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Earn Your Leisure

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

Earn Your Leisure

iHeartPodcasts

News, Entrepreneurship, Business, Investing, Careers, Education, Business News

4.87.8K Ratings

🗓️ 17 January 2026

⏱️ 16 minutes

🧾️ Download transcript

Summary

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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Transcript

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0:00.0

This is an IHeart podcast. Guaranteed human.

0:04.6

Earners, what's up?

0:05.5

You ever walk into a small business and everything just works?

0:08.7

Like the checkout is fast.

0:10.3

The receipts are digital.

0:11.9

Tipping is a breeze.

0:13.8

And you're out the door before the line even builds.

0:16.2

Odds are they're using Square.

0:18.9

We love supporting businesses that run on Square because it just feels seamless,

0:22.8

whether it's a local coffee shop, a vendor at a pop-up market, or even one of our merch partners.

0:28.4

Square makes it easy for them to take payments, manage inventory, and run their business with confidence,

0:34.1

all from one simple system. One of the things we love mostly seeing neighborhood

0:38.8

businesses level up. There's this West Indian spot right in our community that started with a small

0:44.0

takeout counter. Now with Square, they've been able to expand into a full sit-down restaurant and even

0:49.8

started catering events across the city. That's the kind of growth that inspires us, and it's

0:55.4

powered by Square. Square is built for all types of businesses, from the corner bagel shop that turned

1:01.2

into a local chain, to the specialty market with thousands of unique items, to the stylist

1:06.5

who's been holding you down for years. If you're a business owner or even just thinking about launching

1:11.7

something soon, Square is hands down one of the best tools out there to help you start, run, and grow.

1:18.3

It's not just about payments. It's about giving you time back so you can focus on what matters most.

1:24.1

Ready to see how Square can transform your business. Visit square.com

1:28.4

backslash go backslash EYL to learn more. That's square.com backslash go backslash

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