Mark Cuban — How To Win When You’re Broke (Trailblazers Podcast Ep. 37)

Key claims

• His hardest challenges were being broke, then being a jerk. After Indiana University he followed friends to Dallas, bartended at night with five roommates in a three-bedroom apartment. Professionally, the bigger obstacle was his own “go go go” style until partner Todd Wagner told him in his mid-30s, “You’re a dick… people are afraid of you, and we don’t get as much done.” Learning to be kind got more done, faster.
• Stay in school, because college teaches you how to learn. He hates the trend of funding 18-year-old Stanford dropouts to manage 100 people. Go to a school you can afford, or community college first. With fewer people (especially men) going to college, he sees tuition starting to fall and scholarship money rising, and AI turns every student’s access into “the world’s best libraries, teachers, and professors.”
• AI is the great democratizer, and edtech is mostly a feature. Teachers should use free foundational models to personalize instruction and skip grading drudgery; foundation labs want students on their brand early, “like Coke versus Pepsi.” Anything built in Edtech “is going to be a feature not a product.” His framing: “Those who use AI so they don’t have to learn anything and those who use AI so they can possibly learn everything.”
• Curiosity can be learned, through maturity and self-awareness. “Find something you love to do and then put in the effort to be great at it because nobody quits anything they’re great at.” He claims nobody has succeeded in business without curiosity unless they got very lucky.
• Cost Plus Drugs works because it refuses to work inside the system. Launched January 19, 2022 with 111 medications; now thousands of medications, millions of people helped, sterile-injectable manufacturing, and a new Cost Plus Wellness (direct contracts between self-insured employers and hospitals, soft-launched in December). Every price shows cost, a flat 15% margin and $5 shipping. It is the only company he has put his name on, because rich people entering healthcare (the JPMorgan–Buffett–Amazon venture Haven) “always fail” by working inside the system.
• Trust equals transparency divided by self-interest. Showing cost and margin maximizes the numerator; a 15% margin minimizes the denominator. “That’s really what we sell is trust.” He would have Lina Khan break up the largest insurer, which he says has 2,600 subsidiaries and $160 billion in intercompany transfers.
• Raising money is an obligation, not an accomplishment. “I’m a billionaire because I didn’t give up a big chunk of my company”; he still owned a third of Broadcast.com at the sale. Wenger cites a Bryce Roberts study finding founders take home about the same at a seed-stage exit as at a Series D one because of Dilution. Founders “buy sales”: $5M in revenue, $30K in the bank and $60K monthly burn means you’re out of business.
• If he were 20, he’d take the $100K a month. Go to small businesses, automate their hassles with AI Agents at $100 an hour (no pay if it fails) and $25–50 a month to monitor model drift. Example: Rebel Cheese co-founder Kirsten built an agent that compares shipping invoices to the carrier price list and claws back tens of thousands of dollars in overcharges.
• Labor won’t go away, it will change. He cites Jevons Paradox and the gas station nobody foresaw when cars arrived; LLMs “don’t know when they’re wrong,” so he’s investing in world models, and he’d trust his mini Australian Shepherd over a camera-guided AI to cross a street. Lightning round: book over podcast, bootstrapping over VC, hire slow, moonshot over small wins, AI is “underhyped… the first inning of the first preseason game.”

Notable quotes

“If you already think you have all the personal skills you need at 16, 17, and 18, you’re going to be surprised how [__] up you are as an adult.” (09:23)

“The foundation to being successful is being curious. And not just being curious, but being able to be a sponge and… assimilate as much as possible.” (04:12)

“I’m a big believer there’s two types of people when it comes to AI. Those who use AI so they don’t have to learn anything and those who use AI so they can possibly learn everything.” (12:28)

“Because every time a rich guy comes into healthcare… they try to work inside the system.” (32:12)

“Trust equals transparency divided by self-interest.” (34:16, quoting someone he heard on a podcast)

“If you’re raising a ton of money, just remember, raising money is not an accomplishment. And it’s an obligation.” (37:22)

“Always whenever you can control your own destiny even if it’s slower even if it seems like you’re plodding.” (40:29)

“Look around. See that light, see that monitor… one day it didn’t exist. Then somebody had the idea to create that chair or that monitor… You have no idea who that person is. But why can’t that be you?” (51:57)

Chapters (from the episode description)

0:00 Intro · 1:25 Biggest professional challenge · 4:14 Should entrepreneurs go to school? · 7:26 How AI is impacting education · 14:26 Why women athletes make great CEOs · 15:40 Clavicular getting frame-mogged · 16:44 When to start a company · 20:59 AI slop · 26:08 The dark side of AI · 29:19 Fighting big pharma · 33:03 Rich people always fail in healthcare · 37:23 Business changes the world more than politics · 44:57 Advice for 20-year-olds · 53:46 Tech wars · 1:01:15 Rapid-fire questions

How it connects

• Mark Cuban: his person page; this episode adds his own account of his career, Cost Plus Drugs, and his AI-and-labor view.
• Cost Plus Drugs: the transparent-pricing pharmacy and its Cost Plus Wellness expansion.
• Bootstrapping, Dilution, Bryce Roberts: the case against raising money as an end in itself, and the seed-vs-Series-D founder-proceeds study.
• Jeff Bezos: Cuban borrows “your margin is my opportunity.”
• Trust, Transparency: his trust = transparency / self-interest formula.
• Curiosity, Education, Edtech: stay in school to learn how to learn; AI as personal tutor; edtech as feature, not product.
• AI, AI Agents, Future of Work, Automation, Jevons Paradox, World Models: the SMB-agent consulting playbook and his view that labor changes rather than disappears.
• Misinformation, Deepfakes: his bet that foundation models will reduce misinformation even as deepfakes of him proliferate.
• Populism: populism as a question of whom you trust to own the means of production.
• Atlas Shrugged: his half-remembered Galt’s Gulch analogy for communities that would reject AI.
• TBPN: where he first gave the “if I were 20” SMB-consulting answer.
• Healthcare: working outside the PBM and insurer system.

Transcript

From the YouTube auto-captions, lightly cleaned: obvious mis-transcriptions fixed (names, product names, URLs), [music] tags removed, and the four sponsor reads replaced with [Sponsor read omitted.]. The words are otherwise the captions’, including the speakers’ false starts, and the captions do not label speakers: each ”— ” marks a change of speaker, which the captions sometimes miss or misplace. Profanity is bleeped as [__] in the captions. Timestamps mark roughly one-minute blocks.

[00:00] If you already think you have all the personal skills you need at 16, 17, and 18, you’re going to be surprised how [__] up you are as an adult. If you want to be successful in business, you have to understand the foundation to being successful is being curious. The stereotype is go go go, keep up or get off the train. And if people don’t want to work with you or for you, that’s a problem.

— So, you’re saying stay in college.

— Yes, go to school. That’s where you learn how to learn. You may have a specific skill, whether it’s athletic, whether it’s technical, but if you don’t know what you don’t know, you’re going to have a hard time learning it. Whatever it is you were doing, if you’re mogging, who’s that dude Cleav? He’s like the king of mogging and he got out-mogged by some dude from Arizona State. But even if you want to be the ultimate look maxer, you are trying to improve.

