From IT Staffing to AI Builder: One CEO's System for Finding Opportunities and Failing Fast | Eshwar Prasad | Part 1

This episode is about what a founder actually does when he decides the next opportunity requires starting over.

In Part 1 of this conversation, Eshwar - CEO of a global IT staffing company - breaks down why he handed day-to-day operations to his team and went all-in on building AI products alone, 16 hours a day, with no traditional development background.

This wasn't a strategy retreat. It was a constraint-driven decision.

We cover:

•  Why Eshwar stopped running the business he built to go build something new
• How AI collapsed his test-and-fail timeline from six months to a week
• What "vibe coding" looks like for a non-programmer operating at full intensity 
• The childhood scarcity that built his tolerance for uncertainty
• The partnership that scaled fast and fractured - and what he took from it 
• Why he doesn't use the word "risk" - and what he calls it instead

If you're a founder operating between what's working and what's next, this conversation will feel familiar.

This isn't a highlight reel. It's a real look at how a seasoned operator makes the decision to go back to zero - and what it actually takes to function there.

Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.

New episodes release Tuesdays and Fridays.

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Transcript

Visionary Work And AI Speed

Eshwar 0:00

So I have a company, so that that feeds me and it kind of makes me money. Most of my time is spent in finding the next big opportunities. I kind of look at myself as a visionary that wants to kind of set the set the course for myself and the business at the same time. You know, there's no uh silver bullet. I mean, you just try different things and and see if it works or not. What AI is able to do is to give you uh cut that time into probably one-tenth of the time for you to be able to try and then say like it doesn't work. What used to take six months in a year probably takes about a week. So you know the results immediately, and then you you you pivot and then you try to do something else. So I I truly believe in in the process, not the results. So I um I'm Eshwar. So I run an IT staffing global staffing solutions company called Services. So I'm the CEO right now. Um apart from that, I have also been um you know looking at um starting uh a few companies within the AI sector. So I've been kind of neck deep in that in that aspect of it in the past three, four months. Um so so yeah, most of my time is uh you know shattered between. I would think most of my time right now is is um you know is spent on uh AI and and and nothing else.

Reshma Vadlamudi 1:25

Okay.

Eshwar 1:25

So non-stop.

Reshma Vadlamudi 1:26

Okay. So are you when you say AI, are you investing into it or uh what role do you play?

Eshwar 1:33

So um so I have a company so that that feeds me and it kind of makes me money. So it's it's pretty successful and fast growing. Um we're also looking at to expand into Latin America right now. So I have a team that takes care of it, and and most of my time is spent in finding the next big opportunities. So so I I kind of look at myself as a visionary that wants to kind of set the set the course uh for myself and the business at the same time. So so I've never been a big programmer, uh, so I kind of worked in the IT industry uh and I was mostly in the support side of things. Um where something breaks, you call me and I take care of the stuff. Um but I think I'm getting back into kind of the term called wipe coding, so which you use AI to be able to code for yourself and see what it's able to build out. So I'm in that transition phase of building a bunch of products right now on my own with nobody's help. So it's kind of a learning curve, but I'm kind of getting used to coding with AI. Um so most of my spend now, I think 16, 17 hours a day spent on just live coding and nothing else.

Reshma Vadlamudi 2:48

Okay. Um so you said like you are the visionary, and you are the one who has this big pic big picture thing for your company. So how do you know what to do next? And you said like you spend most of your time deciding what's your b next big opportunity. So we all want to do all these things, but how do you decide like this is the this is the right next thing?

Eshwar 3:21

I mean, you just try different things and and see if it works or not. Um what AI is able to do is to give you uh to cut that cut that uh time into probably one tenth of the time for you to be able to try and then see like it doesn't work. Um so so in that sense, like you know, um you you kind of uh read a lot, you know, listen to a lot of podcasts, understand uh various aspects of the economy and how everything is shifting. Um, and then you kind of take certain bets, um, you know, certain certain risks, right? And then and then if it comes off, it comes off. But it doesn't take a long time for you to be able to try something and then fail. So what used to take six months and a year probably takes about a week. So you know the results immediately, and then you you you pivot and then you try to do something else.

Reshma Vadlamudi 4:13

So you adapt. Yes. So it's all trial and error. Trial and error.

Eshwar 4:16

Yes, trial and error. But you need to also have uh to have to build a sense of um knowledge uh and wisdom over a period of time. Um and that comes with listening to a lot of things, reading about a lot of things, following a lot of things, and all the experiences that you have along the way will definitely help you figure things out fast. Um but uh but again, you know, I'm I'm no different from anybody else. So I just try to do things and uh and let it fail because that's how you learn. So failures and failures is when you learn a lot of things. Yes. So I don't don't do not fear of failure, and I just do things and and see if it works and something will stick. Yeah, as long as within the in the process you're learning something new is is what it's what what's gonna keep you drive, keep keep you driving.

