Loading summary
Sharan Srivatsa
Hey, this is Sharan Srivatsa.
Podcast Host
Welcome back to the Business School podcast.
Sharan Srivatsa
And I got to tell you the truth, when I quote started investing, I.
Podcast Host
Made a bunch of dumb mistakes.
Sharan Srivatsa
Even with the Goldman Sachs background, I'm not joking, I had ego and FOMO.
Podcast Host
And peer pressure kind of run me. So on this podcast, I'm breaking down for you the four mistakes that first time or early investors make and how.
Sharan Srivatsa
You can solve it.
Podcast Host
I break it all down for you step by step, starting right now.
Sharan Srivatsa (Promo Voice)
One thing is for certain, just because it's tried and true doesn't mean it's working right now. So the big question is this, where can you learn what is working right now? The strategies, the tactics, the psychology, and the exact how to, how to grow your business, how to blow up your personal brand and supercharge your personal growth. That is the question and this podcast will give you the answer. My name is Sharan Trivata and welcome to Business School.
Podcast Host
All right, today I'm going to give.
Sharan Srivatsa
You the cheat code. This is what I wish I knew before making, I don't know, a hundred.
Podcast Host
Plus investments that I've made.
Sharan Srivatsa
So if you are kind of earlier.
Podcast Host
In your investing journey, this is probably for you.
Sharan Srivatsa
And I would wager that every single.
Podcast Host
One of us are earlier in our investing journeys, right?
Sharan Srivatsa
If you are not a day to.
Podcast Host
Day professional investor, then this is not.
Sharan Srivatsa
What we do day to day. So I think it's important to know kind of the eliminating the mistakes that first time investors make will already make.
Podcast Host
You a significantly better investor.
Sharan Srivatsa
The reason I'm telling you is this, it's important because most of the times the first few investments that we make shape our not just like what returns we get, but I don't know, it shapes my confidence. If the first deal you invested in totally crushed it, you'd be like, man, I'm really good at this. But if it didn't, if you kind of got crushed, if you didn't work out well, it would take time to almost kind of rebuild the trust and the confidence that you have with yourself and you naturally end up being a little bit more gun shy and that, you know, that kind of takes a long time to get over. And then you miss the power of compounding, you miss power opportunities and you miss a lot of things.
Podcast Host
By the way, if you are unfamiliar.
Sharan Srivatsa
I was a banker on Wall street.
Podcast Host
At Goldman Sachs and Credit Suisse. As you know, I've had a chance.
Sharan Srivatsa
To build two public $2 billion companies, one publicly traded, which makes you understand Wall street even More, I've kind of invested in over 100 plus deals.
Guest or Co-host
After a hundred days, stop counting.
Sharan Srivatsa
And I will tell you this, looking back, I wish that someone had kind of given me a little bit of insight into these things. And I've realized that, you know, when I talk to people and if they can share with me the mistakes that they have made, most of life I have figured out is just doing fewer things wrong, making fewer mistakes, because you don't. It's very hard to, you know, it's very hard to fix a bad diet, right? So if you just didn't have the bad diet in the first place, you would win way more. And so I will tell you the good news is that most kind of.
Podcast Host
Early mistakes are easily avoidable if you.
Sharan Srivatsa
Know what they are. And today I'm going to give you.
Podcast Host
Four of these mistakes.
Sharan Srivatsa
So mistake number one is probably the biggest one, which is, I think it's being embarrassed to kind of show that.
Podcast Host
You don't know what's going on.
Sharan Srivatsa
So being embarrassed to show ignorance in a particular topic. So I will tell you this. When I started investing, I, I would.
Podcast Host
Just pretend like I understood more than I did and just to make myself.
Sharan Srivatsa
Be and look cool. Looking back, clearly this was dumb. And so any conversations that I would have, investors that would pitch me on stuff, I would just nod. I, even though I was confused and lo and behold, what do you think happened? The I made investments, I made commitments.
Guest or Co-host
Without fully understanding a bunch of things.
Sharan Srivatsa
I learned very little in the process.
Guest or Co-host
And the, the, some win, some deals won, some deals lost. But here's what was bad about that. Because of this whole thing, I really think that I was not only stressed about the deal itself, but I lost more money than I should have ever had. So if I actually understood it, I would not have been stressed about the deal. And if I was not stressed about the deal, I would actually understood what investment to make. And if I understood what investment to.