— Today on the show, I am so excited to be joined by Mark Cuban. Mark is a well-respected investor and media personality. He made his fortune through early tech ventures, most notably selling Broadcast.com to Yahoo for 4.7 billion in 1999. He is also the former principal owner and now minority owner

[01:04] of the NBA’s Dallas Mavericks, which he led to their first championship in 2011, and was one of the longest-tenured sharks on ABC’s hit reality series Shark Tank. Mark remains one of the most influential voices in business and entrepreneurship online. Welcome, Mark.

— Glad to be here. So before we get into the meat of the interview, we like to start with an icebreaker. So I’d like to hear from you. What has been the hardest part of your journey so far? It can be professional. It could also be personal, but what is the first thing that comes to mind?

— I mean, it depends where in in my cycle, but being broke [laughter]

— was the hard part. When I first got started, I went to Indiana University and um got down to Dallas, followed a bunch of friends, and got a job at night working as a bartender and then working during the day. But I had five roommates in a three-bedroom apartment. And you know, I was still having fun, but when you’re broke, it’s motivated, but it’s not easy. And so, I think that was my greatest challenge. But professionally after that, after things started to roll, I think it was learning to read the room to be nice, you know, because I

[02:07] think growing up as an entrepreneur in, you know, in my 20s and early 30s, it was like go go go. you have to be that dominant, you know, entrepreneur that sets the tone, you know, expects nothing but the best, doesn’t suffer fools. And that held me back. It really, it took somebody, Todd Wagner, one of my um friends and partners, who said, “You’re a dick.” You know,

— at what age was that?

— I was in my 30s, mid30s. Yeah. And he was like, “You’re a jerk, right? People are afraid of you, and we don’t get as much done because people are afraid of you.” And I was like, “Oh [__] I thought I was nice, right? I got along with everybody.” And turns out, you know, my perception was different. And so adapting there and learning to be nice and kind to people made life a lot easier for me. But that was probably my biggest professional challenge.

— What made you get kinder? Was it just the realization? Is it something that you’ve had to foster? I mean, you come across as a pretty nice guy.

— Yeah. I mean, that was what changed.

— But like when you’re in business and you’re starting to get going, right? It’s new to you and all you know are the

[03:09] stereotypes that you’ve heard about and read about and seen and you know the stereotype was and is like go go go keep up or get off the train, right? And if you can’t hang, you know, you’re a soy boy or you’re this or you’re that, right? And um I it took a bit for me to adjust because I had to catch myself and but once I did life was easier because people were nicer to me which allowed me to get more done more quickly and and it turned out well.

— Yeah. That stuff compounds too. Like once you build a slightly better reputation then everyone kind of knows it.

— Yeah. And you know if if people don’t want to work with you or for you that’s a problem. You lose good talent. And you know, we it didn’t hurt us a lot, but it it slowed us down because somebody had, you know, somebody that I would communicate with would then go to somebody else and they would say, “Oh, don’t worry about Mark. He just goes full speed all the time, you know, or I’d send an email at two in the morning and wonder why somebody didn’t give back to me.” Just dumb [__] like that that to me, you know, I had no work life balance and I didn’t expect anybody else to have

[04:12] it either.

— So, this is one thing I’m seeing a lot. You know, I’m an investor, so I meet a lot of young founders, and those are a lot of who are getting funded these days,

— and it’s a lot of the like 18-year-old dropout from Stanford that’s super technical that now needs to manage a team of 100 people.

— Yeah, I hate that [__]

— Yeah. And my my question for you is like, how do we teach them to be good leaders? Because I think that

— tell them to go to college and stay in school.

— Okay. Yeah. Tell me your take on that because cuz ventures obsessed. I mean, I’ll be honest with you, I got a cold email from someone that was a 14-year-old wanting to raise venture capital, and I literally was like, “Please stay in school.”

— Yeah, for sure. Yeah. I mean, I’ I’ve had the same conversations. You know, my mom wants me to go to school this, whatever it may be. Um, and I’m like, yes, go to school. That’s where you learn how to learn. You know, you may have a specific skill, whether it’s athletic, whether it’s technical, whatever it may be. But if you don’t know what you don’t know, you’re going to have a hard time learning it. And if you don’t know how to learn, if you’re, you know, being successful, the foundation to being successful is being curious. and not just being curious, but being able to be a sponge and in, you know, and assimilate as much as

[05:14] possible. And college forces you to connect to people you otherwise would not to connect to, right? If you’re just in Silicon Valley and all you’re doing is talking to tech people and you’re walking around like a little tech zombie, you know, talking about your Clawbot agents and that’s all that’s the only context you have,

— right? Then you’re going to you’re going to lose out. You’re not going to know how to grow a company. You’re going to make mistakes that will cost you your company or somebody’s going to take advantage of you and acqui-hire you and you know everything you dreamed of won’t happen.

— [Sponsor read omitted.]

[06:16] So you I know you like sticky problems. We’ll get into all the healthcare stuff in a bit, but education is like the stickiest of problems. So you’re saying stay in college, get an education,

— but costs of tuition are only going up.

— That’s a place you could afford.

— Yeah. So what’s your take on that? Like is co is college still worth it? Do we need to rethink education entirely? Give me your take there.

— You know, do I think you need to go to an Ivy League school? No. But if you do, most of them pay for your tuition if you otherwise can’t afford it, right? Um should you go to a school you can afford? Yes. If you can’t afford school yet, should you go to a community college to learn the basics? Yes, because that grounds you and it it connects you um and it still challenges you. And if you’re able to breeze through it because you’re smart, then you breeze through it. You take your credits, but at least you’ve learned you’ve learned to set a schedule and stick to it. And you’ve learned, you know, different things you otherwise

[07:18] might not have connected to. Um and then, you know, you can transfer and still go to a school you can afford. But here’s the cool thing and I think that’s changing education one because so many people are concerned about AI and you know trying to get apprenticeships and more physical jobs you know um college um people going to college the number of people going to college is declining particularly among men and so I think you’re seeing tuition start to scrape down which is good you’re seeing um scholarship and support money start to increase which is good and then the third part of that is AI you know, because you can compliment I love, you know, people get afraid of AI for education. I love it, right? Because, [clears throat] you know, I I had to talk to in Pittsburgh where I grew up. I went and talked back went back and talked to a bunch of educators I think in um November

— and you know, there were teachers and they were all terrified like it’s going to take their jobs. I’m like, you don’t understand. AI allows you to personalize the education you’re offering to each individual student. You don’t need to

[08:21] spend all your time grading papers, the first pass, second pass, whatever. AI will do all of that for you and based off the progress that child is making. It’ll tailor what that student needs. And because of that, you can focus on things that just create the light in the kid’s eye. And then I said to them, isn’t that why you’re here? Right? Isn’t that what you want to do? To see that sparkle in a kid’s eye, whatever it may be. It may be art. It may be who knows what. It may be learning Polish because their grandmother’s Polish, you know, but that’s that’s the beauty of it. And so wherever you go, whatever you do, you have the world’s best libraries, teachers, and professors available at your fingertips if you just ask. And so, you know, while you can build um emotional skills, and you can build um relationship skills and other things, um you’re never going to be at a loss from the actual academic side. And so I think now there’s no better time now to want to go to college than now because if you know if you just don’t think that you if let me rephrase that. If you already

[09:23] think you have all the personal skills you need at 16 17 and 18 you’re going to be surprised how [] you up [] up you are as an adult. I mean

— I know

— you’re going to look back and wonder why you’re in your basement you know writing cloud bots and agents and making some money but afraid to walk outside.

