How to Make Dumb Money

Chris Camillo is not a stockbroker, financial analyst, or hedge fund manager. Yet he successfully grew a $20k brokerage account into $20 million by observing social trends, cultural shifts and identifying game-changing information hidden in everyday life. Thus, creating an entirely new class of investment analysis termed Social Arbitrage. Watching TV, reading tabloids, eating out, shopping, and keeping his eyes and ears open on social media. The day-to-day goings-on of the average Joe. Except the average Joe isn’t scoping out the local 7/11 at 13-years-old, sussing out the Snapple shortage in the refrigerated section. Which is exactly how Camillo made his first big move. 

In 2015, he co-founded the social intelligence platform TickerTags, leveraging data to detect early trends from social media conversations. The company was not only credited for accurately predicting 2016’s Brexit vote, but was embraced by Wall Street’s largest banks and hedge funds. As YouTube’s first lifestyle investing vlogger, he created Dumb Money—consisting of Camillo and friends investing in businesses: early-stage startups, celebrity co-founded brands, publicly traded equities, real estate, and local restaurant or bars. The series documents their experience and turns it into a masterclass on investing for the everyday man.

Now touted as one of the greatest independent traders of all time, and on a mission to help close the wealth gap by bringing the world onto the investing class, Camillo walks us through the steps of how any one of us can nail “observational investing,” taking the power back from social media, seeing what Wall Street cannot, and learning to stop thinking everyone else knows more than we do.

LEO: So, talk to me like I’m a total dummy because I don’t really know much about finances, but I think what you’re doing is fascinating.

CHRIS: You’re talking to the right person. My YouTube channel is called Dumb Money because that’s what Wall Street calls people like us. They call us “Dumb Money” ’cause we’re not technically pedigreed. We don’t come from the right financial background. We don’t have an MBA in business. We don’t work at Goldman Sachs. That’s okay. That’s my entire life, is trying to tell people that you actually have an inherent advantage being off Wall Street, being “Dumb Money”. Most people don’t understand that.

I got started as a really young kid. I was always about money, so I was a little bit of a hustler. I would do garage saling. Thrifting and all this stuff back in the late ’80s, early ’90s. I was a really awkward teenager. I would spend hours researching garage sales, trying to identify at least one sale every morning that I could be the first person at, that would be the most likely to have mispriced merchandise. And my strategy was that most estate sales were managed by women—generally, older women—and they were really, really good at pricing silver and pricing antiques and all this stuff, but they were really bad at pricing items that were focused on males. So anything like train sets or old fans or watches, baseball cards. Anything that was male-oriented had a higher probability being mispriced.

That’s pretty funny.

Yes. It was like arbitrage. I was arbitraging information that I had that people that were pricing the merchandise didn’t have. And one day, I walked into a 7-Eleven. Every morning, I’d start my morning off at 7-Eleven here in Dallas and I would get like a lemon-flavored Snapple iced tea. One morning, I walked in the store, I must have been 13 years old, they didn’t have any lemon-flavored Snapple iced tea. And where they used to have two full refrigerators full of Snapple, which was the hot drink back then, they only had half of one refrigerator of Snapple. The clerk at the store told me that there was all this new competition, that Pepsi was coming in, Arizona iced tea was coming in, and that they would no longer have as much inventory available for Snapple.

My older brother was a stock broker at that time and I said, “Can I make money off this insight that I just came across this morning?” And he taught me how to, essentially, short Snapple stock—which was one of the hottest stocks in the world at that time—and I did. And sure enough, that was the first time in the company’s history when they reported missed earnings. Retailers like 7-Eleven were pushing the inventory back on Snapple because they didn’t have as much shelf space allocated to them. And that’s when I realized that, even as a young kid, I was able to see something that no one else saw—and like, how many people who worked on Wall Street could have seen the same thing in their local convenience store, but they just went on with their day? So that’s what I call “observational investing.”

That is fascinating.

It all started with that one bottle of Snapple and, quite honestly, I didn’t really become an active investor for many, many years after that because I went off to high school and college and had other interests; I just wasn’t really doing anything meaningful, quite honestly, for many, many years. But at a certain point, when I was back in the real world and I had a job, and I wasn’t making as much money as I thought I would like to make, I said, “You know what, I’m gonna get back into investing.” And I ultimately got back doing just that, observational investing.

