Ben Gilbert
Correspondent
9
APPEARANCES
9
PODCASTS
012
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Sep 14, 2026
The AI Slowdown Debate | Nico Wittenborn, Scott Keogh, Mitchell Green, David Rosenthal & Ben Gilbert, Faraj Aalaei
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144:38Ben GilbertGUEST
You know, a lot of the smaller contractors, residential GCs, they're already Home Depot is their primary just-in-time supply, and increasingly, like, their main supplier.
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144:51Ben GilbertGUEST
But if you think about, like, really big builders, multifamily, commercial, you know, cranes, all, uh, big stuff, um, historically Home Depot has not been penetrated into that.
Disney's Biggest Swings and Misses, Plus Iger vs. Eisner—With the Acquired Guys
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13:45Ben GilbertGUEST
Uh, and then two, you're right, they're probably five years too late to launching their own streaming service 'cause imagine the subscriber count that Disney+ could've been at.
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13:52Ben GilbertGUEST
Let's say where they were, COVID accelerated a lot, so let's, let's not say five years, but let's say they could've been at the current numbers by 2023 instead of 2026, then they could've started doing this bundling thing that they're obsessed with now, and that everybody's getting obsessed with now, earlier.
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14:08Ben GilbertGUEST
And assuming the future of Netflix and the future of Disney are, are both being the distributor and then getting other people to distribute their content on their streaming bundle, uh, they could've been in a, a better position, whereas now it feels, uh, very reactive, and there's a, a danger that it is creating brand risk to, to put all these other things so close to, uh, Disney IP.
7 MINS LATER
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21:40Ben GilbertGUEST
... sports networks, so it ends up being, like, s- high 40s or something like that.
How Microsoft is scaling legal with AI: AI Now Episode 4
7:48

Bryony EvansHOST
But I think one of the challenges that we see in organizations is, how do you help to drive the uptake of those use cases or the initiatives around AI, and think about what those accelerators might be? Do, do you have sort of ways that you accelerate uptick of d- uptake of different AI uses, or maybe on the flip side, are there blockers that you have to really keep an eye out to overcome?
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8:16Ben GilbertGUEST
At a really high level, um, our approach is to bring in a culture that rewards curiosity and experimentation.
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8:26Ben GilbertGUEST
Um, it redefines failure within appropriate guardrails and kind of drives that psychological safety, and that, that's gotta be the platform by which, uh, you start.
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8:36Ben GilbertGUEST
I think from a, from a blocker perspective, people are time poor, especially lawyers.
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8:42Ben GilbertGUEST
And so unless you, um, incentivize and create space for learning, you're probably not gonna have much luck.
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8:52Ben GilbertGUEST
The other thing is that we all have muscle memory, and if you don't create a repetitive, um, strategy and, and, uh, reinforcement, then that muscle memory very quickly snaps back to the way that you've always done things.
5 MINS LATER
If and How to Scale the Acquired Podcast
33:57
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22:20Ben GilbertGUEST
What this really comes down to, Dave and I sort of had this aha moment a few years ago that you can run a media business a different way than media businesses are currently run.
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22:31Ben GilbertGUEST
Media is sort of notorious for low margins and raising at high valuations, getting ahead of their skis and then needing to do big newsroom layoffs or low salaries for journalists or often being nonprofit organizations.
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22:46Ben GilbertGUEST
And David and I sort of looked at each other and we were like, but other than software, media is the best business model of all time.
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22:58Ben GilbertGUEST
It takes the same amount of work for us to make an acquired episode for 10,000 people as it does for 10 million.
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23:04Ben GilbertGUEST
So if your inputs don't need to scale with your outputs, why wouldn't you make the least amount of content possible and put all your energy behind just finding all the people in the world who... who would be obsessed with that content and then your revenue can scale commensurately with that versus what most media companies do is, hey, we just raised some more money or we just had a good year, let's increase our overhead again and let's try and start from zero in a new vertical or a new beat or something and try to build up a listener base.
