Chris Camillo, author of Laughing at Wall Street, explains how he turned $20,000 into over $70 million in gains by practicing “observational investing” — finding information asymmetry by monitoring social media, consumer behavior, and cultural trends before Wall Street catches on. He walks through his greatest hits (ELF Cosmetics, Beacon Roofing, Palantir, COVID trades, Sphere/Wizard of Oz), his worst trade (QSR/Tim Hortons), and his philosophy that the wealth gap can be solved by getting more people into the investor class.
Speakers: Sam Parr (host), Shaan Puri (host), Chris Camillo (guest, investor, author of Laughing at Wall Street)
Cold Open — Key Quotes [00:00:00]
Chris: You really only need one great trade to be a top 1% investor. The most inherently ground-truth thing of investing — the most important thing, the thing that matters more than anything else — is I don’t look at valuation. I don’t look at PE. All I look at is: is there new information?
Chris: I’ve been reading TikTok comments. That’s where I get most of my alpha from.
Sam: You have Buffett or Munger reading the Moody’s manual cover to cover, just company financials, and you’re like, I scroll the TikTok comments.
Chris: That year I made like $30 million in one year and it was a wild ride.
Sam: You will try to beat the market. You’ll trade with leverage. You’re moving in and out of positions. You’re not a buy-and-hold-forever kind of guy.
Chris: Just before the pandemic I had made the worst trade of my life. I lost a third of my portfolio on a single trade.
Sam: This is where the biggest mistake I ever made was — you break all the rules of investing. All what I normally hear is you should just index, don’t try to beat the market, don’t take any leverage. And you do the exact opposite, right?
Introduction: $20K to $70M [00:00:45]
Sam: You will try to beat the market. You’ll trade with leverage. You’re moving in and out of positions. You’re not a buy-and-hold-forever kind of guy. According to the internet, you’ve done pretty well. I’ve seen some different numbers floating around. Can you set the record straight? What’s the actual story?
Chris: I started with $20,000 in 2007 to try this new methodology — which is the way I was investing when I was much younger, and it worked for me. I call it social ARB investing today, but what it essentially is is observational investing. You’re looking for any change that’s happening in the world — whether it’s a change in consumer behavior, culture, technology, weather, politics — anything that has the potential to be meaningfully impactful to one or more publicly traded companies in either a positive or negative way.
Chris: So if you can surface that change early and connect the dots back to a company that would benefit or be harmed by that change, that’s essentially the entire methodology. It doesn’t really incorporate much fundamental analysis. It definitely doesn’t incorporate any technical analysis. In its purest form, you really don’t even need to know what the stock is trading at when you open a position or when you exit.
Chris: Ideally you’d be completely blind to stock price, completely blind to everything other than the extent to which other investors were aware of that one thing you surfaced that you feel would ultimately be impactful to that company. You enter your position at the point of information asymmetry — when you know that thing and very few others do — and you exit at the point of information parity, when other investors start to learn about it. It sounds so simple and it really is, but there are nuances. To be great at it, it takes time and some regimented processes.
Chris: Is the information you found actually meaningful? Is it a needle-mover for that sector or for that company? Is it really off-radar, or are institutional and retail investors already accounting for it? Are there any other things happening at that moment in time that are equal to or more important than that piece of information? There is a process.
The Core Methodology Explained [00:03:00]
Sam: Of course. I want to go through a bunch of examples. So you take this idea of observational investing, arbitraging information, without being a guy who grew up on Wall Street, didn’t have an MBA, didn’t have 20 years of experience doing this. The story is you take $20,000, start doing this type of investing, and run it up. I’ve seen something like $60, $70, $80 million is how you’ve grown that portfolio starting at $20,000. Is that right? Because that sounds in some sense too good to be true.
Chris: Yeah, it certainly does sound too good to be true. It is accurate. I don’t know the exact number — $70 or $80 million of returns from the $20K. I’ve been audited over the past 17 years. I’ll be re-audited at the end of this year and I’ll fall somewhere around 75% annualized returns, total portfolio, over the 17 or 18-year period since 2007.
Origins: Garage Sales and the Snapple Trade [00:04:30]
Sam: Let’s break it down. You said you started doing this as a kid. I read your book, Laughing at Wall Street, and you talk about starting with garage sales, very simple stuff — noticing things, talking to your brother, talking to your dad, “Hey, could this mean this?” Learning lessons with a very small bankroll, $100 type of deal. Could you take us to the early days? Where did you have that aha moment that this style of investing can work?
Chris: Yeah. I was an entrepreneurial kid. I was really interested in making money before that was a cool thing to do. The new generation — all these kids are traders, they’re trading crypto — it’s like every kid now is like I was back in the ’80s.
Sam: And that makes sense now, because if you’re a kid you’re on YouTube, you’re on TikTok, you’ll see things. But why did you have that itch?
