#091 The art of career transitions with Shiv Choudhury

#091 The art of career transitions with Shiv Choudhury

Most career transitions are treated like cliff jumps.
You quit the job. Burn the bridges. Bet everything on your dream.

Shiv Choudhury chose a different path.

When he left BCG to build a billion-dollar business, he didn’t go all in.
First, he faked an app. It didn’t even work.
But it taught him one thing: customers wanted what he was offering.
That was enough to move to the next stage.

He calls it “pre-to-typing.”
👉 A way to de-risk big moves by testing the most important assumption before you quit your job or raise capital.

Shiv isn’t just theorizing.
He’s lived it — and thrived.

His career spans P&G, BCG, co-founding a fast-growing startup now valued in the hundreds of millions, and launching a successful private equity firm.
Every move was intentional.
Every leap was tested.

In this episode, he gives a masterclass in how to evolve your career — without blowing it up.

He shares:
✅ The “pre-to-type” method for de-risking ideas
✅ Why staying in your job can be the brave thing
✅ His framework for deciding when to prototype, scale, or kill
✅ How a childhood trauma still shapes his risk-taking
✅ Why humility — not hustle — has been his edge

If you’re in a transition — or quietly planning one — this episode is for you.

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https://howtolive.life/episode/091-the-art-of-career-transitions-with-Shiv-Choudhury

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[00:00:00] Sharad Lal: Hi everyone. Welcome to How to Live, a podcast that explores ways to live a good life. I'm your host, Sharad Lal. This is episode 91. Today we are gonna talk about career transitions. How do we move from one career to another? And who better to talk this than my good friend Shiv Chaoudhury. Shiv started his career in a Fortune 500 company, Procter and Gamble, and then moved to a top-notch management consulting firm, BCG.

[00:00:35] Then started his own entrepreneurial venture, gross, which is doing exceedingly well. I think the valuations are in the a hundred million, somewhere close to a billion. And then he started a private equity fund. We are gonna talk to Shiv on how does he transition between careers?

[00:00:53] What is his process? What is the ambition behind it, and what advice would he leave the rest of us? So without further ado, here's Shiv. Hi Shiv. Welcome to the Heart Live podcast.

[00:01:05] Shiv Choudhury: Thanks. Share. That was very kindly said, and probably I never thought of my life that way, so thank you for saying it

[00:01:11] Sharad Lal: you are humble and we are gonna get into that. We are gonna talk about so many wonderful things.

[00:01:17] the first question I have is, why so many things you could have done? One thing, which you were doing really well and, and done well. Why so many things?

[00:01:27] Shiv Choudhury: My mother is someone who was a sculptor. She, she's been an artist, she's been a social worker. She's a successful business woman. And she used to say this one sentence, which I didn't realize was that impactful to me till very recently, which is a stool needs to have four legs.  

[00:01:43] And so if you're not balanced across so many different things that you do, you will never stand for a long time. that just stayed in. even from early school, I was trying to do all things. I was never a master of any, but I was a jack of all trades. I always live in the insecurity that I'm going to be a jack of all trades, master of none, but at minimum I want to be a jack of all trades.

[00:02:05] And that's kept me kind of fueled to do everything as many times as I can. 

[00:02:09] Sharad Lal: So Cool. So your mom was like, she went through artist as well as business, so two different parts and then social work and homemaker. That's right. The four parts of that

[00:02:19] Shiv Choudhury: stool. That's right.

[00:02:20] That's exactly the four parts of the stool. And she said, you can never let one leg of the stool get so long that the other things get, no matter how good you are, they get disbalanced. she believed in this entire, let's be balanced individuals and human beings.

[00:02:34] And, and that's just kind of stayed on without even actively thinking about it.

[00:02:38] Sharad Lal: I love that balanced approach to life. And it can come to life in different careers. It can come to life in different interests, but there are different parts to us, and I like that when one part, it's active management when one part of the stool is getting bigger than you manage it and, and get it all

[00:02:54] Shiv Choudhury: Absolutely. Absolutely. And I use it even on a daily basis. Actually, I say this week. You know, this leg is long. Sometimes it's okay if the leg is long, and I know I'm very conscious about it, but I need to find ways to balance it out.

[00:03:07] It helps with just keeping sanity, 

[00:03:08

[00:03:09] Sharad Lal: Now, one of the things I've also noticed, and a lot of our friends will have the same question, so I wanna put it through to you. When you transition from careers, you keep your legs in both places. You've done that a few times. So you've transitioned from, for folks who don't know from BC, G or a partner doing exceedingly well with BCG, and you started your business.

