The Investing Expert: How ANYONE Can Start Investing TODAY To Unlock Financial Freedom
14 May 2025 · 59 min
This content was created by Lewis Howes. This content was uploaded by Lewis Howes. This is a podcast titled "The Investing Expert: How ANYONE Can Start Investing TODAY To Unlock Financial Freedom" recorded on May 14, 2025. It features a conversation between Lewis Howes and Chris Camillo, discussing strategies for investing, financial freedom, and the importance of investing in the stock market. They cover topics such as social arbitrage investing, the challenges of starting a business, and the potential of AI in the investment landscape. The podcast also includes advertisements and insights into how individuals can start investing with small amounts of money.
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If you've ever struggled with money, if you've ever felt like money's been tight or just hard to make, or you're just not sure how to invest your money, or it's just been a confusing mess ever since as long as you can remember. This episode is for you. We have the investing expert on how to create financial peace and abundance during any economic time on the show, Chris Camillo. Chris has an extraordinary ability to spot consumer trends before Wall street does. He's turned 20,000 into 2 million in three years and later transformed 4.5 million into 35 million. During the pandemic, when everyone was freaking out and stressed out, he found opportunities to create financial freedom. And in this episode, Chris reveals his social arbitrage investing strategy that focuses on observing cultural shifts and consumer behavior changes through social media. Chris's approach doesn't require financial expertise. It's about paying attention to the world around you and connecting observations to investment opportunities. He also dives in deep on why women are uniquely positioned to excel at observational investing, but often don't capitalize on their insights. And literally, when we stopped recording and I walked back into the office from our brand new School of Greatness studios here in the valley of Los Angeles, the women on my team said, I am signing up and I'm investing right now. Like this seems so easy to do and it makes so much sense to me now the way he's explaining it. So if you've ever thought about investing or wanted to make more money but you felt like it's stressful, crazy Chris makes it more effortless and he makes it easier to get started. So I think you're really going to love this. And if you're enjoying this episode, make sure to share it with a couple of friends who maybe are trying to break free financially or get to the next level. Make sure to follow the show if this is your first time. Say hi to me on social media Lewishouse and leave us a review of what you enjoyed most about this episode over on Apple or Spotify. Again, I'm so excited about this. I hope you enjoyed this episode with Chris.
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Welcome back everyone to the School of Greatness. Very excited about our guest. We have Chris Camillo in the house. Good to see you man. Appreciate you being here.
Me out.
You just searched something right before we got on here where you said it's your mission to get every human in the world to be an investor.
Yeah, investor class.
Investor class.
Every human, every.
I just saw this stat on CNBC that said just this week the Dow Jones experienced its 11th 1,000 point drop in the Dow's history and four of them happening in just the last month. And also I saw on Twitter this week that the Great Depression has been trending and for that should people with all of the fear or the anxiety or the stress around the stock market, tariffs, the economy, another depression, whatever might be happening, should people be investing now or should they be waiting until later when it feels more safe?
Well, that's all noise. It's always all noise. Okay. Until it's not. And when it becomes something other than noise, we have way bigger problems. Right. That that's the way to think of it. Should you investing now, you should be investing always, I would say especially now.
So even when it's scary or uncertain or it's fluctuating so much.
Yeah. When it gets scary and it starts to fluctuate and you start to hear see people googling the Great Depression. These, this is when you make all your money. Right. So this is a gift. I've been, I've been around a long Time. Like, I, I still feel like a kid investing, yet I can talk about the 87 crash and how I felt during the 87 crash. I was young then, but I remember it vividly in our. I'll never forget how quickly we came back from it. And, you know, same thing with. I was like deep, deep in the dot com bubble crash. Like, that was when I was coming out of college and in the workforce, investing for myself aggressively. And I was. It was like my entire world. And that really was scary. That was like super scary because you.
Probably didn't have a lot of money then. So the things you were investing in, if you're losing it, you're like, what am I doing? I can't afford to lose this.
Well, we, most of us that were young and investing during that time, we lost like 70% of our portfolio.
Okay.
Like 70, 80%. Some of us, a lot of the companies we were invested in just went to zero. Okay. So that was unbelievably scary. Yet those of us that stuck around and kept doing it, I mean, it didn't take long for the market to come whipping back, right? And. And you look back and you go, gosh, I wish I would have went. And even heavier at the time. Same thing in 2008. That was scary, remember? Well, you remember that?
Yeah.
