Habits and Hustle - Episode 483: Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns

Episode Date: September 12, 2025

Listen to the full episode: https://www.youtube.com/watch?v=ThY-UBFtGK8  What if I told you Mark Cuban has invested over $100 million in companies from complete strangers who just sent him an email? In this Fitness Friday episode, I'm sharing insights from my conversation with Mark Cuban about his unconventional investment approach and the incredible companies built from cold outreach. We discuss how Cuban manages 200+ investments with just 12 team members, why he answers every single email personally, and the remarkable stories behind two of his biggest wins: a $4 billion space company and a revolutionary pharmacy that's disrupting Big Pharma. Mark Cuban is a billionaire entrepreneur, owner of the Dallas Mavericks, and star investor on Shark Tank who has built his reputation on being accessible to anyone with a compelling business idea. What we discuss: The $750K Investment That Became Worth "A Whole Lot of Money" at $4B Valuation Why Cuban Reads Every Email and Deletes Most in Under 2 Seconds How He Manages 200 Companies with Only 12 Employees The Cold Email Strategy That Led to Cost Plus Drugs Revolution Behind the Scenes of Shark Tank: Why 75% of His Deals Actually Close The Real Reason Most Shark Tank Entrepreneurs "Ghost" Their Deals How Cuban Turns Alyssa's Cookies Into a $20M Business With Zero Advertising Why He Refuses Meetings But Responds to Strangers' Emails Within Minutes The One Question Every Entrepreneur Must Ask: "Why Didn't I Think of That?" Thank you to our sponsor: Therasage: Head over to therasage.com and use code Be Bold for 15% off  Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www.magicmind.com/jen and use code Jen at checkout. 99designs by Vista: 99designs.com/jen20  – click "Claim my discount" to get $20 off your first design contest.  Momentous: Shop this link and use code Jen for 20% off  Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order Find more from Mark Cuban: Instagram: https://www.instagram.com/mcuban/  Find more from Jen: Website: https://www.jennifercohen.com/ Instagram: @therealjencohen Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagements

Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it. Hey, friends, you're listening to Fitness Friday on the Habits and Hustle podcast, where myself and my friends share quick and very actionable advice for you becoming your healthiest self. So stay tuned and let me know how you leveled up. Before we dive into today's episode, I first want to thank our sponsor, Therisage. Their trite panel has become my favorite biohacking thing for healing my body. It's a portable red light panel that I simply cannot live without. I literally bring it with me everywhere I go. And I personally use their red light therapy to help reduce inflammations and places in my body where, honestly, I have pain. You can use it on a sore back.

stomach cramps, shoulder, ankle. Red light therapy is my go-to. Plus, it also has amazing anti-aging benefits, including reducing signs of fine lines and wrinkles on your face, which I also use it for. I personally use Therisage Trilite everywhere at all the time. It's small, it's affordable, it's portable, and it's really effective. Head over to Therisage.com right now and use code. Be Bold for 15% off. This code will work sitewide. Again, head over to Therisage, T-H-E-R-A-S-A-G-E.com, and use code be bold for 15% off any of their products. How many people actually work for you in your organization? Just in dealing with the shark tank and other deals, probably 12. That's all. Yeah. Oh, that's it. Yeah, yeah. You have one,

this is like a side note, Alyssa's cookies or oatmeal. Yeah, Alyssa's healthy's cookies. Oh my God, I'm obsessed with those things. So am I every morning for breakfast, no exceptions. They are delicious. You can't get them on the West Coast. Yeah, you can. You can get them at Ralph's, I think. No. No? Trust me. I've checked because I found them in Florida at the Super Bowl two years ago, and I became obsessed with them and you can only get them at like public safe way and I on the website

it was a whole schmaidre so I never ended up ordering them but I called them a bunch I was wondering when they're going to be here because they are so delicious because no because I know because one of my deal parts with Shark Tank is they got to have

Alyssa's there during the day for me to munch on so they're here so I'll find out for you I'll find out for you but you got to hear the story about yeah this guy Doug sent me an email saying basically he was living out of his car

and broke and he sent me samples of these cookies. And the first thing I always do it when anybody sends me any food is I look at the nutritional information. Right. You know, because if it's all fat, sugar, whatever, I'm not going to be interested. Right. So it's just huge cookie.