Chris: I don’t know what made me so laser-focused on grinding at age 12, 13, but the way I was going about it was not investing. It was arbitrage — garage sale and estate sale merchandise. I would take buses around the city on Thursday and Friday mornings, sometimes three or four buses before school, to the one estate sale that I had seen in the paper the night before that I thought was most likely to have mispriced merchandise.
Chris: The thesis was that most of these estate sales were run by older women who had a great knack for pricing silver and other things they knew and cared about, but they were really bad at identifying value in male-oriented items — old trains, old watches, anything like that.
Sam: Pre-eBay, right? You can’t just go look up every item quickly and know the current live market price.
Chris: Exactly. Pre-eBay. I’d show up at 5:30, 6:00 in the morning. If you pick the right sale and you’re first in line and you know exactly what you’re looking for, you’ve got a good shot at buying something that’s mispriced. I did that for years.
Chris: I happened to go to the same 7-Eleven every morning and get a bottle of Snapple lemon iced tea, which was like the hot drink at the time.
Sam: Yeah. Snapple used to be huge.
Chris: One morning I went to the 7-Eleven and they had like one quarter of the door space dedicated to Snapple. They had brought in a couple other brands of iced tea — maybe Arizona Iced Tea and a couple others. The clerk told me that’s the way it was going to be going forward due to this new competition.
Chris: Sure enough, I talked to my older brother. He was a stockbroker. I asked him, “Can I make money off of this? This has got to be bad for Snapple, right?” He taught me how to short Snapple with put options. I did it through his account — I was too young to have a brokerage account. I think I gave him $300, which was most of the money I had at the time from garage selling. He tripled the money in about a month because Snapple, for the first time in its history, reported bad earnings due to inventory building up because retailers like 7-Eleven were giving them less door space.
Chris: It was something I had noticed as a kid. And you have to ask yourself — professionals on Wall Street could have easily seen the same thing I saw. But they were so distracted by macroeconomics, noise, government, their jobs, herd mentality — they didn’t see something very simple that was right in front of their face. If I did that as a young teenager, that really means something.
Chris: After that I got really into stocks and investing, but I did it the conventional way. I read all the books — technical trading, fundamental — and I tried every type of investing method. And of course, basically nothing worked. I was just like everybody else.
Chris: Later on in my life, when I was in my 20s and I had a job and wasn’t making as much money as I wanted, I got back into investing — most aggressively in 2007. I said, why don’t I try this observational approach I did as a kid? What I did as a kid was reflective of what Peter Lynch was doing, though Peter Lynch used observational investing as just part of his methodology alongside a lot of fundamental analysis.
The Three Schools of Investing [00:09:30]
Chris: So let’s break it down. There are major schools of thought around investing. Number one, passive investing — don’t try to beat the market, just be in the index. You go as the American economy goes. Then there’s, I think I could do better than indexing. There’s technical analysis, which is some cross between horoscopes and fantasy football. A lot of people believe they can read patterns and signs in the charts. I’ve never met anyone smart who’s really good at that, but it’s possible.
Sam: So, there’s technical trading, there’s fundamental analysis — the Buffett style, trying to understand intrinsic value, the durability and quantity of cash flows. And then there’s what you do, this other school of thought. My short summary is you’re looking for significant behavioral change. Teenagers are now doing this thing. You gave the example of women changing their bra preference from wired push-up bras — Victoria’s Secret is on top — to you started noticing a lot of people talking about “bralettes,” and hey, that’s probably going to affect the number one bra player who isn’t even carrying bralettes.
Chris: Let’s not restrict it to behavioral change. Let’s say any change. It could be a hailstorm that positively impacts a publicly traded roofing company. Anything that’s change-oriented and not well-known by the investing public — not priced in.
Greatest Hits: Beacon Roofing and Google Trends [00:11:00]
Sam: Let’s go through a couple of examples. Take me through some of your greatest hits.
Chris: There have been north of 80 to 90 over the past 18 years. A handful didn’t work out. But for the most part, almost every one has worked out.
Chris: One that popped into my head is actually one of my favorites. Every spring, I would track the number of people searching for the words “roof damage” or “roof repair.” It’s a free data source — anyone could leverage Google Trends. When there’s a hailstorm, people will immediately start Googling “roof repair” the day after. At the time there was a publicly traded company called Beacon Roofing, one of the largest roofing companies in North America. If the hail season was particularly damaging, that would meaningfully impact their bottom line.
Chris: Wall Street would generally use insurance sector reports to analyze Beacon Roofing before earnings. But those reports are delayed by 5, 6 weeks after the hail storms happen. I had discovered a real-time data source. And even if you knew there was a terrible hailstorm from the news, what makes the difference is whether it hit a super-populated area. The only way to know how many people were actually impacted is the volume of people searching for roof repair.