[00:03:27] But you did part-time b, CG, part-time business, and now when you're in your business, you're part-time business and part-time private equity firm. So why some people are like, let's burn the ships and go all the way, but you are like, you, you, you try and keep both together. What, why is that and how does that work for you?

[00:03:44] Shiv Choudhury: it probably stems from a sort of historical incident that happened in my life. So I think sometime around when I was like 15 or 16 my dad who had a very successful army career, he actually left the army and started his life 2.0, which is like a business businessman.

[00:04:00] And he was exceedingly good at the, at business. So he, he did think he would do really well if, if venture capital existed those days, honestly, I think he would've continued to do very well. But due to complete bad luck, due to some mismanagement by people under him, the, the business just went down. And unfortunately that had impact of massive proportion to all of us because I could see.

[00:04:21] Not just did, did I see our family go through, like we were, we were literally zero doubt, zero doubt. And we had like no money. We were in massive debt. We had debtors calling and knocking the doors every day. My mother would receive phone calls from people saying, I need to get this money now, or else I'm sending, I'm sending goons to your place.

[00:04:40] Police would come. So I've seen that and what that did to our family and what that did to him. And I can't go through that again. Honestly, I, I just don't want that. I cannot sit 10 years from now and say, I did this to my family. Again, knowing very well what the lessons of the previous generation were.  

[00:04:59] that shapes a lot of my economic sort of conservatism, if I might call it that. Until I'm absolutely sure that there's something that. It will work out financially. It's tough for me to make that chance even today after I don't need the finances.

[00:05:14] I think at the core of it, I cannot get, get past it. But that said, I think as I think about it now, it's actually given me so many benefits that I can't, I couldn't have articulated till I went through it. the ability to be on multiple pieces just gives you a perspective that you can connect the dots better than anyone else who's doing deep work on only one.

[00:05:37] Consulting taught me that because we were often working on 10 or 12 projects and I would see some of some of the people I've worked with had the ability to join dots like no one else, and I really wanted to learn that. So doing multiple things certainly helps in that way. It helps me personally, not have my back to the wall.

[00:05:55] Some people work best when their back is to the wall and they will fight hard. I personally, and I realize this about myself, I work best when I have nothing to lose. And I say I am actually playing in a, Indian cricket manner if I'm playing on my front foot. I, because I can put my weight into it, I don't have to care about what happens.

[00:06:13] Worst case, if my, you know, hit doesn't go, that's fine. I have, I have enough of a backup. So that allows me to be able to fly.

[00:06:22] Sharad Lal: I'm gonna dig into two, three parts of that. Firstly, thank you very much for sharing it just getting into the story.

[00:06:28] Many people, especially those who've grown up in developing countries, will associate with that where the uncertainty of money actually dictates their career path. And very often people want to remain a little conservative because that cashflow is very important. You don't want to lose it. And the path that you found for yourself was you keep that cashflow while trying something else, so you don't give up till you are absolutely comfortable.

[00:06:52] And then you realized about yourself that that's the way you even thrive. And, and we'll get into that. There was one part of the story which you had shared with me, if I could share that. I think because that was, that visual stuck with me when you shared that with me. And if, if it's okay if I can share that with, with folks, so. I know that you had gotten to a premier business school in India, which is the IIM Bangalore for folks who are not from India, that's one of the premier business schools, you were ready to go there for the fees, unfortunately the family did not have money, and you were looking at a loan the loan was not coming through, 

[00:07:27] until the last minute.

[00:07:28] You did not know whether you're gonna go to the school or not till in the last minute the loan came through, you got your train ticket and you went to that school. So as a 16, 17, 18-year-old kid or maybe even older, that kind of a thing in your mind has to be a difficult experience. Even the experience of people calling up your home asking for money has to be a difficult experience.

[00:07:51] And people may not have gone through it to that extent, but they can always look at when money is an issue, what impact does the family have? And that is a driving factor for many people. And I salute you for what you've done because what you've done is you still wanted to do something new, but you wanted to keep that continuity of money coming and you found your way to do it.

[00:08:12] So I just wanna highlight that, if that is, if that is fair.

[00:08:16] Shiv Choudhury: Yeah. It, it is fair. And, and I, I suppose this is a good time to also talk about you know, how I think of these kind of transitions. I think there is this heroic sense that people make of the fact that you need to leave all, that you have, jump from your boat into this new world. You know, your guns blazing, swords out, all of that.

[00:08:38] That's not who I am. I, I, I, it's not who I am. And very early in life I realized that it's not who I will ever be. And so, and in, I would say 95% of people are not like that and probably shouldn't. It'll, it'll completely destroy your home and it'll, I've seen very close friends who've run businesses when they weren't financially prepared because it was just the best thing to do.