And I turn it over. It's 190 calories for enormous cooking. That's not bad. Then I look, it's like no added sugar. I'm like, that's good. All this fiber, you know, huge amount of fiber, like a whole day's worth of fiber. And then protein. Yep.

I'm like, okay, let's see how this thing tastes. So I break off a little piece. I'm like, this is good. I'm like, what's wrong with it? So then I go to pull the cookie out of the wrapping and it falls apart. And I'm like, ah, that's the problem. Because when people go to buy a cookie, they want to eat a cookie. Right.

So I made them change it to healthy bites because the way their whole manufacturing process works, it's really easy to combine it with a little bit of moisture and put it together. So it tastes moist, right? And they're just these little bites and they stay together. Put eight into a package. And with eight of them, it's only three. 360 calories, right? So I eat, yeah, so 45 eat. So I eat like all eight of them for breakfast. Oh, that's what I did. You can't just eat four or two. No, no. And it's only 360 calories for

breakfast. And I'm getting my fiber. I'm getting, you know, it's like eating healthy cereal, only it tastes better. It's delicious. And you don't, and you feel like you're actually giving, like you don't feel like you're depriving yourself with it. Yeah. That's what I felt like, I feel like. But I, this is like two years ago or three years with COVID. I can't remember. Everything like blends. But I haven't looked for the. last probably a year. But I did, I was like obsessive over them. We got to find you where they are up here because I know they are. And I order them either from Amazon or from, I guess I could yeah, and from right from the website, Alyssa's Healthy Cookies website. I should just do that too.

Are they doing well? Oh, Russian. So this guy, this guy went from living out of his car and helping him get started. I mean, I went to Central Market in Dallas and did one tasting thing. Yeah. And then it just blew up from there. Really? And that was more than 10 years ago. Now, they'll do just under $20 million in revenue, but that's not even the good part. We spend no money on advertising, not a nickel.

Right. Not a penny. Yeah. Nobody knew what they were when I was telling them. Yeah. But people go in there and buy them, but people who buy them keep on buying them over and over and over again. And we'll make $10 million in profits. That is amazing.

So this guy went from living out of his car to like being Mr. Badass down in Florida making millions of dollars a year. That's incredible. You know, it's funny that you say that because for the super, it was for like Max and Super Bowl party and the whole stuff, like everybody who was doing it, everyone became obsessed with these things. And we would buy, we would, we would like clean the shelf of every single place. I go in there and I buy like six at a time, eight at a time, wherever I'm traveling.

Easily. For sure. I mean, Alyssa's healthy cookies and now we have a vegan version and we've got a chocolate Yeah. They're all really, really, really good. And like, if you got a little bit of time, you throw them in the microwave and they get really like smushy, yeah, soft. They're great. They're great. And they've got a little travel packs. I take them in the row with me and my little computer bag and back to back. Yeah, so I can travel with them and I always have something healthy. Okay, we've got to find out about this West Coast thing because that doesn't, yeah, because that doesn't

make sense. You must love, what's with you and oats though with mush? Mush. Yeah. Yeah. And do you just love oats? Is that? No, it's not that at all. I like things. that are tasty and healthy. Yeah, it's true. You know, and, you know, Ashley, the female entrepreneur behind it is just insane. I mean, she's just, yeah, she's a force of nature. So when you get companies like that and the entrepreneurs are amazing and the product's amazing and it's healthy, yeah, why not? Totally. What's the one thing you look for when you do an investment with a startup? Is it the people or is it the product? Product first, because you can have great people, but if it's not going to sell, it's not going to work. But, you know, I look to say,

is this something where I say to myself, why didn't I think of that? Yeah. That's the first thing. And then even if it's not quite that, I'm like, okay, you know, if I'm looking to buy it or typical consumer or company is looking to buy, is this something that's going to be compelling, differentiated, easy to buy? And if it passed those tests, then I look at the entrepreneur and say, okay, can these people do it? Yeah.

