# Kevin O'Leary: America Loses to China if We Regulate AI

An episode of [Build or Break](https://invisiblenetwork.ai/podcast/6796376545), 3 Sep 2026, 1 h 08 min.

Audio: https://episode.flightcast.com/01M14VVRBBY8DHRCHK4XM5YXCB.mp3

Kevin O'Leary opens up about the $12.9M card he wore to the Oscars, what he did that almost ended his engagement, and the moment his stepfather told him he'd never make it. Before Shark Tank, before "Mr. Wonderful," Kevin O'Leary was a kid getting told by his stepfather that he wasn't good enough to be a photographer. In this episode of Build or Break, Kevin sits down with Daniel Lubetzky for a conversation that goes far past the TV persona — the $12.9M sports card he bought on a hunch (and turned down $21M for), the night he had to tell his fiancée he cheated, firing his best friend in the early days of his first company, and the "signal vs. noise" framework he learned from Steve Jobs that still runs his entire day. You’ve never seen Mr. Wonderful like this. I’VE never seen him like this. This is Kevin without the edit — brutal honesty about business, marriage, grief, and the stepfather he says made him who he is. Thank you for coming, Kevin! https://www.instagram.com/kevinolearytv/ https://www.youtube.com/@kevinoleary https://www.tiktok.com/@kevinolearytv https://x.com/kevinolearytv https://www.linkedin.com/in/kevinolearytv/ Personal site: https://kevinoleary.com O'Leary Ventures: https://olearyventures.com Shark Tank profile: https://sharktankgroup.com/kevin-oleary.html Show Notes: • All images from Kevin’s Instagram page https://www.instagram.com/DanielLubetzky https://www.tiktok.com/@daniellubetzky https://x.com/DanielLubetzky https://www.linkedin.com/in/daniellubetzky https://daniellubetzky.com/ 🙋🏻Become a Builder: https://buildersmovement.org/ Music: Amos Cochran https://www.editscoremusic.com/ Production: Straybird Studios https://www.straybird.studio/ Post Production: Jennell Lewis & Scott Convery Social Media Production: https://www.edits-etc.com/ Build or Break Team: • Executive Producer & Host: Daniel Lubetzky • Executive Producer: Kristin Schneider • Head of Programming & Production: Joel Rubin • Marketing & Communications: Sarah Black • Associate Producer & Social Media: Taylor Larned • Booking & Scheduling: Kayla Rose • Network Relations: Julianna Cohen

## Transcript

[0:00] You're going to go down into the valley of death and have to emerge out of it.
[0:03] I've gone back to his grave in Ireland.
[0:05] It was tough.
[0:06] In Malahi.
[0:07] My brother.
[0:14] What I've learned is it is impossible to make everybody happy.
[0:19] And it's not worth trying to.
[0:21] Sometimes you're led astray, particularly early years of the marriage.
[0:25] He said, no, you're not good enough.
[0:27] You'll never make it.
[0:27] In my kind methodology, there's no room for mediocrity.
[0:31] There's risk.
[0:32] You may burn all that time and not make it.
[0:35] Why don't you diversify...
[0:37] risk through option.
[0:38] I tell my own kids that.
[0:39] And Timothy came out and said, I don't want another ass, I want my ass, because it's gonna be immortalized.
[0:45] And they're sitting there holding a card for an hour.
[0:48] You gotta think there's a person inside that costume who's gonna take a piss.
[0:55] Today's guest on Build or Break is known for telling the cold, hard truth.
[0:59] He's been called brutal, blunt, brilliant, bald, bastard, bully, and yet he is beloved by millions.
[1:09] He has invested in over 80 companies, appeared on one of the most watched business shows in television history for 18 seasons, and built a financial empire out of a philosophy his mom taught him when he was seven years old.
[1:24] I call him El Señor Maravilloso.
[1:27] Others call him Mr.
[1:28] Wonderful.