Sharan Srivatsa
Make, I would have lost less money.
Guest or Co-host
Therefore, I should probably not be embarrassed. Now, how do you not be embarrassed? And I think that's very difficult.
Sharan Srivatsa
And so what I decided to do was my kind of advice, number one, on how to not stop being embarrassed. To show ignorance of this stuff is.
Podcast Host
Like, I just tell people, hey, I.
Sharan Srivatsa
Don'T know much about these things. Hey, I'm a really simple guy. Hey, would it be okay if I.
Podcast Host
Asked you a thousand easy questions?
Sharan Srivatsa
Like when I talk to people who are pitching me a deal, I literally use this phrase.
Podcast Host
And I love this phrase, I use it in sales conversations a lot because it reframes the number of questions you're going to ask. And I say, hey, I'm a really simple guy. Is it okay if I ask you at that thousand easy questions? So clearly they know that it's I'm not going to ask a thousand questions, but they know it's going to be a lot. So they don't say, oh my gosh, this guy's going to ask me a lot of questions. And secondarily I say, can I ask you a thousand easy questions? What I've done for myself is given myself permission to ask a bunch of simple questions, and now I force them to be simplistic and help me understand the foundations of these things.
Sharan Srivatsa
So the key in all of this.
Podcast Host
Is like, number one, to have some scripting around asking, hey, I'm a really simple guy. I don't know much about this. I want to support you. Is it okay if I ask you a thousand easy questions? And instead of being like all sophisticated and trying to do chatgpt research to figure out, you know, you figure out what the Sharpe ratio of a deal is and what the efficient frontier is. And you know, because you know what.
Sharan Srivatsa
Cap rate compression is, you don't need to know any of those things.
Podcast Host
Right? And that's why this is important.
Sharan Srivatsa
So the solve in all of this.
Podcast Host
Is to just find a way to invest in groups.
Sharan Srivatsa
If you have a group, if you.
Podcast Host
Have an investor group that you invest in, I would just commit to, you know, kind of doing your first five deals a deals in the investor group.
Sharan Srivatsa
By the way, investor groups will never.
Podcast Host
Force you to do things.
Guest or Co-host
So you can say, hey, I, you.
Sharan Srivatsa
Know, I don't feel comfortable about this.
Podcast Host
Or hey, I'm already com promised my liquidity elsewhere right now.
Guest or Co-host
But they will continue to show you.
Podcast Host
Deals as long as you're involved, as long as you're engaged, and as long as you follow their process, investing in groups is a really good thing.
Guest or Co-host
My favorite way to invest is investing in groups because when someone brings you the deal, they have a sense of responsibility around it. They are in the game with you. You can ask questions off them. You can now sidebar conversations with the group. Different people in the group have different expertise, so they can kind of like jump in and explain things in a much better way. So I'm a big fan of investing in groups to solve this idea. The mistake number one of being embarrassed. And so that's mistake number one.
Podcast Host
Here's mistake number two. I really believe that often we succumb to peer pressure. So succumbing to peer pressure is really like mistake number two.
Sharan Srivatsa
And the, the, the, the reason is most of us will probably find it difficult.
Podcast Host
I'm at least me to say no.
Sharan Srivatsa
When a friend or somebody that you respect invites you to a deal, especially.
Podcast Host
If there's status involved overall, right?
Sharan Srivatsa
So most people, and here's the crazy part, most people worry that, you know, saying no or declining that you want to make this investment will either make.
Podcast Host
You look uninformed or worse, make you.
Sharan Srivatsa
Look poor or that you, you know, you're just gun shy and don't want to participate. They'll think you're a wimp. And by the way, I've been there too. And like, the social pressure can be significantly more intense on stuff like this because it is, is way more intense as a pressure of the type of car you drive or the type of house you live in because everybody knows your home's a low value. The, the way to overcome this is to prepare a script in advance that I'm going to give you that I.
Podcast Host
Use all the time.
Sharan Srivatsa
And so when I don't want to do a deal, here's literally what I say, right? I literally will say this or send.
Guest or Co-host
Them a text message and I say.
Sharan Srivatsa
Hey, Jimmy, I'm going to pass on this one.