[00:09:02] In their mind, they're seeing all these shark tanks, there's, you're seeing all these beautiful things that people say, but it is just incredibly difficult. unless you're destined to be in that 1% of all companies, you are not gonna make it. 

[00:09:16] you also talked about how hard it was 

[00:09:20] Maybe I didn't fully internalize it then, but I think we've actu I consider myself one of the luckiest people that has ever been. I, I tell my my kids that my wife and I constantly talk about gratitude because I could not have done any of this without the instances of luck that have fallen absolutely penny on Penny till It's a full stack of luck that has built me to where I am.

[00:09:45] Even every, I'll give you a small example of, of this, which is the example that you talked about I had a ticket to go to, to join a job because I didn't have the money for the, for the B school. So I was actually going by train to take up a job at a IT company. Unfortunately, the train got delayed by a day.

[00:10:07] That gave me the time to go to this one bank officer that my sister had told me, who's known to be this kind person who sometimes takes, you know, exceptional decisions. And he wasn't available till that day. So because my train got delayed, I could kind of go and see him that evening. sometimes angels just appear, he just appeared and he said, I don't know who you are.

[00:10:30] I have, I can see that your parents' family business and their economic situation is not good, but I like what I've seen in your eyes and I will give you this loan. And he personally guaranteed it as a bank manager to personally guarantee a loan that the bank is giving it was, was outstanding. this is where, these bits of luck that fall, fall to you.  

[00:10:52] 20 years later, someone knocked at my sister's door saying, I'd like a job and I'm not getting a job. she said, someone once helped me and my brother, so I'm going to give you a job. And that turned out to be that bank manager's daughter.

[00:11:04] Wow. It is absolutely insane. I cannot believe how the world just comes together and we got a chance to pay back forward or pay forward something that someone paid to us.

[00:11:15] Sharad Lal: That's such a beautiful story. Wow.

[00:11:18] Shiv Choudhury: Yeah, man

[00:11:19] Sharad Lal: It, it connected. I mean, there's so many wonderful things that you talked about.

[00:11:23] Luck and paying forward and paying back. You paid back to that same family that gave you something. And because of that luck, because of that train getting delayed, so many things have happened. You are here in Singapore, thriving, living, like you said, grateful for the life that you have that that bank officer's son has a job.

[00:11:42] So many things have happened. That's such a beautiful thing. I just want to touch upon that other thing that you talked about earlier about being the hero, because many people think that when you wanna be an entrepreneur, when you want to transition, we need to be that hero. And I think it's ingrained in Carl Jung called it the hero myth way.

[00:12:00] You want to be the hero of your own story. It's dramatized in Shark Tank, in movies, everywhere. So we want to be the hero. And I love what you said, that in reality it's a practical thought out decision. Because being the hero, you can gamble away what you already have and that isn't necessarily the approach.

[00:12:19] So I'd love for you to talk about your approach as you calculate between moves. And maybe we can talk about PNG to B, C, G or BCG to gross, any of the moves that you made, how do you calculate and do it in methodical way?

[00:12:33] Shiv Choudhury:  every time I try to make a decision, I ask myself.

[00:12:37] Is this a risky move or is this a not risky move? p and g to BCG was not a risky move for me because I felt at that time, at p and GI, I felt I, I'd done a lot of stuff and you, you and I have resonated over this, that when you're in a large multinational, you are a small cog in the, in a fairly big machinery.

[00:12:57] And I just felt like I was not being able to express myself and do as much as I want. And so for me, getting to b, c, g, even if it was a, it was a step down in career, I didn't mind the step down in salary, the step down because it, I just felt like it would give me a wider canvas to draw on. And so, you know, I often talk about it as, as sort of paintings and in p and g or a large multinational, very small cog, someone has already drawn out the dots and you're just coloring in some pieces.

[00:13:26] In one part of the canvas, when I went to consulting, I felt like I had the canvas. Where it was lightly drawn. A client kind of knew what they needed, but I could draw it the way I want, I could kind of go towards still life. I could go, go towards, you know, any kind of sceneries, whatever I wanted.

[00:13:44] And then in entrepreneurship, I felt like, you know, I can cut the canvas file first. I can decide what I want. And, and that kept me motivated. So when I look at transition, the first decision that I take is, is this risky and is it in line with my sort of goals? I found p and G to BCG was not risky. B, CG to entrepreneurship was a massive risk.

[00:14:04] It was just a stupid decision to be honest. If I, if I didn't think about it well enough. So when it's risky, the first thing I ask myself is what gives me confidence of success? the methodology I use is something that I, I learned actually from a Google person who, who uses the word called prototyping.

