The Market Has Never Peaked in June Since 1950! Here's Why It Matters!

Summary

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Podcast Summary: Earn Your Leisure – “The Market Has Never Peaked in June Since 1950! Here’s Why It Matters!”

Episode Date: June 8, 2026
Hosts: Rashad Bilal & Troy Millings
Podcast Network: iHeartPodcasts

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Episode Overview

This episode of Earn Your Leisure unpacks a fascinating piece of stock market history: the S&P 500 has never peaked in June since 1950. The hosts break down what this means for investors, how current market dynamics compare to past cycles (especially the late 1990s), the critical need for discipline and flexibility in investing, and how institutional activity shapes what’s happening under the surface. The conversation blends market facts, real-world investing strategies, and cautionary advice about “following the billionaires."

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Key Discussion Points & Insights

1. Investment Fact of the Week: The Unique History of June Market Peaks

• Statistical Insight: The S&P 500 has never recorded its annual high in June from 1950 to 2025.
• Implication: "This is a really, really great time to buy...the market never has peaked since 1950 in the middle of the year." (D, 02:38)
• Seasonal Pattern:
  • Fewer annual highs in July (3) and August (3).
  • Most peaks occur in November and December.
  • Current Context: “One of the greatest runs I think we've ever seen in tech history.”
• Call to Action: June is historically a strong buying opportunity, positioning for gains later in the year.

2. Challenging Market “Rules” and Narratives

• “Sell in May and go away”—Debunked:

  • "The sell in May and go away axiom was always dumb, and it was for institutional investors." (D, 05:40)
  • This year, Nasdaq was up 8% for the month, defying that old adage.
  • Many investors experience anxiety, uncertain if a crash is coming or if the growth is sustainable.

• Historical versus Current Tech Markets:

  • “I know '99 gets compared a lot and there are huge differences… the amount of revenue being brought in, the amount of earnings… profitability. A lot of these companies where those didn’t exist in '99.” (A, 04:20)

• Flexibility & Discipline:

  • “Have a plan, be disciplined, but also have the flexibility to adjust.” (A, 05:33)
  • Today's rules may require adaptability; the market can move in ways history doesn’t always predict.

3. Institutional Moves vs. Public Commentary

• What Experts & Billionaires Say vs. Do:

  • "Most billionaires are not going to share their strategies on what they're actually doing in real time." (D, 06:23)
  • Example: Ray Dalio warning of collapse while selling diversified portfolios worldwide.

• Exceptions:

  • Mike Novogratz as a rare figure who openly shares actionable stances (e.g., gold, Bitcoin, negative takes on XRP).
  • "He was one of the first billionaires to actually get on a broadcast and be like, yo, this…" (C, 06:56)

• Don't Take Headlines at Face Value:

  • Investors like Michael Burry or Michael Saylor might publicly state one thing while changing positions privately.
  • Example: Berkshire Hathaway “sitting on the sidelines” while investing $10B into Google for AI exposure. (A, 08:03)

4. Market Rotation & The AI Rush

• Rebalancing Explained:

  • Recent Friday close saw Nvidia declining while money rotated into other AI and semiconductor companies (Micron, Sandisk, ARM, Microsoft).
  • “If Nvidia goes from 8.8% of S&P down to 8.4..., now there's more liquidity to put it in other companies.” (A, 10:34)
  • This gives the perception that something is wrong with the leader (Nvidia), but it’s simply broadening AI exposure across more stocks.

• Sectoral Momentum:

  • Single-company news (Snowflake’s revenue) reignited momentum in entire software/AI sectors.
  • "Things are happening. It might start with one company and trigger an entire sector. So you gotta be ready and be prepared." (A, 12:26)

5. Hedge Funds vs. Individual Investors

• Business Model Differences:

  • “The hedge fund business is in the capital accumulation business. You are in the holding empires for 20 years business. They are not the same. Please do not get tricked out of your spot.” (D, 11:31)

• Key Guidance:

  • Don’t get distracted by short-term headlines or institutional moves designed to raise and move capital quickly.
  • Retail investors should focus on long-term value and not mimic every institutional rotation.