Guest or Co-host
I'm already committed to another opportunity for this allocation.
Sharan Srivatsa
Thank you for including me. And I would love to consider a future one with you, right?
Guest or Co-host
So think about that script. So see, Jimmy was giving me the deal. Say, hey, Jimmy, I'm going to pass on this one.
Sharan Srivatsa
So you always lead with the clarity. I'm already committed to another opportunity for this allocation. Two things there.
Guest or Co-host
One, I'm allocating some resources.
Sharan Srivatsa
Two, I'm already committed means I have something else that I'm doing with this money that I'm not going to tell you what it is. Thank you for including me. That means, you know, hey, I appreciate the thought, but I would love to consider doing a future one with you. Not I'd love to do a do one with you. I'd love to consider doing a future one with you. That means, hey, I'm in the game with you, right?
Guest or Co-host
So the, the I will tell you.
Sharan Srivatsa
The crazy part of what I'm sharing with you. There's what other people do instead. The first thing that they do is that they ghost. They'll, they'll literally tell the person who invited them to the deal and will say, hey, let me think about it, and they'll just ghost. And that, that that person now has the pressure to follow back up three or four times. And this is really bad because if you do this, you won't get any show. You won't get shown any deals in the future. And that's why this is important. You don't say, let me think about it. And if you're not interested, just wait around. And if they have to follow up, you've screwed up because of this. You will not get shown deals in the future. And I will tell you, you want to get shown all the deals in the future. I will. You have no idea how many deals I get. I see, I see hundreds of deals a month. When I say, when I say hundreds, I'm not joking. I probably see 10 to 20 deals a week, right?
Guest or Co-host
And every single deal that I get.
Sharan Srivatsa
I respond very clearly to them. And a lot of times it's exactly the script, hey, I'm going to pass on this one. I'm already committed to other opportunity for this allocation. Thank you for including me.
Podcast Host
And I would love to consider future one with you.
Guest or Co-host
You know, and they keep sending me more deals. Now if at some point I would. Because the reason you may say, well, Charon, I don't like the oil and natural gas deals.
Sharan Srivatsa
It's not.
Guest or Co-host
I want to see every deal because it. I see how a deal is presented. I see how a deck is sent to me. Maybe I flip it to someone else that I've been talking to about it. It helps me like relate to industries. It figures out how I can present my information in a. I want to see every single deal. Like I am a deal guy. I want to see every single deal that's presented. If there is a deal that is out there, I need to know about it. And the more deals that I see, the more structures I can see. And the more structures I can see, the better structuring I can do for others. And I learn all my deal structuring looking at other deals. I just don't come up with random deal structuring, right? And so I cross pollinate deal ideas into the deals that I'm working on.
Sharan Srivatsa
Here's the second thing that people do which is really irritating. They make up fake excuses. Please don't do this. The problem here is that everyone knows what a fake excuse is. And what does it do? It makes you lose cred and trust and they just won't show you stuff anymore. So don't make fake excuses. Just tell them the truth. The truth is very freeing. So please don't make up fake excuses. And here's Number three, just to be cool, don't ask a lot of questions to show interest even if you're not interested. If you're not interested, just to be. Just don't ask a lot of questions if you're not interested. If you're interested, ask a lot of questions. If you're not interested, don't ask a lot of questions because now they'll feel like you wasted a lot of their time and you were just kicking the tires even though you were not interested. That's just not fair to the other person. The reason I'm sharing this with you, if you just have the simple script, people will kind of respect you for it and do it over and over again because you want to preserve, I don't know, the relationship in some way while also protecting in this situation your decision making process. So don't let people bully you, don't.
Podcast Host
Let people peer pressure you. Right? So that's, that would be my recommendation.
Sharan Srivatsa
Here's mistake number three, trusting the operator.
Podcast Host
Of the deal blindly.
Sharan Srivatsa
So I will tell you that many kind of early investors assume that the strength of the idea, like whatever idea, the startup idea, the real estate deal.
Guest or Co-host
Idea, determines the outcome. And I will tell you that is not entirely true.
Podcast Host
I've seen that happen in my life multiple times over time.
