EVERY SPOKEN WORD
150 min read · 30,047 words- 0:00 – 3:30
Intro
- DSDavid Senra
I found this guy who tweeted something a couple days ago or whenever. It was hilarious. He goes, "Most people's alarm clock is David Goggins telling them to wake up and get after it. My alarm clock is David Senra yelling at me, telling me to be like Edwin Land." [laughing]
- BGBen Gilbert
[laughing]
- DSDavid Senra
I was like, all right, repetition works.
- SPSpeaker
Who got the truth? Is it you, is it you, is it you? Who got the truth now? Is it you, is it you, is it you? Sit me down, say it straight, another story on the way. Who got the truth?
- BGBen Gilbert
Welcome to this special episode of Acquired, the podcast about great technology companies and the stories and playbooks behind them. I'm Ben Gilbert.
- DRDavid Rosenthal
I'm David Rosenthal.
- BGBen Gilbert
And we are your hosts. Today's episode is our next installment of Acquired Sessions, a video format on YouTube that we started playing with last year. Our guest today is David Senra of the Founders Podcast. David is quite possibly the only person we know who is more obsessed than us- [chuckles] ... with business history and the lessons that great founders teach us. David, David Senra, that is, has read hundreds of founder biographies and done deep episodes on them all.
- DRDavid Rosenthal
I don't know that I'm at hundreds yet as me, David, but I, I'm definitely in dozens.
- BGBen Gilbert
[laughing]
- DRDavid Rosenthal
I aspire to be at hundreds, but David Senra is just one of our closest podcaster friends, and friends period, out there. His show is awesome. Here on this episode, we had him out to my living room here in San Francisco, and we had just a awesome, really fun multi, multi-hour conversation, just like the ones that he and I have scheduled every month on Zoom when the mics are off. And it was super organic, super unstructured. We covered a ton of ground, including that, I think two nights before we recorded, David was just coming up from LA, where he had dinner with Charlie Munger, and so we spent a lot of time talking about that, Charlie's influence on David, his and Warren's influence on all three of us, a bunch of thoughts on advice generally. And as you can imagine, David just sprinkled dozens and dozens of historical examples and founder stories throughout the episode.
- BGBen Gilbert
It is crazy. Every time someone's making a point, he'll dive in, "This is just like that thing Edwin Land said that one time." [chuckles]
- DRDavid Rosenthal
Or David Ogilvy, or Coco Chanel, or who have you.
- BGBen Gilbert
David is definitely close with the eminent dead. I will say, after editing this episode, I had one enormous takeaway: David Senra is really, really into podcasting, so get fired up to meet him on his level. All right, quick things: go follow ACQ2, brand-new show. Search i- any podcast player, available for free. Become an LP. There is voting going on right now for our next episode, which LPs all have input on, and for every new LP that joins, we will shoot you an email to your inbox. Voting closes about a week after this comes out, and we are straight-up picking whatever you tell us the next episode should be, with really no editorial from us, so help us direct the next episode. Join the Slack. It is one of the only places on the internet with this super high level of incredibly thoughtful discussion by well-connected, kind folks with a deep appreciation for history. People meet co-founders, they find jobs, and they get nuanced takes on the news of the day in there. So join at acquired.fm/slack. Lastly, this show is not investment advice. David and I may have investments in the companies we discuss, and this show is for informational and entertainment
- 3:30 – 6:00
David’s time with Charlie Munger
- BGBen Gilbert
purposes only. Now, on to Acquired Sessions. So David, do you wanna tell us who you had dinner with the other night?
- DSDavid Senra
I had a three-hour dinner with Charlie Munger-
- BGBen Gilbert
That is awesome
- DSDavid Senra
... where I could ask him any questions that you want. Well, first of all, I guess we should back up. It's like there's a reason that he's so admired, right, by so many people, but for, for me particularly, um, you get to lot- meet a lot of really interesting people because of the work that we do, right?
- BGBen Gilbert
Yeah.
- DSDavid Senra
And so that's, like, a, a, a blessing and something that I know we've had conversations in the past that we deeply appreciate. But Charlie's a different level for me. Like, I literally think of him like the wise grandfather I never had.
- BGBen Gilbert
Mm-hmm.
- DSDavid Senra
Um, you know, I've met all kinds of people. I don't really get, like, nervous or starstruck. I was legitimately, like, shaking the day before. I was like, "I cannot believe..."
- BGBen Gilbert
[chuckles]
- DSDavid Senra
I didn't, I didn't wanna tell that many people, 'cause, like, this is just... There's no way this is gonna happen. Like, I just, I won't believe it till it actually happens. We, we do very similar work, right? Where it's just like, how many people have spent six, seven years, tens of thousands of hours, reading hundreds of books about the history of entrepreneurship and investing, and then not only reading it, taking notes on it, making a podcast-
- BGBen Gilbert
Us, and Charlie, and Warren. [chuckles]
- DSDavid Senra
Yeah. [chuckles] And so what- and the reason I bring that up is because you think about all the different companies and founders you guys have studied, all the different companies and founders that I've studied, right? And, like, even amongst a, the rarest group of people, Charlie still stands out.
- BGBen Gilbert
Yeah.
- DSDavid Senra
And the crazy thing is, he's 99, right? And so I get there, and we start off in his library, which is, like, the best place for me that you could possibly see. And so-
- DRDavid Rosenthal
How... Set, set the stage more. How, how big is the library? Like, how many books are we talking about?
- DSDavid Senra
It's... And so it's not... So his, uh, his f- one of his family members was there, too, and she's like, "Oh, this is, like, nothing." [laughing] Like-
- DRDavid Rosenthal
This is, like, the front room. Wait till you see the back.
- DSDavid Senra
Yeah, so it's like, it, it's similar to, like, the room we're in. Like, you know, very similar size, and, you know, s- floor-to-ceiling shelves. And so I'm with a, a gr- a small group of friends. In fact, uh, mutual friends from ours. So the people that set this up for us, or for me, was, uh, Andrew Wilkinson and Chris from, the founders of Tiny-
- BGBen Gilbert
Mm
- DSDavid Senra
... are mutual friends. And, um, and so we're sitting there, and there's actually a funny thing, where it starts out, and they, they know both Warren and Charlie. They've talked to them before, so they go right into it. And then, like, I'm sitting there, and I had this whole list of probably, like, 25 questions. [laughing]
- DRDavid Rosenthal
I was gonna ask if you, like, prepared in advance. I know you did.
- DSDavid Senra
I never got the chance to open my phone. [chuckles] 'Cause I was just sitting there. I was like, I'm looking at him, and he's, you know, very close, like, you know-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... maybe a little bit further from me than Ben was.
- BGBen Gilbert
Oh, that would feel super disrespectful to, like, take out my phone to-
- DSDavid Senra
Yeah, that, too. And
- 6:00 – 9:00
Henry Flagler after Standard Oil
- DSDavid Senra
I had, you know, read every single book on Charlie. I watched all of his videos. Like, I have studied this guy forever.... and so every time he had said, "Hey, read this book," I go and read the book.
- DRDavid Rosenthal
Mm.
- DSDavid Senra
And then I see a bunch of the books that he has recommended behind him. So people are like, "Oh, was he as like you expected?" Like, they say, "Hey, be careful. Don't meet your heroes," right? It's like, he was unbelievably gracious.
- DRDavid Rosenthal
Mm.
- DSDavid Senra
You know, unbelie- Like, uh, I was like, "Hey, Charlie, do you mind if I take a look at your bookshelf?" Right? He's just like, "Do whatever you want." Just unbelievably polite. Still, like, biting intellect, ferocious intelligence.
- DRDavid Rosenthal
At 99. [chuckles]
- DSDavid Senra
At 99. So we were talking earlier, um, uh, downstairs, where the scary thing about Charlie is... I remember asking a question about Henry Kaiser, uh, this guy that was super famous when Charlie was younger. He built, like, 100 companies, built the Hoover Dam. Like, he was as famous in his time as, like, Elon Musk is today, right? But no one knows who he is. Um, and I was asking questions about Charlie in the book, and his recall is just insane. To the point where I asked him, I go, "How do you know all this, Charlie?" He goes, "I knew his partner." [laughs] And then he starts telling stories about being- knowing, like, having a relationship with Henry Kaiser's business partner, and then all these-
- DRDavid Rosenthal
Oh!
- DSDavid Senra
... three hours of just unbelievable stories. And then I go, "Charlie, like, how do you remember all this stuff? Like, do you write wor- like, do you take notes? Do you re-read the books over and over again?" He's like, "Nope." And all I could think, I was like, imagine.
- DRDavid Rosenthal
Wow.
