Chief Milestones
Chief Milestones is a business podcast exploring how founders and parents build meaningful companies without sacrificing their health, families, or values.
Through honest conversations with entrepreneurs, investors, parents, and next-generation leaders, the show dives into the real milestones that shape business, wellness, and life.
New episodes release Tuesdays and Fridays.
Chief Milestones
How Long-Term Investing Beats Hustle Culture | Eshwar Prasad | Part 7
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This episode isn't about getting rich fast. It's about what wealth actually requires - and why patience is the constraint most people never solve for.
In Part 7, Eshwar - solo founder and AI builder - answers the questions that don't have clean answers: What did you sacrifice? What would you do differently? Has your greatest financial decision already happened?
His answers are worth sitting with.
We also get into the macro environment - tariffs, the Fed, yield curve management, and why he thinks the short-term pain is strategic, not accidental. And he closes with something simple: fear and doubt are the only two things that kill businesses, portfolios, and people.
In this episode:
- Why Patience Outperforms Everything Else
- What Wealth Actually Is Vs. What Being Rich Is
- Why He Doesn't Take Advice - And What He Uses Instead
- How He Thinks About The Tariff Cycle And What He Sees Coming For Rates
- Where Staffing Still Has Runway In A Gig Economy
- What He'd Do Differently If He Started Over
- How To Stay Productive When The Work Stops Working
- Why Paper Losses Aren't Real Losses
Chief Milestones is a series for operators, founders, and decision-makers navigating real constraints - in business, capital, and the life built around both.
Reach out: ChiefMilestones@gmail.com
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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Patience As The Wealth Multiplier
EshwarPatience. It's the single most important factor. Most people think you need to do things to become wealthy, but you could you could have bought $10,000 Amazon stock in the 1990s, and you probably are a multi-millionaire now. People think like you have to spend time and do this and that. As long as you're patient and you're willing to give yourself, find a secular trend or company or whatever and invest in it for a long period of time, you're going to outperform everything. I can go back, if you ask me, like one thing that I could do something different is probably develop more patience, right? So I think I glossed over that question. But if I think now, I think patience is, I think, is a virtue. I think it's important.
Reshma VadlamudiAnd your loudest why behind the lifestyle and career choices. And if you want, I can give you a little perspective behind what exactly. What is it? So the loudest why behind the lifestyle and career choices.
EshwarLoudest why?
Reshma VadlamudiYes.
EshwarI don't know. Like I just went with the flow. So I just never thought about it. Um, I just, you know, just like a waterfly flowing, I could just I think I think I never really said like I wanted to do this or that, or I've never broke my, you know, pulled my head to do this or that. So whatever life threw at me, I whatever appealed to me, I just somehow took that string and ran with it. So it just didn't, it did, it's not like I made any huge decisions or career intersections that I had to do. Um, but it would it didn't feel like I was taking those risks or anything like that. You know, it's just not uh something that I really thought about to say like this a defining moment or anything like that. So everything, every day is a defining moment, right? Every every action you take is a defining moment.
Stop Taking People Personally
Reshma VadlamudiThe greatest lesson you learn about people i
Eshwaris uh I mean it's like everybody is have their own own way to reason and um you know to live their lives. And I think as uh as collectively they're like um they are really they're really I mean I mean it's a very loaded question. I think um collectively you know we're all connected together, right? Um even though we're separated, I think we are connected by thoughts. Um there's no lessons learned as such, uh, but I think like everybody should be good and everybody should should should uh fighting their own battles and they fight everybody's fighting their own uh mind games, right? Every everybody is fighting their mind battles. Uh and if somebody is uh if somebody is uh you know indifferent to you or somebody misbehaved or somebody did something to you, it's just because they're ignorant, right? And uh they didn't know better. And they did they could not they could they could not figure out their life's purpose yet. And they're just in that stage where where they think that they're doing something, but uh you know, you just sit back and say, like, okay, you know, they will they too will change at some point and not be too critical about people. Yeah. Yeah. Because they have their way they have their own reasons to do and they have they have justifications to to think like they're doing the best thing for themselves. Um but don't get too um affected by it as much.
