Who Will Win the AI Race? Apple, Google, Microsoft and More

17 Jan 2026 · 16 min · 5 chapters

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Earn Your Leisure Podcast Episode Summary

Episode Title

Who Will Win the AI Race? Apple, Google, Microsoft and More

Hosts

  • Rashad Bilal
  • Troy Millings
  • Ian Dunlap

Overview In this episode, the hosts discuss the future of major software companies in the age of artificial intelligence (AI). They analyze which tech giants are poised to succeed and which ones are at risk of falling behind in this rapidly evolving landscape.

Key Topics Discussed

  1. AI-Indestructible Companies
  2. Strong Contenders:
  3. SAP: Recognized for its enterprise software capabilities.
  4. Intuit: Noted for its resilience in the AI era.
  5. ADP: Mentioned as another sturdy player in the industry.
  6. Companies at Risk:
  7. Duolingo
  8. Adobe
  9. Salesforce
  10. These companies may struggle to adapt to changes brought about by AI.
  1. Microsoft's Leadership in AI
  2. Copilot Integration: Microsoft's effective use of AI in its software ecosystem is highlighted.
  3. Azure: The platform's innovations are discussed as critical to its success.
  4. Overall Position: Microsoft is seen as a dominant force in integrating AI into existing software, potentially "eating up" other companies.
  1. Sleeper Picks
  2. ServiceNow: Identified as an underrated company that excels in connecting systems and managing workflows. Its innovative leadership is praised.
  1. Agentic AI Stack Debate
  2. The hosts discuss who might create the first comprehensive AI platform capable of managing personal tasks (like email management).
  3. Google: Considered a frontrunner due to its established AI infrastructure.
  4. Apple: Although it has a vertically integrated ecosystem, it is criticized for underinvestment in AI, which might hinder its competitive edge.
  1. Criticism of Apple’s Leadership
  2. Tim Cook's Strategy: Rashad Bilal critiques Cook's leadership, suggesting that Apple has missed opportunities in the AI space.
  3. Comparison to Past Failures: The discussion draws parallels to companies like BlackBerry and Intel, warning Apple of the risks of complacency.
  4. Leadership Change: The potential need for new executive leadership to drive innovation is debated, with the hosts pondering whether Apple is preparing for succession.
  1. Innovation Concerns
  2. Lack of New Products: The hosts express frustration over the lack of innovation in Apple's key products over the years.
  3. Comparison to Competitors: The need for Apple to innovate and possibly acquire new technology is emphasized to maintain market leadership.

Key Takeaways

  • Companies like SAP and Intuit are positioned to thrive in the AI era while others like Duolingo may struggle.
  • Microsoft is seen as a leader in AI integration, with innovative products that enhance its software capabilities.
  • ServiceNow is identified as a potential "sleeper" company poised for success.
  • Google is likely to be the first to launch a comprehensive agentic AI stack due to its existing infrastructure.
  • Apple's current leadership under Tim Cook comes under scrutiny for not capitalizing on past opportunities and facing competitive threats.

Conclusion The discussion presents a thought-provoking analysis of the ongoing AI race, emphasizing the importance of innovation and strategic leadership in determining which companies will thrive. The episode ultimately raises critical questions about the future of major tech companies in the AI-driven economy.

Hashtags

  • #AIEra
  • #TechStocks
  • #MarketMondays
  • #Apple
  • #Google
  • #Microsoft
  • #Innovation
  • #Investing
  • #TimCook
  • #AIInvesting
  • #TechTalk
  • #SoftwareStocks
  • #FutureOfAI
  • #ServiceNow
  • #SAP
  • #Intuit
  • #Amazon
  • #Meta

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Identifying AI Software Winners

1:58 to 3:00

Discussion on which software companies might thrive in the AI era.

“With that being said, who will be the software winners in the AI era?”

Microsoft and ServiceNow: Key Players

3:00 to 4:24

Exploring Microsoft and ServiceNow as potential winners in AI software.

“But you need to find some companies that will not be negatively affected by AI, regardless of how advanced that get.”

Google vs. Apple: AI Leadership Debate

4:24 to 6:40

Debating which company might lead in AI innovations.

“And if they get that piece, Apple's going to slide to seventh in valuation overall.”

Apple's AI Innovation Challenges

7:18 to 14:04

Analyzing Apple's struggles in AI innovation and market competition.

“You have a Gmail calendar as well, right?”