10 MINS LATER

Brian KennyHOST
Do you think at all about the implications of AI on the industry itself but also on Acquired? Do you feel like there's a disruption coming where AI could do a lot of the legwork that you're doing and people wouldn't need you anymore?
Ben Gilbert & David Rosenthal - The Obsessive Craftsmanship Behind Acquired - [Glue Guys, EP.52]
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20:54David RosenthalGUEST
And obviously that event changed Facebook's and Mark Zuckerberg's fortunes hugely.
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21:02Ben GilbertGUEST
We sort of released it as is with some tongue-in-cheeky comments in there, which we probably wouldn't do today.
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21:10Ben GilbertGUEST
David came to me again and said, what if it's not about grading transactions? What if we've leaned so much into story in addition to analysis? What if we just tell the story of Tesla as a company without a transaction? It's not about the IPO.
36 MINS LATER
Gary Cohn & the Acquired Podcast Interview 7/16/25
38:51
And what were the incentives that led him to do that relative to everybody else who, and did they have different incentives? Did you think that you understood the answer there?
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39:03Ben GilbertGUEST
Uh, his answer was, he kind of took it to how he incentivized people in his organization.
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39:09Ben GilbertGUEST
I think the real answer here is Jamie is willing to think with a longer view than his peer set in the 2004, 5, 6 era.
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39:18Ben GilbertGUEST
And his thinking was, if I'm trying to build a company that's in a great place 30 years from now, we're going to have to withstand at least one, maybe four or five big drawdowns, wars, terrorism, like let's just bake it all in and assume we need that margin of safety and operate with that.
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39:34Ben GilbertGUEST
Whereas everybody else was saying, I hope there's not a recession in the next year and maximizing profit in the short term.
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41:13Ben GilbertGUEST
I feel like I'm in the center of the universe, I will say, after watching... you know, hundreds of hours of this show.
Acquired's Success Secret: Ben Gilbert's Quality Approach
16:56
Guy KawasakiHOST
So how about giving us some pattern recognition about key factors that make these companies successful?
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17:08Ben GilbertGUEST
The biggest thing we've learned is that each of these extreme outliers that we study, these most successful businesses in the world or most successful businesses in any given category, are successful in a unique way.
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17:25Ben GilbertGUEST
The founders had some specific skill set that was well tailored to that industry, that product set, that moment in time, and that leadership style.
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17:35Ben GilbertGUEST
If you look at Steve Jobs and you compare him against Frank Mars from the Mars M&M Snickers candy company, or you compare against the Dumas family at Hermes, or...
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17:49Ben GilbertGUEST
Ingvar Kamprad at IKEA, it's a pretty different set of principles and a different strategy to create these outlier successful companies.
18 MINS LATER
Here's What It Takes to Make a Great Company
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32:38Ben GilbertGUEST
But I will say, though, I think if, if your goal is how do I start a trillion-dollar company? How do I start one of the 30, 40, 50 most important, largest, most successful, durable companies on the planet? Founder-led companies have a much higher probability of being that.
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33:01Ben GilbertGUEST
You look at Hermès, this is a, you know, what is it, 150-year-old company? The original founder is not gonna be the person running that.
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33:08Ben GilbertGUEST
But close control is a key to the success of that business and so many others, where, uh, th- they control their own destiny.
6 MINS LATER
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39:19David RosenthalGUEST
And then it's just, you know, can you navigate that crisis and emerge on the same or better, you know, to- compounding trajectory that you were before.
Acquired Podcast on the NFL (with Ben Gilbert and David Rosenthal)
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56:57Ben GilbertGUEST
Whenever you're watching football, it kinda looks like somehow the camera is at or near the line of scrimmage.
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57:02Ben GilbertGUEST
Well, when it was at the 50, whenever you'd be starting in the red zone, it's really this oblique angle to be watching the play, so they put two more cameras on the 25-yard line so now you're always looking at or near the line of scrimmage head-on.
21 MINS LATER
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78:31speaker_12UNKNOWN
Oh, really?



