Valentine's Day Special: Building Human Connections, one pair at a time; S. Anil Kumar, Jodi365

1. 0:00 – 1:16

   Intro

   1. SKS. Anil Kumar0:00

      Can I curse? People are caught up with their own shit. When you're twenty-nine and stressing about, "Oh, I'm going to be thirty, I might be seen as an old maid," I would rather that you are thirty-one and still discerning and single, rather than get hastily hitched at thirty. And in one quadrant you have the Tinders, and then a Bumble trying to be an alternative to the Tinder. Interestingly, Sundar Pichai and I took, um, physics lessons in the same classroom.

   2. AMAmrut0:23

      Is it? The way you are describing your own journey feels a lot more human-

   3. SKS. Anil Kumar0:30

      Yeah

   4. AMAmrut0:30

      ... and it feels like this is a story that's happening all around us.

   5. SKS. Anil Kumar0:34

      In, uh, a pitch deck, I don't need a pitch deck anymore because I can tell someone, tell VCs, and say, "Screw you."

   6. AMAmrut0:40

      Hi, this is Amrut. We are at IIT Madras, my alma mater, and India's top university for people who like to build. We are here to meet some builders, ask them: What are you building? What does it take to build? And what makes IIT Madras the best place to build? [upbeat music] Hello, and welcome to The Best Place to Build Podcast.

2. 1:16 – 1:51

   Intro

   1. AMAmrut1:16

      Today, we are sitting with Anil. Anil Kumar is a very different kind of founder. He runs a service called Jodi365. It's a personalized matchmaking service, and he's been running it for fifteen plus years. He was a student here from nineteen ninety to nineteen ninety-four. Uh, yeah, welcome to the podcast, Anil.

   2. SKS. Anil Kumar1:33

      Thanks, Amrutash. Yeah, pleasure to be here-

   3. AMAmrut1:35

      Uh-

   4. SKS. Anil Kumar1:35

      ... especially here at IITM.

   5. AMAmrut1:37

      Yes. Um, by the way, today is reunion day, so a lot of alumni are there.

   6. SKS. Anil Kumar1:41

      I know this. I know this. Class of two thousand, there are at least a couple of people in my network from there. I meant to check with them, but I might just still do that.

3. 1:51 – 7:52

   How does Anil Kumar describe what Jodi365 is?

   1. AMAmrut1:51

      Okay. So Anil, um, tell us about your startup, and what is... Uh, do you call it a startup still?

   2. SKS. Anil Kumar1:56

      No, not after all of these years. Uh, I founded this in two thousand and nine in Chicago, in the home stretch of my MBA program at the University of Chicago, the Booth School of Business. And, uh, it's for many years now that I've been describing myself as not an entrepreneur, but as a businessman. I say that I run a growing business. Still a small business, a small, growing business. Jodi365 is a matchmaking platform and service. It began as a platform, with personalized service being an option. We pivoted into a fully personalized service, so we spare people the searching, the screening, and the curating. We do the heavy lifting, and we present these pre-screened, curated matches to people on a regular basis. We help people find their life partner at a pace that's right for them. Some people may be ready for marriage in the near term. Some people may be comfortable with the idea of, um, getting married, but not rushing into some- ru- rushing into the formal process. They may prefer to get to know somebody over time. They may be okay with an engagement. Some others may say, "Back off, no pressure. I'd like to get to know someone as friends first." So wherever they are on their readiness, on the readiness spectrum, we help them find the right partner.

   3. AMAmrut3:12

      Nice. Um, I got married many, many years ago, so [chuckles] I have no idea what the problems or the anxieties of younger people are. I can see that people are quite worried in general about finding a partner, but can you describe the problem to us? Like, how is the... What are you solving for?

   4. SKS. Anil Kumar3:29

      Yeah. So I'd say that it's not, uh, a search problem. Uh, there are enough singles out there. It's more of, um, figuring out who's right for you, and it's hard when people are well-educated, accomplished, they have some aspirations, and they may not have the bandwidth to put themselves out there, and it takes putting oneself out there. Uh, and if you are to put yourself out there, you're not sure of multiple things. What, are you to go scanning people's fingers to see whether there's a ring on it? Someone may not have a ring and still be taken. Someone may not have a ring and, uh, just not be open to the idea. So how is one to go about figuring out, um, who may be a potential partner? And before that, I'll even rewind one step. I've had the good fortune of running a business that I've not had to evangelize, as in, "Oh, please think about edtech. We are offering education solutions online." For as long as humans have existed, humans have sought to get into relationships. We are wired to pass the genes on to the next species, uh, to the next generation. We are wired for companionship, so I've not had to sell the case that this is a problem worth solving. It's just a question of how effectively you solve the problem. Online options are convenient. They are like watering holes where you know that singles congregate, but not necessarily only singles congregate. So when you get into these watering holes, you're not sure who's genuine, who is fake. Even if somebody is genuine, how serious they are. Even if they are serious, what their intent is. Is it for the long term? Is it for short term that may evolve into the long term, or is it because they are bored or horny on a weekend? How do you figure this out? So in a way, we are like a concierge. We are many things, but one of the things is we are a concierge. You can order your meals, and it comes to your door. You can order your groceries and even get things couriered to you within the same city, across neighborhoods. In a way, we bring present- we bring pre-screened matches to somebody who may be busy. We tell them: "Live your life, best life better. Let us do the heavy lifting, and spare you the effort of even figuring out all those unknowns. Are they genuine? Are they real? Are they serious? Do they have intent? Do they have interest?" People underestimate the value of having someone to be a trusted intermediary, to ask the hard questions that you may be too polite to ask. Okay, so-... he seems to be sorted, but yeah, he's an entrepreneur. How is he doing financially? You'd want-- a woman would want to know if a guy is sorted. Even if it's, uh, a young man, he'd want to know how is she doing professionally, or what's her personal background like? How many skeletons in her closet? She may wonder, what's his life story like? Personal questions that we wouldn't even feel comfortable asking, but somebody who does this professionally can take it as their responsibility to ask the difficult questions, spare you the awkwardness of asking the difficult questions, uncomfortable questions, spare you the misery of fielding sensitive questions or outright insensitive questions. Beyond bringing matches to you, getting this additional information, facilitating the exchange of sensitive information. Beyond that, making personal introductions. Beyond that, remaining in the background to make sure that there's no communication snafu, there's no communication mix-up, there's no communication breakdown, so that people are talking and getting to know each other. And if there isn't that much enthusiasm on one side or both sides, being able to call it and say, "Look, you're better off focusing on the one who may be right for you. You go on and focus on someone who may be right for you."