I started with roughly $20,000 in 2007 in my seeds. Now in 2021, and as crazy as it sounds, simply by identifying change quicker than others, by essentially looking for a change in consumer behavior or change in culture, change in shopping preferences, change in technology—by discovering that change a little bit early and then connecting that change to investable opportunities in the stock market. It’s been 15 years and I’ve generated about $60 million off that $20,000, quite honestly, just looking for change early.

And what’s really ironic about that is that, as a kid my advantage was looking for male-oriented items. And now, so much of my success the last 10 to 15 years as this amateur investor has been focused on female trends and youth trends.

Essentially, anything that would be off-radar for your average financial professional—who generally lives in the Northeast and big cities, is middle aged, generally tends to be more white, generally tends to be more male. Most of the opportunities that I’ve come across now have been female, and have been youth or culture-oriented; and just being able to identify those trends quicker than Wall Street and taking advantage of them in the stock market.

Chris Camillo on LEO edit.
Courtesy of Chris Camillo

Can you give us a couple of examples you’ve done really well with?

Do you know, Jeffree Star, for example? You probably know who that is.

Yes. The beauty influencer.

Yea the big beauty influencer. Really big on YouTube, 10 or 15 million followers. Jeffree Star is not the type of person that Wall Street would follow on YouTube [laughs].

Right, yea.

He’s considered to be maybe one of the most influential people in skin care. Jeffree Star came out a couple of years ago, and out of nowhere, did a review for a drug store make-up brand, Elf Cosmetics—which he generally didn’t do a lot of. He essentially came out and said, “Hey, this Elf Putty Primer is one of the best I’ve ever used and it costs $6 at Walgreens and CVS, and it’s as good as the ones that I love that are $60.” And that was an absolute game changer. I’d just happened to see that YouTube video right when it aired.

I thought, “Wow, this is just a game changer.” Elf cosmetics was a pretty small publicly traded company. I then went out and interviewed about a dozen Walgreens locations and Target locations, and I would sit there sometimes for hours at a time and just watch people and kids come into the store and buy everything Elf off the shelf [laughs]. And I would interview them, and every single one of them was like, “I just saw the Jeffree Star video on YouTube, I have to have this.” I would speak to moms that were coming in. Within a few days, it was all sold out, literally all sold out. Couldn’t get any Elf stuff anywhere. And so obviously, I made a major investment in Elf Cosmetics and the stock more or less doubled over the course of a few months.

“It’s all about identifying change just a little bit early, and it could be in any facet of life.”

It’s painful to hear for those of us who did not make those investments.

You know what’s so funny is… So who had the ability to see what I saw? At least 10 million people. Now, how many of those 10 million people that follow Jeffree Star connected the dots and said, “Wow, that’s a game changer. He’s never done this before with a drug store brand.” How many people posed that question to themselves and then went out to research to see, “Well, is this a publicly traded company? Wow, yes, it is. Maybe I should invest in them because these old guys on Wall Street probably aren’t looking at Jeffree Star YouTube videos and they might not know about this for a month or two,” which is exactly what happened. And once they found out that there were major sell-outs happening nationally because of this video, of course, Wall Street caught on, and then the stock starts going up. So it’s all about identifying change just a little bit early, and it could be in any facet of life.

Another one I love so much is, I don’t know if you recall, a few years ago now, when DIY slime became a really big trend with kids and moms—like making slime at home. Do you remember that?

No, that was was before my time as a mom.

Okay, okay. So this is a huge trend a few years ago, huge, huge, huge. Look, I don’t have multiple monitors, I don’t even have an office. Everything I do is on my iPhone, literally 100%. When I get up in the morning, I’m just on my iPhone in bed for a few hours, just searching social media. I’m searching Instagram, TikTok, Twitter. I’m searching for various keywords. What I’m looking for are things that are trending. I’m looking for anomalies. That’s where things happen first, that’s the first source of change is being able to identify what people are talking about. And I noticed very early on that this whole trend of making slime at home was becoming a huge deal, and so I researched the ingredients of what it took to make slime and the number one ingredient was Elmer’s white glue.