- DSDavid Senra
That guy's mind at 99 is still so sharp. I had brought a gift for him, because he's, he talks about, like, um, Rockefeller all the time. I bought him this special edition, uh, centennial edition version of Henry Flagler's biography.
- DRDavid Rosenthal
Oh, Flagler!
- BGBen Gilbert
Oh.
- DRDavid Rosenthal
Yes.
- DSDavid Senra
So I, I live in Miami. The, the guy, Les Sandford, I think is his... the author of that book, um, he is good friends with... There's only, like, one local bookshop in Miami called Books & Books, and so Les is a local author who's good friends with the owner of that bookstore, so they did a sp- you can't get this book anywhere else.
- DRDavid Rosenthal
Wow.
- DSDavid Senra
It's a special edition book.
- DRDavid Rosenthal
'Cause Flagler moved to Florida later in life, right?
- DSDavid Senra
After the Standard Oil thing.
- DRDavid Rosenthal
Yeah, yeah.
- DSDavid Senra
Yeah. That- he, he's got a fascinating story. We talked about that, where he ma- he, unbelievably wealthy because of Standard Oil.
- DRDavid Rosenthal
Yep.
- DSDavid Senra
He's, you know, 50, 60, 70 years old when he's doing this, and he's just like, "Oh, what am I gonna do now? I'll build an entire state." When he gets to Miami, Miami is little less than 500 people living in a swamp. Because you can't live there. There was no AC at the time. And so then he builds the, the world's first, uh, railroad-
- DRDavid Rosenthal
Right
- DSDavid Senra
... over for connecting s- uh, the Florida Keys. He just essentially, like, you read that book and you're like, "Oh, humans have no limits other than the ones we put on ourselves."
- DRDavid Rosenthal
Mm.
- DSDavid Senra
And so that's what Flagler does. He just stretches it. And he does some terrible things, too, where it's like-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... wanted to find a way to divorce his wife, so he literally moves to another state, 'cause you couldn't get a divorce in New York. Bribes the, the, the, the government of Florida. They create the Flagler Law, which allows him to get a divorce. Then he does that, like, a few, I think a few times. I think he's, like, in his 70s, and he marries, like, a 30-year-old.
- DRDavid Rosenthal
[chuckles]
- 9:00 – 11:30
What makes a great biography, and how to capture all sides of complex characters?
- DSDavid Senra
everything else.
- BGBen Gilbert
This is, like, one of my... the things that I keep learning from Founders Podcast, and I'm curious if you do it intentionally or if you, like, try not to do it, but, like, every single time I'm like, "Oh, people aren't perfect." Like, n- none of your heroes are perfect. And do you find yourself, like... 'Cause we, we run into this on Acquired a lot, where, like, it's not as fun to tell stories about terrible people, and so you, you, you, like, don't want to show someone's negative side-
- DSDavid Senra
Mm
- BGBen Gilbert
... as much, because it doesn't, like, it's just, it-
- DRDavid Rosenthal
Well, we, we, like, we fall in love with them, too-
- BGBen Gilbert
Right
- DRDavid Rosenthal
... when we're doing that.
- BGBen Gilbert
Right, and you're like, "Wow, they're the most extraordinary person on this one axis to ever live," and we, we should talk about how they're a flawed person in many ways, but it's not fun to dwell on. Like, you kinda wanna, like, move through that and be like, "Yep, yep, they were flawed. Here's the next amazing thing that they did." Like, how do you handle that?
- DSDavid Senra
Like, you know how a normal biography is written, right? It's like, way too much family history. Like, I wanna know some family history. I don't want five generations back.
- BGBen Gilbert
Right.
- DSDavid Senra
Stop. Like, I don't wanna know the origination of their last name. I don't need that. I wanna know, like, wh-
- BGBen Gilbert
And you're like the most qualified person in the world to critique a biography [chuckles] writing style at this point, so.
- DSDavid Senra
[chuckles] So why we're reading it is, like, everyone wants to know the climb, right?
- BGBen Gilbert
Yes.
- DSDavid Senra
It's like, how did you... You guy- I just went through your entire... To get part of the prep for Charlie is listening to all of your Berkshire episodes, right? Where you guys do a fantastic ep- uh, job on this, 'cause, like, the first two is, like, the young Charlie, the young Warren.
- BGBen Gilbert
Yeah.
- DSDavid Senra
So I would literally, and I've done this forever, it's like I don't- when you think of Warren Buffett or Ben Franklin or George Washington or anybody that's super famous, when we see them, it's like, "Oh, who's the Ben Franklin on the $100 bill," right?
- BGBen Gilbert
Yeah.
- DSDavid Senra
Or, "Who's the Washington on the dollar bill?" Or, "Who's Buffett at the, the meeting in Omaha?" It's like, no, no, that, that's the guy that is, is enjoying the fruits of the person-
- BGBen Gilbert
Right, right
- DSDavid Senra
... who actually built the empire.
- DRDavid Rosenthal
That's the... Yeah.
- DSDavid Senra
I go, I go and stare at pictures like a freak-
- DRDavid Rosenthal
[chuckles]
- DSDavid Senra
... at, like, of young Charlie Munger when he was, like, 38, or young Warren Buffett.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
Right? They, they, they were like us!
- DRDavid Rosenthal
It's a statement, are-
- DSDavid Senra
They look like they were young people once.
- BGBen Gilbert
Yeah.
- 11:30 – 13:30
Studying history is a form of leverage to achieve success
- DRDavid Rosenthal
Like, this is the right way to study things.
- DSDavid Senra
I think- I'm glad you brought that up, because I think this is why people get a lot of value, and I don't want it to make us about, "Hey, this is an Acquired Founders Show." The reason that some of the people in our audiences are the most successful people in the world, they're all reading biographies, they're all studying history of, uh, of business. I told you guys, uh, a few weeks ago, I had- I was very lucky to have a two-hour one-on-one lunch with Sam Zell, that I didn't think was possible. What I realized in that conversation is, like, you don't make- you don't... Sam Zell sold his company for almost $40 billion, right?
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
$38 billion, whatever it was. It's like, you don't build a company, sell it for $40 billion, and then learn all this shit. It's like he was doing this since he was a, since he was young. We were talking, in his autobiography, he talks about-
- DRDavid Rosenthal
Well, we talked about... I, I think my favorite episode of your podcast-
- DSDavid Senra
Yeah
- DRDavid Rosenthal
... is the Kobe Bryant episode. [chuckles]
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
'Cause, like-... this is what these guys are doing. They're like Kobe Bryant.
- DSDavid Senra
They're watching game tape.
- DRDavid Rosenthal
They're watching game tape. They're working on the fundamentals from the time they're 12 through the time they die. They don't stop.
- DSDavid Senra
I think that's what, um, we're listening to Acquired and Founders is, is you're watching game tape of history's greatest entrepreneurs. Sam did this when he was younger. But th- this ties together where, um, Bill Gurley had a, a fantastic quote about this, a tweet about this, when all that crypto was going crazy, and, like, the run-up, and people were getting rich. And he's like, "One thing I don't like..." And I'm paraphrasing, 'cause I don't- I wasn't expecting to talk about this. He's like, "I don't like that these young- y- the younger people denigrating the people that came before them."
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
And he's like-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... he made the point that none of the, none of history's greatest entrepreneurs and investors did that. They had the opposite perspective. All of them had idols. You just made the point. You can't understand Jeff Bezos until you study Sam Walton. You can't understand Sam Walton till you understand J.C. Penney, and Sol Price, and all these guys.
- BGBen Gilbert
And even their contemporaries. Like, the point that Walton always made was, "I don't think my competitors are stupid. I wanna go shop my-"
- DSDavid Senra
Yeah
- BGBen Gilbert
"... competitors and get all of their very best insights, and then bring them into my store."
- DSDavid Senra
Yeah, 100%. They, they're learning machines.
- BGBen Gilbert
Yeah.
- DSDavid Senra
And so you get to Charlie's going... Tying this all back to this, you get to Charlie's bookshelf, and it's just biographies I've never even heard of, and I do this for a living! [laughing] I do it for a living. I was like, "What is this book?"
- 13:30 – 21:00
How do we figure out what the true story is for an episode we're doing?
- DSDavid Senra
And then I started looking. I was like, "Oh, I'm just taking picture after picture after picture." I was like, "I'm ordering every single one."