Reshma Vadlamudi 5:06

Yeah.

Trust The Process Over Results

Eshwar 5:07

So I I truly believe in in the process, not the results. So I think the process is is is is being able to put in time and hard work and effort to be able to listen and uh and take a stance off the world and then do things differently.

Reshma Vadlamudi 5:21

Yeah. So how important do you think is risk taking to be successful?

Eshwar 5:28

So you kind of define that um is is risk taking, but I kind of think of it, uh think of it as not having a fear of failure, right? Um I think with anything that we do in life, for example, if I want to just you know take take the glass of water and then drink, I'm not thinking about, you know, if I'm able to do that or not. The my clarity of thought is very, very easy that I can just grab that glass of water and drink.

Reshma Vadlamudi 5:57

So you're not scared it'll fall down.

Eshwar 5:59

Yeah, because you're not creating any type of uh you know um implications within your head, you know, what if can I drink it in the middle of the podcast? What would she think? On all of those things, then you probably say, like, okay, I'm gonna let it be.

Reshma Vadlamudi 6:14

Right?

Redefining Risk As Fear

Eshwar 6:14

But if you have a clarity of thought in being able to do something and you don't have fear, you do not have any fear and doubt, um, and I think that's that's what that's what is needed, you know, uh to make sure that you do whatever you want to do. Because, like all of us, you know, we've come to the US, and if you've not thought about it and you've not had any um, you know, negative thoughts about whether you're gonna be able to make it or not, you would not be here. So, but we just we decided to do something and then we just pursued it without uh without fear and doubt. So, so that's what is important. Um, a risk is uh is a term that people often throw um throw around. Um, but at the end of the day, I look at it as no fear and no doubt. Anything that you do. So, and then you have a clarity of mind, and then you'll be able to uh pursue anything that you would want because you're not thinking how many how how different ways you can fail. You're only thinking about how different ways you can succeed at that point. So, so that's what I think is essential. Um, risk is just one of the metrics that gets thrown around in that in that mix. Um, so and it's uh it's it's uh it's um it's it's it's made to it's made to fe make you feel like uh you're not doing the right thing. So um, but yeah, anything in life is risk, and if I walk, you know, it's a risk, I may fall down, right? I mean you don't think of it uh uh like that, and then I probably drove here and I might get hit by a bus. You know, like it's it's just it's just risk. Everything you do in life is risk, but I think we tend to kind of give that risk a lot of a lot of um you know significant importance and we talk about money. So if you kind of treat it like just how you how you treat your everyday life, I think it'll be it'll be all right. You'll do you'll do better for yourself. Yeah, you'll be better off.

Reshma Vadlamudi 8:10

Yeah. And you did mention about uh IT being uh being an IT professional. So how did the so was it like you woke up one day and you said, okay, I'm not going to do W2, I'm an entrepreneur now. Or how did that transition happen for you?

Early Hustles And Opportunity Spotting

Eshwar 8:27

I guess it's not just one day. I think it's just a burning desire that you have since uh childhood. I think that's where most of people that are entrepreneurs now um would probably would have started the hunger to to do something is is there from the right from the childhood. For me, um, I'm always because I grew up in a very lower middle class family, right? We didn't we didn't and my father was a businessman, but we used to have some liquor stores, but then he he passed away when I was really young, I was like 12. Um, so ever since we just you know we had a house and we had a a portion that we rented out, and whatever the money that we made from the rent is what we lived on. Uh so my mom really, you know, made it work with with that rent. And that's that's our only source of income. Um so when you are growing like that and you have desires to be able to fulfill, um, so what ends up happening is you have a burning desire to be able to do better, right? You always think like, when is my next opportunity come to probably go to a movie with a friend, whatever, right? Because you're always cash trapped. So, in that context, so I think there's that that burning desire is there with me to do something different, uh, to be able to get to where I want to get to. It's not like so have these big dreams and goals, but it's just day-to-day. Like I would like to like to go to a movie today. I like to go, you know, eat at a good restaurant today. So that's just a desire, and then there is like a hunger to be able to achieve that, and then you do that series over and over again, and you have the desire. Um, so I'm no different, and I went to college and I just wanted to do something, and I it was a time when debit cards were a thing. So I found out like back in the day there was no bank accounts and debit cards. Uh, this was 2002, 2003. So I went to the bank or bank manager and say, like, I have a you know, a hostel of students, but probably four, three, three, four hundred people. So I'm able to help them open accounts because most of the times they bring money from their homes because you know they come, they they come from different parts of the parts of India. And then you often, you know, get people, the money is is is is uh you know, um, the people that you know that steal money and whatever. So there's no safe way to store money. So I thought I found that opportunity, and then I said, I walked up to a branch manager and say, like, I'm gonna make you have all these guys open accounts. So how much would you give me for each application? You know, so it was not much of money, but it's not about money, it's about being to try to solve something that I saw was important because that was helping me. Uh, because uh getting money or transferring money was very difficult back in the day in India, and then you had to go and somebody has to give it, or you know, like you know, uh money order which would take which would take a week. Um so so and I felt that was an opportunity and I was able to do you know things like that, you know.

