Why Wealthy Investors Refuse to Sell Their Tech Stocks

Summary

Podcast Summary: "Why Wealthy Investors Refuse to Sell Their Tech Stocks"

Podcast: Earn Your Leisure
Hosts: Rashad Bilal & Troy Millings (iHeartPodcasts)
Date: May 9, 2026

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Episode Overview

In this episode, the hosts dive deep into the ongoing debate about whether now—with stock markets near all-time highs—is the right time to sell tech stocks. Drawing on insights from prominent investors, events like the Milken Institute and Davos, and recent market performance, they break down why top investors are holding (not selling) tech and AI-related stocks despite widespread advice to “sell in May and go away.”

The conversation blends practical market analysis with personal experience, offering listeners insight into the mindset and strategy of wealthy and institutional investors, as well as current market cycles, spending trends, and the role of media narratives in driving investor behavior.

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Key Discussion Points & Insights

1. Should Investors Sell at All-Time Highs? (02:05–04:34)

• Media & Market Timing Myths:
  The hosts debate the popular saying, “Sell in May and walk away,” and whether it applies in 2026.

  • Investor 1: “Is it time to walk away? Exit stage left?” (02:19)
  • Investor 2: Pushes back, quoting economist Gary Shilling's warning about possible declines but noting that wealthy investors hold, not sell.

• What the Wealthy Do:
  At exclusive events (like Davos), industry insiders don’t discuss selling major holdings in private.

  • Investor 2: “No wealthy investor...is telling you to get rid of the entire landscape of investing... The only people who tell you to sell are those who want you to be broke.” (03:09)

• Tech & AI Growth Still Driving Markets:
  Tech giants are still growing (e.g., “Anthropic is doing 30 billion a year…”), companies like Nvidia, Samsung, Meta “on a tear,” and cash-rich moguls (Warren Buffett, Greg Abel) are waiting for prime opportunities rather than selling at highs.

  • Investor 2: “This is a great accumulation time... Hold for the long term.” (04:27)

2. Market Fundamentals: Why the Tech Narrative Hasn’t Changed (04:34–06:59)

• The ‘Story’ of AI and Tech:

  • Investor 3: “Has the AI story changed? ...We saw the biggest companies in the world report last week... Has the capex spend gone down? No. That means they’re still investing into the technology.” (04:34–05:04)
  • Capex spend is consistent = companies continue to invest billions into tech infrastructure.

• Earnings & Consumer Strength:

  • Companies beat earnings yet pull back because of future investment in infrastructure.
  • Investor 3: “Has consumer spending gone down? ...If you look at Visa’s report...No. ...The resiliency is there.” (05:31–05:47)

• Macro Timing Cues:
  New Fed Chair expected in May—historically leads to short-term volatility but not a reason to exit.

  • “When a new Fed chair steps in...usually there’s a triple down inside the market. That hasn’t happened yet, but it will at some point in May...But I think after that...Nvidia reports on the 20th. That’ll be a key.” (05:51–06:16)
  • Seasonal Patterns: After May jitters, July often strong; warning that August-October tend to see profit-taking.

3. Stock Market Pundits & Hyperbolic Predictions (06:59–09:25)

• Critique of Famous Market Calls:
  Hosts discuss Tom Lee’s bullish market and crypto predictions.

  • Investor 1: “[Tom Lee] just says numbers...Bitcoin is going to be 200,000 by July and it turns into...90,000. ‘Oh, I overshot it.’” (08:35–08:49)
  • Investor 2: “All of them make those rounds and make those dumbass proclamations because they’re trying to raise funds...But being a permeable in tech is the right position to be in.” (07:49–08:12)

• Expectations for the Next Cycle:
  Lee’s prediction: after a few tough months, markets might go on “the greatest run that we’ve ever seen in human history.”

  • Investor 3: “His next thing is that after we go through some turmoil here...we’re going to go on the greatest run that we’ve ever seen...” (08:57–09:17)
  • Hosts agree some projections are exaggerations meant to draw attention and capital.

• Skepticism Around Crypto Narratives:

  • Investor 2: “To everybody who had .eth in your Twitter bios and IG a couple years ago, what the fuck is going on with Ethereum and where’s Vitalik?” (09:38)

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Notable Quotes & Memorable Moments

• Investor 2 (03:09):
  "The only people who tell you to sell are those who want you to be broke. No wealthy investor or any investor who's any good is telling you to get rid of the entire landscape of investing."