6. Notable Tangents & Humor

• Discussion on high-profile “traders”:
  • Brief, tongue-in-cheek debate over whether political figures like Trump or Nancy Pelosi count as major asset sellers. (D/A/C, 13:38–14:00)
  • Lighthearted banter about getting “insider texts” from Trump.

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Notable Quotes & Memorable Moments

• “Never in history since 1950 has the market peaked at this month [June]. Now is going to be the time to buy.”
  – D, 03:45

• “Have a plan, be disciplined, but also have the flexibility to adjust.”
  – A, 05:33

• “Most billionaires are not going to share their strategies on what they're actually doing in real time.”
  – D, 06:23

• “We're watching rules being changed. Right. You hear, guys, we just saw Michael Burry again with another proclamation… what's the track record since?”
  – A, 07:53

• “The hedge fund business is in the capital accumulation business. You are in the holding empires for 20 years business. They are not the same.”
  – D, 11:31

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Timestamps for Key Segments

• [02:32–04:03]: S&P historical June highs & implications for current investing
• [04:03–05:40]: Debunking “Sell in May”; Comparing 2020s to 1999 tech market
• [05:40–06:38]: Billionaire/institutional advice vs. actual strategies
• [06:38–07:37]: Mike Novogratz as an open billionaire and discussion on XRP
• [07:53–08:35]: Major investors say one thing, do another; Berkshire’s Google/A.I. pivot
• [09:48–11:29]: Nvidia rebalancing, institutional asset rotation explained
• [11:29–12:30]: Hedge funds vs. retail investor mindsets
• [12:30–13:12]: Software sector dominoes and why you need to stay ready
• [13:12–14:00]: Humor: “Are Trump and Pelosi trading?” – Banter on political asset moves

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Conclusion & Key Takeaways

This episode empowers listeners to avoid getting whipsawed by market noise and media narratives, emphasizing the importance of using historical patterns in context. The hosts encourage sticking to a disciplined plan—while being ready to adjust as new rules emerge in this era of rapid tech-driven change. Their parting message is to focus on long-term value building while not blindly following pundits or even billionaire investors—many of whom are “not going to share their strategies on what they're actually doing in real time.” (D, 06:23)

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For rich, timely discussion with relatable analogies and a dose of humor, this is a standout Earn Your Leisure episode for anyone tracking the rhythms (and surprises) of today’s stock market.

Transcript

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[C]

All right, let's get to it. Ladies and gentlemen, investment fact of the week.

[D]

This is a really good one. If you take the data S and P. Annual highs per month since 1950 through 2025. Do you know that never in the month of June has the market peaked in June. So this is a really, really great time to buy. Usually in July. We've only had three new highs for the year. August, we've had three. Normally in November and December is when we have the peak. So when I was going back and looking through the historical data, I thought it was very fascinating that it slows down in April and May and June. The market never has peaked since 1950 in the middle of the year. This is one of the greatest runs I think we've ever seen in tech history. We could talk about valuations and PE ratio and shilla ratio later, but what this tells me is for the second half of the year, the market is going to be on an absolute tear. And if you are afraid or if you're new, June is going to be a great opportunity to buy. Never in history since 1950 has the market peaked at this month. Now is going to be the time to buy this month. Roll into the gains for later in the year and you'll be a. Okay, see you at Invest Festival. You have a great opportunity to buy in August as well. But November and December should be absolutely amazing. That's the investment fact of the week.