[00:14:23] Right? Prototyping is a very interesting, it's not prototyping. It's prototyping. And what prototyping is is a sentence that says build the right it before you build it. Right? it's one of the most important things that I have learned in life that before you build it right, and jump into saying, I wanna do a great job of it, first, figure out if you're building the right it and what's the best way of building the right it.

[00:14:47] Ask yourself the top two or three questions that will help you answer that this is the right it. And then just put a test in place, a cheap, quick, not scalable, not proud of test. And if you can put that and it looks like it's working, then it is worth proceeding on.

[00:15:01] And that's why you can scale. 

[00:15:03] Sharad Lal: So maybe you can talk about grocery. What were the two, three things that you wanted to test and how did you preto type it? And then how do you get the confidence to actually go full time?

[00:15:12] Shiv Choudhury: what Gery does is we work with small businesses, which are typically small retail stores. So they're called Sari Sari stores in the Philippines, and they're the mom and pop stores which serve the communities.

[00:15:23] Now these guys. They need some products so that they can get it into the store and then they can sell out. what happens is you shut the store, you leave your kids at home, you go to a large wholesaler, stand in queue for a couple of hours, bring the products.

[00:15:37] It's usually heavy. These are usually women in, in the Philippines who are running the store. And you do all of that. And now you've basically brought the product home. If you think about it, it's a problem that e-commerce has solved, right? And so we asked ourselves, can we use e-commerce? what we had to prove was one core hypothesis, right? The core hypothesis was, if we give these stores a way to digitally order, will they do that and will they prefer that versus physical exercise of shopping at a store. So we put an app. There was nothing behind it.

[00:16:09] We just put an app in there, so, and said, just order. The order honestly went nothing, nowhere. We just got a message saying that someone has ordered, but we were just testing to see that they would

[00:16:18] Sharad Lal: ordered. Mm.

[00:16:19] Shiv Choudhury: and then that, that gave us sort of some suggestions when in the initial days we saw that it was working very well, but there was a few things we take.

[00:16:27] We tweaked it around and then we realized that actually of 50 people that we just gave the app to 45 of them at least, were browsing and they were doing stuff

[00:16:35] then we said, now is a good time for us to say stage one looks like it's done. Now let's get some partner. We don't wanna build out a supply chain, but we can we get any retailer. We just got the nearby wholesaler and said, you are going to act like a fulfillment center.

[00:16:51] We would literally get the order. We would go shop there, buy stuff, put it in our car, ditch the car a block away, because obviously the store shouldn't see a car and then we put it on a cart and take it to the store and see if that experience jelled. And so you just have to build a block at a time till you are confident.

[00:17:07] When we were able to have that confidence, that's where we went out and raised. Once we could raise, my co-founder could leave his job when we raised a bit more, my second co-founder could leave his job when we raised a bit more, I could leave. So that's how the sort of progression has been. But at every time we ask ourselves, is this.

[00:17:25] De-risked enough for us to put more effort and money into the next phase, and that's how we think of prototyping.

[00:17:31] Sharad Lal: I love that approach. 

[00:17:32] Shiv Choudhury:  So taking a step back as you transition, you talked about de-risking, you talked about prototyping. Are there other things that you consider as you're thinking about transitions?

[00:17:43] the part where I spend a lot of time is what if and what if not. And I think being very, very, very express about what if this goes wrong and at what point will I cut the lines to this is necessary.

[00:17:59] Because at the end of the day, all of us are managing energy. And even if you're doing a prototype, it takes energy. So I always, I think you and I have talked about how I, I break my life into things. I'm prototyping. Things I'm scaling and things I'm killing. And so knowing when to kill something much before you do it is, is necessary I think, because you can otherwise get into this swampland of running 50 pilots about your life and 50 prototypes and, and then not knowing when to chop them.

[00:18:27] And you just don't have the energy to do any Well,

[00:18:29] Sharad Lal: you are a naturally enthusiastic person. You, you get drawn to great ideas, but you also realize that energy is finite and you need to manage your energy.

[00:18:39] And I love the system that you've created that, all right, I'm gonna be prototyping a certain number, whatever that number is. And it cannot go more than that. I'm gonna be growing and scaling a few, and I have to close some because I cannot have all these in the thing. So you have three funnels where there's prototyping, there's scaling, and there's closing.

[00:19:00] And I guess a lot of your time goes in scaling once you've prototyping is a certain percent, and then a lot of time in scaling.

[00:19:05] Shiv Choudhury: That's right.

[00:19:06] I think you've, you've made it sound like I'm a lot more methodical than, than I am and I wish I was. I, but I think in general, those are absolutely the principles that we have because, like you said, the fundamental person that I am, you throw a ball, I will run behind it because I just, I just love chasing new things.