Came back quicker than anyone would have imagined. And wait, this. And nothing phases me anymore like people. You think about the stock market. Well, what is the stock market? The stock market is nothing more than a reflection of all of our work globally. That's it. Our human endeavors. It's the product of our human work. So as long as humanity continues to get smarter and more productive and more efficient, whether it's us or the robots or artificial intelligence that we're creating, doesn't matter how we do it. As long as we continue to create more and create better, the product of that will become more valuable. That's. And our way to participate in that is called the stock market. Like, it's not this crazy, crazy, complex thing. Everyone overthinks it. Wall street has spent, you know, 70, 80 years trying to convince us that it's this big, mysterious thing that only they can understand, that we have to go through them, that we need to be talking to them through these periods. Right? It's complete bs. There's. I don't think there's anything more important in life other than maybe taking care of your family than learning how to invest. Like, it's actually so insane to me. I think it's the most important thing we should be starting with from kindergarten every year for your entire life. A good chunk of it should be focused on reminding you and teaching you how important it is for you to be part of this investor class. And it's just disgusting that it's not.
If you were to simplify for someone in their 20s or 30s who's never invested before on how to invest and what to invest in, what would you share with them? As if you were teaching someone that had no understanding of what investing or the stock market or trading meant and you could simplify that, what would that look like?
Well, so I think a better way to think about it is that something that we all can relate to is the idea of starting a company. Right. We all want to be entrepreneurs. Not all. Most of us in the back of our head. It would be cool to, you know, own your own company, whatever that company is. Right. It never used to be like that. But over the last 20 years now we all kind of think like that. I don't care if you're a celebrity, if you're a homemaker, there's a company out there that you would like to start and own or the idea of being an entrepreneur, well, that's half of my life, right. I'm an entrepreneur. I've been in startups my entire career. I've started a multitude of companies, have sold them. I've had a few big successes in that world and I've had insane number of failures in that world, both as an operator and as an investor in private companies. That is exceptionally hard, that is exceptionally risky. You could try to do that and chances are you will go your entire life and do nothing but fail.
Okay, how many companies have you invested in?
I am invested in about 150 private companies. Private companies.
150 right now.
Private, yes. Meaning each of those companies, I probably have met the founder, have done a massive amount of due diligence on the space and the sector. It just, it's been a huge part of my life, quite honestly.
And how many of those will fail or have failed?
Almost all of them. Probably like 75%, maybe.
Wow. So you do a lot of the research, the analytics. You've got a data company that analyzes all these things in the industries and helps predict certain things. And even with all that work, 75% of your investments are probably going to fail.
Yeah. Because you're investing in an early stage company that has a tremendous amount of. You're investing in an idea and the person. Okay.
I hope that in five to 10 years it'll make money.
Yeah. So that's where it gets risky. That's where you could make a case that maybe you should do that and maybe you should just never do that. Right. I would say for most people, it's insane to go out and start your own company ever. And I've done it. I've done it multiple times.
Why is it insane to start your own company?
Because you're almost definitely going to fail. Like when I said 75%, that's 75% of my portfolio that were deeply vetted and I'm pretty good at doing what I do. Mo. Almost all companies will just fail. If you go to start a company, it's almost definitely you're going to fail.
Even the ones that succeed maybe aren't making a lot of money. It's just getting by. It's breaking even. It's like 5%, you know, it's not making a ton where you're getting rich.
There are a near infinite number of ways for a founder to fail. Okay, now put that aside. Okay. Being an investor, like just generally being an investor, right? Investing in, in stocks, investing in the market. This is what's so wild. You could actually go out and invest in the smartest people in the world. Like, you could just be like, by the way, complete psychopaths. People that will be like, they don't. They're going to like, destroy their family and. Or not have a family. They will have basically no friends. They. They will work 80 hours a week. They're a genius. They're a psychopath. They are going to. They're going to do whatever it takes. They'll steamroll relationships to make their company a success. You can invest in Steve Jobs back in the day, right? You can invest in Jeff Bezos. You can invest. You might hate Zuckerberg, but you can invest in Mark Zuckerberg if you want, right? Sam Altman, Elon Musk, right? Like, whoever it is, like, you don't have to try to be them. You could just literally just throw some money and just ride their life, right? Just like anything they create, any value that they create in this world, you could just get paid for all the stuff that they're doing. Like, we don't ever think like that, but you could do that. Like, we already know who these people are and there are a lot of them out there, right? And do you think that you are that ambitious? Do you think that you're that smart? Are you willing to throw your whole life away just. Just to achieve what they achieve for almost everyone that's probably not a smart or a healthy decision, honestly, but you don't have to.