- BGBen Gilbert
So we're talking about this idea that, like, that, uh, the way to get truth is to weave together the tapestry of all of history's stories of things that are adjacent, to understand, like, how this opportunity to start some business came to be. And you always have to r- like, all history is revisionist, and all history-
- DSDavid Senra
Mm-hmm
- BGBen Gilbert
... is biased. And so I think one of the hardest things about making an Acquired episode is figuring out, like, when we're looking at a source, like someone giving an industry talk who works at a company, or, like, a biographer who chose to dedicate, you know, two years of their life to writing this book after working at Newsweek and covering the sector forever, is, like, trying to mentally account for and discount f- from whatever bias and perspective they're coming in with to create whatever the source material is that we're using to then incorporate into our version of-
- DSDavid Senra
Yeah
- BGBen Gilbert
... here's how this thing happened. Which is- that's like... I think it's the hardest part about what we do, and I'm curious if you ever think about that.
- DSDavid Senra
I think about it all the time, 'cause people are like, "Oh, like, survivorship bias or revisionist history," and everything else. It's like, here's the problem, like, we, humans don't see things as they are. We see them as we are. So, like, we could have this super long conversation between the three of us right now, then go in the other room and write down, you know, what just occurred.
- BGBen Gilbert
Yeah.
- DSDavid Senra
And every single version is going to be different, because it's viewed through all of our experience, the way we think, the, the words we use. And so what I'm looking at is, like, when I'm reading about Sam Walton, right? It's just, like, uh, the, the, the, the story we both hit on in all the podcasts, 'cause I've done a bunch of podcasts on Sam, too, where it's like the guy's pissed off. He's just, like, driving store to store on these, like, mountain roads, taking forever, so he buys the plane. And he realizes-
- BGBen Gilbert
Right
- DSDavid Senra
... like, "Oh, this is a massive advantage, 'cause I'm doing something my competitors aren't," right? "I'm flying over." And you guys mentioned it, too, which I thought was hilarious.
- DRDavid Rosenthal
Sideways. [chuckles]
- DSDavid Senra
Yeah. And then he just lands, and he's like, "Who owns that? Le- let me land," and I- and then he, he, you know, buys for action. So he's like, "We're gonna negotiate right now. I wanna buy it from you." And so my point is just like, okay, yes, that most likely occurred, but what is the idea behind that? It's do- you can have an advantage by doing something your competitors are not doing, right?
- BGBen Gilbert
Yeah.
- DSDavid Senra
Um, and it... This ties so together what you're, uh, what you just said, is like they all learned from somebody else. When we're reading these books and listening to these podcasts, it's like, "What's the idea I can use in my life?" We're not building the next Walmart. There's no way, if we read Titan, that we could tell, did this actually happen?
- BGBen Gilbert
Right.
- DSDavid Senra
I don't know, but I'm looking for the ideas behind it, not, oh-
- BGBen Gilbert
Yeah
- DSDavid Senra
... I can-
- BGBen Gilbert
Right
- DSDavid Senra
... I'm gonna verify for every single word in this book. That's ridiculous.
- BGBen Gilbert
Right. And it, the, the truth is always... It is always the case that the, a clean narrative is grafted onto a fact pattern.
- DSDavid Senra
Mm-hmm.
- BGBen Gilbert
And it's like, okay, well, what I care about is the lessons I can learn from the clean narrative, not, uh, uh, does the fact pattern... If, if you had all the facts in totality, did it necessarily mean that it, you know, this was premeditated? It's like, eh, whether it was premeditated or not-
- DSDavid Senra
Yep
- BGBen Gilbert
... you know, the f- the facts are the facts, and, like, maybe I can duplicate it-
- DRDavid Rosenthal
Which is similarly-
- BGBen Gilbert
... in a different realm
- DRDavid Rosenthal
... for what we do. I mean, on Acq- I think on Acquired more than you, but especially 'cause you will do multiple episodes of different books on the same people, right?
- DSDavid Senra
And multiple episodes on the same book.
- 21:00 – 22:00
Silicon Valley should focus more on durability than growth
- DSDavid Senra
way you have 90%.
- BGBen Gilbert
Right.
- DSDavid Senra
Because, like, uh, the time.
- BGBen Gilbert
Right.
- DSDavid Senra
Like, the-
- BGBen Gilbert
The instincts.
- DSDavid Senra
I was just rewatching, uh, Peter Thiel's talk at, uh, Y Combinator, where he says, "Competition is for losers."
- BGBen Gilbert
Oh, yeah.
- DSDavid Senra
And he goes, "One thing that we do in Silicon-
- DRDavid Rosenthal
I haven't seen this one.
- BGBen Gilbert
It's a classic.
- DSDavid Senra
"One thing we do in Silicon Valley is we overrate, overvalue growth rates and undervalue durability."
- BGBen Gilbert
Mm.
- DSDavid Senra
And he's like, "That doesn't make sense for a technology company because all your profits, the vast majority of profits, are 20 years in the future. And so if you're trying to optimize for growth, and that, that, that over-optimization can cause your company to go out of business, you're never gonna collect that. You optimize for durability first, dummy." Like, that's to me-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... like, my interpretation of what he's, what he's saying, right? Yeah, so you're gonna get, you know, 1% probably.
- BGBen Gilbert
Yeah.
- DSDavid Senra
Maybe 5%.
- BGBen Gilbert
But that's still enormous leverage, 'cause you read it in five hours, and he took 50 years to accumulate everything.
- DSDavid Senra
Well, it's, it's-
- DRDavid Rosenthal
And it's Sam Walton's wisdom. [laughs]
- DSDavid Senra
And it's what you do with the idea.
- DRDavid Rosenthal
I know you've talked about this before, but, like, what was, what was the moment where you were like, "I'm gonna, I'm gonna start this podcast?" Like, it's crazy, right, what you do. You, you talk to a microphone yourself every week.
- DSDavid Senra
Yeah, um. [laughs] My friend-
- DRDavid Rosenthal
Not that I think you're crazy.
- DSDavid Senra
Oh, I definitely am.
- DRDavid Rosenthal
You, you are, but in a good way.
- DSDavid Senra
No,
- 22:00 – 26:10
How David got into reading biographies and podcasting
- DSDavid Senra
I definitely am nuts, for sure.
- DRDavid Rosenthal
[laughs]
- DSDavid Senra
Um, and that's g- gonna be, like, we could talk about, um... Did you guys read Jeff Bezos's last shareholder letter before he-
- BGBen Gilbert
Yeah.
- DSDavid Senra
The one of the, the best lines he has is at the end. He's like, "Differentiation is survival." And so, like, think about that, like, how hard... Like, they say, let's say somebody says, "Damn, I love what Ben and David are doing. I'm gonna do the exact same thing." They can jump in and try to do that, right?
- DRDavid Rosenthal
Yeah, right.
- DSDavid Senra
But you have six years of experience-
- BGBen Gilbert
Right
- DSDavid Senra
... you have 600 hours out there.
- BGBen Gilbert
Right, you have to, you have to counterposition against us.
- DSDavid Senra
You have-
- DRDavid Rosenthal
Yeah.
- BGBen Gilbert
Or address a different audience, or-
- DSDavid Senra
Exactly.
- DRDavid Rosenthal
Which, by the way, they definitely should. Every time I talk to somebody who wants to start, I, I... Without fail, I'm always like, "You absolutely should do this."
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
And, and you will, even if you never succeed in terms of any, like, numerical success or, like, you will succeed because you are learning, like-
- DSDavid Senra
So being a nut job and completely crazy is, I think, makes you harder to compete with. And it's also, it, it... We're gonna go all over the map here, but it's impossible not to be that. Like, think about how steeped you guys are in the same information that I am, where it always says, "Oh, you're the sum of the first f- of your five friends," or whatever, right? Well, it's like, it's also, like, what you, you know, some of your podcasts you listen to-
- BGBen Gilbert
Right
- DSDavid Senra
... and the books you read. And so what happens-
- BGBen Gilbert
Oh, it's your five friends, including your parasocial relationships.
- DSDavid Senra
And so now what happens is, like, you mentioned, dude, like, you only read, like, one book about him, you'll go crazy. And so what happens is, when I'm really interested in somebody, I will... I listen to Bill Gurley. Again, I just take advice from people who are smarter than me. Bill said, "Go collect everybody, everything you can." Okay, good, I'll do that. This is ve- these are simple ideas.
- BGBen Gilbert
Yeah.
- DSDavid Senra
And so I'll find somebody that's interesting, I'll read everything about them. And so with Charlie, I have, like, a little Charlie Munger on my shoulder. I have a little Steve Jobs, a little Edwin Land, a little David Ogilvy, Estee Lauder, Coco Chanel, all these people that have been heroes of mine. James Dyson. And so now I'm presented with a situation, it's like, what would they do? And you'll have a... If you read and spend, and absorb everything that's out there about these people, like, you'll have an idea of, like, how they would respond. Did you guys ever read Ken Kocienda's book, Creative Selection?
- BGBen Gilbert
Uh-uh.