— Yeah. But you know when you’re that age you don’t know better. It’s like you think you know everything.

— I have a 16-year-old son and trust me, he does know everything.

— And you think he’s like, I can’t possibly grow up beyond this, right?

— I don’t know if you have a take on this, but one of the reasons why I think a lot of educators are scared of AI and it’s not taking hold is actually there’s not a lot of products being funded. So like in general, venture capitalists have always been scared of edtech um and they haven’t funded it for like an extremely long time. Do you see that changing? What are the tools? Okay, tell me more. Tell me. So all the foundational large language models, the AIS, right? They know that if they get students, the younger the better using them, that becomes, you know, a brand that they become attached to,

— you know, like there’s discussions now, Claude versus, you know, ChatGPT versus Gemini, and they’re all battling

[10:26] for your attention. It’s like Coke versus Pepsi in a lot of respects.

— And so when there it’s basically free for schools, what edtech do you need? you just need to do it. I mean, how did you teach yourself about AI? You just dove in and and experimented, right? And tried things

— and it’s not like the AI gets mad at you. It’s not, you know, maybe you talk some dumb [__] like, you know, depending on how you set up.

— It’s pretty gentle, though, all things considered.

— Well, that’s a great idea, right? Um, but because of that, if teachers are just willing to put a little bit of time, it’ll save them a ton ton of time. It’ll allow them to be more flexible. So, okay, I’ll give you talking about um technology and education. Yeah. So, I went and last year, I forget when, went to Denver and got invited to talk to um a bunch of governors that were in there and they wanted to talk about AI.

— Wow.

— And I I don’t ever prof profess to be the AI guru, right? Because I’m not writing, you know, I’m not going to write a foundational model, any of that stuff. But at the same time, then at the last second, they threw me, well, how would you use it for education? And I’m like, I don’t know [__] about this. So,

[11:27] I’m waiting in the green room and I’m asking ChatGPT to list me the top 10 things that, you know, AI could do for education from K to 12.

— Yeah.

— And this [__] was good. It was really good. I was like, “Oh my goodness.” Right. And the point being that you can if you’re willing to take the time and teachers spend so much time trying to learn how to be better teachers, you know, all the, you know, what approach should I be taking now? what’s the latest approach to teaching math, reading, arithmetic, whatever it may be, you know, preparing kids for the standardized test, whatever they have to do. And [snorts] so, it’s not a stretch for them to try to experiment and learn these things. I don’t think you need big complicated AI because, you know, driven by edtech investments because, you know, that um I think that just takes it down the wrong direction. you know it it’s no no longer organic and more importantly anything you create in edtech is going to be a feature not a product at some point in time

— you know

— hence why a lot of people don’t invest

[12:28] in it because a lot of that’s been the past so far

— and that’s [clears throat] happening in everything software now where you know software was margin sell a whole lot of them price per seat now you see what’s happening to the software firms um public software companies and so

— outcome based pricing now

— right well or not even out um or usage based

— or token based

— token based tokens becoming kind of like the realm the currency of the realm. Right.

— Wild.

— Yeah. And so instead of price per se or you know x number of dollars per year, it’s how many tokens do you use and then you know what agent can you develop to arbitrage all the different tokens and five. So all these things are changing and where there’s change there’s so much opportunity and when you when an edtech investor puts money in there that’s the hammer and everything’s a nail,

— you know. And so I think there’s more opportunity to encourage teachers, professionals, whatever they may be, whatever your profession is, to just dive in and learn and and and figure it out. Because, you know, I’m a big believer there’s two types of people when it comes to AI. Those who use AI so they don’t have to

[13:31] learn anything and those who use AI so they can possibly learn everything.

— That was your viral tweet like a week ago,

— right? Yeah. Yeah. Yeah. I saw it. I got to put it in. [laughter] You got to sneak it. I think someone summarized they said the learners versus the lazy.

— Yeah. And it’s not necessarily lazy because we all try to take the path of least resistance,

— right?

— We all want the magic pill. We don’t want to do the hard work.

— Yeah. I mean, and because we only have so many hours in the day, this is our life and we’re trying to do the things we want to do to make our make ourselves happy, right? Um, but the the whole idea that, you know, AI is only going to make you lazier and think worse. I think that’s just a reflection of the person. You know, how how how do you encourage somebody to be curious? You know, you can rephrase the whole thing. There’s those who are curious and those who don’t give a [__]

— Do you think you can move from one bucket to the other?

— Yeah.

— Okay. Tell me about that because I think there’s some people like this is so random but when I was born my mom someone asked her what was an adjective to describe me and she said she was alert and I thought that was the funniest thing like what a weird

[14:33] adjective to describe me as alert for a baby like my eyes were like open still so alert I’m extremely alert I’m as curious as they get I mean even more than curious I’m like alert I’m on edge and I’ve always been that way and so I think it’s hard for me to gauge people going from you know a state of not being alert to being really alert and curious and wanting to learn. What’s your what’s your take there on like can we port them over and how do we port them over?

— It’s maturity.

— Okay.

— You get to different points in your life. You know, one day you’re the the homecoming queen and king or football star or cheerleader and the next day you realize once you get out of high school,

— no one cares.

— No one cares. Yeah. Right. And so what do you do? What direction can you take? and if you’re willing to learn and try things. But, you know, I just saw somebody talking about um women athletes make great CEOs because they’re driven and they understand how to set a schedule and they’re always trying to find ways to improve. And that’s so analogous to what happens in life and business. And that AI enables even further. If you have whatever it is what you were doing, it could be you’re

[15:35] trying to increase your bench press, you’re trying to do whatever, right? You’re mogging, you know, you’re, you know, all Who was that dude? Clavicle, whatever dude’s name was.

— Who? Who was this?

— Um,

— is it a sports thing?

— No, no, no, no, no, no, no. This is, um, a social media thing. Okay. Clav, Clavier, I forget. Clavicle, but he’s like the king of mogging and he got out-mogged by some dude from Arizona State and it was this big. But even if you want to be what is it? Look max, right? And be the ultimate look maxer. You are trying to improve.

— You’re like so Gen Z. You really got the slang down right now.

— I’m just, you know, like pay attention. Yeah.

— You have young kids. That’s why I have

— the best way to know what your kids are doing is to look at their Instagram and Tik Tok feeds. Yeah.

— But they’re like, “Get the hell away, Dad.”

— Yeah. It’s scary.

— It’s scary to them. Um, but in any event, um, you know, whatever it is that you’re trying to improve at, that’s the path. And once you get to that level of I don’t want to say maturity, but self-awareness, that’s a better way to do it. Once you get this level of self-awareness to say there’s a path I

[16:38] can take that I can learn to be smarter or better at something because people always ask me like you know when do I know to start a company or what should I do on that path right and I always say find something you love to do and then put in the effort to be great at it because nobody quits anything they’re great at and once you’re motivated and fired up and you’re making improvements you’re motivated fired up and making improvements right time flies you go down those rabbit holes I mean I’m sure it happens to do every day, right? You just go down, you start learning something. Well, that’s interesting. And what about this? What about this? And you start asking questions and it takes you into 20 different things. And the next thing you know, you’re having a conversation or looking at an investment and it relates, right? And it makes you smarter about what you’re doing. And that’s the beauty of all this. And that’s why you can learn to be curious. You can learn to, you know, im improve at pretty much anything. And if you suck at it, you take a step back and you find something else. But I think anybody is capable of it and it’s always the first step towards starting a business because there’s nobody in my mind that’s ever

[17:41] succeeded in business unless they got really lucky by not being curious.