Well, you know, I find it interesting. I always stare at you when I watch this show because I feel like you're very decisive. That's not the answer I wanted after you said that. Oh, yeah. Well, maybe I see her brother this too, but this is like an ad, you know, a family show. But what would, why is it that like, I feel like it's my, maybe it's just my opinion. But like, you're like so decisive that you like could, either you like someone I feel or you don't like them. Like you know pretty quickly.

Well, remember, there's a lot of editing that goes on. I know, that's what I'm saying. Is it just because of the editing? Yeah, it's because of the editing. Because how long is each pitch, really, in real life? Stupid ones, 20 to 30 minutes. Oh, wow. Intense ones, 90 minutes to 2 hours.

medium ones, an hour. Oh, so that's why, because there's so much longer. It's our money, and we know nothing about them when they walk into the room. They're not vetted at all. They're vetted by producers, but not by us. So we know nothing about them. Here comes Jan. They'll say, this is Jen, and that's it.

So it really is a surprise when people walk in. Yeah, no idea whatsoever. So then what happens, like, well, then you guys do due diligence, right? After we say yes to a deal, we can do due diligence. So what's the ratio or how much with percentage? of things that go through. So early on, for me, it was about 75%, but now we get more and more people who just come on for the commercial.

Yeah. And so they'll say, oh, great, we got a deal. And then they'll ghost it. They do. They do, yeah. Because I've had a few people come on here or I've met in, like, real life, whatever. And, like, they said that they went on and it was not you, actually. No.

Other people, other sharks. Wouldn't close the deal. Wouldn't close the deal. And it just like made. Or try to change it. It dragged on and dragged on. Yeah, that's not me. Yeah.

Some of the other ones will do that where they'll, like, try to change the deal. change the deal terms and this and that. And that's up to them, right? However they want to do it. But if I agree to it, I'll agree to it. But if you drag me out, then you're playing with fire. Yeah. Because either you want to do a deal and you agree to what you agree to or not. Yeah. And who's your favorite shark besides, you know. I like Barbara, the work with the best. Yeah, I like her too. Because we compliment each other because she's really, she looks at people first and I look at deal first or product service first. And so we compliment each other really well. Right. So do you do most of the deals you do with her, though? If I can, yeah, if I can, yeah.

How about those other two? We'll move off of this, but, like, I'm so fascinated by this show. Like, how about the Mr. Wonderful? Yeah, he's okay, but Kevin doesn't do a lot of deals. Nothing. And he also waste people's time. Yeah, that's just a schick, right? Yeah, but he's a great guy.

So, yeah, he's a really good guy. He's not like he is on TV. Oh, he's not? No, he's a really good guy. The other one seems very nice, Rob. Robert's too nice, you know. Yeah. But he's a good guy, too.

Lori does a good job. You know, Lori is all about her wheelhouse, things that she can just plug in and sell QVC or whatever, she's going to be great at. Right. So then I want to ask you back with, because when you were a kid, obviously, you were selling the baseball cards and the garbage bags and, like, stamped, everything for those basketball shoes that your dad didn't want to get you. Yep.

Like, you were like a born hustler. Like, you just were. Without question. Without question. So were you like the guy, like, if I went to school with you, would I be like, oh, that guy's for sure going to be a billionaire? That guy's for sure going to be successful. No, no, no.

You probably didn't even know who I was. You'd be cute, and I'd be a little fat guy. I don't know. I don't know if I'd be the cute one back then I either. Yeah, like when I was 16, no, when I was 15, 14, 14, freshman in high school, I was playing baseball and I ran into a bicycle. And my parents, like, my dad did upholstering in cars, didn't have a whole lot. And like, rather than getting me caps, because I broke two teeth running into a bicycle. And rather than getting me caps that matched on my other teeth, they got me stainless steel caps so that, because they were last longer, they were cheaper. No way.

And so every time I smiled, even like in my high school graduation picture, there would be these two teeth at the bottom that were still colored. Really? Yeah. I mean, and like if I showed you my 16-year-old picture, I was like 5-8, 5-9, weigh 30 pounds more than I do now. Really? Can I see a picture? Do you have one? Let me see.

That is, I would never have guessed it. Because you seem super... Yeah, things change. No kidding. Things definitely... Yes, $4.7 billion later, things definitely change. But like, you seem very all... I mean, I don't know you.

