Mark Cuban on Entrepreneurship, DEI, and the Future of Healthcare

the person who controls the algorithm controls the world right and if you are committed to one specific platform as

your singular source of information or Affiliated platforms then whoever controls the algorithm or the

programming there controls you the following is a conversation with Mark cubin a multi-billionaire

businessman investor and star of the series Shark Tank longtime principal owner of the Dallas Mavericks and is

someone who is unafraid to get into frequent battles on X most recently over topics of Dei wokeism gender and

identity politics with the likes of Elon Musk and Jordan Peterson this is Alex Freedman podcast to support it please

check out our sponsors in the description and now dear friends here's Mark

cubin you've started many businesses invested in many businesses heard a lot of pitches privately and on Shark Tank

so you're the perfect person to ask what makes a great entrepreneur somebody who's curious they

want to keep on learning because business is ever changing it's never static um somebody who's agile because

as you learn new things and the environment around you changes you have to be able to adapt and make the changes

um and somebody who can sell because no business has ever survived without sales and as an entrepreneur who's creating in

a company whatever your product or service is if that's not the most important thing and you're just dying

and and excited to tell people about it then you're not going to succeed but it's also a skill thing how do you sell

what do you mean by selling selling is just helping I've always looked at it about putting myself in the shoes of

another person and asking a simple question can I help this person can my product help them from the time I was 12

years old selling garbage bags door too and just asking a simple question do you use garbage bags do you need garbage

bags well let me save you some time I'll bring them to your house and drop them off to you know streaming um why do we

need streaming when we have TV and radio well you can't get access to your TV and radio everywhere you go so we kind of

break down Geographic and physical barriers and you know Cost Plus drugs you know what's the product that we

actually sell we sell trust um in a simplistic approach we buy drugs and sell drugs but we add transparency to it

and bringing transparency to an industry is is a differentiation and it helps people trust in an industry that's

highly lacking in trust exactly okay so what's what's the trick to selling garbage bags let's go back there 12

years old what I mean is it just your natural Charisma I guess a good question to ask are you born with it or can you

develop it oh you can definitely develop it yeah I mean because selling garbage bags door to door was easy right because

like 12-year-old Mark going hi my name is Mark do you use garbage bags you know what the answer is going to be right can

I just drop them off for you you know once a week whenever you need them you just call and I'll bring him down sure

so that was easy but I'm sure you've been rejected oh yeah of course not everybody says yes what's your what was

your percentage I don't remember but it's pretty close to 100% oh okay never so that's why you don't remember yeah

right because who's going to say no to a 12-year-old kid who's going to save them time and money but you know typically my

career where I've started companies it's to do something that other people aren't doing whether it was connecting PCS and

to local area networks and at micro Solutions and you know the salesmanship was walking into a company and just

saying look talk to me and I can help you improve your productivity and your profitability is that important to you

and the answer is obviously always yes and then the question is can I do the job and can I do it cost effectively and

so you didn't have to be a born salesperson to be able to ask those questions but you have to be able to be

willing to put in the time to learn that business and that's the hardest part I'm sure there's a skill thing to it too in

like how you solve the puzz of communicating with a person and convincing them yeah I mean there's

skill from the perspective that I read like a maniac then like now you can give me an example of any type of business

and it'll take me two seconds to figure out how they make money and how I can make them more um productive and I think

that's probably my biggest skill being able to just drill down to what the actual need is if any and then you know

from there being able to say well if this is what this company does and this is what their goal is how can I

introduce something new that they haven't seen before and is that a business that I can create and make

money from so figure out how this kind of business makes money in the present and then figure out is there a way to

make more money in the future by introducing a totally new kind of thing correct and you can just do that with

anything pretty much yeah and you think you're born with that no I worked at it because you know going back to what I

said earlier about curiosity you have to be insanely curious because the world is always changing my dad used to say we

don't live in the world we were born into you know which is absolutely true if you're not a voracious consumer of

information then you're not going to be able to keep up and no matter what your sales skills or ability are they're

going to be useless what did you learn about life from your dad you mentioned your dad my dad did upholstery on cars

you know got up went to work every morning at 7:00 came back 5 or 6 7:00 exhausted and I learned to be nice I

learned to be caring I learned to be accepting just you know qualities that I think he really tried to pass on to

myself and my two younger brothers were just be a good human you know and I think you know he didn't have business

experience so as I got into business he would just you know say sorry Mark I can't help you you know I don't

understand what you're doing you never went neither one of my parents had gone to college um you've got to figure it

out for yourself but he was also very insistent that um he you know he worked at a company called Regency products

where they did upholstery on cars and he would bring me there to sweep the floors not because he wanted me to learn that

business because he wanted me to learn how backbreaking that work was I mean he lost an eye in an accident at work um a

staple broke um and he the only thing he wanted from my brothers and I was for us to never have to work like that to go to

college to figure it out you said to be nice that said you also said that you when you were first starting a business

you were a bit more of an asshole than you wish you would have been absolutely yeah yeah because I was more of a yeller

