David Senra + Mitchell Baldridge #6 : Writing the Founders’ Book, Building Natural-fit Businesses, and Craft

Smart Friends Episode 89: David Senra and Mitchell Baldridge #6

Today, we’re back with David Senra and Mitchell Baldridge for a wide-ranging conversation on effort, authorship, entrepreneurship, and the compounding effects of long-term projects.

If you don’t know them yet, David Senra is a biography-reading maniac and the mastermind behind the ever-growing Founders Podcast, the best place to learn from history’s greatest entrepreneurs.

Mitchell is the founder of the Baldridge Financial empire, which offers tax and accounting services, betterbookkeeping.com, cost segregation, and much more.

Today, we talk about the story of a listener named Wouter, who earned the right to work on the official Founders’ book. Woulter is the definition of hustle and created opportunity for himself.

We explore how AI evolved into personalized tools for creative workflows, research, and creative leverage. We also discussed the economics of self-publishing, systems building, and starting a business that’s completely natural to you.

Links to Platforms:

We discuss:

How extreme effort and agency created the opportunity to publish the Founders' book.
The economics, longevity, and cultural value of self-published books.
Bootstrapping and scaling a HoldCo with multiple service businesses.
Practical uses of AI for research, productivity, and creative leverage.
The importance of doing the work for its own sake and loving the process.

A rich episode for anyone building something long-term and looking to surround themselves with high-agency thinkers.

Quotes from David:

“You don’t handle the stress—you like it. Or else you wouldn’t be doing this.”
“If you want the ups, you have to endure the downs. That’s just a fact.”
“This is the best version of my life, whether it’s 300 people at a club or 3,000 in a theater.”
“Most people try to keep things even—no extreme highs or lows. But all the exciting shit is in the variance.”
“If you have something else you’d rather be doing, then you should go do that.”
“Books are so valuable because of how long they take to consume.”
“Effort is universal. Doesn’t matter if it’s a garden or a podcast—people respect work.”
“AI is going to wipe out the middle. If you’re average, you’re gone.”
“Sage remembers things I don’t—and that’s priceless.”
“Don’t rush it. Make something great. A good book can sell for 50 years.”

Quotes from Mitchell:

“I get frustrated at how long this takes—but I want to build something meaningful.”
“Turn everything into a car wash. Put the customer into neutral and pull them through.”
“The tax code is getting more complex, but the systems are getting better.”
“AI is going to destroy everything below the 95th percentile.”
“I’m bootstrapping a holdco—and it takes time.”
“Send me a customer, I’ll give you $1,000. Send me 1,000 and I’ll mortgage my house for you.”
“I don’t want 25 meetings a month—I want results.”

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Learn more about David Senra:

Learn more about Mitchell Baldridge:

Additional episodes if you enjoyed:

Episode Transcript:

Eric Jorgenson: All right, we're riding. We're back. We love each other. We miss each other. We're smart friends once again. I feel like we've had both a very exciting and a pretty normal last, whatever, six months. Everybody's just doing their thing, which is amazing. But you guys, David just had an event in New York. There was a whole exciting kerfuffle, and there's all kinds of new maxims and stories to share with each other and with you.

David Senra: What’s the kerfuffle?

Eric Jorgenson: The book, the Founders book.

David Senra: You want to start with that?

Eric Jorgenson: It's on the top of both of your lists, so let's do it.

David Senra: Okay. I actually think this is actually really interesting. Sometimes, I think people misinterpret, like they want to get your attention, so they just like send you messages every day or like email you over and over again, but it's like not of value. Do you remember, I think you guys were at that event I did where a friend of mine who was mentored by Sam Zell for like 25 years gave a talk on like how to build relationships with like very high value people, and this whole talk was just like these people, all day long, somebody wants something from them. In Sam's case, they want to be a partner, they want money, they want to sell him a company. And it's just like all day, gimme, gimme, gimme. And so, his whole point was just like, I just found- I essentially just sourced deals for Sam that I thought were valuable. I did a bunch of research for free, and then I presented him what I thought were the best ones. One of the first ones I presented him, he winded up doing and making a bunch of money on. It's like, oh, this guy's good. I should probably keep him around. And then immediately after, he got a bunch of emails from people that were in the audience. They're like, hey, I'd love to like pick your brain. It’s like no, did you not just hear what he said in the talk? That's not very helpful. So, I've been inherently resistant, I am not an author. So like, I have publishing, like big publishing houses email me all the time about writing a book and like people telling me I should write a book and everything else. And I told Eric, me and Eric have talked about this over and over again. I cannot be the bottleneck for any kind of book because like I'm only going to podcast. There's nothing else. I'm never going to sit down and be like, hey, I'm going to take a few weeks or a few months or a few hours a week out of podcasting so I can write a book. There's this guy, and I can't pronounce his name... Waulter. Yeah. I called him Waulter, I think in front of everybody in the audience. And I saw, he was sending me a bunch of messages and stuff but he did something like really, really smart because he wanted to launch a podcast, and most podcasters, as you know, it's like most people take it very casual how they approach it, but definitely like there's very few podcasters that actually have like a world classclass like work ethic. And I saw a couple things. I was actually talking to John and Jordy about this, the TPBN guys because they are working their asses off.

Mitchell Baldridge: Wait, so this is the same guy who flew to Victoria and interviewed Andrew Wilkinson?

David Senra: So I kept seeing him in my mentions, and then I saw other people that I know like Andrew who's a friend and Eric Glenn, the founder of Ramp, who's a friend, and so this is one thing that me and John and Jory talk about all the time, it's just like, I think one of their differentiating aspects is like they're actually working really hard at what they're doing. They're taking it excessively serious. And so, I sent them, I was like, hey, I don’t know this guy. I don’t know if his podcast is good. But like mad respect for how much effort he's putting into it. So, I saw this tweet from Andrew Wilkinson. It's like this guy from the Netherlands emailed me asking if I'd come on his podcast. I didn't want to, so I used my usual line. I only do it in person in Victoria. Welp, the son of a bitch called my bluff, flew 12 hours, mic in hand. Well played, Waulter. It turned out great. And then I saw a tweet from my friend Eric Glyman, CEO and co-founder of Ramp. And he's like, to prep, he's like, give Waulter, he has a shot, give him a year, he has a shot to go build like a really good interview podcast on modern company builders. To prep, he wrote a 40-page book on Ramp and flew 3000 miles to film. And then I was doing this, me and Patrick were doing this live talk at Ramp’s headquarters in New York. And I see another tweet from Waulter, and he's like, I set out to create the Founders podcast book, but I failed. I spent 27 days listening to over 380 episodes. I spent $5,000 on design fees and over 450 just on ink costs, the result, a book with 366 daily quotes. He gave it to me when I met him actually. I think there's only two in the world... lessons and maxims from history's greatest founders. So, the reason I bring this up is... Go ahead.

Mitchell Baldridge: I hadn't even put together that this was the same guy who was working these nine angles, but this is so interesting because he's doing everything in a quality way. You keep talking.

David Senra: If he had just been sending me a bunch of DMs, like I like your podcast and I'd like to meet, I'm launching a podcast, like they're just going to get- just going to go nowhere. But the effort is universal, it doesn't matter if you're growing a garden like our mutual friend Kevin, or you're building a giant company, or you're doing a podcast, it's like effort is universally appreciated. And so, what happened is after the event, we spent time with him. Like he got- me and Patrick gave him, to the degree that he needed our advice, advice on like certain areas of podcasting that there seems to be open space in, because hey, interviewing fucking entrepreneurs seems to be well taken care of. I introduced him to both me, Eric and Kareem, the two founders of Ramp, talked to him. So it's like, just from doing this, and he also flew from the Netherlands to New York to be there and everything else. And so, what I was talking to was like, listen, man, if you want to do the Founders book, I'm really good friends with Eric Jorgenson. This isn't the Founders book. Like that's not what we have in mind. It's really cool. It's interesting. But what I'm interested in doing, because it changed my life, is like the Almanac of Naval, that version of Founders. And so I go, here's the deal I'll make you. I will give you this opportunity. If you do the research and you work your ass off on this, we will then go to Eric, who's a good friend. He will publish it. He'll smooth out the writing. I will promote it. And then you can keep all the fucking money. I don't need to make money off of a book. I just, I want something that's interesting that I can refer to that I'd be proud of other people to read, and then since you're a young kid, like this might jumpstart you. And so that's like the big change from the last time we recorded.

Eric Jorgenson: And I've been spending like, well, David and I've been talking about this for... a Founders book must exist. And we've been talking about it for years on and off, throwing around a bunch of different concepts. But like this is catalyzed by like the amount of effort that he put forward basically. You're like, all right, there's huge momentum here. There's somebody, there's a kid who's going to sit down and like work his ass off to make this happen. Like I can spend an hour a week with him to like pull this thing together and like make it really high level and make it something that David's going to be proud of and make it the Founders book that we all want to exist in the world. And I don't know. I'm super excited about it. He's an animal. I mean, he's like grinding constantly on this thing, and I think it's really, it's going to be really cool to see it like coming together.

