End of an Era? Is Tim Cook Leaving Apple?

15 Oct 2025 · 15 min

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Earn Your Leisure Podcast - Episode Summary

Episode Title

End of an Era? Is Tim Cook Leaving Apple?

Hosts

  • Rashad Bilal
  • Ian Dunlap

Episode Overview

In this episode of the Earn Your Leisure Podcast, Rashad Bilal and Ian Dunlap discuss the rumors surrounding Tim Cook's potential resignation from Apple and the implications for the tech giant's future amid increasing competition, particularly in the realm of artificial intelligence (AI). The conversation also explores broader market trends, investment strategies, and the future direction of major tech companies.

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Key Discussion Points

  1. Tim Cook's Leadership and Speculation of Resignation
  2. Current Status: Rumors suggest Tim Cook may leave his position at Apple.
  3. Perspective:
  4. Ian Dunlap expresses skepticism about Cook being fired but acknowledges the intense pressures he faces, particularly in competing in the AI arena.
  5. The discussion touches on internal company battles and geopolitical challenges that could lead to Cook's resignation.
  1. Apple’s Position in the Market
  2. Market Competition:
  3. Apple is seen as losing its former dominance, with companies like NVIDIA, Google, and Amazon making significant advancements.
  4. Ian remains optimistic about holding Apple stock through 2034, despite acknowledging concerns over succession planning and limitations on acquiring strategic partnerships (e.g., OpenAI).
  1. Insights on Investment Strategies
  2. Current Portfolio Recommendations:
  3. Both hosts discuss the importance of maintaining a diversified portfolio, including potential investments in small and mid-cap stocks.
  4. Ian provides actionable advice, such as tracking margin prices of crypto futures to assess institutional sentiment.
  1. The Evolution of Investment Strategies
  2. 60/40 Portfolio Debate:
  3. Ian argues that the traditional 60/40 stocks-bonds portfolio may be outdated and emphasizes the importance of alternative assets in modern investment strategies.
  4. Preparing for Market Pullbacks:
  5. Discussion on how market crashes can present generational opportunities for investors who are prepared.
  1. Market Trends and Future Predictions
  2. Geopolitical Pressures: The hosts analyze the impact of geopolitical tensions on major companies like Apple.
  3. Innovative Edge of Competitors:
  4. Amazon’s investments in data centers and partnerships are highlighted as signs of its innovative potential.
  1. Specific Stock Recommendations
  2. Small and Mid-Cap Stocks:
  3. Highlights of stocks like RGTI, which have shown significant gains recently.
  4. Strategic Trading Advice:
  5. Recommendations for taking profits from small caps and reallocating funds into larger, more stable companies for long-term security.

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Key Takeaways

  • Future of Tim Cook: While there are concerns about his leadership and potential resignation, Cook continues to have the support of investors for the time being.
  • Investment Philosophy: Staying informed on market trends, assessing the competition, and being prepared for market fluctuations are crucial for successful investing.
  • Market Adaptation: Investors should adapt to changing market conditions and consider alternative assets as part of their strategies.

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Closing Remarks The episode provides a critical analysis of not just Apple’s current situation but also offers valuable insights into investment strategies tailored for navigating the modern financial landscape. Listeners are encouraged to engage with the discussion and apply the practical advice shared throughout the episode.

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*For more insights, don't forget to like, comment, and subscribe for future episodes of Market Mondays!*

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Transcript

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0:00This is an iHeart Podcast. Guaranteed Human.

0:31a.k.a. Neuro Linguistic Programming. Is it a self-help miracle? A shady hypnosis scam? Or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike Della Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release. If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike Delaroach on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.

1:14This is Dr. Jesse Mills, host of the Mailroom Podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward. Our two-part conversation is available now. Listen to The Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows.

1:46Hey, it's Joel. And Matt. From How To Money. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence. Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This episode is brought to you by PNC Bank.

2:21A lot of people think podcasts about work are boring. And sure, they definitely can be. But understanding a professional's routine shows us how they achieve their success little by little, day after day. It's like banking with PNC Bank. It might seem boring to save, plan, and make calculated decisions with your bank. But keeping your money boring is what helps you live a more happily fulfilled life. PNC Bank, brilliantly boring since 1865. Brilliantly boring since 1865 is a service mark of the PNC Financial Service Group, Inc. PNC Bank, National Association member, FDIC. Tim Cook, there's some speculation that he may be replaced.