I was you know I no really yeah what you see on the sidelines you know with me at a Mavs

game maybe a little bit but I also didn't have any patience for somebody I thought wasn't using my kind of common

sense right because I was always on the go go go go go when I particularly when I was younger just trying to be

successful trying to get to the point where I had Independence and I would tell this to people you know either

you're speeding up and getting on the train or you know we'll stop and drop you off at the next station but let's go

where you go did you have trouble with the higher fast Fire fast part of running a business yeah always cuz I

hated firing people because it meant one it was an admission of a mistake in the hiring and two the salesperson of me

always wanted to come out ahead and I was always horrible at firing but I always partnered with people who had no

problem with it so I always delegated that well this a tricky thing when you when you're working with somebody and

they're not quite there and you have to decide are they going to step up and grow into the person that that's the

right or they're not and in that grayer area is probably where you have to fire was hard yeah for sure because you know

there it's obviously a failure somewhere in the process you know what did we do wrong and when I would interview people

for jobs I mean 99% of the people I've ever interviewed I've wanted to hire because

in my mind it was like okay I can figure out how to make this person work right and and then they wouldn't and then you

know people at the company be like Mark you suck at this you know and so I I always delegated to hiring yeah I mean

I'm the same I see the potential of people I see the beauty in people and which is which is a great way to live

life but when you're running a company is a different thing it's different and you got to know what you're good at what

you're bad at right I I was good at you know I was a ready fire aim guy and I always partnered with people who were

very anal and perfectionist because where I could just go go go go go go they would keep me in keep me inside the

baselines they would do the due diligence I supp or just yeah the detail work to dot the eyes and the cross the

tees uh what does it take to take that First Leap into starting a business that's the hardest part it really

depends on your personal circumstances like I got fired I mean I was sleeping on the floor six guys in a three-bedroom

apartment so I couldn't go any lower so there was no downside yeah there was no downside for me starting a

business and it was just like you know I was 25 when we started micro Solutions and you know I just gotten fired and it

was like look I'm I'm a lousy employee um I'm going to just start going to some of my prospects that I had in my my job

and asked them to front the money that I needed to install some software and found this company architectural

lighting who put up $500 for me that allowed me to buy software and have 50% margins and you know that's how I

started my company but like by way of advice would you say I mean it's a terrifying thing yeah I mean you've got

to be in a position where you're confident you know I get emails and by people all the time you know what kind

of business should I start that tells me you're not ready to start a business right either you're prepared and you

know it or you don't you know in in the United States with the American dream everybody kind

of always looks at themselves and say okay you know I have this idea right and then you go through this process of

saying okay you know you talk to your friends or family what do you think and then almost always oh it's a great idea

right then you go on Google and you say oh my God no one else is doing it without thinking you know 10 companies

had gone out of business trying the same thing but okay it's on Google and then people stop right because that next step

means okay I have to change what I'm doing in my life and that's not easy for 99% of the people some people look at

that as an opportunity get excited about it some people get terrified because it's okay maybe I'm comfortable maybe I

have responsibilities and so whatever your circumstances are if you want to take

that next step you have to be able to deal with the consequences of changing your circumstances and that's the first

thing you know do you save money you know so you have you know if you have a job do you have a mortgage do you have a

family you got to save money you can't just walk you know I mean they've got to eat and they've got to have shelter but

on the other side of the coin if you've got nothing it's the perfect time to start a business yeah desperation is a

good Catalyst for starting a business but in many cases the decision as you're talking about you're going to have to

make is to leave a job that's providing some degree of comfort already so and I suppose when you're sleeping on the

floor and there's six guys it's a little bit easier it's really easy right particularly when you get fired and you

don't have a job you know and you're looking at bartending at night to try to pay the bills and so um it wasn't hard

for me but to your point it it really comes down to preparation you know if it's important enough to you you'll save

the money you'll give up you know whatever it is you need to give up to put the money aside um if you have

obligations um you'll put in the work to learn as much as you can about that industry so that when you start your

business you're prepared and you can always you know at night on weekends whenever you find time lunch start

making the calls to find out if people will write you a check you know or transfer you money to buy whatever it is

you're selling and by doing those things you can put yourself in a position to succeed it's where people just think

okay you know gono I'm leaving off the edge of a cliff and I'm starting a business that's tough but sometimes

that's like the way you do it though there's always examples of any situation or scenario right right but I mean

anecdotal evidence for everything yeah but if you're if you're going into a new business you're going to have

competition unless you're really really really really really lucky and that competition is not going to just say

okay let Lex or Mark just kick her ass yeah and so you've got to be prepared to how you're going to deal with that

competition what what do you think that is about America that has so many people who have that dream and act on

that dream of starting a business you know I think we've just got a culture of consumption

and more you know and to get more um you've got to you know creating a business gives you the greatest

potential upside and the greatest leverage on your time um but it also creates the most risk so that capitalist