   5. AMAmrut7:19

      Right.

   6. SKS. Anil Kumar7:20

      We are... And with all the gray hair, for me to be able to come in and play the role of a guide, a counselor, help people navigate the emotional rollercoaster. So I say the best word is matchmaker.

   7. AMAmrut7:32

      Mm.

   8. SKS. Anil Kumar7:33

      It's what I do, connecting people.

   9. AMAmrut7:35

      Very interesting. We have this, uh, notion of a meet cute kind of story from movies where everything just-

   10. SKS. Anil Kumar7:43

       Yeah

   11. AMAmrut7:43

       ... happens in a flash.

   12. SKS. Anil Kumar7:44

       Yeah.

   13. AMAmrut7:44

       But you're saying that it's a long process, and-

   14. SKS. Anil Kumar7:47

       Yeah, yeah

   15. AMAmrut7:48

       ... um, it would really help to have somebody on your side.

   16. SKS. Anil Kumar7:50

       Yeah, yeah. And see,

4. 7:52 – 22:53

   Why is matchmaking a problem to be solved?

   1. SKS. Anil Kumar7:52

      generations ago, you had the tribe doing this. You had not just the immediate family. In our culture, people are incentivized to help the next generation find somebody who may be right for them. Uh, and today's twenties and thirties, uh, twenty, thirty... The twenties, thirties generation is not averse to the idea of um, an arranged marriage or a semi-arranged marriage-

   2. AMAmrut8:16

      Mm

   3. SKS. Anil Kumar8:16

      ... but they like to have the sense of agency, understandably. Earlier, you had not just the nuclear family, but even the extended family who would think that, "Oh, okay, "... to use a Hindi expression. Woman's, young woman's coming of age, young man's also settling down professionally. Shall he start getting the word out? So they get dragged to these weddings and all dolled up, and-

   4. AMAmrut8:39

      Yeah

   5. SKS. Anil Kumar8:39

      ... announcements are made subtly: "Hey-

   6. AMAmrut8:41

      Yeah

   7. SKS. Anil Kumar8:42

      ... he's grown up. He's doing well. She's doing well." Yeah, we-

   8. AMAmrut8:46

      All the Navratris and the Diwali festivals.

   9. SKS. Anil Kumar8:49

      Yeah.

   10. AMAmrut8:50

       Yeah.

   11. SKS. Anil Kumar8:50

       So much value for these kinds of functions. I attended a client's, uh, eightieth birthday celebration in the family just last night. These are great occasions to bring the folks out and to let the word get out in subtle manners. These days, everybody's caught up with their own... Can I curse? People are caught up with their own shit.

   12. AMAmrut9:10

       [chuckles]

   13. SKS. Anil Kumar9:11

       And they're also wary that, look, if we make some introductions and it goes south, we don't want all the grief, uh-

   14. AMAmrut9:18

       To come to me

   15. SKS. Anil Kumar9:19

       ... to come to us. Yeah, "So we wish you well. Good luck." "Yeah, we'll think about it. We'll let you know if there's somebody." And even families, they are a little concerned, as in, "Look, I'm not sure. I don't get it these days. I don't know what you Gen Z, what you millennials want. Sure, if you find somebody, let us know. We'd, uh, if they pass our sniff test, we'd be all supportive." I'd like to put it this way, that people say that there's, uh, an India shining, but there's also an India drowning. There's a case of two Indias. I say, no, it's a case of who knows, hundreds and thousands of Indias. And people at, um, different socioeconomic strata, different sociocultural backgrounds, different, different levels of, uh... Whether they are conservative or liberal, there are so many pendulums swinging in this maddeningly fascinating society at different, uh, time lengths, different scales, bouncing about, clashing, and not quite connecting. Wheels of change keep progressing, so it's no surprise that there's been room for somebody like me to come in, to draw on all my lessons learned, all of my pain and suffering that motivated me to start a different kind of solution.

   16. AMAmrut10:31

       Very interesting. I want to ask you about the different kind of solution. Uh, Anit, you're saying that this is an old problem. Society anyway is incentivized to couple young people up. Um, maybe it's changed over the years on how the process of coupling happens and how people find each other and-

   17. SKS. Anil Kumar10:47

       Yeah

   18. AMAmrut10:47

       ... at least in the last fifteen, twenty years, technology has had a huge impact, right?

   19. SKS. Anil Kumar10:52

       Sure.

   20. AMAmrut10:52

       So it's-- is it a technology-driven solution? Uh, I mean, I, have I heard of AI-based matchmaking now? I don't know how that works.

   21. SKS. Anil Kumar11:02

       Yeah.

   22. AMAmrut11:02

       Like, would love to hear how that has moved in the last ten, fifteen years-

   23. SKS. Anil Kumar11:05

       Sure

   24. AMAmrut11:06

       ... with sort of technology falling in.

   25. SKS. Anil Kumar11:08

       Yeah.

   26. AMAmrut11:09

       And of course, like, uh, in our country, Shaadi.com and BharatMatrimony are the largest, right?

   27. SKS. Anil Kumar11:15

       Yeah.

   28. AMAmrut11:15

       There's, uh... And they are tech businesses, so.

   29. SKS. Anil Kumar11:17

       Sure, sure.