David Senra: And hopefully we sell a lot of copies. Listen, I'm already hearing the Founders ad of this, like weaving in the whole story, like I already know what I'm going to say and even I bet you people buy it even if they didn't want to read it just because they want to support this kid. I don’t think people understand how much self-published authors can make. And you're obviously a perfect person to ask. Millions upon millions upon millions. And again, I don't think this kid's doing it for that. But if he does this right, there's a huge economic upside to that. Can you speak to that a little bit?

Eric Jorgenson: Yeah. I think he is where I was when I started the Naval book, which is just like I want this book to exist. I want to spend time with these ideas. I want to show like respect for this person whose ideas I admire, and I want to be made better by going through this process. And I think he will get all of those things. But I didn't expect to make money off the Naval book. In my wildest dreams, I was going to break even on the Naval book.

David Senra: I know what you made, but do you talk about this publicly or no?

Eric Jorgenson: I don't love to, but I'm okay with it. Just to do the napkin math, it's not a ton of money to publish a book. If you bring a manuscript to Scribe, we'll publish it in all the formats for $26,000. Most books on average only sell a few hundred, a few thousand copies. So, the median outcome is not amazing there. A self-published author can make between $3 and $12 per book, depending on the channel that you sell through, but call it $3, 4, 5 on average. So if you only sell a few thousand books, you're going to break even. If you sell 10,000 books, it starts to be like, oh, this is income. If you sell 100,000 books, it's a really good... That's an asset worth six figures. If you claw your way up the power law and you're selling millions of copies of books, it's like being the founder of a business. Like you're cash flowing hundreds of thousands of dollars.

Mitchell Baldridge: And a business with 90 percent margins that can run forever.

David Senra: Is Goggins the one that is- who's the best-selling self-published author?

Eric Jorgenson: Probably Goggins. Goggins in non-fiction memoir for sure.

David Senra: Yeah, non-fiction. Because you guys did, Scribe did that, right, or no?

Eric Jorgenson: Yeah, Adam [?] ghost wrote that book. And we published it. So, I mean, Goggins invested a lot and worked his ass off on that book.

David Senra: I mean, I bought two copies. So, like he probably, what, sold 3 million, 2 million? Something like that?

Eric Jorgenson: I think he sold 5 million copies, I mean, and that was an old figure. And he's done a lot of speaking. So, he's making a lot. He's done really, really, really, really well off that book and he deserved to. Him and James Clear are really unique in this because like, and I think actually early Tim Ferriss is unique in this. A lot of authors treat their book like a side project or like it's part of their business ecosystem, which is fine. That's a totally reasonable strategy. Those authors who are like household names sold one product for years. They sold Can't Hurt Me or Atomic Habits or 4-Hour Workweek, and that was their life, was promoting that one product and pushing it as far as they possibly could for years. I think that's where you see those breakthrough results in household names. And I really use that phrase a lot now, clawing your way up the power law. Because every incremental percent or half a percent or tenth of a percent can have massive difference, like six-figure difference in the total eventual outcome of the value of the thing that you're creating. It's the same in podcasting, I'm sure. The incremental effort between being in the top 1% of the top 10th of a percent is the difference between being like a hobbyist and a true like high earning professional.

David Senra: And like, there's a bunch of stuff that I've been like learning even more about podcasting and I can't talk about yet. And it's just like it... Really, this is why I told you, dude, whether like a main publisher wanted to do this or these other like independent publisher councils. I'm like, dude, if I ever do it, it's gotta be with Eric.

Mitchell Baldridge: When I wrote my note about this founder, you talk about DMing people and providing zero value and expecting your life to change. And Waulter DMed me on April 26th and clipped me... Waulter DMed me on April 26th and basically clipped me for 10 seconds talking about this book and said, working on it. And I never replied because... And then the next time I heard from him was May 25th, one month later. So I did it. And then I said, nice, let's see it. And then he sent me the tweet of you, of this beautiful book that he'd created for you that is not the Founders book, but it's just like, nobody does that. Nobody works for a month on something and spends their own money and spends their own time to build something that they want to see. And everyone sends a DM, hey, I'm going to do this idea. Ideas are a dime a dozen and saying you're going to do something is free.

David Senra: And look at all the- look at all the unpredictable positive externalities that come from something like this. Like, now he didn't- now he's going to get a shot at this. And if you produce something great, it's going to be promoted as much as we can. We're talking about it on your guys’ podcasts... He got to spend hours with me, Patrick, Kareem and Eric, like he's just got all these people now in his corner. They're just like, yeah, man, like we have access to resources and like a network. And if you're going to keep doing shit like this, then like you just opened the door for yourself.

Eric Jorgenson: This is an amazing example, actually, of like entrepreneurial zeal creating something, like taking space from something. Like the Founders book as a concept has been around a long time. It's basically on like both David and my just kind of like mental backburner until he came around and showed enough momentum that he's like, I'm going to make this happen. I will be the vehicle through which this happens. Please shape this however appropriately. But there's going to be a Founders book in the world. We are all going to find ways to enable it to happen basically because this person showed up with like enough energy to create something where nothing existed before.

Mitchell Baldridge: It's uncovered gold just sitting right there that exists so many places. So many people send me kind of these low effort DMs of like- think about the scripted DMs you get of, what if I could bring you 25 plus paying customers, or better yet, 25 plus meetings next month. I'm like, I do not want one meeting next month. I do not want 25 meetings next month. I always just reply to those guys, and I say, look, if you send me a customer, I'll give you a thousand dollars. And if you send me 1,000 of them, I'll mortgage my house and give you $1 million. Or like just, you know what I mean? Like, I will give you as much money as you can send me customers, but...

Eric Jorgenson: Don't cold DM me and pitch me ghostwriting from an account with 200 followers.

Mitchell Baldridge: Exactly, like, yeah, do me a favor. Go get 90,000 followers or whatever and then come back and pitch me ghostwriting.

David Senra: And I think... how long did it take you from inception of the idea to finished product for the Almanac of Naval?

Eric Jorgenson: Three years. It was a long time.

David Senra: Yeah. So like that's the key here...

Eric Jorgenson: It was nights and weekends and I went through a ton of different like creative challenges and stuff like that. So I mean, we're going to be able to go a lot faster because I know how to run this system now, but... figured out how to do it.

David Senra: Yeah, it's definitely not going to be 3 years, but that's the key too, because I was like, listen, man, like I think people are like in too much of a rush. And it's like, man, you want to make something great because like the Goggins book is still selling. It's probably been out for what, five years, six years, however long. I see Atomic Habits everywhere in the world. Like if you just make something great, like I'm working on, I'm finally doing this, because people are always like, who are the top people that you haven't met yet that you want to meet? And one of my favorite documentaries is The Defiant One, so it's like fuck it, man, like I keep talking about this documentary. I keep talking about the fact that I really admire Jimmy Iovine, so I'm working on this Jimmy Iovine episode right now. That's why I was telling you guys I’m texting you, it’s late. I haven’t showered today. I haven’t gone to the gym. I’m completely in love with what I’m doing right now today. Like today. I haven't eaten. I drank three coffees and like a bunch of these like Element drinks. But like what's crazy is because I'm also trying to get lost in his world and he made some of the beginning of his career, like this is like the 1970s, early 1980s, and he's talking about the effort that went into making some of these records or these, whether it's an album or an individual song. And then I go and find the song I've never heard before and I'm like this shit sounds still good 50 years or 40 years later. Like this is great. And then you figure all- like they did 250 takes. They spent weeks on a single song. It's just like take your time with what you're doing. It's way more important that it's great than it's fast. This book in front of me is fast. It's interesting. It'll prompt your thoughts. But I guarantee you, if you spent two years on it instead of a month and he had- like he didn't pick the timeline. He wanted to do it when I was doing this event in New York. It was like, it would be a thousand times better. Yeah, I think that's the big thing. Just slow down, like take more time. Same thing with like people, I think the issue people are having, one of the reasons that books are so valuable, it's because of how long they take to consume. It would not be nearly as impactful if, this is Bruce Springsteen's autobiography I'm eventually going to get to, and I don't know, it's giant. I could hit you in the head with it and you’d probably have a concussion. And it's probably going to take me 45... to make the episode, if I was just reading it laying on a couch or something, it’d probably still take like 30 hours. To make the episode, it's probably going to be like 50 hours of reading. But the impact I think this guy is going to have on my life and the book’s going to have on my life, because I spent 40 or 50 hours on it, then if I did it in like two, it is not comparable.

Eric Jorgenson: So, there's a few things there. One is Nat Eliason was on a podcast a couple weeks ago, and he had a great frame, which is like books are one of the very few things where you can sell the exact same file for 50 years, and people love it just as much. They gain just as much value from it. And actually, it's one of the things that I think about that makes Founders unique from other podcasts is like Founders has the same feeling. Nobody understands that yet because podcasting is still too new. Nobody's been like listening to 50 year old podcasts, but they will be.

David Senra: That is something, like I've been spending a lot of time with the top people at Spotify and like they've figured that out too. They're like, I don't think there’s anybody else in podcasting that is building a catalog like you're building.