machine there's a lot of elements by contrast uh the respect for the law like an entrepreneur can trust that if they

pull it off the law will protect them they won't hopefully that's still the case Yeah

well yeah there's always uh yeah USS other countries you're right right so US versus other countries like Joe Biden of

all people said to me um it was at an entrepreneurship conference that when he was vice president he had put together

and we had gone up there from bunch of us from Shark Tank to talk to young entrepreneurs from around the world and

he said to me Mark you know the one thing that separate I've been to every country around the world and the one

thing that separates us is entrepreneurship we're the the most entrepreneurial country in the world and

there's no one else who's even close and when you look at the origin of our big you know the biggest companies in the

world for the most part there's an American origin story somewhere behind there and I think you know that just

gets perpetuated on itself we see those Horatio Al aler stories we see um examples of the Jeff Bezos of the world

the Steve Jobs in the world and those are the types of people we we want to copy yeah want to be really careful and

try to really figure out what that is because we don't want to lose that for sure we want to protect that whatever

you know and that's a lot of the discussions about what's the right way to do government big government small

government what's the right policies what but also culture like who we celebrate one of the things that

troubles me is that we don't enough celebrate the uh the entrepreneurs that take risks and the entrepreneurs that

succeed it seems like success especially when it comes with wealth is uh immediately matched with distrust and

criticism and all that kind ofu yeah it's changing for sure because you know you can go back just 12 years right

traditional media dominated let's say to through 2012 you know that was the peak of linear television you know newspapers

weren't as strong but they still had some some breath and depth to them um and then social media comes along and

everybody gets to play in their own sand boox and share opinions with people who think just like them and that and it

also gives them the opportunity to amplify um those feelings and I think that's where celebrating entrepreneurs

really started to subside some there were always people who were Progressive that were like billionaires are bad or

millionaires are bad depending on the time period but you didn't really see it on an ongoing basis right it wasn't

going to be on the Evening News it wasn't going to be in the front page of the newspaper um it was going to be if

you read a book and someone talked about it or you read a magazine and there was an article

um talking about you know this Progressive Movement or that Progressive move whatever it may be um you know and

then or political parties but now all of that is front and center on social media yeah we're trying to figure

out how we deal with the with the mobs of people and the virality of it all and um I I think we'll find our footing and

start celebrating greatness again well that I mean that's the whole reason I do shark tank that's true that's that show

celebrates the entrepreneur it's the only place where every single minute of every single episode we you know we

celebrate the American dream and the reason I do it is we tell the entire country and it's shown around the world

even we you know we're we're amazing advertising for the American dream in I don't even know how many countries but

every time somebody walks onto that carpet from debuk Iowa or Ketchum Idaho you know that sends a message to every

kid who's watching Seven 8 nine 10 12 year-old kid that if they can do it from catch Idaho you can do it if they can

have this idea and get a deal or even present to the Sharks and have all of America see it you can do it and that I

mean I'm proud of that um the 15 years of that is just it it's just been insane you know now kids walk up to me and go

yeah I started watching you when I was five or 10 and I started a business because I learned about it from Shark

Tank and so you know I think you know we're being C it celebrates it and we convey it and I don't think it's going

away but there are different battles we have to fight to support it yeah I love even when the business idea is obviously

horrible just just just the guts to step up to be there to believe in yourself to really reach I mean that's what matters

I mean cuz like some of the best business ideas are probably uh maybe even you and Shark

Tank will laugh at oh for sure you know without question the good ones we're not going to recognize every good one and

then sometimes we'll just motivate people to work even harder to get it done because of what we say to them and

and that's fine too you know there's been great success stories that we said no to what stands out as like a

memorable business on uh you've been pitched on Shark Tank what what's the best one that stands out there's no best

one right they're all different um they're all best in their own way I guess they're stupid ones and you

know we haven't had any you know World Earth world changing Earth shattering ones right because

those aren't going to apply to Shark Tank they don't need us right you know so we typically get businesses that need

some help at some level or another um but there's ones I've passed that I wish like spike ball do you know what spike

ball is so it's just rebounding net that you can put on the beach and you have these yellow balls and you play a game

of you know it's just a competitive game but they're killing it so if you go to beaches in New York or La you'll see

kids playing it all the time and it was a fun game um that I wish I had done a deal with there's and there's been

others and you passed and I passed they they were getting some traction and they wanted to create leagues spikeball

leagues and they wanted me to be the commissioner and I don't want to be a commissioner of a new spikeball league

so you have to kind of have this gut feeling of will this scale will this click with people of course yeah can it

be protected is it differentiated is it something that makes me think you know why didn't I think of that um or is it

just a good um solid business that's going to pay a return to the the founder and may not be enough of a business to

return to um an investor yeah and I guess the question you're trying to see will this scale This Promise will the

promise materialize into a big thing we see I don't even care if it's going to be a big thing right it because it's all

relative to the entrepreneur we had a 19-year-old from Pittsburgh Laney who came on with the simple sugar scrub and

