Transcript

Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)

From Young and Profiting · Episode page · Watch on YouTube

· 1 h 17 min · 14,472 words · 190 timestamped sections

This is the full, timestamped transcript of "Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)", an episode of Young and Profiting published December 1, 2025 (1 h 17 min, about 14,472 words). It mentions 45 people, works and ideas, including The Learning Company, Mr. Wonderful, Customer Acquisition Cost (CAC), Signal vs noise, American Girl.

What this episode is about

Kevin O'Leary emphasizes the importance of personal accountability in entrepreneurship, arguing that founders must take full responsibility for their businesses instead of blaming external factors like market changes or competition. He discusses the critical transition from entrepreneur to leader at the $5 million revenue mark and highlights the need for balance and continuous effort in building and scaling a successful business empire.

Key takeaways

  • Blaming external factors is easy; taking ownership signals a true leader.
  • Entrepreneurship promises freedom, but the cost is eternal hard work.
  • At $5M, shift from solo warrior to motivational leader or risk plateau.
  • Shark Tank is a success thanks to the unexpected loyalty of Disney's exec spouse.
  • MBA value lies in networking, not textbooks—connections trump spreadsheets every time.

Who speaks in this episode?

What is discussed, and when

  1. – 10:00: Mr. Wonderful, Magoo's Ice Cream Parlor, Mumbai, Shanghai
  2. – 20:00: The Learning Company, American Girl, Fisher-Price, Miss Mu
  3. – 30:00: Airbnb, Shopify, Al Jazer, American Girl
  4. – 1:00:00: Atkins diet, Lose It!, Ronnie Bronstein, Venture capital model
  5. – 1:10:00: Creator entrepreneurship, Montrachet, Mr. Wonderful, Plaza Hotel
  6. – 1:17:18: Anthony Joshua

Notable quotes from "Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)"

  • In, this, episode,, we're, diving, deep, with the one and only Mr. Wonderful himself Kevin Oolirri. Kevin is a world famous entrepreneur, investor, Shark Tank star and a self-made multi-millionaire who's turned setbacks into strategies for.
    about Mr. Wonderful · at
  • Setbacks into strategies for massive success. We'll talk about how Kevin built and sold the learning company for $4.2 billion. why culture clashes can destroy great businesses…
    about The Learning Company · at
  • In a row and it was kind of interesting that Disney just kept it going and we found out that Will Oay Iger's wife was part of the reason her kids were watching it. She loved the show.
    about Will Oay Iger · at
  • Making films for the NHL for Saturday hockey games and built a business. We eventually sold it called Special Event Television. It was my first exit. So, I kind of got in the…
    about Special Event Television · at
  • Treasury, bills., US, Treasury, bills., I'm, you can also buy gold but doesn't have any yield. I have tea bills. I roll a bunch of tea bills.
    about US Treasury bills · at
  • Advantages was they had these incredible brands like Fisher Price and Barbie and American Girl. And so what we had modeled out in the learning company so successfully is I had…
    about American Girl · at
  • Snowball fights, too, if I'm lucky. Of course, I'll be booking my stay on Airbnb because I love finding places that feel like home, but still have that getaway vibe. But here's…
    about Airbnb · at
  • Finding the right platform with all the tools I need to succeed. That's why I trust Shopify because they get it. They started small, too. Shopify powers millions of businesses around the world.
    about Shopify · at

Who and what is mentioned in this episode?

People

  • Mr. Wonderful — Person · 4 mentions · first at
  • Ashley Ala — Person · 2 mentions
  • Will Oay Iger — Person · 1 mention · first at
  • Ronnie Bronstein — Person · 1 mention · first at
    You ever heard of Josh Sa? He said yeah that's the guy that directed Uncut Gems and Ronnie Bronstein wrote it. It's great movie, Adam Sandler dark, comedy.
  • Anthony Joshua — Person · 1 mention · first at
    Out to my guest outreach team for always being on top of their game. Shout out to Hasham for Khan and Joshua for absolutely crushing it and for snagging an incredible guest like Kevin or Liry.
  • Dr. Ken Barry — Person · 1 mention
  • Hasham Khan — Person · 1 mention
  • Josh Safdie — Person · 1 mention
  • Steve Wozniak — Person · 1 mention

Companies & orgs

  • The Learning Company — Company · 5 mentions · first at
  • Special Event Television — Company · 1 mention · first at
  • Magoo's Ice Cream Parlor — Company · 1 mention · first at
    Magoo's Ice Cream Parlor. That was the name of it. And I wouldn't scrape the gum off the floor because the girl I was hot for in high school was selling shoes across the mall and she was watching me.
  • Fisher-Price — Company · 1 mention · first at
    Doing our plans, one of the great advantages was they had these incredible brands like Fisher Price and Barbie and American Girl. And so what we had modeled out in the learning…
  • Niscoco Brands — Company · 1 mention · first at
    Earlier just for the summer you know between my first and second year of MBA Niscoco Brands and I worked for a Dutch product manager who had Miss Mu cat food and I it's…
  • Al Jazer — Company · 1 mention · first at
    Sunrise and I'm listening to all of my messages or the feeds of the networks. I listen to BBC, Al Jazer, Fox News, Fox CNBC, all of them. I just listen for the seven stories of…
  • Wondercare — Company · 1 mention · first at
    In value over time. So, you want to get the replacement price. So, that's what we offer WonderCare. to do that business. I partnered with seasoned professionals on the tech…
  • Chubb — Company · 1 mention
  • KevinOLearyTV — Company · 1 mention
  • Yap withhala — Company · 1 mention

Products & tech

  • American Girl — Product · 2 mentions · first at
  • Oura Ring — Product · 2 mentions
  • Yuka — Product · 2 mentions
  • Oregon Trail — Product · 1 mention · first at
    You would always hit your target. So, if you're going to drop a new version of Oregon Trail, you're going to make 12 million copies. You have to manufacture them. You got a…
  • Miss Mu — Product · 1 mention · first at
    Between my first and second year of MBA Niscoco Brands and I worked for a Dutch product manager who had Miss Mu cat food and I it's remarkable how experiences in your life that…
  • Big Bird — Product · 1 mention · first at
    Just do math and reading core code and then we add a license like a, you know Big Bird or we get, you know whatever, character we would go license, whatever it was. It was Big…
  • The Muppets — Product · 1 mention · first at
    Whatever, character we would go license, whatever it was. It was Big Bird, it was the Muppets, was whatever it was. And we just slammed it on top of one of the engines. And my…
  • Atkins diet — Product · 1 mention · first at
    Decided that food is important to them. Not some crazy Atkins diet, none of that stuff.
  • Lose It! — Product · 1 mention · first at
    Protein based. There's lots of ways to do it. There's lots of apps you can use lose it. It's free. Just take a picture.
  • Montrachet — Product · 1 mention · first at
    It's 7:00 in the morning. I said Not for me, it isn't. I just got back from 1952. I need a bottle of Montrachet.

Concepts & topics

Places & events

  • Mumbai — Place · 1 mention · first at
    To do it in something that you're willing to work 25 hours a day, 8 days a week cuz some guy in Mumbai or Shanghai is kicking your ass.
  • Shanghai — Place · 1 mention · first at
    To do it in something that you're willing to work 25 hours a day, 8 days a week cuz some guy in Mumbai or Shanghai is kicking your ass.
  • Sea of Japan — Place · 1 mention · first at
    Which are boiled in papaya juice and compressed or it's tuna from the sea of Japan dark, the, underbelly, of, tuna, that, is, your protein base your job is to dream up a flavor…
  • Plaza Hotel — Place · 1 mention · first at
    Wants to do is create an environment with like 100 extras and you we took over the Plaza Hotel from 7 at night to 7:00 in the morning. And I'm just remembering this one sequence we shot all night long.
  • Casa Cipriani — Place · 1 mention

Sponsors

Full transcript with timestamps

There's so many people that want to believe. Oh, the market changed. Oh, the competitors changed their prices. Oh there was dumping on the market from China. yada yada yada yada yada yada. All, The, founder, and the CEO. They are the person who failed. Unless I hear that, I never invest in them.