— Totally. Well, one thing we are not talking about which is a factor of business is loneliness and connection. And I think some people can be really excited about an idea and really excited about their business, but if they’re building a loan in a basement, they can get really lonely and it’s hard. So, what’s your advice for someone who like maybe is very curious, but they have a remote job, you know, 5 days a week. They’re working really hard. They want to start something, but they’re kind of feeling like down in the dumps and depressed because they’re just talking to like their agents all day and they’re working siloed, but they don’t have human connection because that’s important.

— When I first started my first company, um, MicroSolutions, and I was teaching myself to code. Yeah.

— I remember starting a project, um, and I would do custom applications for people. Starting a project and looking up thinking I’d been doing it for two or three hours, and it was 24 hours later. Yeah,

— you know, and you just you start concentrating so hard and time flies. So, I get being stuck in the basement, right? Um,

— but the first step, you know, join a gym, join a club, do whatever, you know, I don’t care if it’s a walking club, you know, if you find yourself, you know, 5’8 and 300 lbs and you know, you’ve got

[18:44] to do something to deal with your health and deal with, you know, your just creating relationships. you you know you if you can if you can find the energy and the internal fortitude to take a chance and start that whatever business it is you’re doing in your basement you got to use that same will and fortitude to get out of the [__] house and even if you’re just walking around the neighborhood saying hi to people you’ll be shocked if you just go out where their people are

— even though you’re self-conscious look I’ll be when we leave I’ll show you a picture of me at 16

— okay

— all right so playing sports. I was on I got hit in the face um by a bike and I was running for ball. Da da da. And my parents, you know, my parents didn’t make much money and so I had to get caps on these two teeth. Okay.

— All they could afford were um stainless steel caps

— as in stainless steel colored caps. Like you had silver teeth in the front.

— I had Yes. Silver teeth. 16 years old. That’s brutal.

— Yeah. 16 years old. Every time I would smile, someone would go right.

— Yeah. Literally. Especially here with

[19:47] these lights.

— Right. They be like blinding me. Come on. You know, um I I weighed more then than I do now

— and was about five, six inches shorter

— and so it wasn’t like I was in demand, but um I tried sports. I, you know, had got a group of friends and hung out with them. They’re still my friends. And so you’ve got to go out there and put that same energy into, you know, creating a social path for yourself because, you know, you can you can go through Reddit, you can go through every platform that you ever wanted to to try to understand what’s happening in the world, but unless particularly now in an AI world, right? Because in an AI world where it’s so easy to connect to anything, then people are going to react to that and want to have IRL, you know, real world experiences. And if you want to be successful in business, you have to understand where people are willing to connect to AI and where they need real world experiences and real life communications and and connections. And one without the other, you’re going to

[20:50] fail.

— Absolutely. And and so much of I think we don’t talk about this enough, but so much of the stuff we see online is actually fake. It’s like created for ragebait. I had a very interesting discussion with someone at a dinner who’s like a deep research, deep fake um deep fake researcher and her we were all saying hot takes and she said, “I think you know my hot take is that we’ll never be able to know the difference that like so many of these models are being trained so good, right?”

— Yeah. On also like fake images and fake videos that we’re going to get to the point where it’s just all slop.

— Oh, some of the [__] I see that’s me.

— Yeah. And you’re like, “That’s really not me.”

— No. No. It’s like is that me?

— Oh, yeah. You don’t know.

— You don’t know, right? We could quote you saying something you never even said. No one would know

— multiple times, you know, and so

— um yeah, it’s it’s it’s going to be difficult. But that said, I think um the LLMs, the large language models, the AI will won’t deal with the the um deep fakes, but they’ll deal with misinformation better than anything we’ve gotten. I think there’s a lot of people out there that are trying to come

[21:51] up with algorithms that you can put in front of something that you look at and it’ll tell you if it’s misinformation or not. Nah, that’s that that’s going out of business. Um, what’ll work is large language models, it’s not in their interest to go down conspiracy theory rabbit holes without saying it’s a conspiracy theory. Because if you, you know, is a vaccine good? Should I get the MMR vaccine for my children? I’m a new mom. D, it’s going to say yes. It’s going to say there’s some people who think otherwise, but here’s the science. Yeah.

— Because it can’t not do that. Otherwise, it’s it loses all of its presence. It loses its independence. And so, I think all these foundational models are going to reduce the misinformation that we find out there. So there’s not, you know, now you’re starting to see in, you know, online magazines and even, you know, paper magaz or paper newspapers where there’s links to, you know, AI large language models that will allow you to summarize what’s already there and, you know, it’ll tell you the difference between an op-ed or columnist and a reporter in the facts. Now, it’s

[22:53] not going to always get it right, but for things that have science behind them, it probably will. [Sponsor read omitted.]

[24:58] Yeah. Well, that’s where I think also having like a community notes on Twitter or having some of these like gut check places and all these social media platforms is so essential. It’s like a mini version of that. It’s like because I mean I’ll even say for myself there was like sometimes there’s like a pop culture thing that’s like you know Katy Perry is pregnant with twins and it goes viral and then you’re like wait she isn’t actually pregnant with twins.

— So that’s where like a TMZ comes in or like a community comes in and I think that’s why everything

— latency to the to the takes a bit. It takes like an hour and then it’s already gone viral.

— Yeah. And then it’s gone. But at some point if you really, you know, for pop culture stuff, you know, what’s the cost? Who cares, right? [laughter] Um

— vaccines a little more important.

— Yeah. Yeah. The things that really really matter even though there’s a latency, you know, the biggest challenge is going to be whether or not um people who own intellectual property property silo it so that what they create is not trained. Yeah. On their

[26:00] stuff and they can get paid for it. That’s going to be the biggest challenge particularly for healthcare type stuff. So we’ll see what happens there.

— I mean there was that whole thing with Scarlett Johansson being the voice of the OpenAI chatbot. I don’t know if you saw that but crazy you know sometimes like these celebrities don’t even need to opt in because so much of their voices online you can do a lot of fake stuff without their consent.

— God the stuff like people using all the stuff I’ve said on Shark Tank and taking the videos. I mean it’s hysterical but it’s also like okay believe it.

— Yeah. This is Yeah. Trust me I know. I was Oh my god. I’m not even going to go there. Where people have put me. It’s crazy.

— What’s the craziest? You got to give us one.

— Porn.

— Oh, porn.

— Porn. Oh, I’m a stud. [laughter]

— Have you watched yourself in Mark? That’s crazy.

— No, I will not do that.

— You just see the screenshot of it.

— No, I had somebody No, I had somebody show me the start of it, right?

— I was going to say, Mark, the internet’s about to rip you for that.

— No. No. I’m like, there’s no way. There’s no way that’s real, right? And then someone sent it to me. I’m like, oh, [__] deleted it and sent the note to the platform and all that kind of stuff.

[27:01]

— Well, that’s where lawyers are helpful because you can send a little thing to

— Yeah. The lawyers don’t like those types of places don’t even care about lawyers. They just close down and show up as somewhere else.