They're going in. Yeah.
They're doing it for you. So, like, I would. This is like the one thing that I wish someone would have set me aside 30 years ago and said, chris, you're going to spend most of your life torturing yourself as a founder. Which is what happened to me. Okay. Starting companies, growing companies, you're going to have a. You're going to have success this much of the time, and almost all the rest, you're going to fail. Because I've started so many companies, almost all of them have failed.
And it's a good.
It's exhausting. You learn a lot.
You're a smart guy and you're talented. You've got the skills and the resources and, you know, managing people and understanding the markets and what should work.
I have had so many privileges and so many advantages, and it's still so many. Like, I, like my parents were so amazing to have, like, moved us into a neighborhood with the most successful people in the country. And like, I would start businesses in middle school and high school car detailing this, that. Just deeply engaging with these people all the time. Right. And so, yeah, I've had access to some of the smartest, most ambitious people in the world that have helped me all along the way. And still, it's almost impossible. It's almost impossible. And like, now looking back, I joke around that I'm like. I'm like, you know, yes, I'm invested in 150 private companies, and I probably have tried to start that many over the course of my lifetime myself. And if I would have just not done any of that and just focused on investing in other great people, and not that there aren't great people starting companies, but it's really difficult to kind of decipher who. Who is, like, what their weaknesses are when they're just starting off in life.
Yeah. And everyone looks great in the beginning of pitching an idea. And we've got this amazing idea, and it's revolutionary and it's the newest this. And it's going to compete against all these other people.
And.
And here's our projections. In the next three to seven years, it's only going to go up. It's like, everything looks good.
Yeah.
But it's really hard to make money over 5, 7, 10 years in a business and to take on the adversities, the challenges, whether it's tariffs or whatever, it is like, just people problems. It's hard to navigate every adversity every day that comes your way running a business and sustain it over years.
Correct.
It's really challenging.
Meanwhile, you can just pick from the best companies in the world and let.
Them do the work.
Let them do the work. And as soon as they do something that's sauce, you just, you can sell it and get into a different company. Right. There's fully liquid market.
Yeah.
These days stocks trade pretty much 24 hours a day right. Through Robin Hood and stuff. So it's like it is such a magical time to be an investor. Like it. This is the best time in my life to be an investor and especially quite honestly to be investing in public markets. Like I used to say, it was really difficult to identify information asymmetry, which is like my style of investing, like to identify information that other people don't see or don't appreciate. It's never been easier as a retail investor to, to do that and to beat Wall Street. Wall street is weaker than they've ever been. They've had so many layoffs over the past decade. They're they, they're operating off of just a small amount of resources compared to what they used to have. Right. The advantage has swung back to us retail investors. There's just never been a better time. Plus there's just a lot more publicly traded companies now. They can't keep up with all the information flow. We live in a digital world. We live in a social world. What does that mean? It means that.
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We'Re able to detect change. When I say we, I mean like normal people like that are just surfing Instagram and TikTok all day, which is what I Basically do for my investment research. We're able.
Just seeing.
We're able to see the world evolve and change in real time as it's happening without all the noise of Wall Street. And by the way, we live all around the world. We, like, live in the real world. Right. We don't all live in kind of the same place, the Northeast, where we're kind of like all working together in the same buildings, around the same type of noise, with the same media. Cnbc, Wall Street Journal, like just an echo chamber of thoughts. We're actually seeing the world change in real time. And that change, ultimately is what impacts all the companies in the world positively and negatively. So my entire style of investing, which I call social arbitrage, it's like information asymmetry. But what it really is is just observational investing. Okay? It's just literally observing the world, seeing a change, connecting the dots to the companies and sectors that are going to benefit from that change or be harmed by that change. Because you can invest in, you know, in shorting companies if you want to go down that road, placing your bets and beating Wall street, like that's all that it is. And the people that are. Are positioned best to do really well with that type of investing are just normal people that are not, like, financially minded, that are not mathematicians.
Why does it seem so scary, though, for people to invest? Especially when they hear stories like, early in your career, you invested a lot of money, and 70% of it, you lost, you know, pretty quickly with a crash happening.
Yeah. And it all came back pretty quickly.
Yeah. But most people would stop after that and say, oh, this is so painful. I just lost all of this money, which is time, all those hours that I spent to make that money and put it in here. Now it's gone.
Yeah, but that's just a mind trick, right? Like, that's.
How do you overcome.
That's just not. It's just not rational.
So, like, how do you overcome that, though? You spend five years making, you know, saving all your money, you invest it and then it's gone essentially overnight. How do you get over that mental and emotional loss and stick it out and kind of keep going?