Reshma VadlamudiYeah, so like you said before, don't take things too personal. Uh people are going through their own shit, uh their own stuff, and uh yeah,
Eshwarthey'll do whatever you think, uh whatever that is that they think that they assume that what's whatever is best for that they think is what they're doing, right? So um, so you can't question anybody, that judgment might be wrong. You can think like that the way they did it is different for the person that is doing it, they feel like that's perfectly normal. So um, so you cannot judge people, right? Um if you don't like something somebody did, uh just realize that that that's what that's the best that they could do at that point for you, right? So it might sound indifferent for you, but of they're pretty rational about what they did, what they're doing to you, or anything like that. It's just how you perceive it. If you if you don't um you know judge anything and uh say like okay, they're bad people, I'm a good person, or whatever, you just you know, you create those boundaries, you create those constraints, and you suffer because of it, or you choose not to get bothered by all those constraints and you just be very very normal and you should you'll be alright.
Reshma VadlamudiGreatest financial decision you ever made.
EshwarI think that's yet to come.
Reshma VadlamudiThat's in the future. Okay, and how are you overcoming it?
EshwarUm I think the the the the the consulting, the staffing side I think has uh is has slowed down a bit. Um but I think uh you know um so I don't know like the the job market and everything else is slot start it will start to slow down it because it probably in the between it's probably gonna be like a gig economy. So you probably will have like short-term projects, you know, um not even six months a year projects, but you probably might get 10, 10-day projects, 20-day projects. That's where the the economy is gonna shift, especially with agents. Um I think there's still some place where we can make some difference in staffing to help companies, you know, get those gig economy workers. I think there's still some um some um scope uh even in staffing business to to identify those areas and start start working on them. But eventually, uh if you are a staffing agency, you need to you need to have agents that you're actually selling to companies, right? Like I'm gonna have I'm gonna give you rent outage, you know, a database agent or a or a or a front-end agent or a back end agent, right? So that's how I think about uh staffing going forward. Yeah, okay.
Reshma VadlamudiUm how can someone you know can start their path to becoming wealthy?
EshwarSomebody becoming wealth, I think is very um uh subjective. So wealth to me might sound different for somebody else. I think I think I was I was listening to somebody um um wealth is all the money that you could have spent, but you did not, you chose to invest. Uh so that's that's wealth. I think it's Morgan House. He has a very good book, Psychology of Money. Uh, if somebody is looking to learn about money, I think that's also one of the books. I think that's probably one of the third books that you can recommend. Uh so he there he talks about uh you know wealth and being rich and being wealthy. So uh being rich is lifestyle, being wealthy is like also lifestyle, but it's it's like the money that you could you could have spent, but you chose not to spend, and you you chose rather chose to invest in it. So so that's that's wealth. So in that context, um I think I think uh everybody becomes everybody should become an investor into into these secular trends. Um don't think investing in stock market is like a day daily or a weekly or a yearly thing. Think of it as like a 10-year deal or deal, and um and and find these trends and invest in in the stock in stocks or crypto or these projects, right? Um and then invest in yourself more than anything else, right?
Reshma VadlamudiI think that's that's the what do you mean by invest in yourself?
EshwarLike learning something new every day, uh just not settling for anything or not being stagnated, stagnated, right? Stagnating. Um get up to date with all the current events, um, get up to date with macroeconomies, understand economy, understand how debt works, understand how uh central banks work, understand macroeconomics, right? And then you will be able to, once you understand money, then you understand uh the entire game, right? It's very as simple as that. Um so everything is uh is leverage, right? Uh whatever we do is leverage. So I think once you understand money and once you understand leverage, half the battle is is won, right? Um so there's not lack of money, there's enough money, people are you know having so much money they don't know what to do with it. Um so all you need to figure out is how do you convince the pay person to be able to give money, write a check to you, in in return of you know what you're promising that person to get back, right? So that's all you need to think about. Uh people always have the mindset of uh, you know, I don't know how to become rich. How you become rich by providing something that that's not out there in the market yet, right? Yeah, yeah.
Reshma VadlamudiAnd what did you have to sacrifice to be where you are today?