Funny enough, within a matter of weeks, Elmer’s white glue was selling out at every store in the country. Micheal’s sold out, Target sold out. And so, alright, who makes Elmer’s white glue? Who owns that? There was a company called Newell Brands; they are a fairly big-sized publicly traded company, and Elmer’s glue is a relatively small division of theirs. Well, sure enough, Elmer’s glue sales for Newell Brands just about doubled over the course of a few months. It was unlike anything they had ever seen in the history of Elmer’s glue. So that’s another example. I invested in Newell Brands, and it ended up being a really big return for me.

So literally anything, it could be Kylie Jenner talking for the first time about the fact that she used lip filler. Great, well who makes lip filler? And you start researching, and you find the publicly traded companies that actually are behind lip filler—the big one at the time was Allergan. So I made an investment in Allergan, because once Kylie came out and said, “Hey, I use lip filler”—what happened? It kind of initiated like a multi-year mega trend of women around the world getting lip filler. Well, who was the biggest beneficiary in that? Allergan. So that, again, is yet another instance. We’re identifying something big, identifying change, identifying, for lack of better words—a trend, a cultural trend, a consumer trend.

And then walking it back to the source. You’re not investing in slime, you’re investing in the thing that makes this slime.

Any time you see something that’s a big change, the first thing you do is you ask yourself, “Okay, are there any companies that would either benefit from this or be harmed by this?” And you just have to connect the dots. It’s something that anybody could do. You don’t have to be a financial analyst to connect dots. The next question you have to ask yourself is, “Is this change really meaningful? Could it really move the needle for this company? Is it like 1% of what the company does, or is it 50% of what the company does?” And if you come to a determination that that change that you’ve identified early is truly meaningful to that company, the next question you have to ask yourself is, “Does everybody already know about this yet?”

Meaning, does Wall Street know about this? Are there already articles in The Wall Street Journal about how this is going to impact this company? Are people on investing message boards already talking about this? Are analysts on Wall Street already talking about this? Has the company already come out and given a press release? And if you can’t find any instances where the investing world has already discovered what you discovered, then there’s a pretty good chance that you can—what we call in the investment world—arbitrage that information that you came across.

And so you have to first determine, is it meaningful? Will it move the needle for the company? And then you have to determine, do a lot of people already know about this? And then the last question you have to ask yourself is, are there other things happening at this company that are more important than the thing I just found? And if there aren’t, that’s everything, that’s literally my entire process, and I’ve gone through that process time and time again over the past 15 years.

So why women’s and youth-geared products in particular?

As men, a lot of us, most of us have a significant other in our lives, and a lot of times that person is a woman. It could be a girlfriend, it could be a wife. You might have children. We also have co-workers, and even if we’re a man, we have so much exposure to women in our lives. And almost because we’re a little bit far removed from some of the topics that women speak about, we’re not as engaged emotionally in that topic. We can be observant about that topic in a way that sometimes is even tougher for women to be observant about. And that’s what I taught myself to be is just observing other people speaking about this stuff.

I’ll tell you about a company I’m investing in right now that I’m really excited about. It’s not really male or female. There’s been a huge shift the last few years from beer to hard seltzer. Huge, huge, huge. And one of the companies that has really been late to shift from beer to hard seltzer is Molson Coors. Molson Coors is a publicly traded company. They make Miller Lite, Coors, and Coors Lite. And they haven’t done very well the last few years; they’ve been a little bit behind the curve. But they have two new products, products where they are the exclusive distributor, and that I think are game changers, and I think the market really just doesn’t understand how big of a deal they are. One, is an energy drink called ZOA Energy. And the reason why it’s a big deal is because the Rock is behind it. It’s the Rock energy drink.

The Rock is actually my client so I’m definitely familiar with it.

Oh, I didn’t know that. Okay, so Dwayne Johnson, people don’t really understand that he’s one of the most… When we talk about movies, we have four quadrant movies: movies that appeal to old people, young people, females and males. Dwayne Johnson is a four-quadrant influencer. Literally, everybody loves him, and Wall Street doesn’t quite grasp that. They don’t understand how big of a deal that is. Energy drinks are actually one of the largest sectors in the world of beverage. If you go to Costco, you’ll see they have two aisles dedicated to nothing but energy drinks.