— Yeah.

— Um like I actually work with the FTC, Lina Khan from the last administration, um who I love. And there’s a whole thing where um people were using all the images from Shark Tank and other celebrities as well and me independently to sell these diet pills, you know, and what what I was going to bring up, the crazy part is whenever the government would go and look at the website that was selling the these pills,

— Yeah.

— it would never be there. And I was like, “No, here it is.” And what these people, they’re so smart at what they’re doing. They would read for the source. um domain and if it had a.gov, they would change it to a website that was all flowers and pretty [__] and stuff like Yeah. It’s crazy.

— So smart.

— You got to respect the hustle.

— You got to respect the scammers and the hustle, right?

— I do. I I hate to say it, but sometimes I’m like, it’s so smart they deserve to win.

[28:01]

— I don’t want to say they deserve to win, but I give them credit for being smart.

— I give them credit. Yeah, for sure.

— Um Lina Khan, whether or not you agree with her politics, she’s so brilliant.

— She’s so brilliant. She’s been spending, you probably know this, but she’s been spending a lot of time in like the tech world, and she’s always at every conference I go to now.

— Oh, she is. That’s very cool.

— Yeah. She’s doing a lot of these like tech and policy panels, you know. Um, she has a little more free time now. Um, and she’s so brilliant.

— No, I love her. You know, we disagree on whether the big AI company should be broken up.

— Yes. I think she you probably as you and a lot of other capitalists disagree, but you know.

— Well, I’m a compassionate capitalist.

— Okay. Okay. That’s what you call it.

— Are you a capitalist?

— I’m a I’m a hardcore I’m a I like compassionate capitalist, but I think I’m more capitalist than compassionate. [laughter] I like making money. I like winning. We’re in a different Yeah. different place right now.

— Yeah. Yeah. That’s why sometimes when she says things, I’m just like, hm, do you know who you’re speaking to? This is a room of business people,

— right? And that’s okay, you know. Okay. Yeah. For her to stand up and say that. Um like

— But I respect it.

— Yeah. But I helped her with pharmacy stuff. We’re helping to, you know, when she was there to break that up. And that stuff I was telling you about with the the diet pills, I worked with her to try to to uncover it. We worked um her and

[29:06] Google um and to a certain extent Facebook to try to shut them down. and they didn’t get them all, but they got a chunk of them.

— Yeah, I could see her being on it. That’s That’s a good one for her. Um, speaking of drug pills, um, Cost Plus Drugs, let’s discuss. So, obviously made a big splash a few years ago when you started this. Um, I want to ask you like how is it going today?

— Killing it.

— Uh, give me the update. What’s going on right now?

— We launched um January 19th of 2022 with 111 medications and no clue whether or not we’d get any customers. And now we’ve helped millions of people. We’re in thousands of medications and we’re literally changing health care as we speak. We’ve expanded so that we’re manufacturing um these drugs called sterile injectables that hospitals use. Um we’ve created something called costpluswellness.com.

— Tell me about that too. Yeah.

— And so what that is is um insurance companies suck, right? Particularly the biggest insurance companies. And there are companies that do what’s called self-insuring where they pay for all the health care bills um rather than having rather than getting them insured

[30:08] directly. And um with Cost Plus Wellness, we let them do a direct contract. The company does a direct contract with the hospitals. And by doing that directly and cutting out the the insurance companies on those um on those transactions, it saves a boatload of money. And so that’s that’s brand new. We just soft launched it in December, I think, and it’s just starting to take off now.

— That’s so exciting.

— That’s really cool. Like literally,

— you’re tackling the market from so many different angles, too. You’re like insurance companies, okay? No, self-insures, okay, we just keep going.

— Just want to [__] up the whole thing. Nobody looks at their healthcare and says the economic side, that’s perfect. I love the way the system is set up. Everybody looks at the exact opposite way. And now we have all these big insurance companies that are trying to copy us and, you know, telling people, “Oh, wait. We do the same thing.” And they don’t. They’re not transparent. they they you know we’re still the only pharmacy that um lists all of its um the price of all of its medications. So, short story, you know, if you go to costplusdrugs.com, you put in the name of your medication or your grandmas or mom’s medications, right? If we carry it, um, it’ll [clears throat] come up

[31:09] and we’ll show you our actual cost. And not only we’ll show you our cost, we’ll show you our markup, um, our margin, which is always 15% and it’s mail order, so it’s $5 to ship it. And by doing that and limiting the margins and as our volumes go up, our costs go down, and passing that through, we’ve been able to save people. I mean, literally people will walk up to me on the street and hug me or start crying or send emails, you know. Um, my dad has cancer and he didn’t want to saddle us with credit card debt when he died and however long that would be. So, he decided not to take his medications anymore. But then we went to costplusdrugs.com and instead of being $93 that we can’t afford, it was $43 which we could afford. Life changing.

— Yeah. Just all the time. And it’s it’s it’s wrong that, you know, we’re able to do this because we should never be in this position in the first place. But, you know, these big insurance companies are so big, they’re too big to care. And so, you know, their margin is my opportunity to quote Jeff Bezos.

— Totally. Totally. There’s so many problems. I mean, I think it’s not even just with like Cost Plus Drugs. It’s these like PE firms that are coming in

[32:12] and gobbling up healthcare and trying to just suck them for what they’re worth and make a profit. Like there have to be some industries that we just protect that we just say like life-saving cancer drugs that’s got to be in the like let’s do 15%

— Lina Khan if you’re listening I think we should break up the big insurance companies. I’ll send this to her and then um they should devest all non- insurance assets because like the biggest insurance company has 2600 subsidiaries they do $ 160 billion dollar in intercompany transfers they they get to game the whole system they’re too big to care

— definition of a monopoly it’s huge It’s huge.

— It’s horrifying. Um, I think it’s amazing. The one thing I want to ask you too, so you put Mark Cuban Cost Plus Drugs on it and you’ve co-founded, invested in so many companies. To my knowledge, this is the only one that you put Mark Cuban.

— Yeah.

— Why did you do that? Talk to me about that.

— Because every time a rich guy comes into healthcare,

— they always fail.

— And why is that?

— Because they try to work inside the system. So literally um JP Morgan, Warren Buffett and Amazon got together

[33:14] created a company I think it was called Haven about five years ago where they said they were going to change healthcare within three years they were dust and here we are

— similar concept or what was the concept?

— The goal was the same. Yeah. The approach was completely different. Yeah. In their particular case they thought by creating the scale. Sorry about that. Um they thought by creating scale they can get better pricing. they can, you know, by using their own employees and their their customer base, they can get people to, but they worked inside the system. And I don’t work with the big PBMs. I don’t work with the big insurance companies. We worked to try to, you know, diminish them, right, and disintermediate them. And so I wanted people to understand that I was serious about this because it was my very first company I ever put my name on and that I was fully committed to doing this that you know when it’s all said and done on on my tombstone in 50 years if they say he [__] up healthcare and he had a good time I’ll be smiling.

— I love it. Well I also think the 15% margin thing is very tricky to accomplish and so people know that you have a lot of money so putting your name

[34:16] behind it too makes it more legit you know. I think that’s a big part of I mean, correct me if I’m wrong, but I think that’s a big part of it.

— Like one thing that I I heard in a podcast, some guy said, um, trust equals transparency divided by self-interest.