Reshma Vadlamudi 11:23

What grade like was you were you in your B Tech?

Eshwar 11:27

I I was in my master's, I did master's in information technology and management. So during that time, I you know it's like also because my course also had management in it, it's like a combination of you know, MBA and computer science. Okay. So so I was really intrigued by management uh back then, and I wanted to do something, and I used every opportunity that I have to use it for managing projects back in the day. So um then yeah.

Reshma Vadlamudi 11:53

So I went and solved the problem and you opened the bank account.

Eshwar 11:57

It's for differ for different for different people. So so I think um it's been there, the bug is there all the all the time.

Reshma Vadlamudi 12:04

Uh and I when I and uh yes, to finish that story, sir, how much did you make in that transaction? Like how many accounts were you able to open?

Eshwar 12:15

I'll probably say about 70 or 80, and uh I don't think I've gotten paid for that. I was just an agreement, and then I enjoyed the process more than more than um helping people out. And I think I probably probably give me a thousand dollars and this, I mean thousand rupees uh back in the day as an advance. And they said it was very difficult for us to get uh an approval from corporate and all the other stuff, and I just didn't really really did not worry about it.

Reshma Vadlamudi 12:41

But it's a the way you saw things was uh I mean, like with the I don't think anyone would think of it if you don't see it as an opportunity, right? You went out and put yourself out there asking people about this, and why would someone usually care about something like this? Yeah, yeah. Okay, and uh so that's that's the first time you took something like that. That would be like your first step towards entrepreneurial.

Eshwar 13:11

Maybe there are so many numerous things that probably I don't remember, but this is one thing that I distinctly remember because I felt like I made a difference in people's lives.

Reshma Vadlamudi 13:19

Yes.

Eshwar 13:20

Um, and uh, you know, opening um credit debit cards was a thing, thing. And we used to take a bus 40 miles out to actually actually use the debit card to be able to take the money out. Um, so uh, but still it's better than traveling, you know, a couple of days to go to your hometown and get the money.

Reshma Vadlamudi 13:39

Yes.

Moving Fast Across IT Careers

Eshwar 13:39

Or money order, and then you know, my parents have to go to a uh post office and then do a money order, whatever. It probably makes sense for me to just like buy a one-way ticket to get money, right? I mean, that's that's that's those were the days, and uh, you know, I I found that opportunity then at that point, and then I decided to just help people out. Yeah, um, so yeah, I mean that's uh that's one of those things. And I one the moment I finished my graduation, I just started to work. You know, I worked in um different companies in India. I worked uh the last company that I worked in India back in 2020 was Microsoft. I was uh I was leading uh I was leading a team um as a tech lead. Um I used to look at uh the mobile business for Microsoft. Um so yeah, I mean I I I did pretty pretty well and uh you know I kept adapting and I kept changing, you know, I kept going with the next opportunity. Necessarily, uh, you know, within four years or five years, I think I've changed four or five companies. Um yeah, money was good, every every um jump was was about 30 to 50 percent growth. But at the same time, I just found a different opportunity, a different opportunity, and something bigger, something bigger. Um if you if you have that thing on your resume, now you're kind of looked at licked upon as somebody that you know of stability, but I looked at it as being able to learn more because once you learn something, then you get stagnant, right? I don't like stagnation. I just want to be able to move to the next, next uh, you know, change the goalpost and and try to look at something else. Um, so yeah, I mean 2007 is when I'm when I got back, got here to the United States, right? So I just wanted to try something new again. Like, you know, people were saying, like, you had a great opportunity, you are a team lead, and you're gonna be a manager soon. Why would you leave now? I say, like, I don't know. Like, I just feel like something I'll probably get a better opportunity to learn something new in a different place. So I just moved.