Chris: Google Trends gives you 15 years of historical data, so you can look at every spring and see where the peaks are. There was one hail season in particular where the peaks were nearly triple anything I’d seen before. I went in on a very large, very levered call long position on Beacon Roofing. That would be considered a greatest hit.
The Garage Sale Principle Applied to Wall Street [00:13:30]
Sam: My understanding is you applied the same principle from garage sales. At estate sales you said, “These were run by older women. They knew the price of jewelry really well — you’re not going to get a deal there. But they may not know what their son’s baseball card collection is worth, like this 1996 Topps Kobe Bryant rookie card.” And you applied that to Wall Street — most of the people in finance are guys, white guys in New York of a certain age. So instead of competing where they’re strong, you find their blind spots.
Chris: That’s how you identify the lowest-hanging fruit. And I would say the vast majority of my big wins were around changes in consumer behavior and culture that were primarily female-oriented, youth-oriented, or tied to some demographic that wasn’t older, white, northeastern investors.
The ELF Cosmetics Trade [00:14:30]
Chris: Something like the moment that Jeffree Star — a beauty influencer — made a single video about this drugstore cosmetics product by ELF Cosmetics that was just as good as a $60 product. The ELF primer putty. That was an old trade now, but ELF was trading at like $7 a share before it blew up to $170.
Chris: By seeing a single YouTube video that had 10 million views, about a company nobody cared about — all of a sudden the most influential content creator in the beauty world is saying it’s as good as one of the best products in the world. I went down to Walgreens by my apartment and stood there all day and watched moms coming in with their kids and buying out all the ELF products. Instantaneously, this drugstore brand at a price point of like $8 for any piece of makeup became cool because this one person said it was.
Chris: I called one of the analysts on Wall Street who was covering ELF Cosmetics. I said, “What do you think about the Jeffree Star video on ELF? Has that impacted the way you’re analyzing ELF this quarter?” The analyst said, “Who’s Jeffree Star?” At that moment, I knew everything I needed to know about that trade.
Chris: These guys are not watching YouTube videos of beauty influencers. But that’s all I do. I spend on average 3 to 4 hours a night reading through TikTok comments. That’s where I get most of my alpha recently, because that’s the place where people express themselves most freely across the largest number of topics.
Why TikTok Comments Beat Wall Street Data [00:17:30]
Sam: That’ll get you laughed out of the room with serious investors. You have Buffett or Munger reading the Moody’s manual cover to cover, just company financials. And you’re like, I scroll the TikTok comments — and that’s why I’m compounding 75% a year for 20 years.
Chris: Well, here’s what you have to determine as an investor: who do you want to compete with? It’s not important for you to be smart. It’s important for you to figure out how to be smart in a totally different way than others. Do you want to compete with top mathematicians as a technical trader? Do you want to compete with droves of Wharton and Harvard grads doing financial analysis? Maybe you can do that a little bit better. But honestly, 99% of us probably don’t fit into one of those two camps.
Chris: So how could the 99% get an edge on Wall Street? You have to look for edge in a place where your competition — conventional institutional and retail investors — are not willing to go. Wall Street likes correlated data. They like certainty. They like proof in historical correlations. So the data I am trading is conversational data, because Wall Street primarily uses transactional data — credit card receipts they spend millions of dollars for, synthesizing all this transaction data to figure out what’s happening at a company before earnings.
Chris: So how do you gain an edge on a hedge fund that’s spending millions and has fleets of people analyzing credit card receipts? Well, what do you do before you buy something? You talk about buying it. There’s a billion people talking about their interests and what they want and what they did every single day. If they see a video about a piece of apparel, you’ll have 30,000 women commenting whether they plan to buy it. You can actually measure the depth of interest in an infinite number of things even before that’s provable through sales.
The Ticker Tags Platform [00:21:30]
Sam: There’s a great story — the trending tab on Twitter. The guy who created it, Abdur, was basically trying to do sentiment analysis using Twitter. It wasn’t working that well. One day he’s on a train and his program is not spitting out sentiment analysis, it’s just spitting out city names. He realized the Olympics was going on, and each country being shown in the opening parade was getting mentioned a lot. What he realized was that if you pay attention to the delta — if nobody’s ever talking about Zimbabwe, and suddenly way more than usual are talking about it, that’s got to mean something. So he created a product that tells you what people are talking about in an abnormal way on Twitter. Twitter bought that and made it the trending product.
Sam: It sounds like you were manually doing something similar — “I noticed the slime trend is getting really big. Well, how do you make slime? You need Elmer’s glue. And Elmer’s is about to have a huge quarter.”
Chris: Me and my business partner actually created a platform called Ticker Tags in the mid-2010s with Twitter. We had access to the Twitter firehose — a 10% randomized sample of every tweet in real time — and we hand-curated about 1.5 million word combinations that represented how people were speaking about every product, brand, basically anything connected to any publicly traded company. Organized into a taxonomy, every company had 300 to 1,000 combinations of words.