— And it applies to every business for anything, but particularly to healthcare. And by being completely transparent with our cost and margin, okay, that’s a transparency, high numerator. And by only having a 15% margin, okay, it’s not a ton of self-interest cuz nobody knows what anybody else charges, but they know that their prices are higher than ours. So, it must be more cuz we’re not big. People buy cheaper than us, you know, in a lot of cases, not all, but a lot of cases. And they must be marking it up a whole lot more. So, you know, that’s really what we sell is trust.

— [Sponsor read omitted.]

[36:21] I want to ask you, so I I heard you say this on TBPN that if you were um which is, you know, like a tech show we all love.

— Obviously, I did the show, right? So

— yeah, I know. You [laughter] know it.

[37:22] You know it. Um, and if you were, and I think they asked you like if you were a 20-year-old, your advice for a 20some, what would you do? And you said actually something that I thought was interesting. You talked about how, um, you’d almost like an AI, you know, coaching business for SMBs and build workflows for them, which is more of like an agency consulting model, whereas a lot of young founders now are going the like build a product, raise venture, blitz, scale, bull market. So, between those two, if you’re a 20-year-old, what are you picking? Are you picking the like making a h 100red grand a month with this consulting model going to SMBs or are you picking the like raise venture, take a big swing at fixing?

— I don’t know. I’m taking the money. I’m taking the $100,000 a month. Okay.

— And using that and just learning everything I could. So when the opportunity comes along, I can afford to do it myself.

— I’m a billionaire because I didn’t give up a big chunk of my company.

— When we sold, I still owned a third of it. If you’re raising a ton of money, just remember, raising money is not an accomplishment. And it’s an obligation

— and it’s dilution.

— Well, huge dilution, right? Particularly if you get caught in that trap of, okay, I’m going to do I did my

[38:24] seed, I did my angel, I did my seed, now I do my series A, then I’m going to go to a series B. And you think that’s the accomplishment? You’ve already failed. Like, I’ve seen huge multi-billion dollar exits where the original founder, I mean, it’s not nothing to make 10, 20, $30 million, but out of a multi-billion dollar exit to make $30 million.

— Yeah. It’s wild.

— Brutal. That means you’re working forever for somebody else.

— Totally. And why put in those extra five years? There’s um there was an interesting study actually my friend if I don’t know Bryce Roberts at Indie.vc. He’s amazing. And he put out a study that said on average founders make the same amount when they’re venture-backed if they have an exit at seed versus series D. And everyone’s like wait that doesn’t make any sense. Their company is worth so much more. No, they’ve been so diluted. It’s truly the same take on that.

— People don’t understand that. They don’t understand how it works. they just like. So entrepreneurs, even if you don’t raise money, we fall into the same trap. One, we all lie to ourselves. We’re better, cheaper, faster, whatever it may be. And that arrogance is a little bit good because it keeps you motivated. But then the other thing that we do, we get

[39:27] excited about revenue,

— not profits, revenue. Yep.

— Oh, I got to a million dollars. Like I I felt the same way when I was 24. I was on the Inc. 500. I got up to like number 29. and we were profitable but not as profitable as our topline number made it seem, you know, and um that’s where people fall prey a lot. Happens a lot on Shark Tank. Well, I got up to a million or five million in sales. How great is that? Are you profitable? No. And you know what? How much money do you have in the bank? You know, $30,000. What’s your burn? 60,000 a month. So, you’re out of business, but you got 5 million in sales. So, you bought sales.

— Yeah.

— You just can’t do that. And so you’ve got to understand what what really is important to stay in business. If you’re profitable, even it’s not if it’s not if out of that hundred,000 in revenue, it’s $5,000 a month and you’re barely hanging on, but that’s your baby, right? You own all of it. You make all the decisions. How many times have you seen a company where they got money from somebody and that somebody wanted, you know, some

[40:29] liquidity and started telling them you have to do A, B, or C so we can try to move out of this or you you you know or I’m not going to give you more money. And then the entrepreneur says, well, you told me to chase sales and now you’re telling me there’s no more money and now I’m going out of business because of you. always whenever you can control your own destiny even if it’s slower even if it seems like you’re plodding even if you know particularly if you’re in the valley or here in New York where everybody seems to be going faster and it’s going to get a thousand times worse in an AI world because everything is a feature as opposed to a product everything it’s just a question of how where and when it’s implemented and so going back to your original question on what they asked me on on on the show you know what I would do coming out of college

— I I would go to small medium-sized businesses having learned how to do agents, cloudbots, right? Anything and everything and say to them there is there have got to be a hundred things that you do in this tiny business that you don’t have the time to check the details on. You and you don’t know if

[41:33] it’s worth hiring somebody to do it. I’ll charge you a hundred bucks an hour and if it doesn’t work, you don’t pay. But I’ll save you time and money and you’ll find out if those vendors are ripping you off and undercharging you or underpaying you by $7 an invoice and you didn’t even know it or you know Sally who left you know two years ago told you about it but you haven’t got time. So what you’re able to do because a if you’re just graduating from college, you’ve already used AI to cheat for multiple years, right?

— Yeah.

— You’re paying attention to agents. You’re seeing what agents are and particularly if you’re in computer science, but you’re also facing a job um market where it’s basically 10% unemployment and computer science isn’t the end all beall that it used to be, but you learned Python, you learned, you learned all you learned how to do all these things. And so for you to walk into a business and just say, “Show me all the things that are a hassle that you can’t get to and I’m gonna see if we can automate them with agents and then I’ll charge you 2550 bucks a month to

[42:35] manage it or come in because there’s drift, right? If Claude changes something or Gemini in there.” Yeah.

— Yeah. Right. Or if they change something in their models, change their ways and all of a sudden what your agent used to do every day. Yeah. Like clockwork doesn’t do it anymore. Someone needs to monitor that. So, I’ll do that for you for 25 bucks a month. And I’ll give you the perfect example. So, one of my Shark Tank companies is a company called Rebel Cheese.

— And oh my god, I love Rebel Cheese.

— Is this the vegan cheese?

— Yes.

— Wait,

— Mark, I’m obsessed with Rebel Cheese.

— I knew I love

— I had it like a couple years ago um at my sister’s engagement party and it was the only vegan cheese I’ve ever liked in my whole life.

— Yes. Cuz they’re all vegans. I’m in a family of vegans. It’s so good.

— So good.

— Shout out Rebel Cheese.

— Yeah. Rebel Cheese.com.

— Yep. Go buy.

— So, Kirsten, the um one of the founders. Yeah.

— Um they ship a lot uh um to customers and when you ship um using UPS, DHO, whatever it may be, it’s always based off the package size and your source zone where you’re shipping from and what your destination is. And then there’s a

[43:37] price list effectively that when you put all this stuff into the system, it’s supposed to charge you the the function of of that those inputs.

— Yeah.

— Um but they don’t, right? they underpay all the time or over or I’m sorry, overcharge all the time. And so what Kirsten did was she put together an agent that took a picture of the price list, kept that up to date, took a picture of the invoice, you know, use CV on all this stuff, and then compared what it should be to what they were actually getting charged, and then created a credit to get the delta, and she’s making tens of thousands of dollars back from these shippers.

— Wow.