   30. AMAmrut11:18

       Um, and they're old now. Like what? Each of them is twenty years old, um-
5. 22:53 – 27:05

   His personal journey from IIT to the US

   1. AMAmrut22:53

      you tell me about your schooling, your, uh, your IIT days? Uh, it's, it's, uh... For me also, it's nice to hear how the ni- early '90s were.

   2. SKS. Anil Kumar23:02

      Yeah, yeah. Thanks for asking, and I, I say that, that we are our stories, and the older that I've gotten, the more appreciation that I've got for my story. I grew up in Chennai. Um, Chennai boy, out and out. Even though I was born in Hyderabad, my parents moved here from the time that I was a baby. And I'd like to share this because it's so much about, um, also what is Chennai? The perception of Chennai. It's a lot different than the Chennai, the Madras, in which I grew up. I grew up. I'm fifty-three, right? So you could say I'm a kid of the '80s, early '80s, when from the time that I have my earliest memories. I come from a multicultural home. My father passed away a couple of, few years ago, a South Indian Brahmin from Kerala. My mother, a Sindhi from pre-partition Karachi, and came over safely on a steamer from Karachi, uh, to Mumbai, and her family made Calcutta their home. And my parents met and fell in love at the workplace in the Calcutta of the '60s. My eldest brother was born there. Family then moved to Kanpur, Lucknow.... and then Hyderabad, where they lived for several years. My other brother and I were born there. And my father got another opportunity in Chennai, and I would feel for my poor mom, for whom English was a second language. She didn't know English before she was fifteen, sixteen in Mumbai. And, uh, Tamil, a third language at best, and to relocate to the Madras of the s- mid-'70s was tough for her. Different food, different, uh, language, different customs, but such a cosmopolitan city. I used to get grief from my cooler cousins in Kolkata, "Oh, you sleepy city, Madras."

   3. AMAmrut24:59

      [chuckles]

   4. SKS. Anil Kumar24:59

      "Look at Calcutta." And I think about-

   5. AMAmrut25:03

      Fixed it out now.

   6. SKS. Anil Kumar25:04

      No, but even otherwise... Oh, sad. I feel for Calcutta.

   7. AMAmrut25:06

      Yeah.

   8. SKS. Anil Kumar25:06

      What a glorious city that has just decayed over the last three, four decades. But I may be biased, and I'd still say that Chennai probably has the best quality of life for a big city in the country.

   9. AMAmrut25:21

      Mm.

   10. SKS. Anil Kumar25:21

       Hyderabad may come close. I don't know, Pune may have some backers, but there are so many things that are not so good about Delhi. I challenge my friends: Why would you want to live in a gas chamber?

   11. AMAmrut25:33

       Yeah, it's terrible.

   12. SKS. Anil Kumar25:34

       There's so much that, uh, Chennai has to offer. No surprise that it's ranked in, uh, New York Times' top fifty cities to see twice for the culture on, uh, maybe a Nat Geo list of top ten foodie cities in the country, in the world.

   13. AMAmrut25:52

       I know it's... People give Chennai a lot of flak, but my time in Chennai was lovely. I really loved it.

   14. SKS. Anil Kumar25:56

       Yeah.

   15. AMAmrut25:56

       I've now moved out. I spent twenty years here.

   16. SKS. Anil Kumar25:59

       Mm-hmm.

   17. AMAmrut26:00

       Yeah, great weather-

   18. SKS. Anil Kumar26:01

       It's like-

   19. AMAmrut26:01

       -great roads.

   20. SKS. Anil Kumar26:02

       Yeah. Yeah, yeah, education, uh, culture.

   21. AMAmrut26:05

       Yeah.

   22. SKS. Anil Kumar26:06

       Um, and-

   23. AMAmrut26:06

       And we are in the middle of Margazhi season, so.

   24. SKS. Anil Kumar26:08

       Yeah, yeah. I attended school here at one of the good schools in town, and growing up, uh, this was a time when if somebody was bright in s- at school, doing well at school, oh, either engineering or medicine, the two tracks with blinders. And if you were not bright, the third part, the good-for-nothings would study commerce. Yeah. What a pity, and there are so many smart, whip-smart folks who-

   25. AMAmrut26:37

       Yeah

   26. SKS. Anil Kumar26:38

       ... have a flair for numbers, and they go into accounting and pursue B.Com and beyond, CA and banking, and who knows whatever else opens up for them. I had, uh, this affinity for engineering, maybe the influence of a bright cousin who was a decade older, who studied at what is now one of the NITs. He attended what is in one of the RVCs, Regional College of Engineering, RECs,

6. 27:05 – 38:52

   How a personal pain point led to an entrepreneurial insight?

   1. SKS. Anil Kumar27:05

      and, uh, didn't know much about the IITs. I remember vaguely noticing these classified ads for one of the coaching factories. There was a brilliant tutorials in the, uh, late '80s, not knowing what the JEE was, these fancy acronyms. It was an eye-opener for me when I may have been in class eleven or twelve and was very much into the inter-school cultural competition scene, participating in quizzes, general quizzes, uh, general knowledge quizzes, science quizzes, even cultural competitions, um, damsharas. And there was an event at IIT Madras campus on the occasion of what is called the Day of five Billion. May have been a United Nations-promoted event when the population was about to hit five billion. Their way of raising awareness that, oh, probably too many people around.

   2. AMAmrut27:57

      Mm.

   3. SKS. Anil Kumar27:58

      I'm not a fan of these doomsday prophets. Uh, I remember, uh, in the mid-'80s, oh, oil is going to run out by '20 or 2005, and it seemed way out there, but I'm more of an optimist. Um, but I'm glad that there was this, that occasion that brought me to campus, and I remember a jeep being, feeling as if I was in Wonderland, and I thought that, "Wow, this, this is the IIT that they speak of, one of the IITs that they speak of." It became my dream to walk through the portals of this institution. And-

   4. AMAmrut28:34

      But that, that first-

   5. SKS. Anil Kumar28:36

      Yeah

   6. AMAmrut28:37

      ... visit to campus-

   7. SKS. Anil Kumar28:38

      Yeah

   8. AMAmrut28:39

      -because you walk through the trees, and you, or you take a bus or whatever.