Sam: What would be an example? If I’m Nike, what do I care about?
Chris: So you mentioned slime. Newell Brands makes Elmer’s glue. So “Elmer’s glue” would be a tag for Newell Brands. “DIY slime” — which uses white Elmer’s glue — would be a tag, because if DIY slime gets more popular, that’s something a Newell Brands investor would want to know. We were monitoring in real time the frequency of mentions of those 1.5 million words, benchmarked against historical norms including seasonality. When there was any anomaly in speech patterns across Twitter that impacted a subject matter we’d curated as potentially impactful to a publicly traded company, our system would flag it.
Chris: That platform was basically me taking my methodology and institutionalizing it for Wall Street. We sold it to hedge funds and sell-side banks. At the time, people expressed their opinions on Twitter about everything they were doing in life — the way people now do on TikTok.
Sam: Was that a successful company?
Chris: I spent years flying to New York nearly weekly, training the top sell-side banks and probably five or six of the top 10 hedge funds in the world on how to interpret this observational, conversational data and attempt to correlate it. And they just had very little interest. They had interest in the results, but they couldn’t figure out how to build teams around it. Hedge funds hire mathematicians for quant trading and traditional fundamental analysts for number crunching. They didn’t really have 20-something-year-old females on staff who were savvy at interpreting conversational data.
Chris: Wall Street does things the same way they’ve always done things. It’s really difficult for them to say, “We believe this thing matters,” when there’s no historical correlation between the speech pattern of that subject matter and the stock price. Speech patterns evolve, so that thing people are talking about could be entirely new.
Chris: That’s unfortunate for Wall Street, but it’s fortunate for retail investors. This is still a dataset they’re scared of, still a methodology they have a hard time wrapping their head around. If you were to tell someone, “Hey, I’ve been reading TikTok comments and I believe this new show at the Sphere in Vegas, Wizard of Oz, people are super hyped on it” — sounds oddly specific.
Sam: Is that actually a trade you’re in right now?
The Sphere / Wizard of Oz Trade [00:25:00]
Chris: Yeah, it was. Sphere, the Wizard of Oz — that was actually one of my largest wins. It came from reading comments on Wizard of Oz the first 48 hours it was out and essentially making it a monstrously big levered position.
Sam: Sphere’s up 114% this year.
Chris: Well, it was a levered options trade, so it was a lot more than that. A lot of what I do when I have high conviction and a very defined window of time — in the case of Sphere, people were counting seat sales. You’re able to go in and see how many seats are available for a show that’s a week and a half out. Over the course of a few weeks, other traders — retail, not even Wall Street — were saying, “We’re seeing seats sell out like never before for a show.” So what I had interpreted from early user reviews ultimately came out in seat sales that other retail investors started trading, and then Wall Street eventually picked up on it when the company came out and said they’re adding new shows because they’re selling out everything and increasing profit guidance.
Making the First Million [00:27:00]
Sam: The show is called My First Million. Do you remember when you made your first million?
Chris: I 100% do. I was working at a company called Eve Rewards in Dallas, Texas, with one of my best friends Patrick. It was not far past when I started this in 2007, when I had grown $20,000 to a few hundred thousand. I said, “This is absolutely crazy. I think I’m going to hit a million dollars here within the next year or so.” A few months later I hit a million dollars. I’ll never forget walking into his cubicle and saying, “I did it. I cannot believe my account just hit a million dollars.”
Chris: I wrote my book Laughing at Wall Street about 2, 3 years later because there was this tracking service called Covester — I think they had 40,000 accounts including mine — and it would monitor how well you’re doing month-to-month and rank you publicly. There was a moment when I was the number one ranked investor on Covester. I was on a few different business shows like Fox Business. Then I got a book deal.
Chris: When I wrote Laughing at Wall Street, it was $20,000 to $2 million — 100 times your money in 3 years. At the time, there was a small piece of me that thought, am I just part of the long-tail statistical anomaly?
Sam: You flip a coin 100 times, if you get enough people doing it, somebody will land on heads 90 times and you’ll think they’re a genius.
Chris: 100%. I doubted myself. But I had a really defined methodology and I knew the narrative behind every one of my trades. It wasn’t some random formula that just happened to get lucky. Intuitively it just makes sense — you’re uncovering important information a little bit quicker than other people and connecting dots a little quicker. The methodology at its core was really valuable. But I still didn’t believe that three years was enough.
Chris: I said, if I can get to 5 years and keep this track record up, that would be insane. I got to five and said, let’s see if I can push it to 10. Then I got to 10. Now here I am, going on 18 years at an average of mid-70s total portfolio returns. I truly believe I can hit 20. That’s the new number in my head. All I have to do at this point is not mess it up. But at the same time, it’s very hard generating returns that high.