[00:19:22] I love new experiences. And so it, if I don't do that, life just gets unmanageable and back to, you know, how do you balance the four legs of life Professions itself is one leg. Right? And how do you balance all the energy? So I found that I have to get better and better at, deciding what to push into the sort of kill bracket and what and when to push things into scale to scale.

[00:19:44] Because when I scale something, I really need to put the energy in.

[00:19:48] Sharad Lal: Is there a process that you have a reflection process every two weeks you take stock that, Hey, I haven't gotten any new idea into this, or what, is there a process that you follow for

[00:19:56] Shiv Choudhury: I think the pro new ideas, I, I get so many that I, I struggle to put them into the funnel.

[00:20:02] So the process I have is the new ideas into what should I test kind of bucket. And then the second thing that I put spend a lot of time on is, is this worth pushing any more or has, you know, is there nothing coming out of it? Those two places is where in the funnel I spend the most amount of time for the first one, which is, should I do this or not?

[00:20:24] I found that over time, it's not the science of it, but it's just the feel and the gut feel and the who is as important as the what. Because I've realized I, I'm not a, I'm not a lone wolf. Anything I do I need to do with partners. So finding the right who and who's the right partner is as important or if not more important than what I'm doing.

[00:20:44] Sharad Lal: So we'll talk a little bit more about killing, 

[00:20:46]  how easy is it for you to say no and just leave things aside that are not okay?

[00:20:51] Shiv Choudhury: That simple answer is tough. It's so tough. It's tough be, and it makes me feel bad. It makes me feel like a failure every time I do it. And even today, I think if I, if I have 50 pilots and or prototypes and of them, 47 of them fail, I, I feel like I'm a failure 47 times over. I, I don't, I, there's no way.

[00:21:11] No other way in which I can truly invest myself into those prototypes and not feel bad. Like I would, I would have to be super heartless to be able to do that. But I have just learned that if you cannot take that balanced call to say all things considered, this is not going to work. I'm not, I'm not benefiting anyone.  

[00:21:30] what I've learned is that the best way to, to channel my energy is to say the other three that are working. I'm so excited about them that I'm going to use that, the, the disappointment from those 47 into the positive energy that the three can get me. But that's, it's tough every single time and we often, you're not working on it alone.

[00:21:50] Right. So someone else's whose life depends on this is being told that, okay, this is not the project. Let's move on to something else.

[00:21:58] Sharad Lal: Well that's, thank you for describing that. And I just want to underscore, so when you take something on, because you go with full passion, you have to go all in and When it doesn't work out, it is completely disappointing. So there's an emotional management that you need to do, and once you do the emotional management, there's a rational call you need to take that this does not work. Now How, how do I sort out this not working? Yes. And one of the motivations that helps you is there are three other such exciting pieces.

[00:22:26] Let me focus on that so at least I can put my energy and get some positive 

[00:22:30] Shiv Choudhury: That's right, that's

[00:22:31] Sharad Lal: Wow, that's, that's good for people to know then this whole killing process.

[00:22:35] Shiv Choudhury: it's, it's not easy it's a acquired skill. It's a muscle that you build over time. And I, I don't think it takes away any of the energy I put in, into every prototype, even though I know that there's a probably, you know, 10% chance it'll survive.

[00:22:49] But it's worth it.  

[00:22:50] Sharad Lal: something I've noticed about you is you're still very humble. Like you've, you've, you've gone and you, you, you've done these four things. You've, you've, you've got a dream career path, but you're humble and sometimes you even make sure somehow there's something controlling you to make sure you're humble.

[00:23:07] What is arrogance to you and what have you done to stay away from arrogance and stay humble? Like how does this whole play out in your life?

[00:23:15] Shiv Choudhury: a, this is a sensitive topic because I'm working on it humility is good, but not always good. And I, I'll describe a story from childhood actually that I'm still trying to get over.

[00:23:26] As you can see. So I, I, in school I was, like I said, because of influence of parents, et cetera. I was doing everything. I was playing sports, I was debating, I was good at academics. I, I did whatever I could in school. And I thought, as did everyone around me that I was an obvious choice to be a prefect when they had to choose six people from my house.

[00:23:45] And I. When the, when the list came out it, I, I, I smile now, but I was, I was utterly disappointed to see that there were not six names, there were five, and I was not on that list. So not just did I, not, I not just was I relatively beaten by other people, which could happen if there were six names on an absolute scale.

[00:24:04] They decided that I didn't make it, and that was crushing. And it was crushing enough for me to like not go to school for a whole week. And my parents went and talked to the teachers about this, that was a slow, but a critical, important learning for me. That performance is not everything. You need to have performance.