   9. SKS. Anil Kumar28:42

      Yeah.

   10. AMAmrut28:43

       Go through the trees, and you see the wildlife.

   11. SKS. Anil Kumar28:44

       Yeah.

   12. AMAmrut28:44

       It's just hits you in a different way, right?

   13. SKS. Anil Kumar28:47

       Yeah, yeah. Neither of my parents attended college.

   14. AMAmrut28:50

       Mm.

   15. SKS. Anil Kumar28:50

       Imagine that. And here I've gone on to earn a bachelor's BTech from IIT Madras, and-

   16. AMAmrut28:56

       And then to Chicago Booth.

   17. SKS. Anil Kumar28:58

       Uh-huh, but that came much later. So I'll sort of compress my journey. I... And I posted just last night, I have an alphabet soup of credentials: BTech, MS, PhD, a Professional Engineer license in the US, and then an MBA.

   18. AMAmrut29:12

       Oh, you're a professional engineer, licensed engineer?

   19. SKS. Anil Kumar29:14

       Yeah, yeah, yeah.

   20. AMAmrut29:14

       Okay.

   21. SKS. Anil Kumar29:15

       So I had the Professional Engineer license, which meant that I had to demonstrate that I had competence in my discipline and was also practicing under the apprenticeship of, um, trained professionals. So, uh, my journey was, yes, setting sights on this, plodding my way through it, not wanting to go through the tutorial model or these pre-internet postal-

   22. AMAmrut29:39

       Yeah

   23. SKS. Anil Kumar29:40

       ... classes, where booklets would be sent by mail.

   24. AMAmrut29:42

       Yeah.

   25. SKS. Anil Kumar29:42

       You'd have to te- send in your answers.

   26. AMAmrut29:44

       Test papers.

   27. SKS. Anil Kumar29:45

       Test prep-

   28. AMAmrut29:45

       Yeah

   29. SKS. Anil Kumar29:45

       ... kind of service. I took lessons from, uh, college professors who offered math coaching, physics coaching, chemistry coaching. I didn't... Imagine, I thought that I could get by without chemistry tuition the first time, and I needed two attempts at JEE to get through.

   30. AMAmrut30:03

       You had two attempts?
7. 38:52 – 47:10

   What is broken in dating apps and how can technology fix it?

   1. SKS. Anil Kumar38:52

      different expression.

   2. AMAmrut38:53

      Fair enough.

   3. SKS. Anil Kumar38:53

      Yeah, be good. A-allow me to dwell on this. So you had, um, people taking the GATE to get into M.Tech at IIT. You had people taking the GMAT to pursue an MBA right out of undergrad. I saw advice against doing an MBA right out of college. An MBA is something that is enriched by experience, uh, work experience. Otherwise, it will be all theory, so go out, work for at least a few years. And then there were people who were applying for, um, grad school in the US in engineering and the sciences. That is what motivated me the most, because I thought about what's the best thing that I could do with my life, which is to make some contributions, advance humanity in some chosen field, in my field. By then, I'd taken an interest in hydrodynamics. So I thought, let me pursue that for a career. Let me write the... That's what I aspired to, write the next Bible in marine hydrodynamics. So, uh, worked hard to get into the best programs in my field. I say this with pride. Got admits into MIT, Berkeley, Michigan. Applied to ten programs, got admitted into all. But it was important for me to have my studies fully funded, not just tuition be waived, but also get an assistantship. Had just four, three and a half offers. Berkeley offered me a fellowship, but it wasn't going to cover all expenses. Uh, I was headed to the University of Maryland for a straight PhD, but got jitters, as in, here I'm committing to a path. You do a PhD, and that's your terminal degree that decides what beyond. I'm not even sure what's the expertise-

   4. AMAmrut40:37

      Wow!

   5. SKS. Anil Kumar40:37

      ... of this professor that I've been picked to train under. I felt more comfortable taking a two, two-step path to a PhD and beyond, getting a master's along the way.

   6. AMAmrut40:47

      Okay.

   7. SKS. Anil Kumar40:48

      So I got a master's from the University of Iowa, specializing in computational ship hydrodynamics.

   8. AMAmrut40:53

      Mm.

   9. SKS. Anil Kumar40:54

      Essentially coming up with computational models to simulate fluid flows, in this case, around ships, to predict waves generated by ships, so that you can help to minimize the signatures of ships, so that these signatures are not spotted by satellites. A lot of the funding in the US would be from the-

   10. AMAmrut41:13

       Navy

   11. SKS. Anil Kumar41:13

       ... Office of Naval Research.

   12. AMAmrut41:14

       Okay.

   13. SKS. Anil Kumar41:15

       Yeah, the equivalent. The Department of Navy had an Office of Naval Research, which would pump in as much as they need to. And just as you had stealth bombers, you also have stealth, um, uh, ships. Naval combatants minimize their signatures. And not just to minimize wave signatures, also to predict the powering requirements of ship. By how- ships are essentially wave makers. As you, as you press forward, you're generating these waves. So if you, um, have, um, better, sleeker hull forms, you have, uh, lower powering requirements. And traditionally, how would this be done? How would you come up with fairer, sleeker designs? You have, um, wind tunnels in which you test F1 cars. Look at F1, right? How many hundreds of millions of dollars are spent by racing teams to improve their technology every year? You have aircraft also that are tested in wind tunnels. The equivalent for, uh, ships are towing tanks. These tanks that are maybe a hundred meters long, in which you have these scaled wooden models, wax models, that would be towed, and you would measure the resistance required to, uh-... through the, through water. And then you think about, oh, let's chamfer it a little bit over here. Let's pare it a little bit over here to improve the design. How laborious! Computers are what? Glorified, uh, workhorses.

   14. AMAmrut42:41

       Mm.

   15. SKS. Anil Kumar42:41

       Uh, if you come up with a way... You think of the equations that model fluid flows, think of a way to discretize these equations that can be fed into a computer, come up with a model to solve those, uh, equations, you're essentially simulating the flow of these, these natural processes.