• Investor 3 (05:04):
  "That means they're still investing into the technology...if they're spending the money, that means they're spending with companies. That means there's companies that are going to take in that revenue. That's why I said the story hasn't changed."

• Investor 3 (05:47):
  "You're still seeing spending. And so that tells you that. I'll put in quotations. The resiliency is there."

• Investor 2 (07:51):
  "Can we be honest? All of them make those rounds and make those dumbass proclamations because they're trying to raise funds...But being a permeable in tech is the right position to be in."

• Investor 1 (08:35):
  "Is it overshooting or you just say anything? Bitcoin is going to be 200,000 by July and it turns into...90,000. 'Oh, I overshot it.' That's gross."

• Investor 2 (09:38):
  "To everybody who had .eth in your Twitter bios and IG a couple years ago, what the fuck is going on with Ethereum and where’s Vitalik?"

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Key Timestamps

• 02:05–04:34: Should you sell at all-time highs? Insights from wealthy investors, AI companies surging.
• 04:34–06:59: The AI investment story, corporate capex, consumer resilience, and macroeconomic timing.
• 06:59–09:25: Market punditry, bold predictions, and playful skepticism on crypto hype.

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Tone & Language

The conversation is spirited, dynamic, and candid, blending high-level financial insights with pop culture and humor. The hosts use plain language but don’t shy from strong opinions or colorful commentary (“What the fuck is going on with Ethereum?”), making it accessible and engaging for both beginners and advanced listeners.

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Conclusion

The episode reinforces a long-term, value-driven approach to investing—especially in tech and AI. Despite media narratives advising to “sell high,” wealthy and sophisticated investors are holding and even accumulating, seeing current volatility as an opportunity rather than a threat. The panel dissects market cycles, pokes fun at overly bullish forecasts, and emphasizes the importance of sticking to fundamental trends and staying resilient through short-term noise.

If you’re considering selling your tech stocks, this episode makes a strong case for holding—and listening to what the wealthiest, most successful investors are actually doing behind closed doors.

Transcript

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[Investor 1]

Is it. Is it time to sell? I know after that, right? So is it time to sell the stocks? Because they say something like selling may walk away.

[Investor 2]

Yeah.

[Investor 1]

So being. Being that stocks are currently right now at its all time high across the board for the most part, is it time to walk away? Exit stage left?

[Investor 2]

No, I know Gary Shilling said amazing economists that the market could fall 30% per year. When I was watching the conversation at Milken Institute, right The one thing I noticed is that when and you guys have been to Davos and the conversations that I've had and ascertained they only most people only tell you about selling when it's media time. Privately has Robert Smith, like when he tried to sell you the agent, did he ever say, man, I'm about to get rid of Vista Equity. It doesn't happen. Put this in chat. The only people who tell you to sell are those who want you to be broke. No wealthy investor or any investor who's any good is telling you to get rid of the entire landscape of investing. You have Agentic that is still untapped. Anthropic is doing 30 billion a year. For those who don't know, that is a gigantic number. They haven't even went public yet. Samsung's on a tear. Nvidia's on a tear. Lily is about to go on a tear. Meta is on the verge of having a turnaround. So all the people who are the wealthiest people on the planet, even we could talk about Greg Abel and Warren Buffett in a little. They have billions of dollars of cash waiting for the right time to buy. No, I know the axiom of selling May and go away. This is a great accumulation time. So should the market tick down in May? Yes, but we just left one of the greatest months in the history of investing like this. This past month was comparable for everybody's like, yo, we missed 2020. Last month was your version of 2020. And for those of you who took advantage of it, like even for the screenshot, 400,000 of that 1.6 was ran up last month. So no, all for the long term. May, June, August will be tough that it's time to accumulate whole for the long term.

[Investor 3]

Yeah, I think I don't sell here. I think if you, if you look at the story and maybe that may sound confusing, like, well, what's the story? Well, when I say the story, has the AI story changed? And again, it has. Well, how do we know? We saw the biggest companies in the world report last week and there's a couple of things you got to listen for. Has the capex spend gone down? No. Okay.

[Investor 2]

That means they're still investing into the technology.