You know, it's a great question. And here, and here's what I tell people. You know, any money that you have invested in risk assets, the stock market is a risk asset. You have to mentally, every time you check your account, reduce it by 70%. Really? Yeah, because that's your downside. Realistically. Just realistically, that's your downside. So from the first dollar you put in, you think your account's a hundred dollar account and it's a $30 account. You have to be willing to live with that risk account being 70% less. Okay. Realistically that's probably the lowest it's ever going to go in the worst of all worst case scenarios. Now before you theoretically go lower, anything is possible in this world. We can disappear tomorrow. Okay, so anything is possible, but for the most part your absolute like Great Depression style worst of all worst case scenarios, I like to think of it as down 70%. So bucketing money is one of the most important things for an investor to do. So I always talk about the fact that investors only really have two decisions to make. How much of their money they want to have bucketed in risk assets and how much they want to have bucketed in safety being treasury bills. Right. Or just a Treasury backed cashing account that's paying you 3, 4, 5% a year. Whatever, you make that decision and that decision changes over the course of your life. So when you're young you might have 5 or 10% or maybe even 0% in the safe bucket, maybe you have 20% and when you're old you might have 80 or 90% in that bucket. Right?
Right.
Everyone tries to over complicate wealth management. Everyone thinks oh it's really sophisticated. You go to a wealth manager, they'll hand you like an 80 page report. That's your like personal financial plan. You're like dude, this is so sophisticated, it's all bs. The whole thing is bs. Like it's just a printed out load of crap to make it seem like it's sophisticated and you need all that assistance and help. Like for me I have money that's safe and I have money in risk assets. That's it. And honestly for most people, if you don't want to play the game of trying to beat the market, the money and risk assets could just be in AN S&P 500 ETF Exchange Traded Fund that is basically free to buy and cost you like 110 of 1% internal management fee every year. It's, it's the world's like cheapest way to invest. And you just put money in there every week or every month and you don't think about it. And then you open it up in 40 years and you're super wealthy. Right. Like super wealthy.
Right, right. And just keep it simple, keep it simple.
Like I always tell everyone, like if you are just willing to start investing, there will be a moment in your life more than likely when you wake up one day and you realize that you're making more money from your investment portfolio than you are from your job. I'll never forget the day that happened to me. And I was like, what was that?
Like, how old were you?
So amazing. I was. It was probably 2008, 2009. Ish. Because it was right around the time I wrote my book laughing at Wall street. And I had turned $20,000 into 2 million in three years in my brokerage account. And I was making a lot of money from my job at the time. I was making, like, over $200,000 a year, which back then was a lot of money. I was a sales guy. Right. And that for. It just wasn't enough money for the life I wanted to live with my family and the things that I wanted to achieve in my life for other people. Unlike a very. Like, I have a foundation. Like, I have, like, massive dreams of doing some really big things for. In the philanthropic world. And I was like, I can't live the life I want to live in the neighborhood I want to live it in, do this for my family, and achieve that for other people on $200,000 a year, even if I grow it to 300,000. And I didn't really see a way to grow it to, like, meaningfully higher than that. And I think almost every ordinary person, like, substitute those numbers for other numbers. But every ordinary person is likely in the same boat where they're, like, making this much money and they know that if they really kill it, they can probably get to here, but almost impossible to get above that ceiling. And that's the problem. The problem is what happens is they start thinking, I need to start a business. Okay.
That's the worst thing to do. Yes.
Yes. So. So. So you get in that zone and you think, I got. I got to start a business. I got to start flipping houses. I got to start doing this, doing that. And it's like, oh, I hate it. That that is the roadmap for almost every single person.
Or interesting about that. Sorry to cut you off there. It's interesting, and I understand it because that's what I did early on. I was like, I need to. At first, I was, like, trying to get a job because I was broke on my sister's couch, and I was like, I just need to make some money. I need to get a job. But I had no money, and I really didn't have any expenses living on my sister's couch for a year and a half. Also that I was like, let Me go try to figure out how to make money on my own. And I launched my own thing on the side because I didn't have anything. I didn't have any responsibilities, no bills, no kids, no relationship, nothing. And I learned how to make money on my own without working at a, I guess a career or a job. And then I've just been writing that and figuring out how to make more money. But I don't think it is so time consuming. It's so challenging. There's so many ups and downs that. And it's rare to make a lot of money in the first couple years of running a business. There's so many costs that you don't think about that happen that it's just like, it is hard and it's almost impossible.