   16. AMAmrut43:01

       It's very interesting to hear you speak with such clarity and passion, even after so many years about your... I guess this was your master's thesis?

   17. SKS. Anil Kumar43:09

       And subsequently, my PhD also.

   18. AMAmrut43:11

       Okay.

   19. SKS. Anil Kumar43:11

       I went into marine consulting as a way to broaden my footprint, so it helped that I was set a full service naval architecture, and, uh, marine engineering, and, uh, transportation consulting firm. Uh, boutique firm, stayed consciously small. To their credit, they didn't want to grow through boom times and then mass layoffs. To this day, I've been so positively influenced by my, uh, early youth in the US, and coming across such kind folks, good-hearted folks in the Midwest, known for its, uh, good nature. As much as people know that, yeah, the US can be a cutthroat place where money talks, uh, even at the firm that I worked with, good people. But I, um, also think that, um, they put it well, I was too ambitious for my own good in many ways. I was restless, wanted to go beyond this. But I wasn't like the typical they see in the US who thinks that, "Hey, green card. When do I get a green card, and how do I go about this?" Yeah, I loved my life in Seattle, where I was putting my roots down, working at this consulting firm. They are still a consciously forty, fifty percent firm, even though they've been around for five decades then. Had, um, uh, my heart in the right place, had causes that I felt dearly about, so I took on volunteer and then leadership roles at an NGO. Served on its international board, so became active in the community. And I thought, "Oh, what better way to make an impact by building on that?" Maybe starting a business, building an organization, leaving a legacy. And then I paid the price for not having cared about permanent residency, even though my- I could have filed within week one of finishing my, uh, doctorate. And three years later, the wait for a green card was non-linear. But I bided my time, and while biding my time, I thought that as part of my own continued professional growth, may be good to get these broader skills in management and entrepreneurship. Today, I would tell folks, "If you want to be an entrepreneur, the best thing that you could do is to join a startup." Join a growing startup. Join a well-funded startup, probably after S- Series B-

   20. AMAmrut45:32

       Yeah

   21. SKS. Anil Kumar45:32

       ... where there is not, uh, there's still a lot of growth, and you're not another cog in the wheel, but you have a lot of responsibility that you can take on, a lot of visibility among investors also, for that- so that when you're ready to go and launch your own thing, you'd have some people who've seen what you can do, and you'd learn so much.

   22. AMAmrut45:52

       Yeah, um, starting up is the university of hard knocks.

   23. SKS. Anil Kumar45:56

       Yeah. Yeah.

   24. AMAmrut45:57

       Uh, you learn faster-

   25. SKS. Anil Kumar45:59

       Yeah

   26. AMAmrut45:59

       ... than anything else.

   27. SKS. Anil Kumar46:00

       Yeah, and ask me about all the-

   28. AMAmrut46:01

       Hard knocks

   29. SKS. Anil Kumar46:02

       ... things that I've learned the hard way, by my own mistakes. Fast forward, um, I decided while I was waiting for permanent resi- residency to come through and all the career mobility that would come through with that, I attended a weekend program, MBA... weekend MBA program at the Chicago Booth School of Business, and, uh, found it very enriching. Uh, very enriching. Uh, yeah, it was a highlight of my program to get to apprentice at what is now one of the leading angel investment networks in the US, Hyde Park, in the Midwest, at least. Hyde Park Angels, that was supported by the schools, founded by alumni of the program. And I got to be on the other side of the table, helping to screen startups that were applying for funding, helping to curate and present select startups on a quarterly basis, on a weekly basis, and culminating in a quarterly presentation before the angels in the network. And going beyond that, I was so into it, also getting to, uh, getting the opportunity to invest in a startup that I saw promise in,

8. 47:10 – 55:28

   Anil’s definition of compatibility

   1. SKS. Anil Kumar47:10

      getting to be on the deal team, and getting to work with a startup post-funding because it was a portfolio company. With all the goodwill that I learned, and I did outstanding work at HBA, I had doors being graciously opened into venture capital for me. Uh, a lot of goodwill bank.

   2. AMAmrut47:30

      This is what? 2008, 2007.

