Why I Believe September Will Be HUGE For Stocks, Bitcoin, And Gold

3 Sep 2025 · 22 min

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Podcast Notes: From the Desk of Anthony Pompliano

Episode Title

Why I Believe September Will Be HUGE For Stocks, Bitcoin, And Gold

Episode Overview In this episode, Anthony Pompliano discusses the potential for an upward trend in financial markets during September, which historically has been a down month for stocks, Bitcoin, and gold. Pompliano believes that current economic conditions may lead to a breakout in these asset classes, contrary to historical patterns.

Key Takeaways

  1. September Expectations
  2. Historical Context: Traditionally, September is a month of declines for financial markets.
  3. Pompliano's Prediction: This year, he believes that September could see an increase due to:
  4. Looming Rate Cuts: Anticipation of interest rate decreases could buoy markets.
  5. Investor Sentiment: Poor sentiment may lead to a reverse effect where fears of market declines actually push prices up as positions adjust.
  6. Lower Entry Prices: Assets like Bitcoin are starting September at lower prices compared to previous highs.
  1. American Capitalism
  2. Strength of the System: Pompliano highlights the robustness of American capitalism, noting it as the most successful economic system in history.
  3. Meritocracy and Competition: Capitalism allows for competition that drives better outcomes and innovation.
  4. Access to Risk Capital: The U.S. provides advantageous conditions for startups, enabling them to raise significant funding even on high-risk ventures.
  5. Quote from Jeff Bezos: Emphasizes that the U.S. has superior avenues for venture funding.
  1. Economic Trends
  2. Resilience of the Economy: Contrary to predictions of recession, a robust summer rally has occurred, and market activity is strong.
  3. Merger & Acquisition Activity: Significant M&A activity indicates confidence in the market, with over $1.1 trillion announced since June.
  1. Saquon Barkley’s Investment Journey
  2. Profile Overview: Polina Pompliano shares insights about NFL star Saquon Barkley, who has successfully transitioned into the investment space while still playing football.
  3. Investment Philosophy:
  4. Saquon has focused on building a tech portfolio as a way to ensure financial stability beyond his athletic career.
  5. He took a portion of his endorsement deals in Bitcoin, showing his belief in the cryptocurrency despite initial skepticism.
  6. Key Insights:
  7. He views investing as a means to achieve permanence in the face of a fragile athletic career.
  8. His approach to building relationships with founders and making informed investment decisions has proven successful.

Detailed Discussion Points

September Market Predictions

  • Contrarian Thinking: Pompliano suggests that prevailing negative sentiment around September could create opportunities for upward movements as market participants reassess their positions.
  • Historical Patterns vs. Current Data: He acknowledges that while history often repeats, it can also present opportunities for deviation, particularly when everyone is focused on past trends.

The Role of American Capitalism

  • Economic Incentives: The competitive nature of U.S. capitalism fuels innovation and progress.
  • Impact of Government Policies: Pro-business policies are essential for fostering an environment conducive to investment and economic growth.

Saquon Barkley’s Investment Strategy

  • Investing During Peak Career: Barkley’s focus on investing while still active in the NFL showcases a proactive approach to wealth management.
  • Comparison to Athletic Performance: He equates the volatility in investing, especially in crypto, to the unpredictable nature of football performance.
  • Team Dynamics: Saquon’s investment strategy is supported by key partnerships, including his business manager Ken Katz, highlighting the importance of collaboration in successful investing.

Conclusion Pompliano wraps up the episode by encouraging listeners to keep an eye on the potential for positive market movements in September and the role of American capitalism in driving economic success. He also emphasizes the importance of curiosity and proactive strategies in investing, as illustrated by Saquon Barkley.

Call to Action Pompliano encourages listeners to subscribe to his channel in pursuit of reaching one million subscribers, reinforcing the idea of community and shared growth in financial literacy and investment strategies.

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For more insights and to follow Anthony Pompliano, be sure to check out the links provided in the episode description.

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Transcript

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0:28Hello, everyone. We've got a lot to discuss today. Before we get into today's show, you know how it goes. My goal is to get to 1 million subscribers and I need your help to get there. We have 20 ,435 different subscribers right now, but that's not a million. So please hit the subscribe button right now and help us get to that goal. Let's get into it today. All right, ladies and gentlemen, most people know September. It is a down month for stocks and Bitcoin historically. I don't know what it is. Maybe people come back from summer. They got the summer blues and they miss all the summer fun. But now I think that maybe this September, we're going to get an up month.