- DRDavid Rosenthal
No.
- DSDavid Senra
About the... Oh, that's shocking, that you guys haven't-
- BGBen Gilbert
He, he worked on the original-
- DSDavid Senra
He-
- BGBen Gilbert
... human interface for the iPhone.
- 26:10 – 36:00
What were each of their influences before starting Acquired and Founders?
- BGBen Gilbert
and, and something I've never asked you in all the hours we've spent. This is crazy, this is the first time we've met in person.
- DSDavid Senra
Yeah.
- BGBen Gilbert
Like, we've spent hours, and hours, and hours on Zoom. Uh, h- how did you, like, decide that this is what you were gonna do with your time on this planet? And, like, how did... What led to this?
- DSDavid Senra
Okay, so [scoffs] I... You know, Jer- our mutual friend Jeremy from Formula of Tiny.
- BGBen Gilbert
Yeah.
- DSDavid Senra
Um, I just spent, like, s- a bunch of hours with him. He was in town. In one sentence, he, like, uh, he psychoanalyzed me better than anybody else ever has. He goes, "You didn't have any mentors growing up, so you, like, you have... Then you took it to, like, this extreme." And he said it more, much more eloquently than I am, but he's like, "You didn't have any mentors, so I view your career as, like, this psychopathic, uh, search for, like, mentors that can help you, you know?" And so, like, to answer your question, it's like, I don't wanna go into too much detail here, but, uh, like, I've only had one habit my whole life, and that was reading. I was reading for as long as I can remember. Uh, my mom passed away from breast cancer a couple years ago, and she- we didn't have, like, a lot of money. Like, long story, but, like, I was the first person not only to graduate college, but, like, high school in my family. Like, I came from a family of, like, unfortunately, both sides of the family, like, no education, a lot of, like, just bad habits. So [chuckles] I, I, identify with a lot of what Charlie Munger says, because he essentially observes bad behavior and then tries to do- do the opposite, right?
- BGBen Gilbert
Mm-hmm.
- DSDavid Senra
So I was just... Let me give you an example. I was just up in Canada, um, actually at an event f- uh, Andrew Wilkinson was hosting for a bunch of entrepreneurs, me, Shane Parrish from The Knowledge Project, and, um, and Farnam Street was up there, Ben Wilson from How to Take Over the World, and we were doing this panel together. And Shane's the moderator, and we don't know what we're gonna talk about beforehand. And so Shane asks the question, he's like: "Oh, what, um, what did you learn most from your upbringing?" Or something like that, right? And I go, "I learned not to do cocaine and to graduate high school."
- BGBen Gilbert
[chuckles]
- DSDavid Senra
Like, so that kind of thing, right? And so there was just a bunch of anti-models. I thought about this as I was walking through the Tenderloin [chuckles] this morning in San Francisco.
- BGBen Gilbert
[chuckles]
- DSDavid Senra
And I was like, "I should have do this walk with my daughter as the best-
- BGBen Gilbert
Mm. Mm.
- DSDavid Senra
... Like, 'Hey, this is why you don't do drugs.'
- BGBen Gilbert
Yeah.
- DSDavid Senra
Like, this is the perfect example of, like, you avoid- you observe bad behavior, and then you do the opposite. So long story short, I've always been obsessed with reading. Like, one of the best things my w- my, my mom ever did was, even if we didn't have money for books, she would take me to the bookstore and just sit there. Like, you know, bookstores are so cool-
- BGBen Gilbert
Yeah
- DSDavid Senra
... because they just let you read. They don't- no one comes to you and is like, "Hey, you've been reading for an hour," like, "You gotta get out of here," you know? And just read, and read, and read. So I- I-
- BGBen Gilbert
Was there anybody who, like, introduced you to reading and books, or you just, y- like, there was just something about you-
- DSDavid Senra
Sounds like his mom. Yeah, but no, she's n- she wasn't a big reader. The only thing she read was the Bible. Um, there was no books in the house when I was younger, ever, so my parents-
- BGBen Gilbert
How could you be like-
- DSDavid Senra
I, I can't answer that
- BGBen Gilbert
... "Mom, take me to the bookstore?"
- DSDavid Senra
I can't answer that. All I can say is, like, my wife knows- has known me for 15 years, and her thing, what she says is... She, like, likes my family and gets along with them, but she goes, "How did that come from that?"
- BGBen Gilbert
[chuckles] I had-
- DSDavid Senra
She's like-
- BGBen Gilbert
He, it, it sounds like you have a classic, like, you're the one who made it out story.
- DSDavid Senra
Sam Hinkie, our mutual friend, actually gave me the way to think about this, and it's called the founder of your family, right?
- BGBen Gilbert
Mm.
- DSDavid Senra
And it's the person that, like... And I used to call them, and it was a terrible name, but generational inflection points. [chuckles] Because you'd read this in a biography where you have, like, generation after generation of just not good things happening, and then one person just says, "Fuck this. It stops now."
- 36:00 – 38:00
How to suck less over time
- DSDavid Senra
into an r- a pod-
- DRDavid Rosenthal
An MP3.
- DSDavid Senra
An MP3 that you could publish-
- DRDavid Rosenthal
You could download and put on your iPod.
- DSDavid Senra
This is way before-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... like, anything. And so-
- DRDavid Rosenthal
It's so wild how things have... I mean, you know, we're here now in this recording setup that we have here, you know, with thousands of dollars of gear, and like-
- DSDavid Senra
Yeah
- DRDavid Rosenthal
... we start- I, I remember when we first started, I don't think you'd let me do this, but I was like, "Well, why don't we just talk at the computer and, like, set up QuickTime?" [chuckles]
- BGBen Gilbert
Dude, when I listen back to our first few episodes, like Pixar, and I'm, I'm like, we, it sounds like we were just talking at the computer. [chuckles]
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
Well, we basically were.
- DSDavid Senra
Yeah. That's, that's why when people are like, the, I have a lot of psychos that, they're like, "I'm... I start on number one, and I go all the way through." I'm just like, "Oh, like, please don't."
- DRDavid Rosenthal
Yeah, yeah. [laughing]
- DSDavid Senra
"If you're gonna ha- if you're gonna do, like-"
- DRDavid Rosenthal
Like, I wanna, I wanna-
- DSDavid Senra
"... go in the opposite order."
- DRDavid Rosenthal
This is one of the things I wanted to talk about.
- BGBen Gilbert
[laughing]
- DRDavid Rosenthal
I, I, I used to, um-
- BGBen Gilbert
'Cause that way, at least by the time you get to one, you, like, w-... you, i- you, it, you're a fan, but if you, if you start at one, you're like, "Oh, these j- guys just suck."
- DSDavid Senra
These guys suck. Yeah [chuckles] .
- BGBen Gilbert
But, like, the, the- it's almost like, um, there's great pleasure in hearing something that you think is excellent and fully baked and, like, uh, e- especially when it's been long-running, you're like, "Oh, this has always been immaculate and perfect."
- DSDavid Senra
Yeah.
- BGBen Gilbert
And then you get to go see some of the early work, and you're like, "Oh, it's so-
- DSDavid Senra
It's like, who are you talking about?
- BGBen Gilbert
... it's so rough," but like-
- DSDavid Senra
You wanna go, you want the early Charlie.
- BGBen Gilbert
I, I get the... I can see where the magic was, even though they didn't know yet. Like, the, the kernel was there.
- 38:00 – 45:30
What motivates, Ben, David, and David to get better?
- DSDavid Senra
like in the books-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... you see the improvement.
- DRDavid Rosenthal
Well, it's fun, too. Like, I like going back and listen to some of your old episodes.
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
'Cause I get to, like, see your journey, you know? Like-
- DSDavid Senra
Yeah
- DRDavid Rosenthal
... it's like I'm proud of you [chuckles] .
- DSDavid Senra
Yeah.
- BGBen Gilbert
Right.
- DRDavid Rosenthal
The, uh, but the, I, I've been thinking about that, and I was thinking about ahead of our conversation here. Like, I used to say all the time, people are like, "Oh, I go back, I listen to the early episodes." I'm like: No, don't. It's so embarrassing. I actually think, like, we always wanna be embarrassed by our last episode. [chuckles] We've just constantly kept, like-
- BGBen Gilbert
Raising the bar
- DRDavid Rosenthal
... every episode, like, we try and just notch it up, and like-
- BGBen Gilbert
'Cause we keep picturing the stadium.
- DRDavid Rosenthal
Right.
- BGBen Gilbert
And we're like-
- DRDavid Rosenthal
That's, that's the like... That's why I think about the stadium, 'cause I think about the, like, the pressure of like, "We gotta do better next time than we did this time."