   3. SKS. Anil Kumar47:33

      Going into 2009. I had mentors who were graciously opening doors. I could well have joined a fund, but no, <i which I couldn't startup karna tha.</i I wanted to do a startup of my own. And the problem that most excited me, the opportunity that most, uh, excited me was related to the problem that I'd personally known for the previous decade. I was thirty-six then in early 2009, in the homestretch of my Booth MBA. By then, I'd got my green card, so I had the mobility to... It came in during the midway point of my program, conveniently between quarters in the second half of December. So I quit my job, locked the door, switched the lights off, packed what ultimately were thirteen suitcases, and I moved to within two blocks of campus and finished the second half of my program, effectively full time.... and, uh, I said before that it was very enriching to get that experiential learning opportunity while going for my Booth MBA. And yeah, being in my thirties, mid-thirties already, taking stock of how there was this problem that is unsolved for me. I was doing well professionally, but personally, I had not found my wife yet. Mm. I had been still single, even though I was not only open to the idea of finding a life partner from my mid-twenties, but was proactive about it. I wasn't one of those folks who would think, "Ah, outsource it to- delegate it to mom and dad." They'd find somebody, I'd fly to India and return with a bride. Mm. My parents chose each other for themselves, uh, a generation earlier, so we always had that agency that we'd find somebody on our own. And I thought that I did in my mid-twenties. Fell in love with a sweetheart from the American South, found her online. We found each other online. And I'm glad that there were online options already in the first wave of the web, Web 1.0, Web 1.2, as we refer to them these days. Uh, because the kind of person that I was looking for would be tough to find in the course of everyday life. Very discerning preferences. I'll not dwell on it. Don't mean to digress. But what do you do? No surprise that I had to deal with a breakup, allowed hair. I took my time licking my wounds and making peace with the breakup, and being comfortable with giving my heart again, risking giving my heart again, because it comes with the risk of heartbreak. I found somebody I thought at thirty, again, conveniently online. And this time I had more means that I could invest in coming up with a lovely ring and a surprise wedding proposal, and then going on to think of what kind of wedding. She was German Canadian, uh, another long-distance relationship for a while. Even ideating on baby names that would sit well with her culture and mine, and drafting a wedding guest list. But again, I came to know heartbreak. And I would do what the typical consumer would do, which is if you get tired of the food at this restaurant, "Oh, never again going there." Maybe trying another platform or thinking that, "Oh, I'm not eating outside. Maybe the best way is to cook your own meals at home." I'm talking of the analogy. Let me just find somebody organically. How? I was not into the bar, club, bar hopping or night clubbing routine, the partying lifestyle. Where's the time and bandwidth for that? So focused on my- Career ... professional growth. Yeah. So how at least make time to socialize with friends twice a month, or make time for activities that I would enjoy, whether it's hiking through the Sierra Club, or a running group, or a vegetarian potluck- Yeah ... or a reading group. So you find somebody with similar interests and worldviews. It's tough. And, uh, coming to realize that, yeah, it's a jungle out there, but then thinking that if this is not working, this shit isn't working, let me try something else. This is not working, let me try something else. While-- or taking a backseat altogether and I need to detox from all of this. I see that happening. It's just in every generation, let me focus on something else. Let me come back some months later. I had at least the good fortune of not having family breathing down my neck. Also, I remember giving what I'd describe as the speech of my life then, when I was thirty-one maybe, and my mom asking me while on a long-distance call, I was in Seattle. I still remember where I was in my house then, my lovely new house that I had custom-built. And, "Oh, beta, what about you? When will you get settled?" My older brothers were married by then. And I made a case that, "Hey, look, it's not as if I don't, uh, have any ideas of getting married." You've known-- She even sent token, uh, gold earrings to my first American- Mm ... girlfriend, who was called out, not called out for it. A coworker would say, "You must have an Indian boyfriend because you're wearing these shiny twenty-two karat yellow earrings." Yeah. Indians go for twenty-two karat yellow. Americans, maybe eighteen karat at most, fourteen karat that sells better with their- Skin ... Caucasians with their lighter complexion. Uh, so you know that I've had not just intent, but even, uh, demonstrated intent to find a life partner, having chosen not just once, but twice. What will be, will be. Uh, and you may worry that I'm not giving it due time and attention, but I also have my aspirations, 说 话 的 艺 术 , life में कुछ बना, want to be something, want to do something with my life meaningful. And I told her that my wish was that I would not get so caught up with what is going on, that I would not be like a horse with blinders. Or even if I were, I would at least notice this pari that might cross my scene- Mm ... that I might notice some fun. Wow! Yeah. Where was this woman all along? That my eyes were open. And I said that, "Of course, um, I, I would let you know when I would find that person. I would hope that I would find her sooner rather than later. But please don't keep bringing it up, because it only reminds me of the thing that is missing in life." Your heartbreak. No, not, not so much heartbreak, but don't remind me that life would be more fulfilling with the right person. Mm. But today, I counsel folks, younger folks, that I would rather wish that you were... When you're twenty-nine and stressing about, "Oh, I'm going to be thirty, I might be seen as an old maid." I would rather that you're thirty-one and still discerning and single, rather than get hastily hitched at thirty. Because- Correct ... look at the irony. I got married late in life. I found, uh, the person that I eventually married at thirty-eight, just shy of my thirty-ninth birthday.... after a whirlwind coach trip, this was a couple of years into building Jodi365. So I founded the parent company in Chicago in the spring of two thousand and nine, and it was clear for me at the very beginning that I have to be in India. This has to have a presence in India, too, for a combination of reasons. I saw that, first of all, um, my mindset had shift. I was no longer like the average consumer of these platforms. I thought that here I am going through this top-tier MBA program. I'm investing in-- screening and investing in startups. I'm recognizing this unsolved problem, which is affecting not just me, but so many in my peer group. This, uh, underserved segment could use a better solution. Let me go and do a better job than these bozos out there, the prevailing matrimonial sites.

9. 55:28 – 1:13:40

   Is introducing AI in matchmaking a threat or opportunity

   1. SKS. Anil Kumar55:28

      While also recognizing that people in my peer group were not quite ready for a chatmangi patbiya kind of solution, who would, as in, get chatmangi patbiya engagement, quick engagement, quick, uh, wedding. Who would want to get to know somebody over time-

   2. AMAmrut55:46

      Yeah

   3. SKS. Anil Kumar55:46

      ... at least organically. If not organically, semi-arranged.

   4. AMAmrut55:50

      The way you are describing your own journey feels a lot more human, and it-

   5. SKS. Anil Kumar55:56

      Yeah

   6. AMAmrut55:56

      ... feels like this is a story that's happening all around us, and-

   7. SKS. Anil Kumar56:01

      Yeah

   8. AMAmrut56:01

      ... everybody is navigating through these intertwining-

   9. SKS. Anil Kumar56:04

      Yeah

   10. AMAmrut56:04

       ... career aspiration, pressure to sort of make something of yourself, leave some legacy. At the same time, you have to spend time finding a partner-

   11. SKS. Anil Kumar56:12

       Yeah

   12. AMAmrut56:12

       ... and deal with the setbacks in that journey.

   13. SKS. Anil Kumar56:16

       Yeah.

   14. AMAmrut56:16

       And, uh, how that ties up with things like: "Oh, but I have to wait for three years for my green card," and, "Oh, but I have to wait for this other thing to finish," and-

   15. SKS. Anil Kumar56:25

       Yeah

   16. AMAmrut56:25

       ... uh-

   17. SKS. Anil Kumar56:26

       Yeah

   18. AMAmrut56:26

       ... the constraints that, uh, you know, life offers-

   19. SKS. Anil Kumar56:28

       Yeah

   20. AMAmrut56:28

       ... at various stages.