— Every company has got something similar. maybe not the details that they’re not looking closely

— because like you know in your business right and all the investments that you make

— you there’s you get home at night and you’re like I should be looking at this

— you know I

— always there’s all the num the little numbers and all the data yeah of course and so now so like when you did the research on me right and you put in the cloud and you’re like hey you know what’s right all that stuff right and it’s not always right obviously but at

[44:40] the same time

— th those are the opportunities because a small business and there’s millions particularly solo entrepreneurs that they just might have their own Etsy business or whatever and they might do, you know, $8,000 a month in revenue. But if you can help them, they’re your neighbor and you learn how to do these things, you can make thousands of dollars, you know, a week putting this stuff together because you can jump one day you work on this Etsy account, the next day you work on this, you know, shoe store, the next day, but you’re learning all this [__] in the meantime and you’re getting smarter and you’re keeping up with it. And then the next thing you know, you oh my god, I got this idea that can apply to all these companies that I’ve done. And you, you know, it’s going to be different then than it is or it was because to your point about entrepreneurs trying to raise money and then scale, what are you selling to scale?

— I know, right? It’s so custom.

— Yes. And so when you look at the foundational models, you know, or you look at the verticalized models like open evidence,

— that’s mass consumer, but it’s not a

[45:42] product per se. Mhm.

— You know, and going back in the day, like there used to be a bunch of web browsers. There used to be a bunch of search engines.

— Yeah. We forget that there was one winner. Yes. You know, so interesting.

— It makes what I think is fascinating right now is you’ve got all these foundational models, the Groks, the Geminis, the Claudes, etc. And we don’t know is it going to be like search engines?

— Yeah. We’re Google wins.

— We’re Google wins. Or is it going to be like streaming where there’s one big one or two big ones, Netflix and YouTube, and a couple people trying to, you know, glom on to content to get subscribers.

— You don’t know. So all those companies have got to play it as if it’s the search engine market and it’s winner take all. So you see them spending

— tons of money that they don’t even have, these big companies don’t even have. And so there’s going to be so much impact because those models have to keep on progressing forward and moving forward faster and faster and more capable and in weeks now I mean back in the dotcom era it would take at least a month or

[46:46] two for something to change. Now it’s like it seems like minutes everything is changing and it’s hard to keep up. But that changes how business happens. That changes how policy happens. When was the last time you saw AI as a service talked about by anybody in politics?

— It’s so sad. That’s what breaks my heart because you never It feels like we live in two different universes.

— But that’s the opportunity.

— Yeah, that’s true. And I feel like you kind of straddle that a little bit because you’re not afraid to talk to Lina or talk about Lina and they’re like so few people are scared of that. I love your comment about the search wars and the AI wars. What I will say is I think one thing that we don’t talk about enough is how well capitalized all the players are now. like back in the day and you know the numbers better than I but I look at like OpenAI and Anthropic raising these crazy rounds. I look at Gemini with Google behind them the behemoth like there’s there’s something

— and then you got Apple who’s not spending

— Apple who’s just sitting there like

— which I think is smart right and they now have the biggest market cap of all of them.

— We’ll see. We’ll see. I mean they have it’s like they such a head start with the phone. You know what I mean? I’m like you have the hardware in the pocket of every

— least resistance to get people

— least resistance. I I have a lot of thoughts on Apple but um it’ll be

[47:48] interesting to see how it plays out.

— Yeah, very interesting. Um, Mark, I don’t want to take up too much more of your time.

— Okay, this is fun. I’ll keep on going.

— This is fun. Um, okay. The last thing I wanted to say on this and then we’ll get to the lightning round is I think not enough people are talking about how yes, I agree with you on this consulting piece, but actually it’s pretty expensive to run these agents. So, I saw you tweeted this like in the past couple weeks how um and I think it was the All-In Guys maybe who posted about this where it’s like, “Yeah, maybe Jason.” It was like

— they’re actually spending they’re telling their developers to spend like, you know, whatever they want on agents and it’s actually adding up to like $300 a day.

— Yeah. more than you could hire somebody

— more than that which is $100,000 a year salary. And so there’s actually this really crazy question now of like are humans running the world? Are AI and humans running the world? Or is AI running the world? And I actually think like I have a lot of people I work with overseas who are like couldn’t be more brilliant and I pay a quarter of what I would pay if they lived in America. There’s so many times I do the math and I’m like I could build a custom agent for myself. I could use all the tokens I want. It’s almost always more expensive than hiring someone really smart that I

[48:51] train overseas.

— Except for your time.

— Except for my time, but I’ve I’ve outsourced. I’m like the queen of outsourcing.

— Yeah. Yeah. I try to do it all myself as much as I can.

— Yeah. Well, I I mean there’s some stuff I want to play with and

— No, I get it right. So, you learn, but you’re probably smarter than I am about it. You’re probably more efficient at it.

— I try to be I try to be because there’s a lot to do. So, like what’s your take on the future of labor? Like there’s this human, human, and a AI AI.

— Labor’s not going away. It’ll just be different.

— Okay.

— Right. There’s Oh, what’s Jevons’ law? Whatever.

— Yeah. Yeah. Yeah. paradox paradox whatever it is. Yeah. Where the cheaper something is, the more you use of it and the more opportunities like you know um when there were horse and buggies and the cars started to come along and people were upset. No one ever envisioned gas stations.

— It’s so far beyond what could be. Yeah.

— Right. So there’s going to be all kinds of stuff and

— yeah,

— you know, and even large language models now may be the I don’t know what a great analogy is. Um the old school may die out. Mhm.

— You know,

— who knows what’s next. Yeah.

— You know, because, you know, I’m making investments now in worldview

— because if you think about large language models, they don’t know when

[49:52] they’re wrong,

— right? They can’t tell you the consequences of their actions.

— Zero context.

— And so, a little baby, a three, a two-year-old baby on a high chair with a sippy cup knows that if they push it off the edge of the the high chair, mom’s going to come running.

— And then they learn not going to do that again,

— right? or or they learn to laugh and giggle [laughter]

— or they don’t learn for a bit.

— Right. Right. Um but they still might do it anyways, right? But they know the consequences. Yeah. And you can precode, you know, you can train it to say, well, if the kid push, but you don’t know if mom’s been working, you don’t know if mom’s mad, you can’t see mom and what she looks that little baby can. I’ve got a um mini um Australian Shepherd tucks. Those are smart ass dogs, right? I trust my mini Australian Shepherd to if I if I was blind to get me across the street at a four residential intersection than I would AI to get me across the street with a camera. And so the point being that yes, humans are going to be needed. AI is going to change again. We’re going

[50:55] to get into a worldview where you can get the law of physics and context, but there’s always going to be latency like we talked about before. There’s always going to be a challenge of um what’s next and what do you train on and then there’s going to be bigger challenges about what’s excluded. You’re trying to take vid videos for your worldview because you want to know this intersection and be able to train on it or whatever it may be. Um no, that’s my property. You can’t do that.

— Yeah.

— And so

— it’s so nuanced. It’s like the field of like ethics to me, you know, like so much of the stuff it’s like there is no answer. It is not black and white and we have to have these discussions.

— It never is. Yeah. It never is.

— No, but you’re right. I mean, it’s there’s a lot to learn, but I’m not afraid that, you know, oh, within two years, everybody’s going to lose their job. No.

— Right. Um because if that starts to happen, people are going to like, I ain’t [__] working with you. [snorts]

— Yeah.