Portfolio Mechanics: Profits, Reinvestment, and the Big Mistake [00:31:00]
Sam: Do you take profits every year? Do you reinvest everything? Because you compound at that rate for long enough, the number is actually much bigger than $70 million.
Chris: Yeah, it’s almost a billion dollars. So this is where the biggest mistake I ever made was — and I’m now resolving it. About half of my life is trading public equities through observational investing, social and conversational data. The other half is being an entrepreneur. I’ve had some success as an entrepreneur, and like a lot of entrepreneurs who have success, you start investing in other entrepreneurs. I’ve been an early-stage venture investor for 20 years, invested in 160 early-stage companies. My performance investing in early-stage companies is pretty much average — maybe 10, 11, 12% annualized returns.
Chris: I have pulled out almost all of my gains every single year for 18 years and taken that money and invested it in the private market. And that has been really unfortunate for obvious reasons — the opportunity cost of my capital is so high. I never believed in myself enough on the public side to think, “I’m just going to keep doing 75% average returns.” I always felt like I needed to make my home runs in early-stage VC. I finally came to terms a few years ago that that was a really bad decision.
Chris: It’s taken me about 4 years to pull myself out of early stage, because when you’re that big an early-stage investor, you’re taking hundreds of meetings with founders annually and it takes a long time to unwind yourself from that ecosystem.
Sam: Peter Lynch had this principle — don’t cut your flowers to water your weeds. Don’t sell your winners to diversify back into losers. In a way, what you were doing at an overall level — performing at 70% in one strategy and 10 or 11% in the other — that’s a water-your-weeds scenario.
Chris: And by the way, I love Peter Lynch maybe more than any other investor, but I don’t believe in any preset rule of investing like that. My methodology is very clean. You invest when you discover something others haven’t discovered yet that will be meaningful to a trade, and you exit as soon as others have figured it out. That’s literally it. If that stock goes up 100x or 200x, you don’t sell it because it’s up 200x — you sell it when other people find out the information you’re trading.
The Palantir Trade [00:35:00]
Chris: One of my most controversial trades, over a year ago, was Palantir. I went all-in, unbelievably levered, in Palantir at $30 a share. I was very public about it on my YouTube channel, Dumb Money Live. I got so much heat — even from Palantir investors going, “You’re an idiot. We’ve been in this thing since $6. You’re going to do this at $30 a share?”
Chris: I said, I’m not trading the information you were trading at $6.
Sam: What was the two-line reason you were so bullish on Palantir at that stage?
Chris: Because people didn’t even understand what they did. They didn’t understand where Palantir would actually sit in the stratosphere of the AI wave coming as a beneficiary of it. Palantir was just starting to scrape the surface of this new product with clients and it was unstoppable. There was going to be this 12-month window when everything Palantir had been working on for years — they finally had the case studies done with their first set of clients and were just going to start to steamroll and add clients. They were just scratching the surface of their TAM and the market didn’t realize that.
Chris: People were like, “There’s no way you can go levered on Palantir at $30 with its valuation already so out of whack.” My response: the valuation is irrelevant to me. I don’t look at valuation. I don’t look at PE. All I look at is: there is new information about to come online for Palantir that will bring in a whole new group of investors. However people are valuing Palantir today based on existing information, this new information will be settled into the stock price. And that’s exactly what happened. Palantir went from $30 to $160, $180.
Position Sizing and Leverage [00:38:00]
Sam: When you say you went really big, you’re taking leverage which cuts both ways. Let’s say you have a $70 million portfolio and get a lot of conviction about something. How much are you actually betting at a high-conviction moment? Are you putting 1%, 10%, 30%? And how do you manage the risk of it going south?
Chris: Just to be transparent — it’s $70-million-ish of returns, of gains over that time. Those gains were taken and put into other things like private companies. I’m not managing that as a portfolio.
Sam: Let’s say that’s gains. You’ve gotta pay taxes. A lot of your stuff sounds like it might be short-term —
Chris: Almost exclusively.
Sam: And then you’re reinvesting that into your addiction in startups. So percentage-wise, when you have a high-conviction idea?
Chris: I’m usually investing between 5 and 10% of my entire liquid portfolio into that idea via options. So if you’re wrong, you just lose 5 to 10% of the portfolio.
The COVID Trade [00:39:30]
Chris: A good example of where I did that and was wrong three or four weeks in a row, losing 30 to 40% of my portfolio, was during COVID. I was tracking the virus coming out of China, using Google Translate on medical reports to assess how big a deal that virus was. It became very clear to me it was going to be a global pandemic. So I was taking 10% of my portfolio and putting it into puts in the S&P, casino stocks, Vegas casino stocks, and airlines every week. The market wasn’t moving down. It just wasn’t accepting COVID for what it was. I got to a point where 30 to 40% of my portfolio was gone.