   21. SKS. Anil Kumar56:29

       No, it's a useful summary because, uh, I take storytelling quite seriously, and there may have been a couple of unfinished thoughts over there, but true, um, it's a real problem. I remember being on H-One V- Visa, and while going on dates with potential, um, girlfriend or people who may be wife material, understandably, being seen as a flight risk. "Oh, what if he loses his job? What if he decides to head back to India?" And that problem is even more, and not just... Even if somebody were in India. So I was saying that I counsel people to take their time. So my solution was not to introduce an alternative that took the form of a dating platform, because I would remind myself that this is still India, where on Valentine's Day, to this day, you have the politically motivated outfits-

   22. AMAmrut57:23

       Mm

   23. SKS. Anil Kumar57:23

       ... the Pakks and the Sanghis, who would want to make a point of harassing people who may be walking hand in hand and getting them forcibly married. Either call her your sister or make her your wife, to make a show out of it. Who would go and smash-

   24. AMAmrut57:39

       Some glass

   25. SKS. Anil Kumar57:39

       ... store windows of Hallmark.

   26. AMAmrut57:40

       Yeah.

   27. SKS. Anil Kumar57:40

       "Oh, Valentine's Day, you're poisoning the Indian youth." Chase men and women out of these cafes in Kerala, because what's this? It's a meetup place for dates. What is this? And chase women wearing jeans out of pubs in Bangalore. A smart alternative would be a hybrid between the prevailing matrimonial sites and emerging dating sites. So that was my- that was the genesis of Jodi365.

   28. AMAmrut58:08

       Nice.

   29. SKS. Anil Kumar58:08

       With the tagline, to this day, "Find the right partner," even while we make it, uh, we made it a personalized service. "Find the right partner at your own pace." Um, it was important for me to have a presence in India, because the times were changing so much in India, and young people were getting so much more agency to decide where they studied, where they worked, living away from home, not having a curfew as in, "Hey, you've been out until past ten pm. Where were you? With whom? Doing what?" When you have the kind of independence that comes with being on your own economically, you also have social independence, whom you choose to hang out with, whom you choose to get to know potentially romantically, whom you choose to date, and whom you choose to marry, and on what timeframe. And with all this flux that are happening, I thought that there was need for a smart, sensible alternative without leading people to get drowned in the swamp of emerging dating apps. And I stayed true to that positioning, even as I saw... And I look back, it's a dozen years ago, no, more than a-- two thousand and twelve, uh, when, uh, to their credit, there was a top-tier VC firm globally that had an outpost in, in India already. To their credit, they recognized that the so-called matrimonial space was ripe for disruption.

   30. AMAmrut59:31

       Mm.
10. 1:13:40 – 1:25:45

    Anil’s advice to young people navigating relationships

    1. SKS. Anil Kumar1:13:40

       family, uh, one of the first things that comes up is, oh, privileged family. Yeah, also-

    2. AMAmrut1:13:48

       It didn't sound like it at all.

    3. SKS. Anil Kumar1:13:51

       Thank you to the government.

    4. AMAmrut1:13:52

       I mean, from the history that you've narrated.

    5. SKS. Anil Kumar1:13:54

       Yeah, yeah. Reality is, uh, if I could, I could go about living life in the bubble that I'm, that I'm in. Despite, uh, also keeping it real and say that I have given up a lot to build this business, to go on this journey. At thirty, I built a lovely home for myself, a custom home for myself. I had a comfortable life, and I felt unfulfilled, and I didn't want to end up going through my full career and being sent home, "Here's a gold watch. Thank you for your service for the last few decades."

    6. AMAmrut1:14:32

       Mm-hmm.

    7. SKS. Anil Kumar1:14:33

       Uh, my father was kickass in this res- this respect, um, go-getter. Yeah, what better way than to pay tribute to him than by talking about how I probably take after him in this, in this regard? Dynamic personality. Would have been sweet if he were around to witness a son get such a national, huge national honour, without any lobbying, without taking sides and currying favour with whatever the prevailing administration may be. Going about one's life, following one's passion, being a good human being, that is what I'm proud of, of Ajit, because I see it as more an acknowledgement of his innate goodness and even his success. Oh, you know, unlikely actor, accidental actor, but he's good at his craft.

    8. AMAmrut1:15:27

       Yeah.

    9. SKS. Anil Kumar1:15:27

       Uh, but it's his Q factor. There's this term in marketing in the US among advertisers, big brand ambassadors who have these high Q quotient. Uh, Ray Romano, he was supposed to have a lovable personality, the stand-up comedian and-

    10. AMAmrut1:15:43

        Yeah

    11. SKS. Anil Kumar1:15:43

        ... behind The Romano Show.

    12. AMAmrut1:15:46

        Everybody Loves.

    13. SKS. Anil Kumar1:15:47

        Everybody Loves Raymond, right? Yeah, not Romano show. Ray, Ray Romano. Yeah, Everybody Loves Raymond. So Ajit has, I think, and Rajinikanth, right? Viviod, the kind of love and affection from fans, so it doesn't matter... And he says this himself, he's had more flops than hits. All the love of his fans and people who see him as somebody who sets a good example. So thank our parents for it, for striving to raise us well, do-

    14. AMAmrut1:16:17

        Did the, did the three of you, while growing up, sort of egg each other on? Like, did you contribute to each other's success by-

    15. SKS. Anil Kumar1:16:25

        Egg each other on? Uh, in a way, yes, I'll come to that. Contribute to each other's growth, surely. Uh, and here I have to take- get into specifics. Ajit and I were close in age, a year and a half apart, and it's only in my adult years that I reflected on how that may have influenced my personality in a way that, um, may be written in psychology books. I was the youngest one, always trying to show that, hey, I can do this, too. So he would ride a bike, "Oh, I want to show that I can ride this bike, too." So trying to do things that were- I was not quite ready for. And when- when the kind of things that we would do, parents would be horrified if they were to see their kids do this these days. Uh, climbing up, uh, ladders to the second floor, external ladders to a terrace, and hanging off sun shades. Uh, building a ramp, using a wooden stool and a plank to create a ramp, riding one cycle up the ramp and going off it-