- BGBen Gilbert
And it's not just filled with, like, you know, Seattle's NFL fans. It's filled with, like, hundreds of thousands of the smartest people that... And this gets to, like, the psyche, like the, the, the, the deep insecurities that at least I have, of like: I want to impress those people. I want those people to think I'm smart, and so I have to produce something unbelievably worthwhile of their time.
- DRDavid Rosenthal
Mm-hmm.
- BGBen Gilbert
And the minute that I don't, I'm, like, literally walking out in front of an F- NFL f- stadium full of people that I want to impress a- and looking like a dumbass.
- DRDavid Rosenthal
It's, it's like a version of the, you know, the, uh, the old, um, you didn't prepare for the test in high school nightmare, or like you-
- BGBen Gilbert
That's exactly-
- DRDavid Rosenthal
Yeah.
- BGBen Gilbert
Yeah, yeah. And, like, I didn't used to have that pressure, but, like, once we found content market fit for Acquired w- with, like, people that I've always thought highly of-
- DRDavid Rosenthal
That's true
- BGBen Gilbert
... that, that, that is the driver now.
- DRDavid Rosenthal
I think we did r- there were a couple of years where we kinda drifted. There wasn't that pressure to keep amping the bar-
- BGBen Gilbert
Yeah
- DRDavid Rosenthal
... and then-
- BGBen Gilbert
You're right
- 45:30 – 52:00
Dead ends: business model changes, paid podcasts, changing the name to “Adapting”, and Senra's “Autotelic”
- DSDavid Senra
uh, point to, like, how we became friends and why, like, I'm putting this out on my feed, and no one, no one... You're gonna be the first non-David Senra voices that ever heard on Founders, and I only would agree to do it, and I only agreed to do it with you guys, is because, like, this goes back to, like, why I want to be surrounded with, first of all, people who have, like, interest, su- super smart people, but also people that have, like, positive sum thinking, right? Patrick O'Shaughnessy has this gigantic, successful show, uh, Invest Like the Best. He's got the Colossus Podcast Network. His fund is called Positive Sum, and that's how he acts. I joined his network, this is, like, months later, um, and they're like: "Hey, like, like, you know, we have editors," whatever. Like, he has, like, this empire over there-
- SPSpeaker
Yeah
- DSDavid Senra
... and resources. He's like: "What do you want?" And I was like: "Uh, I just want you to amplify my audience and then connect me with first- first-rate advertisers," 'cause, like, I think Acquired is a luxury podcast... Not, maybe not luxury. Premium, we gotta go over the distinction there-
- SPSpeaker
Ooh, yeah, yeah
- DSDavid Senra
... for LVMH. But, like, we're not building, like, run-of-the-mill shit. Like, we are- we're saying, "No, no, this is, like... We're trying to set the bar here." But anyways, he's like: "Hey, do you want editors? Do you want any of this stuff?" I was like: "No, I don't want e- no one gets to touch my stuff."
- SPSpeaker
[chuckles]
- DSDavid Senra
Like, people think, "Oh, like, does d- do they tell you what books to read?" And like, no, Patrick liked my show, and he's just like: "Why would I tell you? Like, just whatever you're doing-
- SPSpeaker
Yeah
- DSDavid Senra
... just do it to more people now." Um, and so to answer your question, n- no. Like, I pick the books, I record them, I edit. I'm still a one-person show. I don't know if that'll happen forever, but I do think the fact that it just hap- like, spend so much time with the material, gets it into my brain. But the reason that, uh... Like, I wanna talk about, like, the role you guys played in that, where we were getting on Zoom, and for, like, the background here is, like, you know, we had known of each other. I talked to Ben a long time ago, 'cause he was running this-
- SPSpeaker
Oh, that's right
- DSDavid Senra
... this private podcast. This is, like, years ago. Um, and so anyways, we're like, there, you're-
- SPSpeaker
It's also funny to think back, like, all the dead ends that we went... Like, we went down a ton of them. You went down a ton of them.
- DSDavid Senra
Millions.
- SPSpeaker
We're about to talk about some of them. Like, there's so many dead ends.
- DSDavid Senra
But they're in the books, too.
- SPSpeaker
Yeah, but they're in the book.
- DSDavid Senra
Like, that's-
- SPSpeaker
That's exactly, yeah, we just-
- DSDavid Senra
Remember when we changed the name of the show to Adapting?
- SPSpeaker
Oh, my God, that was, that was a dead end. [laughing]
- SPSpeaker
Whoa. [laughing]
- SPSpeaker
That was, that was on me.
- DSDavid Senra
I didn't know this.
- SPSpeaker
That one was on me. [chuckles]
- DSDavid Senra
Tell the story.
- SPSpeaker
Well, C- COVID happened, and we were like, "No one wants to hear these, like-
- SPSpeaker
Oh, man
- SPSpeaker
... stories of, like, extreme capitalism." Like, we- we're like the X Games of capitalism.
- SPSpeaker
[laughing]
- SPSpeaker
And, and like, this is a, a moment where, like-
- 52:00 – 56:30
“You’re not advertising to a standing army, you’re advertising to a moving parade”
- DSDavid Senra
made me think of something. Let me interrupt this story, 'cause I think it's really important. You're like, "Oh, is anybody going to listen to our... Like, no one's gonna listen to our Amazon episode. They already know it." And so this is something that, like-
- DRDavid Rosenthal
Oh, it's-
- DSDavid Senra
And then it becomes, becomes the most successful-
- BGBen Gilbert
Are you gonna quote Ogilvy?
- DSDavid Senra
Yes.
- BGBen Gilbert
Yes.
- DSDavid Senra
Yeah, 100%.
- BGBen Gilbert
I've listened to enough founders to know.
- DSDavid Senra
Yeah, because it's like, this is so key that people don't understand. It's like you're not advertising to a standing army, you're advertising to a moving parade. And so, like, I will literally get on calls with, like, media company founders that are, like, selling ads or, like, building companies, and I'm like, "Oh yeah, you must have read Ogilvy." They're like, "What?" And I was like, "These are not new lessons." Like, if, if... And again, this comes from the humility to realize, hey, Warren Buffett's smarter than me. So if that dude in his shareholder letters is saying, "Uh, David Ogilvy is a genius," I'm like, "Wait a minute, this dude, how many businesses has Warren Buffett looked at, at that point? How many founders and managers has he looked to, and he's like, 'This dude's a genius?'"
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
This is not rocket science, guys.
- BGBen Gilbert
Right.
- DSDavid Senra
Just go and like- [laughing] Let's search David Ogilvy on Amazon. Five books? Good. Order them all.
- DRDavid Rosenthal
These days, search David Ogilvy and your podcast player of choice.
- DSDavid Senra
Yeah!
- DRDavid Rosenthal
Like...
- DSDavid Senra
Um, that's- the, I, I went to-
- BGBen Gilbert
Wait, but e- explain the, the standing army versus-
- DSDavid Senra
So you're not advertising to a, uh, standing army, you're advertising to a moving parade. But what happens is, like, even when you put on, uh, the Sequoia episode, right? We went, me and David went on a hike in Stanford, and I was like: "Dude, you have this crazy back catalog. Every single day, you have more people following your podcast feed than you had the day before." I was like- and I, 'cause I knew this, because I was a su- a subscription podcast, right?
- DRDavid Rosenthal
Recount briefly your business model journey.
- DSDavid Senra
So I, I'll give you the shorter breakdown, because, like, I went through so many of them. I just put a hard paywall, "Listen to the first 30 minutes. You wanna listen to all of them, um, then you pay," right? And it convert- the-
- DRDavid Rosenthal
And this is when we had that chat-
- DSDavid Senra
Yes
- DRDavid Rosenthal
... that you were talking about.
- DSDavid Senra
We gotta go back to that.
- DRDavid Rosenthal
We were like, we were like, "Dude-
- DSDavid Senra
"You're doing it wrong."
- DRDavid Rosenthal
... do not- you, you're doing it wrong." [chuckles]
- DSDavid Senra
Yeah, 'cause the- we- there's been times like this one, where we're like, "What the hell are you doing?" But there's been other times t- where you come to us and you're like, "Do you know how good your Sequoia episodes were? And, like, the fact that you have four times the audience that you have now-
- DRDavid Rosenthal
Right
- 56:30 – 1:00:40
Comparison of podcasting business models
- DSDavid Senra
[chuckles] he, he says in the book, he's like, "His estate outside of Chicago was so big, he had 40 full-time employees." I'm like, "What?" [chuckles] Like, "What are you talking about?" Like, th- make these words make sense in my mind. That doesn't make any sense to me. So you read Albert Lasker, and then he tells you about Claude Hopkins, and he's like, "Yeah, the, the information was so good that, like, I stored that in my vault for 20 years." And then once he sold his, uh, advertising, uh... Or I think he gave it away, like a token, like $100,000, you know, to the people working, uh, there.