Chris: I did it again the week after. That week was the first week the market cracked — down 2%. Then the next week it really hit. That was one of the biggest trades of my life. That year was like 370% annualized return, total portfolio, partially because I had shorted the pandemic early on even though it was a little too early.
Chris: Then 2 days after it bottomed, I had a selection of about 14 or 15 companies that should have never gone down at all. Companies ranging from Hewlett Packard — where everybody would want to go buy printers for their house — to Peloton because you can’t go to the gym, Shopify because you’re shopping online, Amazon obviously, Campers World because you can still go camping, boat stocks. I bought a company out of Canada nobody had ever traded before that owned Schwinn bicycles because Schwinn had the biggest bicycle sales in the history of the company — that company went up 8 or 9x over 9 months.
Chris: I had these 14, 15 companies that should be doubling right now, and instead they were all down 30, 40, 50% just because the whole market traded down. I always knew I was going to go levered long in these companies, but I didn’t want to do it until the market became less erratic and irrational. So once the markets finally started to normalize, I took all the gains from shorting the travel stocks and the market at large and put them into levered positions in these 15 companies.
Sam: That year I think you made $30 million?
Chris: That year I made $30 million in the market. It was a wild ride. The most interesting part of that narrative is that just before the pandemic, I had made the worst trade of my life. It was psychologically damaging. I lost a third of my portfolio on a single trade, just months before the pandemic started. The thing I’m most proud of is that I was so down and out about that trade, and I still found a way when I had all that conviction on COVID to go all in on my thesis — even though my account was so brutally damaged that if I got another one wrong, it would have been an unbelievable implosion.
The QSR/Tim Hortons Trade — The Worst Trade [00:44:00]
Chris: The trade that went wrong was a company called QSR. They own Burger King, Popeye’s, and Tim Hortons. I was so convicted that the company would have the best earnings quarter in its entire history because two of the three companies had anomalies on the positive side.
Chris: Burger King had the Impossible Whopper, which was unlike anything the company had ever done in terms of sales traction. Popeye’s had the crispy chicken sandwich — this is the chicken wars, if you remember.
Sam: Chick-fil-A. Yeah.
Chris: At the time. That crispy chicken sandwich at Popeye’s would literally sell out in like two hours every day. Nobody had ever talked about Popeye’s in the history of the company until that sandwich.
Chris: But then there was Tim Hortons — unfortunately the biggest piece of the company — a Canadian coffee and donut shop that had basically been around forever, not doing awesome, kind of flatlining. They would have had to have a really bad quarter to screw up my trade. And it was just a really difficult company for me to extract information on, because it was Canadian and people just didn’t talk about it that much. There was nothing happening there. I saw zero reason why they should have an anomalous bad quarter. And that’s exactly what happened. They just randomly had one of the worst quarters ever.
Chris: And the wildest part — I take a lot of pride in doing really intense, comprehensive due diligence. On a high-conviction trade, I’ll put 60-plus hours into it. I’ll uncover every piece of contextualized information globally through every social media. I will sometimes travel if they’re a retailer and visit stores and talk to clerks. But because there were three things to deal with — Burger King, Popeye’s, and Tim Hortons — I just assumed, “Tim Hortons, how bad can it be?”
Chris: Well, they had the Tim Hortons annual meeting a few weeks before earnings in Florida that I didn’t realize was happening. But if I had done my homework, I would have been there. Not because I would have gotten in, but I would have hung out at the bar and talked to all the franchisee owners. From what I understand, there was a revolt at that meeting — franchisee owners going public about everything the company was doing wrong, their sales being slaughtered due to recent corporate decisions. It was really harsh. If I’d just been in the building at the bar, I would have been well aware of that.
Chris: I learned that you really have to be comprehensive in your research if you’re going to take a levered bet. You can’t be lazy.
Current Bets: Bloom Energy and AI [00:50:30]
Sam: What are the bets you’re looking at now? A lot of these examples are from the past 17 years. Where are you now on the AI side?
Chris: Two of my favorite AI picks right now. One is Bloom Energy. The energy trade is a big one, really misunderstood by most investors. Bloom Energy has a really different approach to powering data centers — not using big gas turbines. They’ve worked for 20 years on a technology that’s actual DC technology where, instead of combusting gas, it’s a chemical change that creates the energy. And they have a really quick timeline to energy for a data center.
Chris: If you have a data center and you could get energy through Bloom and get it up and running 6 to 12 months quicker than waiting in line for gas turbines and going through all the approvals, that’s a really big deal. That’s why Bloom Energy is up like 5 or 6x over the past 8 or 9 months.
Sam: But there’s still controversy. It’s somewhat unproven. They only have a couple of big hyperscaler deals — one with Oracle. And then you have news events like, now we’re building data centers in space, right? SpaceX is preparing to IPO, all of a sudden there’s this narrative — didn’t everybody realize we’re just going to be doing compute data centers in space? So the market is so ADD that it’s changing week to week based on whatever the hype story is.