[00:24:24] You need to have a certain exposure of the performance, and you need to have a certain imagery, thus, that people carry about you. if you remember from our old p and g days, this is a model I learned about at p and g called PIE, of course. Performance for P is absolutely critical, but you need to have an imagery, you need to have exposure to the right people making the decisions.

[00:24:45] And till today, I think I struggle with it because I, I don't, I swing the pendulum still too far. Very Asian style, if I might call it that generalization to what I think will be if I do good work, you will notice me. If I do great work, you will come to me rather than me needing to put myself out there.  

[00:25:07] that comes from, I think, an insecurity. It comes from a place where I don't want to be, you know, that guy who's out there beating his chest. So I, I suppose it's not ideal, but I'm trying to get better at it and I, I, I see so many people probably you know, go through the same journey as I am.

[00:25:27] Sharad Lal: That's such an interesting area.

[00:25:29] So as you are figuring that out for yourself, you say you don't wanna be the guy who's completely chest thumping all over the place, but at the same time, you don't wanna be the quiet guy quietly performing with nobody. Noticing where are you landing up, what are you thinking? Is there any steps, experiments you're doing to see what works for you?

[00:25:47] Shiv Choudhury: This is a, this is a good experiment as any right? This being on your shore right now. This is not comfort for me, but I, I've recently been part of more speaking engagements. I do believe that me being able to, to talk about what I stand for and getting the, getting the word out there about what I believe in.

[00:26:08] And thus telling myself that I'm doing it to, help others. That helps me think through why I am doing it. It's not for personal glory. I'm doing it because I think it could be helpful. I think I've always found that when I'm speaking in town halls at grocery, when I'm talking when I used to talk address large meetings, even in my previous jobs, I always found that I would be at my best when I said, this is necessary for the company.

[00:26:33] This is necessary for the people and it's not about me. And so that's, that's what for me personally helps. And the balance is a little bit focused on my work. And once my work is done, I kind of get to the next level of, let us now talk about this work because others might benefit from it.

[00:26:50] Sharad Lal: I love that. Changing the focus from yourself to the bigger thing reduces the need to be humble then it's that it's, it's nothing to do with, you're not going in the chest thumping land.

[00:27:00] Right. When you've done some of these experiments, how has it landed for you? How's the reinforcement been after that?

[00:27:08] Shiv Choudhury: It's been actually excellent. I, I, I must say a lot of the demons are in my own head, right? As with these things, nobody genuinely cares so much about what Shiv said and who shiv is.

[00:27:20] They just care about what I said and whether that resonated with them. It doesn't matter if maybe there are days when I'll sort of on, on a margin, I'll be a bit more out there on mar on days. I might not be. Honestly, no one cares. This is not about me. And I think that realization I need, I when I can, when I'm, when I'm at my best, I'm able to keep that realization front and center.

[00:27:42] When I'm not at my best, I sometimes lose it. And that's the journey that I'm taking forward that people do care about. What you say, less about who said it and how arrogant you sounded when you said it.

[00:27:54] Sharad Lal: in a world where a lot more smart, quiet, humble people come out and talk is a much better world.

[00:28:01] So if there are many others listening who are scared that, I don't like this guy who's chest thumping and talking about it, why don't you come out in a nice way, think about not yourself, but think about the bigger world and actually put something out there. The world will be actually better because you can tell things that are beautiful, passionate, authentic, which come out out there.

[00:28:21] Shiv Choudhury: Absolutely. I, I've, I've personally seen you from a distance as you've gone through the journey, because I know you are not, you were not this such many years ago, and I've seen you make that journey and I've taken inspiration from yourself, people like my wife who've all kind of made that journey to sort of put themselves a little bit more out there and yet not swing the pendulum too much.

[00:28:40] Sharad Lal: Thank you. Thank you for saying that. The other thing I really want to talk about is ambition I, and we've talked that earlier, but I'd love for folks to hear that if somebody looks at you and they'll say, you're such an ambitious person, you're going from one, one height to another height, one peak to another peak.

[00:28:57] What do you think of ambition in yourself? Is there ambition? What is there? Like what, what drives this?

[00:29:05] Shiv Choudhury: I've thought about this quite a lot and it's easy to paint some things as sort of broad brush ambition, but what I feel has worked for me is not ambition itself but just a drive to make impact of some sort. And it's rarely about the end in mind for me. It's, it's not like I want to have a billion dollar company or I want to have a VC that has returned X amount to sort of the LPs that are there, or I don't want to be the most successful partner there was at at BCG.