And so the Rock has this new energy drink called ZOA, as you know, and Molson Coors is the exclusive distributor in North America for ZOA Energy. They also have a small piece of equity in the company. This is a really big deal. I think it’s so big, and Wall Street completely just doesn’t understand it.

Why do you think that is?

So that’s one piece of it. The other piece is what I call “geographic bias.” A lot of times, based on Wall Street being primarily in the Northeast, they miss things that come up from the South, or come from the West. A good example of that is when the iPhone first came out, no one in New York used the iPhone because it was on AT&T, and AT&T had a really bad data plan in Manhattan because, at the time, the data structure that AT&T was on didn’t do a good job going through buildings. So it was almost impossible to use AT&T. Therefore, it was almost impossible to have an iPhone the first year it came out. Wall Street didn’t really see how big of a deal the iPhone was because they were biased. They weren’t really seeing as many of them in people’s hands than we were in the rest of the country, and how passionate people were about it.

“A lot of times, based on Wall Street being primarily in the Northeast, they miss things that come up from the South, or come from the West… when the iPhone first came out, no one in New York used the iPhone because it was on AT&T, and AT&T had a really bad data plan in Manhattan…”

Likewise, there’s a brand that came out of Mexico, it was like a big Texas brand for years called Topo Chico. I don’t know if you’re familiar with Topo Chico or not.

I’ve seen it around.

Okay, so Topo Chico, I’m going to say, might just be a brand that people are more passionate about than any other beverage brand I’ve ever seen in my life. I own a restaurant here in Dallas, and it’s just stunning the affinity that people have towards this brand. They love their Topo Chico. Well, Molson Coors just got the exclusive to be the North American distributor for Topo Chico Hard Seltzer and Topo Chico Ranch Water, which are two alcoholic drinks that Topo Chico just released literally in the last two weeks. This is a really big deal. Coke actually owns Topo Chico. They’ve never made an alcoholic drink ever. This is the first alcoholic drink that Coke has come out with, and they chose Molson Coors to be their manufacturer and their distributor for this product.

I think this has all the ingredients to be one of the top selling hard seltzer brands to go head-to-head with brands like White Claw and Truly that were the early players in the space. And again, this is something that Wall Street doesn’t really see because Topo Chico is a Southern brand. They migrated up from Mexico. They’re the biggest thing ever in Texas, as we’ve seen. Eventually they’ll be really big in the Northeast and the rest of the country, but it just… it takes some time to get there. That’s a geographic bias that Wall Street has, but as an ordinary person just living in Texas, it’s something that I see really clearly.

I guess my question then is, how are you able to give these tips away? Is it because you’ve already made the investment, so at this point, it doesn’t matter?

No, it doesn’t matter. And also, quite honestly, I’m super transparent about everything I do. I’ve been super fortunate over the last 15 years or so. For the most part, everything I do right now is inside of my charitable foundation. I have a foundation for pediatric causes, which I’m super passionate about. For the most part, all the investing I do going forward and all the gains I make goes towards my foundation.

But even a higher priority than that is I have a mission to close the wealth gap, the global wealth gap. And I think people spend so much time focused on the income gap, which is a really difficult problem to solve, but the wealth gap is an easier problem to solve. The best way for us to solve the wealth gap is to onboard the entire world into the investor class. I’m on a life mission to literally onboard every person on earth, no matter what your age, no matter what your background, no matter what your education level, I want you in the investor class. And that’s why I started doing YouTube a year and a half ago, and it’s just been this wild ride.

We have people in 60 countries watching our show and every investment I find, I openly talk about on YouTube. I have a community now of a few hundred thousand people between our YouTube channels and my Discord community, and we help each other. We’re “Dumb Money” people, or “Dummies.” And quite honestly, it’s astonishing, there are so many people in our community that have just literally made millions and millions of dollars over the past year. And they’re just regular people, with regular jobs, but we’re collaborating together. We’re helping each other. We’re researching. We help discover change, like I was saying. We discover investment opportunities together.

Ok, so take me for example. I’m a “Dummy.” I’ve never invested in my life. Let’s say, though, I have some inside scoop. I’m excited about it. I do the research. I do all the steps that you’ve said, and now I’m like, “Okay, I feel good about this.” Then what? I don’t even know where to begin making an investment.