In, this, episode,, we're, diving, deep, with the one and only Mr. Wonderful himself Kevin Oolirri. Kevin is a world famous entrepreneur, investor, Shark Tank star and a self-made multi-millionaire who's turned setbacks into strategies for massive success. Entrepreneurship is a disease, actually. It's a virus, and it never sets you free. And so, you have to know that. And the more successful you are, the harder you work, you're never going to be free. And then you have to decide, what's my life balance like? Well, there isn't any. It's a concept. You know, when I go to value a company, there's only two people I want to talk to before the CEO. Just those two people will tell you is this a good business or not? I want to meet the person running and I want to meet the head of a lot of entrepreneurs forget to do this. Get that first 5 million really secure

in, your, name. I, like, that, goal. It's, a, good, goal., It's, enough, to, push you, but you're not going to stop working. You're going to keep going.

So,, what, needs, to, change, at, 5, million, to then hit 10 and 30 and 100? At, the, 5, million, point,, you, need, to transition from being the entrepreneur to the leader. And many fail at that point because

Hello, young, and, profits., What, does, it take to build an empire, sell it for billions, and stay on top when the stakes are skyhigh? In this episode we're diving deep with the one and only Mr. Wonderful himself, Kevin O. Liry. Kevin is a world famous entrepreneur investor, Shark Tank star, and a self-made millionaire who turned setbacks into strategies for massive success. We'll talk about how Kevin built and sold the learning company for $4.2 billion. why culture clashes can destroy great businesses and the biggest lessons he's learned from decades of investing in over 50 companies. Kevin also shares his secrets to staying focused on what matters, cutting through the noise, managing the emotional roller coaster of entrepreneurship, and using storytelling and personal branding to dominate in today's creator economy.

Believe me, you don't want to miss this conversation. And without further delay Kevin, welcome to Young and Profiting Podcast.

Thank, you,, Ala., Great, to, be, here., I'm, so excited for this interview. I've been watching Shark Tank for years. It was actually like the show that me and my family always watch.

I, think, Shark, Tank's, older, than, you, are. I, wish., But, I, watched, it, all, the, time. And now I'm running a company that's about to hit eight figures this year and I feel like Shark Tank was really one of the things that inspired me when I was growing up. So, thank you for all the work that you've done for young entrepreneurs.

Yeah,, we're, very, proud, of, the, platform. We certainly didn't know when we started out what would happen. Um the first three years it was cancelled three years in a row and um it was kind of interesting that Disney just kept it going and we found out that Will Oay Iger's wife was part of the reason her kids were watching it. She loved the show.

She, was, an, advocate, for, us, and, then, of course season 4 it exploded. It's, just, like, a, classic, in, terms, of, TV and you guys have done so much. So Kevin, you're one of the most recognizable businessmen in the world. You're an extremely successful entrepreneur, but what was Kevin like growing up?

You, know,, I, was, like, any, other, kid., I, um I was really very interested in that time in photography and I was part of the photo club in my high school and I told my father I wanted to pursue photography and film production and he said, "You're going to starve to death. You're just not good enough. You just you got to realize you're competing with a million other people want to do the same thing and there's nothing special about what you do." That's you would think that would be very hard love to hear from a stepfather but he was factually correct.

Um, and, he, it, forced, me, to, take, a different path to pursue you know some business business education which ended up being

immensely, valuable, but, not, for, the education I learned later. I, don't, remember, anything, I, did, in, my MBA at all. But I met all these people that went on to become leaders in pretty well all 11 sectors of the economy and I can phone them today and uh get instantly through to them and use them as my network. Business school is not about um you know balance sheet training or income. If you're successful an entrepreneur,, you're, going to, hire, a bean counter. So I don't do the books anymore, but I certainly needed that network to get ahead in those critical years. And I'm glad I did it. I'm glad I spent the time. So, an education isn't worthless, although there's lots of billionaires that never finished high school.

Yeah., So,, if, somebody, was, considering going to college or getting an MBA now would you say it's necessary or or don't do it?

No,, I, I, wouldn't, say, it's, necessary., I would say it's uh the reason you would do it is to understand for 24 months you're in a cohort of some of the most incredible people from around the world because these institutions I teach at them these Ivy League schools they curate an international group of people that are extraordinary and it doesn't mean they're all going to be successful but they all have unique attributes and they kind of build these cohorts around each other. So there you are put into this place where there's some really smart people challenging your ideas for two years.

Yeah. And, you, you, have, defend, for, yourself. But it has nothing to do, you know, it's it's when I teach these classes myself I walk in there and I say, "Look everybody, you're all going to forget me. It doesn't matter." But the real value in this class is is is is you

is, is, these, relationships, you're, forming in here. You should never forget that. And I think that's a wonderful thing. And if you can get in, it's worth it. And you know, that to me was what made it worth it. And now I know that with certainty because I'm decades past it.

I, got, a, 4.0, in, my, MBA., And, I, don't remember anything from what I actually learned. But I didn't go to an Ivy League school. And I have to say like I didn't really get connections from it. So I feel like if you go to an Ivy League school and you can get into an Ivy League school, maybe it's worth it. Otherwise,

well,, the, brand, helps,, Harvard, helps, MIT helps, any of these Ivy League names, I get it, but I think the pro the education, I'm glad I did it. And it certainly set me up to do, and by the way, I went right back into photography afterwards. But I figured out how to turn it into a business. I I started making films for the NHL for Saturday hockey games and built a business. We we eventually sold it called Special Event Television. It was my first exit. So, I kind of got in the groove of being an entrepreneur from from the p things I was passionate about. And that's the secret to entrepreneurship. You you want to do it in something that you're willing to work 25 hours a day, 8 days a week cuz some guy in Mumbai or Shanghai is kicking your ass.

Yeah. Because, they're, working, that, hard. Let's, talk, about, how, you, actually, got your start into entrepreneurship. I heard that you've only had one job in your life and you got fired on the first day.

It's, true., It's, the, ice, cream, story. Magoo's Ice Cream Parlor. That was the name of it. And um I wouldn't scrape the gum off the floor because the girl I was hot for in high school was selling shoes across the mall and she was watching me. I thought the only reason I took the job is to hit on her afterwards.

So, we, got, off,, you, know,, 6:00., But, um yeah, she whacked me and it was very humiliating and it actually was so important because it really gave me the understanding of there's the people that own the store and there's the people that scrape the off the floor

and, I, didn't, want, to, be, the, guy scraping. I wanted to own the store and and and I owe her a great um you know sum of gratitude and I went back to find her decades later when I could afford to bulldoze the whole mall myself if I wanted to but already been bulldozed.

So, I, never, found, her. But, most, entrepreneurs, I, talked, to, have that definitive moment that pushed them on the path towards entrepreneurship that somehow their lives are changed and they get this burning desire to pursue something where they're in control of their destiny. doesn't mean they're always successful

but, if, you, don't, have, that, fire,, you don't have that passion and you're not willing to take that risk, you're not going to succeed.

Yeah., So,, you, have, so, much, money,, right? But you're still working and you could retire today, of course. So, what actually drives you in entrepreneurship?

I, don't, need, more, money., Um,, I, need, more time. There's so many things I'm pursuing now that interest me. I'm able to invest in almost all of them. that they don't always work out but enough are you know successful. I mean the whole thing about money that that um a lot of people don't understand you're going to find this out as time passes and only the experience of going through it gives you the knowledge cuz nobody believes this when you know if you're an entrepreneur and you can sell $100,000 of the product to people that are not your relatives. That's the first thing cuz your aunt will always buy your from you. Yeah

but, that's, useless., You, got, to, sell, it to an arms length person who wants the product and the service independent of the fact that they want to help you. They want to be served a product that helps reduce a pain point for them. They're willing to pay you money for it. If you can do 100,000 of that, you can do 500,000. If you can do 500,000, you can do 5 million.

If, you, do, 5, million,, you, do, 50., If, you do 50 million, you can do half a billion. That's how it goes. But at the 5 million point that's when the whole system tests you because you need to be able to build a team. You need to transition from being the entrepreneur to the leader.

Yeah. And, many, fail, at, that, point., And, I, I, see this when I invest in them and I have to take them behind the barn and whack them eventually. They're still shareholders but they don't have the leadership skills, the ability to lead people so that you can get the leverage to build a business past 5 million. Um, but really what's driving you if you're going to do that is you want you're you're competitive and you want to win. And

I, never, thought, about, ever, the, money when we were doing the journey on my big exit, the learning company. Neither the other nine guys that were sort of founders.