[Investor 3]

That means they're spending it. And if they're spending the money, that means they're spending with companies. Right. I know it sounds like, oh, it's just bypassing, hey, they're going to spend 72 billion. Well, that 72 billion is being allocated somewhere. That means there's companies that are going to take in that revenue. That's why I said the story hasn't changed. Right. So memory obviously is at the forefront of that. And we'll talk about some other infrastructure plays inside of AI that you should be having on your radar. But that's not. That hasn't changed. Has the earnings from these huge mega cap companies, has that changed? Have they beat earnings quarter after quarter? We keep seeing the same thing, but they pull back because of the capex, man. Okay, that's the same theme. But what about the consumer? Has consumer spending gone down? Well, if you look at Visa's report last week. No. If you talk to JP's report, not really. If you look at TJ Maxx, if you look at Hilton in the hotel, you're still seeing spending. And so that tells you that. I'll put in quotations. The resiliency is there. Now something is happening in May. Obviously we're going to get a new Fed chair. If you look historically, when a new Fed chair steps in to his seat or her seat hasn't happened, that usually is a triple down inside the market. That hasn't happened yet, but it will at some point in May and so will be a pullback. Yeah, for. But I think after that, and I heard Tom Lee saying it as well. Nvidia. Nvidia reports on the 20th. That'll be a key. And then let's see what that momentum does going into June. July has, I mean, if you look at historically, July has been a pretty good month. August, September is when we start saying, okay, let's make sure we have reserves. We're going to start seeing profit taking, we're going to see some, some downturn. Those three months are always in that space. August, September, October, and then it's, it's back to the cycle of November to April again.

[Investor 1]

Tom Levy, He says anything, though that's not true.

[Investor 2]

We're not gonna do.

[Investor 3]

No, no, no, no, no, no, no. He's intelligent.

[Investor 2]

We're not doing that now.

[Investor 3]

Something we could argue, some of the takes are grand. He does have grand takes. But if you look at the past, definitely the past five years he's been on point man like him and Dan Ives, I know that. And they're super bulls.

[Investor 1]

I like Tom Lee. He says anything about crypto, bitcoin. He's, he's been all over the place. He has a variety. He has a habit.

[Investor 2]

He has a prior crypto fund, though, before that.

[Investor 1]

All right, let's focus on crypto because that's what he's focused on. That's what he says a lot. He talks a lot about crypto. Yeah, but he says bitcoin is going to be 180,000 by the end of the year. Last year okay.

[Investor 3]

In bitcoin, I may give you that. In the.

[Investor 2]

With the S, I mean, can we be honest? All of them make those rounds and make those dumbass proclamations because they're trying to raise funds.

[Investor 3]

Market movers.

[Investor 2]

Kathy did it, he did it, sailor. Allegedly. They're doing it to drum up interest, to sell a narrative that isn't going to come true in a time frame that they're talking about. But being a permeable in tech is the right position to be in. Back to you, that part.

[Investor 3]

Yeah, I would say that part because the tech piece where he's seen the S and P, a lot of it I agree with. Yes. Some of it is very grand. And that's been the continuous theme. It's almost like I'm going to overshoot so that even if it falls a little bit under that, hey, I told you, right?

[Investor 2]

So what don't you like about us? Takes your shot.

[Investor 1]

I like him. I think he's extremely intelligent person. But you. Is it overshooting or you just say anything? Bitcoin is going to be 200,000 by July and it turns into. It's 90,000. Oh, I overshot it.

[Investor 3]

That's gross.

[Investor 1]

S and P is going to be 10,000. Like he's just saying. Just numbers. Like he. But the number, they're not even close. He's done this with crypto quite some time. He's done.

[Investor 3]

He's done the numbers specifically because he's been pretty spot on with the S P. Now, his next. His next thing is that after we go through some turmoil here in the next few months, we're going to go on the greatest run that we've ever seen in human history. Like he literally has said that. Will that happen? We.

[Investor 2]

That's the overshoot too. That's overshoot.

[Investor 3]

We shall see.

[Investor 2]

Okay, that's an overshoot. Yeah, yeah. I like Tom a lot though.

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[Investor 1]

He's a good guy. I think he's intelligent. I think he's extremely intelligent person. I just think, like I said, he just has very outlined. Yeah, he's just putting these numbers out there.

[Investor 2]

And to everybody, I'm not shooting at anybody in particular, but to Everybody who had to.eth in your Twitter bios and IG a couple years ago, what the fuck is going on with Ethereum and where's Vitalik?

[Investor 3]

Quiet. Stand low.

[Investor 2]

Mm.

[Investor 3]

Stand low.

[Investor 2]

Just a question.

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