Evaluating Tim Cook's Leadership in AI

14:04 to 15:36

Discussion on Tim Cook's performance and leadership in AI compared to other CEOs.

“Can we argue that the stock has performed?”
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Transcript

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2:05Eventually, we're going to go through the list of the ones that won't recover as a result. And it's a lot of them. But I think there are a few. But two, I want to highlight companies that I haven't talked about a lot. One is SAP, which is enterprise software. And the other was into it. Of course, you have Palantir, you have Amazon that are adjacent. But the thing I was telling Stock Club last night, find the companies that are going to thrive that are a indestructible, meaning regardless of what AI does and how prolific it becomes. Then you can even throw ADP in there. There are certain companies that won't be negatively affected, but companies like Duolingo or Adobe or some others may Salesforce may be.

2:52This air trade isn't going away. I think we probably have another, what, maybe 12 years, nine years of this trade. But you need to find some companies that will not be negatively affected by AI, regardless of how advanced that get. And I think SAP and Intuit are two good versions of that. All right, I'm going to go different. I'm going to go different. And this is this is why this makes this show so unique is that you're going to get a vast array of opinions and information. I think one is is the obvious. I think Microsoft for sure. of course software because yeah i didn't want to mention obvious yeah yeah i just think people when you understand what microsoft does it actually does the opposite it's like all right that's software how do we take ai and incorporate it to eat everybody else yeah right so like if you think of them think of them as the person that's going to eat up software companies by incorporating ai and they've done that already with copilot with azora's doing um with all we we know that already i think an interesting one is service now it's underrated an underrated one it's sleeper but it's another one of these companies that deals with managing workflows and connecting systems to people right so when you you think about the we'll talk about software companies that we don't think are going to survive service now has been super innovative um i've been watching their ceo for the past three years interesting dude um and then i started to understand what the company does that would be my sleeper inside of this space so i got microsoft and i'm going to take service now as winners in this in the software ai era who do you think would be the first company that comes out with a full agentic ai stack like enterprise level or consumer level where you can just say hey answer all my emails for me um because there are some smaller companies that do it but who do you think would be the first player out of Google, Microsoft, Apple, Tesla to have full skill?

4:49I think it's Google. Yeah. And if they get that piece, Apple's going to slide to seventh in valuation overall. It's built in. The win is built in when you're talking about we like convenience. Right. So if there is a company that has your email already, that has your work schedule already, that has your life schedule calendar yep well i mean you can make the same argument for apple do they but do you have an email with apple iCloud but they haven't put as much money and that's my point why i'm so frustrated the infrastructure and entire ecosystem what you needed that last one infinity stone and you didn't build it but then also people like elon must say email is not even going to be around in 10 10 years email is going to be a thing in the past so but i think Apple, I mean, if you really think about it, as far as vertical integration, they have your text messages, they have your music, they have your calendar.

5:49Everybody might not use iCloud, but I do. So in that case, they have your email. And it's the device that most Americans are using an iPhone. So, I mean, they're perfectly set up for that. I think they're more set up for that than Google. The thing is, Google is going to execute it faster, though. Yeah, I think what Google has done, and it's interesting because we could say that they've been the leader in AI for a long time, they just didn't have the product to do it. When you talk about DeepMind and all the architects that came from there, the iCloud situation is true, but it's more of a storage.

6:29I think if you have an iPhone, you have iCloud, right? Whether it's from, it saves your text messages or it does save your music. But that part of, there is no Apple calendar, right? Like all the things you use on your phone for the most part are going to be from Google. No, there is an Apple calendar. I'm just saying most people. Run a business and not thinking about podcasting? Think again. More Americans listen to podcasts than ad-supported streaming music from Spotify and Pandora. And as the number one podcaster, iHeart's twice as large as the next two combined. So whatever your customers listen to, they'll hear your message.

7:03Plus, only iHeart can extend your message to audiences across broadcast radio. Think podcasting can help your business? Think iHeart. Streaming, radio, and podcasting. Let us show you at iHeartAdvertising.com. That's iHeartAdvertising.com. I use Apple Calendar. You have a Gmail calendar as well, right? I don't use that. I use Apple Calendar. You have a Gmail account? I do, but I don't use it though. My calendar, I use my calendar religiously. Shout out to AB, put stuff on my calendar. He does that through Gmail. It's on Apple. It's on your iPhone, but he's doing it through Gmail. I'm on those calendars.