[A]

Yeah, man. I guess the buy May and go away thing didn't really hold steady. No, I think Nasdaq was up 8% for the month. It's. I feel like we have these conversations more and more every week with the. I don't know if it's fair. Maybe it's anxiety of is this going to crash? What are we looking at? What are we seeing? There's no way that this could be real. How is this going to be sustainable? And every time we look, I mean, there's a new metric and I know 99 gets compared a lot and there's. There's obviously some huge differences. Number one, the amount of revenue being brought in, the amount of earnings that's being brought in, the profitability. A lot of these companies where those didn't exist in 99. I, I feel like the new rules are being made right now. Right. It just feels like if you, you have to be flexible with, with some of, of history in a sense.

[D]

Right.

[A]

As I listened to a lot of experts, I was up watching Jensen last night, just blown away, watched Tom Lee, was watching CNB all day and I'm just. They don't know what to make of what we're seeing and so remain disciplined. But as some. Sometimes you just have to make adjustments in. In the sense of, you know, where's the new entry point? A lot of times I get asked, I mean, probably four to five times a day, well, what's the entry point? When I'm like, let's see where this thing settles. Well, maybe it doesn't settle. And so now we have to be adjustable with some of our plan, but that doesn't mean we don't remain disciplined. So I think that would be my rule of the week. It would be have a plan, be disciplined, but also have the flexibility to adjust.

[D]

And I'll say this, too, the selling may go and go away. Axiom was always dumb, and it was for institutional investors. I always like to go to other business realms, right? Bob Johnson never did that with Bet. Steinbrenner. Never did it with the Yankees. Dolan never did it with New York. We have to make sure, because a lot of times in media, people will give you advice on what to do and do the complete opposite. For example, like if you take Ray Dalio in Bridgewater, one of the greatest firms of all time, even now, through Principles and Changing World Order, he's telling you about an imminent collapse, right? And he did this in the 80s and the 90s and early 2000s while selling a diversified portfolio strategy to every continent on Earth. Please be mindful of the information that you're giving on public airwaves, because most billionaires are not going to share their strategies on what they're actually doing in real time.

[C]

Well, you know, what billionaire actually did share his strategy was Mike Novogratz. And that was somebody that we've had on market. And then when we went on his podcast and he was saying about gold, and after that goal went up like 70%, he talked about Bitcoin when it was, you know, at a low point, a variety of different things. He actually was talking. He was talking bad about XRP during the pandemic. And I think they. We actually, they was like, yo, can y' all cut that part out? Because then XRP ended up in the dumpster. But he was the. He was one of the first billionaires to actually get on a broadcast and be like, yo, this. No. And then everybody in the comments was like, oh, he's trying to derail you. He don't listen to him. He's trying to sabotage your portfolio, make sure you buy it. And we've seen what happened to XRP ever since.

[A]

Yeah, we're seeing.

[C]

But. But I do say that to say, Mike Novogratz will be at Invest Fest. Get your tickets to Invest Fest. Absolutely.

[D]

One of my favorite investors for sure.

[C]

One of the few billionaires that will have an Invest Fest.

[A]

Stay tuned, stay tuned to learn has been issued. I was going to say like we're watching rules being changed. Right. When you hear, guys, we just saw Michael Burry again with another proclamation. Right. Tesla's numbers are fake. Nvidia's numbers are fake. Okay, you were right. In 2008, how many? What's the track record since we just saw Berkshire Hathaway who said they would be sitting on the sideline, just invest $10 billion into Google under new leadership three weeks ago. Hey, the valuations are too elevated. We're going to wait. We're going to sit this out. We got a $400 billion treasure chest today. They allocated 10 billion into Google because of the AI demand. Right?

[D]

We're seeing this.

[A]

We saw Michael Sellers said he would never

[D]

sell his Bitcoin. And here y' all kill me tonight. I want an apology.

[A]

You would never sell his Bitcoin.

[D]

Yep.

[A]

Lo and behold, he has now sold bitcoin.