[1:29] Welcome to the wonderful Kevin O'Leary.
[1:33] Great to be here.
[1:33] Thank you.
[1:33] Thank you for being here.
[1:34] Yeah.
[1:35] I want to cover a lot of ground, some funny stuff, some serious stuff, but I want to start with the most consequential of questions that I could think about.
[1:43] I've been now recording with you eight years ago.
[1:46] on Shark Tank, and I've noticed you shave twice a day.
[1:50] My skin can't even handle once a day, and you do it for many, many days.
[1:55] Is that basically the essence of who you are, a rugged man that can handle it, and I'm a wimp that can't really...
[2:02] I'm a man of routine and when I started shooting this format, Shark Tank's owned by Sony, it was called Dragon's Den way back.
[2:11] I saw the British version.
[2:12] In Canada?
[2:13] Yeah, so the British version was first and then the Canadian was second and Australia, New Zealand, other countries and now over 50 countries.
[2:21] But we started, Robert and I, together on Dragon's Den in Canada.
[2:26] And it was a really, really bootstrap production.
[2:31] We were in a barn, no air conditioning, and it got really hot at noon.
[2:37] Our makeup would be sweating and caked on your face.
[2:41] So I went into the washroom, because it was a toilet back then, that was it in a barn, and washed it off.
[2:47] And I noticed, wow, I've got an afternoon shadow.
[2:51] So I had an electric razor and I shaved it off and I put the makeup back on.
[2:55] And ever since then, which has to be, you know, it's got to be 25 years ago.
[3:02] I've been doing the same thing when we shoot Shark Tank.
[3:04] I just and I also am able to sleep for about 20 minutes during break, which, you know, recharges me for the afternoon.
[3:12] I'm very fortunate to be able to nap in airplanes and limos.
[3:15] And, you know, I'm a big sleep fanatic.
[3:17] You know, you always joke that you're a vampire and never believed it.
[3:20] But yesterday or a day before yesterday when we were doing makeup, I came in to say hello.
[3:25] And you're like asleep while sitting.
[3:27] Like, I'm like, maybe this guy does have something.
[3:30] Well, you know, if you I'm very into longevity these days, I wear an aura ring and I track all of my hours of sleep, how much REM, how much steep.
[3:38] I care about what I eat and all the exercise and everything else.
[3:41] But sleep is the key to longevity actually.
[3:44] People ignore it and they think, oh, I'm an entrepreneur, I gotta work 20 hours a day.
[3:49] I don't invest in people to do that.
[3:51] They fail ultimately.
[3:52] Yeah, my team at T-Series, I talked too long about this topic, so we won't go there, but I had chronic insomnia for 44 years.
[3:59] It's very tough.
[4:00] I only conquered getting good sleep a year and a half ago and it's completely transformed my life.
[4:06] Well, sleep is a billion-dollar-plus, multi-billion-dollar industry now for people, whether it's betting or new technology.
[4:13] We've seen so many deals on Shark Tank that have to do with sleep, too.
[4:16] Yeah, I believe in it, too.
[4:17] Just one more thing before we actually go deeper on Shark Tank.
[4:21] You look so dapper.
[4:23] You're just always looking this good.
[4:25] It's an honest question.
[4:26] When you travel, you travel that elegantly?
[4:29] Yeah, over the last, I don't know, 10 years, I've started to watch others that are very, very successful.
[4:39] And so much of what I do today is present ideas to people, whether it's in business or whether it's on television or shooting a show or recently acting.
[4:52] And you only, it's an old adage, you only get one shot at doing the first impression.
[4:58] And so particularly now when I'm involved in so many political issues, people have a certain expectation of what I'm going to look like.
[5:06] when I arrive somewhere, and most of the time, it's the shark tank outfit, which has been seen hundreds of millions of times.
[5:15] It's the same black suit, black tie, white shirt, skull cufflinks, and the red thing, you know?