[00:29:38] For me, it's a lot of it is about just thinking about the means. I say, I want to be able to do this. If I can do this, I'm excited and I will jump to do stuff. Half the time, it doesn't result in anything. But I know that I'm having fun, I'm having fun, I'm doing something. I'd say my ambition is heavily dependent on whether or not, or my definition of ambition is based on what I think is fun.

[00:30:05] And I'm sure many other people have. I want to be this, that just doesn't drive me. One other thing that I've realized is you know, if you've done the Gallup Strength test for me, the Gallup strength number one test is significance. And I realized that I derive significance not by what I have delivered, but I del I derive significance by what I'm doing now.

[00:30:27] And I am starting a business that gives me significance. I am learning how to play paddle. That's significance. It's not he's the best paddle player or he's the best sort of entrepreneur that those things don't, but I still derive significance from doing.

[00:30:45] Sharad Lal: That's so cool. That's very rare. Is there, and that's very spiritual as well, so I don't know if it comes from a spiritual play, because if you go to ancient Vedic text or any of these, it's all about doing, it's about the process versus the, the journey versus the end.

[00:30:59] Is there a spiritual thing or is it just this is the way things just happen for you?

[00:31:03] Shiv Choudhury: I find a lot of resonance in the spiritual sort of parts that I, my parents are both fairly spiritual people.

[00:31:10] My wife has over the last 10 years really taken on spirituality and I feel like I have absorbed from them some of these things. But I've just been blessed. Like I said, I'm, I'm blessed and grateful for just things that came a bit naturally to me. So for me, somehow, naturally it's always been about the means and not the end.

[00:31:30] I always loved, for example, that p and g people cared about. How, how much was your market share? How much was your sales of that month? I cared a lot more about did we, this last month have a good time with everyone on the team? Did we feel like we're doing good work? I could never measure it, but it would be a lot more satisfying to me to see that didn't always make me the top performer, but it was just something that kept me going.

[00:31:54] Sharad Lal: That's also a little bit about the gut that you talked about, so it's, it's more connection with yourself and gut.

[00:31:59] Shiv Choudhury: Absolutely.

[00:32:00] Sharad Lal: One of the things that a lot of folks in their forties, late thirties and forties face that, what am I doing? And that's when they're thinking of making changes. But you did a huge amount of work, whether it was coaching, I think maybe some spiritual work, some yoga practices. There was a lot of things that you went into doing which then helped you emerge.

[00:32:20] So what are some of the things that you did during this time that you'd recommend for people to do? 

[00:32:25] Shiv Choudhury: So sometime around maybe when I was 20, and it's as back, far back as 20, I realized that I benefited a lot from just.

[00:32:35] Looking at what, what's around me. I sometimes it was negative because it became pure comparison. Sometimes it was positive because it just gave me fresh perspective. But I've just continued that as a sort of core way of living for, since, since then. And it might be that I go and learn about how this business is run in another country.

[00:32:56] I, I learn about, you know, Shera, what are you doing as in, in time today? And what, what are you thinking of your next career? And things like that. So it just is just absorbing a ton of new perspective every day. And then being able to distill it down into do I feel like I want to test this in one of my three buckets that I talk, talked about.

[00:33:16] But I do a fairly, I would say it's now become very ingrained in me that every time I talk to people, I, I try and see what else is out there. And that I think is a very, very critical part of making any transition, because if you don't know what's out there, you just have no idea of the pros and cons of it.

[00:33:32] Right. And you know, it's a, it's a slight deviation from what you asked, but one of the things this peer benchmarking taught me is I thought when I was in school that I was a hardworking guy. I was hardworking, I was studying a lot. I went to college and I realized that I would go to bed and I'd wake up every day and I'd see people awake already studying, and I would be, then I realized that, wait, my, my sense of what hard work is was two hours of studying a day.

[00:33:58] I went there and I realized the true peer benchmarking of this is you need to be studying 15 hours a day. 

[00:34:04] And then I came to p and g where I realized that actually it's not hard work. People who are successful here, people who are doing well, they are people who know how to take their intellect, convert that into meaningful ideas and plans, and work with people to deliver it.

[00:34:19] And that created, oh my God, this is a new dimension now. Nobody taught me. And so I benchmarked to that. Then I got to consulting where people like redefine what 24 R means, right? And the amount of depth and width you can cover, the amount of client depth relationships, building that you can do. And then as you know, when you get to entrepreneurship, the game changes entirely.

[00:34:40] So I think at every stage, looking around and figuring out what's the big. big next jump enabler, then thinking about how to incorporate that into your life is something that I've, I've almost ingrained as a way of living. that's something I always use when I'm thinking of what's next.

