Acquired’s Success Secret: Ben Gilbert’s Quality Approach

Guy Kawasaki:
Hello, I'm Guy Kawasaki. This is the Remarkable People podcast, and today's remarkable guest is Ben Gilbert. He is co-founder and co-host of a very famous podcast called Acquired. And this podcast is known for extremely deep dives, like two to four hour deep dives into the strategies of legendary companies like Rolex and Meta.
And oh my God, we're going to get into it. He has millions of listeners around the globe. He's also a pioneer and entrepreneur. He's launched successful ventures, and he continues as a venture partner shaping innovative startups.
Believe it or not, he was recognized by GeekWire as a young entrepreneur of the year, which is something I never even was considered for. I'm neither young nor entrepreneurial at this point, but anyway. And he blends really deep technical expertise, a great sense of humor and visionary leadership, and this enables him to reveal the untold stories of just some great companies. And not just tech companies, as you'll soon find out. Welcome to the show, Ben Gilbert.

Ben Gilbert:
Thank you so much for having me.

Guy Kawasaki:
Listen, I'm going to go a little bit backwards first, because I just need to know something, you were kind of responsible for Microsoft Word or Office on the iPad. And I just want to know, is Word on the iPad ever going to have style sheets? Can you just place a call or email and say, "Guy needs style sheets on the iPad Word?"

Ben Gilbert:
It's so funny you started here, because first of all, responsible for is not true. I was a part of a 200-person team that built the versions of Office for Mac in the 2011, 2012, 2013, 2014 timeframe. And that code base we ported over to build the first version of Office for iPad.
And that was one of the coolest career experiences of my whole life. Up until the moment where we were ready to ship and company leadership said, "Actually, you're not shipping. This has been a hedge the whole time. We don't want to make the iPad better. We're the Windows company."

Guy Kawasaki:
Are you kidding me?

Ben Gilbert:
I'm euphemistically saying company leadership. That was a decision made by the CEO, Steve Ballmer, who yesterday we interviewed on Acquired for our next episode. And got to talk all about the strategy of that sort of crucial moment in time.
How long should we stay the Windows company versus how long should we look to the future? So, this has been on my mind a lot this last week. And obviously, that team did eventually ship when Satya came in as CEO, and the rest is history. I have no idea on style sheets to directly answer your question.

Guy Kawasaki:
Bummer.

Ben Gilbert:
It was actually awesome. I loved doing that interview, and I think very highly of Steve as a person. At the time when I worked at the company I think I disagreed with the strategy, but I think very highly of him as a human.

Guy Kawasaki:
We'll get into this a little later, but Steve Ballmer is one of the billionaires who has not gone dark shortlist today. And his work about InfoUSA is very interesting too.

Ben Gilbert:
Yep.

Guy Kawasaki:
Steve Ballmer is like Jimmy Carter. He's getting better with age.

Ben Gilbert:
I'm sure he'll appreciate that.

Guy Kawasaki:
All right, so many of your episodes are about the stories of the origin of a company. Let's just repeat your story. The story goes that you and David started Acquired to learn about successful acquisitions to be better venture capitalists. And then, is this a true story?
Because I'm also aware of the Pierre Omidyar story where he says he started eBay so his girlfriend could sell Pez dispensers, that's basically a bullshit story. Is this story about you wanting to be better venture capitalists, the reason for starting Acquired true?

Ben Gilbert:
Yeah, I think that was in the back of our minds of a sort of logical reason to do it in a way we could justify spending the time. Because the thinking was, most companies that have successful exits get acquired, most actually don't IPO. And so if we want to start and invest in companies that have successful exits, then what we should do is study what makes acquisitions great and very value-accretive for the acquired company and then work backwards from there.
And obviously, that's expanded dramatically today to telling the entire story of a company from founding all the way to where it is today. And actually, most of the companies we studied didn't get acquired, because they didn't need to, and they could run independently and get very large over a long period of time.
But in practice, why did we start doing it? David and I, we had a budding friendship, but we were never making the time. We would keep saying, "Oh, let's get drinks," and then another month would go by and we'd say, "Shoot, we really need to get drinks." And so this was a forcing function for us to actually spend more time together. And we've always both had this excitement around tightly scoped ideas.
An idea where you can envision what the whole product looks like, you're capable of making it yourself or with a small group, and shipping it and saying, "This provides value to people in a very tight, discrete way." And I've always been allergic to the startup ideas that are really big and really hand wavy and hard to follow.
And sometimes those change the world, but I'd rather ship something small and say, "We made another Acquired episode. In this episode you will learn the entire history and strategy of a company, why it worked, get their whole story and this is the canonical piece on that thing. We hope you enjoy." And it just has a nice bow on it.

Guy Kawasaki:
Just sitting here, Ben, I cannot think of a company that started with hand waving and the big picture and worldwide domination that succeeded. I can think of one where the two executives are in jail now, but that's about it.