Chris: For me, I think Bloom Energy is definitely one of my favorite AI plays right now because they will enable data centers to get up and running meaningfully quicker over the next 3 to 5 years. I think that’s a company that’s going to see its earnings double basically year-over-year for the next 3 to 4 years. They’re still very much misunderstood. They’re actually going to be the topic of my next Dumb Money Live episode — I’m going to go in deep on Bloom Energy.
Sam: Do you publish your portfolio or trades somewhere?
Chris: I don’t ever publish trades. I sometimes speak about trades on a really high level. The last thing we ever want is other investors trying to mirror our trades — we don’t think it’s healthy behavior. I always tell investors to steal my ideas and run with them: take the idea, poke holes in it, do all of your own research, and then come back to me and tell me where I was wrong. Ultimately go off and make your own trade based on your own risk-reward, because we all have different degrees of risk tolerance.
Sam’s Honest Assessment [00:54:00]
Sam: I’ll be honest with you. This is not my world of expertise. I’m a founder first. My investing is very simple — I own some indexes and stocks I understand, tech companies basically, because I grew up in the tech industry. My investing outside of that is private angel investing, again tech. And then my own private equity — businesses I can own and affect with things I know how to do operationally or promotionally with this podcast.
Sam: You’re interesting to me because the story is great — $20,000 to $70 million in gains. And your approach actually lines up with what a lot of great investors do and say, which is they try to surface the signal from the noise: what is the actual important thing I need to know about this company that I can believe before it is obvious, true, and proven?
Sam: But sometimes you say things like “99% of people can go do this” and “the game is rigged — but it’s rigged in our favor.” That part seems untrue. If what you’ve done is real, it’s in many ways because you have a very unique skill set and upbringing.
Chris: No, no. Let me explain that because it’s important. The last thing I want is people to listen to this and think, “Oh cool, I can just go trade levered up off of observations and I too will turn $20,000 into $70 million.” There’s a reason that’s not common. There’s a reason you get a book deal, there’s a reason people will follow you — because it’s not a common result.
Chris: A lot of it is interpretability — interpreting the signals, trying to figure out what’s actually important, whether it’s already priced in, what it means, who benefits, the second-order effects. That’s not something incredibly simple that everybody is going to do. There’s a big difference between “anybody can” and “everybody will.”
Chris: I view it very similarly to startups. An entrepreneur can come on here and say, “Look, it’s not rocket science — I’m not any smarter than you, I just did this, this, and this.” And it’s true that it was in the capacity of anybody to do. But definitely everybody won’t, and definitely everybody should not try, because they don’t have the nature, the disposition, or the risk tolerance.
Sam: You’re this sort of puzzle. Normally if I hear a story like this, it’s too good to be true. It violates a lot of the fundamental wisdom about investing — buy a great company and hold it for a long time. I think it’s very cool. But I hesitate because I think this is not something a lot of people could or should do.
The Wealth Gap Argument and Risk Buckets [00:58:30]
Chris: I couldn’t disagree more. Over a long period of time, generating almost $100 million from $20,000 — yeah, that’s not easy to do obviously. But I think the biggest issue is simply bucketing money and having risk capital.
Chris: The number one thing preventing someone from doing this is thinking they have this one bucket of capital — for their life savings, their kids’ college, their retirement — all as one. The concept of being a regular person who observes something and connects the dots and puts a levered bet on it — you’re not going to do that unless you have your money properly bucketed. You have to have risk capital. I don’t care if it’s $50 or $50 million. You shouldn’t be waiting until you’re part of the ultra-wealthy class to think you have risk capital.
Chris: Everyone should have a big money account — and the big money account is the account where yes, you get wealthy quickly. You do that by taking big swings on things you really believe in. The only way you’ll psychologically do that is if you fund that account with money that is not being stolen from other areas of your life.
Chris: I call it the frugality tradeoff. Maybe you mow your own lawn, make your own coffee, clip coupons. People don’t want to clip a dollar coupon. But if you think about every dollar in your life as potentially being $100 — 100x, which is 100% feasible over a long period of time if you invest aggressively with leverage and get a few wins — then you’ll clip that dollar coupon because that dollar coupon is clipping a $100 coupon. You’re going to make your own coffee because instead of saving $5, you’re saving $500.
Chris: Every time you make one of those tradeoffs, you take that money and put it into your risk bucket.
Sam: Your risk bucket. Right. And by the way, this is not financial advice — this is just how you did it.
Chris: I graduated in the bottom 25% of my high school class. The bottom 20%, the way college is today, I would not have gotten into any university in the United States. Okay, pretty much today in 2025 with my grades.