7:36Yeah, but it's an Apple Calendar. It's a Gmail, bro. It's the Apple calendar. No, I'm just saying. No, but I'm saying this is the Apple calendar. There's a Gmail calendar. No, no, no. What's getting sent to you is through Gmail. You could be sending it through Gmail, but it's on my Apple calendar. That's what I'm saying. So it's integrated with Apple. Now there's a Gmail calendar. Oh, right, right, right, right. Yes, yes. There's a Gmail calendar. Yes, Gmail calendar app. Yes, what I'm saying. I'm using the Apple calendar. But the information that's coming to your calendar is from Google. Yeah, but it's still integrated with that.

8:06Right, that's what I'm saying, right? Like you're not putting it in an Apple device and saying, here's Apple. You're used. They're still using Google, even Apple itself. If you look at the search engine, that data, that's that's that's still. Well, people are using their Gmail accounts from their iPhone. But they work together. Exactly. Yeah, that's what I'm saying. Google is a partner that they need to make that software work more efficiently. Right. Yeah. They work. They work together on it. No, true. But what I'm all I'm saying is that Apple is fully integrated. To me, Apple is the most integrated thing in my life because I listen to my music on Apple Music.

8:41I check my email on iCloud. I have my calendar on the Apple calendar. I get my text messages on the iPhone. Everything that I do, my whole life is run through Apple, not through Google. That's not true. You're on YouTube right now. I'm talking about my personal, like if I have a personal assistant and they're looking and they're checking things, Like all of that stuff is on, is on the iPhone. Yeah. But so if you look at the users, right, if you look at, and by the way, I'm watching, I watch YouTube on my iPhone, but it's still the platform. I understand that. What I'm just saying is the outlet.

9:17I have a question out of the big 10 companies besides Tim cook. Has anybody else dropped the ball on AI except him? I can't say that he's, he hasn't kicked the ball yet. Tim cook. I can't wait for you to fucking retire. i'll say it you see you at the start line and everyone else has ran laps and now they're going to the javelin throw what would you like what do you think what do you think that they should do because they put the air pods out that can translate um different languages they had they were original with siri they had siri before anybody was talking about it they acquired started what was alexa first or was siri first i think siri siri was first i think okay they started siri they had so they have artificial intelligence integrated throughout their whole entire ecosystem what it just hasn't evolved what do you want them to do what do you what would you want them to do i would have the history of apple and its greatness has always been acquisition they could have acquired the deal that Microsoft got was presented to Apple first didn't do it yeah they had the chance to get it first didn't do it then you get into this proxy war with Zuckerberg and Elon you took your eye off the ball what I would like is a new executive who is going to acquire AI talent and even though meta has not turned the course yet on the stock they're making investments there for AI and I don't the way that Metastock is getting treated is how Apple should be and Tim Cook's tenure he had an immense opportunity with the ecosystem the platform you get the 30 tax for anybody who uploads anything into your app store and you got comfortable being a services company and now Google came from out of the ashes and they're Goliath that you're facing with no rock and no slingshot so while they have the pieces there it's like when the Warriors won the 73 games and couldn't bring home the chip.

11:25I think innovation is the word, right? Like we've been doing this for six years on Market Mondays. There was the autonomous vehicle that we thought that they were going to do. They backed out of that. Didn't do it. We thought the wearable would be the thing, and the Vision Pro didn't turn out to be that. But even the small scale idea, it looks like Meta got ahead of that with their wearables. I see a lot of people wearing the Meta glasses. Those are two areas. We haven't seen innovation inside the iPhone in probably seven or eight years. I know that they're coming out with the foldable one. Did you see the foldable iPhone?

12:04Yeah, shout to everybody who had Android who didn't have that. Shout to Drew. Even the AirPods, I like that iteration, even though I don't have them, but that was an acquisition from Beats. Apple has acquired their way into greatness and then they stopped acquiring and got comfortable and everyone else is catching up. They're falling on the market cap list. Like I said, they were a year and a half ago. They're number three. I mean, they just got passed. The interesting part is this and this is the part. We can say all these things, but people are still buying the products. It was a force upgrade.

12:40It was a $4 trillion company. I think it gets taken for granted because it's a necessity. We're running this show right now, and it wouldn't be possible without Apple. On the desk right now, there's two iPhones. We're buying the products. They're on the desk right now. I agree. That has nothing to do with the underinvestment AI, though. There's two iPhones. There's an iPad, and there's a MacBook. We're still buying a product. That's what I'm saying. We're still buying a product. So the valuation of the company continues to rise, right? Like I bought the 17. I bought the new earbuds. People are doing that.