That's picture me at 16. Oh, my God. No, it isn't. Yep. This does not even look like you. That's me at 16. Wow. Wow.

I don't even know what to say. The teeth are gone. Like, you got them fixed. No, no, no. No, no. You just can't see it there. No, I'm saying. right now, you got them fixed after you kind of like got out of this whole face. That's

insane. So like you showing everybody, it's pretty amazing actually. I would never, but also that's one handsome motherfucker. I was going to say, the truth is like at the time, if you saw some pictures of me when I was 15, 16, it's mortifying. You know what exactly? Thank you. You don't be so, you know, dramatic there. But like the point is that still, like you were not know, like you seem to have like a confidence, though, a self-confidence. Where did it come from to even do all these deals and wheeling and dealing? I mean, there's two different things, right? Like being confident about around girls when you're 16. And then being in business. Like in business, you can just do the work. Right. You know, I just, you do the work. So,

you pick whatever topic. And if I need to learn it for business for whatever reason, I can just spend the time. Yeah. And it's just up to me. You know, it's like the saying, you know, the one thing in life you can control is your effort. And so that's just my style. I mean, you know, I learned early, early on that most people didn't. Yeah. You know, and whether it's learning how to code, whether it's learning about business, whether reading this book or watching that video, you can figure shit out. Yeah. Most people don't do it. And so that's what gave me confidence because I knew I do, I do the work. I'm prepared. And that set me apart, always. So you're just like you love,

I read this a bazillion times, and I know if you've said this, like you just, love to learn. You read a ton, like four hours a day. Curiosity is one of the greatest business skills anybody can have. And once you're curious and you find something that's interesting to you, particularly if it fits what you're trying to accomplish, then it's just a matter of taking the time to learn it. Right. Let me share my daily routine game changer with you. It's the Momentus 3. I've been using their protein, their creatine, and Omega 3 combo for months now. And the results are undeniable.

These nutrients are key for long-term health and performance, but hard to get enough of through diet alone. The CREA pure creatine boosts both physical and your mental performance. The grass-fed weight tastes great with no weird aftertaste, and the omega-3 is a must for recovery. Since adding these, my energy, my recovery, and my overall well-being has really improved. So if you want better performance, this is the way to go. Visit livemomentus.com and use my code, Jen, for 35% off your first subscription.

That's livemomentis.com code gen for 35% off your first subscription. Trust me, you'll be happy you did. were you always just very interested in like computers and not computers necessarily yeah my software what do you call it like just yeah all the above right technology and um it wasn't until when i got to dallas um i got a job working for a software store and i had to learn it all right there and then on my own and and that's really what got me into it i found out that because you know i didn't mind reading software manuals hardware manuals whatever right that um that gave me an edge and I could sell so you combine the two together and I was taught myself out of program and

you know I did really well as a salesperson selling software until I got fired you know and then I started my own company in the rest of history well also like you're very self-reliant like you don't like mentors you never had a mentor right no never nope what's your reason for like do like when people have asked you that before you're like no I don't believe in them it's not that I don't believe in them to each their own but it's just like you just going through the process of figuring things out is a skill. Yeah. Learning how to understand a market or a company or a product or service is a skill. Right. And, you know, there really aren't shortcuts. And I get, you know, having a mentor to

introduce you to people and all that kind of stuff. But, you know, those same people will introduce you just as a referral if you have a great product or service and you're good at what you do. Right. And that's the way I always looked at it. And like, so like what do you do? Because you're in the situation now where everybody wants you to be their mentor or something from you, you know? Yeah, I get that all the time. All the time, right? Like, did you say fuck off? Do you, did you say that? Does it work? Does it work? Because especially the 16 year old kids, you know? Yeah, exactly, right? No, I mean, it just depends on the circumstances. Like, typically what I'll do is, um, just say, you know, send me an email. Yeah. And if it's a question, I can answer, I will. And as long as they