Ben Gilbert:
We were very lucky on a lot of things, including timing. We were very early to podcasting. In fact, we launched the year before AirPods came out, and I think we all know it was really weird for a month and then suddenly the whole world was like, "Oh, actually we accept the fact that everyone's wearing headphones all the time and listening to podcasts and audiobooks."
So, a lot of luck involved, but there was definitely pretty quick product market fit with this idea that we had for a narrowly scoped show and a listener base that wanted to hear it.

Guy Kawasaki:
So, the quick summary of the origin of Acquired is it was because of alcohol and AirPods basically?

Ben Gilbert:
Basically.

Guy Kawasaki:
Okay, at least we got to the truth here. Now it seems to me that this 2015 timeframe where you started and for the next couple of years it was mostly about acquisitions, and then shifted to IPOs in 2018. And then in 2020 it was basically any iconic company. So, is that kind of the arc of life of Acquired?

Ben Gilbert:
Your information's very good. Either you just did great research or you listened all the way through that period of time, which would make you one of few people. Because for a long time not many people listened.

Guy Kawasaki:
I don't want to burst your bubble.

Ben Gilbert:
Did AI help meaningfully in this research?

Guy Kawasaki:
Absolutely. Now from a marketing perspective, if you could do it over, would you name your podcast something different than Acquired? Because to draw a parallel from your podcast, imagine if the people who created Rolex called their company Pocket Watch, right? And so you stuck yourself in a corner of acquisitions, but now you're far beyond that. With hindsight, would you have picked a different name?

Ben Gilbert:
I don't know. There's a few reasons why I think I wouldn't. Aside from all the obvious reasons why you think we should. One, for a very long time all podcast players ranked the podcasts alphabetically.

Guy Kawasaki:
Okay.

Ben Gilbert:
So, if you don't know what you're going to listen to and you open your podcast player, we have prime placement. And now things are a little bit more algorithmic and they're delivering, and "Hey, here's the latest episode." But 90 percent of our audience for a long time was on Apple podcasts and we'd show up front and center. So, that was a pretty funny hack that I don't think we anticipated.
Two, I think people underestimate the importance of path dependence in entrepreneurship. I think if we had come out with a show today that looks like Acquired, it might not have worked, because it might not have found the right audience out of the gate. A thing that we did really well early was have a really valuable, really intelligent, critical thinking listener base.
And the initial Acquired product was valuable to them. And the only way that we've ever grown is by people telling their friends, we've never done any meaningful advertising. So, it's all been organic doubling year over year of audience, which means that it's all word of mouth. And so, you need to start with a passionate kernel that is representative of the group you ultimately want when you're large.
And I think naming Acquired, having that format, having that early listener base is the reason that we were able to have the license to expand into what we are today. So, does the name make total sense today? No, but it also doesn't seem to have held us back. We're the number one technology podcast on Apple and Spotify. And I don't know, it seems like the name is a little bit amorphous enough that people are like, "I don't really get why it's called Acquired, but sure, whatever."

Guy Kawasaki:
You know what, I'd like to point out that what you just said, I am friends with Meredith Whittaker, the CEO or president of Signal. I am, a lot of information is going to come. I am deaf, so I read your transcripts, first of all. Thank you very much for doing transcripts. I read the transcript of the Meta that we have two episodes, but the Facebook episode, and there was a part where you said that when people joined the Harvard Facebook thing, there was already a lot of activity.
And you said that if you were in the middle of Ohio and you got people to join Facebook and they joined it and there's nobody from Ohio, because at that point you didn't have critical mass at Facebook. And so, in a sense, what you just said is the same thing, right? That you had this critical mass because you had a very narrow specialty just like when Facebook started.
If you were at Harvard, you got on at Harvard and there were lots of people from Harvard already. So I took those three paragraphs and I sent it to Meredith and I said, "This is the challenge for Signal. If you just try to get random people who are paranoid about privacy, they're going to join Signal, and there's nobody else they know. And I think that's holding Signal back."

Ben Gilbert:
That's interesting. The question then becomes, how has Signal accomplished having such a large user base if it's really holding them back? I guess they're not everywhere, but it has to be tens of millions, maybe even a hundred million users at this point.

Guy Kawasaki:
Yeah, I think it's more like sixty or seventy million, but sixty or seventy million if you compare it to Messages or WhatsApp.

Ben Gilbert:
Totally fair. Yeah, they'll be behind.

Guy Kawasaki:
Anyway, that's a tangent and I just want to express how impressed I am with Acquired, because I'm going to have to take you back in history. Before you were born, Ben, probably if Harvard Business School did a case study on your company, assuming it wasn't a negative case study, it meant you arrived. And then a few decades later if Walt Mossberg wrote an article about your company for the Thursday issue of the Wall Street Journal, it meant you arrived.

Ben Gilbert:
Personal technology.