1:05Well, stocks in Bitcoin. And here's exactly why. Everyone thinks it's going to be a down month. The second everyone gets off sides and thinks something's going to happen, immediately I started thinking maybe the opposite has higher odds. Now, again, doesn't always work, right? There are times where people have heard me. I had a similar thought when nobody thought they could balance the budget. I said, ooh, there's probably higher odds that they could balance a budget than people are giving it credit for because everyone is so convinced it's impossible. Right? I don't think that's true. Right? So I saw what was happening.

1:39Right? I don't think we can get to a balanced budget. September up, that's not that crazy. Right? Especially because we were down in Bitcoin from the all-time high on September 1st. So our entry price into September is much lower. So I think that we could have a up September and a up Bitcoin because one, you got that entry price. Two is you're going to get the rate cuts. And I do think that that'll be pretty bullish. And then three is I think that there's a lot of people who just are convinced like, oh, it's always down. Doesn't that create the flywheel effect of it always being down? People think, OK, cool, it's going to go down.

2:17Let me sell my stuff now. And then it proceeds to fall even farther. So, yes, the question is just are people going to sell because of that, right? I think the month of August was this past month was the first down month for August in the year after having in history for Bitcoin. I think that's true. So like, well, August is always up in the year after having. Right. It's always for 15 years that's happened. Well, it didn't happen. So September. Right. Could we get the opposite effect again? 75 percent confidence. Like that's pretty high, but I'm not 100 percent confident in that. And so I just think that people, when you start to see people regurgitating the same thing, I see people all over the internet, September's down, September's down, September's down.

3:02Like, well, what if it goes up? Well, why would it go up? Well, you have interest rate cuts, people are off sides, you know, all this stuff. Like, okay, that could be interesting. So I do think that people just gotta be very careful with looking at history and saying this always happens. Usually by the time people start to identify this always happens, usually is about the time where this always happens becomes that used to happen. Now we're doing something else. Now I'm not saying with a hundred percent confidence that this is going to happen, but I think there's a higher odds of an up month in September than most people are giving it credit for.

3:39The second I see everyone off sides, everyone agreeing with each other, something tells me maybe the other side is mispriced. So we'll see what happens, but September's up, that'll be good for all investors and your portfolio. Now, everyone knows that there are plenty of critiques of the United States of America. We ain't perfect. Are there areas for major improvement? Absolutely, without a doubt. But don't get it confused. We have constructed the single greatest economy in human history. We should be proud of that. A big reason for this stellar outcome is American capitalism. Roger Lowenstein recently wrote a great summary in the Wall Street Journal.

4:13He says that our system keeps winning on the global stage because of our unique strength and our capitalistic system, and it mirrors our political ideal. By offering opportunity to all, it fosters rigorous competition. By permitting merit to trump entrenched elites, it motivates individuals with the plumb of fortune. People ruthlessly compete with each other to be bigger, better, and more profitable. This competition is done under the promise of an economic incentive that goes to the winner in any given sector or market. There are not many incentive systems so perfectly designed that tens of millions of people wake up every single day.

4:48They try to beat each other at their chosen task. At its core, capitalism is competition, and competition creates better outcomes for everyone involved. But many times, you need capital to compete in the market. And this brings us to the incredible access to risk capital in America. But don't take my word for it, though. Jeff Bezos recently explained it perfectly to Andrew Ross Sorkin. Take a listen. Why does the United States have so much venture success? Why are the big tech companies here and not somewhere else? And there are a bunch of reasons for that. But the biggest one, eight of 10 points there, is that we have better risk capital.

5:25It's not the banking system. You know, we have a good banking system, but so does Europe. What's different here is that you can get, you can raise$50 million of seed capital to do something that only has a 10 % chance of working. That's crazy. That risk capital system that we have in this country is turning out to be very hard for other countries to do. So we have that. Now, America is not only home to capitalism and competition, it's also home to risk capital, and that allows risk takers to take risks. And now we're seeing the results of these forces come together and present themselves in a breathtaking economic boom that even the bears have to respect.