- BGBen Gilbert
Mm.
- DSDavid Senra
And then they released it, and Claude went off on his own and, and everything else. So these are not, like-
- DRDavid Rosenthal
Yeah. Okay, so you were doing the 30-minute hard cutoff when we- [chuckles]
- DSDavid Senra
And so when-
- DRDavid Rosenthal
We had that famous-
- BGBen Gilbert
It is so unsatisfying. It's like, I'm gonna listen to 30 minutes of this episode, and then, like, I j- have to get... Someone's asking me to pay for the rest.
- DRDavid Rosenthal
But you might have a pretty good conversion rate, right?
- DSDavid Senra
The conversion rates were higher, but-
- DRDavid Rosenthal
Of course
- DSDavid Senra
... you guys said th- th- this is where, like-
- DRDavid Rosenthal
You were at a local maximum.
- DSDavid Senra
This is where, like, you were very helpful. Like, David, first of all... And you guys are nice, but this is not the language you use. You're like, "You fucking idiot." Like, [laughing]
- BGBen Gilbert
[laughing]
- DRDavid Rosenthal
[laughing]
- DSDavid Senra
That's, that's like... And but you guys are so nice, so it's like, "Dude, you're doing it wrong." Listen, for every one person, I think it was Ben that said this, like, for every one person that would buy a podcast, there's 1,000 or 100 that would listen to them for free. Like, just-
- BGBen Gilbert
It's about 100.
- DSDavid Senra
Yeah, uh, probably even more than that, you know? And so then you guys would show me, like, you open the kimono. You're like, "This is... These are our downloads. This is who we advertise with. This is what we charge for advertising." You're just like-
- BGBen Gilbert
Well, the other, the other really key insight is, uh, so after spending a bunch of time with originally Kimberlite, then Glow-
- DSDavid Senra
Yeah
- BGBen Gilbert
... which sold to Libsyn, and still what powers the Acquired LP program, uh, an interesting learning is most podcasts should generate about 50% of their revenue from direct monetization, some kind of membership program or paywalling their feed, um, and about half from advertising. And, and it should- the math should sort of work out where that's gonna be the case. For the type of podcast that we are, where you have lots of founders and CEOs and hedge fund managers and th- these sorts of people listening, y- y- you could never ask someone to pay you in membership what they are worth to the most valuable advertiser for that slot. And so the way it sort of works out is, like, you're massively hamstringing your monetization potential if you make it membership only, 'cause you'd have to be like, "Uh, yes, please pay 2 to $5,000 a year in order to get access to this private thing," versus if you were to take that same piece of content and open it up to advertisers.
- DSDavid Senra
You made the great, the good point earlier, and we can elaborate on that, right? Why you're so psychotic about, "This sentence is- needs to get out of here. Like, these two sentences, let's, let's remove it," because if you could factor in the average hourly rate of the people in your audience, it is unbelievable. So even I think if you make, what, a million dollars a year, and we know people obviously in our audiences make a lot more than that, but I think a million dollars a year is what, 500 bucks an hour or something like that? I don't know the math.
- BGBen Gilbert
Sounds right.
- DSDavid Senra
I'm not a good math person. But, like, so you're asking if they listen to an hour-long podcast of Founders, it's like, that's $500. Like, you cannot waste these people's time.
- BGBen Gilbert
Yeah.
- DSDavid Senra
So I never answered your question when you're like, "Hey, how do you guys think about this? Do you, do you re-edit, or do you cut them out?" I use Descript as well. I actually think the way I listen to Founders is obviously listening to it, and listening and reading.
- BGBen Gilbert
Yeah.
- DSDavid Senra
Like, the superpower of podcasts is you can listen to it when you're doing something else. But-
- DRDavid Rosenthal
But when you're editing, though, the-
- DSDavid Senra
But I think I'm gonna put all my ad- all my podcasts up on YouTube, not... I don't have any video, but I think I'm gonna use Descript. So, like, if you... There is like-
- 1:00:40 – 1:05:00
Senra’s insane Readwise "healthy twitter" habit
- DSDavid Senra
yes, I'm very aware that, uh, who's listening, I'm not ever gonna waste a lot of their time. And what I've found with the more practice I have for the podcast is I'm able to edit on the fly. Like, I don't have a script, right? So, like, I'll go through the book. I highlight, then write down whatever pops in my mind. I don't th- like, just, am I... First of all, the highlights, like, am I excited about that? "Oh, that's interesting," highlight.
- BGBen Gilbert
Yeah.
- DSDavid Senra
Just go off instinct, right?
- BGBen Gilbert
Yeah.
- DSDavid Senra
And then write down, uh, like, something that, "Oh, that's like this," or, "That made me think of this," and I just write it down, right? Then I'll reread all these highlights the night before I record, uh, so it's like the second time.
- DRDavid Rosenthal
You're do- you're doing this in physical books, right?
- DSDavid Senra
Physical books, yeah.
- DRDavid Rosenthal
But you're putting your notes into Readwise?
- DSDavid Senra
That happens after.
- DRDavid Rosenthal
Okay.
- DSDavid Senra
That happens after. So the fifth time, every single book I do, I think I read the highlights five times, and the fifth time is me actually taking pictures of the physical book and putting it in Readwise. So Jeff Be- I was thinking about this yesterday, 'cause, um, I'm also sl- slightly obsessed with Jeff Bezos.
- DRDavid Rosenthal
... You're slightly obsessed with a l- a lot of founders. [laughs]
- DSDavid Senra
That's why when we're like-
- DRDavid Rosenthal
[laughs]
- DSDavid Senra
You're like, "We're sitting in chairs." I was like, "Dude, I'm gonna be Ford." [laughs]
- SPSpeaker
[laughs]
- DRDavid Rosenthal
Yeah, we were setting up the camera angles before. [laughs]
- DSDavid Senra
'Cause you know what I love? Like, um-
- DRDavid Rosenthal
We're like, "I... We've gotta move David's chair back here a little bit." [laughs]
- DSDavid Senra
[laughs] Do you ever... Have you ever watched the old Jeff Bezos interviews when he's, like, first starting Amazon?
- DRDavid Rosenthal
Oh, oh yeah.
- DSDavid Senra
He's, like, skinny and bald, like, bald and-
- SPSpeaker
It's the one that's, like, in that field outside the conference?
- DSDavid Senra
Yes, I think this is the one. He's, like, sitting... Like, you see grass behind him.
- SPSpeaker
Yes.
- DSDavid Senra
I don't know if he's in a field. So the... But he, like, leans forward, and he's like, "We're gonna be the most customer-obsessed company ever." [laughs] It's like-
- DRDavid Rosenthal
And he's got that look on his face.
- DSDavid Senra
Yeah.
- SPSpeaker
Yeah.
- DSDavid Senra
That's how I am about founders.
- 1:05:00 – 1:15:00
Is it possible for the ultra-wealthy not to mess up their kids?
- DSDavid Senra
know. But I read this book, uh, it's episode 212 of Founders. It's called Michael Jordan: The Life. It's a 600-page biography, and in that book-
- DRDavid Rosenthal
You just have, like, this encyclopedia knowledge, too, of the numbers of your episodes, which I'm so impressed by.
- DSDavid Senra
I don't. It's only because I reference that all the time, so when- if you look up something over and over again-
- SPSpeaker
Yeah.
- DRDavid Rosenthal
Yeah, yeah.
- DSDavid Senra
It's repetition. Everything in life is repetition. Sam Walton's career is repetition. You know, like, it's like, I just think you're trying to... This is what I asked Charlie. Like, he- one of the most interesting things he said, he's like, "One of the best things that ever happened to me is I got rich later in life."
- SPSpeaker
Mm.
- DSDavid Senra
You know, like, he saw the time-
- DRDavid Rosenthal
What do you mean by that?
- DSDavid Senra
... and how difficult it was. Like, he was talking about, like, um, imagine you being, like, a b- super famous or rich when you're, like, 21 or 25, and how disorienting. He's like, "I was a full-grown man-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... like, with a life experience, with a wife and kids and-
- DRDavid Rosenthal
He had a child who died.
- DSDavid Senra
Yeah, I did not-
- DRDavid Rosenthal
Before he got rich
- DSDavid Senra
... I did not mention that, yeah.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
Um, but, like, he had all, like, a, you know, a full life of experience, and therefore, also, the, the, a main problem that happens is people don't know. They're like, "I was the son of a poor man. Now I'm rich, and my kids live an unbelievable amount of wealth and privilege. How do I deal with that?" That comes up in the books for hundreds of years. The answer is no one fucking knows, right? [laughs]
- SPSpeaker
[laughs]
- DSDavid Senra
And so with Charlie, though, the benefit is he didn't have a famous last name or a lot of wealth. His kids were, like, grown.