Reshma Vadlamudi 15:36

Okay.

Eshwar 15:37

Right. So um, so yeah, I mean, I just kept kept working in different IT companies. I was a consultant, so I'm not tied to anything. I used to work at one company for six months, another company for another six months. So I kind of like that, like that aspect of it. Um, so I've completely changed uh my um my career from Microsoft to EMC, which is storage, which is totally different. So I kind of you know just went for it. Just resetting yourself from zero to one again is is very hard. And I like doing that.

Starting A Staffing Firm And Splitting

Reshma Vadlamudi 16:11

Yeah. Okay. So this is all the W2 part. Then where did the jump happen and where did you start your businesses?

Why Partnerships Break And How To Trust

Eshwar 16:20

Uh so I came here in 2007. Um, so through through a through a through a friend of my um brother-in-law. So he's he's he has an IT consulting staffing business like I have now. Um and he's the one that instrumental was bringing was bringing me in. And uh, you know, he has a very different different worldview of how things are done. And I kind of um was very close to him. Um, and I was in in his company for uh for most of my time while working on W-2. So I saw things that he is doing, and I think I could do could do things differently where I can probably add value. So there's always a burning desire, like, you know, I wish I could do this. He's not doing it right. Um, so then I told him that I was gonna start a company. Uh, and he said, like, okay, so why do you want to start a company on your own? You know, partner with me, do a 50-50 partnership, and then we can do it together. Right. So that's that's how that's how it went about. And then, you know, I started a company with him, uh, doing things that he wouldn't do differently. I said, you know, I'm gonna just completely re reenvision everything that you're doing. I'm gonna do it, do it this way. Um you know, and then and then and then it started off like that. And um, we built a decent sized company in eight months, um, from zero to about 60, 65 people. So the job market was really good back then. Um, it really definitely helped. Um and then I had some differences with him, the way he would pull me back and stuff like that. And then I said, okay, I'm just gonna split. I wanna, I wanna, I wanna just get out of this, this, this, uh, uh, this arrangement, and uh, you know, let me know, let me know what you think. And then he just paid me some money, and then I just walked out, and then I started my own company.

Reshma Vadlamudi 18:12

Okay, so we just came into partnerships. So how important do you think partnerships are in the business?

Eshwar 18:25

So I have a different take on this because I've not had um a lot of um, you know, maybe because of I'm immature at the same time, uh, when I was really young. Um, there's a people dynamic in partnership that is very, very different. Um so so for me it didn't work out. Partnerships never worked out for me. So I kind of stay away from them. Um but I think as I grow older and I probably get see a lot of experiences and then sudden partnerships that were not good, if you can go back and reminisce on those, um, and look at introspect and see like what you could have done differently. And I like sitting back here today, I feel like um, you know, I was immature as well, right?

Reshma Vadlamudi 19:13

I mean, um we all learn as we go.

Eshwar 19:15

Yeah, so so I feel like partnerships are good uh as long as you're able to trust the other person and not think negatively about how things will be affected over a period of time. Everything is good now, but what if you know always uh all the partnerships is like have an end date eventually, right? So putting too much emphasis on the end date and when is that gonna come, and try to, you know, try to um you know be ready for it or whatnot, right? And I think that that that negativity kind of sits with you, and then that is faded, fed off to the other person, even though he doesn't feel like he wants to do anything bad to you. But that negativity that you present, that energy kind of they pick up and they start to do things, right? And then things go south.

Reshma Vadlamudi 20:06

Yes.

Setting Boundaries With Investors

Eshwar 20:06

Um, so but I think partnerships are good. I think there've been an enormous amount of people that grew in that. But I think the most important thing that you need to keep in mind is um to trust the other person and not think about all the negative stuff that you would think, and then think that we both can grow, right? Nobody is like, I want to grow more than him, or you want to just keep those differences aside and look at it as a collective growth approach. Yes, and then trust, put the trust in that person and then and then never think anything negative about that person once you've made that choice and then decision. And I think that feeds off on the other person as well. And I think the partnerships I think can work really well if you have the right attitude. And it's also important who you choose as a partner. It has to have a same wavelength, and it's important for you to also to choose somebody that is also thinks like you. That's that's also important. But for me personally, it's not worked. Um, so I think that sourness kind of makes me always not really be up for a partnership. Um, but again, you know, like I feel like um being being an owner in the, you know, being a stakeholder in the company, just buying a stock is also your partner, right? Um, but you don't question everything details and everything else, and you hope that they they do well if you if you buy a stock, right? Yes. Uh and then you cannot talk to that person and say, like, I've invested the money, what happened, and everything else. And I think if you could just take the same thing and then just you know, just apply in your regular life, I think you'll be you'll be you'll do you'll do much better.