13:12This was when we talk about innovation. No, I'm just saying in terms of think about what Google's had to do and had to announce and had to acquire to get to this valuation. Right. Think about how Meta has announced these things and acquired and it's still sitting at the right. They're sitting at the one point four billion. Apple hasn't done all those things that we're seeing and people still buy the product and the valuation continues to rise. It all time last year. You know what this reminds me of? It reminds me of the same sentiment at a larger scale that Intel and BlackBerry had in 2008 and 2009.

13:49If you've been around long enough, you say, okay, Sergey came out of Elons in office. Whether you like him or not and like his disposition in the stock process, Trump's in Mar-a-Lago or the office. um tim cook out of the best of breed ceos has undelivered the most in terms of ai that's my point when they had a chance to lead this race and they lost it i think both things are true i think both things are true yes he is under he's under delivered has the stock been rewarded for what it's done in the past year yeah that's not the he's even said last week oh i'm fucking tired to be in an office and I'm ready to get the fuck out the seat.

14:36Can we argue that the stock has performed? It's performed, right? I agree. Yeah, that's my pick. That's my baby. But I also can say that they've underperformed in terms of leadership. Both things are true. I'm with you. We'll see. We'll see. We'll see if they go in a new direction. It's like sports. Sometimes you got to change the coach. If the team is not performing, even if the team is winning, the Knicks, they went to the conference finals last year and they still fired the coach. That's a fact. So sometimes you, you fire a coach just because you need a new culture. So maybe a new CEO comes in with a new culture, new game plan and shake things up and is a little bit more innovative.

15:17We'll see. We'll see. Are you happy with the job? Are you happy with the job that any Andy Jassy has done at Amazon? Absolutely. Okay. Yeah. I am. And really quick as of early January, 2026 internal succession planning has accelerated um an official announcement should come at the end of the first quarter from what i've been told personally from somebody who works at hq he will be out january of 2027 this episode is brought to you by pnc bank a 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.

16:00It 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. This is an iHeart Podcast. Guaranteed human. Thank you.

From the publisher

In this insightful clip from Market Mondays, Rashad Bilal, Ian Dunlap, and Troy Millings dive deep into the future of software companies in the rapidly evolving AI era. As artificial intelligence transforms every industry, which tech titans are set to thrive—and who is at risk of falling behind? Ian Dunlap highlights "AI indestructible" companies, naming SAP, Intuit, and ADP as strong contenders, while noting that well-known names like Duolingo and Adobe may face challenges. The panel debates the obvious winners—like Microsoft, with its Copilot integration and innovation through Azure—and discuss sleeper picks such as ServiceNow, lauded for its forward-thinking leadership and connectivity solutions. The discussion shifts to the race for an "agentic AI stack": an AI platform that can handle personal tasks like answering all your emails hands-free. Rashad Bilal and Ian Dunlap weigh in on whether Google, Apple, Microsoft, or Tesla will be first, with Google considered a front-runner thanks to its deep AI roots and integration with essential services like email and calendar. However, Rashad argues Apple’s dominance in vertical integration (managing texts, music, calendar, and email on a device most Americans use) gives it an edge—if it can catch up in AI investments. The clip doesn’t shy away from tough criticism of Apple’s leadership, with Rashad questioning Tim Cook's strategy and pointing out that Apple was offered the same deal that made Microsoft an AI leader—and turned it down. While Apple products remain indispensable and its ecosystem robust, signs of underinvestment in AI are causing market cap slippage and stirring calls for leadership change. Comparisons are drawn to companies that failed to keep up with innovation in the past—like BlackBerry and Intel—serving as a cautionary tale for Apple if it doesn’t shake things up. The hosts discuss what Apple should do next, from innovating through major acquisitions to fostering new executive leadership capable of driving AI progress. The debate closes with a reflection on whether being top of the market is enough—or if Apple, like in sports, needs new leadership to set a winning culture. Are Tim Cook’s days numbered, and is internal succession already in motion? Don’t miss this candid, thought-provoking conversation on how AI is reshaping the tech landscape for giants like Apple, Google, Microsoft, Amazon, Meta, and more. *Hashtags:* #AIEra #TechStocks #MarketMondays #Apple #Google #Microsoft #Innovation #Investing #TimCook #AIInvesting #TechTalk #SoftwareStocks #FutureOfAI #ServiceNow #SAP #Intuit #Amazon #Meta

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