That’s the best thing. That’s the best part of living in 2021 because, yes, six years ago, it would have been a little bit intimidating opening up a brokerage account, figuring out how to actually buy a stock. You would need maybe someone to hold your hand and walk you through it, but now… Oh my gosh, we have these apps like Robinhood. When I say it’s and easy and fun, I mean, it might be the easiest thing you’ll ever do on your phone is opening up a Robinhood account. You could open one up in five minutes, download the app, open it up. Public is another example of a super easy app.

Literally within five minutes, they’ll connect to your bank account. You can move some money in it, and you just click a stock and say how much you wanna buy. Here’s the best part, they have what’s called fractional shares, so it doesn’t even matter what the share price is. If you wanna buy $6 of the stock, they’ll buy you $6 of the stock, even if the stock’s trading at $100, they’ll buy you 6% of one share. And it’s just the easiest, most fun thing in the world to do. 15 million people have done this in the last year. We have more regular, Dumb Money people that are opening up brokerage accounts just in the last year than we’ve had, in like, maybe the last half decade or more [laughs]. It’s an amazing time to do this.

Ok so let’s say I don’t speak math or percentages. But let’s say I’m excited about this product, I wanna invest. How do I know how much?

You know what, the best thing about this is, you don’t have to be perfect, when you’re starting off, it doesn’t really matter. For most people, I would say don’t overthink it. Start really small, put a little bit of money, whatever you’re comfortable with, and just watch it. Watch what happens, watch it grow, start to understand why the stocks go up, why they go down. If you see a stock and all of a sudden… Well, I had $100 in the stock, and it just went up to $150… Why? What happened? Read the story that came out that day on that stock.
And understand what the news was, and is that news that you knew about before, did your thesis, work?

I talk about this like you’re a private investigator or you’re a scientist, like you have a thesis that, “Hey, I think this drink is gonna be really popular, more popular than other people think. I think it’s going to benefit the company, so I’m gonna buy into the company.” It doesn’t matter how much of the company you buy. Have it be really small at first, just so you could start experimenting because, quite honestly, the best way to learn is to just do it. It doesn’t matter if you’re doing it with $10 or $1000 or a million dollars. Just start doing it. Whatever it takes to make you comfortable. So, if investing with $50 is comfortable for you, so you don’t have to worry about if you make a mistake, then start with $50. For someone else, it might be $5000. It really doesn’t matter all that much.

And slowly you’ll start picking up on little things here and there that you might wanna know about as an investor. People like myself and Dumb Money TV. You have guys like Graham Stephan, Meet Kevin—there’s a whole bunch of us out there on YouTube now, and our entire lives are just trying to bring this world to ordinary people. That’s it. . We have very few people in my community that are professional investors, most are just regular people that just started investing. And they’re realizing that they have an edge.

I think that’s the big secret. The big secret is, not only are you not at a disadvantage, but you’re actually at a huge advantage by being more deeply connected to the real world than a professional investor who is just consumed by fundamentals, and numbers, [laughs] and what I would call nonsense noise. Wall Street now understands that all the action is understanding the consumer. So who better to understand the consumer than the consumers themselves?

Right yeah, absolutely.

My last company was a data company called TickerTags that actually mined data across Twitter and Reddit for Wall Street, some of the largest hedge funds and quant funds in the world and investment banks in the world. And I sold that company to Jefferies Bank. I was like the social media guy for Wall Street. So, I actually trained a lot of the world’s largest hedge funds and investment banks and analysts on how to extract information from Instagram, Twitter, Reddit. How to understand consumer change and behavioral change, and then connect that to investable opportunities. So they are using data software to try to get into our head, to figure out what we’re going to buy next. Where we’re going to go next. They’re one step removed from actually living life.

“People spend so much time focused on the income gap, which is a really difficult problem to solve, but the wealth gap is an easier problem to solve. And the best way for us to solve the wealth gap is to onboard the entire world into the investor class.”

I know, we always think “But they’re so much smarter than us, how can we compete with teams of people on Wall Street?” I promise you, I’ve seen it first hand, not just through my own portfolio, but through numerous people in my life and my world, my friends. Again, all ordinary people at regular jobs. Through tens of thousands to hundreds of thousands of people in my community. They are killing it. [laughter] They’re all killing it, and it’s very addictive.