Guy Kawasaki:
And now I would say, Marques Brownlee is the new Walt Mossberg. If Marques Brownlee covers your product, you've arrived. And I would say in my mind that Acquired is the equivalent of a Harvard Business School case, being written about your company. I looked at your episodes, and my God, it's such a rich mind for entrepreneurial information.
My hat's off to you, Ben, it was just fascinating. And in particular, what's fascinating to me, of course you cover semiconductors and social media and all that, but my favorite stuff was about Rolex and Porsche and stuff. So, I just want to fan Guy a little bit if you don't mind.

Ben Gilbert:
Well, look, I have been shocked that it has ended up this way. I think what David and I did, Acquired effectively represents our learning journey. And so, if you go back and listen to the ones from 2015, 2016, 2017, there's a real naivete there that I would go poke lots of holes with the ten years of learning that I've done since then in our analysis.
And I'm sure ten years from now I'll feel the same way about our current body of work. But I think the reason that the show has evolved and the reason why the storytelling and the analysis has gotten so much better, and I appreciate your comparison to the Harvard Business School case study or Marques Brownlee video.
I certainly don't think of them that way yet, but I understand why they can be viewed that way. It's just our evolving ‘aha’ moments. And I feel like we get kind of bored every two years or so where we feel like, "Oh, we've learned the core mental models that you need to know to understand the kind of thing that we're doing right now. What could we move on to next?"
And I think that is why we move to IPOs, why we move to whole company stories, why we studied luxury businesses for the first time, why recently we've been obsessed with these private family-owned companies that don't go public. It's this every once in a while, I think it's about every two years there's a yearning to understand a whole new set of mental models and business principles illustrated through these new batch of stories.

Guy Kawasaki:
I would say that my friend Carol Dweck would just basically say that you personify the growth mindset, right? You don't have a fixed mindset. If you had a fixed mindset, you would have stuck to acquisitions, so you truly personify the growth mindset. Now you're ten years into this and I can tell that you guys are really good at pattern recognition. So, how about giving us some pattern recognition about key factors that make these companies successful?

Ben Gilbert:
Obviously David and I think about this a lot. 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. The founders had some specific skillset that was well tailored to that industry, that product set that moment in time and that leadership style. You knew Steve Jobs.
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 Ingvar Kamprad at IKEA, it's a pretty different set of principles and a different strategy to create these outlier successful companies. And I think that's the point. I think it's that every entrepreneur needs to look at themselves and say, "In what way am I weird?
In what way am I the best in the world at something? Even if it's a strange something. And how can I combine a few of those traits together such that it's A times B equals 10,000 x where it's really well suited to a product, a market, a moment in time, a leadership style, a business strategy, a culture that I can create something to make jazz, to use a different example? How do I use my raw components to create jazz?"
That's one thing is, you can never say, "I need to be like Apple, therefore I should parrot Steve Jobs." That's just never going to work. Another thing that I think has become really obvious to us is, everyone says they operate with a long-term mindset, but most people don't.
And in most cases most people are not incentivized to. And if there's anything that we've learned from Acquired, it's that everybody ultimately follows the incentives, whatever incentive structure you set up. It's the old Charlie Munger aphorism. You show me the incentives and I'll show you the outcome.
It's highly predictable how people will behave whenever you're able to take a company with a single person thinking with a twenty, thirty, fifty-year view, who has their view of what needs to happen. They may not be right, and the world is littered with companies that have died because you had one crazy person who believed in something that just wasn't true. I think there's a bunch of examples, like DeLorean or kind of nutty folks that incorrectly predicted the future.
But then you also need that exact same characteristic where you need to be contrarian and right and have an incentive system set up where you actually can pursue your vision of the way the world needs to be. I think these dual class share structures allow for it. You look at the New York Times or Hermes or Meta or Google where the founders can maintain control.
Or these companies that stay private, like IKEA or Rolex or this mechanic of singular control by a person or entity thinking with a multi-decade lens, really does enable you to make bets differently than if you have the whims of quarterly reporting. Those I think are a few of the big ones.

Guy Kawasaki:
But you make a point that it's all about being a contrarian, but also right. And it seems to me that the contrarian part is easy. It's the right part that's hard. Do you have any insights on what's the pattern recognition for being right? It's self-selection, you only interview the successful companies, so you don't really investigate the people who are contrarian and wrong.

Ben Gilbert:
I think you are exactly right that it is much harder to be of that equation. It's much harder to be right than it is to be contrarian. There's lots of contrarians running around that are never successful. The dirty secret of Acquired is that it is totally the study of survivorship bias. We're talking about these companies that are worth hundreds of billions of dollars.
We're not talking about the guy with an equally wackadoo idea to what Bill Gates thought that the personal computer was going to change everything and see a PC on every desk, but their vision was just wrong. We aren't covering those. But my personal view on the lessons learned from that and how to tackle it is, if you're a passionate entrepreneur, the only way you're going to succeed in creating something world-changing is to do the thing that you are irrationally passionate about.
And I don't really think you should moderate or temper that instinct. You could say, "Geez, what if I'm wrong? What if you're wrong?" And now you have to go and work on something that you are not lit up by? That's not an exciting life. And yeah, you should be smart around the margins and position your company so it can be successful, but history is made by the people with really obsessive crazy ideas.
And we have this natural selection process where the world figures out what the right ideas are and then those are the ones that become big. It doesn't work that well for the individual entrepreneurs who are wrong, but as a society, it's actually a pretty good mechanism for everybody to run hard at a crazy idea.