Guest or Co-host
You will realize it is all about execution. Because when you're investing in something, it is almost passive for you. You're not working on it. What is passive for you needs to be active for someone else. Meaning if I'm going to write a check to somebody, that means I am deploying financial resources, meaning I'm not deploying time, operational capacity, et cetera. If I am deploying financial resources, someone else has to do the work.
Sharan Srivatsa
Who's doing the work here?
Guest or Co-host
Meaning good ideas are sexy, but I get that good ideas can open doors. It can, I don't know, give you more new opportunities, it can make you famous on brand. But the operator, the person who's wielding the, the sword to like, you know, makes or breaks the deal. And I will tell you this, when things go wrong, and I will, I'm telling you right now, when things go wrong and good up, then things almost always go wrong. And I will tell you things always go wrong. You want someone that you trust in the captain's chair, if you will, who has like the, the tenacity, the mental toughness, the grit, the emotional integrity, they know that you will, they are your ambassador in this process. They will, they will do whatever it takes to protect the company and in turn your Investment because they need to realize that the, you know, not quitting is the most heroic thing you can do. By the way, if you don't know that quote, it's an Aquaman quote. Not giving up is the most heroic thing you could do. So because of this, I will tell you, I've made it a standard practice to, like, really bet these operators. As you know, to me, the operator, I want to bet the op. Good people, good intentions, good rationale, good contracts. I want to bet the deal and the person running the deal.
Sharan Srivatsa
And by the way, to do this if the deal is significant for us. And I have not worked with the operator before, I do what I call a mutual. A mutual background check. So let me give you a script that I generally would use to talk to the operator, because I want to see what this operator has done in the past. So I say, hey, Jimmy, we want to make sure that we are good partners to each other. For that, we'd like to offer a mutual background check where you can run a background check on us and call.
Podcast Host
Our references, and we'll do the same with you.
Sharan Srivatsa
What am I doing there? Right? I'm doing a mutual background check. Now, if I say, hey, Jimmy, I want to do a mutual back, a background check on you, he's like, well, you don't trust me? I'm saying, no, I want to be good partners. I want you to do a check on me and check my references, and I want to do a check on you and check your references. Right? And because you want to protect your downside and all this, you have no idea, by the way, I will tell you right now. I had a consulting client who paid me a lot of money for consulting, and then I invested in his company. I lost more money than most people will make in their careers because he was running two sets of books. And then after all of it, my.
Guest or Co-host
Partner was like, did you run a.
Podcast Host
Background check on him?
Sharan Srivatsa
I was like, no. And then when I did, he had, like, he had a felony.
Guest or Co-host
And I was like, okay, so I don't even care that he did. I would have at least asked him.
Sharan Srivatsa
About it, and it would have given me a red flag.
Guest or Co-host
And.
Sharan Srivatsa
And by the way, I'm all about second chances and people being honest. I just wanted to know, and I.
Guest or Co-host
Did not know this.
Podcast Host
It allows you to do better diligence overall.
Guest or Co-host
All right, here's mistake number four is.
Sharan Srivatsa
This big idea of, like, chasing trends, mainly because of fomo. FOMO is a. FOMO is real, by the way.
Guest or Co-host
Fomo, Fear of missing Out.
Sharan Srivatsa
FOMO is real and I feel it all the time.
Podcast Host
And I try really hard to beat.
Sharan Srivatsa
Myself out of it.
Podcast Host
And I will tell you, having done.
Sharan Srivatsa
This for a long time, you know.
Podcast Host
Being a professional investor for 20 plus.
Guest or Co-host
Years, I will tell you hot opportunities are constantly changing.
Sharan Srivatsa
There's always a season for hot opportunities.
Podcast Host
We've gone through the crypto craze, we've gone through real estate markets, we've gone.
Sharan Srivatsa
Through multifamily, we've gone through flip fixes.
Guest or Co-host
And flips, we've gone through Airbnbs, we've gone through, I don't know, forex trading, we've gone through penny stocks, we've gone through, like, it is nonstop. There's always something else. While the, I don't know, while kind of like the details of the deal shift, there's the emotional pull, I don't.
Sharan Srivatsa
Know how else to call it. The FOMO is totally real. And this is where most kind of early investors get swept up in this excitement.
Podcast Host
They want to have that locker room.