This is all I do, every single night. I spend about four hours on Instagram, TikTok and Twitter, on my phone, and all I’m doing is looking for trends. Seeking out any anomaly, something that’s different about what people are doing in terms of consumer behavior—what’s hot, what’s not hot? How is culture shifting? How is that shifting culture going to impact this sector versus that company?

95% of what I do doesn’t result in me actually making a trade. And that’s something that’s really important ’cause people think, “I don’t have time for this.” I’ve only made maybe two to three really big trades a year for the past 15 years, so that’s once every four months that I find something that’s interesting. That I make a big trade on. It’s not day trading. This does not necessarily consume your everyday life. In fact, if you could just find one great opportunity every two years, that’s enough to probably outperform all of Wall Street in your portfolio.

What I love is the idea of getting something out of the horrible amount of time we spend on social media. We waste so much time on social media. I like the concept that we would use it to our advantage.

Yeah, exactly, understand that they’re using data tools to extract what we’re saying on social media, and they have teams of people analyzing it. That’s what they’re doing all day now. And it’s something that we can do more easily because we’re just more connected to ourselves than outsiders who are looking in trying to make sense of it. We understand the language. We understand meme language better than people on Wall Street trying to interpret meme language and what it actually means.

We are the ones creating the language they’re trying to decipher.

Totally. Look, another one of my big investments was Crocs. Wall Street just did not believe that Crocs was getting as popular. They thought it was a joke. I was like, “It’s actually not a joke. Crocs is really trending.” I was just monitoring. I would monitor every single mention of the word “Crocs” on Twitter on a daily basis, and I was astonished. People had to have their Crocs. And they have done such an incredible job revitalizing the brand as a legit, fun, cool brand. I understand why Wall Street didn’t believe it until they saw it in the numbers, but for anyone following Instagram, and following people discussing Crocs on Twitter, and all the sell-outs and the hype, it’s not difficult to understand that it was real.

So let’s say you get an interest in something like that, let’s say Crocs, do you go on and follow hashtags and tags, is that one of your major resources?

I will look at things that are selling out. A lot of times I will search the word “obsessed” and then combine the word “obsessed” with the name of a product. Because when someone uses the word “obsessed” with a product, that’s a pretty good signal that the person is authentically in love with the product. So there’s all these little tricks that I use, things that I look for. And so, after a while you’ll come up with your own tricks, and you’ll start identifying what’s real and what’s not real.

Sometimes it’s very obvious, it could just be a Lululemon thing that’s getting hot. Obviously, Lululemon is a publicly traded company. For you [being a men’s stylist], a big question would be, “Are men really starting to go to Lululemon now?” If Lululemon could win over men, that’s a really big, big deal. Before the numbers come in, before the hard data comes in that Wall Street analyzes, if you could start to determine the hype that men are getting around Lululemon, then you could get in earlier.

But isn’t Lululemon so big already? Doesn’t it work better to invest in companies that are sort of undiscovered?

You’d be really surprised. A lot of people think the same thing. They’re like, “Well, that’s too big. That’s too big.” It could be big, and you could still identify information that’s game-changing for them.

Because you’re looking at increase.

Looking for an increase, yeah, or a decrease. It’s not about one outfit getting really hot. Lululemon might make a bra that starts to trend. Well, is that bra gonna really move the needle for Lululemon? Probably not. But if menswear becomes a thing for them, and all of a sudden they break through to men, and now all of a sudden men are as excited about Lululemon as women have been the past 10 years— that’s a game changer for a company.

There’s a big question on Wall Street, “Is Lululemon going to be as popular globally as it is in the United States?” Because they’ve done a great job here, but now they have to prove themselves all around the world. Well, if you have friends around the world, or if you just observe social media around the world as they’re opening up new markets, and you start to see people in those areas, again, obsessed with their merchandise, stuff is selling out, you can feel the buzz. You just have to make a gut instinct call.