[5:22] So I wanna shake it up.
[5:24] I wanna show up looking a little different.
[5:26] And so I've been working with Dolce Cabana, the design team,
[5:31] We have an arrangement.
[5:33] I'm not at that level.
[5:35] I have to pay them to wear their clothes.
[5:37] Yeah, no, the days of free clothing for anybody, unless you're on a movie set where you don't own it, is over.
[5:43] Too bad.
[5:44] Yeah, but let me give you an example.
[5:46] When it came time to walk the red carpet for the Oscars, we had nine Oscar nominations on Marty Supreme.
[5:51] Yeah.
[5:53] Every single fashion house reached out to me and said, look, what are you wearing for the red carpet?
[5:58] And the same thing with jewelry.
[6:01] But they did gift it to you?
[6:03] No, no, no, no.
[6:03] What I said to them, I said, look, let's determine.
[6:06] I chose a jacket, one-of-a-kind jacket, that they were trying to sell for $1.5 million.
[6:14] What?
[6:14] Yeah, it took six months to make it.
[6:16] It was hand-stitched sequin.
[6:18] It was beautiful.
[6:19] But you kept it or you used to be poor?
[6:21] I kept it.
[6:22] I refuse ever to...
[6:24] to wear anything rented, including watches or jewelry.
[6:28] I will not wear something I don't own.
[6:30] But let's talk about fashion for one second.
[6:32] Because for me, a $1 million or anything above $1,000 seems ridiculous.
[6:38] And I have to tell you, I do not understand fashion.
[6:42] And when I'm on Shark Tank, I look
[6:44] Pretty good there, I say so myself, but it's because of Artemis.
[6:46] She dresses me and then I have this cheat where I learned what she did and then I repeat it for the whole year.
[6:53] It's basically my routine.
[6:55] And I find it crazy.
[6:56] I don't understand how one time it's pointy shoes and then I start wearing pointy shoes.
[7:00] Like, no, no, now it's flat shoes.
[7:02] And it's this, like, I almost feel like they're doing it on purpose to keep me confused and keep people buying stuff.
[7:07] You've come into the life of social media.
[7:09] You're on Shark Tank.
[7:10] How you dress, how you look.
[7:12] What you do on major events like the Oscars red carpet stays digital.
[7:18] It's digital in perpetuity.
[7:20] And so that jacket, there was another piece of jewelry that I negotiated with Tiffany on.
[7:26] I'm very much into collecting cards now, baseball and basketball, sports collecting.
[7:32] It's really remarkable because as an asset class, I got into it last August for the first time.
[7:38] I went in with a syndicate to buy a $12.93 million Jordan Kobe dual auto man logo.
[7:46] And so I thought this is crazy.
[7:47] My wife thought it was crazy.
[7:49] We got offered, we paid $12.93 million.
[7:51] We got offered out of a buyer in Japan $21 million for it.
[7:55] I don't have an asset class that outperformed that.
[7:57] And also because the demographic, a lot of men who grew up with that big enough market that it should do better.
[8:04] But also the Asian market, the Chinese market.
[8:07] Basketball has become a global sport, and so baseball is famous too.
[8:12] But anyways, the idea was to wear that card on the Oscars, how to do that.
[8:17] And I sat down with Nicole Weiss at Tiffany.
[8:21] She's the head of high jewelry for LVMH.
[8:23] And I said, let's dream big.
[8:26] The logo for the movie was Dream Big.
[8:29] I said, what can we do?
[8:31] that would be a big splash on the carpet.
[8:34] Could you design a solid gold chain with diamonds and rubies to hang the card in, and I'll wear it with the Dolce?
[8:43] So the design teams worked together, all in LA and New York, Milan, Rome, designing this thing, one of a kind piece, a two-point weight,
[8:55] It was 110 carats, 2.2 pounds.
[8:57] Please tell me you borrowed that one.
[9:00] No.