Mitchell Baldridge: It's like remember when serial hit the world and people were... binge listening to serial podcasts. Well, you have 300 episodes or you'll have 400 episodes that can be binge listened, and you see people fall down the rabbit hole. Like have them pull... Yeah, have Spotify like pull data about that, about people falling down the Founders rabbit hole.

David Senra: So, our mutual friend, Hinkie, Sam Hinkie, and I were texting the other day, and I was like, should I do an episode on the Power Broker? He's like, his answer is going to be like, obviously yes. But the crazy thing is... Yeah, so this is like they literally had to cut like, I don't know, 30, I forgot what he said one time, 30% of the book because it was as big as a book could be before...

Eric Jorgenson: The physics of a spine don't work anymore.

David Senra: And it's just like, let's see, this book was published in 1974 if I remember correctly, and it's still selling, and it's, yeah, 1974. It's published in 1974. It's on every single top 100 list of best non-fiction books. And I thought somebody said like in the last decade, it was selling more now than it used to sell. But like, why? Because like you couldn't make this again. It was like an unbelievable amount of effort and time went into that.

Eric Jorgenson: Will and Ariel Durant, same thing. Like, I don't think there's been as good of a historian since then. They're still the best history books written as far as I'm concerned.

Mitchell Baldridge: Go walk in New York... walk in New York City and look up and stare at the Chrysler building. And could you build that again? Like there are these relics of time that people will build amazing books like The Power Broker. But they're just... It takes, to your point, like hitting bottoms, not a weekend retreat. Like you don't get this done in like, you don't get this done in a year. Like you have to take 10 years to do it. I think about that in terms of just like, I had written on our notes just bootstrapping a holdco and like how long shit takes, and it's just like I get frustrated in the day or the week or the month, but great things take time.

David Senra: I never heard you describe that you're bootstrapping a holdco. So, if I haven't heard it, then the audience hasn't either. So, what are you doing?

Mitchell Baldridge: I have these companies. We have this cost seg business, and we have this accounting firm, and we have this better bookkeeping software business, and then we have this-

David Senra: Take them one by one real quick, because remember, you're not- what did Ogilvie say? You're not advertising to a standing army, you're advertising to a moving parade.

Mitchell Baldridge: They can go... You should have listened to the whole catalog of these before you got here.

David Senra: I guarantee you they didn't, so like...

Eric Jorgenson: They're here for Senra and they're getting Baldrige commercials. Let's go.

Mitchell Baldridge: Sorry, sorry this happened to you.

David Senra: Let me see how much I know. So you have RE Cost Seg, which I know might be your biggest business. Right?

Mitchell Baldridge: Today, yes. Yeah, sure.

David Senra: You do it with Nick Huber and your wife.

Mitchell Baldridge: Yes. Yes. I’m nodding.

David Senra: Okay. It is the audio...

Mitchell Baldridge: I'm nodding for the listener.

David Senra: Okay. So you do it with Nick Huber and your wife. Okay. That business does what exactly?

Mitchell Baldridge: So, it's an engineering services firm that helps real estate investors save on taxes. We prepare these reports that basically outline the blueprint of the building and tag tax lives onto the individual elements of the building. So if you buy a retail shopping center, you think, oh great, I bought this building with all these tenants inside of it. But we run an engineering study that looks at the building from its component pieces to see specifically how much five year, seven seven-year, 15-year, and 39-year assets you bought so that we can depreciate the building much, much quicker and lower your cost of capital.

David Senra: Okay. So, I, as the business owner, would want to do this why?

Mitchell Baldridge: Because you would save on tax the year you place the building into service. You would, instead of getting $40,000 of depreciation on a million dollar building, you could get $300,000 of depreciation on a million dollar building.

David Senra: So really the way to think about this is you sell money.

Mitchell Baldridge: I sell... Yes, I sell tax savings, baby.

David Senra: Exactly. You're selling money, which happens to be great businesses. And there's a lot of these examples of selling money that generally works well. So let's like give an example just to make this as clear as possible. It's like, hey, I'm a business owner. I'm going to pay you $5,000, $10,000?

Mitchell Baldridge: Sure. Yeah. You're going to get a proposal.

David Senra: Use a real example. Somebody paid us five grand, whatever the number is, and they save 50.

Mitchell Baldridge: Sure. So you're going to hand me your business, the property address, what you paid for the property, and what, if anything, you've paid to improve the property. So you're going to say, hey, I bought 19 Main Street, which is a retail shopping center, and I paid $3 million for it. And we're going to turn back a proposal to you that says, okay, you're going to pay us $4,000, and we're going to save you $100,000 of tax year one. So, it's a 25 to one payback ratio.

David Senra: An example like that, you save somebody $100,000 the first year of taxes, you would charge them what for that service?

Mitchell Baldridge: We charge based on the project and not based on the tax return, but... Yeah, so again, a shopping center might be $4,000 or $6,000. A little beach house might be- we have this product called the Rapid Report that it's $895, I think, or...

David Senra: Okay, there's nothing illegal about what you're doing, right?

Mitchell Baldridge: No, it's very much legal.

David Senra: Okay, so therefore, the business, the only constraint from the business growing is people being aware of its existence and educating the market of why you'd want to do this.

Mitchell Baldridge: Yeah, and then at the outsized, wildest end point, you've captured the entire market and saturated every real estate investor.

David Senra: But by that time, your wife never has to fly commercial again.

Mitchell Baldridge: That's true. Yes, very much so.

David Senra: All right. So I think that's easy to understand. You're getting customers mainly through what channels?

Mitchell Baldridge: We bootstrapped it on Twitter through our Twitter audiences, but we've gone to, we now have a whole base of customers. So we go to our customers to refer other customers. So it becomes a referral business at scale. We use paid advertising, SEO.

David Senra: Do you pay existing customers for referrals? Do they get something for referring new customers?

Mitchell Baldridge: Yeah, I think right now, we have the $500 Refer a Friend program. So, we're betting that the LTV of a client is more than $2,500.

David Senra: You guys have advertised with our mutual friend Chris Powers on his podcast. Did that work?

Mitchell Baldridge: That did work.

Eric Jorgenson: Was this born out of like you were getting really shitty service from the other cost segs. Were they overpriced? Were they...

Mitchell Baldridge: It was born out of just it being a good business model. And in my vision, yeah, they were charging a high price and they were flying to the property and circling around the property with a clipboard and not using any kind of like labor leverage or systems leverage to deliver the service better, faster, cheaper. And so we came in and started using virtual site visits, started systematizing the process of delivering the service, started scaling sales a whole lot, scaling deliveries, scaling customer service, and it resulted in, yeah, better, faster, cheaper. The thesis is turn everything into a car wash, where you just drive up and put your car into neutral and you have it pull you through the experience and send you out clean. So, like RE Cost Seg is a very, very specific problem with a specific client, with a specific set of steps and systems that put the entire project on rails. And Better Bookkeeping is the same thing. Solo founder, solo business owner, real estate broker...

David Senra: ...people you're doing, like there's multiple co-founders that are customers of Better Bookkeeping. Essentially, like, hey, if you don't have a super complicated business, but you want straightforward tax planning and filing, it's X amount per month. It never changes. And like you guys do all the quarterly taxes, you do your tax return, you optimize for the tax rate. Okay, it's just like straightforward, but easy to sell.

Mitchell Baldridge: We kind of systematized the whole process by selling to one customer with kind of one concern. So then when we ship a update or when we ship a feature, it applies to everybody in the system and the whole experience gets better for everybody. Where we go, oh, well, we just rolled out the QBI calculator. So now every quarter, you get this quarterly email that shows kind of where you stand for QBI, Qualified Business Income Deduction, how you need to plan around that, how much time you have, and gives you a little health check report. Well, by shipping that feature, we shipped it to the entire customer base because everyone's the same.

David Senra: I think everybody's on the same page about what your holdco is, but your note was like how- it said bootstrapping a holdco and how long shit takes. So now that we know what the holdco is, like what was like the thought behind that to me?

Mitchell Baldridge: To me, I get frustrated at times that this all isn't going faster, but then I also want to do something... Exactly, but I want to do something that's big and meaningful and impactful.

David Senra: This is the key, man. This is the key. I love the climb. I don't care where the summit is. Have you ever seen this clip of Jerry Seinfeld? He's in the bar area in a nightclub. And this guy, this other comic, is just seeking his advice and kind of complaining to Jerry about like how long shit takes. And he's just like, I don't know how much longer I can do this without really achieving success. I see all my friends getting married and getting jobs and buying houses. And you got to really watch the clip. We should find it and put it in the show notes because like Jerry's face is like, ugh. And then it's just like, well, like- And then guys like, how much should I- how much more time should I give this? He's like, you got somewhere else you'd want to be? Like, you should love it for the activity, the sake of itself. Not like, oh... and the guy's only like, I'm 29 years old, I'm getting older. And Jerry's like, what? He looked at him like what are you talking about? And I just love that idea. And he tells this story of... because Jerry's... like there was never another job for me than being a stand up comic. So, this is the best version of my life, whether I'm selling out 300- I'm performing in front of 300 people at the improv or 3000 in the theater, like there is no better job. And it's like, if that's not for you, if you're like, well, I could be a stand up comic or I could be a fucking investment, I think he said investment banker, and Jerry’s like, what? Like those are not the two same things.