there was nothing outrageously special about it I didn't see it becoming a hundred million doll business I thought

it could be come a two three5 million business that paid the bills for her and that that was good enough and you know 6

months after um the show aired she called me up she goes Mark I've got a million dollars in the bank what am I

going to do I'm like enjoy it put aside money for your taxes and go back to work you know and so it doesn't have to be a

huge business it's just got to be one that makes the entrepreneur happy but then there's the valuation piece I mean

right do do a lot of the entrepreneurs overvalue of course business yeah I mean that's that's the nature of it right I

mean and that that's really where the biggest conflicts in Shark Tank happen that's in valuation they you know they

they think this is the best business ever you know there we had one lady um couple that came on and they had this

scraper for cat's tongues right nice bizarre most one of the most bizarre pitch ever I love it um you know and

they had this insane valuation and it was on because it was corny and fun TV not because it was a good business oh

really okay you didn't see the potential none yeah none there's a lot of cats in the wmart yes there are and they'll go

do very well without me so how do you determine the value of a business whether it's on Shark Tank or just in

general it's actually really easy right so if you take just to use an example a business that's valued at $1

million and I want to buy 10% of that company um for $100,000 then in order for me to get my

money back they've got to be able to generate a $100,000 in after tax cash flow that they're able to

distribute can they do it or can they not right and if it's $2 million Valu whatever the valuation is that's how

much cash after tax cash they have to generate to return that money to investors or the other option is do they

you know do I see this as business potentially having an exit right do they have some unique technology or do they

have um something specific about them that some other company would want to acquire then the cash flow isn't as as

um not I don't want to say important but isn't going to guide the valuation and how do you know if a company's going to

be uh acquired so it's the technology like the patents but also the team is it yeah it could be any of the above right

it could be it could be a a super Products company that um I think is going to take off and how do you know if

they can generate the money what's what's the you made it sound easy you know yeah I mean is can the person sell

you know and if not them can I do it or someone on my team do it for them so you're looking at the person yeah for

sure yeah that where Barbara corin's the best she can look at a person and hear them talk for 20 minutes and know can

that person do the job and do the work can you tell if they're full of shit or not so one of the things with

entrepreneurs they're kind of like we said overvaluing so they're maybe overselling themselves but also they

might be full of shit in terms of their understanding of the market or also like or exaggerating what they're thinking to

do all that kind of stuff can you see through that y for sure just by asking questions you know so if if they are um

delusional at some level or misleading at another level I'm going to I'm going to call them on it you know so you get

people trying to sell supplements that come on there and it's a cure for cancer or whatever it may be or there's this

latest fad that you know increases your core strength without doing any exercises you know shit like that I'm

just GNA bounce I'm gonna pound on them right see I still love that I still love the trying just you know give them

credit right because they know all of America is going to see it and they're deluded themselves to believe this story

so strongly I mean there's a delusional aspect to entrepreneurship right like you just I I see that that's a great

question um do you have to be ambitious and you know set aside reality at some level to think that you can create a

company that could be worth 10 100 a billion dollars right um yeah at some level because you don't know it's all

uncertainty but I think if you're delusional that works against you um you because everything's grounded in reality

you've got to execute you've got to produce you know you can have a vision right and you can say this is where I

want to get to and that's my mission or this is my driving principle but you still got to execute on the business

plan and that that's where most people fail yeah you have to be kind of two- brained I guess you have to be able to

dip into reality when you're thinking about like the specifics of the product how to design things how to like the you

know the first principles the basics of how to build the thing how much it's going to cause all that yeah I mean

because if you can't do the basics you're not going to be able to do the bigger things and at the same time

you've got to be one of the things that entrepreneurs do that I I always try to remind any that I work with on is we all

tend to lie to ourselves our product is bigger faster cheaper this or that as if that is a um finite situation that's

never going to change right and there's always somebody I call them Leap Frog businesses there's whoever's competing

against you you know if you do a or C they're going to try to do c d and e right and you better be prepared for

that to come because otherwise they're out of business too so you're never in a vacuum you're always competing against

sometimes an unlimited number of entrepreneurs that you don't even know exist who are trying to kick your ass

and the tricky part of all this too is you might need to frequently pivot especially in the beginning hopefully

not so you think like in the beginning the product you have should be the thing that carries you a long time yeah

because I mean that's that's your riskiest point in time right and so if you've done your homework which includes

going out there and testing product Market fit um you should have confidence that you're going to be able to sell it

now if you didn't do your homework and you go out there and you sell whatever it is then and you've raised money or

whatever just to Pivot you've already shown that you haven't been able to read the market and so it's not that pivots

can't work and always don't work they can but more often than not they don't you pivot for a reason that's because

you made a huge mistake well also mean like the the micro pivots which is like iterative development of a thing oh yeah

that's not yeah just iterations yeah you know entrepreneurship being having any business is just continuous interation

continuous your product your sales pits your advertising you know introducing new technology how do you use AI or not

use AI where do you use it what person is the right person there's there's just a million touch points you know that

you're always re-evaluating in real time that you have to be agile and adapt and change but especially in

software it feels like business model can evolve really quickly too like how you going to make money on this with

software for sure because you know anything digital because it can change in a millisecond speaking of which how

did you make your first billion so my partner Todd Wagner and I um would get together for lunches and we were at