EshwarUm what do you have to sacrifice? No, I don't I don't think I've sacrificed anything. I don't look at it like that to sacrifice because if you if you're looking at things like that, you know, I just sacrificed this, sacrificed this uh for this, then you're putting again conditions on yourself, right? I don't think I've sacrificed anything. I think I just um went with the flow and just uh took things as they came and um and uh put put emphasis on learning than uh than earning. And I think uh I think okay. I think I I'm not gonna be I'm I'm not gonna say that I am the best entrepreneur and probably the probably the the richest or famous or whatever. I I just do well for myself and within me I I feel I live a happy life with what I have. I think uh I think that's that's what's important for me, right?
Reshma VadlamudiSo based on your experience today, what's one thing you would do differently if you were to start over?
EshwarNothing. I mean, I don't think there's anything that I could have done that would have changed uh the way it is because every moment of life, my life, I um I did what I what I thought is best for me at that specific time. Um and I have no regrets of what I did, no regrets. I never look back at my failures, appreciate for all the success and um and just move go on, right? I don't I don't intend to go back and change anything, right, in a in a way because I have no regrets with what I did. I think I I think I could from somebody that grew up in India and you know from there to here, I think that's that's that's that's almost as if like it's just uh it's like a six sigma event uh in itself, right? So um um so you just should be I I I am happy with where I am today, and I don't think uh there's anything that I could have done differently.
Reshma VadlamudiFrom what you have seen in business world, what are certain skills that someone should possess to become wealthy?
EshwarPatience. It's the single most important factor. Um most people think you need to do things to become wealthy. Um but you could you could have bought $10,000 Amazon stock in the 1990s, and you probably are a multi-millionaire now. Um people think like you have to spend time and do this and that. As long as you're patient and you're willing to give yourself, find a secular trend or company or whatever, and invest in it for a long period of time, you're going to outperform everything, right? So I think the most important aspect for anything, you don't have to be super rich, right? For you to for you to put in five, ten thousand dollars in 20, you know, two thousands, right? Um and maybe there is a there is the the the landscape of the is shifting in such a way that you know anybody can start their company now. So there's so many opportunities that will present themselves. So the idea is to do research. Now you have enough tools to be able to tell you what it is, and you have develop your own uh frame of mind, develop your own uh knowledge base, you know, read books, review things, listen to podcasts, um and uh and uh you know build your exposure, do things, fail, repeat, right? Um but one thing I think is the most important thing is patience. I think that's where I can go back. If you ask me, like one thing that I could do something different is is probably develop more patience, right? So I think I glossed over that question, but if I think now, I think patience is I think is a virtue. I think it's important. So um so sitting back and doing nothing and letting the investment work for you is not easy. That's why you see a lot of people that are dead and their portfolios that have never touched outperform so much in so many folds, multiple ways, multiple folds that uh that you cannot even imagine, right? So what we end up doing is we um self-impose certain conditions and think like we've gotten 2x our money, okay. Now let's take it out, right? Do something else with it. What are you gonna do with it? Right? If it gives you 2x, it's gonna probably give you 10x, 50x, right? Over pay because compounding is a real thing. So um if you compound your money at 20%, um, you know, 100,000 is enough. In 20 years, you'll be rich than anybody else in the world, right? So so when you know that, so it's important for you to have patience and let your money compound at that specific rate. And which is why I like Bitcoin is because uh because it can compound your money at this time about 60%, even if it cut cut it in half. It compounds at 30%, put a million dollars in there. Uh the amount of wealth that you're gonna have, obviously that million dollars is gonna become 200,000 at some point. Uh that might you might feel like, okay, this that's the end of the world. Again, that money is something that you're not that you set aside for long term, it's not something that the capital that you want to live with, right? I mean, that that you're banking to to spend your day-to-day life. So if you're able to put that money away and see through the 80% drawdown, uh and then just compound at 50-60%, you don't need to do anything. Yeah, if you continue to do that for uh I'm not saying like just put all your money there, but even if you put a little bit of money that you can that's that's that's the that's like a hedge against uh you know the dollar didn't you know being diluted and um and any economy, economical catastrophe that that might happen, might not happen, but that's that's like an insurance uh money that you can that you can have. Uh I think that's why you know, because you don't need leverage to buy Bitcoin. Um and you can just continue to compound it. The only thing you need to develop is is to be able to be okay with 80% drawdown. Um, and uh anybody that bought bought Bitcoin in the last 10 years uh that saw through that 80% or 90% drawdown is probably is probably is doing much much better than anybody else in this in this world. No other investment probably would have given you that kind of return on a consistent basis.