Mitchell Baldridge: What does that mean?

David Senra: So, Jerry illustrates this point where like, I forgot what it was. There was like this famous band, a rock and roll band in the 1970s, and they're on their way to a gig, and there's bad weather and so they have to land like at a different airport. And then they're like having to like walk through like a field that they weren't expecting to be in. It's like all- it's like raining or snowing and they're all cold, and they're like uncomfortable and they're walking through with like their big guitar and all their equipment. They're in like knee, ankle deep snow. And then they see this house and they walk up to the house, and they look in the window, and it's like this like family sitting in front of a fire and like there's two kids. And they look at each other like, ugh, how do people live like that? And so like, people are like, who the hell wants to do this? You're in the snow, like you almost like- you had to land in a cornfield or wherever the hell the story was. And Jerry's point was just like that. It's like, what do you want to do? You should just be like, there's nothing else that I'd rather be doing. So if it's going to take a long time, you got something else that you'd rather be doing. And if you have something else that you'd rather be doing, then you should be doing that.

Eric Jorgenson: I mean, it's a Navalism, like you're retired the minute you're no longer sacrificing today for an imaginary tomorrow. Like when you were doing the work... for its own sake. Yeah, it's in there. But it is hard. Like, I think, Mitchell, the tension you're talking about of like, it is also like normal to do that in service of like this grand vision that accumulates over many years. And like, the other Navalism that I like there is like impatience with action, patience with results. Like if you're impatient day to day, maybe it's because you're not actually working on the highest leverage thing that gets you towards that ultimate thing. Like I think we all know we are all patient people for results or we wouldn't be in the games that we're playing. It took a lot of patience to even get here, but knowing that all the compounding is still to come, I don't know. When I'm finding myself impatient, I'm usually micro-impatient. And then when I have a moment to zoom out, because the weeks are turbulent, and then you look at the quarters and you're like, oh, that looks like a steady up and the right normal growth path, but it felt like a fucking roller coaster every week.

David Senra: There's something for me, obviously, I'm very tightly wound. I remember the first time me and Eric met, it was in person. I think he just realized there's this weird bounding energy coming out of me that's like, can be kind of uncomfortable.

Eric Jorgenson: I love it.

David Senra: One thing that helped me was like, obviously, you just did this great post about like some maxims that you've heard on the podcast or whatever. And I like collect maxims and I think they're very helpful. And so, one of the things that like, anytime I'm feeling stressed and like my whole thing is like, yeah, super impatient, want things done better, faster, like I think most people are like that. But I heard this thing that anytime I'm feeling like super stressed out, it's like, yeah, but that's what you wanted. There's this great line from Herb Kelleher, the founder of Southwest Airlines, where he's like, he was 35 years old when he started Southwest, he was an attorney. He could have been successful living in Dallas or Houston or wherever he was, rich enough, didn't have to do the shit he's doing. And his J job would be a lot easier than trying to start a brand new airline. And somebody asked him one time, they're like, how do you handle the stress? And he goes, I don't handle it. I like it. And so, anytime I'm... I swear to God, like anytime I'm feeling stressed or angry or like everybody- the entrepreneur emotional rollercoaster, I'm like, ah, I love this. Like, this is what I want to feel. Jimmy Iovine was talking to one of his vice presidents at Interscope. And he's like, you know what your problem is, Steve? He's like, you're like this. The guy is just completely even keel. He's just a straight line, smooth. And he's like, you need more of this in your life. And what he's showing is like ups and downs and ups and downs and ups and downs. And I think there's like a lot of wisdom in what he's saying, because most people want- most people do not want the ups, or they want all the ups. They don't want any of the downs. They don't realize to get the ups, you have to endure the downs. That's just a fact. And so most people try to just keep it nice and even, not too happy, not too sad, not too successful, not great failure, whatever the case is. But all the exciting shit in life, and one of the reasons I admire Jimmy Iovine so much is not just that he was a very successful entrepreneur, there's a lot of people way richer than him. It's like he lived a remarkable, crazy life with a lot of experiences that I'm sure as a man in his 70s, close to 80s I think by now, or 70, he might be 72, something like that, he could look back, and he said this on a bunch of podcasts, and tell these amazing stories. It was because he wasn't afraid of this, of this variance, of these highs and lows and highs and lows. And so if you're picking this lifestyle, which all of us are, which Herb Kelleher picked, which Jimmy Iovine picked, it's just like, yeah, you don't handle the stress. You like it, or else you wouldn't be doing it.

Eric Jorgenson: David, is this the story, you put a note on here, Billie Eilish and Phineas?

David Senra: Oh, so yeah, this is really interesting. I take a lot of inspiration from hearing, I'm obsessed with filmmakers, of how- I think some of the best episodes I've ever done are on filmmakers. Christopher Nolan, Quentin Tarantino, James Cameron, George Lucas. I'm obsessed with how they push their craft, how they think about it, the businesses they build around it. There's so many analogies for entrepreneurs just hanging there. There's so much much gold in there. And musicians as well. And the way Bruce Springsteen was, I'm going to do an episode on Prince, on the Beatles, like I've done on Jay-Z and the way he approaches his craft. It's like, man, this is just like, this is entrepreneurship. It's just like you just have to turn it into an abstraction. And so I don't know anything about Billie Eilish or English, Eilish, I think. But yeah, so my daughter would listen to her stuff, and I saw like this random clip about I guess her and her brother are like really deep creative partners. And then I wind up watching like 20 minutes of them talking about their partnership, what each one brings, what they like, and I thought it was very fascinating that Phineas, who I guess like writes a lot of the stuff for her and like kind of produces, I guess is the way to think about it. He says that I love the process of making a song. Like if I could have my way, he's like I want to be in a room every day making the actual product. This is the analogy for or the metaphor for entrepreneurs. Where Billy likes having made. And so, the most exciting part for her is when it's done and she gets to listen to what she made. And what I realized is in terms of podcasting and why I don't like outsourcing stuff, it's like I like both of those. Like why I was late here, because I'm in the process of making the podcast. I told you I hadn't showered yet. I hadn't eaten. Like, I didn't even work out yet. Like, because I was like really obsessed with where I was in the process that I didn't fucking realize how much time had gone by. And so, I like the process of it. And I like then having made and then because when I'm done, I listen to the entire episode before I put it out. And you will catch me listening to my own podcast, podcasts that I made six months ago or a year ago. And it's not like- because you forget that- we forget that we forget. And I'm like, damn, there's all these ideas. Like to me, what I'm making is like a tool for entrepreneurs, but it's also a tool for myself. Like in a 45 minute or hour long episode, there's going to be ideas in there. And if I don't re-listen to them, I will forget those ideas. It's like a reminder. Yeah, I thought like, oh, that's interesting. The way I approach it with podcasting is like kind of a combination of how they approach the actual creation and then the end result of the music that they’re making.

Eric Jorgenson: I love that. That's how I feel writing books too. This is- I'll tell the story like more when we get closer to actually like launching the Elon book, but I have- when I was like deep in the early stages of the Elon book, it was right after my lung collapsed actually, and there's like a photo of me sitting up in a hospital bed at 10:30 on Oxycontin with oxygen in my nose, working on the Elon book the day I had surgery. And I couldn't do anything. I couldn't work out. I could barely sleep. But I still carried my laptop everywhere. I had an AirPod in 24 hours a day, like working on this book, like grinding it forward because I knew that this was like, it was all I could do. It was super satisfying to move something forward that I cared about, even while I couldn't do anything with my actual like body or even like leave my apartment or walk. And it was super- it like helped me so much through that period to just know that I was like contributing something in moving this thing forward. Because yeah, if you love the product and the process, like that is a beautiful system.