Sharan Srivatsa
Conversation that they did this investment deal and then that's the shining penny for them. So I will tell you this. The way to solve that is to tie every investment to the next milestone in your journey. And like, let me explain what I mean. You got to tie every investment that you're doing to the next goal in your journey. I'll give you an example. So let's say, for example, your. If your next goal is to build 12 months of cash reserves.
Podcast Host
I don't know, I'm just making this up. I'm just assuming.
Sharan Srivatsa
Let's say your goal is to have 12 months of cash reserves. Meaning let's say you want, let's say you spend a, you spend $20,000 a month in, in your personal nut. And that's. So that is 12 months times 20,000, that's $240,000. If that is your goal, then your question should be, hey, does this opportunity.
Podcast Host
Help me achieve that?
Sharan Srivatsa
So I take every opportunity that I have and I layer it on the focus of my next upcoming goal or the future upcoming goal. And I just evaluate against now. Sometimes the next goal and the future goals are different, but that's why you have clarity of the future. But this is a really good way to avoid the fomo, right? Number two is like, give you another example. So if your goal is to generate like your first passive income check, you know, where you write a check into an investment and you get the first passive income check. Well, because of that question, you should, if you said, hey, does this. Does, does, does contributing more to your, your SEP IRA or your defined benefit plan get you closer to getting your first passive income check?
Guest or Co-host
The answer is no.
Sharan Srivatsa
Right? So I'm not telling you whether you should put money in retirement accounts or anything like that. That's not my jam. What I am telling you is if the goal is to generate your next passive income check and you don't have that right now, you putting $63,000 in your SEP IRA is a dumb idea.
Guest or Co-host
Because that is not going to generate you your first passive income check, right? Or putting it in Bitcoin is not.
Sharan Srivatsa
A good idea because you're like, man, I got it.
Guest or Co-host
I'm getting it at the right time. Well, it's not achieving the goal.
Sharan Srivatsa
It's not about.
Guest or Co-host
It doesn't matter where Bitcoin ends up in 30 years. It only matters if you hit your next goal so that you can hit the next goal after that, so you can build the confidence in yourself that you can hit more goals. So my, my recommendation would be when you measure opportunities against like your next specific goal, it's way easier to kind of ignore what the FOMO is and what the distraction is, because I have not found any other way. Because otherwise, if the time horizon was unlimited. So think about this for a second.
Sharan Srivatsa
If you had an infinite time horizon, which what that means is you have.
Podcast Host
You know, you're not, you don't really.
Sharan Srivatsa
Need the money tomorrow and you have.
Guest or Co-host
Unlimited capital, then you can take a.
Sharan Srivatsa
Lot of, then you can take a lot that you can make a lot of bets, right? All of us don't have unlimited capital and we don't have an infinite time horizon. Now you may. I, I don't.
Guest or Co-host
So I'm like, all right, so I.
Sharan Srivatsa
Have, I don't have unlimited capital. I, you know, I have, I have access to enough, and I don't have an unlimited time, you know, infinite time horizon. I want, I have a certain goals that I want to hit for myself, my family, my, my company, et cetera. So I'm thinking, all right, so how do I take that goal against the project that I have and evaluate it? If it fits, great. I want to explore it. If it doesn't fit, no, thank you. Pass. Right? That allows me to know that it's a, it's a good idea to have something to diagnose against. Otherwise you don't have a benchmark, you.
Podcast Host
Don'T have a filter.
Sharan Srivatsa
And, and I want to like solve this myth for these, for first time investors or early investors, which is, I honestly thought that just constantly investing in things would make me wealthy. And I want to just remove that thinking for you. Warren Buffett said something amazing, and he said, you know, assume that when you graduate from college or when you're starting a professional career, you had a punch.
Guest or Co-host
Card, and in this punch card, you.
Sharan Srivatsa
Had 10 holes you can punch. Essentially, those were 10 investments that you could potentially make. Ask yourself, every time you make a sizable investment, which putting $1,000 in Bitcoin.
Guest or Co-host
Is not going to change your life.
Sharan Srivatsa
You'Re making yourself feel better about yourself.
Guest or Co-host
If you're going to put a thousand.
Sharan Srivatsa
Dollars in bitcoin and, okay, you put.