[9:00] So what we, I said, I'm not borrowing that because they said, look, we'll lend it to you.
[9:04] We'll put it in the museum in New York.
[9:06] I said, no, not doing that.
[9:08] I don't mind putting in the museum.
[9:09] I have to own it.
[9:10] We went through a long negotiation because I knew they'd get so much press from this thing.
[9:15] I've been wearing it all over the world now.
[9:17] It's only one in the world.
[9:18] Then I went to Rolex and said, can you match this?
[9:22] Is there such a thing as a ruby, white gold diamond
[9:27] Rolex.
[9:28] It's mystical.
[9:30] Maybe it exists, maybe it doesn't, it's off catalog.
[9:33] Anyways, they flew it to LA the night before the Oscars and I bought it.
[9:38] But anyways, I wore it.
[9:39] There's a long story, but the presentation was explosive.
[9:44] It went viral.
[9:45] Do you ever feel that
[9:47] I know this is an asset class that you are actually creating value on, but do you ever feel that taking so much time with all those looks takes away from building businesses?
[10:02] I used to think that.
[10:03] I used to believe that.
[10:05] I'm going to tell you a story that I learned 25 years ago.
[10:12] The VC firm that invested in the learning company, the one I sold for 4.2 billion, it was T.H.
[10:19] Lee, it was one of the main capital T.H.
[10:20] Lee, very famous in Boston.
[10:22] And the guy I loved there was Scott Sperling.
[10:24] He's still running it.
[10:25] And Scott said to me after we exited, he said, Kevin, why don't you come over here and we'll set you up, we'll give you a fund and you do it all over again.
[10:35] You start, this time you're an investor.
[10:37] I said, well, that's interesting, Scott.
[10:39] Okay, let's try that.
[10:40] And I started looking at deals, not from the perspective of running them, you know, like you do now.
[10:46] You were an operator.
[10:47] I was an operator.
[10:48] You were very successful.
[10:49] I was very fortunate as well.
[10:51] But now we're not operators.
[10:52] We're investors.
[10:53] We have made the mistakes.
[10:55] That's what I like to say.
[10:56] And now I can see them coming.
[10:58] And so, but here's what he said.
[11:00] He said,
[11:00] He said, look, I got a phone call because I have a Canadian passport.
[11:07] And Canada that year was selling all the digital licenses for the first cable, the movie channels, the dog food channel when that was happening.
[11:16] But you had to be a Canadian to buy the license.
[11:19] So Scott said to me, look, get up there, bid on everything, buy it all.
[11:24] Just buy everything.
[11:26] We don't know which one's going to work.
[11:27] Get up there and buy everything.
[11:29] So I got up there and I started buying everything.
[11:31] I didn't know what the price was.
[11:32] I just bought it.
[11:33] You know, whatever they kept bidding it to.
[11:34] With their backing.
[11:35] Yeah, of course.
[11:36] And...
[11:39] One of the reporters there noticed me and said, listen, can you come on tonight and talk about the auction?
[11:45] Because you're being an absolutely greedy pig.
[11:48] Like, nobody's getting a chance to buy anything.
[11:49] You're buying everything.
[11:51] Her name was Janice Mackey-Fraer.
[11:53] She's very famous now for NBC.
[11:55] She reports from all around the world.
[11:57] We got into a huge fight on television.
[12:01] And she started crying.
[12:04] She was upset.
[12:05] She was upset.
[12:06] I wasn't going to take any shit from her, and I'd never done any television before, so I was just having a conversation with somebody attacking me for buying licenses with money.
[12:15] The phones exploded.
[12:17] And the producer came and said, can you come back tomorrow?
[12:22] That's when you discovered television.
[12:24] Yeah, that's when I discovered television.
[12:25] For real, that was your original?
[12:27] That was the first time.
[12:28] And we're still in touch.
[12:29] Janice Mackey-Ferrer, she's very famous.
[12:31] She's terrific.