Reshma VadlamudiWhat's the best piece of advice you have ever received?
EshwarUh I don't take any advice from anybody. Um because most of the times advice that I've gotten and then I acted upon turned out the right way. Um so yeah, don't give no advice, don't take no advice from anybody is my my motto.
Reshma VadlamudiOkay.
EshwarDo things, fail, and uh you know, experience becomes your advice.
Reshma VadlamudiDid you ever struggle financially?
EshwarUh again, that's the thing. Like, you know, what do you mean financial struggle financially, right? I mean, I if I feel like I've always had um money to be able to buy food and uh and have a home uh at all points of my life. So I would say no. Let's not if you have money to to survive and eat and then live on a live under a house, however small it may be, uh I wouldn't call anything uh outside of that as a struggle. So then you're basically just um wanting to have more, and it's just probably your expectation of not having more. That's that's the only thing that is uh that is different for you. So I think no. Um the question is uh I don't think so. I don't think I will ever be because I'm confident of being able to earn a basic living regardless of whatever happens in this world.
Reshma VadlamudiIs fear the biggest killer of businesses?
EshwarAbsolutely. That's the only, and like I said, fear and doubt is the only two things that will kill anything and everything that that comes in their way.
Reshma VadlamudiHow do you optimize your productivity throughout the day?
EshwarI don't uh I just do things like I just I feel like I don't want to do anything. I just kind of shut everything down and just yellow watch something or yellow watch podcasts mostly. Um because when I feel like I'm working too hard, I feel like I go through these cycles where things don't work out the way I want to. I think it's important for you to take a step back and take a couple of breaks, even if it means a couple of days, right? Um so that's that's I think it's important for you to just just turn off and then turn that turn it back on. I think if you continue to do the same thing over and over again, I think it's uh it's uh it's it's it gets you into a rabbit hole of uh pleasant things have not happened to me. So so when I I get a feeling that I'm going through that through that phase where uh where whatever I'm doing is becoming anti-productive because even if you work 18 hours, it's not going to be productive work. It's just basically learning, learning, learning. And then you do something, you break something, you fix something, you break something. Um and then sometimes it's good to walk away and not think about it and then come back with a fresh perspective a couple of days later that have always worked better for me.
Reshma VadlamudiAre there any resources that drastically helped you?
Tariffs, Rates, And Planned Volatility
Paper Losses Aren’t Real Losses
EshwarUm I think internet has helped me. Um what are the resources like you know, right now uh Chat GPT and all these AI tools definitely are helping me so much more. Um so I don't have any fear of not knowing anything. So I know I can I I have one one question away to know something totally new, which I which I think I probably wouldn't have known. Now I have time to explore, you know, double slit experiment to to multiverses, to to everything, every crazy idea, thought, or whatever you have, I have I have an ability to go back and and get some perspective of what's out there in the world. So that's powerful. Yeah, I mean I think uh I think they're bad in the short term, but I think like it's again the same analogy that I gave you. Like, you know, if you run up so many subscriptions because you wanted to see that what's the next best thing, right? And you want to just subscribe, subscribe, subscribe, subscribe. Um and what is easier for you to do is to is to just uh call the bank and say that you lost the card and then cut it so everybody else gets gets a notification that they they cannot bill you for that specific month. I think that's essentially what Trump is doing is just creating this. You know, it's very difficult to call each and everybody to the table and discuss um, you know, like, you know, what are you charging? Oh, what are you charging? Hey, yes, this is whatever we charge, and they take a lot of time to come back. But four or five years went by, you don't do nothing. So I think the bold approach is to just increase tariffs and then just have some vaguely bad number, right? I don't think I don't think then they have any idea of what the tariffs are, it's just simply divided by the deficit versus surplus, and then created a percentage, and I said, okay, they're gonna charge half. So it's very uh unorthodox in any very um you know um you know uncanny way to do it. But I think what it ensures is that it will make everybody want to come and talk to him and and discuss. So this could become a crisis management at this point because no country wants to lose uh America as their customer because uh you know we we are the