    16. AMAmrut1:17:30

        Seeing how far you can go

    17. SKS. Anil Kumar1:17:32

        ... and just, yeah, taking off and landing. And I remember falling, taking turns and from our kid bike, and the lam- the ramp gave way just as I got my wheel onto it, and I was sort of mid-air, and, and I, and I, and I crashed, and I got a huge lump on my forehead. My mom was so distraught, and I felt bad because, uh, we had relatives visiting at the time, and they'd made plans to watch a movie. My mom was a fan of this late actor, Sanjeev Kumar. His most famous role may be that of the, uh, jailer, the warden, the inspector in Sholay-

    18. AMAmrut1:18:07

        Mm-hmm. Yeah

    19. SKS. Anil Kumar1:18:08

        ... who had his arms cut off by Gabbar Singh. Movie is fifty years old, huh? Milestone movie in Indian cinema. She had to skip it because she had to tend to this little kid who, her littlest, who got fever immediately. And yeah, we did those things because I was looking, "Oh, I can do that, too. I can do that, too." So it may be part of my personality to show that, hey, I can do it, too. And compound this with the immigrant mindset, going to a new entity, new country, new society.

    20. AMAmrut1:18:43

        In fact, you must have, uh, you- when you went abroad, Savir Bhatia also hadn't happened. Hotmail hadn't happened.

    21. SKS. Anil Kumar1:18:49

        Right. Correct. That came in '９６, I think. Yeah. So where you feel the need to prove oneself, that is the immigrant mindset. So I may have been influenced by being the littlest, and not just the littlest, but-... having a brother who is not that far apart that you think that, "Hey, I want to be able to do what he's doing," or, "He's getting to do this already, why not me?" In much the same way that even today, "Oh, my elder brother has a smartphone. I need a smartphone, too," right? So you fight for things before you may be ready for it, so you get pushed and challenged. Uh, although he was the more prodigious, uh, would take to things way ahead of his time. My eldest brother and I would, uh, be at loggerheads, so similar to, uh, like polarities repelling and, um... And he, in ways that he may not have realized, kept me in check. He bore the brunt of parenting mistakes. Every parent makes mistakes.

    22. AMAmrut1:19:53

        [chuckles]

    23. SKS. Anil Kumar1:19:53

        And then you realize when the second comes, "Oh, we should have done things a little differently, so maybe let go a little bit over here." And we would- we three boys were a handful. The two younger ones would do some shit, and he would, uh, bear the brunt of, "Oh, you were the older one, you should have reined them in," or, "How could you guys grew up in this way?"

    24. AMAmrut1:20:14

        Mm.

    25. SKS. Anil Kumar1:20:15

        We had a strict dad who believed in, uh, not sparing the rod or you end up spoiling the child.

    26. AMAmrut1:20:20

        Oh, is it? Okay.

    27. SKS. Anil Kumar1:20:22

        Yeah. But then, uh, I need to balance that with how we had friends from school days who did a double take when they noticed a huge contrast from the time that we were teenagers. "Wait, you guys used to have a terrifying, strict father, and you guys are so chill?" It's- we had a relationship that was like friends. We were very free, and maybe they realized that you got to let go. And they gave us so much freedom in ways that parents would worry about, uh, "Oh, what if they make wrong choices?" In contrast, both my parents would say this: "If you want to drink alcohol, drink in front of us. If you want to smoke, smoke in front of us," because it would hurt us if we were to hear, "Hey, look at what your sons are doing." Right? Own it. So I love this parallel to the Spider-Man line. What is it? With great power comes great responsibility. Something that I didn't realize then was with great trust comes great responsibility.

    28. AMAmrut1:21:24

        Yeah.

    29. SKS. Anil Kumar1:21:24

        They trusted us so much.

    30. AMAmrut1:21:25

        Yeah.
11. 1:25:45 – 1:28:01

    Closing reflections from Anil

    1. SKS. Anil Kumar1:25:45

       um, the kind of questions that I wish I could give bandwidth to, but I have a business to run. My professional responsibilities to my clients, to my teammates. But I say, uh, have a curiosity mindset. Keep learning, keep growing professionally, keep... I don't want to get into a clichéd first principles kind of thinking, but, uh, yeah, think big. I would like to think build- think big and do something with life. Think about building. Because when I was, um, going through my MBA program, this is a nice way to close, there was a professor who was quite popular, the kind who would be featured in Business Week as one of the top business school professors in the US. So he offered courses in entrepreneurship and also, um, uh, venture capital on commercializing innovation. He was, um, someone who earned his stripes as a VC, and he also had this adjunct appointment at the business school. So he would tell folks, one of his signature lines at- towards the end of the course was... And who are the folks? Who are the students who had been doing well in their careers, that they chose to return to school for an MBA to have even more stellar post-MBA career? "Don't settle for an affluent life of quiet aspiration." And that was the freaking life that I chose not to settle for. I was comfortable doing well, but I didn't want a comfortable life.

    2. AMAmrut1:27:16

       Yeah.

    3. SKS. Anil Kumar1:27:17

       I chose to-

    4. AMAmrut1:27:18

       Nice

    5. SKS. Anil Kumar1:27:18

       ... build and make an impact, add value. So I would encourage folks to look at ways in which you can add value. Thanks for having me.

    6. AMAmrut1:27:26

       Nice. Thank you for coming.

    7. SKS. Anil Kumar1:27:29

       Thank you.

    8. AMAmrut1:27:29

       It's very nice to hear you. You have a quiet sense of self-assured, um, way of- a very storytelling way of speaking.

    9. SKS. Anil Kumar1:27:39

       Thank you. Gol gol ke ghuma ke leta hun, but thank you.

    10. AMAmrut1:27:44

        Okay, thank you for watching. Uh, if you like the podcast, uh, leave a comment, share, subscribe, follow, um, Anil on his social media and his company on social media. That's it for today. See you next time.

Episode duration: 1:28:06