don't ask me 50 questions, you know, as long as they don't ask me things that are easily answered just by searching online, you know, then I'll try to help them. Because sometimes, I mean, it's crazy even like probably what I would have done, like 12, 13 year old kids that'll email me with business questions, you know, though it's very, you can tell it's very self-serving, you know, or you'll get parents emailing me for their kids. And so they do what they say. Yeah, it's just like, oh, my son or daughter is really interested in ABC, can you answer these questions? I'm like, no, I'm not going to answer them for you. Now, if your son or daughter took the initiative, Right. What's insane not to go too far after. Like now I'll get emails from parents of adults,

you know, 22, 24, 28 years old, you know, asking for job advice for their kids or will I reason. I'm like, hell no, you know. Is that crazy? The Coddle culture we have now? Yeah, I don't know if it's culture per se or just like these parents that are just like, a lot of them. Yeah, helicopter parents to the 9,000th degree. Absolutely. And I'm like, no. No, you know, and I just won't respond. How do you get your information? Like, you're so accessible, though.

Yeah, my email's public. Like, so I'm going to say, like, every, how do you not have, like, aren't you just in and it all day? I know you have 10 phones you carry around. Well, no, I got two. Yeah, well, three I have, yeah. Just in case I need bed or service or I can be working on one and whatever, talking on them.

But in any event, like, you know how you can just set a preview mode? Yeah. So I just read the preview. And if it's interesting, I read it. And if it's not, I hit the delete key. It takes me two seconds. You must be doing that all day, though. Yeah, you know, it doesn't matter if I'm eating lunch or doing whatever, you know.

And it's, you know, me time where I can just bang through them. And there's always something interesting there. And I've literally gotten emails where I've invested probably over $100 million from people I don't know. And a lot of, there's one company that I invested, I don't know how many millions now. And they're out here in L.A. And they're begging me to come visit because I've never met the guy, relativity space. And that's what it's called? Yeah, relativity space.

What do they do? 3D printing for space rockets for rockets. Oh, my gosh. Yeah, and it's enormous. And, you know, I think their last valuation was $4 billion, which made my stuff worth like a whole lot of money. No kidding. Because it was just these guys from Dallas who were told me about, you know, they want

to use 3D printing to build rockets. I'm like, that's really cool. I asked some questions, did some homework. They answered all the questions great and everything. And so I gave them like 75, 750 grand for 20% or 25% of the company. Now, I've been diluted significantly since they've raised a bunch. but and you know even as I put in more um but yeah it's worth you know enough to cover all my bad investments that is amazing and you never met them yeah with the cost plus drugs um dr oshmian school

that was a cold email i was going to tell the story that is crazy the guy just called like just emailed yeah just emailed me um guy named dr o'smiansky who is a radiologist um practicing radiologist also has a phd and math and statistics also did one year of law school just for the of it. I mean, just insanely smart. Everything comes easy to him intellectually. And he sends me an email. It was a subject line. I don't even remember. But it was basically saying that he wanted to create a compounding pharmacy to make generic drugs that are often out of supply, right? And because they're out of supply, the people who make them can charge anything they want. Because if you happen to have that disease that needs it, you're going to do it all you can to forget it. And I'm like,

well, that's pretty cool, but that's too short-sighted. We've got to do it for all generics. Right. And so this was going on four years ago. We started what turned out to be a company called costplusdrugs.com. And I kind of massaged the whole business plan and invested. And basically, we have built this company. If you go to costplusdrugs.com, we tell you exactly what our cost is for any drug we sell. We just added 113 more today. So now we're close. closing it on a thousand different skews. Today alone, because yesterday you added a bunch of... No, we reduced prices yesterday.

Oh, those are the... Okay. And added a bunch today. And so, you know, just the fact you're reducing prices on drugs at all is insane, right? People are... That's a real problem. No, it's a huge problem, right? That's why we did this. And so now if you go to cost plus drugs.com and you put in a monotab, which is for people with leukemia, as I found out. And you can see that our cost is $45, and we sell it for...

$48 and we sell it for $54, right? You'll see our cost, we add 15%. That's it. It's $3 for the pharmacy handling fee and $5 for shipping. That's like a game changer. That is a disruptor. It's changing a lot of things. You know, it's crazy some things that we didn't even expect to see. Somebody, because they see our costs, let alone our pricing, now they're able to back in to a lot of the bidding that goes on for different insurance companies. And somebody does, did some research that said if for just 77 of our drugs buying a basic quantities, if Medicare bought from us instead of where they buy now, it would say $3.6 billion a year. And that's just $77 drugs.