It's my. I own businesses, I own restaurants, I like. It is so hard. It's almost impossible.
And it's interesting you say that because that's what a lot of people think about let me go launch a business or a side hustle or something else when all we could do is just let me put some of my money into investments and, and let it make money for me without having to work harder.
Yeah. Yeah, right? Yes.
But it seems so scary of a thing to do for people that have never done it because it's like, I don't know where this is going. Can I get my money out? What if it goes down? Then I've lost my money and then it people retract, right? They're like, I don't want to do that. I'm just going to keep it safe. And so I understand both sides.
This is the biggest life hack. Nothing comes close. Literally nothing comes remotely close to this life hack. Forget about everything else in life and just start investing, period. You're done. And guess what? You don't have to spend any time if you don't want to. You can go do all your hobbies, do all of your stuff, just start aggressively investing and you do not have to sweat the next 30, 40 years trying to restart yourself, your career over and over and over again doing side hustles and, you know, lots of starts and stops and a lot of depression and then a lot. What, what I think I see a lot of, because, you know, my entire life is. Is analyzing social media now for trends, right? That's what I do for my investing. And it's just a crapload of complaining from this generation, which I get it, I get it. If, if you don't know this life hack, I totally understand the frustration you can't make enough money to live the life you want to live. And you see absolutely no, like, light at the end of the tunnel in terms of how you can make it happen. That is a really depressing place to be and it's going to cause you to get out and start complaining.
And you see other people living this rich life or posting like they have a rich life, whether they have it or not, seeming like they're happy with this lifestyle, you know, taking trips and adventures and flying private or whatever it is.
And, and, and, and see, see, that's the issue because everyone keeps talking about the income gap. Like we've heard so much about the income gap the last decade, decade and a half. How are we going to solve the income gap? You're not going to solve the income gap. It's not happening. You can make really small dents in the income gap if you want to, but it's a lost cause. So just stop, okay? Just stuck. Now, the wealth gap, that's a solvable problem. That is 100% a solvable problem.
How do we solve it?
Getting the entire world to invest. Every single person that you're trying to solve the income gap for, just stop and just focus on the wealth gap instead of trying to figure out how to make that person earn three times more than they're earning. It's not going to happen. Make small change, you know, try to help them still to maximize their career. That should all still happen. But teach them how to invest. It's not even teaching. Just convince them. You see, like, I even hate that I just had to say the word teaching. You don't have to learn, you just have to be convinced. You just have to be convinced. And every single person has money to invest, Period. Now, I know people are going to hear me say that and it's going to like, result in a stream of angry comments because they're like, this guy is just completely out of touch. And no, I don't have money to invest. Yes, you do. You don't have money to invest because you're thinking about every dollar as a dollar. But like, this is a big part of what I wrote about in my book a long time ago when I turned 20,000 into 2 million in three years. And I'm not saying that people can do that. That was rare. But absolutely, you could turn every dollar to a hundred dollars over a much longer period of time as an investor, just with compounding. But. And when you realize that, once you believe that, you'll start to think of every dollar is $100, right? And so when you start to think of every dollar in your life, $100, it changes everything. So I don't care who you are, there is a point to which you are not making trade offs. You're not clipping coupons. You might clip $2 coupons, but you're not going to clip a 10 cent coupon. Well, all of a sudden when everything's 100x, you're clipping 10 cent coupons, you're clipping 50 cent coupons. You are, you know, I don't know, you're just doing all kinds of things differently in your life. You know, maybe you're mowing your yard now, maybe you're making your coffee at home instead of going to Starbucks. All the things that weren't quite worth trade trading off are all of a sudden worth making a trade off for. Here's the difference. That money that you save by doing all of those things, right? All goes into your investment account for risk assets, right? And so believe me, when you start thinking of every dollar is a hundred dollars and it will be a hundred dollars at some point, you start finding money in your life. I don't care what it is, I don't care. Literally a, you know, there are people on YouTube, they're actually insane with how to find money, right? Doing all these crazy things and you're like, that is just way too much of a hassle to make an extra $3 or $4. But for $300, I'm doing it. And it is $300. Once you understand that by taking that money and investing it in risk assets over the course of a long period of time, that $3 is $300. Boom. You're making 300 bucks in the morning, you're making 300 bucks at night. Doing this like you're clipping, like you're doing all this stuff.
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It'S like a game that in your mind, oh, how can I turn this $1 into $100? How many $1 can I find and put away into investments today?
It's just, it's a mindset change.