Yeah., We, just, one, day, woke, up, and someone bought our company for 4.2 billion and we were all you know, filthy rich. And that didn't change anything. It we still we still went back to work the next day. It's weird, but it just doesn't matter. It's great to have the liquidity, but it doesn't really change your life that much.

Yeah. And, so, people, should, understand, that it's all you really need in the bank to be secure for the rest of your life is $5 million. And I tell every entrepreneur that go well past that. The discipline is get 5 million

and, put, it, in, tea, bills, and, just, look, at it. It's just sitting there and don't touch it because if poo poo hits the fan,

you're, still, good. What, are, T, bills, in, case, people, don't know? Treasury, bills., US, Treasury, bills., I'm, you know, you can also buy gold but doesn't have any yield. I I have tea bills. I roll a bunch of tea bills. That's my you account. And it always has been. I've never touched it. And you know, I buy dinner with the interest.

So,, you, never, touch, it, and, then, whatever you make off of it, that's what you spend.

Well,, that's, the, protection., I, had, that goal decades ago. I mean, it's more than five. It's grown over the years. I just leave it in there. But it it's something that gets you that sets you free. It's you know, it's it's a lot of money, but a lot of entrepreneurs forget to do this on their way.

Yeah., They, keep, rolling, all, the, dice, all the time and they don't take anything out and something goes wrong and they end up with nothing because it put too much leverage on their business or something, you know, happened. It's get that first five million

really, secure in, your, name, and, then, look, at, it, on, your phone every day and say, "I've achieved that."

Yeah,, I, like, that, goal. It's, a, good, goal., It's, enough, to, push you, but it's not and it's enough to to to make make it safe for you and your family, but it's certainly you're not going to stop working. You're going to keep going.

Something, that, you, said, reminded, me, of what Brandon Dawson talked to me about. So, he's a co-founder of Cardone Ventures and he's like a very successful entrepreneur and he was telling me there's like three pivotal moments for entrepreneurs like hitting 1 million hitting 10 million and 30 million. And like each one of those stages requires different things. You say you were just saying like five million to you is like a a pivotal point. So what needs to change at 5 million to then hit 10 and 30 and 100?

Yeah., You, won't, get, past, five, if, you haven't started to build a team because you know no one is perfect in all aspects of business. You have to hire to fulfill or fill in. It's like a crack in the wall. You put plaster on. You have to find and understand your own weaknesses and hire people that are strong in that attribute

and, give, them, equity, in, your, business. Make them your partner. It's it's sort of like Steve Jobs and Wnjak. I worked for those guys in the early 90s. They were both brilliant, but they had completely different skill sets. They couldn't have made it without each other. It was impossible. Um, but it's it's because of they had that because they had that partnership and they were able to build it together knowing they couldn't do it without each other. You will find out what you're weak at by the time you hit five. You may start it on your own and be just the sole proprietor, own all the shares, but your cracks will start to show at 5 million.

Now, it might be in logistics. It might be in compliance. It might be in accounting. It might whatever it is. You have to hire the person that's going to take that off your back so you can focus on your strengths. I'm sales and marketing that in that I trust. Very few people are better than I am at that. And that's arrogant be, but I'm I know I'm right. And so, that's my competitive weapon. You can't touch me. But I am at logistics. I don't care about worrying about the bookkeeping. I want someone else that knows what they're doing to do that. Um manufacturing, distribution, all that crap.

To me, the only reason those people exist is to serve my needs as the sales guy. There are no widgets if I'm not selling them. So, I value the saleserson in the the head of sales is more valuable to me than the CEO. I can always replace the CEO, but I can't replace a great saleswoman or a great salesman because they know not only their product inside out, they know their distribution channel, they have relationships with their buyers or whatever it is.

It's, all, about, sales., And, so,, you, know, when I go to evalu a company, there's only two people I want to talk to before the CEO. I want to meet the person running social media, and I want to meet the head of sales. and I take them out for dinner separately. We drink really good wine on my tab. Everything goes better with a couple of bottles of wine. You're going to learn a lot more. And then I know two things. What the sales distribution channel feels like and CAC and rorowaz customer acquisition costs and return on ad spend. Just those two people will tell you

is, this, a, good, business, or, not?, Because if they know what they're talking about and I know what they if they know right away.

Yeah. All, I'm, doing, is, pouring, gasoline, on, the fire and building the business because they've already figured out the business model.

Now, doesn't, mean, I, whack, the, CEO,, but usually you find out often the CEO is not the original founder and they don't have that much stock. It's some guy that found the company that's still in there that's you know the engineer or something. It's very it's different every time.

Yeah., But, sales, and, social, media, are really what it's all about. I, want, to, go, back, to, talk, about, the learning company. So you sold it for $4.2 billion.

Y and, later, on, the, company, basically failed after it was bought. And, for, me,, I've, got, this, company,, Yap Media. I've essentially been growing it for 5 years. And uh selling it really scares me because I know that like so much can go wrong after you sell your company. So walk us through like would you have done anything differently with that sale and like how should we think about exits as entrepreneurs?

So, that's, a, classic, example, of, failure of meshing two cultures together. Um learning company was extremely entrepreneurial. It would do a new title every four months maybe even every 90 days and we had a very tight relationship with retailers. Back then the distribution of software all software was on CDROMs slowly transitioning to online but majority of titles and particularly the gaming side were all CDROMs and so there was retail distribution and shelf space and purchases online and everything else but it was CDROMs and so you would go to Walmart or Target or any of the large retailers that had multiple yards of shelf space for their their software titles like records and you'd have a planagram set up for an annual basis and you would always hit your target. So, if you're going to drop a new version of Oregon Trail, you're going to make 12 million copies. You have to manufacture

them. You got a massive logistics problem. You're going to deliver them to every Walmart and every Target and every wherever else they were going. And you never missed that slot because the retailer was giving you maybe 18 in of space, which extremely valuable for, you know, six or seven facing SKUs. And so when we hit Walmart, um when we were doing our our plans, one of the great advantages was they had these incredible brands like Fisher Price and Barbie and um American Girl. And so what we had modeled out in the learning company so successfully is I had a job decades earlier just for the summer you know between my first and second year of MBA uh Niscoco Brands and I worked for a Dutch product manager who had Miss Mu cat food and I and I it's remarkable how experiences in your life that you inventory in your brain that you don't use for a decade come back and serve you later. Mhm.

I, guess, they, call, that, experience., But my, first, day, on, the, job, my, Dutch, uh,, you, know,, boss, basically said, "Look, you're going to be here for 4 months, and I want you to launch two new flavors so that we can get more shelf space on Miss Mew, but you should understand something about cat food. There's only two engines of protein. It's beef renderings and chicken faces which are boiled in papaya juice and compressed or it's tuna from the sea of Japan

dark, the, underbelly, of, tuna, that, is, your protein base your job is to dream up a flavor on one of those two engines of protein. So whether it's going to be bacon bits or egg bits or green pepper and you call that the flambe or something whatever it is because the cats don't have credit cards. it's their owners

that, buy, the, flavor, and, they, said, "Well, I think Kitty would love that one." And so, you have to dream up a flavor. And I was pretty good at that. But the the the thing that hit me when I went to the rendering plant to see the two stacks of protein manufacturing like the the face of a cow getting scraped off the skull and getting boiled in papaya juice was pretty freak, excuse my language, pretty freaky. I mean, it really freaked me out. and then slabs of tuna. But two engines, it was two engines and everything else was just

marketing marketing., Years, later,, I'm, looking, at our business at the learning company and we're, you know, we're just we're growing, but we had lots of competitors and I said to my partner cuz I had a fantastic because my weakness was logistics. So, I found a partner and became partners in the business. I was sitting with him one day in the office around 6:00 at night in Boston and I said, "I want to tell you a story about this trip to the rendering plant." And hear me on this because if you looked at our business that 80% of it was advancing math and reading scores. So we had math rabbit, read a rabbit, this title, that title. We're advancing these two scores that parents bought the titles for to advance those scores for their children.

Mhm., cuz, in, in, in, in, school, you, got, to it's math and reading all the tests right?