And, you know, now we've got more than $900. So you can see where it's going. But, you know, in this country in 2022, we should never be in a position where you have to choose between your rent, your food, and your medication. Yeah. And we've been able to change that. And, you know, we thought we were going to primarily deal with people without insurance. But as it turns out, not only were people without insurance really benefiting and saving a ton of money, but people with insurance, we're more often than not cheaper than people's co-pays. Yeah. That's what I was going to say you could have co-pays a loan or so high. Yeah. So, I mean, you might have a $25 co-pay. Yeah. You know, and if any of our, you're buying a drug that costs less than $25, you're saving money. That is, well, actually, the other thing is like you have to hit a minimum. So for me, I don't even bother. I have to just pay out of pocket until I hit a place where it's so expensive that like this even like it doesn't even matter where you are socioeconomically. It's so helpful. Yep. So you check us out, cost plus drugs.com. Just go in there, look for the medication or your parents or your aunts, your uncles, your grandparents,

whatever. And if we have it, we will save you money guaranteed. That's amazing. So like even like something like a good R.R.X, right? That was that, you know, that crushed and all these other ones are coming in. Good or X is great. But any of the coupon companies, what they do is they work with. in the system. Right. And so you'll see like the Walmart's two, you know, two miles away is a different price than the Walmart's one mile away. Right. And CVS is, you know, because they've different price. And then if you go, yeah, and if you go back two weeks later, it's completely different price. Yeah. And so with ours, it's just the same price. Right. No matter what. Now, you can't just go pick it up because we, we mail it to you, right? But it'll show up in three

to seven days and you can order, you know, whatever quantity you want. And the more, the bigger the quantity, as long as your doctor prescribes it, the lower the price you'll pay. So guys out there that want, you know, generic Seattleus, I mean, it's like 18 cents a tablet where it was, you know, who knows how much otherwise. So how do you, like, how are you guys, like, what's your projection? Like by next year, are you going to have how many drugs and like what's available? We hope to have over, you know, close to 2000 by year end. And, you know, and there's other things like methoxy, I forget which drug it is,

that, you know, is really an issue right now because of Roe versus Wade being over. return. Yes. You know, birth control. So our pricing, you know, both are generic, and so our pricing is so much lower so people can buy, you know, birth control far less expensively than they could before. This drug that has a lot of different uses, but because one of them is for, could potentially cause a medical abortion, there's a lot of pharmacists who won't sell it now, particularly in southern states. So we'll sell all that stuff. You know, as long as it's prescribable and we can carry it, we'll sell it. That is, and I went last night and I looked around.

Like, it's also very simple. Yeah, it's really easy. Yeah, just put it in. Yeah, so, you know, if you're buying birth control, you just put in whatever brand you use and we'll show you the generic version. And you can, you know, buy it, you know, what did I just say? I was talking to somebody. The recount 48, you know, for $25 or whatever is like just insanely low versus.

And also, I saw there's a button there where it's like, well, if you don't have a drug. I can say, okay, I'm looking for... Yeah, just sign up and tell us what you're looking for. Yeah, and then what's the problem? Can you guys, like, if you get enough requests, are you guys people? We try to. Yeah, we try to. We're trying to add everything, but it's just good to know if we, you know, if we get a ton of people asking for one specific drug, then we'll prioritize that first. Now, is that your major thing right now that you're super excited for, yeah, that's like, that's like, that's super exciting for. That is more than game changing. Like, I mean, when I heard, when I initially heard about it, I was like, I was, I didn't even believe it because I thought it was too good to be true.

That's what a lot of people say. What's the catch? You know, we don't sell your information. You don't have to pay a monthly fee. None of that stuff. Yeah, it's amazing. You don't need a card. It's just straight up. You know, we take our cost plus 15 percent. And then we just hope we sell enough to cover all our costs. And did I, is it true that you guys now have already surpass what you thought you were going to be? Yeah. I mean, we're way past what we thought we'd be two years in. That's amazing. Yeah, it's incredible. So no wonder you're like all in on that one. Thank you.