California Pizza Kitchen in Preston Hollow in Dallas and he was talking about um how we could use this new thing

called the internet this is late 94 early 95 to be able to listen to Indiana University basketball games because that

that's where we went to school and he was like look when we would listen to games we would have somebody in

Bloomington Indiana have a speaker phone next to a radio and then we would have a speaker phone in Dallas and you know

sixpack or 12 pack of beer and we sit around listening to the game because there was no other way to listen to it

so I was like okay okay my first company micr Solutions you know I'd written software done Network integration and so

I was comfortable digging into it and so I like okay let's give it a try so we started this company called audionet and

effectively became the first streaming content company on the internet and it we were like okay we're not sure how

we're going to make this work but we were able to make it work we started going to radio stations and TV stations

and you know music labels and everything and um evolved aet.com which is only audio at the beginning to broadcast.com

in 1998 which was audio and video and became the largest multimedia site on the internet took it public on in July

of 1998 it had the largest first day jump in the history of the stock market at the time and then a year later we

sold it to Yahoo for $5.7 billion in Yahoo stock and I owned you know right around 30% of the company give or take

and so after taxes that's what got me there well there's a lot of questions there so the technical challenge of that

you're making it sound easy but uh you wrote code but still in the early days of the internet how do you figure out

how to create this kind of uh product of of of just audio at first and then video at first a lot of iterations right like

you talked about um we started in the second bedroom of my house set up a server I got an ISDN line which was a

128k line and set up downloaded Netscape server and then started using different file formats that were Progressive

loading and allowing people to connect to the server and do a progressive download so that the audio you can

listen to the audio while it was downloading onto your PC yeah was it super choppy so you trying to figure out

yeah for sure for sure it would buffer it was yeah was it it wasn't good but it was a start but it was good enough cuz

it's the first kind of yeah because there was no other competition right there was nobody else doing it and so it

was like okay I can get access to this this or this and then there were some third party software companies zing and

um Progressive networks and others that were that took it a little bit further so we partnered with them and I started

going to local radio stations where literally we would set up a server right next to it I had a

$49 um radio the highest FM radio that I could find and we take the output of the audio signal from the radio with these

two analog cables plug it into the server encode it and make it available from aet.com then I would go on yunet

bulletin boards I would go on CompuServe I would go on Prodigy I would go on AOL I'd go wherever I could find bodies and

I'd say okay we've got this radio station klif in Dallas it's got Dallas Sports and Dallas um news and politics

and if you're in an office or you're outside of Dallas connect to aet.com and now you can listen to these things

on demand and that's how we started and it started with one one radio station and then it was five then it was 10 then

it was video content then it um the laws were different then so we could um literally go out and buy CDs and host

them and just let people listen to whatever music and we went from you know 10 users a day to 100 to a thousand to

hundreds of thousands to a million over those next four years how did you find the users is it Word of Mouth Word of

Mouth mou didn't spend a penny on Advertising so the thing you were focusing on is getting the radio

stations and all or radio and TV anything any content at all you pick up the phone what did you how you I would I

wherever I could like everything that was public domain I'd go out and buy a video or a cassette whatever it was you

know um and this is before the the DM the digital minim Copyright Act of 90 whenever it kicked in so literally

anything that was audio we would put online so people could listen to it and if you think about somebody at work they

didn't have a most likely and if you did you couldn't get reception definitely didn't have a TV but you had a PC and

you had bandwidth available to you and the companies weren't up on firewalls or anything at that point in time so our in

office listening you know during the day what just exploded because whoever was sitting next to you what are you

listening to right and that was the start of it and then you know in early 98 um we started adding video and just

other things and we had end up with thousands of servers you know there was no cloud back then and um and just

pulling together all those pieces to make it work but where we really made our money was by

taking that Network that we had built and then going to corporations and saying look you know it's 1996

9798 and to communicate with your worldwide employees what they would do is they would go to an auditorium that

had a satellite uplink and then they would have people go to like theaters or ballrooms um and hotels that had

satellite downlinks and then would broadcast you know the product introductions whatever and so we said to

them look you're paying millions of dollars to reach all your employees when you can do it um pay us a half a million

dollars and we'll do it just under their PCS at work so we did you know when Intel announced the P90 PC we you know

charged them $2 million or whatever to do that when Motorola announced a new phone or a new product we would charge

them and so we Ed the consumer side to do a proof of concept for Network um and then we would take that knowledge and go

to corporations and that's how we made our revenue and there's some selling there with the corporations yeah a lot

of selling there but we were saving them so much money and they were technology companies they wanted to be perceived as

being Leading Edge and so it was winwin uh how much technical Savvy was required you said a bunch of servers like at

which point do you get more Engineers how much did you understand could do yourself and then also once you can't do

it all yourself how much technical Savvy is required to understand enough to hire the right

people to keep building this and Innova I did all the technology and then we hired engineer after engineer after

engineer to implement it and so wow yeah um from putting together a multicast network to um software to just all these

different things was this like a scary thing like it's terrifying right because as we were growing trying to keep up the

scale and literally we're buying off-the-shelf PCS and then you know cars as the technology advanced and hard

drives and things would fail and we would have to you know we didn't have machine learning back then to do an

analysis of you know how to distribute server you know resources so you know like there was there was a time when um