6:02All that talk from earlier in the year of recessions, Great Depressions, empty shelves, and massive job losses, it ain't never coming to fruition. In fact, the exact opposite happened. Carson Group's Ryan Dietrich writes, we were told this summer that we would see a recession in the bear market. Instead, we just had one of the best summer rallies ever in history. Looking at the 10 best summer rallies ever, the rest of the year was higher eight times. Mike Zaccardi points out that the S &P 500 is up 29 % in the last 100 trading days. It's only the sixth time that this has happened since 1950. And it's not just the public stock prices where we're seeing activity.

6:38Treasury Secretary Scott Bessent recently said, Capital markets are roaring back. Companies are taking calculated risks, spending, and pursuing deals in this economy. Since June,$1.1 trillion in M &A has been announced, including nearly$300 billion in August. It's the busiest summer since 2021. So the market's screaming one thing. It doesn't care about your feelings. It doesn't care about your ideas. It really, really doesn't care what you think was supposed to happen. The economic policies that have been put in place are encouraging risk-taking. We're watching capitalism do its thing. and it is a beauty to behold.

7:14There is no better system in the world. There are other systems, but none are as good as this one. America's capital markets are the best. Everyone wants to access our investors, our markets, and our companies. We encourage competition, we breed innovation, and we dominate other geographies in business and finance. We can always get better. And as I said earlier, we ain't perfect. But anyone running around predicting the demise of the United States economy, they're either dumb or confused, maybe both. The stock market rally over the last few months is confirmation that government policies can absolutely influence economic outcomes.

7:49Simply, we need pro-business policies in place that incentivize risk-taking. The market forces will take it from there. And if you're an investor, like many of you, that's gonna be good. It's gonna be very good for your portfolio. Before I let you go, I've got a very special treat for you. Saquon Barkley, superstar NFL running back. Everyone knows him for setting the single season record for rushing yards, and everyone has seen him win a Super Bowl and dominate on the playing field. But Saquon over the last few years has also built one of the best tech investment portfolios that I've seen. He's an investor in some of your favorite companies.

8:25And Polina Pompliano is here after spending months interviewing Saquon, his friends, people on his team, the founders in his portfolio, and those who know Saquon best. She's got exclusive details about how much money he's invested, how much he's up, and what companies he's actually put money into. This type of data is hard to find. Plena spent months going and gathering it. She's here to reveal to us. What is Saquon Barkley's investing track record? Take a listen. All right, Plena, I thought a great place to start this conversation. Saquon Barkley, obviously the best running back in the NFL. He is the record holder for most yards in a season, Super Bowl champion, but he's spending an enormous amount of time and money investing in tech startups.

9:05You spend a bunch of time with him and people around him understanding this. Why is he doing this? Well, what's interesting about Saquon is, as you know, I don't know a ton about football, but what we were noticing is that Saquon was hanging out with a lot of founders. He's hanging out with founders at dinner, at NFL training camp. He's going to their offices. And it was like, why? And I think the answer is in the piece, which is that Saquon in 2021, after he had these, you know, potentially career ending injuries, they weren't, but they could have been, he started getting more interested in investing.

9:43And the reason he got more interested in investing is because he saw consciously or not, that football is fragile, like the fragility of his position, which is the shortest, you know, shortest shelf life in the league. and also that one injury could derail your career. One franchise decision can derail your career. All these things, whereas investing can help you build permanence. And I think that he's now in a position where he's at the height of his career. He's had a really great year. And so he's capitalizing on it while still in his prime to build permanence out of fragility. So basically you're saying he's hot and he's got cash and people want him on the cap table and he's exploiting that opportunity to build that permanence that you're talking about.

10:33Exactly. And what's interesting is most athletes do what he's doing after they retire. He's doing it now. Yeah, makes sense. He also, back in the day, decided that he was going to take 100 % of his sponsorship dollars in Bitcoin. I know because I was there. And when he made that decision, he got clowned all over the Internet. All these people came out of the woodwork, sports agents, financial advisors. Everyone was telling how stupid he was. I don't remember what the price of Bitcoin was, but it wasn't over$100 ,000. So how's that going for him? Yeah, so you know firsthand when he invested in Bitcoin, because I believe he announced it on your show.

