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Masters of Scale

Pioneers of AI: Mark Cuban’s investment strategy in this new era of tech

Masters of Scale

WaitWhat

Business, Jeff Berman, Startups, Reid Hoffman, Management, Diversity & Inclusion, Mindset, Bob Safian, Entrepreneurship

4.64.4K Ratings

🗓️ 30 December 2025

⏱️ 48 minutes

🧾️ Download transcript

Summary

Mark Cuban has spent decades as a serial entrepreneur and investor, with one of the best track records on the planet (including celebrity status on ABC’s Shark Tank). In this episode of Pioneers of AI, Cuban joins host Rana El Kaliouby for a wide-ranging conversation about whether we are in an AI bubble, how he’s applying his investment philosophy to AI, and why the AI world is tending to excite him less and less each day.

Learn more about Pioneers of AI: http://pioneersof.ai/

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Transcript

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0:00.0

If you're focused on scaling your business, you know the complexity kills efficiency, which is why FreshWorks is here to give you uncomplicated service software.

0:11.8

Freshworks builds intuitive tools that make work easier and deliver real ROI today, not someday. Their AI doesn't replace your people, it unlocks their potential. If you want to

0:24.3

increase your team's efficiency and uncomplicate your business, try fresh service for IT and

0:30.1

fresh desk for customer support. Learn more at freshworks.com. Does it ever feel like you're paying for 20 platforms to do the job of what really should be

0:41.2

just one?

0:42.6

That's not software as a service or SaaS.

0:45.6

It's sad.

0:47.0

Software as a disservice.

0:49.2

Replacing your stitched together tech stack with one platform for all your departments,

0:53.7

well, that's Rippling.

0:55.3

Rippling eliminates the bottlenecks and busy work of legacy tools and point solutions by

0:59.7

uniting your global HR, IT, and spend teams on just one platform. And right now, you can get six

1:07.6

months of Rippling free when you sign up at rippling.com slash scale.

1:12.9

That's R-I-P-P-L-I-N-G.com slash scale.

1:18.2

Don't get sad. Get Rippling.

1:20.9

Terms and conditions apply.

1:22.8

Hey, everyone, Bob Safian here.

1:25.3

We're just a few days from 2026, and so we want to share a special

1:29.9

gift for our year-end episode. It's a conversation with the iconic Mark Cuban, conducted by my friend

1:37.0

and colleague Rana El Caliubi. This episode originally ran as part of Rana's terrific

1:42.8

Pioneers of AI podcast. I encourage you to subscribe to the part of Rana's terrific Pioneers of AI podcast.

1:45.3

I encourage you to subscribe to the show.

...

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