Bill Clinton and all the Monica Lewinsky stuff happened they released the audio of um their interviews of him or

something like that right and we literally we I knew at that point time when that was released everybody at work

was going to want to listen to it right so we had to take down servers that were doing Chicago Cubs baseball right you

know and just make all these on the-fly decisions because there was no we didn't have the tools to analyze or predict be

predictive but yeah it was it was all technology driven and marketing um the acquisition by Yahoo

can you tell the story of that but also in the broader context of this internet bubble this is a fascinating part of

human history yeah so so on the acquisition side we were the largest media site on the internet it wasn't

close there was nobody close we were YouTube and relatively speaking we would be 10x YouTube relative to the

competition because there was nobody there um and so it became obvious to Yahoo AOL and others that they needed a

multimedia component and we had the infrastructure sales all that stuff um and so

Yahoo when we went public in 98 or right before I think it was they made an investment of like $2 million which gave

us a connection to them and then after we went public they decided they needed to have multimedia and so in April of 99

we made a deal and then July of 2000s when it closed and uh can you explain to me the

trickiness of what you did after that oh the um the collar yeah okay so when we sold to yah we sold for $5.7 billion in

stock not cash and so I looked at I you know after micro Solutions um when I sold that um I took that money and

initially I I told my broker I wanted to invest like a 60-year old man because I wanted to protect it um but then he

started asking me all kinds of questions about all these technologies that I understood like networks I had installed

we had become one of the top 20 let's say um systems integrators in the country at one point in time we're the

largest IBM token ring um installer in the country it was crazy right Bon name blast from the past I mean so anyway so

these Wall Street Bankers um or analysts rather um that were the big analysts of the time would call me up because they

would ask my broker what does he know about this product this and I knew them all what was working and not working

right and so the ones that work you know I say it's working i' see the stock they say something the stock would go up 20

bucks right so I'm like like well and my broker was like you need to you know this better than they do you need to

invest so I started buying and selling stocks and this was in 1990 and was just killing it I was

making 80 90 100% a year um over those next four years to the point where guy came in and asked to use my trading

history to start a hedge fund which we did and I sold within nine months it was great right but the point being as it

goes forward so when um we sold to Yahoo I already had a lot experiened trading stocks and I had seen different bubbles

come and go a bubble for PC manufacturers a bubble for networking manufacturers they went up up up up up

and then they came straight down after the hype or somebody just um Lea frogged and so when we sold to Yahoo um I was

like I've got a be next to my name that's all I need or all I want I don't want to be greedy and I'd seen this

story before where stocks get really frothy and go straight down and and I knew that because all of what I had was

in stock I needed to find a way to collar it and protect it so understanding stocks and trading and

options and all that my broker and I we went and shorted an index that had Yahoo in it and so the law at the time was you

couldn't short any indexes that had more than 5% of that stock in it right that of anyone's of the Yahoo stock and so um

I took pretty much 20 some million dollars everything I had at the time and I sorted the index this is fascinating

by the way cuz it's based on your estimation that this is a bubble or just mind not want be to be greedy sure so

you're the foundation of this kind of thinging is uh you don't want to be greedy yeah I mean how much money do I

need right you know where other people were saying oh I think can go up higher higher higher I was like I went on CNBC

and um I told them what I had done and they were like in Yahoo stock had gone up significantly from the time I had had

collared and one of the guy Joe and was on there don't you feel stupid now that yaho stock has gotten up um you know x%

more I'm like yeah I feel real stupid sitting on my jet but so you I mean there is some

fundamental way in which bubbles are based on this greed greed and I'd seen it before right like I just said and so

what I did was we put together a caller where I sold calls and bought puts and as it turned out when the market just

cratered I was protected and you know over the next two three years whatever it was it it converted to cash paid my

taxes Etc but um it protected me and as it turns out it was called one of the top 10 trades of all time and what was

even more interesting out of that period um my broker at that time was at Goldman Sachs and I had asked him to see if

there was a way to trade Vic the vix right the volatility index and there there wasn't right and so one of the the

people that Goldman that we were working with to try to create this actually left Goldman and created indexes that allowed

you to to trade the vix it's not trivial to understand it's a bubble I mean you're kind of lessening your insight

into all this by saying you just didn't want to be greedy but you still have to see that it's a bubble yeah I mean yeah