Reshma Vadlamudi 21:43

So maybe with all the knowledge that you have from the partnerships that you had in the past, maybe if you have to set up the boundaries, like so this is this is what is expected, and this is what we can do. And there will be so many unknowns, and we don't know what's going to happen. It's not Like I can I can explain it to you like I I will once once I have the sense of it because in business it's not like it it takes even whoever is in it. Like I'm only telling this from the perspective of real estate, whatever we are doing. Like we do GP and LP structures. It everything has to play out, like the market sometimes will be different. Uh and then it's not like we are doing something bad or anything. So yeah.

Eshwar 22:26

So I guess it's important for you guys, um, based on what my experience is to be able to find the right customer.

Reshma Vadlamudi 22:33

Yes.

Eshwar 22:33

Um, that kind of fits your needs, you probably would have to say no to some people, right? Uh you know, unfortunately, as much as you want the money, you also want the peace of mind.

Reshma Vadlamudi 22:44

Yes.

Eshwar 22:44

And being able to, you know, deliver on the vision that you have and not to deal with the day-to-day cribbing of the people that didn't know what they were investing into.

Reshma Vadlamudi 22:53

Yes.

Eshwar 22:54

So the idea is to, you know, like Warren Buffett, all he does is like one meeting for the whole year, and then just keeps writing letters, right? I mean, just saying, like, don't come to me, I'm not gonna talk to you. If you want to talk to me, I have one day that I'm gonna give you, and you can ask me any question you want. And then rest of the 365, 364 days, so you know, I'm just gonna concentrate on what I do best is to invest on your behalf. And I think for for you guys is also it's important for you to understand those those those those characteristics or uh attributes of of the, you know, just do your due diligence on the on the investors as well, and then take the money from people that that fit your narrative and fit your mindset, right? Um I think uh in a growing business, it's important for you to also get the money. Maybe you make so those those small mistakes in the beginning, but I think it's important for you to have like very stringent um, you know, uh qualifying um, you know, things for you to be able to yes, initially setting those boundaries and then sticking to them.

Reshma Vadlamudi 24:00

Yes. Um, I I totally agree with that.

Eshwar 24:03

Yeah, so just turn money away if you have to. It doesn't matter. Yes, it does, it's not gonna make your life easy uh with having bad investors that are always chirping on your on your um on your back uh than than having investors that knows what you're doing and that they give you enough l time and uh you know uh time for you to be successful, yes, and not ask too many questions. Understand the strategy. I think you need to be able to also help people understand the strategy and then put those um you know expectations right before that you get the money, is to say, like, this is how you communicate, this is what's gonna happen, this is how your role is gonna be. And uh, you know, if you want a GP, you know, like we can co-GP somewhere else, but if you want to be an LP, this is how we want you to be.

Reshma Vadlamudi 24:49

Yes.

Eshwar 24:49

Uh, and this is how we are gonna communicate with you, is extremely important.

Reshma Vadlamudi 24:53

Yes, yes. Tell us more about the IT services that you currently have.

Eshwar 24:59

The same company that I started on my own. I've I think I've uh told the story that I've just split split with him. So I I've got $200,000 as an exit fee at that time. It was a big money back in the day, but uh turns around he sold the company for a million after two months. Uh but again, you know, it's just I I was not really worried about at all, you know, money at all, right? I was like, I don't want to deal with this on a day-to-day basis because it's hampering my productivity. So I want to be get out. I want to get out. He would say, he said, like, you know, okay, this is how it is. You might get like 350 to 400,000. Um, you know, I'm gonna pay you in a year every month this much, whatever. I said, like, okay, I'm gonna give you one price. And then I need it in one payment, right? So I was able to get 450, but I said cut myself short for 200 for a one-time payment because I don't have to deal with that person anymore because you're just it the relationship was seriously severed. So it's important for you to walk away sometimes, just cut your losses short and then get out of the situation. And then we once you have the money, you can do whatever it is that you want to do with it, right? And then uh that moment I used to work as a W2 employer, employment. And then uh and I felt like you know, I had to spend all my time and effort into it. And I was working with Citigroup back in the day in New Jersey, and then I went to my manager and said, like, I'm just resigning because I'm opening a company. And most of most people told you like crazy because you know, most you could you could probably do the same thing while working as well, because I don't like to be hiding and doing stuff on the back, uh, having that that that pressure on you to you know work and at the same time build a business, and especially when the business is really young, it's important for you to have a full and sole dedication to it.