Guest or Co-host
A thousand dollars in bitcoin and it went up a hundred X, okay, 100 X over 20 years. Now you have a hundred thousand dollars. Well, in 20 years, that $100,000 is probably worth, you know, time value adjusted, eight $12,000. You could have not done that at all. It doesn't mean anything. It doesn't dramatically change your life. But instead, if you said, hey, I have. I, you know, I have $100,000, and this is a sizable bet for me, and I only had 10 bets that I could make in my life. What bet would I make? Right?
Sharan Srivatsa
And so the reason I say this is it is not about just investing itself. Over time, I will tell you this. I have realized the big difference, that you don't get rich by investing. That's a myth.
Podcast Host
You get wealthy by learning to become a good investor. There's a big difference.
Sharan Srivatsa
You don't get good by just investing.
Podcast Host
You want to become a good investor.
Sharan Srivatsa
And that is a skill. And you can only learn that skill slowly through mistakes.
Podcast Host
Or you can do this by just avoiding the mistakes that people like me have made so that you don't have to make them. So the four mistakes that you should avoid are, number one, stop being embarrassed to show ignorance. Essentially, if you invest in groups, it's significantly better. Number two, don't succumb to any peer pressure. And if someone's going to peer pressure into something, have a script, say, hey, I'm going to pass on this one. I'm already committed to another opportunity for this allocation.
Sharan Srivatsa
Thank you for including me.
Podcast Host
I would love to consider one with you for the future.
Sharan Srivatsa
Right.
Podcast Host
Number three is don't trust the operator blindly. Do what we do, which is, you know, you run a mutual. You offer to run a mutual background check. And number four, do not chase deals out of fomo. And the main way to think about that is you want to have every investment be a solution to the next milestone or the next goal that you have and that always makes sure that you're making progress towards that.
Sharan Srivatsa
Honestly, I will tell you these are.
Podcast Host
Probably what I wish I knew before making what a hundred plus investments. So these are the four mistakes first time investors make and hopefully how to avoid them. If you like this hey, can you.
Sharan Srivatsa
Do me a favor?
Podcast Host
Can you screenshot this, post it on social and tag me. That way I can make more like this for you. I'll know that you like this, otherwise I have no idea. So do me a favor, share this with somebody if you think it'll be helpful. But most importantly, screenshot this and tag me. That way I can make more like this for you.
Sharan Srivatsa (Promo Voice)
Hey this is Charon. I have an awesome free gift for you just for listening to the podcast. As you may know, I've got a chance to build build 2 billion dollar companies the hard way.
Sharan Srivatsa
So if you like this episode you.
Sharan Srivatsa (Promo Voice)
Will love getting the exact playbooks from those wins. It's on my sub stack called My Next Billion. It has the exact frameworks I wish someone had given me when I was.
Podcast Host
Figuring it all out.
Sharan Srivatsa (Promo Voice)
Now you get the real lessons from.
Podcast Host
The trenches as I go for a.
Sharan Srivatsa (Promo Voice)
Three peat and build the next billion. So everything's free atmynextbillion.com. please check it out mynextbillion.com.
Podcast: Business School with Sharran Srivatsaa
Host: Sharran Srivatsaa
Date: November 11, 2025
Sharran Srivatsaa delivers a tactical, straight-talking masterclass on the four most common mistakes that first-time (or early) investors make. Drawing from his own investing journey—from Wall Street banker to serial founder and prolific deal maker—Sharran breaks down not only what goes wrong, but exactly how to avoid the common pitfalls that derail new investors. Using real stories, scripts, and simple frameworks, this episode is a must-listen (or read) for anyone starting to put capital to work.
| Mistake | Solution / Fix | |----------------------------------------------|-------------------------------------------------| | 1. Embarrassed to show ignorance | Ask simple questions, invest with a group, script for transparency | | 2. Succumbing to peer pressure | Use a direct script to decline, respond to all offers, never ghost | | 3. Trusting operator blindly | Always vet operators, propose a mutual background check | | 4. Chasing trends and FOMO | Tie investments to specific goals, ignore hype |
Sharran leaves listeners with a powerful message: focus not on investing for its own sake, but on deliberately becoming a better investor by learning and avoiding common traps. The difference, he stresses, isn’t in doing more deals, but in doing fewer things wrong.
Apply these frameworks to start your journey with intention, clarity, and confidence—and skip a decade of painful mistakes.