So, we, would, advance, math, and, reading scores. We're pretty good at it. And, I, said if if those are the two engines, math and reading why do we have all these programmers? Why don't we just get two teams that just do math and reading core code and then we add a license like a, you know Big Bird or we get, you know whatever, you know, character we would go license, whatever it was. It was Big Bird, it was the Muppets, was whatever it was. And we just slammed it on top of one of the engines. And my argument was "Our kids are four years old. They don't care if it's the same software. They're four and they're five and they're six.

They just want the character. So,, we, can, license, the, character., We, can fire twothirds of the of the coders which are really expensive, and just use the two tuna and beef.

That, that, was, the, moment, that, changed everything. And he said "I, love, it., Let's, do, it.", And, the hit the fan. There's even an article in the Wall Street Journal. I mean, it was just no one had ever done this in the software industry, the consumer software industry before. Our cost of capital dropped dramatically cuz our margins went up dramatically and we were so our our valuation was so high that we used our stock to to do hostile acquisitions on all our competitors. We ate them alive and we fired all their programmers and we just licensed our characters and we dropped our prices by 50% and we increased our volumes by 5x.

We took the software business down from $99 to $12.99 and, we, were, profitable all from that magic moment with that Dutch product manager showing me beef and tuna.

I, owe, so, much, to, that, guy., But, that's how life is. It's serendipitous. You don't know the moment that's going to change everything. We commoditized educational software. We sold hundreds of millions of copies of it in multiple languages all around the world of the tuna and the beef.

Mhm. That, was, it. Yeah., Yeah., And you, know,, so, when, we, tried, to, integrate that philosophy, going back to your original question, I I was I said to the CEO then, "Look

we're, going, to, have, to, get, the, Barbie title out in 90 days. We don't need anything. We're going to do it off the tuna and beef." She said, and she said "No,, no,, no,, no,, no., We're, going to, have to study this for 2 years." I said, "No no. We're going to study it for two minutes because we have an order for 12,000 units the first day and 12,000 the day after that and 12,000 the day after that. It's the holiday. We're putting it in for September. We've got $24 million worth of orders here just on the Barbie reading title.

And, then, we're, going to, do, the, American Girls title. Same thing. Then we're going to do the the math reading American Girl. It didn't matter to me but the philosophy there was completely different that these were very coveted brands and I understand it. But the amount of money we left on the table, the profit margins on just putting our own character onto a title our margins were like 70%.

So,, we, gave, up, hundreds, of, millions, of dollars. And that is what I call a cultural error because I didn't control the board, although I was one of the largest shareholders. And I went and saw the board said, "Guys, this is nuts."

Yeah. But, it, put, me, in, a, conflict, with, the management there. But I lasted quite a while explaining to them how to do it. And unfortunately, it didn't work out for them because they went and said "No, no, no. Let's wait two years." Two years it's over in the software business. We we left hundreds of millions of profit on the table.

Hey, y, fam,, the, holidays, are, around, the corner and you know that means travel family time, and making memories. I'm so excited because I'll be heading home to New Jersey to spend real quality time with my family. You know, I just moved to Austin and so I'm really missing them. I'm looking forward to the cozy dinners, catching up, and probably a few snowball fights, too, if I'm lucky. Of course, I'll be booking my stay on Airbnb because I love finding places that feel like home, but still have that getaway vibe. But here's a thought for my fellow entrepreneurs. Since I'll be away, why let my apartment sit empty while it could be earning some extra income? I'd love to host my space on Airbnb, but between running my company and this podcast, I'm not exactly the hands-on type. That's why Airbnb's co-host network is a lifesaver. You can hire a local co-host to take care of your home and guests. They're vetted on

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So, I know that you were you were essentially in this business for over a decade right?

Oh,, yeah. Once, you, were, out, of, the, business,, I know they bought you, you were still working in there, but once you were actually out of the business, did you have any sort of like identity crisis? Did you go through anything mentally? Well, I had a non-compete for 36 months. I was getting my full salary and

although, I, think, that's, illegal, today, but back then it wasn't. Um, and so I said to my family, uh, look, why don't we go visit every beach on Earth? Let's make it a mission to go to every great beach on Earth just for the hell of it. And after about 90 days of doing that, I was bored out of my mind. I just I said "What am I doing? This is crazy. I'm not in the game." And so um I immediately said okay what are I talked to my lawyer said what are the confines of of this non-compete I don't want to get into litigation what else can I do and he said well you can be an investor and you can start investing in startups and you can go on boards and you can I immediately said okay I'm going to do real estate and I started doing that and I got into climate control storage and I I started to diversify into all 11 sectors and you know my operating days were over and my investment days were starting and I was going through a

transition of from being the you know the operator guy to being the investor guy.

And, how, old, were, you, at, this, point? I, think, I, was 36. Oh, wow., So, maybe

40, I, don't, around, then., Um,, and, I, was, you know, pursuing my passions, watch collecting. Um, I was always a film editor and I wanted to keep my chops up and I was still cutting on an eight plate steambeck things like that. Um and and that then all of a sudden I started having some failures and successes on the investment side. And so I was starting to understand, you know I was starting to identify people and being able to read their traits to determine which which ones to back and which ones not to, which I've become, I think, very good at. And you know, I can see the ones that have what it takes.

But it's really from the experience that I learned during that time. Um, and life got even more interesting because today, you know, in in an average day, starting for me at 5:45, cuz I always ride my bike uh on Miami boardwalk along with a lot of other people do the same thing at sunrise and I'm listening to all of my messages or the feeds of the networks. I listen to BBC, Al Jazer, Fox News, Fox CNBC, all of them. I just listen for the seven stories of the day because I'm often going back on those networks and you know doing my contribution.

The phone will start ringing and in any one hour cycle there will be a phone call of utter catastrophe. um just got sued for $100 million uh you know product po food poisoning or something in the product line of the company I'm invested in whatever something catastrophic

minutes, later, total, euphoria just got an offer to be bought up for quarter million cash and you're you know trolling shareholder are you going to agree with this deal or not I'm thinking to myself you, you you, have, to, learn, how, to, be um what's a great word for it? You can't get emotional about this stuff

like, stoic. You, just, have, to, realize, that, for, every catastrophe there's euphoric outcome and by the end of the day your life is balanced again.

So, I, just, wait., I, wait, for, the, bad, news. I wait for the good news and I just roll with it. And I found it very very interesting to see how that plays out. And our portfolio is now 54 companies plus a bunch of other stuff we do. Um but I will say that um that was quite a journey to to understand how that works because you can hit me with I mean I people you're getting sued or something. I don't give a Like it just you know people that sue me and I get a lot of litigation because they're you know there's contingency lawyers. I always say to them go back and look at the last 30 lawsuits and show me, can you outlast me

because, I, know, how, you, work., You're, a single cell amoeba contingency lawyer. You're only going to be able to hold this up for seven years and I will outlast you

and, your, partners, will, say,, "We, got, to give up on this guy." But you should know that now cuz you know I got a lot of this crap. It, was, one, of the, bad, things, about, the system,

but, I, love, to, with, them. I, really, like, to, with, them. It's, really, powerful, what, you're, saying. You're saying like don't, you know, get too excited about the highs. Don't go so down when there's anything bad happening and the lows. So for new entrepreneurs that's really difficult. Like entrepreneurship, sometimes it can feel like you're just getting punched in the face over and over again. Um, and sometimes it it can be really good, but how can we better manage those highs and lows? What advice do you have?

It's, important, that, you, get, punched, in the face. It's important that you get bloodied and get knocked down multiple times. It will never be an easy ride ever. No matter what you think and no matter what you think your plan is, it won't be that that works. It just never is. And so really what the punch in the face is teaching you is how to pivot. And the more you get beat into a pulp the better it it gets because you start to realize if I go in that direction I'm getting another smack right in the face. I'm going to go in this direction.

It's less painful. It's sort of trying to figure out the path of least resistance based on your experiences of what didn't work. But I have never met anybody that's been successful ever that said it was easy, that ever said they were able to take their original business plan and execute on it because that never ever ever happens. or didn't go through hell on earth to get to where they are. Just and and so only onethird of the population can do it. That's it. And I'll tell you a story that I think is very important that I always bring up for everybody to think about. We talked about business school. You and I have both been there. In my last week in the second year they were getting guest, you know, Jamie Diamond kind of guys would come in and and lecture about their sector and, you know, people are going to go work in financial services or whatever. And this guy came in, I'll never forget it.