— You know,

— yeah,

— we’ll go someplace where, you know, we’ll create um um Oh, in Atlas Shrugged, what was the place? Um in the valley. Anyways, um where they’re going to say, “No, we’re going to dis

[51:57] you know, before it was like the government telling them what to do in Iran, right? So, we’re going to we’re going to revolt and it’s going to be the same thing. We’re not going to let AI tell us to do. We’ll create this community and you’re not welcome. You know, if we need to, you know, use candles, we’ll use candles. Whatever it’ll be, but you know, it’s not going to be what people think it’s going to be.”

— Yeah. Yeah. I think we everyone needs to take a big sigh of relief and and view it with curiosity kind of to bring it full circle.

— It’s all going to change. And if you’re an entrepreneur, you may be able to change it. Like when I talk to kids, I always give the same speech, right? I always say, “Look around. See that light, see that monitor on one, see that chair, one day it didn’t exist.

— Then somebody had the idea to create that chair or that monitor.” And then they turned into a business. And here you are. You have no idea who that person is. But why can’t that be you?

— I love it. Everything around you is man-made.

— It’s very empowering.

— Exactly. Right. Yeah.

— And so I would tell them whenever you’re thinking of an idea or you’re thinking about a goal, just ask yourself why not me?

— Yeah. But the fear I think with software and I hear this a lot from my non-technical friends is you can’t see

[53:00] it, you can’t believe it, you can’t you can’t understand the intelligence capabilities and so there’s a big fear component to like I can see this chair and I can see this.

— That’s goes back to populism you were talking about, right? Because who do you trust?

— Yeah, that’s true. Do you trust the person who says, you know, I’m going to make it so that people that you don’t like or that you fear have taken things from you. I’m going to go after them. Or do you trust the person that says, I’m going to enable you and make your life better?

— You know,

— it’s who owns the means of production. You know, that’s where populism comes from. We forget it’s the government or the people. It’s your neighbors or it’s the government.

— And there’s place for government. Don’t get me wrong. I’m not like so hardcore libertarian. Yeah. You know, I want the government managing, you know, the flights and the roads and all that stuff. Infrastructure.

— Infrastructure. Yeah.

— Yeah. Yeah. That being privately managed sounds like a nightmare.

— [Sponsor read omitted.]

[54:03] Okay, we’re going to do quick lightning round. Sure. Okay, give me the first thing that comes to mind. Book in hand or podcast and ears?

— Book.

— Oh, any favorite books lately?

— Um, no, because I just read about healthcare these days. Okay.

— Because And I’ll tell you why. Because podcasts I get, you get wrapped up and you can’t stop, right? You can put a book down. I can’t put a podcast down.

— Yeah.

— Especially good ones. Especially this one.

— Exactly. Trailblazers for the win.

[55:06]

— Exactly. Exactly. Um, morning person or night owl?

— Um, both.

— Okay. So, that means just no sleep.

— Not a Um, actually I just changed my sleep a because I needed more. Um, but yeah, I didn’t sleep a lot.

— What’s What’s a lot? Give me What’s your average?

— I mean, it used to be four to five Wow hours. Now I’m back to 6 and 1/2 to 7 and 1/2 cuz I just decided like my workout sucked and I needed to

— get more energy.

— ChatGPT can tell you sleep more better.

— Yeah. Right.

— It’s your health coach now. Um cooking dinner or ordering in?

— Ordering in.

— Okay. Do you have a favorite spot

— or favorite cuisine?

— Yeah. I mean I I always there’s a place called Asia Mint in Dallas and I always order their teriyaki sea bass when they have it or salmon or scallops.

— Whoa.

— But I’m a sea bass guy. Yeah. I’m a sea bass freak. Yeah.

— Okay. Teriyaki seafood is interesting. I don’t have that often. Really?

— Oh my god. Like literally I was just in DC and there was this place that had sea bass with little teriyaki spices on it on a skewer.

— Oh.

— And I ordered it. I was there for two days. I ordered it for five meals. It

[56:08] was so good. After I tried it the first time.

— You’re a man who knows what he likes. Yes. Okay, I’ll give you that.

— Once I like this when I once I find something.

— I love it. I love it. Um VC or bootstrapping?

— Bootstrapping.

— Yeah. I feel like you’re the king of bootstrapping.

— Yeah, there’s no question about it.

— No question. networking dinner or big conference?

— Um, big conference.

— Yeah. Um, just because you can at least have some fun there. There’s more stuff going on and if you’re stuck in a networking dinner or whatever, everybody’s there to network and that’s just a pain in the ass.

— Yeah. And you might be seated next to someone, you’re like, “Okay, I’m done.

— Yeah, I’m done.

— I want to move around.”

— Exactly.

— Hire slow or fire fast?

— Um, hire slow and fire fast

— if you have to pick.

— Um, hire slow.

— Okay. And why hire slow?

— Because firing is painful. Mhm.

— I’d rather take as much time as I need to get it right. And I’m not very good at hiring. So, um,

— but yeah, I’d rather take my time because once you get them,

— it’s almost like you screwed up if you have to fire them.

— Yeah, I I’m sensing in the very beginning, we talked about you getting kinder as you got older. This hire slow answer is is showing me that you are really living that. That’s a kinder answer. You know, struggling to fire. I’m I’m I’m celebrating you that you’ve

[57:12] Yeah. Um, 10 small wins or one big moonshot.

— Moonshot. Okay. Being early or being right?

— Um being right.

— Okay. Why?

— Um because you’re right. Being early gives you a chance to be right on where others can’t be. Right. And I think that’s a positive. So I’m sorry. Um

— um but being early has always paid off for me because I, you know, you just got to figure out how to hold on till you’re right. Um but I’d rather be right at some level.

— Yeah. Never post on social media again to your 20 million followers, which we’ve clarified. Or I mean, this is kind of a hard, this is an easy one for you, but never fund raise another dollar again.

— Never fund raise another dollar.

— You have enough give enough money to have like FU money? You can do whatever you want now.

— Yeah, it’s very freeing.

— Very freeing. Okay, last question. Is AI overhyped or underhyped?

— Underhyped.

— Okay, give me your pitch. Why is it underhyped?

— Um, this is still the first inning of the first preseason game. We have no idea where it’s going to go. Um, but it’ll open doors that we can’t even envision right now. It it is the great democratizer of of education and

[58:18] information. Any kid that has access to a smartphone that can go to a web page can get access to the greatest minds ever and ask them anything and follow whatever that interest is. And to me, you could be in the poorest worst environment with the worst teachers at the worst schools, but if you’re willing to just, hey, ChatGPT, teach me how to do da da da da da and put together a study program that responds to the answers I got right and wrong. What can’t you learn?

— Absolutely. It’s that back to that quote you were saying earlier, right? Like if you want to use the AI models to learn everything versus learn nothing, right?

— Exactly right.

— Yeah, Mark, thanks for being here.

— This is fun. I really appreciate it. You crushed it. It was a lot of fun.

— Thanks so much for listening to the Trailblazers podcast. If you found this conversation valuable, please follow along on socials, share with a friend, leave a review, all the things. Most of all, please subscribe to our channel. It helps more contrarian builders find us and supports the work we’re doing here. To learn more

[59:19] about what we’re doing, you can visit trailblazerspod.com or my venture capital firm, parkrangerscap.com, or just follow along on socials at Erica_Wenger. Until next time, keep trailblazing.