[00:34:58] Sharad Lal: I love that. If I can go a little deeper into it, so there's inspiration of this is what it takes in this system, let's say consulting to succeed, but this is who I am. So how do you think of, how should I make that move? Like, do I go through my strength?

[00:35:11] Do I try something different and, and stand out? How does, how does your approach work when you enter a new world and understand this is what needs to be done in the world?

[00:35:21] Shiv Choudhury: And we both talked about how, you know, even if you join a consulting world, for example, where you come from outside, you're basically, it's a fast treadmill that you've suddenly jumped onto, right? And so you have two choices. You either say, I'm gonna just forget everything.

[00:35:34] I know I'm just gonna run super fast with that treadmill. Or you say that, Hey, wait, I know how to do this slightly differently. I can push some buttons and reduce some speeds and, and go like still deliver what I need to. Same calorie burn possible in some other ways. And everyone I always start off with first, just like instinctively running as fast as everyone.

[00:35:53] And then when I look around and I can do the proper benchmarking, I can see what's different about me. I'm able to press some of the other buttons, 

[00:36:00] I know one of the things that is also important to you as we are coming towards the close of this conversation, we can, we can talk for a few more hours, but we have a limited time, is impact and purpose.

[00:36:12] Sharad Lal: And you talked about your story of your mother in the beginning who used to do a lot of social work and that was inspirational to you. So can you talk about what does purpose and impact mean to you and how does it come to life with you?

[00:36:26] Shiv Choudhury: Purpose is something I've obviously pondered a lot about. And I've come to the conclusion that I can't say I have purpose to do something very specific.

[00:36:34] I don't wanna put man on Mars or something of that sort. But where I derive the most sort of depth and pleasure is when we've made a difference to someone. And so my purpose, if I is making a difference to as many people in whatever way, big or small, I think I talked earlier about the bank manager who helped me and, and that has such an indelible effect on me because I think.

[00:36:57] Even without me knowing it. If I can improve someone's life by a little bit, that would be great. Ideally, in, in my early life, I felt like I was making that by making better shampoos and better conditioners, which was honestly a little bit helpful. Then I said, let me make big impact to companies through consulting where then all their employees and all of that benefits.

[00:37:17] Then I'd say, can I do this with entrepreneurship? Where we have today at grocery we Visa, we have around five to 6,000 people who work on our roles. We are the largest women entrepreneurship platform. We have one 50,000 women that we support. So that was a wider scope. And now with venture capital, the question is, can I support companies who want to do more of this?

[00:37:38] So it's all about scaling the impact as much and as much as possible. And that I would say is impact and purpose for me. If I can keep doing that in any form and shape it's a life decently lived, I'd say

[00:37:50] Sharad Lal: A hundred percent. I think people may have missed hearing that your company, gross has the largest number of women entrepreneurs in Southeast Asia.

[00:37:58] Shiv Choudhury: That's right. That's right. We have 150,000 women entrepreneurs. We call them womenpreneurs. And we are the largest platform that supports them making a livelihood.

[00:38:08] Sharad Lal: Congratulations. That, that's fantastic work.

[00:38:10] Thank you. What's the bottom line advice? We've gone through many things. What's the bottom line advice you would give to someone who's thinking of transitioning?

[00:38:21] Shiv Choudhury: I'd say step one, listen to your gut.

[00:38:24] Sharad Lal: Mm.

[00:38:25] Shiv Choudhury: Step two, don't listen to your gut. Plan it very, very efficiently. Think about it like you were doing a business plan.

[00:38:34] Make a.

[00:38:35] a

[00:38:35] transition plan that really matches the degree of risk that you're 

[00:38:40] Sharad Lal: 

[00:38:40] Shiv Choudhury: So burn down the risk before you take any major actions. Everyone has different abilities to take risk, know your risk ability, but burn down the risk to that amount and not more than that. 

[00:38:53] Sharad Lal: Last question that I ask everyone at the end of your life, how would you know you've lived a good life?

[00:39:00] Shiv Choudhury: if I could say that I'm a balanced tool, if I have the, if I have said that in large parts, all four legs of my stool have been pretty balanced I would say so. And you know, obviously a critical part of that is career. A critical part of that is family. A critical part of that is companionship and friends that, that we have, and the last part of it for me is impact to society.

[00:39:24] So if I can do all four of those and do them in decently equal measure, I would say that it's a life well lived.

[00:39:31] Sharad Lal: You're living a really good life. Thank you Shiv for spending the last hour with us and thank you to your mom for this beautiful wisdom that has made it to the world through you. Thank you very much. I love the conversation. I'm sure people are gonna get so many deep insights and even get, I think your close friends will get to know you better as well.

[00:39:49] Shiv Choudhury: Thank you. Thank you so much for having me. It was great fun actually.