David Senra: Just like going back the Jerry Seinfeld thing, go back to what started this. You got something else you'd want to be doing, Mitchell? Because if not, then you're exactly where you need to be. And then the discontent you feel of the time, okay, well, that's a problem to solve. Then you just reverse engineer. Okay, well, this thing I think is taking- this is the progress we made over the last 12 months. I thought it should have been, it's X, it should have been Y. Well, then how do I make X and Y? Then it gets fun. It's like a game. It's like, oh, and then like you start and figure it out and then you experiment a bunch of stuff. But like, I think that’s the key. Too many people don’t... how you are spending work is going to take up half of your life. You should think deeply about what the hell that is. And it shouldn't be like this- I mean, listen, every single person in my family, most of the people I grew up with... it's just like, they just wanted a job. Like there's no thought into it at all. And if you're in a position where you can actually pick and choose what you work on, like, first of all, that's like completely ideal and you should really take a fuck ton of time like contemplating who you are as a person. This is the biggest thing about the Michael Dell episode that I did, which I think is one of the best episodes I ever did. Michael Dell’s like tweeting about it, which was really nice. He like posted about it on LinkedIn. I'm actually going to meet him soon. And one of the things that his autobiography did for me that was so great is that he gave better terminology to this, that you should build a business that's completely natural to you. I was using the word authentic, and although I don't think it's a bad description, I think natural is a better description. And the example in that book is Dell is like in his early 20s, and he's literally like, I'm going to fucking compete with IBM. And IBM is the most valuable company in the world. I didn't know at the time, the first company to build- to break through the hundred billion dollar market cap. And he's like, I'm going to start with $1,000 in my dorm room and I’m going to compete with them. And so, a few years into this, he hires this guy, this other entrepreneur who’s like 20 years older, called Lee Walker, if I remember his name correctly. And Lee lasts like, I don't know, three or four years, but he talks about the end, why he had to leave. And he's just like, man, like the competition we were in, how fast we were going, we were just like, we're playing the game of kings. Like this is competition at the highest level in the computer industry at the time. It's so complicated. It's so stressful. It's like every day, there's a million problems. So he's like, my hair started falling out. My back was killing me. Like I couldn't sleep. And so, I literally couldn't last any longer. I was going to die. And yet, Michael's going through the exact same experience, and Michael's energized by it. He's just like- his back's not hurting. He could sleep like a baby, the little bit that he is sleeping. He's like so energized because Lee said that Michael built a business that was completely natural to him in a way that Dell was unnatural to Lee at that point of his life. And I'm like, damn, that's such a perfect encapsulation of like how if you're trying to achieve the most amount of success and impact in the world, like that is why he started his company at 18 and be in his 60s and still doing it because it is natural to him as it is breathing.

Eric Jorgenson: Mitchell, do you feel like your business is natural to you?

Mitchell Baldridge: Yeah, I think so. I think that the big thing I've been thinking about in terms of the broader array of services I'm offering them or offering today is like, how do I flatten this all down to offering instead of a ton of services, trying to like just offer the layer of human touch on top of Ramp. I mean, I put in my notes, David, that the world is going to become a wrapper for Ramp. This episode is brought to you by Ramp. And so is...

Eric Jorgenson: Ramp hasn’t paid me a fucking dime for the record.

David Senra: You have your own company that's sponsoring this.

Eric Jorgenson: No, I got open ad spots.

Mitchell Baldridge: Check’s in the mail, Eric. They're going to make it right.

Eric Jorgenson: I mean, this is exactly the kind of thing. I think the low cost strategy is the right one in this. If you can smash- nobody wants to pay more for accounting or tax services. Assuming you don't go to jail, compress costs down. And this is an incredible tool for doing it. You still need some trust in the person or the ultimate outcome because the relationship is going to determine sort of the purchase. But yeah, you like... And this is the same playbook you've applied. You've organically grown by listening to the customers that you already had, a bunch of different services. The playbook is roughly the same for all of them. The operating system should probably get turned cohesive across all of them, so that you can manage this increasing scaling holdco. The people I know that are doing that well are implementing the same managerial system at each company, so that you as the emperor can quickly dive in and out of different businesses rather than like figure that out. But it also depends how much leeway you want to give your operators. Like if you're going to do a Buffett style rather than a...

Mitchell Baldridge: Sure. I just think... I think that the tax code in the world is getting increasingly more and more and more complex, but these systems are getting increasingly better and better and better in dealing with the mundane and the normal. So it's like, how do you normalize the problems to flow through these systems? I mean, David, what has changed your mind or how have you like changed your mind in the last 180 days about AI?

David Senra: I don't remember, was it 180 days last time we recorded?

Eric Jorgenson: Probably a little more actually.

David Senra: Yeah, like as soon as you start using it...

Mitchell Baldridge: I don't know if we even talked about it.

David Senra: Yeah. So like, no, it's obviously useful. Like, so that was the biggest issue. Remember, like people would go on podcasts and they debate about crypto? And there was like one guy, I forgot his name, but he just essentially, like they kept sending all these people from the crypto industry to debate him on other people's podcasts. And he would just keep winning because he was just like, tell me one use case. And so like a guy would come up and like, just tell me one use case. And it'd be like something super complicated you could do better and easier today. It's like, nope, that doesn't work. And then next week, another guy would come up, and the guy just kept winning every single fucking debate just by saying, like, how can I use it? Just tell me. This is what I mentioned earlier. Like I really... I really like distilling things down to its essence. When I was asking you to say, okay, like what's the product? I own a building. Okay. I pay X amount of taxes. I go to Mitchell and say, help me figure out how to pay less taxes. Like it just like simplify this as easy, as much as you can. And like how valuable is it to have essentially an assistant that has read everything ever written? It turns out pretty fucking valuable. Like and then it's like if you don't believe it, just start using it and then you'll use it once a day. And then you'll go, oh, and use it two days. And now it's like you see this, I think they just said that like on average, the usage time, the daily active usage for ChatGPT right now is something like 20 minutes a day. Like that's definitely me, at least 20 minutes a day. Like, and I pay for them all. I don't care. I pay for Claw. I pay for Perplexity. I pay for OpenAI. People bitch about $20 a month. It is insane. I paid $200 a month to Open AI. I pay the deep research feature on Open AI or ChatGPT rather, is I pay, add a zero on to that and I'm still paying for it. And I would still pay for that because like obviously I’m now using it to like help me research podcasts and do all- and just like learn about the world around me. It's like...

Eric Jorgenson: What do you use it for?

David Senra: What? The deep research, essentially like over and over...

Mitchell Baldridge: When were you able to like loop it into your- where does it sit in your process like stack today? And at what point in time were you like, oh my God, I can't live without this?

David Senra: So, this goes back to like I'm obsessed with people that take the things, what they're doing, take whatever they're doing very seriously and do it for a long time because then you talk about it, you get into how you think about it, what you do. If you just think about the same thing over and over again every day and then you do it, you're going to come up with a lot of useful process and ideas that other people don't. I know a bunch of other podcasters, think about all the information. If you have a fucking business podcast, all the ones that we're friends with, they've been doing it for like six years, seven years, five years, whatever it is, like how much information you have produced. And then all the research that went into it. And I'm like, where's all your research? Like, just like sitting in a file somewhere. And so, like this, the random like lucky idea that I had, and it wasn't even mine, Tristan, the founder of Readwise sent me a DM or an email maybe, and he's just like, hey, you read a lot. I like your podcast. Maybe you should use this. I’m like oh shit, like yeah, I should put my notes and highlights into this giant database and then accumulating twenty something thousand, whatever it is that are in there. And then five years later, partnering with them to build like my own version of that and then layer AI on top of that. So now I have something that's like, yeah, these other models, they've read the entire internet. Sage has read every transcript I ever had, every note, every highlight. And it turns out it's like super useful for me to build the podcast, even if I didn't sell it as a product, like even if I stopped selling it, like I would still use it because dude, I have so many- I don't even know, I'm not going to count how many open browsers because as I'm reading or researching with Jimmy Iovine, I'm fucking asking questions about this. Like a friend calls me, and I fucking use it all the time. So yeah, it wasn't like an inflection point. It's just like any tool. If it's useful, if you find a hammer useful, you're going to pick up more. Like it is that... As I spend more time with it, do I get good results from it? And so it was funny, Mitchell has a good example of this where somebody's like, I forgot what it was, but somebody says, entrepreneurs don't do whatever. And Mitchell just asked Sage, can you give me examples of whatever that guy says they don't do? And it literally, do you remember what the- what he was saying?

Mitchell Baldridge: I don’t. But yeah, it just- I was like, this is wrong. And I'm like, okay, I have access to Sage, which is, I don't have to text David so that he can ask Sage. I can just ask Sage, and it literally- I'm like...

David Senra: Yeah, the guys like duly noted. Yeah, that was the biggest thing where essentially, if you think about, you have the hyper-focused part of like, if you tap into the collective knowledge of history’s greatest entrepreneurs, which is what I'm interested in, but then the broader thing of like tapping into everything that's ever been on the Internet, which is like a daily- a normal person using ChatGPT or whatever. Like the reason I knew these were powerful is because before doing this, like think about when I got to talk to Charlie Munger and Sam Zell, it's like they had this and they had Sage in their head though, and they got that through six decades of experience. They'd read every single book. Like I told you, I've told you this before, like I couldn't throw out a book recommendation that they didn't already read. Like they made me look like an amateur at this. And so like, obviously it's valuable if you can pull it up on demand. And now we're going to be able to have the tools for every single different domain instead of... for every single thing, you're just going to have essentially an assistant and then eventually an employee or a coworker that has access to the collective knowledge of human beings. Like if you can't find useful ways to use that, you can't find useful ways to use anything.

Mitchell Baldridge: Hype cycles come and go, and this one...

David Senra: I'm not speaking to whether the businesses are valued, like if they're ever going to turn a profit, if they deserve the valuations they’re getting, I don't give a shit about that. I care about products.

Mitchell Baldridge: The downstream idea.