Never. I was probably the only one I'll ever remember of all the guests we had that week. And he didn't say anything for like a minute and a half. You know the amphitheater type thing. It's a staircase up the sides and you got 240 people sitting in this thing and got the name plate in front of you. He just looked at everybody and like for the most uncomfortable period of time and then he finally said, "Oh MBAs, you think you're so damn smart and you're just going to get out there and kick the world's ass and you just can't wait to leave here." Well, let me tell you what's really going to happen to you people. A third of you are going to become consultants and leave a life of mediocrity and never make a decision of consequence in your life and eventually go to consulting hell when you die.

Cuz it's true about a third of the class were going to become consultants. Y and, they, were, going, to, lead, a, life, of mediocrity and never make a decision of consequence. they were just going to be consultants, which is such a waste of a life. And then he said, "A third of you are think you're entrepreneurs and you're going to try and you're going to fail over and over and over again until you're an employee again because you don't have what it takes." Very depressing. And a third, he said, are going to work like hell for much longer than you think, and you will make it, but it will change you forever. It's so hard. And I leaned over to Barry, my guy beside me.

I said, "This guy is such an asshole." But, today,, that, guy, is, me. Because, when, I, meet, my, new, cohort,, I give them the same speech cuz he was right. He was 100% right.

And, so, it's, sort, of, you, learn, that, as, as time passes that the journey for entrepreneurship is into the valley of death. It it it has to be or you will never be successful. And when you get out of the valley of death and you all of a sudden have your five mil in your tea bills and and you're working even harder than you started because you're trying to do something else. Entrepreneurship is a disease actually. It's a virus

and, it, never, sets, you, free., And, so, you have to know that and the more successful you are, the harder you work. It's never you're never going to be free. And then you have to decide what's my life balance like? Well, there isn't any. That's a concept.

It's, The, idea,, oh,, I'm, I'm going to have time for my family. That's such That's such You might as well face it. You're going to work like hell. And as you grow a family, you better have a a better significant other that can take time to raise them because you won't have any. And I know that sounds like a sacrifice because it is. But you will buy your family freedom. That's what you will do.

Now,, do, you, feel, like, some, people, are not cut out for entrepreneurship at all? And do you feel like there's some people who can be, you know, some people are natural entrepreneurs. I think you're a natural entrepreneur and some people can be taught. What are your thoughts on that?

I, think, you, you, you, have, to, have, certain personality traits that I mean for me it's marketing and sales. Other entrepreneurs have great technical skills or whatever. Everybody has something that they are particularly good at that's in their DNA. But there are attributes you learn over time because you're getting punched in the face as you brought up earlier. These are important lessons that give you ammunition for the future not to make those mistakes again. There are some lessons and I've talked about this quite a bit lately um that I find very very important that I that I have to share with you because everybody should listen to this.

when working for Jobs for Steve Jobs in the early 90s. He not a nice guy. That's well documented. But he had a concept that I'll never forget and I've used it and it really works and and he changed me forever with this. He said in any day in any 18hour working day because he worked 18 hours a day. The guy was unbelievable. What a ferocious guy. I mean, damn. You never met anybody like him, but I hadn't. Anyways, he said, "There are three things you have to get done in this one 18 hour cycle." That is called the signal. Your ability to know what the three things are is what you must learn. But once you know what the three things are, that is the signal.

And all the things that will happen that stop you from getting the three things done is the noise.

Yep., And, the, ratio, must, be, 80%, signal, minimum, 20% noise, or you will fail. Wow. Was he right?

Yeah. And, so, if, you, can, learn, to, do, that, nothing could stop you. Unfortunately one of the problems with this strategy as you will find is you will have no time to suffer fools. You don't have any time. So if somebody comes at you with something that's clearly noise you don't have any time for them and they take it personally.

Yeah. I, don't, give, a, because, what, I've learned is they will come around when they realize that you're achieving your goals and you're executing. They will stay part of your team because they want to be led by somebody that gets it done and wins. And you can only win if you understand that you must get the three things done. You don't need friends in business. You need people that respect you. I I'm trying to teach this.

You, don't, need, to, make, everybody, happy because you can't. It's impossible. You want to make your friends and family happy, which is probably no more than 15 to 20 people that matter to you in your life. Everybody else is either noise or signal and you have to treat them that way because that's the right way to treat them. That's the fair way to treat them. That's what helps them get their job done. And I go through this every day. Now the only guy that I've seen that's higher ratio than Jobs was is Elon Musk.

100% signal will not waste one nancond on noise, which makes him very awkward socially. M

he'll, walk, away, from, conversation, two seconds the minute he knows it's noise

really. So, if, you're, not, contributing, towards getting something done, see you later. Ask anybody that works for him. But boy do they want to work for him because look at the success he's achieved.

People, want, to, follow, a, successful leader. So as an entrepreneur your job is not to make everybody happy. You will fail. You can't make everybody happy. You want to respect people. You want to honor them. and you want their respect, but don't try and make them happy. Not going to work.

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10, is, the, high, score. Got, it., I'm, interested., I'm, interested. All right., So, we're, going, to, rate, them one through 10. 10 being really needed for successful entrepreneurship. One being not so needed. Okay.

First, prompt. Creativity. 10. Why? That's, problem, solving., That's, when, you get punched in the face. If you don't have a creative bone in your body you're just going to keep getting punched in the face. You got to think outside of the box. That is the definition of creativity. You have to realize, ouch, that hurt. I don't want another punch like that. How am I going to solve for that? That is um using the brain.

Okay,, next, one., High, risk, tolerance. Um, I'm, going, to, give, it, a, five., Risk tolerance can also be stupidity.

Doing, things, because, you, I, can, take, the risk, I can take the risk and keep failing, you're an idiot. I mean the whole idea is to mitigate risk. In fact,, I'm, going to, give, it, a, one., Don't do stupid stuff. Like, don't do it. Don't don't keep risking it all over and over again. The whole idea is to find the path of least resistance without the risk. But it's true that when you launch, you're taking huge risk. But as you build it past the first 100,000, you want to stop taking the risks and start to mitigate the risk. So it's it's the launch itself, you need some kahunas because most people say, I don't want to do it. I'm not going to do it.

You have to try even though you're going to fail three times at least probably. But the four, you only need one hit to make it

to, get, your, five, mil, ski. Yeah. It's okay., being, able, to, tell, good, stories, or your storytelling ability.

10, 10, 10, 11 the world's changed so much that if you can't tell the story of your product or service, if you can't capture someone's imagination about the promise of your brand, you will fail. Storytelling is the whole deal because we are living in a social media customer acquisition cost model now for large and small companies. Great storytellers people that can capture the audience capture the potential customer, bring them into the aura of the promise of the brand. These are great entrepreneurs. These are great social media directors.

These are great editors, storytellers videographers, photographers. They tell stories., And, you, know what?, I'm, going to give it a 15. That's how much I feel about it.

Wow., Charisma not, important., I'll, tell, you, why., I, do business and invest in a lot of that have no charisma, but they have remarkable executional skills.

Charisma, can, be, also You know you want sexy charisma, you show me executional skills. That's sexy.

The, fact, that, you, can, set, a, goal, each quarter and hit it, that's charisma. So you know, traditional definition of charisma is when it comes to being an entrepreneur.

Industry, experience. Yeah., I'm, going, to, give, it, an, eight, and I'll tell you why. There's a concept developed in Europe decades ago, hundreds of years ago in places like Switzerland and France Germany, Italy, where they create apprentice programs where they bring talent in as young as 14 and they let them work for a stipen and a free lunch or whatever after their school at 4:00 till 7 at night so that they can experience what it's like to work in a business and understand what the passion is of that business whether it's watchmaking or farming. pharmaceuticals or tire making or uh high-end machinery in Switzerland, whatever it is, to see if they have the attribute or the DNA to connect with what that's about.

Particularly important in the watchmaking industry when they identify you to be a master watchmaker when you're 14, you're going to commit your whole life to it.

I, know, a, lot, about, that., And, that's industry experience, but at a very early age, so you can find out, do you connect with the cosmos of that business? And is that your path for your life? You don't know until you try.