11:11and I remember how big of a deal that was because other than Russell Okung, I think he's the only other athlete who had done that. The price of Bitcoin at the time when he did it was$32 ,000. So he took$10 million of endorsement cash, which now in today's dollars, at today's price, is about$34 million. That's good. $10 million income stream and turn it into$34 million. For now, of course, crypto could crash. And it was interesting because one of those crashes did happen after he announced that he was doing this. And at the end of 2022, everybody remembers the pain, the struggle, all these companies going under.

12:01And Bitcoin ended up falling under 16 ,000, which is more than 50 % below what he invested. So it wasn't a fun time for him. He said he picked up the phone, he called Ken Katz, his business manager, and he said, what is going on? Which is the question everybody was asking themselves, like, what is going on? Ken, who is very well connected in Silicon Valley. He knows a lot of investors. He's in the Bitcoin community as well. He told him to hold on and he did. And that's why he's been able to kind of like see this through. Another interesting thing that Saquon said about Bitcoin when I was asking about volatility and risk is that he compared it to football.

12:47And the comparison is really interesting because if you think about it, if you look at these short term moments of volatility, it can be really hard mentally. but because he deals with this week after week in the NFL, he kind of understands it. So he told me like when he first became a Philadelphia Eagle, the first week, everybody was like, screw the Giants. Thank you for Saquon. He's amazing. The second week he dropped the ball and they were like, go back to New York. We don't want you here. So it was like that. It's like he compared it to the volatility of Bitcoin in terms that he could actually understand.

13:26So Ken Katz basically made sure he held now at over$100 ,000. He looks like a genius. And Ross, as you mentioned, was the first NFL player, I think first professional athlete to take his salary in Bitcoin, which was obviously a big deal. What was your takeaway about Ken? Ken is, as you mentioned, the business manager, someone that we've got to know over time. But what is your takeaway from him after doing the story? so ken katz is a very quiet character he operates behind the scenes he doesn't like giving interviews he's never been quoted in the press um i managed to get one quote out of him in my piece but he he likes to kind of like operate behind the scenes but i do think that saquon barkley isn't saquon barkley the investor without ken it's a very lean team it's just saquon ken katz and a financial advisor who acts more as an accountant and kind of is the brakes, you know, like, oh, maybe we'll invest some in the S &P 500.

14:27But basically, here's like the playbook. Here's a strategy that Saquon and Ken have now perfected at this point after investing in more than 10 startups. Ken taps his network. It's very relationship driven. So Ken goes out to his investor friends and his investor network, he asks what's hot, what's good. The more he hears from trusted people that a certain company or founder is great, they then take a very direct approach and target the founder themselves. So in my piece, I talk about this moment where Ramp's CEO Eric Gleiman looks at his phone and someone on his team goes, Saquon Barkley just emailed us about investing in our company.

15:15And he's like, wait, what? Usually these founders are the ones pitching. Usually athletes come in asking for endorsements, not equity. And Eric was like, the hottest NFL player wants to invest in our startup. And it's interesting because this like aggressive, direct to founder approach. Jack Maulers, founder and CEO of Strike, he got a similar message from Ken, and the subject line was, Saquon Barkley loves Bitcoin. And Jack Maulers was like, this is definitely a scam. What is this? Because it's unheard of, right? This very, very hands-on approach. And so once Ken reaches out to a founder, then they invite the founder to dinner with Saquon, where Saquon kind of works more of the human approach.

16:07He tries to understand what drives the founder, what the mission is. He asks questions about the business. He's very, very curious. Every founder I talk to said the same thing, which is that he asks a lot of questions. And when I asked Saquon about that, he said that he's trying to understand what kind of person it is, whether he wants to be in business with this person, whether he wants to promote their company and put his reputation on the line. So if Saquon likes it, he usually makes a commitment on the spot, like a word of mouth commitment. And then behind closed doors later, a deal is negotiated where Saquon typically writes a check between 250K to$500 ,000.

16:52dollars. So as part of this, I can confirm that Saquon is incredibly curious. He constantly is asking questions and is genuine, which I think is the most important part. He's not just asking questions, ask questions like he's intently listening, he's following up. And I think that's why so many people enjoy being around him from a business perspective. You know, it would get old to just hang out with somebody who is a celebrity or an athlete, but the conversation was hollow, right? But when you can talk with somebody who is not only intelligent, but it's very curious. I think that's a kind of a very powerful combination, which he has.