Guy Kawasaki:
Obviously, my podcast is called Remarkable People, so I kind of don't look for people who failed or people who are mediocre. In a sense Acquired does the same thing, so there are times that I sit around, and I think, "You know, Guy," well to use a metaphor. A lot of people, they listen to this wisdom that a college degree isn't necessary because Bill Gates, Steve Jobs and Mark Zuckerberg didn't get a degree, so that's proof you don't need a degree to succeed.
But that misses the case of, what about the people with college degrees who did succeed? And what about the case where people without college degrees didn't succeed? And you're only highlighting three people, and I have a little bit of guilt and a little bit of concern that I'm only telling stories about successful people. And so, the data, it's not exactly a scientifically valid sample and conclusion. Do you ever have weird thoughts like that?

Ben Gilbert:
Absolutely. But you're not expressing that it is. I can probably count five-plus episodes in the last couple of years where I've said the phrase survivorship bias on Acquired. I think you wave your arms around, you acknowledge it's a disclaimer. You're not saying, "I studied 10,000 companies from their founding and here's what I learned from those that didn't make it and those that did."
You're saying, "I'm studying remarkable people." I also think, there's a funny comment that I made to a group of startups recently, which is, "You really need to stop looking at the five trillion dollar companies that are out there, the big tech companies as your North Star.
Those are such extreme outliers, and their founders are such extreme outliers that it's so improbable you become one that you should not try to learn from them." It's what, five, six standard deviations from the mean when you look at the founders who became the most fabulously wealthy people in the world, so yeah, a few of those are going to exist.
Of the seven billion people, no, you're almost certainly not going to be one of them. So, you're much better off figuring out, "Well, of all of the wonderful going concerns out there are these profitable businesses that delight customers that grow at a reasonable rate every year that are going to be around for the long term. What can I learn from those businesses and apply those practices in mine?" I think you can always maintain optionality to become the next NVIDIA if you want to.
In fact, NVIDIA is a great example. They were an uninteresting company to most investors and most employees, other than people doing video game graphics cards, for the first twenty years of their existence. And so, I always counsel entrepreneurs, "Go build a good business doing something that you think delights customers and maintain your optionality should you want to pursue the crazy lottery ticket."

Guy Kawasaki:
Okay, I'm not sure Jensen would look at it like that, because it seems like the victors have the ability to reinvent history. So, he always knew that AI was coming, and he was prepping for twenty years.

Ben Gilbert:
But they had a few missed shots on goal along the way of bets they made that were not AI, that were just wrong timing or wrong vision, or they've messed a lot of stuff up. And frankly, what became AI that started as scientific computing and academic computing was something they were working on for, I don't know, eight years or so before the AI revolution. No, even longer, over a decade.
And truly it was not getting traction. And investors were selling the stock and their stock was in the dumps because of it. Jensen's up there saying, "This stuff is the future. I've been working with these supercomputing labs and these professors and when the future we're going to have these models that do X, Y, and Z."
And the market just didn't believe him. The company wasn't doing terribly well in the early 2010s because of it. I also don't think he really knew that AI was going to change the world in this transformational way. I think he thought, "Oh, we can accelerate computing on GPUs in a way that can't be done on CPUs." But exactly what the products looked like; I don't think he saw that.

Guy Kawasaki:
Yeah. Now a lot of people are going to be wearing leather jackets and the whole world is going to change. Unless you consider this giving away trade secrets one podcast to another, I would love to ask you some of the nitty-gritty of Acquired.

Ben Gilbert:
We're an open book.

Guy Kawasaki:
For example, have you ever totaled up about how many hours of work goes into a four-hour episode of Acquired?

Ben Gilbert:
Yes. So, David and I each do about a hundred hours of independent research before recording.

Guy Kawasaki:
One hundred hours?

Ben Gilbert:
One hundred. And then recording day is an approximately ten-hour session where we're each in our home studio, and that ten hours gets edited down to about four hours of content. And that editing process, we have a great audio engineer editor that we work with. And then David and I are saying, "Not this sentence. Yes, this sentence. Rearrange this to go here. Cut these three words, they're extraneous."
We're sort of editing a transcript. That process takes probably about twenty-five person hours for each David and I and probably forty person hours for our engineer. So in total, that's what, 200 hours of research, another twenty hours of recording, so that's 220 plus fifty plus fifty. Yeah, it's a lot of work going into one episode.

Guy Kawasaki:
When you spend ten hours recording through a day, is it because you're constantly doing retakes of the same thing, or are you just discussing Rolex for ten hours?