[D]

Now you're starting to sell off and some of the derivative, derivative products that you made as a result to raise cash and da, da, I get it. I'm not going because I've told in stock club. Let me get some pandas in chat. The issues that he faced taken on those institutions, right, so they can suppress the market long enough to cause uncomfortability for you, to make you reverse your course and to embarrass you publicly. And to your point, like you said, most funds are not going to tell you their book of business on air for their competition to derail them. They're oftentimes going to tell you the exact opposite of what they're doing. And that's why it's really important to go through the filings. Even with Berkshire, even though they have a bunch of cash on hand, they're under new leadership. He wants to get out of Buffett's shadow and he's going to do so through tech.

[A]

It's evident. And it goes back to that idea of just being able to adjust. I'm not sure if everybody was witnessing this live, but Friday during trading around 323 or tweet went out and we'll talk about that later with Nvidia and ARM and Microsoft. And at 3:30 you start to see the companies running, broadcast running, Microns running, Sandisk is running. You see all these companies running. But the one company that was kind of falling down was Nvidia. And it talks about being adjustable. Why is Nvidia falling down? Well, here comes a rebalancing act. The act that you never get to see, you just get to feel a part of. Right. Well, why would they rebalance out of Nvidia, this company that is going to be leading the AI dominance for the next five to 10 years, if not longer? Well, if you look at the largest allocation, S and P, when people see opportunity and they want to have liquidity, they're going to try to find liquidity from their largest holding. And their largest holding, S and P is way to 8%. So let's rebalance, let's take some money off the table there and let's start spreading it into other companies as well. What does that mean? That means there's a broad exposure to AI. Not only are we seeing, institutions are seeing it. And so if Nvidia goes from 8.8% of S&P down to 8.4, still the largest allocation, but now there's more liquidity to put it in other companies. And we kind of saw that happening at the end, like literally at the end of the day on Friday. If you look at the charts from about 3:30 to 4, you saw a drastic climb up in a lot of companies that was happening. But if the average person is watching it, it's like, oh my gosh, is it over? And then here we go. Obviously Justin spoke yesterday and here we are with Nvidia climbing back up over $13.

[D]

They're every. Yeah. If I can say this last point too, please write this down. The hedge fund business is in the capital accumulation business. You are in the holding empires for 20 years business. They're two totally different things. To everyone who kept asking me, well, what's up with Microsoft and is it going to. The rotation affected them and everyone who killed every software stock. And some were valuable, some were not. But you have to realize AI is a software as well. That's the interesting part now. So now Microsoft is starting to make a move and everyone's like, okay, it's coming back from the dead. That company is too valuable to go anywhere. But the hedge funds are in the capital accumulation, asset under management business. You are in the hold companies and things that are valuable for a very long time business. They are not the same. Please do not get tricked out of your spot.

[A]

Yeah, another, another prime example of the market adjusting. And I think Snowflake became a trigger for that. Right. Snowflake becomes a software company. When we're talking about that five layer kick again, application software. Snowflake shows revenue growth. Okay? That means that this sector actually has something. And so you watch Snowflake, you watch ServiceNow, you watch Microsoft, that was caught inside of that. You watch the IG ETF start to move up. It starts hitting those, those moving averages where it shows growth. That trend line starts to move. And now you see momentum going in. And so things are happening. And it might start with one company and trigger an entire sector. So you got to be ready and be prepared.

[D]

Can I ask you guys a question real quick?

[C]

I forgot to mention that at the beginning.

[A]

Welcome back.

[D]

Congrats. Welcome back. Speaking of which, is there any person that you know that is above $100 million that's sold out of any asset that you know of less than two years?

[A]

100. No, not 100.

[D]

See, even that, that's telling. Go, go ahead, Rashad. I just want to make the last little point.

[C]

Yeah, well, well, it depends on how you define selling out of an asset because Trump has been trading like a maniac. Nancy Pelosi, she's been traded like a maniac.

[D]

You know, Trump, we not doing that.

[A]

I don't know.

[D]

Fake news.

[A]

I seen him, I seen him. Well, do you?

[C]

Okay, No, I don't know, Trump.

[D]

I was like, damn, I, I didn't get that text. My boy

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