- DRDavid Rosenthal
Right.
- DSDavid Senra
They wouldn't have to deal with that when you're-
- SPSpeaker
Yeah
- DSDavid Senra
... five or seven or 10. He also gave me some advice that was fascinating.
- DRDavid Rosenthal
You do, like... You gotta pay that bill eventually, though. Like, his grandkids have to-
- DSDavid Senra
Well, so how do you deal with this, though, right?
- DRDavid Rosenthal
Right.
- DSDavid Senra
Like, he's multi-billionaire. Like, that's an insane-
- SPSpeaker
Right.
- DSDavid Senra
I just-
- 1:15:00 – 1:17:30
The fleeting moments you get to spend with your kids
- DSDavid Senra
they're like Warren Buffett's kids, where, like, they, they run foundations, and they wanna give the money away. And I don't think they're coke addicts. I don't know, but, like, you don't- it's just dependent on the person. So I- if there was a simple... If there was a correct answer, I think some of these guys, some of these guys-
- BGBen Gilbert
Would've figured it out
- DSDavid Senra
... would've figured it out.
- DRDavid Rosenthal
Well, that's the thing about humans, right? Like, every person is different.
- DSDavid Senra
Yeah. Yeah, so it's- I have no idea. Um, it- uh, really, and that's the biggest thing, where I think, um, this is one of the lessons I learned from the podcast where, you know, you mentioned this at the beginning, Ben, where most of these people are just so- they're, like, best in class in this one dimension in the world, and of course, to get that, they had to, to be poor. They had to- they couldn't optimize all other areas of their life at the, at what they did for, like, their work, right?
- DRDavid Rosenthal
Mm-hmm.
- DSDavid Senra
You know?
- BGBen Gilbert
Mm-hmm.
- DSDavid Senra
Sam Walton is one of the rare guys where he gets to the end, he knows he's dying, 'cause he's got cancer all over his body when he's writing that book.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
And he's like: "Listen, if I could do everything again," he's like, "Yeah, I missed some of my kids' childhood." They worked in the stores, and he took them with him, but he's like, "I'd do it again!" He's like [chuckles] , "I had to do this. I had to get after it. I had to improve." A lot of them, you know, get to the end of their life and like, "Oh, I, I regret..." The founder of IKEA has the best words on this. He said, um, you know, "I had three sons growing up." He started IKEA when he was, like, 17, worked on it till he was, like, 80-something, and he's like, "I sacrificed my three sons' childhoods. I regret it." He goes, " Anybody that has kids knows that childhood does not allow itself to be reconquered." Um, and so, like, we were hanging out today. We were gonna do a recording, go to dinner, and I was- my plan was I was- I wanna see my son. And he's like, "And my daughter." It's like, I'm gonna take the red-eye. And then I realized, it's like, yeah, but I wanna spend time with Dave and Ben, so I'm leaving early tomorrow morning. But it's like, I'm doing this as fast as possible, and if I had to, I'd, like, fly back and forth because, like, your kids are... Think about, like, you- the relationship-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... you guys have with your parents. Are, are they still alive?
- BGBen Gilbert
Yep.
- DRDavid Rosenthal
Yep.
- DSDavid Senra
Okay, so you get to talk to them, see them, but you have your whole life, right?
- DRDavid Rosenthal
Right.
- DSDavid Senra
When your kids are small, there's, like, this tiny window when they're, like, two to five to six, where you're everything to them.
- DRDavid Rosenthal
Oh, yeah.
- BGBen Gilbert
Mm.
- DSDavid Senra
Even my-
- DRDavid Rosenthal
You, you and I have talked about it.
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
I absolutely feel this way.
- DSDavid Senra
Even my 10-year-old-
- DRDavid Rosenthal
We were-
- DSDavid Senra
... daughter, like, right now, she wants to spend time with me. Like, it was the cutest thing ever. Um, I was leaving, going to LA to see Charlie and then coming up to San Francisco to see you guys, and she texts me. She goes, uh, "I'm wearing your sweater, 'cause, like, it makes me feel close to you-
- BGBen Gilbert
Aw!
- DSDavid Senra
... like, while you're gone." You know what I mean? But if you ask her, "Do you wanna spend movie night with Dad and Mom, or do you wanna go play Roblox with your friends?" Every-
- DRDavid Rosenthal
For sure the latter.
- 1:17:30 – 1:20:00
The value of building relationships with best-in-class peers
- DSDavid Senra
every day I miss, my son's about to turn three, it's like, I'm not gonna get back that day-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... and there's only, like, a thousand of those days.
- BGBen Gilbert
Mm.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
And my wife won't have any more kids, even though I was like, "I want a bunch of kid..." [laughing] Like, once I-
- BGBen Gilbert
[laughing] Like, exactly.
- DSDavid Senra
Because I want a bunch! And she's like: "No way." I say, "Hey, you're the... I don't have to get pregnant, so that's fine."
- DRDavid Rosenthal
Something that Buffett and Munger did with the Graham Group that, like, was way ahead of its time, that now anybody can do, is they formed their social networks outside of geographic barriers.
- DSDavid Senra
Yeah.
- DRDavid Rosenthal
And they found their, like, most compatible, most like-minded, highest level of talent, you know, peers.
- DSDavid Senra
Mm-hmm.
- DRDavid Rosenthal
And then they just, like, got on planes and got to go see them. You know, and, like, that was really hard to do back in the day, and now anybody can do it. It's kinda like the Bill Gurley, you know, "You have no excuse not to do that."
- DSDavid Senra
You also... But here's the thing, what people get wrong is, they're like: "Oh, I wanna meet this guy." You have to do the work necessary to make them worth your time, right? Which is, like, the unfair advantage that the three people sitting in this room have-
- BGBen Gilbert
Mm-hmm
- DSDavid Senra
... is that it doesn't matter. That's why, like, in the last six weeks, I've gone to lunch or dinner with multiple billionaires. This is like... And the people that, like, you get to talk to and all this other stuff, it's just like, this dude is crazy. He's read 300 biographies of entrepreneurs. There's no way I'm gonna have dinner with him and not pick up one idea.
- DRDavid Rosenthal
Yep.
- DSDavid Senra
Like, and then now I've built this machine where, like, "Oh, that's an interesting idea. I'll just plug it into this business." And, like, it's not a financial transaction by any means, but there's no- I- the reason- it's not that like... Charlie was the first person I met that I was actually nervous about, and it's... The reason I'm not nervous is 'cause I know I've done the work.
- DRDavid Rosenthal
Yeah.
- BGBen Gilbert
Yeah.
- DSDavid Senra
Like, you can't put me in a room with anybody on the fucking planet, and I'm not gonna be able to tell them at least one interesting thing.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
It doesn't mean I'll be the most, the best dinner they've ever had in their life. That's not what I'm saying. It's just like, they're gonna hear something that's like, "Oh, that's interesting," and that goes to their own brain, and it's only because I've spent six years, and, and same with you guys. It's like, oh, you should feel comfortable. Like you guys mentioned earlier, it's like, um, the, the- your audience feels like s- you know, two football fields, and like, oh, it's a little bit of like, uh, not... You didn't use the word insecurity, but like, you know, a little, like, nervousness. I want these people to, like, like me.
- BGBen Gilbert
Yeah.
- DSDavid Senra
It's just like-
- BGBen Gilbert
Oh, yeah.
- DRDavid Rosenthal
Yeah, it's like, it's like-
- DSDavid Senra
You... You under-
- DRDavid Rosenthal
There's a fear pushing you from behind.
- DSDavid Senra
But you know, like, you've most likely read... You, you're, you're- you've know more about the subject than they do.
- 1:20:00 – 1:29:15
How the book publishing industry works
- DSDavid Senra
I guess is my point.
- BGBen Gilbert
We- yeah, I think we now have a process that-... uh, means that when you and I put in the work, the pro- the product is good, but it took a long time to, to arrive at that. It's almost like, um, uh, you know, the, uh, this is another Sam Hinkie thing: trust the process.
- DSDavid Senra
Yep. The um-
- SPSpeaker
Oh, that was chapter.
- DSDavid Senra
I guess the, the, the point I was making there, though, is, um, like, because you guys do such, so much preparation, and, like, it's now y- your life's work, y- like, it's just so much... It's, it's gonna be so hard not to add value to the people in your lives, whether it's, like, friends that never show up on a podcast or friends that, like, you don't have a business relationship with.