Ben Gilbert:
There are whole segments that get cut where when we're listening back in the edit, we're like, "You know what? That whole side story we told is just unnecessary and it makes the plot drag and it doesn't pay off in any great way in the analysis later, so let's just cut it." The other part, as you mentioned is retakes. Sometimes David will tell a ten-minute chapter of a story and I'll say, "I think we can do that in four."
Or I will give a long-winded explanation of the way a mechanical watch works, and David will say, "You lost me in here and here. Can you say it tighter?" And so, our four-hour episodes are really our attempt to tell the complete story in as short as we possibly can. And yeah, there's bathroom breaks. There's, "Can you pause for five minutes? I want to eat a sandwich." Sometimes we have to start over because we feel like the magic's not happening the way that we want it to.

Guy Kawasaki:
There may be a future for either one of you in Congress.

Ben Gilbert:
It's true. I've learned to stand here in this exact position at this desk, in this room for ten hours straight speaking.

Guy Kawasaki:
So, you decide to do an episode about XYZ company and then the two of you just pour into it and you read every book, you watch every video, you're just doing research?

Ben Gilbert:
That's exactly right. Think about if all you had to do in an entire month was make a podcast episode, how good could you make it? And that is the thing that wakes me up in the middle of every night is, "Did I leave it all on the field? Did I turn over every stone?" And you're right, as every YouTube video, we read really every important book or every book that's been written about the company that we're studying. Recently, since we've become bigger, we have a lot of access.
So, sometimes we'll talk directly to the company, but oftentimes that's not fruitful and they'll try to just steer it in a direction. So, talk to a lot of former executives, former employees, folks that have held the stock for a long time. You read old investor transcripts, you watch their annual presentations every year at developer conferences or things like that. Talk to customers.
Yeah, it's like the investment process. If you were doing a really, really diligent big decision about having your firm invest in a company, except that we don't actually have to make the investment, we just have to feel like we nailed it when we did the episode.

Guy Kawasaki:
And how do you decide that this company is worth doing this for? Once the decision is made, do you ever get a hundred hours into it and say, "There isn't enough their there?"

Ben Gilbert:
We've gotten pretty good. We used to, that was really bad. It was a big waste of time and heartbreaking when we had to walk away from doing an episode. We've gotten pretty good at saying, "Hey, let's each take two hours today and do initial research and then we'll come back together and commit to," 'Hey, we're for sure doing this as our next episode.'"
We're in that process right now where we have an idea for what the June episode is going to be, but I'm not committed yet. And so, I have a two-hour block later today to look around at what other work has been done on this company and figure out if I think it's a thrilling narrative and there's unique mental models to take away.

Guy Kawasaki:
And at this point, are you buying or selling? Are people reaching out to you and say, "Please do my company." Or are you begging them to cooperate with you?

Ben Gilbert:
No, we probably get thirty emails a day suggesting episodes, or just fan notes. I've blocked most PR firm email addresses, so I actually don't know what their domains, so I actually don't have a great sample anymore. Fifteen of that thirty is crap, pure PR firm garbage where they just say, "This person is going on a bunch of podcasts and they can talk about this, that and that, and you should have them." I'm sure you get these same emails and you're just like, delete, delete, delete, delete, delete.
But then there are very interesting ones where a company we admire and have heard of, it's the CEO reaching out or it's the chief communications officer or the CFO saying, "Hey, I think there's something really interesting here." That is usually not what leads to an episode. We always are a little bit nervous when the company reaches out and says, "Hey, you should cover us." That's usually sort of a negative signal.
But we add it to our suggestion spreadsheet nonetheless. And we've got 500 potential episodes in the hopper at this point. And the process is always David and I coming together after we finish one episode to say, "All right, is there anything in the spreadsheet that lights you up? Is there any conversations you've had in the past week with friends or listeners that lights you up? Or is there anything that has some recency bias to it that you're just currently excited about that we've never talked about before?"

Guy Kawasaki:
If let's say I am the chief evangelist of a company named Canva, and I say, "Listen, two people, students Western Australia, they're teaching kids how to use Photoshop and then all of a sudden they start a yearbook company in a spare bedroom and they figure out it's too hard to make a yearbook, so they create Canva."

Ben Gilbert:
Canva is such an incredible story.

Guy Kawasaki:
I'm being semi-facetious here. So they go up against Adobe and they pitch 300 times. They get rejected because they're in Florida, or it's a female executive or whatever. Do you tell that kind of story and now it has 300 million active users? Is that the kind of arc of a story you're looking for?

Ben Gilbert:
That is totally the type of arc of a story we're looking for. We for Acquired, for our main show, we tend to tell these older company stories at this point. Because we view ourselves primarily as historians, so we really can put on our historian lens and dive back. In the case of a Hermes 170 years ago, in the case of New York Times, something similar. There's always these strange ones with Meta and NVIDIA that are only twenty and thirty years old where you're like, "Gosh, that company's only twenty years old."
But there's a feeling you have that Meta is more of a stalwart in our world today and not a startup. And I think we're waiting until we can tell a story of a company that feels like it's just a fabric of our world, but nobody really knows how it got here. And my feedback for Canva would be, I don't think people feel that way. I think people feel like, "Wow, this is a really interesting innovative company that is better than its incumbent competitors. And a friend just recommended it to me."
I would rather tell a story on Acquired of, "Hey, everyone just assumes Costco has been Costco forever. How did Costco come to be and why is it different than the rest of the world?" And so, we do actually have a second show called ACQ2 that is actually pretty big in its own right now, I think about 75,000 listeners, where we talk to founders who are building the next innovative disruptors in real time to dive into stories like that.