[12:32] But that's the moment when you learned so much about- Because I forgot I was on TV.
[12:36] I didn't give a damn.
[12:38] That's when the Cabron Mr.
[12:39] Wonderful was born in some way.
[12:41] Obviously not the name.
[12:41] Yeah, it happened around then.
[12:43] But Scott, I started doing TV and more and more TV.
[12:46] And then Scott said to me,
[12:48] Kevin, you know, in venture capital and private equity, we keep a low demeanor.
[12:53] We stay out of the spotlight.
[12:56] We move in the shadows making investments.
[12:59] We're all uncomfortable with you running around on television everywhere.
[13:03] By now I was on CNN and everything else.
[13:06] And I said, Scott,
[13:09] I'm talking our book every day.
[13:11] I'm getting more and more calls from people because they're seeing me on TV.
[13:15] What are you talking about?
[13:16] He said, no, no, no, no.
[13:17] We're uncomfortable.
[13:18] We're uncomfortable.
[13:19] Today, he wants to get on TV to talk about T.H.
[13:22] Lee.
[13:22] They all do.
[13:23] Everybody, look at all the business cable channels.
[13:26] The change, my whole point about this is
[13:30] No, it doesn't disrupt business.
[13:31] It enhances business.
[13:33] Selling your own personal brand, talking about your vision, getting the opportunity to reach millions of people this way.
[13:41] All around the world, and you're obviously seeing it happen on Shark Tank for you, your brand is expanded, but your brand is also your vision for business.
[13:49] And so I don't see they've completely merged.
[13:53] And I think it's a spectacular way to invest your time.
[13:55] And I probably spend 20 to 30% of my day on television every day.
[13:59] People that watch you on Shark Tank, some people hate you.
[14:01] You play that up for the drama to be the protagonist that's an antagonist.
[14:07] But I've gotten to know you over eight years.
[14:09] I love you.
[14:10] You're an amazing guy.
[14:11] But there is an essence of that cold hard truth, right?
[14:14] You like it like it is.
[14:15] But one of your formative influences was...
[14:18] seeing that confrontation with that news person and seeing that it actually worked on television and seeing, oh wow, let me lean into this, let me be that.
[14:27] And there was an essence of you that had that strong personality that was comfortable saying what needed to be said.
[14:34] My personality, maybe because of me being the son of a Holocaust survivor, I hate confrontation.
[14:42] I can deal with it, as you've seen on the tank or behind.
[14:45] If somebody fucks with me, I will fuck with them twice over.
[14:48] But I don't like it.
[14:50] I don't like...
[14:52] I like to say what needs to be said in a nurturing way, but above all, I like to build bridges.
[14:57] Yeah.
[14:59] And in some ways it's a weakness because sometimes in the tank, somebody needs to hear something and you sometimes are the only one that has the courage to say it.
[15:09] And the rest of us don't have that strength.
[15:11] And you have a brand because you actually just tell it like it is.
[15:15] And so there's nowhere else to go but with that frankness.
[15:18] Yeah, I don't think it's possible.
[15:20] Yeah.
[15:21] to over a long period of time not be authentic because the falsehood leaks out.
[15:29] That's the problem and people sense it right away.
[15:32] What I've learned is it is impossible to make everybody happy and it's not worth trying.
[15:39] So, you know, if you have a direction, you have a vision, you have a strategy, you have a mandate, whatever you want to call it, and you want to do something, if you think it's the right thing to do, whatever it is, you know, then just go do it.
[15:56] And don't spend any energy worrying about everybody that's trying to stop you.
[16:03] Was there something in your life
[16:05] that taught you to be that way?
[16:08] Just like I think that my primary thing is building bridges to prevent what happened to my dad from happening and to others.
[16:16] What made you have the resilience and the thick skin to say, do what I believe I need to be doing and not worry about what others may say?