3:05But is it? Okay, so first let's talk about that. And then let's talk about Apple as a whole because Chad GBT is still bullish on Apple. Yo, congrats to you for making that headline, Ian. Thank you. Okay. So, yeah, let's talk about the first thing. You think that Tim Cook is really going to get fired? I don't. Okay, even in that. So let's take the sensationalism out of it because even though I brought up that he should be replaced. I said he should go to chairman. If he's considering stepping down, and once again, I've been saying the last four weeks and I'll continue. Tim Cook, Timothy D. Cook, I sincerely apologize because I did not know the fight you were fighting that was stopping you from getting to the AI that you needed.

3:52If he's stepping down as the ruler of one of the most powerful tech companies of all time, what would make you step down? so you can either elect to be removed from the seat by your own volition or there may be some forces that may want to get you fired michael jordan despite what he wants to come back and play for seven there was some other forces that didn't allow it to happen tom brady wanted to keep playing for the patriots but then there's bigger forces in that program upstairs that will allow you to not continue to go forward i will leave it at that i'll let aaron ross andrew ross or can tell that story in three or four years now you're rushing for succession planning so if they're being blocked shout out to everyone at hq at apple if you're being gently blocked from acquiring the llm to give you a lead advantage and timing because they have the cash on hand And I keep saying it.

4:52Microsoft's partnership idea was supposed to be Apple's just like Stargate was supposed to be Microsoft's. So but different regimes come into place and now different people get selected for different positions to do certain things. Stargate, this will go to Larry. Microsoft, you still have open air. We're going to find other ways for you guys to work together. I think he's been thwarted from what I was told from acquiring an LLM and giving some of the geopolitical stuff. He is considering resignation in lieu of those issues. How will the stock perform? The stock will still be OK. I haven't removed it out of two tech, two index.

5:35And I probably want it to 2034. Don't love the successor that he has in place, but. He will be a good executive. I care more about the operation side and how many other things that they will be thwarted from investing in. Once again, they have the cash on hand to do the deal with OpenAI. They were blocked from doing it. So the stock will be fine. I do think Tim Cook will step down in the next year and a half, two years. But the timing of when he leaves is going to matter. You just can't up and leave because you're upset. That's not how big business works. It never has worked that way. Never has worked that way.

6:10So they need a clear succession plan just for his own safety because of how important that company is. And geopolitically, you can't just have upheaval in a publicly traded company, which then may look my presidency. Look, that doesn't work that way. But what do I know? I was just the person that said he should step down. If I made you money, please put yes in chat.

6:40we still got apple is still part of the portfolio it's not going anywhere um will it be you know i think we're looking at it from the standpoint of like this was the leader of of all the companies this was the market mover and we have literally watched it get passed as a market mover right The way we talk about NVIDIA and how it's moved and it's an innovation and how it's vital to the future, we looked at this company the same way. So I guess there's a bit of, I don't know if we want to call it disappointment, but it's a bit of like, hey, what's happening? What's the next thing? How are we going to be a player in this race going forward?

7:21Because you can see it. Even if you look at the market caps of the companies that are catching up to it. Yeah, I mean, Google's right there. Google's right there. uh amazon somebody just asked me if i'm still big on amazon of course i'm i'm always be big on amazon you don't have to ask that question it it's having its own consolidation i was looking at the charts it opened the year at 227 and it's here now at 219 with all of the run that ai and technology has had it still has been kind of just sitting there so the way we talk about Apple, I mean, Amazon could be in this category, but we understand where it's headed in terms of innovation.

8:05When we talked about data centers, we saw them do that. When it was time for them to invest in a company, we saw them give a billion dollars to Anthropic and Claude. They're part of it. We just haven't seen the same type of situation with Apple. They'll still be top seven. and also to the audience who's listening. I want you to stop taking my amazing analysis and turning it into a clipped up piece that I hate something when I'm giving you detailed analysis. Other entrepreneurs have went through this. Mark Zuckerberg went through this with Litecoin. People forget in terms of the adoption of crypto into a company on balance sheet.

8:52after Jack. Oh, Mark was one of the first ones was fighting for it. What was it? It was called Libra. What was it called? Libra. And it got blocked. That was an acquisition of TikTok. What do you think about XRP? I think it's a great asset. My stance on that has not changed. I think they may be forced. Oh, you know what? Also, too, a good way to tell how well the asset is going to do and what the institutions have planned for it is to look at the margin price of the future. I'm glad you brought the server shot for one contract on the features market. Charles Schwab is$231 ,000 for one Bitcoin feature that you can hold for 30 days.

9:36Um, if you look at Ethereum,$105 ,000 and$798 for one contract, historically the vix was the most priciest asset and i think that's at around 19 000 but if you want to know how well an asset is going to do look at the margin price of the future the homework assignment for the night is when xrp futures are available to be traded on the futures market what is the margin price supposed to be so that's a quick little gym lesson yeah back to the homework assignments got to get back to the homework. Dow is $17 ,000. NASDAQ is$35 ,000 per contract if you're swing trading it. But once again, Bitcoin is$231 ,000.