David Senra: Like if you're a gifted entrepreneur, you understand that eventually, like you're going to have to bring in more money than you spend, like that's obvious. That's not going to change. But what I'm talking about, so like I’ll give an example, I started using deep research as a supplement because sometimes you're reading these books. It's just like, like I remember the first time that I started quoting from deep research on a podcast. It was the episode I did on Jerry Jones. There's like one biography of Jerry Jones written like in the 80s or something or I forgot when it was, maybe mid 90s. But there was like gaps in there I didn't understand. And so, the way I use deep research a lot is because I love reading like New Yorker profiles, like take- spend a few months making a profile on somebody you can read in like 40 minutes. So it's not a book, but it's not like a tweet. And the storytelling is really great, and if you want more, you go find the book. So, I just started having deep research make me like New Yorker profiles on whoever I want to learn about. And almost every single time, like yeah, in fact, I can't remember the last time I did an episode where I don't also have a deep research report on it. And the good thing about deep research is like it's going to tell you sources. Listen, man, right now, some of the sources still suck. I'm like, oh, I'm not using that. That looks shady. But some are really, really good. So again, if you're willing to spend more time and not just take everything that ChatGPT spits out as fact and like research it, there's going to be days where like, I guarantee you, I'm going to be able to do entire episodes off of just deep research. That's 100% going to happen. And yeah, so that's like, what is that worth to me? I was thinking about hiring a research assistant. And if you're a really good researcher, it's going to be like a couple hundred grand if you want like top, top people, and I'm sure at the very top, like they're going to have a taste, a perspective, that it still might be valuable. But like, I think AI is going to destroy the middle for sure. Like if you're just an average research assistant, like why would I pay that person 100 or 200 or whatever it is? Like I'd pay 20- what am I paying now? Nothing. 2,400 a year. I'd pay like 10x that. There's so much room to grow from there.

Mitchell Baldridge: It's going to create- to your point, it's going to destroy the middle being everything below the 95th percentile because I think about like...

David Senra: They're going to make you- they're going to help you make better decisions. Like again, I say this over again. We forget that we forget. And what happens in a world where you don't forget anything that you need? And sometimes like there's stuff in my own podcast I don't remember. I’m like, hey, and I'll kind of describe it as like, I think I said this, and it was something like that. And then like Sage finds that shit for me. It's like, what is the value of that? Like to be able to pull up anything I've ever talked about. And then my whole idea, obviously, is like I want to collect more information on history’s entrepreneurs than anybody else in the world. And so, I'm going to keep doing that and keep finding weird stuff. Like, dude, the amount of books I'm reading right now that aren't even available in English that we're translating with AI. Like if you have a fucking brain, you could figure out like how... go back to Waulter, we're going to have to come up with a nickname for him, because there's no fucking way I'm going to pronounce his funky ass name ever correctly. So, W, we're going to call him Big W.

Mitchell Baldridge: Big Dub.

David Senra: Big Dub. So, one of the things we talked about with him, and Patrick gave him really excellent advice, and I was sitting there for the conversation, and it's just like you have to look for like what is actually differentiating the product that you're building. And so, for me, it's like working backwards from these tools. Part of it is like what can I- how can I use this to differentiate myself from anybody else that would try to do what I'm doing? And you think about that, and you see all this like wide open space. This is like a very good use case for something that is unbelievably inexpensive given the value that you get from it.

Mitchell Baldridge: They give you the base layer of understanding being the ultimate like word cell and understanding the entire internet and the history of everything on the internet for ever, ever kind. And then you get to layer on top this database... And you had those guys help build you an amazing product in Sage, but now you have this vector database of every note that you've ever taken, which is proprietary, and every idea you've ever had, which is proprietary, and then your entire podcast, which is public. And then eventually you'll jam in the entire text of every book you've ever read. Like it's going to get more and more powerful and better and better. And it's going to be so, even more so quintessentially you. It's going to be wild.

David Senra: It's funny, because I almost feel like I should rename it to like Text David or something like that. Like the branding... there's something around this, because essentially, this is what it is. It's like you've seen this too, where you mentioned it's like I'm not doing anything else, but keep adding more episodes, more notes, more highlights, but the underlying models, like in the last- we've been doing this for- we started this in 2023. What is this now? Like almost two years later. Dude, it's way better. Even if I did nothing else, I didn't add anything, but now we're using Claude 4.0 instead of whatever it was a year and a half ago, it's just like the way I think about it... it's like as if a smarter and smarter person is reading the same material... They're going to derive...

Mitchell Baldridge: The baby is growing up. You know what I mean?

David Senra: Not baby, but I think my example is actually better, but that's okay...

Mitchell Baldridge: It was an eight year old and now it's a 12 year old.

David Senra: No, it was always an adult. It was always an adult. It was just a smarter adult. It's like the difference between like-

Mitchell Baldridge: Hard disagree. A hill I’ll die on.

David Senra: But yeah, so it's like, and I already think it has a better memory than me. I was talking to another person where they think like I can still make better like connections, and maybe, maybe not, but like, for sure, it will eventually get better at that than me. Yeah, it's like, I just think like... it just unlocks more opportunity and ways to use it. And it's like an interesting like superpower to have that just wasn't possible, just wasn't possible. And the keyword search and everything else has been around forever. Like the way they tie everything together is just fucking incredible.

Eric Jorgenson: DAIvid.

Mitchell Baldridge: Yes. Lowercase d, AI.

Eric Jorgenson: David is unamused by my brainstorms.

David Senra: This is a good point where it actually made me think of something. I just did this episode on Jim Simons. Sorry, we reread that book, the Man Who Solved the Market the second time. and they had this thing where they were talking about- they're very like- they were very anti like narrative in the financial markets. There was this great story they told where they're like at the time, they weren't even- Renaissance technology was only trading like currencies and commodities. So I don't even think they were in, I don't think they were in the stock market yet. Yeah. And they had this point where they were buying, like they were like one of the world's largest buyers of like wheat futures contracts. And then there was a typo in the system. And then one day, they bought like, I don't know, they were already one of the biggest ones. They bought like 5 or 10x more than they were supposed to. And it caused the price to go crazy. And the next day in the Wall Street Journal, they're like, fears of wheat famine drives fucking rapid increase in price. And they’re like, you cannot ever pay attention to this stuff. But they had this idea where like the system that they're building, they use this analogy, they said, it's a bit like how bees see a broad spectrum of colors and flowers, a rainbow that humans are oblivious to when staring at the same flora. It's like you can't comprehend all this data that our system can. We're technically looking at the same things, but the bee is going to be able to draw, like we see all these other things that you can't. And really, what I was thinking about this for us and for in general is like two people can read the same thing or have the same experience and yet have two vastly different interpretations as well. And so in their case, Jim Simons and his team were like, oh yeah, that's true for computers too. And the example of this is like-

Mitchell Baldridge: Well, you kept saying in that episode, like they had to go trade their money on recommendations from a system that they didn't understand exactly how it worked and it couldn't tell them how it worked. It just said, hey, go buy Apple. And they had to just go, okay.

David Senra: And even if it could tell them, they probably couldn't understand it. So they eventually, it was slowly but surely, they trusted the system. They took the power away from the humans and turned it completely over. But the example I just got is like, one thing that I think the more I read, the more I'm able to comprehend and understand what I'm reading in a unique way, because I'm not just focusing on what I'm reading on the page, but everything I saw before this. And so, there was this dude, I told a friend of mine, he's like, hey, I'm going to actually like just take all of David's transcripts and everything else. Like, I'm just going to build a version of Sage, but I'm going to charge like a lot less. And I was like he doesn't understand one of the assets that I have is that first of all, I have distribution. Like, hey, you have this thing. You can learn from Founders podcasts. You can learn from this guy who has all the distribution or this guy who's going to be like tweeting into oblivion. But also, what he didn't understand is people do business with who they like. Like, this is something you don’t understand. It's like David has given me eight years of his fucking life, 400 hours, he's read hundreds of thousands of pages, distilled it down to something and made my life better as a result. Are you, some random fucking guy, who DMs- Cause there's also a guy on Twitter because he accidentally DMed me. He's just like, hey, this is how I found- there's two guys, one I found out because a friend and the other one DMed me saying that he built this thing. I don't know why he sent it to me, because he was trying to- I think he sent it to everybody that follows Founders or whatever, however it happened. But I'm like, you don’t understand what... I'm sure there's some people who might buy your thing, but way more are just like, no, I'll just go with the guy I know and trust and who's done something and made my life better, not some random fucking automated DM, AI slop bullshit that is in my inbox. And it's like, I was thinking about this, because like this guy who's doing this doesn't even understand what makes this all work. It's not just the- it's the complete system and like the experience that the person has had, not just hey, similar product, which it is not because he doesn't have all the notes and highlights, and less price.