How long does it take in a risk asset to turn $1 into $100?
Listen, it's different. It's different for everyone. It's different for every period of time. I can't predict how the next 30 years is going to go, but I do believe that this is one of the most interesting times to be an investor because of the age of AI that's quickly coming for us. So in one way to think about this is, is our human labor to some extent is a little bit will for some period of time might get devalued, right? If, if we're creating a new industry and that industry is the industry of intelligence, historically that's come from us, right? So now there's an industry of intelligence. And if that industry of intelligence is going to devalue human intelligence, then what do we do as humans? We want to invest in the industry of intelligence and we want to invest in the way that that is going to impact the world positively. So this new industry of intelligence that we call AI and automation and robotics and all the stuff that I'm really into right now, that is going to make our entire world incredibly more productive, right? It's going to bring us efficiencies that we just didn't think were possible in our lifetime. Meaning that enterprise industry is going to become way bigger and way more profitable than it ever has. And we can make money off that by simply owning a piece of it. So you just, you, you asked me earlier, you said, what does investing mean? It just means owning a piece of the world. That's all that it means. You want to own something more than yourself, you need to invest. Okay? So once we start investing, we start owning a piece of that thing that we hate and we like to about, okay? So it's like all of a sudden, you know why guys like me don't complain that much because I own all that stuff. So it's benefiting me, but I actually want everybody to Own it. I hate that I'm making all this money off of industry. I'm making all this money off of technology advancements. And all of these other people are not just because nobody like taught them or convinced them that that was something that they needed to do.
Interesting.
And why did I know it? Because again, I was privileged to grow up in a neighborhood of really wealthy people that were investors and they were smart and like, I had access to all of this. I was really fortunate. Most people were not as fortunate as me. So now I got to spend my entire Life on YouTube trying to spread that word to every person. That's not growing up in a neighborhood with multi million dollar houses. Right. That is growing up in a neighborhood where the culture is not telling you that every single day. Like, hey kid, you gotta invest.
It's more on spending versus investing.
Exactly.
And it's more on how do I look good or how do I get the next thing that's going to make me feel happy and be socially accepted with my peers instead of how can I hopefully live below my means for a while, use that money to invest, and then once I start making more in my investments, the profits there, then I can buy certain things if I want to or just keep reinvesting it.
One thing you just said was wrong. You don't need to live below your means to do it. That's the thing. Like a lot of the things that I was referencing to like make to find money in your life to start investing with. I don't care if it's five dollars, you can open up account right now with like five bucks. A lot of these things, we're not living below your means. It's just kind of doing things like clipping coupons is not living below your means. You know, like, like, it's just doing things a little bit differently to find money in your life that you didn't really care about. But now with the mindset change of accumulating these dollars that are actually going to eventually be worth hopefully $100 each. Hey, you fall short and they're only worth 40 or 50. Even matter? Does it even matter? The bottom line is these very tiny dollars are going to become very big. And you don't have to do anything but literally just do it and throw it in an account.
Yeah.
And just let it compound.
Chris, I know a lot of your audience that you mentioned before we started is men, you know, that are kind of in your system, in your community, on YouTube and Twitter, who are listening to you. There's a lot of women that watch and listen to the school of greatness. And if there's man or woman in their 20s and 30s, let's say, who hasn't gotten into investing yet, who hasn't taken it seriously, what would be the strategy if someone had an extra 100 to $1,000 a month and they said, I'm going to start going all in in this strategy, and whether it's $100 a month, a thousand, eventually more, if they have more, what should they start doing today to set themselves up for their future success?