biggest weather that we we the entire trade in the entire world, we we represent 30%. So if we take off Amer America, that's going to be a huge hit on all these economies that depending on depend on uh you know providing these the goods to us. Right. So obviously it's in their best interest to come and discuss and talk. And I think that's uh that's what I see. Like people, a lot of people say that it's it's bad and that he's uh he's intentionally crashing the markets, um, which I agree that they want to um they want to crash the markets. It's in their best interest because the rates are too high for too long. And you know, you've seen it in the real estate that it's just not been such a conducive environment to do anything at this time. So I've invested in a few uh few LP deals in in real estate. Um that it's uh so so it's not conducive to to do anything. The growth has slowed down um drastically, especially in the real estate market. Um and they have uh have about $9 trillion that they have to uh refinance this year. Um so so either they have to pay the bondholders or they have to actually reissue more bonds at a newer rate, right? I know the 10-year is about four years, four, four percent. Uh four years ago, uh, when there's time for us to, because every four years there's a refinancing cycle of the entire national debt. So four years ago it's 2020, the 0%. Now they have to do it 5%, 4%, 4.5%, which is gonna add almost about a trillion dollars just on the interest expense. So uh so that's gonna add to the deficit again, so which is already 36. Now we're gonna add a trillion dollars every 90 days, so it's not an unsustainable path. So um, so they have to somehow bring the rates down. And the for you to bring the rates down, you have to endure the short-term pain, crash the market, uh, force the Fed hand, Fed's hand to decrease the rates so that they can refinance at lower rates. Um and I think uh I think we're going that way. Like, you know, even though this quantitative tightening with the Fed does, I think it's they're ease, they're going to ease it and they're gonna take the rates back to zero. Uh they have to take the rates back to zero, some catastrophic event has to happen. I think uh I think uh you know they are just trying to, you know, you know, the they're trying to do the yield curve management, right? Usually the Fed is responsible to do the yield yield yield curve management. I think Trump has taken it on himself to to instigate fear in the markets, to to have like a short-term downturn, force all the countries to come to the drawing board and do it in a in a in a in an emergency way. It's not like you can sit back and come back and discuss, and we'll do that. So, so I think Liberation Day, I think, is is a is a perfect fit for that. I think they're doing, they know what they're doing. Uh but um but again, you know, it's also also we have been far much far too dependent on cheap labor from China and all these countries. And I think with the advent of AI and robotics, I think uh um it is probably going to be easier for us to bring some of those manufacturing jobs over on board, not with people, but with with with machines and with uh with robots, right? So I think that that reality is settle settling in. So you could probably have um you know some some some some some form of manufacturing to come back to the US. I think that's important for our national security. Uh you can't depend on too much on China or any other country for that matter for for most basic things, which we've been far too we've been dependent on far too much on them. So I think he's playing 4D chess um in in real time. So I think you've got to give it to the guy, and we'll probably have to give some some time to see how this all unfolds. But I'm sure sure it's just a tactic for for him to bring people on board and uh and and try to force the Fed's hands to reduce the rates and refinance the debt at a much lower rate. I think that's the goal. Uh as an investor, um, I feel it is important for you to not to panic in the situation because I think it's gonna be uh it's gonna be a couple of months of uncertainty, and then you know the good the thing with tariffs is that they announced it and they can de-announce it. They'll say like Vietnam um decided to make zero percent on all the imports from the US, you know. Uh so every country will come and you know do something like that. And then they're going to, you know, and then Trump, you know, you know, and because Nike is uh is uh one of the companies that um depends on Vietnam for most of their shoes that are being manufactured in Vietnam. So the moment uh they announced the 60% on Vietnam, you know, Nike stock went down almost 40%. So then yesterday the Vietnam said, okay, well, no, no, we're gonna make everything zero. You also make zero. Then he said, I'm gonna make zero if you make zero. So then the stock took off again on Friday. So it's gonna be like short term blips, right? It's not necessary that when you're losing money, the paper losses are not real losses. Understand that