Yeah. Okay,, last, one., Failing, fast. Yeah,, that's, a, that's, a, buzz, word, in, the valley. Um I I don't I don't put a lot of weight on it. I'll tell you why. I'm going to, give, it, a, two., But, here, here's here's the rule that I put in place. In your launch years in your mid to late 20s and you've decided you're going to pursue the entrepreneurial path, one of your most important assets is time. So, and I've seen this countless times with with entrepreneurs. I meet them in their fifth year of beating a dead horse

that, just, never, took, off., But, they're, so emotionally attached to this piece of idea, that, they're, going, to, bankrupt their parents through mortgaging their parents' home. I mean, I've seen it so many times. If after 36 months it's not working, and by working I mean it's growing and it's profitable and you clearly have figured out how to acquire customers. Take it behind the barn and shoot it.

I'll, do, it, for, you., Good, bottle, of, wine, shoot it behind the barn because it is killing you. It is it is sucking your energy and it is basically taking away from the most valuable thing you have the time to start a new idea. Entrepreneurs deal with failure. They have to because they're going to fail. There's no such thing of just starting something out of the basement. It happens so rarely that it won't happen to you. I can tell you that you can't I prefer to shoot them after two years. If in 15 months they haven't figured out CAC customer acquisition, they're going to fail.

Yeah., And, why, spend, any, time, on, a, dead idea that didn't work? It's okay. It didn't work. Who gives a Move on. I much prefer to invest in entrepreneurs that felt the sting of failure, but understand. So, you know, fail fast if it means take it behind the barn and shoot it early. Great.

But, shoot, it., And, don't, let, anybody, tell you, "No, you got to keep on going and wasting everybody's time and money." Because remember, the people that you're employing, you're also hurting them. You have a responsibility to tell the truth to them and say, "Look, I this idea didn't work. I'm going to fire you with as best, you know, package I can give you, but I'm also starting something else." You get a lot of respect for that., You, you you, really, do, to, admit failure and and own it. And the thing that drives me crazy about people and I'm telling you to listen to this because I get pitched a lot and I say, "Well what did you do before this? What were you doing the last two years?" And they talk about a business and they tell you it failed, but it wasn't their fault.

They'll, tell, you, every, reason, on, earth why it wasn't their fault. They should own it. It's 100% their fault. They were the founder and the CEO. It wasn't anybody else. They are the person who failed. Unless I hear that, I never invest in them. There's so many people that want to believe. Oh, the market changed. Oh the competitors changed their prices. Oh, there was dumping on the market from China. yada yada yada yada yada yada. All, They, failed.

So,, accountability, analysis 100%., And, some, of, them, walk, away, in tears when I force their nose into You know when, a, puppy, takes, a, in, the house and the first time you get a roll up a newspaper, stick his nose in it give him a little whack.

They, never, in, the, house, again., I stick their nose in their failure and I whack them with a newspaper and say "This is your You dumped this. You failed. Now smell it." That's what has to happen.

Well,, that, was, a, fun, game., Is, there, any other traits that you want to call out that you think makes a good entrepreneur?

Yeah,, I, I, I'm, going, to, give, you, some interesting uh points that I that I learned. Uh you know, after all this time and investing in so many different people and I after, you know, a few years, I start to see which ones are successful and I look at their traits and let me give you some. Remember these are in different sectors. They don't know each other, different businesses completely, and yet they're successful versus ones that are not so much because even in a venture portfolio like mine, maybe three out of 10 really work.

And, what, do, you, consider, a, successful business? Like how big do you have to grow before you can

Well,, you, know, what, you, the, classic venture capital model is if you invest in uh 10 deals, five years later, two have gone bankrupt. Um six of them are living dead, just sucking your time. They're not going anywhere. They should be shot behind the barn, but they won't shoot them. And two of them made a thousandx and um they paid for all your mistakes. So, you know, as an investor, you want to focus on your winners, and you got to figure out which ones are losers and winners. We do a little bit better on Shark Tank deals because we have 110 million eyeballs seeing the product in syndication. So, our customer acquisition costs are lower. So, call it three to four out of 10 work. Um, so even a marginal business works on Shark Tank. One of the reasons you want to get on Shark Tank is that free 8 minutes of network television on in perpetuity and syndication. It's ask any entrepreneur their product just keeps showing up on

television every night. It's pretty good. And so we want to invest in companies like that. But

what, happens, is, you, look, at, the, traits of those people in the winners and let me tell you what they are. Very boring in some ways, but you'll find this fascinating. Number one, this may sound crazy, but it's true. diet. Somehow along the way, they've decided that food is important to them. Not some crazy Atkins diet, none of that stuff. The rule that I learned from two of them, and they didn't even know each other, was they they look at their body weight, let's say they weigh 150 pounds they eat 150 grams of protein a day, one gram for each pound, which is very hard to do, by the way. Very hard. Um, but you don't have to modify your diet that much. You just have to decide what you're eating and it has to be more protein based. There's lots of ways to do it. There's lots of apps you can use lose it. It's free. Just take a picture.

AI tells you how many grams of protein in the serving and it just adds it up for you during the day.

And, the, other, app, that, I, use, because, I'm doing this myself now is Yuka Yuka. Scan any snack and it tells you a score from zero to 100. Anything lower than 60, don't put it in your mouth. After about 10 weeks of just following this protocol, your energy level goes through the roof. It's unfucking real how good you feel. That's number one. Number two, the classic exercise. All the entrepreneurs that are successful have found a way to spend some portion of the day exercising. Sometimes it's only 10,000 steps a day. That's it. I do cycling. Um those two together kind of this one is really interesting.

See, I'm wearing an aura ring here. I, got, into, this, about, four, years, ago., A great entrepreneur showed me this product. was more of a prototype back then. Sleep you know, decision making and critical thinking and sleep go together.

Yeah. So,, you, really, want, to, try, and, figure out sleep and it's not just any sleep. These rings and these other devices there's many other devices break down your sleep into the REM sleep and the deep sleep. You want REM sleep. That's your brain being cleansed for the next day. Unfortunately, sleep doesn't work with alcohol. And this is a big problem for me. I don't drink I mean, sorry, I I don't smoke. I don't do drugs, but I love wine.

And, if, you, drink, wine, 3, hours, before, you go to bed, you don't get any REM sleep.

It, really, your, sleep., So, the, strategy you got to go to is drink at breakfast and don't drink again because at the end of the day if you can get those seven hours the sleep the the diet and the exercise you can't believe how you feel as an entrepreneur. You need that energy and you're going to get it. And most of my entrepreneurs are hip to this now and are struggling with the whole wine thing or they're moving to the purest tequila or something or they don't drink it before they go to bed or they don't drink three days a week or whatever it is. Everybody's trying to solve for this alcohol problem because all the rings are showing you you get no rim.

And, one, last, one, and, this, is, the, one that that I really have learned um and you got to try it. Entrepreneurs once they're successful or the business or business growing their business get in a rut. They only want to do things that give them a good outcome because they've been trained or they punched in the face so many times that they get into this routine of only doing the things they know well over and over and over again all day long. And it's easy to get there, particularly when the team is humming, sales are coming in, everything's going great. But the one most important exercise you're not getting is that on your brain

because, you're, now, in, the, maintenance mode. And, that's, not, where, great, creativity comes from. So you have to get into a position, and this is very, very difficult, but I've done it. And believe me, it works. And I learned it from one of my great uh women CEOs years ago. She said, "You've got to spend a portion of every day outside of your comfort zone in some space that you're very nervous about getting into because you're scared you're going to fail and you're going to be embarrassed in front of your team or in front of your family or you can't do it or you don't think you can do it. It could be learning how to play the cello. It could be painting.

It could be ma jang or something or chess or it doesn't matter. It's something you don't know how to do that you're forcing your brain to deal with and the uncertainty. This gives you a superpower because you're basically recharging your ability to solve problems that you have no idea how to solve. And 50% of the time you're successful. This is the superpower for really good entrepreneurs to do and and yet no one wants to do it because oh I don't want to be embarrassed. So I'm I'm telling you the story because last year I got a phone call um from one of my agents and he said listen Kevin um have you ever heard of Josh Sa? He said yeah that's the guy that directed Uncut Gems and Ronnie Bronstein wrote it. It's great movie, Adam Sandler

dark, comedy. Said, he's, making, a, new, movie, called Marty Supreme and they're looking for a real and they think you're it. I said I don't act. He said, "Yeah, I know that." And I'm just telling you, if you're going to pursue this, you could the bed and destroy your brand. You could look like a real dick. But that's when it hit me. I got to do this. I got to try it. I got to see if I can learn 70 pages of script. You know, how do I do that when I'm dyslexic? How am I going to memorize all that stuff? I said, it do it. Like just see what happens. We finished it a few weeks ago. It's had some screenings and the buzz for Timothy Shalamé. So it's Timothy Shalamé. I'm Gwennneth Paltro's husband. It's a movie from the 50s.

