you know, today it's Gemini 2.5 and tomorrow it's Gemini 3.

Hitesh Chudasama 48:07

As I know you're passionate about a lot of different things, um, and I know you're you write about different topics as well. Like, what are you excited about, both professionally and personally, that people might not expect?

Ikigai For Career Focus

Madhu Chamarty 48:20

I think maybe people might not expect if you looked at my my work or my writing or my conversations with folks, it appears that I'm uh I'm an AI maximalist, right? If you just look at the last six months or so, it's like AI this and AI that and AI is changing everything. But maybe what I am more excited about than AI itself is the uh the time and the um um value from all of this that humans are going to gain in the years to come. Where I I fundamentally believe that code continues to get commoditized. So human taste and curation and the things that are kind of undeniably human, um, um, physical presence and small communities and offline activities, these are all things that I think we will rediscover a taste for as a result of having AI help us with a whole lot of stuff that we spent otherwise a lot of our time on. So I'm a human maximalist, and I really look forward to building technology or perspectives that give us our time back for things that matter a lot to us. Um, that's not going to be without uh some societal displacements that we're starting to see now, right? Whether it's employment or what have you, but um, but I I remain long-term optimistic that we we can gain time back uh to do things we want to do as human beings, and so that's something that I'm constantly thinking about in everything I do um professionally, and then um personally I think my timelines for everything in life have just gotten longer, and I like that the expectation, the ROI timelines have become delightfully longer, deliberately longer. So I think that oh, I'm gonna build this thing and it's gonna come to fruition at some point, and it's such a relieving, forgiving feeling not to expect everything to happen yesterday or today or tomorrow, and maybe it's age or maybe it's I don't know what it is actually, but uh I appreciate the appetite for longer time frames uh to really do some of your best work. Um, so philosophically, I'm applying that. I'm reinvesting in relationships, uh personal relationships, I'm reinvesting in patiently staying a part of my family's lives. And uh there have been years when parts of my family forgot that I exist because I'm in this black hole and working on some things, and so um I'm investing in slow things now.

Hitesh Chudasama 51:08

So I know that um as we talked about, you've had a lean a non-linear path throughout your career, and you've you know tried out different things. If there's an audience member who's listening to this right now, what is something that you would advise them as they're going through the through this particular phase in their life where they're trying to figure out you know what to go ahead and focus on?

Where To Follow Madhu And Closing

Madhu Chamarty 51:31

Yeah. Uh there's many ways I could answer that, but I'll I'll take the slightly lazy way uh and propose uh the framework, um, the Japanese framework of Ikigai. Uh, right? Uh I forget the four prongs. I think things that you're good at, things that you can get paid for, things that the world uh uh needs, and the things that you like working on. That's actually a to me that has proven to be a very surprisingly useful, actionable framework. And I feel most people are pushed to over-index on just one of them. And it's usually, oh, you are good at this, so you should pursue this, or the world needs this, so regardless of what you feel about it, you need to go do this. Everybody's gonna go become a software engineer, so who cares if you like if you like humanities, go learn how to code, right? But there's a lot less emphasis on what is the combo of those four prongs that resonates with you, and invest some time in figuring out what is that for you, yeah, and try to be as close to it as possible as early as possible. Whether it doesn't matter uh if you're your age, what I mean by early is if you listen to this now, I implore you to consider that uh perspective, consider applying Ikigai thinking to your life right now, not tomorrow, not like next year, but just the pursuit of knowing the intersection of what you like, what you get paid for, what the world needs, and what you enjoy doing is going to hopefully change what you do on a day-to-day basis, and it just fills you with more um uh satisfaction. And I fundamentally don't believe that um, hey, like everybody's gotta pay bills at the end of the day, right? So you gotta go get a job. I understand that, and of course that makes sense, but there's not enough emphasis on as a society investing in oneself and understanding what is that intersection for each person because we're too scared and we push ourselves in one direction versus the other. So if I were to give one piece of advice, it's invest in the the the right intersection of skills and passion and and what the world needs. In fact, more people need to think about what the world needs, also. Um that's my my attempt at advice to folks.

Hitesh Chudasama 54:14

Um other than this has been really great. Um for audience members who want to follow your thinking, where should they find you?

Madhu Chamarty 54:22

Oh, thank you. Uh so I write uh Substack, I started writing, so it's ands not oars.substack.com. It's A N D S not O-R-S, all one word. I believe that life is and's not ours, so live a full life. Ands not ours or substack. I'm also on Twitter, Mr. Medici. Um uh I thought the Medici family did some very cool things, and so I picked that years ago. It's M-I-S-T-E-R-M-E-D-I-C-I. Um, I'm also on LinkedIn and probably a few other platforms that I don't use, but yeah, I welcome any perspectives and happy to connect with folks.

Hitesh Chudasama 54:59

Wonderful. Thanks once again, Madhu.

Madhu Chamarty 55:02

Thank you very much, attention, Han. Thank you, and uh, I'm excited to see when this comes out.

Han Yuan 55:08

Thank you for thank you for all this. I think it was um just so absolutely fascinating. I think one of the takeaways that I I received from you is this concept of time affluence, um, and how important time affluence generally is, and to be able to suspend that time in a way that's meaningful to each of us. I I think that's uh that's a very powerful message. So thank you for that.

Madhu Chamarty 55:35

Oh, thank you very much for phrasing it so wonderfully. I appreciate that. I welcome um uh the the the codification that way, and uh what a privilege to talk to both of you. So thank you so much.

Han Yuan 55:46

Thank you.