Yeah. I've been aggressively trying to bring women into the investment world for 20 years, and I'm almost at a point of giving up. I've tried so hard. I told you when I wrote my book, I exclusively market through mommy bloggers because my entire investing methodology is observational investing. And the ironic thing is that women are better positioned, way better positioned than men to excel at this strategy. Like, women are. So women are way deeper into these sectors. Fashion, makeup. Like, okay, like I was just telling you, the world has become digital and social. Right. The best investments come from change. The bigger the change, the bigger the opportunity. Right. How do you detect that change in the world? You detect that change through, you know, reading conversations. What are people thinking? What are they doing? What do they want? What are they buying? Where are they going? Where are they shopping? Where are they eating? Who talks about this stuff more than anyone else? Like, who expresses themselves? Who expresses their feelings about their interest and their. And what they want to own and what they want to do? Women way more than men. Who's listening? Women way more than men. Women actually have all of the insight. Women have, all of the alpha. They have it. They are just not convinced that they can monetize it. Right. I've literally, like, almost like most of my biggest trades over the past 20 years have come from female and youth trends. Really? Yes. Most. Why? Because those are the trades where there is the maximum amount of information asymmetry, where the mostly older, wider, wealthier men who control most of capital markets on Wall street, they are slow to pick up on that change that's happening to, like. I always tell the story about Jeffree Star when he did a YouTube video of the ELF Primer Putty makeup. This is like, I don't know, 10 years ago, ELF was a drugstore brand, the cheapest, junkiest brand of makeup. And he's like, this is just as good as the $60 version. And I went to Walgreens and I just stood there all day and watch moms and kids coming in and they emptied the shelf of Elf cosmetics because of this one product. And that video got like 11 million views on YouTube. And I called the Wall street analyst who covered cosmetics for one of the big three sell side banks. And I asked the person if they had seen the video. I was like, do you see the Jeffree Star video? And they're like, who's Jeffree Star? They don't even watch YouTube. They don't even, they don't even know who these people are. They are so out of touch. And that ended up being a monster. This, this is when Elf was at seven bucks a share, right? It went up to like 160 eventually. Now it's back down to like 50, 60, 70, whatever. Most of my biggest trades, I think probably females knew about that information long before any men generally knew about it.
Why aren't women in general taking action on the information they see socially, digitally and culturally when they see a trend happening? Why do you think there's a fear or hesitation behind not investing in that trend?
I think just the. The field of finance, which is associated with the field of investing. Historically there is a misconception that you need to be a finance head or a math head to do this stuff. Historically, the men in society have always been over that. So it's just a massive misconception. And it's just. I thought we would have come out of it 20 years ago when I first started talking about this, but like it takes a long time for people to break out of it. Like, look at what's happened in the workforce with women, right? Like that happened. Like we have now like massively changed. Like who is in these jobs. Like that's happened, but it hasn't happened yet in the investor class. The investor class is still at least the active investor class. People that are thinking and aggressively pursuing investment accounts is still majority of men, right, that are talking about this, thinking about it, connecting dots. And it's crazy to me, man. It's just, it's absolutely crazy to me because when I like most of my insights come from TikTok comments. So first, I don't know, eight years I've been spending three to four hours a night ingesting TikTok comments. That, that, that is most where I get most of my information from. Before TikTok it was Twitter and Instagram and Facebook, right? Going Facebook going back to the late 2000s.
What's the best trade you made in the last four years on TikTok comments that has paid dividends for you?
I Mean, almost all of my trades these days. I mean, honestly, like most of them come off of tick tock. Like one of them was like the, the big crocs trade. When crocs started coming back in a really big, big way. A massive. That was mostly based on tick Tock comments. Wall street just thought that crocs was a fad that would come and quickly go away. They've always thought that about crocs. And during the pandemic, especially during the pandemic, there was a huge trend for crocs and it was because of two things. One, they did, they killed it with the nursing community and the healthcare community. But then also they were doing all these big celebrity cola collaborations, right? So they did these celebrity collaborations and all of a sudden it kind of like made crocs cool. And it really made crocs cool with like the middle school crowd. And so I was like reading these comments and I was like, dude, like, this is crazy. Like crocs are on fire.
How much was it that the stock at that point?
I don't even, I don't remember exact numbers, but there were so many things that happened during the pandemic, honestly, because the pandemic was one of the biggest changes that we've ever experienced in like consumer behavior of our lifetime. Like all of a sudden the entire world just spent a year in their house, right? So like think about all the change that happened when we all just went home for a year. We started. We cared a lot more about cameras on our computers, Logitech, right? That makes all the cameras. Guess what we bought a lot more of printers. Interesting. Weird, right? Because all of a sudden we're doing our schoolwork at home now we're having to print out something, all kinds of stuff. There were so many things. We started buying camping equipment. One of my biggest trades was Schwinn Bicycle, which was part of a small Canadian publicly traded company. There were lines around every bicycle shop. Remember that?
Interesting. Yeah, Remember that?