obviously if I thought it was going to keep on going up and it was there was intrinsic value there I would have

stayed in it but it it wasn't so much Yahoo it was just the entire industry you would back then you know like we're

looking at the the magic 7 or whatever it is stock now and people are asking is it in a bubble and when I would get into

cabs and people just start talking about internet stocks there were people creating companies with just a website

and going public you know that's a bubble right where there's no intrinsic value at all and people aren't even

trying to make operating cap profits they're just trying to Leverage The frothiness of the stock market that's a

bubble you don't see that right now there's not companies you don't see hardly you don't see any IPOs right now

for that matter so you know I don't think we're in a bubble now but back then yes I thought we were in a bubble

but that wasn't really the motivating factor do you think it's possible we're in a bit of an AI bubble right now no

because we're not seeing funky AI companies just go public if all of a sudden we see a rush of companies who

are skins on other people's models or or just creating models to create models that are going public then yeah that's

probably the start of a bubble um but that said my my 14-year-old was bragging about buying Nvidia you know with me in

in his Robinhood account he tells me the order I place it and he was like oh yeah it's going up up up you know and I'm

like yeah we're not quite there yet but that's you know that's one thing to pay attention yeah we're flirting with it

yeah uh you said that becoming a billionaire requires luck yeah can you explain yeah I mean there's no business

plan where you can just start it and say yeah I'm definitely going to be a billionaire you can you know if I had to

start all over could I start a company that made me a millionaire yeah CU I know how to sell and I know technology

and I've learned enough over the years to do that um could I make 10 million probably 100 million I hope so um but a

billion just something good has got to happen you know um timing timing you know Internet stock market was going

nuts right when we started you know and that certainly I couldn't predict or control um you know it's like AI right

now ai's been around a long long long long time and the Nvidia processors or gpus rather you couldn't predict that

now's the time that they were going to be get to that cost Effectiveness where you know you could do you could create

models and train them and although it's expensive it's still doable you know we didn't really even we had as6 right for

custom applications and we had CPUs that were leading the way but gpus were more for gaming and then crypto Mining and

now all then all of a sudden they were the foundation for AI models so think luck being essential to becoming a

billionaire is a beautiful way to see life in general first of all I personally think that everything good

that's ever happened to me is because of luck I think that's just a good way of being it's like uh you're grateful that

said there's some examples of people that you're like they seem to have done a lot of they seem to have gotten lucky

a lot you know we mentioned Jeff Bezos it seems like he did a lot of really interesting

powerful decisions for many years with Amazon to make it successful but he was really able to raise money right a lot

of money and people were really dismissive of him because they weren't um making they weren't profitable and we

we were in an environment where it was possible to raise possible to raise that money I mean what about somebody you get

sometimes uh feisty with on the internet Elon but we couldn't even look at Zuck and Bill Gates and Warren Buffett look

Zuck was just trying to get laid right and it took off and you wrote some good stuffff AR we all is some level

Foundation of human civilization right but um yeah so more power to them right you can't take anything away from them

but yeah Snapchat same thing took off apps didn't take off in 2007 when the iPhone came out apps took off in 2011

2012 and if you were there with the right app at the right time and even Facebook um you know in 2004 the bubble

had burst and you know the price for computer had fallen enough and kids in school all needed computers or laptops

if he had tried to do something like that you know 5 years earlier I mean it was too young but you know five years

earlier or five years later you know frster might have been the ultimate or Myspace frster remember frster or

Myspace I had a MySpace account and that was before Facebook yeah the timing is important but there's like the details

of how the product is built the fundamentals of the product like what well so but that's what gets you when

the opportunity is there right that's what allows you to take advantage of that opportunity and and

the Kismet of it all right you've got to be because it wasn't like any of the people I mentioned there weren't others

trying the same thing yeah right you had to be able to see it you had to be able to visualize it and put together a plan

of some sort or at least have a a path and then you had to execute on it and do all those things at the same time and

have the money available to you because it wasn't like whether it was Google or Facebook you know they raised a shitload

of money it wasn't bootstrapping it that got them there and raising money is not just about sales it's about the the

general feeling of the people with money at that time in proximity if duck wasn't at Harvard and

he was at Miami of Ohio University or he was at Richland Community College same idea same person same execution and

nothing I believe in the power of individuals to find their to realiz their potential no

matter where they come from but I agree I agree 100% with that right but luck is required yeah I mean scale is the only