Guy Kawasaki:
It's fascinating. And the number that I hear bandied about is like a million subscribers to Acquired, and the most difficult thing I find about podcasting is getting subscribers. Now, you've been at it for ten years, I've been at it for five. When does the magic happen? Did you break the formula for advertising or social media, or what happened? Are you just organic? Your quality is so great that it just took off? What's the formula here?

Ben Gilbert:
It's such a good question, and I think it's one that David and I ask ourselves a lot. When you look at the chart, it is true that it doubled every year since founding. And that's all organic word of mouth. So, the question is, what causes that? And we have one exception, which is a lot of the growth last year came from this fantastic writeup in the Wall Street Journal. It's the only press I've ever been a part of in any startup or investment firm I've been in where one single article massively moved the needle.
And it was literally hundreds of thousands of new subscribers came from one article. So there was some step change from that. Other than that, the entire growth of Acquired has been, I listened to an episode, I went even deeper in the back catalog. I realized I like this format and it lights up something in my brain, and I want to share it with friends so they can learn something too. Or so I can be perceived as smart for having recommended this. I get some social capital from it.
So, it's telling their friends, it's sharing in Slack communities that they're a part of. It's sharing with their coworkers, it's sharing on social media. And what drives it, I think is the fact that it's a pretty unique product. Most podcasts follow one of three formulas. A, it's two friends chopping it up, having done almost no research and bantering about something of the week. Two, it's scripted drama, so think true crime and stuff like that. And three is interview shows, one person interviewing another person.
And almost no one does the format that we do that we call a conversational audiobook or conversational storytelling where it's two people having done deep independent research and through conversation telling a story.
And I think there's something about the uniqueness of that format and the chemistry between David and I and the fact that people are genuinely interested in these companies that are fixtures of our world, but they're fascinating and hiding in plain sight, that I think comes together to make someone go, "Whoa, that was cool. I want to share it."

Guy Kawasaki:
Like I said at the start of the show, Ben, I am not worthy. I am just in awe of what you have accomplished. Let me ask you, you quickly said you guys edit audio. By any chance, do you do something like use the script and edit text to edit audio, or do you literally listen to the audio and move the slider gently and edit that way?

Ben Gilbert:
Yeah, it is actually the waveforms, and I did the first fifty-ish episode, I should look at the exact number myself, in Adobe Audition.

Guy Kawasaki:
Wow.

Ben Gilbert:
Trying to learn sound engineering. I was okay at it, and then we brought on this really fantastic person that we work with him as a contractor and he is the best in the world at this. And so, the way, we do use the script, but we use it to highlight to our editor, "Hey, here's the parts that we want to cut, and can you go in with your immensely skilled ear and work in a waveform editor and make it sound natural."

Guy Kawasaki:
To make the cut sound natural?

Ben Gilbert:
Yeah, but there's 1,000-plus cuts in episode. The way that you go from ten hours to four is immense surgery on the acoustics.

Guy Kawasaki:
Wow. Madisun is listening to this and she's having palpitations right now.

Ben Gilbert:
I think it's not necessary for most types of podcasts, like this Steve Ballmer interview we did yesterday. We won't edit that that much. I think conversations require less editing. We're effectively trying to create an audio movie, and I think that you need to spend a lot of time in the edit room to do that.

Guy Kawasaki:
Okay, Ben, this leads me an off the cuff remark that I have another metaphor for you. So, not only are you the Harvard Business School, the modern age, I would also say that you are kind of like John McPhee if you know who John McPhee is.

Ben Gilbert:
Heard the name, but please remind me.

Guy Kawasaki:
Yeah, you've checked out John McPhee. He's written entire books about oranges and entire books about a tennis match, and an entire book about making a birch bark canoe. I mean, if somebody said, "How can you make the story of Rolex fascinating?" They might also say, "How can you make the story of making a birch bark canoe fascinating?"
And John McPhee did that for canoes, and you definitely have done this for some older brands. One last question about this techniques you do, which is, how do you do your transcripts? Because they're extremely well done, and I love them, because I'm a deaf person.

Ben Gilbert:
Can I ask you before I answer this question, how do you do a podcast as a deaf person? This is amazing. I didn't know this about you before we started recording. It's really impressive.

Guy Kawasaki:
Well, I have a cochlear implant, so the implant takes you from being deaf to having really lousy hearing. And in fact, it's much easier for me to do an interview like this, because I have audio directly into my head. It's much harder to do it in-person where I'm trying to listen without a direct feed into my brain.
And it's not easy. There's also a real-time transcription happening in Chrome, so that helps me too. But let's just say, not that I'm comparing myself to him, but if Beethoven can compose the Fifth, I can do a podcast. That's my logic.