Amazing. Yeah., It, was, shot, in, New, York, um, in Tokyo and it the experience was remarkable but the buzz for that movie and this has really not that much to do with me because I'm just a you know supporting actor is Oscar.

So, I, would, love, that, thing, to, win. I'd, like, Timmy, to, win, one., I'd, like, the director to win one because that would be great for my little contribution in that. But I worked on that for eight months and it was totally outside of my comfort zone. So, I'm waiting to see what audiences think when they see me in it. So, go see that movie Christmas Day.

Amazing. You, know,, Marty, Supreme., But, the, point is, do something today outside of your comfort zone, whatever it is, because you're not doing that. I know you're not doing that. No one's doing that. And it's a superpower.

What, do, you, feel, like, you, learned, from, you know, you were in this movie? Like you weren't just like a little blip at the movie. It sounds like you were in it. No, I I I played a role as a as the richest man in America married to, you know, in a loveless marriage with Gwen Pel was very dark. I'll tell you what I learned. Um, and I could have never known this until I was in the moment. When you make a movie like this particularly a period piece, and you have a great director like Zafy, what he wants to do is create an environment with like 100 extras and you you you we took over the Plaza Hotel from 7 at night to 7:00 in the morning. And I'm just remembering this one sequence we shot all night long.

When you close your eyes before he says action and everything on the table is vintage 52, your clothes are 52, your watch is 52, everybody, the menu is 1952, the art is 52, everything around you is 1952. All of a sudden, you magically transform to 1952. You're there. You're in it. And everybody is in 1952. And it's not you're not acting anymore. You're just there.

You're, just, being, your, character, in, 1952 with everybody else in 1952 and, magic, happens., And, by, the, time, you do the 40th take, you are definitely you know, in the zone because you're doing it on film and they have to move the single camera back and forth and you're there all night long. I remember that day in New York when that sh that day was over. It was a very very important scene which if you see the movie you will definitely remember this scene. Um it's dark. It's dark but I was so wired when I got back to Kasa Chiprianis in New York where we were staying. My wife and I.

It was 700 a.m. and I went upstairs to the restaurant and I said, "Look, I want the scrambled eggs and I want some smoked salmon and I want a 1922 or 2022 bottle of uh Montrech." He said "Sir it's 7:00 in the morning." I said "Not for me, it isn't. I just got back from 1952. I need a bottle of Montrachet." And I called my wife said, "Look, I'm drinking up here." And she said "What are you crazy? It's breakfast." I said "No, I'm just so wired. I'm just so stuck in 52. I got to snap out of it. It's like if you're dyslexic, sometimes the world will shift 180 degrees and you have to shake your head and get back. It snaps back. I was in that kind of a mode. I had to get back to 2025 and I didn't want to go back to 2025.

It, was, so, magical, to, be, in, in, in, the birthplace of entrepreneurship in 1952 in America because that's where the American dream started in Brooklyn back then and that's what the movie is about.

And, so, I, was, I, mean, it, was, emotional, for me. was crazy and damn that mantra was good. That's that's that's how that experience was.

And, it, comes, out, Christmas, Day., I, can't wait. You, got, to, see, it., I, mean,, I, I'm, so proud of the work. I mean, I just dying to see what people think.

Okay,, let's, switch, gears, back, into, your investing in other companies. I learned that you only invest in profitable companies.

That's, not, quite, true., Um the larger investments, that's astute on your part. when if I'm if I'm going to put in 5 10 $15 million, it's into a business model that's proven it's profitable and I'm just negotiating my liquidity, my position on the cap table what I bring to the table, what my team brings. It's a negotiation. That's really the majority of what I do. But I also have a massive, you know, I feel that all of us on Shark Tank have become ambassadors of the American dream.

Mhm., and, and, so, we, invest, in, many, many many startups and my job is to figure out you know which ones to back. But I have learned something about this whole Shark Tank journey that goes to this point. I always thought a decade ago that you know people thought of America our number one export is probably technology or energy. It's not. It's the American dream.

That's, what, we, export. And, and, Shark, Tank's, just, part, of, that whole thing. The number one thing that we export around the world is the idea that you can start with an idea and and change your life forever with it. So that's what Shark Tank's about. But most of my larger investments are, as you suggest, they're in profitable companies. My job is to make them more profitable. But I also do my own startups outside of Shark Tank. Recently, I just did Wonderare um watch insurance for for people that own watches because if you put it on your home package, you may find this out the hard way. Many home package insurance is with a rider for watches or jewelry they give you the depreciated value.

Watches do not depreciate. Rolex goes up in value over time. So, you want to get the replacement price. So, that's what we offer WonderCare. to do that business. I partnered with seasoned professionals on the tech stack of AI to be able to scrape insurance data so we could issue policies through AI. Um wonderful relationships with companies like Chub. You know, I'm I'm I'm one shareholder in it. I think I'm the largest shareholder because I funded it from the beginning, but I I probably won't end up remaining the largest shareholder because I bring a lot of talent and we just hired a new CEO and it's growing. business is growing and so that's from scratch.

Mhm. And, I'm, very, fortunate, as, you, are., I have millions of followers, millions of followers. And they all know I'm a watch guy. So my customer acquisition cost is zero. I just do my own 15-second ads on my own social media. And I say, "Look I'm selling this product. If I use it myself, here's why." And I'm fortunate enough to issue policies without any customer acquisition cost. I don't know anybody else in the insurance industry that has that luck.

So,, you're, bringing, up, a, topic, that, I feel like I talk about on almost every show now, which is creator entrepreneurship. I feel like that is totally the future. Having a personal brand is so important, especially with AI coming out and just the ability that it's like everybody can start a business, but what is actually going to differentiate you? And I think what it is is your ability to create content and grow on social media and be a creator entrepreneur. What are your thoughts about personal brand and the importance of it as an entrepreneur?

You're, more, than, 100%, right., You, are more than 100% right. It's the greatest opportunity this economy has ever offered an entrepreneur. It's extraordinary. But it goes back to something you said earlier storytelling.

Mhm. If, you, don't, have, the, ability, to, tell, a story, you can't do that. Personal brands are built on remarkable authentic, passionate relationships with communities that you're building. People smell a mile away on social media. If you're not authentic, if you're not honest, if you're not telling the truth, you're going to get slaughtered, beyond canled. I mean, so the brands that are working are the ones that say, "Look, here's what I am. Here's what I do. This is the way I see it. You may not agree with me, but I'm always going to be true to what I believe in. And whether it's a product or a service the people that fail at this think that somehow they can attach celebrity to any product and sell more of it. People smell that so far away. The only products I ever associate myself with, I eat my own cooking. I would never ever endorse a product I don't use. ever. I get offered that all the

time. Well, we'll pay you to say this is great. I don't know. It's great. I'm not using it and I never would use it. You know, it's just not what I want. It's not an easy path. But when you start what you have on your if you're good at it and a good storyteller and you're authentic, you get advocates. They become your community. They tell others about how important their relationship with you is.

And, that, is, a, remarkable, outcome. Yeah., It, it, is, the, ultimate, ultimate entrepreneurial experience.

I'm, part, of, this, entrepreneurship, group called Hampton and there's like 10,000 of us in a Slack channel all across America and I'm probably one of the only like real creator entrepreneurs and I find that like I don't relate to them at all. like I don't relate to them at all because I feel like all their problems for me it's like I'm I'm coming out with a new LinkedIn offer that's going to be for small business owners and to sell it like I just have the idea and I'm just going to you know put it online and run a couple webinars and I'll be sold out basically and so like it's just like so simple. I have an idea and I just put it out and you know operationalize it.