17:26His family is, I think, one, his reputation is he's very family driven. Two, you see it play out in the press and stuff when there's photos. He's constantly with his kids, with his fiance, et cetera. But did you get any insight in terms of if that is contributing or driving any of this kind of investor focus? yeah and it's it's it is his family his uh fiance and his two kids but i would like to broaden it and say it's also very much his parents and i think that um when he was younger uh there was a lot of he said financial instability in their home although he never felt it because he said he had two loving parents they gave him everything you know he never felt that financial instability But he knew he knew money was tight.

18:15They ended up getting evicted at one point when he was in middle school for eight months. He went to live with family friends. So so he saw the ramifications of that. another thing that i thought was really interesting is that his dad was a really gifted boxer and he could have had a professional career as a boxer but what happened was at some point in 1992 he like popped his shoulder and he couldn't get it fixed because he didn't have the money and it was like it wasn't by choice that he quit his passion it was by circumstance it was oh no like and he tried again and he just couldn't do it because of the pain and what it came down to was like lack of capital you cannot pursue your passion because you don't have the money and so even even if you're the best even if you're the most talented um so i think whether saquon realized that that had an effect on him or not it it might have like he saw that growing up And so then when he, Saquon got hurt in 2020, his dad told him, don't quit, go to every game, even though you have an injury, be there, you know, so he's like adamant about that.

19:32And then, and then when I asked him about his kids, when basically when I talked to Saquon, he was with his kids in the car, they were all going to an Old Spice commercial that he's filming as part of an endorsement deal. and it was interesting because he very much knows that he doesn't want to leave his kids a legacy of fragility or uncertainty. He wants to create a life of stability for them, and I think the path that he sees to do that is through ownership. Even though venture capital is risky, even though a lot of these startups could go to zero, of course, he's diversified in real estate and safer things like index funds, S &P 500, whatever.

20:19He knows that generational wealth can be found through venture investing, asymmetric risks like that. So I think Saquon basically wants to leave his kids more than just, hey, your dad was a great NFL player back in the day, he wants to leave them something that can last for many, many, many, many decades and the money can grow. Yeah, I mean, it makes sense. And look, he, I think one of my takeaways from the piece was that not only does he do the venture investing, he does have stock portfolio, the real estate and all the normal things you would expect. It's a diversified kind of, you know, a traditional portfolio, but he specifically is spending his time, his interest on, on the venture stuff.

21:06And he obviously enjoys it. and my guess is that he's going to continue to be pretty good at it as long as he keeps that curiosity going. Where can we send people to find the actual article if they want to read the entire profile? You can go to readtheprofile.com and the headline of the article is Saquon Barkley is playing for equity. Oh, that's a good headline. All right, and where can we send people to find you on the internet? At Paulina Pompliano on X. Amazing. All right, well, nice to see you. I'm sure I'll see you later today. Thank you. Do it again in the future. All right, guys. Pretty interesting to hear the actual nitty gritty details of one of the best running backs in the NFL, also having a great tech portfolio.

21:48I told you, if you watch this show, I'm going to always try to get you information that no one else has. There you go. Now you know how much Saquon's investing and how much he's up. And he also bought some Bitcoin, which is always welcomed here as well. That's it for today's show. Remember, we have 20 ,435 subscribers. That ain't enough. Trying to get to 1 million. That's my big goal. and with your help, I can do it. Make sure you subscribe and I'll see you guys live tomorrow from the desk of Anthony Pompliano.

From the publisher

"Seasonality" tells us that September is typically a down month for financial markets, but I think this  year could be different. Stocks, gold, and Bitcoin all have powerful tailwinds lining up at the same time — looming rate cuts, bad investor sentiment, and more. In this episode, I explain why history might not repeat this time, and why September could turn into a breakout month across every major asset class.


0:00 Intro

0:50 September will be an UP month

3:52 Why American capitalism WORKS

8:04 Polina Pompliano details Saquon Barkley off-the-field success in investing


Subscribe To YouTube: https://youtu.be/IxsdWibrurQ


Pomp writes a daily letter to over 265,000+ investors about business, technology, and finance. He breaks down complex topics into easy-to-understand language while sharing opinions on various aspects of each industry. You can subscribe at: 

http://pompletter.com


Join 600K+ subscribers on my main channel: https://pompyoutube.com/ 


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