Ben Gilbert:
It's really cool. It's very impressive, and thanks for sharing that. The way that we do. I mean, I'm so interested in AI that we actually use Claude for a whole bunch of things. But there are certain things that I think I just want to have the highest possible quality with no errors.
And so, we have a human go through and listen to the final podcast episode and create a full correct transcript with correct proper nouns and some research to try and figure out what company that is defunct from thirty years ago that Dave and I are referencing. How do you spell that? We want that sort of accuracy, which is why it tends to take about a week before that shows up on our site after an episode.

Guy Kawasaki:
I feel your pain, Ben, because we interview a lot of professors, and when professors are on the podcast, they start spouting off these studies of Haskins and such and such and such and such. She came up with this study at Columbia in 1965, and so the first pass on our transcripts is a service called Rev.
And then the second pass is a very intelligent woman, who is looking for all those proper nouns, is trying to figure out, "How do you spell that? Who the hell is that? Who is this person from Columbia that this other professor from Wharton just spouted off about?" It's a very challenging thing.

Ben Gilbert:
It is.

Guy Kawasaki:
I don't spend anywhere close to 300 hours on an episode, my God. I think it's a clear message to me that the longer you spend and the harder you work, the better the podcast. You've proven that. But is there a point of diminishing returns? You could spend infinite time making this high quality podcast? Where do you draw the line?

Ben Gilbert:
And if we're not careful, we will. At some point we're going to make a podcast episode every year if we continue with this philosophy. There are examples where we did too much research. I think the Nike example is probably one. We read between David and I, twelve books on Nike, and we kind of lost the story a little bit. And so that was one where we actually needed to restart recording. I think we got two, three hours in and bagged it and said, "All right, let's tell the story a different way."
We got too wrapped around the axle. Our whole life became knowing random things about the history of Nike. And we had not done an episode the previous month, and so we'd spent a lot of time on that. Another one that I think we might've gotten a little bit too deep on was Meta. We had just had Mark do this big interview with us at our live show at Chase Center. We had 6,000 people live in the audience and we're interviewing Mark, so I prepared heavily for that conversation.
And we got to know ten-plus Meta executives as a part of preparing for that, that I also then went and interviewed to prepare for the Meta episode, and David and I each read three books, and we released a six-hour episode. We're never going to release a six-hour episode again.
And I think we found sort of the limit of we were over-researched, we felt like we needed to tell too many stories. The episode, actually, if you listen back to it, I think it's a great episode, but because it's six hours, it's not the most distilled version of the story that we could have told if we had just said, "Okay, we're going to stop now. We're just going to record."

Guy Kawasaki:
Is the Nike episode the one where both your wives said, "Finally I get my husband back?"

Ben Gilbert:
I think that's right.

Guy Kawasaki:
But by any chance, did you interview Tinker Hatfield for the Nike episode?

Ben Gilbert:
I didn't. I watched a bunch of footage of him, but I didn't interview him. You had him on the show?

Guy Kawasaki:
I have not had him on the show, but he's a personal friend of mine. If you ever want to do Nike Two, I'll sit you up with Tinker.

Ben Gilbert:
Awesome.

Guy Kawasaki:
One of the things I find most fascinating about Acquired is that in a sense the two of you have to become experts on so many different things, right? From Birkin handbags, Rolex watches, Porsche, semiconductors, social media. How do the two of you do that?

Ben Gilbert:
It's funny. We become experts up until the moment we do an episode, and then we tend not to keep our expertise. Sometimes we're able to follow these storylines even after we release the episode, but our life is mostly putting blinders on so that we can do the best research we can for the current episode. And so, I haven't stayed up on all of the latest in chip bands with NVIDIA. I couldn't tell you the current state. I can tell you exactly where they were when we did our episode.
I can tell you exactly where they were before we interviewed Jensen afterwards. But there's this trail off period. I could tell you a lot about the new Rolex watch, the Land-Dweller that has come out since we released our episode, because it was still fresh. It was within a month of when we released our episode. But man, way back in the day we did Activision Blizzard, and I know that Microsoft has since bought Activision Blizzard. Could I tell you anything about their product portfolio or any release dates? No.

Guy Kawasaki:
Yeah. When I was in my case reading the Rolex episode, and you guys were talking about all your watches, and I have to say, this thought crossed my mind, and maybe you can talk me in or out of it. When my father was alive, one of the things he cherished was a Rolex, so my sister and I bought him a Rolex President.

Ben Gilbert:
Ah, so cool.

Guy Kawasaki:
And so yeah, this is an Eighteen-karat gold Rolex President, and he never used it. So it's in the original box in our house for, I don't know, forty years or something.

Ben Gilbert:
Oh, wow.

Guy Kawasaki:
And I know it's extremely valuable, but after I read your episode about Rolex, I said to myself, "Screw it. Maybe I should just start using his watch in his honor." What do you think I should do? You think I should use his Rolex President?