10:28That's some change for every contract. Crude is$10 ,000 in comparison. So that will tell you not only the validity, but what the institutions believe that the prices will do long term. Homework. Back to the old format. homework assignment but the voiceover play ain't that great jeff jared let's get back to it and then y 'all let everybody white come on cnbc but go tim cook you probably replaced my job come on bro come on bro yeah kudos to tim i didn't know what battle you're fighting though that's that and that's a hell of a fight to have to deal with yeah I'll add to that homework assignment.

11:12Go listen to what Larry Fink said about retirement planning and what he wants to now put inside of retirement plans. And it's interesting if they are looking to add those assets in, it tells you about the state of the dollar and the state of the job market. Because the 64, I've been saying this, 60-40 portfolio, stocks and bonds are dead. They're dying. um if you have to put those other alternative assets in it will tell you that the quality of the main assets are decaying rapidly yeah and it's also telling you that they're investing in their their clients so that are looking at like how do we get exposure and if you don't give us exposure somebody else will yep what about small and um mid-cap stocks do your research and invest what you love i i know um shout out to those of you who were in rgti killing today oh yeah it's smoking i gotta just speak on rgti because when we talked about quantum people they still ask me about this yes i brought up rgti because again i like the things that encompass the entire space i'm not i don't have any quantum stocks i just don't have them yet yeah i'm not mad at anybody that's making money doing that at all congratulations my focus is just in a different area right now but congrats rgti is doing great i know i own and q is doing great the blueprint is to take if treated the same way you would a trade in the futures market or options after you have a big run-up in small caps get 200 300 400 return take half of that money and put it into a larger cap.

13:00Because my only fear is some people holding through for an even bigger gain, a thousand percent gainer, and they don't get it. Or you miss out on some safety and other assets. Like the name of the game is to get a really explosive win like that and then park it to somewhere where you don't have to think about. if you're constantly asking someone else what do you think the investment is going to do at some point you know it's going to have a deep pullback i'd never worry about microsoft apple and video never there's nothing to even freak out about even when friday was happening i'm like i should have recovered 14 days in maximum it'll be fine so if you've hit a big win in mid-cap stocks that are popular, take half of that money and put it into a company that is going to dominate through the next five or six years.

13:56And someone else earlier asked, okay, well, should we go all cash for 27? No. Buy the deeper dips. Preset your orders for 40 % off, 50 % off for where we are now. Trade your way through it if you're a trader, but wait for those big pullbacks because those, No one ever says it, but the crashes that come are the liquidity events and generational wealth events that you pray for. You pray for those moments. Brexit, the night of the election for Trump, first time. We all say it. Oh, man, I can't wait for an event like that to happen. April. Yeah, it happens. It happens. You have to be prepared and take advantage of it.

14:40Got to be prepared. Yeah. Congrats to y 'all. This is no hate, no shade. Congrats to everybody that has made money trading quantum stocks. Even in Palantir, like geopolitically and morally, I don't love it. But if you made a bunch of money in Palantir the last two or three years, okay, great. Take some of the money and put it all into Microsoft so you don't have to worry. Or OpenAI when that's public. Or NVIDIA. Or ABGO. or any of the top 20 Google that are going to overperform and overindex incredibly well. The pound is nearly at a half a trillion, which is pretty quick. I mean, that's pretty quick.

15:18I think it's at 410, 415 right now, market go. Pretty impressive. Yep. Yeah. Pray for Tim Cook, though. Tim Cook? That's a tough fight. that's a tough fight to lead an organization a nation that big and then have so many geopolitical issues that are stopping you not only from making your company better but then also be in opposition with the leadership that you're having to do business with that's what I'll tell some of y 'all there's a sweet spot in getting rich if you overshoot that number y 'all you got a whole bunch of other headaches that come with their life I want to be a billionaire I don't know if you can deal with what comes with all that Ernest what's up you ever walk into a small business and everything just works like the checkout is fast the receipts are digital tipping is a breeze and you're out the door before the line even builds odds are they're using square we love supporting businesses that run on square because it just feels seamless whether it's a local coffee shop a vendor at a pop-up market or even one of our merch partners square makes it easy for them to take payments manage inventory and run their business with confidence all from one simple system.

16:32One of the things we love most is seeing neighborhood businesses level up. There's this West Indian spot right in our community that started with a small takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even started catering events across the city. That's the kind of growth that inspires us and it's powered by Square. Square is built for all types of businesses from the corner bagel shop that turned into a local chain, to the specialty market with thousands of unique items, to the stylist who's been holding you down for years. If you're a business owner or even just thinking about launching something soon, Square is hands down one of the best tools out there to help you start, run, and grow.