Eric Jorgenson: This goes back to like, yeah, clawing up the power law, whoever does it best and how much you've given away. This giving away $5 million or 5 million copies of the Naval book and still selling a million and a half copies. People choose to buy it all the time. It's related to the story that you told earlier, but when I was a year and a half into writing the book on Naval, somebody was like, book on Naval when? And I was like, I'm working on it, man. Like, it takes time to do it right. And he was like, screw you, I'm going to do it myself. I'll get it out in three months. And I was like- It legitimately made my blood boil because I hadn't yet like realized that- I didn't internalize how different it would be yet. And you see a bunch of this bullshit out there. There's a million like quote books of Elon that somebody threw together in an hour and posted on Amazon. And none of them have reviews, and none of them have like anything. There's nothing. I bought a bunch of them to just like do research, and none of them are good. There's people knocking off the Naval book and scraping his tweets. And people respect quality and effort and story. And yeah, like the returns on putting years of your life into one of these projects and making it something like really, really excellent that actually serves the reader. I don't know, people are going to get- there's going to be so much slop. The slop is going to keep coming like crazy. And I think it's just going to make it more clear who these people are...

David Senra: Are you guys- do you guys know Jackson Dahl?

Eric Jorgenson: Yeah.

David Senra: He has one of my favorite new podcasts because how much care and effort he's putting into it. It's called Dialectic. And we've talked a bunch about this. I spent like five hours with him one night in New York recently. And I love the research he's doing beforehand, the fact that he must get on a plane and go to where these people are because he refuses to record remotely, which I think is a really good idea. But one of the things that I loved in one of his episodes, he said that Naval actually came up with the best way to use Twitter, which is to never read it and to just tweet all the time. I think as time goes on and everybody is just making essentially infinite amount, you just have all these fucking agents or all these bots making infinite content, you're not going to be able to read it. And if you are, it's a really bad use of your time.

Eric Jorgenson: Dude I think... internet theory is like arrived. I had a viral tweet recently, a couple actually, and like it was a heinous experience, like just insane bots berating you and calling you a Nazi and like crazy shit happening. And I'm like this is- none of these can possibly be real people. And even though I know that, it's like it still gets in your head... this is not- this is a like project only... I want group chats of friends that are actually like real humans. I only want to follow people that I know in real life or that are like super, super, super high signal.

David Senra: There's a great line from this rapper I like named NF. And he says, the mind is powerful place, what you feed it affects in a powerful way. And I don't think people spend enough time thinking about like, we just mentioned when we got on this, I don't know if we're recording, but like Mitchell looked all slim and like fit, very different than last time I saw him. Not that you were-

Mitchell Baldridge: When I was like the fat JD Vance baby.

David Senra: But like noticeably different. Yeah, noticeably different. And he talked about like he just changed what he put into his body. And look at the result. Like there's actually a good analogy here, like look at the result. Like yeah, he looks a lot better.

Mitchell Baldridge: And mewing. I was mewing also.

David Senra: But you literally, like you changed what you put in your body and now you look better as a result. Like what do you think you're just putting into your mind when- even the comments. And I'm in like this really kind of nice section of the internet where you have to be kind of a business nerd to even know about Founders, and so 99% of my comments are good. But I can't just imagine just reading, like I don't want all this- I don't want the opinions and the ideas and all this other stuff of the mass of humanity in my mind. I don't think to this day that I've come across a better source of material that nourishes me than reading these books and is actually nutritious, if you want to use that phrasing. I don't think there is anything else with that. Even the group chats with friends, I would say like in person stuff with friends or phone calls, like I call you guys. Most of the time, we don't FaceTime. Like I'm on a walk, and like we'll talk for an hour on the phone or Mitchell will be calling me driving around the giant state of Texas. Yeah, I think that's like, that's how I want to spend more of my time.

Eric Jorgenson: Yeah, that's a really good point actually and goes back to like books as this like incredible curation of so many hours, years of effort that authors put into them and like put in really close intention. And there's a line that I use all the time, and it distinguishes audio books from physical books, which like I think is worth pointing out, like David exclusively reads physical books over and over and over again. You could hear him in the podcast. So, books are powered by your attention. Like your energy is what moves the book forward. You could be dead and have an audio book in your ears, and it's the exact same thing, or doing the dishes or thinking about something else or scrolling your phone. Listening to an audio book is not the same as a book that like the page does not turn until you've processed the information, like ideally with a pen in your hand. But you inherently know, you're having like this internal dialogue with the information. You're powering the book. It demands more of you when you're reading than when you're listening.

David Senra: Let me ask you a question. So what other things, what other apps do you use after you use them, you're like, that was a good, that was time well spent? We agree, a good book, time well spent. Conversation with a friend, time well spent. Time with your lover, time with your family, time with your kids, time well spent. But I'm talking about fucking apps.

Eric Jorgenson: Readwise.

David Senra: Readwise.

Eric Jorgenson: The apps I use in the gym, like Whoop, Margins, which is like another reading app. Founders notes. ChatGPT.

Mitchell Baldridge: There's not much going on in your phone that's very fulfilling or improving your life.

Eric Jorgenson: I mean, shout out to portfolio company Portola. I genuinely really enjoy that one. It's super fun.

David Senra: What does that do?

Eric Jorgenson: It's like a character that is your best friend that lives in your phone that is powered by like these different LLM models and it learns about you and what's going on in your life and like you have dialogue with it and it helps you like, I don't know, it just is a very like fun and enjoyable experience that is like...

David Senra: So yeah, so we didn't name Twitter, we didn't name Instagram, we didn't name TikTok. Spotify, like you listen to music, feel good about that. You listen to an audio book, feel good about that. Listen to podcast, feel good about that. There is not many, especially when you get to like these huge platforms where they have hundreds of millions, if not billions of people on the platform. WhatsApp. I like WhatsApp. Like why? Because you're usually like you're talking to somebody you actually like, assuming you control it. I think some people use WhatsApp for work and then like people can send a message. No one could send me messages that I don't- so I guess I have more control over who has access to me than most people. But like yeah, I just pay attention. I guess my point here is like you could just dumb this down to the most like simple thing. It's just like how do I feel after this happened. How do I feel after I listened to that podcast, read that book, went on that walk, talked to that friend, and then just do more of that shit. And the reason you're not is because we're not being honest, like these things are addicting, just the same way like if you're a fat fuck and you like to eat potato chips. You don’t feel good after you eat the potato chips, but they have engineered you to keep eating the potato chips so just through the potato chips out. I think Naval hit it. If you’re going to use them as tools to promote your work, use them as tools to promote your work. Don't sit there reading that shit.

Mitchell Baldridge: Or YouTube shorts and the endless scroll. No one feels good by the end. It’s not great.

David Senra: Well, that's you. You send me these YouTube shorts. What I would do, what really helped figure this out, and again, if you're- I'm putting out shorts and TikToks and Instagram reels and everything else, but like they're all like 30 second lessons. Like I feel good. I'm like trying to- like I'll never combat like this just avalanche of bullshit coming on top of it, but like in my own little way, David and Goliath, I’m just like throwing rocks in there, a little bit in there, throwing a little bit in there. But like and some of them do really, really well. It's just like, hey, I like those reels. I watched them before I post them. This guy, Maxim, makes them. And I'm like, oh, I would watch this, boom. And I throw that out there. But the one thing that really hit me, it was like why I shouldn't be spending time on these apps is like you go through TikTok, and then like 10 minutes will pass by. Like, okay, you know what I'm going to do? Instead of flipping up like this, I'm going to go the opposite direction. I'm going to see what I just went through in five or ten minutes. Do the rewind, like go through and you're like, holy shit, I turned through 150 videos. Like, you'll remember where you were when you started. And you're like, this is so stupid. If you could play this back, if you could step outside of yourself, record what you're doing, why would you do this to yourself? And you're doing it because they've hacked your brain and it's very addicting. Like it may feel like shit, but it's really hard to get out of. So I just...

Mitchell Baldridge: It's literally hypnotic. Your eyes do the movement and your brain gets locked up.

David Senra: This is why I don't do cocaine.

Mitchell Baldridge: It works until it doesn't.

David Senra: No, because like, obviously, listen, like my dad was Cuban growing up in the 80s in Miami. It's like, what do you think he was doing? And like you see, and I've been around, I had a bunch of cokeheads in my family and everything else. And you're like, you see that behavior and like this... If you say, hey, put this in your body and then this happens, and you're not the one feeling the euphoria and sensation, like that seems like whatever you just did is not- I should avoid that. And the reason that it was, at some point, they thought... It was like the second... I read something one time where they're like, the most valuable product in the world is oil. And the second one is cocaine. And I don't know if it's still like this. It may have been like this when like Escobar was around or whatever, but the point being is like that euphoria, that it's like one of the most addicting things, and they were just like caught in this entire cycle of like, I must do this, even if I know it's bad for me. And like, I feel like when I get into- when I waste 20 minutes of my life on TikTok, it's like snorting a line or something. It's just like, this is not- it's so addicting. This is not good for me. The only thing, the only answer I have here is like complete avoidance.

Eric Jorgenson: Yeah, it's so much easier to not do something 100% of the time than do it only 1% of the time.

David Senra: Yeah, especially if you're an addictive personality... There's nothing in my life like, oh, just I do this once every two months. It's like no, if I like it, I'll do it every single day. Yeah, so I just have to run away from that. I do have a question though about like your collection of maxims and like new ones that you've come across, Eric, like how long have you been collecting maxims and then any new ones that you thought you wanted to talk about?