Well, that's, because, people, trust, you., They know who you are. I mean it's all these these communities are built on trust. They they're built on a a someone who believes what you said and believes you will deliver what you say you're going to deliver and the experience will be a positive one and if they buy or use the product again a second time they will experience the same they did on the first. That's a brand being built and that's what the whole deal is about. And you can't do that unless you're authentic and you deliver what you said.

It's why the bloom is off the rose on a lot of celebrity endorsements now because they're not being transparent and honest. They don't actually use the product.

I, mean,, you, can't, endorse, 16, products. You possibly can't use them. The, model's, changing., That's, why, you, can emerge as a creator out of nowhere because, you're, authentic, and, all, of a sudden have, you know, 10 million followers that believe you. I think it's f I think it's a great and powerful force, but also has a dark side. Look what happened to Bud Light.

Mhm. They did that themselves. They didn't think about who their customer was and they shot themselves in the foot multiple times. They stored billions of dollars with a market cap. I mean, it was unbelievable. That's the dark side of social media, but shows you the power of it.

Yeah., One, of, my, weaknesses,, I, would, say, is that like I'm not the best at finance, right? So, I have a business partner who does like a lot of my finances. And I know that you mentioned um, one, of the, things, that, you, say, uh, see entrepreneurs fail at is not knowing their numbers.

Yeah,, it's, a, big, problem. So, what, would, you, say, are, the, key metrics that founders, CEOs should be following for their business?

If, you, don't, know, your, numbers,, you better get somebody who does as you've done. You have to have somebody that gives you the dashboard of your business every day. I mark tomarket my business portfolio all positions every day right after 4:00 and I work with my finance team to say okay there's something happened over here something happened over here I see this cash came in this account in this bank what was that about cuz I don't recognize that revenue stream you know every single day I spend maybe 20 minutes just going through the top line of where I'm anticipating revenues coming in from whatever business whether it's a royalty or whether it's a stock that's going public or whatever it every day. And what I find is that keeps me sharp and it keeps me in touch with the eb and flow of revenue and margin and free cash flow.

And so that's what I focus on. If you don't have that skill, you need somebody who has to have that has it because that's a really big problem um if you don't do that. And and I think you know you will fail

if, you, don't, if, you, can't, read. I, saw, that, you, were, just, looking, at, your watch and I noticed you're wearing two of them. Why?

I, This, is, this, is, actually, um, New, York time and this is local time. Uh, so, I, end, my, show, with, two, questions that I ask all of my guests. The first one is what is one actionable thing our young and profiters can do today to become more profitable tomorrow.

Learn, AI., Find, out, which, models, you, can rent for your business cuz there is plenty of product on the market now that will enhance your margins and your productivity. Every single one of my companies now is using AI. most of it primarily for content generation, but they're also using it for all kinds of analytics and data scraping. It's very inexpensive today. Um, every single one of them is using it. And so, if I'm looking at business and they're not using AI, I mean, it's it's not that complicated. It's very easy to adopt it and you will find ways to save money almost immediately. I mean, some of these models you can rent for 129 bucks a month that do incredible things with content. So save yourself a ton on creating content for your social media.

And, what, would, you, say, is, your, secret, to profiting in life and this can go beyond finance and business.

I, would, say, going, back, to, focus, on, the signal, my secret is I'm able to focus on the signal now every day. I know what's signal. I know what's noise. I don't let noise slow me down. And you know that's why they call me the mean shark. That's complete I just tell the truth. But I'm focusing on signal there and I'm determining what's important for me and and the things that that matter for that day that just that day just the three things that day. It's not that complicated. Not next month next year, whatever. It's that day. What do you got that I got to get done? I'm going to get it done. And I do it day after day after day after day. And the more confidence you build and then I'm really into this mantra of getting up in the morning feeling good because the diet and the exercise and the sleep it's such a gamecher. You know that old mantra about you sleep on the sofa, you only get two hours sleep because you're

that amazing entrepreneur. That is such crap. The guys that are winning and even Bezos talks about this. He doesn't make big decisions after noon. He doesn't want to be tired. He he does the sleep thing. He does the diet thing. He does the exercise thing. and he's you want to make those decision. I I can even think last week I was riding the bike. It hit me. I had an idea and boom, I I had had that thing executed by 4 in the afternoon and it's I think it's going to make me a ton of money.

Yeah,, I, love, that., Kevin,, thank, you, so much for your time today. I really appreciate it. Where do you want to send everybody to? I know that you're so visible online, but where do you want to send everybody?

I'm, on, all, the, platforms, at, Kevin, Olry TV. Um come and see me anywhere. I I I love my community and we have a lot of fun together and I love the discourse. I love to get into debate with people. Um because there's always a pro and a con to everything and I think that's what's great about life that we have a great discourse and we you know we we chart the path. I support entrepreneurship in America. We create 72% of the jobs. Um that's my army.

Thank, you, Kevin., You, are, such, a, role model. Thank you for all that you do. I know me and a lot of entrepreneurs really look up to you. Thank you. I appreciate that so much. Take care.

Well,, guys,, this, was, such, an, important interview for me. It was a full circle moment because I've admired Kevin for so long and I grew up watching Shark Tank together with my family. One of the takeaways I found most powerful today was Kevin's signal versus the noise framework that he learned from Steve Jobs. Every single day has three critical tasks that will actually move your business forward. That's your signal. Everything else is noise. The ratio must be 80% signal, 20% noise or less, or else you'll fail. This isn't just productivity advice. It's a complete mindset shift. Stop trying to make everyone happy. Stop wasting times on things that don't matter. You don't need friends in business. You need people who respect you. Kevin also reminded us that getting punched in the face is essential to entrepreneurship.

Every setback teaches you how to pivot smarter. But here's the brutal truth. If your business isn't profitable after 36 months, take it behind the barn and shoot it. Your time is your most valuable asset, especially in your 20s and 30s. Own your failures completely. No excuses about market conditions or competitors. The moment you can smell your own failure and accept it, that's when the real growth begins. And I loved Kevin's emphasis on fueling your body for peak performance. 1 g of protein per pound of body weight, consistent exercise, and 7 hours of quality sleep.

These aren't just wellness tips. They're competitive advantages that sharpen your decision-making when the stakes are highest. Remember that Kevin said "Entreneurship is a disease that never sets you free. But if you have the guts to focus on your signal, own your own setbacks completely, and take care of your mind and body, then you have what it takes to make it through the valley of death and come out the other side victorious." Thank you for listening to this episode of Young and Profiting Podcast. If you listen, learned, and profited from this conversation with the incredible Kevin Olirri, then share it with somebody who needs to hear these hard truths about entrepreneurship. And if you enjoyed this episode and learned something valuable, I'd really appreciate it if you left us a five-star written review on Apple Podcast Spotify, or Casbox. Your support helps more people discover Young and Profiting

and allows us to bring a powerhouse guest like Kevin Olirri on more often. You can also find me on Instagram at Yapwith Hala or LinkedIn by searching my name. It's Hala Taha. And before we wrap up, I want to give an incredible shout out to my guest outreach team for always being on top of their game. Shout out to Hasham for Khan and Joshua for absolutely crushing it and for snagging an incredible guest like Kevin or Liry. Until next time, this is your host Halataha aka the podcast princess signing

Questions about this episode

Who speaks in "Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)"?

Hala Taha (Host), Kevin O'Leary (Guest), Brandon Dawson (Guest), Hasham Khan (Guest), Joshua (Guest).

What is "Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)" about?

Kevin O'Leary emphasizes the importance of personal accountability in entrepreneurship, arguing that founders must take full responsibility for their businesses instead of blaming external factors like market changes or competition. He discusses the critical transition from entrepreneur to leader at the $5 million revenue mark and highlights the need for balance and continuous effort in building…

What is mentioned in this Young and Profiting episode?

45 people, works and ideas are mentioned, including The Learning Company, Mr. Wonderful, Customer Acquisition Cost (CAC), Signal vs noise, American Girl, Ashley Ala. Each one on this page links to its own page with every episode that mentions it.

How long is "Kevin O'Leary: This Rule Built My $4 Billion Empire (Most Entrepreneurs Miss It)"?

The episode runs 1 h 17 min; the transcript is about 14,472 words in 190 timestamped sections.

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About this transcript: the episode's spoken words as captioned on YouTube, split into timestamped sections. Reclip.Me locates every person, work and idea in the text, keeps the time it is first named, and quotes the words around it verbatim. Last updated December 17, 2025.