The line right around. We bought more bicycles during that six month period than like ever. We bought more campers, camper vans. People were going camping, remember? More ATVs, more boats. I was just. Basically all I was doing was I was on, just reading comments on the Internet, just seeing what people were buying, what they were talking about, right? There was more change than what we've ever experienced in our lifetime. And like people were obviously buying pelotons, right? Shopping at home. Amazon killed it. Shopify killed it. I mean, looking back, it's all obvious stuff, but in the moment. Wall street was really slow, like, really slow to pick up on that stuff. I can't even tell you how many phone calls I did with like, literally like, like people that sold ATVs or like Jet skis. And they're like, we've never experienced anything like this. And I'm like, why is sea do not going up like the company? It's a sea doo, right? Like, that was one of my big trades, really. Just see, like there were a hundred of them. So during the year of the pandemic, I don't know, maybe your audience doesn't know this, but during the year of the pandemic, I turned a four and a half million dollar brokerage account into 35 million. Holy peak. Yeah. So, yeah, just doing that, just literally doing that. Not doing anything sophisticated. Just like, oh my gosh, people are all buying bicycles. That company, seven decks, it went up 7.7x from where it was 7 or 8x. So this is not like trading derivatives or options. Like the actual company itself went up 700% in a very short period of time, as did Peloton, as did so many of these companies that had never experienced that type of growth.
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When do you know when to sell? So when to get in, when to sell and if. What if people are like, it just seems like a lot of time to be watching the market every day, making sure I'm getting the maximum out of my trades.
So I'll summarize for you what I do, but if you want to go in really deep, my book is very personal. It's very old. It's like 15 years old. Now. Jack Schwager wrote a book called Unknown Market Wizards where he spent, I think a decade researching the top retail traders in the world. And I was really fortunate to be one of the five equity traders that trade stocks. To be included in the book, he wrote a 35 page chapter on my methodology. And he really goes in deep to my process. Okay, but at a very high. But it's called Unknown Market Wizards and I don't make any money when he sells books. But, but it's, he, he spent two days interviewing me. It was nuts. And he has interviewed every hedge fund manager in the world pretty much for the last 40 years. And he's seen it all. But if basically what I do is I surface some big change that's happening in the world, it could be a change to consumer behavior, to culture, to technology, politics. It could be a change in the weather. Like one of my big trades back in the day when was a company called Beacon Roofing, Because I would monitor every spring the number of people that were searching the word roof repair on Google. And I literally would go, I'd had 10 years of history and every year it would spike roof repair, right? And one year the hail storms hit populated areas at such a high degree that the word roof repair was tripled. Anything I'd ever seen before. Well, it takes the insurance industry, I think like a full month to print the report of insurance claims that Wall street uses to trade companies like Beacon Roofing that are, they're like the largest roofing supply company in the country. But I had access that information within 24, 48 hours of the big hail storms. And the reason why it's hard to assess hail damage is because you could have really big hail storms. But if they don't hit highly Populated areas, they don't matter. Right. If they hit a highly populated area and destroy a bunch of roofs that does a bunch of roof damage, that increases sales for the company that makes most of the roofing materials in the United States. Beacon Roofing. Wow. And so like, that's just one random example of a trade.
It sounds like legal insider trading. By getting public information that's exactly what it is. And saying, oh, this looks like it might happen in the next couple of weeks or month. Let me get in now.
And there's never been easier time to do it because now I could just do it from my. From my iPhone on my recliner at 11pm at night, searching comments on TikTok or, you know, that's how I get my alpha now. Back in the day, I used to do what Peter lynch used to do in the 80s, which is like literally stroll the mall and look for what stores people were shopping at and talk to people and talk to people that worked at stores and try to assess what was hot, what was not. Like, that was very time consuming. And I still do that a little bit.
Like, yeah, yeah.
But so first you have to surface the change in the world that's happening. And there's change happening every single day. The next, this next year, there are going to be companies that will skyrocket based on their sales going up because of some change that happened. So you have to find the change before the guys on Wall street do. Ladies on Wall street, right. Once you find the change, you have to determine if that change is going to meaningfully impact or what companies that change will meaningfully impact. So this is actually where AI comes in. Pretty cool, right?
You could also ask ChatGPT.
So I was gonna say like you can find some change that's happening in the world and you could go in ChatGPT and say, hey, this is happening. What publicly traded companies are likely to benefit from this? And it will actually tell you. I used to spend like four days figuring that information out of myself, myself. Now you could just ask ChatGPT.
Have you done this yet?
I'm doing it now. Yeah, I'm doing it now and it helps. It's like a tool.
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I hope you enjoyed today's episode and it inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a full rundown of today's episode with all the important links. And if you want weekly exclusive bonus episodes with me personally as well as ad free listening, then make sure to subscribe to our greatness+channel exclusively on Apple Podcasts. Share this with a friend on social media and leave us a review on Apple Podcasts as well. Let me know what you enjoyed about this episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward. And I want to remind you if no one has told you lately that you are loved, you are worthy and you matter and now it's time to go out there and do something great.
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