Ben Gilbert:
Watches are meant to be worn. It's worth probably taking it to an appraiser or a dealer so you can make an informed decision on whether you want to change its value or not. Just by wearing it might change it some. By wearing it, if you risk scratching it or something, that'll change it a lot. But to me, you only have precious moments on this Earth. And if you can enrich your moments on this earth by having something that makes you feel closer to your dad and your family and his memory, what is money?

Guy Kawasaki:
Okay, well, maybe I'll become so famous because of this episode with you that me using the Rolex and discussing it on the podcast will make the Rolex even more valuable even though it's used. How's that?

Ben Gilbert:
Could be. We'll see.

Guy Kawasaki:
So listen, I need to get a little dark for a little bit, all right?
I just want to know something, like you did two episodes about Facebook in 2016 and 2024, and if somebody had told you Mark Zuckerberg is going to end all the DEI programs, he's going to stop supporting DEI causes and he's going to donate to Trump's inauguration, he's going to be part of the inauguration photo shoot, what would you have said?
Would you say that is inconceivable? I mean, that's just Mark. His whole skill is to set himself up to be successful and lucky.

Ben Gilbert:
I think my final words on our big six-hour Meta episode last year were, “This company moves like water.” It finds a way. It figures out how to run downhill where it needs to go, and it will adapt its product suite and its position and the role that it fills in people's lives in order to do whatever it needs to do to be successful.
With that lens, basically nothing Mark does would surprise me. I think he's always trying to build the best company he can, and there's a lot of things that he'll do or not do to achieve that end.

Guy Kawasaki:
The underlying question therefore is what is the duty of the management of a company? Is it to the shareholders, the employees, the customers, or more esoteric things like art and fashion and innovation?

Ben Gilbert:
The duty is to the people you just mentioned, to the shareholders, to the employees, to the customers and to your community. And I think often those things are in conflict. In fact, in every case they're in conflict. I want to run a better business so I can actually generate some profit. I'm going to charge you more money.
That is anti-user, that is anti-customer. I think you are witnessing in real time the tension between the things that he is trying to do to stay in political favor to make sure that there's nothing that happens to his company that would put its future at risk, while also trying to do the things that he needs to do for shareholders, for employees, for customers. And they certainly don't always get that right, and they certainly change their mind on things.
I think you'll talk to a lot of people who are a big critic. "Oh, so-and-so shouldn't have donated to this inauguration." I'm not a critic of that. I think it's in vogue right now to be a critic of things like that. And I think every narrative is always a little bit overbought and then a little bit oversold, and I just try to stay a little bit more moderated.
And I'm not a superhuman, so I'm not that great at that. But whenever everybody is all worked up about something, I always try to remind myself, "There's something here, which is why people are worked up. But something here is probably not as big a deal as everyone is making it out to be." I think it is possible for a company to cozy up too much to administration to try to curry political favor.
And I think the more cronyism happens, the more that happens and that erodes our democracy. But I don't think showing up at an inauguration and donating a million dollars, which is insignificant actually to both the donor and the recipient in this case, is that big a deal.

Guy Kawasaki:
I have one last question for you, and I'm taking a cue from what I read on your podcast, which is, if I don't ask about a particular topic, what would that topic be that means that I whiffed this interview?

Ben Gilbert:
This is a good question that I should have been prepared for, because this is my question.

Guy Kawasaki:
Don't you hate it when you get your own wisdoms put back in your face? It happens to me all the time.

Ben Gilbert:
I think the most interesting one is, okay, Acquired has had ten years. What would need to be true for it to have another ten great years? Or is this peak Acquired? And that's the thing that Dave and I are always asking ourselves. So, my answer to that is, Acquired will continue to need to change to not be stale. And the scary thing is, we never know exactly what it needs to change into.
And so, it is always somewhat of a gut decision at any given point to expand or try a different focus or try a slightly different format. And we try to take as many cues from the audience and from the data as we can, but it's ultimately a gut decision. So, I think the success of that, or the answer to that question will be judged by how good is our gut at continuing to evolve and change and stay fresh and stay interesting over the next decade?

Guy Kawasaki:
Well, Carol Dweck is up at Stanford right now. She's smiling at that answer, because that basically says it's all about the growth mindset, right? To be relevant, to be successful. Ben, this has been a most educational episode of Remarkable People, because as you can tell, I'm really curious about how you do your work.
And not everybody who listens to this podcast is a podcaster, but if you are a podcaster, you heard how much prep goes into his work. And I don't know anybody who works that hard on a podcast, which is why Acquired is such a great, great platform.
I just want to thank you, Ben. I want to thank Buzz Brueggemann for helping me get to you and get you on this podcast. And my podcast staff is Madisun and Tessa Nuismer. I have two sound engineering; I love my sound engineers. It's Shannon Hernandez and Jeff Sieh. So, that's my crew, and you are my hero, Ben Gilbert, so thank you very much again.

Ben Gilbert:
Thanks so much, Guy. I appreciate you having me on.