Eric Jorgenson: I fucking love a maximum. I mean, I think that's partly what drew me to Naval in the first place is like he is an extremely good like distiller. And I think you have the same sauce, the ability to get down to like four or five words that nobody has said before that encapsulate a complete idea that is memorable and applicable and useful. I mean, I'm constantly writing things down. I mean, I don't know if you noticed at Founders Only, when we're standing in a group together, I'm not trying to get in the conversation, I'm just listening. And when David says a maxim, I pull out my phone and write it down, or I pull out a notebook and write it down. So, I've been keeping these through listening to you, phone calls with you, podcasts with you for a very long time, because I can tell that they're accruing and that they evolve sometimes and that they might merge. But I think it's just a really- it is a useful thing for me to have personally. And I was like, once the list hit 75, I was like I should publish this. So, I just put it up on a blog post and tweeted it and LinkedIned it. And of course, obviously, it went viral because it's amazing content. But I think it's great. I mean, it’s great fodder for the book too, seeing which of these come up and how often and what are the supporting stories of them. I was thinking of Charlie Munger's Psychology of Human Misjudgment. He has this whole list of 30 things he's trying to impart and get you to remember, and each one has this little story that goes with it. And so, I think I'm just always listening for those and trying to remember and attach the stories.

David Senra: Have you read the unpublished David Ogilvie?

Eric Jorgenson: Yeah.

David Senra: I think, yeah, it's the book I give the most as a gift. I should have sent it to you if I didn't. But what I love about that is, for a long time, remember this like when like BuzzFeed or one of these like I guess AI slop before AI slop thing... they would post like listicles I guess, as they were called. Lists got a bad name, and I fucking love lists. Like David Ogilvie is one of the best writers I ever come across, and you see, the reason I asked for the unpublished David Ogilvie is because it was 50 years of internal memos and letters that you were- he was not writing for public consumption, and you just realize if you can distill down what you're trying to get across to somebody in a numbered list, it is actually a good way to get your idea into that person's brain... And I think I would like more landing pages if they were just like, here's 10 reasons why you should do whatever, like buy this product, use this demo, whatever. Like... my jujitsu school, like you go to the bathroom. And like, think about all the sanitary issues you have. You're like rolling around another guy. There's like you could get staff... there's like all kinds of bad shit that can happen. And like I should take a picture of it. It's like there's like 10 things that they want you to do and to maintain, just like essentially, they came up with 10 principles. We just adhere to these 10 things or I think it might even be eight. There's nothing else. Like you read it and it's immediately clear. You immediately know what you need to do. Yeah. I just think like I would- I think more people should use lists in their life. I was actually thinking about doing-

Mitchell Baldridge: The flight checklist. You’re about to take off.

David Senra: But I was thinking about one for life though. Like I've been really- I might test out doing something where, you know Bill Gurley's talk, Runnin’ Down a Dream, How to Survive and Thrive in a Career You Love? Like I want to distill- again, you have 400 books, 100,000 pages, that's down to 400 hours or 450 hours, whatever it is now. Could I get it down to like an hour? And I might even do this, not because like I want to do live shows, I actually don't. But I think like having like an hour long talk of distillate- like, it's a way for me to like, can I take what I've learned from this project and put it into like a 10 commandments. It doesn’t have to be 10, it can be whatever. But like, I do think it can't be like 50, can't be 75... And it's got to be personal to you. But I just like this idea of like, hey, these are the core bedrock of principles that I’m going to build my life and career on. Obviously, over time, take one out, add another one, but like you can't keep adding. It's not going to be 50 of these things. And I think doing it where, like one thing that's really helpful is you can learn something really well if you are forced to teach it to another person. So, it's like, okay, you're going to use this constraint of, hey, you have to give an hour-long talk in front of an audience. What would you want to say? Yeah, I don't know when I'll do it, but like it's definitely something that's like top of mind.

Mitchell Baldridge: It's the Tim Ferriss, you can have a billboard right in front of the- driving to the airport. What are you going to write on the billboard? That matters. And then yeah, how do you expand it from a billboard to a ten bullet point to an hour long talk to a book. I read this tweet a long time ago that says the checklist, life insurance, long-term disability, umbrella insurance, and the amount of people who said, look, I printed this out and put it on my refrigerator and marked it off until it was all done. And you're like, that's powerful. People just-

Eric Jorgenson: Put it in the book, put it in your book, Mitchell.

Mitchell Baldridge: It's in there...

David Senra: What is this collapse, collapse the gaps? Have we ever touched on that?

Eric Jorgenson: Well, I mean, that connects perfectly, actually, because I was going to say I think David Perell has a good maxim that is like, great CEOs are great sloganeers. And if you want something to like permeate through your culture, you need it to be like really tight, really memorable, and you need like your values or virtues that you want displayed throughout the organization to be quipable and memorable. And so, one of the things that I've, now that I'm like reading maxims and thinking in maxims, that I noticed I was solving problems well when I was collapsing the gaps in the organization. Like a problem would persist when the two people with the problem were abstracted away through some reason, whether it's inside and outside the organization or across two teams, or they just didn't happen to be in the same meeting within the like cycle of the problem. Or studying the famous founders of- like writing, working on this Elon book, and Elon has a tendency to just be like, yeah, sure, listen to the, whatever, report from the VP, but then go talk to the people on the line and be like, what is the problem in your own words? Tell me immediately. Go directly to the source for information. So, collapse the gaps is just my little maxim of get the people in the same room, get them on the phone, go directly to the source, skip whatever or whoever you need to and whatever amount of time, don't wait for the next cycle, don't wait for the next thing. Like if it's the most important thing, which if the CEO's attention is on it, it generally is. So, like collapse the gaps. And I'm trying to coach all my like executives to do that too.

Mitchell Baldridge: There was a guy, we were at a conference, and we were going to this kind of invite only dinner at the end of the conference. Yeah, big time. And I was talking to who I would call a high agency, $100 million exit guy. And he was like, what are you doing tonight? And I'm like, well, I'm going to this dinner. I wasn't hosting the dinner. I had no kind of like business to invite him to this. And he was like, who's running it? I was like, blank is running it. And he goes, oh, okay, good. And he just pulls out his phone and he just invites himself, and I mean there's something to that of like it may be obnoxious or it may be uncouth, but it also- like dude wanted to go. He knew that he would- he just said okay, I'm going to like move out all the bullshit in my way. So many people like- or I find myself doing this.

David Senra: And then a few minutes later, Mitchell gets a text that he's uninvited.

Mitchell Baldridge: Yeah, sorry, Mitchell. We ran out of- the dinner's over, but here's a Chick-fil-A gift card.

David Senra: Sorry, Mitchell, your spot was given away.

Mitchell Baldridge: Exactly, that’s it. That's exactly what happened. Yeah, and so I'm just fuming mad. Okay, I had to fly commercial on the way home. Yeah, so but then, yeah, just people wait for things to take two weeks that could just take two minutes. If you just picked up your phone and texted and said, what's going on with this?

Eric Jorgenson: The mantra of like, yeah, high agency, what would you do with 10x the agency, or just like, what does this look like without the bullshit? How do you remove-? Like, I've been thinking about it. The positive version of that is like doing elegant work. Like, how can you simplify whatever the task is in front of you and do whatever the highest odds of success thing is the fastest possible way and just like let the rest fall by the wayside unapologetically without carrying the baggage of like what it was like, quote unquote, supposed to be.

Mitchell Baldridge: This is where you're going to see AI. I mean, I don't want to text, I mean, David Senra is up at 2 am and he's working on the podcast, but I know he's busy. So, I don't want to text David. Like every time I have a thought, I'm not going to text David. I'm going to text Sage and ask Sage...

David Senra: No, no, no, this is not a future I want. I want relationships, so please don't...

Mitchell Baldridge: But this is where people are- But if if David's my employee, if I have an employee, I'm not going to text my employee at midnight. And this is where AI is going to collapse the gap is AI pretty damn good at reviewing your paid ad spin campaign and understanding what's happening out there, and you can just text it anytime you want. It becomes this kind of like intermediary for a lot of what's happening. It becomes the agent that... I was listening to Greg Eisenberg and Sam Parr talking about AI in the future, and they were literally talking about how it's immediately accessible all the time. And Sam goes, oh, wait, so it's cousin didn't die and it doesn't have to go to a funeral in Tampa? And you're like, you feel so bad as an employer to say that. But there's this drag of, it becomes complex, David, because like, yeah, relationships rule the world and relationships have friction. So how do you get the benefits of relationships without the friction?

David Senra: No, but we're not coworkers. Like, I'm saying text your friends. Yeah, of course. Like, if it has an advantage, man, listen, there's a reason why...

Mitchell Baldridge: When I'm thinking about you at 2am, I'm going to text you. Tonight, baby.

David Senra: You know my phone's on permanent DND.

Eric Jorgenson: Yeah, this is the only way to live in modern life.

David Senra: Permanent DND.

Books, Investing, LeverageEric JorgensonJune 24, 2025Podcast, Startups, AI, Book, WritingComment