How do you know if a company is publicly traded, that’s probably a dumb question…

No. There are no dumb questions. The best way to figure it out is just simply type in the name of the company on Google, and type in “stock ticker” or “publicly traded” and just see if it is or isn’t. Type in “Lululemon stock ticker” or “Lululemon” and “publicly traded.” That’s what’s so great about 2021. There’s so much information immediately, you’ll come up with 100 things. They’re publicly traded. Here’s their stock ticker. Here’s how they’re doing. It’s really simple to buy or sell stock, more simple than it’s ever been. It’s almost like playing a video game. There’s good and bad things about that, of course. People get addicted, but it really is that simple.

And then what will happen is it takes a long time to retrain your mind to critically observe the world around you and to start asking questions every time you see something. Is that a publicly traded company? Is there a company that would benefit from that? You see these things all the time in your daily life, you’re just not trained to ask yourself those questions. And it takes a long time to do that.

In fact, as a great example, do you remember back when President Obama was first elected, do you remember the yellow dress story with Michelle Obama? She wore a yellow dress on a late night show.

I remember.

It was from J.Crew, and she wore it, I think, to the inauguration. People were so blown away that she was wearing J.Crew stuff on these big media events, that it was a game changer for J.Crew. And I actually had like an US Weekly on my coffee table at the time with Michelle Obama on the cover in her J.Crew dress. And I, as a social arbitrage investor, like—this is what I do. And I missed it. It was right in front of me. I saw the Jay Leno Show. I watched her. I read the article about how crazy it was she was wearing a J.Crew dress. And even though I pride myself in doing this, I missed that one. And so I actually went out and bought the J.Crew dress, and it’s hanging in my closet as a reminder, every single day, of how easy it is to miss something, even when it’s right in front of your face.

I love that, by the way. Why do you think you missed it?

Everything that I’m talking about doing seems so easy, and it really is easy. Yet at the same time, it’s just so hard to retrain your mind to think differently and to pause, have all these pauses during the day, mental pauses when you come across something to say, “Hmm, is there an opportunity there? Could that be connected to a company that’s publicly traded that I can invest in?” It takes years and years and years to retrain your mind, and you only get better at it over time, but it is really difficult. And the best thing about me now having a community of hundreds of thousands of people that are in this with me is—if I miss something, usually someone else gets it. They’ll capture it. So the whole world now is on Discord and message boards, and we’re constantly helping each other. And I always dreamed that I would have a community or spark a community of regular people that would collaborate and collectively have more intelligence and more insights and better information and better research than all Wall Street firms combined. And that’s exactly what I believe we have today.

I know all the hedge funds on Wall Street. I’m friends with a lot of them. I know the sell-side banks. I’m friends with those guys as well, but I believe that these regular people are more powerful in our little Discord community than all of these major hedge funds.

“The big secret is, not only are you not at a disadvantage, but you’re actually at a huge advantage by being more deeply connected to the real world than a professional investor.”

One of our community members got in an airplane, he’s a pilot in a little tiny plane, videotaped the whole thing. He flew the plane to a Peloton distribution facility. He got out and went to the distribution facility, went inside and started interviewing the manager about how busy they were. And then reported, sent the video into the community as his own little private investigation of how well the Peloton distribution plant was doing. Right, who does that?

Peloton would have been a good one to invest in pre-pandemic.

It’s absolutely wild. But that’s how passionate regular investors are about this, because for us, it’s life-changing. Listen, it’s been life-changing for me, no doubt. I think the money I’ve accrued now that’s all going into my foundation will be life-changing for so many kids.

I truly believe, without a doubt, if we were to fast forward 10 years, having a brokerage account and being part of the investor class will be as ubiquitous as it is having a bank account today. And I know that sounds insane, but I have absolute confidence in that based on how quickly things are moving in that direction, especially with young people on TikTok even. A few months ago, the only thing you saw on TikTok was dance videos, and now we have literally thousands of finance creators on TikTok, kids that are talking about stocks and investing and money. And it’s become cool to talk about money. It’s become cool to actually be educated on investing and to be part of the investing class. And I think celebrities even are taking a big role in that. How many celebrities are coming out and saying, “Hey, we’re now co-founders. We’re investors in a lot of these companies”…?

So many.

And celebrities are all investing in really cool companies.

It feels a little bit like taking the power back from these huge social media companies that are buying all of our information.