Sam: This is why I love doing the podcast. You can get people who make their money in all different ways. We just had John Morgan, the biggest personal injury lawyer in the world, $2 billion a year. He started his career working at Disney World as Pluto. Then he started — because of that formative experience — he took the money from the law firm and started building little attractions, like fairs, like the museum of crime and history. He’s made a killing doing that.
Sam: What I love about the podcast is I get to hear people with completely different blueprints and playbooks they 100% believe in, and I get to decide. Does that sound interesting, does it suit me?
Sam: I don’t agree with a lot of what you said, but I found it all very interesting. And there are some things — I’ll be totally honest — if you had a paid course somewhere, I would be like, “I can’t run this episode” because I’d feel like this guy is selling this dream: just go get in the TikTok comments, find an observation, lever up, make a trade, one trade will change your life. That is a scary principle. It’s a heretical idea to a lot of people. Why is it important to you that the average listener believes this and goes and takes action on it?
The Mission: Getting People Into the Investor Class [01:03:00]
Chris: My overriding purpose is to inspire every human on earth to enter the investing class, because I think it’s the only way we’ll ever solve the wealth gap. There’s no way to solve the income gap — that’s an exceptionally difficult problem. The wealth gap is solvable by bridging more humans into the investor class.
Chris: Everything I do on X, everything I do on YouTube, every podcast I do has a single mission: inspire other people to start investing on their own. By all means, if that means just throwing money in the S&P in an ETF, awesome. But there’s no reason to stop there. I know that people love the concept of hope and having an opportunity to do something truly great in their life. So many people when it comes to income are stuck. Their job is not going anywhere.
Chris: I am not a proponent of people quitting their jobs and becoming entrepreneurs and taking all this massive personal risk. I think there are very few people capable of doing that. I think this roadmap is way more achievable. Start making tradeoffs. Come up with a big money account. Do it through tradeoffs and frugality. Learn how to use leverage. Learn how to take big risks with what I call other people’s money — because it all comes through tradeoffs — in things you believe in. Because you can do this.
Chris: There is nothing cooler than when you’re just a regular person and you make a grand slam in the market. You 30x your money, all of a sudden you have financial independence in life. I don’t know many things more important, because it helps solve so many other issues. So many humans are just depressed because they look at their life and they’re like, “This is my job. These are my expenses. This is inflation. Holy crap, I’m screwed. I will never be the person I want to be for me or my family.” I want to inspire people that it doesn’t have to be that way.
Beyond Investing: The Framework Applied to Career and Business [01:06:00]
Chris: This isn’t just about investing. The same methodology of identifying change in the world, tailwinds, and trends should apply to career, should apply to entrepreneurs. I’m about to start another business, and it’s directly tied to the analysis I do discovering change in the world.
Chris: We’re about to embark on this journey of abundance. It’s not going to be like we hit the age of abundance in 5 years and we’re not working. It’s going to slowly happen over decades. People will be working a little less, have a little more free time, more flexibility to dive into the things they care about. Wealth signaling will become even bigger in the future than it is today. There are so many massive changes happening in the world that if you’re an entrepreneur figuring out where to spend your time, or a young person figuring out your career path, you need to be doing more analysis on where the opportunity is. These are some of the biggest decisions of your life.
Sam: Especially in Silicon Valley — people will take a job and you realize you’re investing all of your life force, your creative energy, you’re getting stock options, but you never thought about it like an investor. You’re just happy you got the job versus looking at the job market the way an investor looks at companies. Even if you’re not investing capital, you’re investing your time.
Sam: You said you’re launching a new business — what is it?
The Private Jet Venture [01:08:30]
Chris: It’s related to the private jet industry, which I believe will be one of numerous beneficiaries of us entering into this age of abundance — people having more. If you want a glimpse into the future, look back to the pandemic. That one year when we had an abnormal amount of time and excess money due to the wild stimulus — that’s a preview of what the age of abundance will look like. What did we do when we had more time and more money? We dug into our hobbies, our interests. We did things that now that we’re back to this world, we do a little bit less of.
Chris: If we truly get the industry of intelligence, automation, and robotics to help us do the vast majority of repetitive work, I think the entire world has an opportunity to become more creative, spend more time with their families, with their friends, doing things that are meaningful. Travel certainly will become a larger industry, not a smaller industry. I am ultra long on the private jet sector — even though I carry too much guilt to fly private myself. You’ll never see me on a private jet, but I’m very bullish on the sector.
Wrap-Up [01:10:30]
Sam: That’s amazing. Chris, thanks for coming on, man. I appreciate you. People can go find you — you’ve got your show Dumb Money Live on YouTube. Thanks for coming on.
Chris: The only place I am personally is X, @ChrisCamillo. But dumbmoney.tv has all the socials. Thanks for having me on. I appreciate it.
Sam: Very cool. Well, that’s it. That’s the pod.