17:14It's not just about payments. It's about giving you time back so you can focus on what matters most. Ready to see how Square can transform your business? Visit square.com backslash go backslash E-Y-L to learn more. That's square.com backslash go backslash E-Y-L. Don't wait. Don't hesitate. Let Square handle the back end so you can keep pushing your vision forward. What if mind control is real? If you could control the behavior of anybody around you, what kind of life would you have? Can you hypnotically persuade someone to buy a car? When you look at your car, you're going to become overwhelmed with such good feelings.

17:51Can you hypnotize someone into sleeping with you? I gave her some suggestions to be sexually aroused. Can you get someone to join your cult? NLP was used on me to access my subconscious. Mind Games, a new podcast exploring NLP, aka neurolinguistic programming. Is it a self-help miracle, a shady hypnosis scam, or both? Listen to Mind Games on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. A new year doesn't ask us to become someone new. It invites us back home to ourselves. I'm Mike De La Rocha, host of Sacred Lessons, a space for men to pause, reflect, and heal. This year, we're talking honestly about mental health, relationships, and the patterns we're ready to release.

18:35If you're looking for clarity, connection, and healthier ways to show up in your life, Sacred Lessons is here for you. Listen to Sacred Lessons with Mike De La Rocha on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is Dr. Jesse Mills, host of the Mailroom podcast. Each January, men promise to get stronger, work harder, and fix what's broken. But what if the real work isn't physical at all? I sat down with psychologist Dr. Steve Poulter to unpack shame, anxiety, and the emotional pain men were never taught how to name. Part of the way through the valley of despair is realizing this has happened, and you have to make a choice whether you're going to stay in it or move forward.

19:12Our two-part conversation is available now. Listen to the Mailroom on the iHeartRadio app, Apple Podcasts, or wherever you get your favorite shows. Hey, it's Joel and Matt from HowToMoney. If your New Year's resolution is to finally get your finances in shape, we've got your back. Prices, they're still high, and the economy is all over the place. But 2026 is the year for you to get intentional and make real progress. That's right. Each week, we break down what's happening with your money, the most important issues to focus on, and the small moves that make a big difference. Kick off the year with confidence.

19:45Listen to How to Money on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. This is an iHeart Podcast. Guaranteed human.

From the publisher

In this thought-provoking Market Mondays clip, Ian Dunlap and Rashad Bilal break down the latest buzz surrounding Apple’s leadership and the tech giant’s place in the innovation race. Is Tim Cook really on the way out? Why are there rumors about his resignation, and what does it mean for Apple’s future? Ian shares his insights on the internal battles Cook might be fighting, particularly when it comes to Apple’s struggles in the AI arms race and geopolitical blockades affecting its strategy. The duo also gets candid about the wider market, touching on Apple’s competition, including Google, Amazon, and Microsoft’s game-changing moves with AI. What do these shifts mean for investors, and is Apple still a must-have in your portfolio? Ian remains bullish, explaining why he’s holding Apple until at least 2034, but he doesn’t shy away from expressing concerns about succession planning and blocking of key deals like OpenAI. Rashad discusses market leadership changes and the lingering question: What is Apple’s next big move? Meanwhile, the conversation widens to Amazon’s strategy, data centers, and why Rashad is still a believer in Amazon’s innovative edge. There’s also a breakdown of small and mid cap stocks, with shout-outs to quantum stock winners like RGTI and insights on how to trade these explosive gains for long-term wealth. Ian gives practical homework for viewers, like tracking margin prices of crypto futures as a gauge for institutional sentiment—a lesson you don’t want to miss. Plus, find out why the old 60/40 portfolio might be dead, the importance of alternative assets, and why crashes offer generational opportunities for those prepared. Ian and Rashad keep it real about taking profits, rotating winnings into blue-chip names, and how to prepare for the next market pullback. This clip is packed with actionable advice, straight talk, congratulatory moments for winning trades, and a look at the geopolitical pressures facing the world’s biggest companies—especially Apple. If you want a sharp, no-hype analysis of markets, leadership, and how to position yourself for the future, tune in now! *Don’t forget to like, comment, and subscribe for more Market Mondays insight!* --- *#MarketMondays #Apple #TimCook #Investing #Stocks #TechStocks #AI #Amazon #Google #Nvidia #QuantumStocks #FinancialEducation #IanDunlap #RashadBilal #StockMarket #BlueChips #Portfolio #SuccessionPlanning #MarketAnalysis #OpenAI*

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