It absolutely, absolutely is. It’s super empowering to be able to do this just as an ordinary person with a free app and access to the same social media that we share on every day, to actually utilize that to make better investment decisions for ourselves. Listen, I truly think just by becoming part of the investor class, that’s the number one step to narrowing the wealth gap, not just here in the US, but all around the world.

It’s really amazing. I think we’re just in, I would say, the first batter of the first inning of this movement, but I think in the next decade, it will become quite common to discuss this and hear about it. We don’t learn about this in school. There’s really no financial literacy at any level of school, high school, college; it just simply doesn’t exist. So the kids are basically saying, “Hey, you’re not gonna teach us how to be financially literate. That’s okay, we’re gonna talk about it on TikTok, we’re gonna talk about it on YouTube. And we’re gonna teach each other.”

From what you’ve learned, are there any lessons of what not to do?

Yes. The first thing is… I’m gonna say this, and no one’s going to believe it, it’s just something you’ll have to learn over time, but you have to stop thinking that everybody else knows more than you. There’s this feeling, and Wall Street has it so ingrained in our head that we can’t do this. They literally call us “Dumb Money”, and that’s why I call my channel that. They use it as a derogatory term. Because every time you think about that, “I can’t do this, I didn’t go to that school. I don’t have a financial background, and I’m a creative, I’m an artist.”

Investing is creative, okay. The more creative you are, the better investor you will be. Even when you find something, what’s going to happen is you could find the greatest opportunity ever at some point this year, and you are not going to have the confidence to really invest in it. Hopefully you’ll put a little bit of money in, and you’ll learn, and you’ll look back and go, “Wow, why didn’t I invest more in that?” And it’s just going to take time. There’s really no answer other than time, so my biggest advice is to start now, start small, and know that it’s a journey.

You’ll be doing this for the next 20, 30, 40, 50 years. You’re going to be part of the investor class, you will only get smarter not dumber with time. Do not be afraid to make mistakes. You will make lots and lots and lots of mistakes. Follow some people that you think are really interesting that make investing fun for you, and just don’t worry about making mistakes, don’t worry about having to be perfect on day one, it’s not that big of a deal. Think about all the things we spend money on in our life, we spend money on so many things. Just spend a little bit of money investing, investing for yourself, and just watch where it takes you.

I would think a good way to look at it is how I approach gambling if I go to a casino. I’m gonna gamble what I’m willing to lose without getting bummed out if I lose it. I decide for myself what that number is, that I’m okay to lose, and that way I don’t have to overthink it..

Yes, that’s a great way to think about it on day one—although ultimately, listen, you’re investing in companies. And generally, yes, companies, their valuations, can go up or down. But Wall Street would like us to think it’s the same as gambling on roulette; it’s really not. You’re investing in people, ideas, businesses. You might pick a bad one every once in a while, but for the most part, if you’re investing in a bunch of companies, you’re not gonna generally lose all your money. So I wouldn’t overthink it.

And another piece of advice is, try to ignore the noise. I actually watch very little financial news, I consume very little financial media. You don’t have to read financial press, you don’t have to think about numbers, don’t worry about all that stuff, because that’s what Wall Street does. You’re not gonna beat them at their game. You need to play your own game, you need to do something that they don’t do. Don’t try to evaluate a company’s financials a little bit better than the analysts at Goldman Sachs—that’s probably not to our advantage, our natural advantage as regular people. Our natural advantage is identifying opportunities a little bit quicker than they can. So don’t try to be like Wall Street. Try to be smart in a different way than others.

Here’s my last question. Let’s say someone reads this, and they’re like, I just don’t have the time. I want to hire Chris. Can someone just hire you to do this for them?

Even in my community, I don’t have courses, I don’t sell things. I just refuse to do it, because I think people need to be forced to tippy-toe into this world, they have to be. It’s the right thing to do; it’s the right thing to do for themselves, for their families. Even if it’s five minutes a week or five minutes a month, even if it’s just thinking a little bit differently.

Everybody wants to be an investor, and they’re just trying to figure out how they could do it. Trust me, you can do it. You don’t have to buy a bunch of investing books, you don’t have to do all that stupid boring stuff, just start thinking differently, that’s all you have to do is just start thinking differently.



laughing at wall street on LEO edit.