- BGBen Gilbert
Mm-hmm.
- DSDavid Senra
'Cause it's like, and, like, you're just gonna add value because what you do is so rare. Like, I, uh, Naval Ravikant has this, uh... He's influenced my thinking a lot, too, and he has this thing in, um, in the Naval, The Almanack of Naval by our friend Eric Jorgensen.
- BGBen Gilbert
Yep.
- DSDavid Senra
And he's just like, "If you read an hour a day, that puts you in the .0001% of humans."
- BGBen Gilbert
Right.
- DSDavid Senra
And I'm like, "That can't be true!"
- BGBen Gilbert
Oh, yeah. No, that, that's the dirty secret of Acquired and founders, is that people don't read books. So if you just read them and then tell people what's in the books, you're gonna 100x the market for books. [chuckles]
- DSDavid Senra
And I couldn't believe that. I was having dinner with the same friend, uh, that was telling me, like I told him, I was like, "Oh, I'll try to build a business around, like, uh, my reading." This is, like, a couple months ago. And he's like, "You vastly overestimate how much people read." He goes, "How much do you... How many books a year do you think the average person reads?" I was like, "I don't know, 12?"
- BGBen Gilbert
It's one.
- SPSpeaker
It's, like, .5.
- BGBen Gilbert
It's zero!
- DSDavid Senra
I don't know.
- BGBen Gilbert
I remember asking-
- SPSpeaker
Yeah
- BGBen Gilbert
... a book publisher. He go- and he said, "America reads a book a year."
- DSDavid Senra
They, well, he, well, he quoted some other study. I, I said, "12." He's like, [laughs]
- SPSpeaker
[laughs] No!
- DSDavid Senra
"No, not 12." He's like, "It's zero." The average is zero.
- SPSpeaker
Yeah.
- BGBen Gilbert
Huh?
- DSDavid Senra
It's crazy. And yeah, to your point, um, I've become friends with a bunch of, uh, writers. Some of them I met through the podcast, and they've been telling me, like, teaching me about the publishing industry and just breaking down, like, 98% of books ever published sell less than 5,000 copies.
- SPSpeaker
Yeah.
- DSDavid Senra
It's the power law, everything.
- BGBen Gilbert
The, the book-
- SPSpeaker
It's yeah.
- 1:29:15 – 1:39:00
How to differentiate yourself as an investor in 2023?
- DRDavid Rosenthal
inventory.
- DSDavid Senra
And so he goes, "Uh, hey, uh, Colossus Network, I'd like to buy up, uh, every single ad inventory- [chuckles] ... for 2023 on every single one of your shows." That's how you know that that likelihood, that guy's gonna win.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
Like, I don't know the details of his business. It's private and everything else. It's like, that's the right decision-
- DRDavid Rosenthal
Yeah
- DSDavid Senra
... the same decision.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
That's what Ogilvy would've done. That's what Buffett and Munger do when they put money in. Like, that is... That's what Coca-Cola does. It doesn't matter the economic climate. It's, you're ever gonna see less Apple f- uh, uh, billboards.
- DRDavid Rosenthal
Yes or no.
- DSDavid Senra
You're gonna see less Coca-Cola? No.
- DRDavid Rosenthal
It's interesting to, like, think about this in the, um, venture business, right? Like, uh, which obviously, as we record this here in mid-March, you know, 2023, [chuckles] there's a lot going on in the venture business.
- BGBen Gilbert
It's, it's so dynamic right now-
- DRDavid Rosenthal
Right
- BGBen Gilbert
... that I feel like we don't know the last two iterations of what have happened because we've been recording, and I haven't checked my phone.
- DRDavid Rosenthal
Yeah, [chuckles] right.
- BGBen Gilbert
Like, that's how fast the world is moving right now.
- DRDavid Rosenthal
Right. Things are happening very quickly as we speak. Uh, but I think a consequence of that, to your point about, like, you should advertise heavier during recessions, I think differenti- customer differentiation among venture firms is just declining rapidly, right? Like, like, what is-
- BGBen Gilbert
Well, no. It was until, uh, interest rates went up, but now that-
- DRDavid Rosenthal
No, but even, like, I, I think-
- BGBen Gilbert
Capital is scarce again
- DRDavid Rosenthal
... I think, I think both the up and the down cycle is, both, I think, are commoditizing.
- BGBen Gilbert
I totally disagree with this. I think when c- when commod- when capital was a commodity and money was free, it was extremely hard to differentiate yourself as a venture firm or any financial firm. But, like, it, it should be easier than ever to differentiate yourself because the thing-
- DRDavid Rosenthal
Okay, but how do you... Okay, so how do you differentiate yourself right now?
- BGBen Gilbert
Uh-
- DSDavid Senra
You, you guys are doing it.
- BGBen Gilbert
You, you can... I mean, well, one of them... Like, let's, let's abstract away, like, speaking to the Acquired audience as, as one of them, uh, or as a gigantic means of differentiation.
- DRDavid Rosenthal
Well, let's just say your XYZ average venture firm out there.
- BGBen Gilbert
Uh, having money and writing the checks.
- DRDavid Rosenthal
Right, but, but yes, having money, right? But, like-
- BGBen Gilbert
I- a year from now, it's like six to 12 months from now, that's gonna be differentiating.
- 1:39:00 – 2:02:30
The greatest historical examples as content marketing
- DSDavid Senra
not an investor, so I don't know anything about your, your world, but it's just, like, I'd spend my time reading and learning about business history. Charlie Munger and Warren Buffett did that. Every single investor you guys have probably read about does that all the time. They read constantly, right?
- DRDavid Rosenthal
Yep.
- DSDavid Senra
Uh, I would share what I know. That's gonna build my network of other people. Those people are eventually gonna send me deals. Then I have this huge advantage that you couldn't even do 10 years ago c- or 15 years ago, 'cause there's no such thing as a podcast, right? It's like, now I can record all the stuff I'm learning, right?
- BGBen Gilbert
Which we should say, like, there have been iterations of this. Like, this is how, uh, Union Square Ventures became Union Square Ventures, or Foundry Group became Foundry Group, 'cause-
- DSDavid Senra
Blogging.
- BGBen Gilbert
Yep, blogging, and then Brad and Jason writing the book on h- venture deals. I mean, it's like Angel, this-
- DSDavid Senra
The, uh, Venture Hacks with Naval and Rivi.
- DRDavid Rosenthal
Yep.
- BGBen Gilbert
Totally.
- DSDavid Senra
I- I have two other examples. This is like, it's not even venture. Like, what is the most successful content marketing of all time?
- BGBen Gilbert
Ooh. Uh, Michelin?
- DSDavid Senra
No, Berkshire Hathaway [laughing]
- DRDavid Rosenthal
[laughing] Oh, totally, of course.
- DSDavid Senra
Berkshire Hathaway letters.
- DRDavid Rosenthal
Of course. Yep, of course. [laughing]
- DSDavid Senra
Because this is how you know he's a genius.
- DRDavid Rosenthal
Of course.
- DSDavid Senra
It is the greatest act of salesmanship, 'cause you never even see the sale happening.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
It's like, "Hey," and they spend... You know, you guys have probably done this research, how much time they spend on those letters.
- DRDavid Rosenthal
Yeah.
- DSDavid Senra
It's, like, half a year, seven, eight months for every letter.
- DRDavid Rosenthal
Right.
- DSDavid Senra
This is not like, "Oh, I just jotted some shit down of what I learned this year." [laughing]
- BGBen Gilbert
[laughing]
- DSDavid Senra
And the crazy thing is, like, he's, he's-
- DRDavid Rosenthal
Old Uncle Warren. [laughing]
- DSDavid Senra
How many people have... This is something Charlie tal- oh, so this is a great, great thing that, that, uh, this came up here. So-
- DRDavid Rosenthal
Did you talk about the letters with him?
- DSDavid Senra
No, I asked him about, like... So I was explaining to him, I was like, "Charlie, I'm literally in the middle of, like, reading about you when you were, like, around my age." So every time I read a book, I'm like, "Okay, I" ... First of all, I know what year they're, they're born, so every time as I go through the books, I'm like, "How old are they?" And I write down, "Okay, he's 24 here, he's 30..." I wanna know what they were doing in and around my age. And so I'm like: Charlie, I'm thinking about you guys. Like, you've just started, like, your fund starts when he's, like, 41 or something like that. I don't remember what it was, right? And um, and I was like, "Then, like, 50... " Like, you start out, you're trying to figure things out. You could see them kind of figuring out, making the mistakes. You guys did an excellent job on your episode, like, talking about what they learned from. Getting to, like, get away from the Ben Graham, like, get to wonder- excellence.
Episode duration: 3:20:07
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