Delta is scale yeah right we you know we're not all blessed with the access to the tools that you need to to hit that

grand slam but then also billion is not the only measure of success right absolutely not right there's a everybody

defines the success in their own way how do you define success Mark Kean waking up every day with a smile excited about

the day you know I was you know people always say well when you get that kind of money does it make you happy and and

my answer always is it if you were happy when you were broke you're going to be really really really happy when you're

rich but you got to work on being happy when you're broke I guess well you're just being happy right if you were

miserable you know in in your job before there's a good chance you're still going to be miserable if that's just who you

are that's a pretty good definition of success by the way thank you how do you reach that success by way of advice to

people you you know we talked about my dad U my parents I never looked at my dad and

said okay you're not successful he busted his ass and when he came home you know he we enjoyed our time together

right there was nothing at any point in time where I felt like oh this is miserable we're awful we're you know we

don't have this we don't have that you know we we celebrated the things we did have and um never knew about the things

we didn't have you know and and so I think you know you have to be able to find your way to whatever it is that

puts a smiling on your face every day some people can do it and some people can't it's not always about the smile or

the smile on the outside it could be a smile on the inside yeah whatever it is right whatever makes you feel good yeah

the the struggle even the struggle like with your dad the the really really hard work can be can be a fulfilling

experience because uh the struggle leading up to then seeing your kid exactly right right because that's that

that was my dad's grand slam right seeing three kids go to college be successful you know spend be able to

spend time with him and that was the other thing you know he really made me realize is the the most valuable asset

isn't the money it's your time that's why you know from a young age I wanted to retire because I wanted to experience

everything that I possibly could in this life and you know he got joy from us I get joy from my kids um and that's the

most special thing you ever can have beautifully said you have made some mistakes in your life yeah a lot of them

one of the bigger ones on the financial side uh we could say is uh Uber yeah we call that not doing something yeah it

wasn't a mistake it was just I mean it was a mistake but I like how you tried to you

I always try to look at mistakes at things you did that didn't turn out as opposed to things you did to you know um

the negative but but what can you tell the story of that and maybe it's just interesting because it is illustrative

like how to know when a thing is going to be big and not and what are the fundamentals of it and how to take the

risk or not and all this kind of stuff right so the backstory of that is Bill Gurley came to me and said um Mark

there's this guy Travis that has this company red swoosh which is a peer-to-peer networking company that um

I think you can help and so I invested and would spend a lot of time with Travis and it's funny because back then

that was like 2006 I was an investor at at um box.net with Aaron Levy and oh there's one other company but there were

three of them where there'd be emails between you know where I'd introduce them and we'd all talk in these emails

and they'd all gone to be have astronomical success right um but so red swoosh had its issues you know cuz I

always look at peer-to-peer as kind of stealing bandwidth from the internet providers when bandwidth was a scarce

commodity um and so you know what Travis did with that though was great you know he convinced gaming companies who wanted

to do downloads of the clients for those games to use his peer-to-peer in red swoosh and you know he busted his ass

and I think he sold it for $18 million so he did well and so it was natural for him to come to me and I still have the

emails you know and asked me um about Uber cap and I thought okay this is a great idea I really really like it I

said you're going to and he showed me his budgets and I think they were raising money at 10 or $15 million or

whatever and um I'm like your biggest challenge is going to be you're going to have to fight all the incumbent taxi

commissions they're going to want to put you out of business that's going to be a challenge and I think you don't have a

enough money designated for marketing to get all that done and I said I'd invest but not quite at that valuation right

never came back to me yeah I mean there's some lessons there connected to uh what you're doing

now we'll talk about a Cost Plus drugs is like looking at an industry that seems like there's a lot

of complexity involved but it's like hungry for revolution for sure and the Cals are that yeah for sure right they

were they were dominated by an insulated few they were not very transparent you didn't know the intricacies they were ve

very politically driven um and old boy incestuous Network and to tra you know and like I told him Travis the best

thing about you is you'll run through walls and break down barriers the bad thing about you is you'll run through

walls even if you don't have to you know yeah and there you kind of have to see is it possible to raise enough money is

it possible to do all this is it possible is it possible to break through and it's kind of a fascinating success

story with Uber is I think he tried to go too big he had too big an ambition which cost him in the end not

financially and personally but just you know in terms of being able to stick it out with them um but you know that's

what makes him a great entrepreneur well it's a fascinating success story you have like certain companies like

Airbnb just kind of go into this thing that we take completely for granted and change it all just change it all yeah

blinda Johnson who worked as our general counsel at broadcast.com was you know was Brian's um GC and Chief Operating

Officer so yeah they they had a smart smart smart smart team and they believed in it and they I mean it's just it's a

it's a beautiful story cuz you're like all right all the things that annoy you about this world like they're

inefficient and it just seem like pain I probably would have said no like a lot of people did to Airbnb because I'm like

I don't want people sitting my sleeping in my bed I would have too I was like this is not going to work I've done like

cou surfing and stuff and it was always it didn't seem right it didn't seem like you could do this at a large scale to

monetize it yeah but he did more power to him in 2000 I think January you purchased a majority stake in the the

NBA team Dallas Mavericks uh for 285 million so at this point maybe you can correct me but it

was one of the worst performing teams in franchise history uh true how did how did you help turn it around um I had

this big tall guy named Dirk niski and I let him be Dirk nitzki right and I got out of the way um but I think more than

anything else um there was the turnaround on the business side and then there was the turnaround the basketball