[16:25] Well, I'd argue that everybody that's an entrepreneur goes through that because no matter what you think when you start that first business, I remember my first business,
[16:34] you're going to be hit by a hammer.
[16:37] Something's gonna happen to you that's brutal.
[16:39] It's you're going to go down into the valley of death and have to emerge out of it.
[16:43] That's every business being startup.
[16:45] Something horrific happens.
[16:47] And that happened to me multiple times in starting my first software company.
[16:51] Wow, was that hard.
[16:52] And I realized in every day, and I live this way myself, during the period you're awake of every day,
[17:01] And it's the same today that it was 30 years ago.
[17:05] Something euphoric is gonna happen.
[17:07] Something catastrophic's gonna happen.
[17:09] You're gonna pick up the phone and it's gonna be a disaster.
[17:12] And then 10 minutes later, it's, oh, somebody called to buy, or you're the control shareholder in this business and they want to buy it for 200 million cash.
[17:20] That happened to me yesterday while we're shooting Shark Tank.
[17:23] You know, it just happens.
[17:25] And I've learned now, the answer is
[17:29] the concept of signal versus noise, and I've talked about this a lot.
[17:35] All day long, there's the important things coming at you, and you have to be able to determine, does that matter, is that signal, or is that noise?
[17:45] adversaries firing at you is noise because it distracts you from what you need to get done.
[17:51] You're always gonna have somebody pissed off about something no matter what you're doing.
[17:55] They don't agree with you, they wanna stop you, they're trying to throw whatever it is at you.
[18:01] But if you engage in that, that's noise.
[18:05] It has nothing to do with your goal.
[18:09] And this is...
[18:11] I learned this from Steve Jobs.
[18:12] I've talked about this so much because it was a gift he gave me, 92 or something, I don't remember when.
[18:18] During the day you only need to get three things done that are important each day.
[18:22] Not the big vision, just three things done.
[18:26] You have to do those first.
[18:28] Anything that stops you from getting the three things done is noise.
[18:31] So your signal to noise ratio according to jobs has to be 80% signal, 20% noise.
[18:37] Noise is when somebody wants to have small talk with you or talk about a show they saw yesterday or a phone call from an aunt or something.
[18:44] I mean, you gotta take them.
[18:46] He was 80%.
[18:47] And because he was 80%, he was extremely difficult to work with.
[18:53] He was tough.
[18:55] And he was brutal.
[18:56] And he was not a nice guy.
[18:58] I mean, but look at what he achieved.
[19:01] And I've only seen one other guy that has a higher ratio, Elon Musk.
[19:06] I've been with him at Mark Burnett's home when he did Shark Tank Christmas parties.
[19:14] The minute he thinks he's in a conversation with three people, four people, that he's getting no value out of it, he just walks away.
[19:20] He just doesn't want to waste his time and look at what he's achieved.
[19:23] So this idea of signal to noise is going to make you a difficult person.
[19:30] And it has.
[19:31] It has.
[19:31] That's why I have so many critics.
[19:33] You know, he doesn't care about this, he doesn't care about that.
[19:35] I don't care because it's noise.
[19:38] It just doesn't matter to me.
[19:41] And so if it doesn't matter to me, why should I put any energy into it at all?
[19:47] Earlier you talked about how you had major setbacks with your software company.
[19:52] Can you talk to us a little bit about, give us a story of one of the worst setbacks and how you handled it?
[19:59] Because you talk to entrepreneurs in Shark Tank all the time about taking the tough decisions.
[20:03] Did you ever...
[20:05] have so much pain that you wonder whether it made sense for you to be doing what you were doing?
[20:10] And how did you handle it?
[20:12] Yeah, I did.
[20:12] And I think every entrepreneur has.
[20:14] I think the first thing... You've cried?
[20:16] Oh, yeah.
[20:16] I mean, I think the...
[20:19] I remember the early days of Softkey Software Products was my first company.
[20:24] And that emerged in the learning company.
[20:26] That's what eventually was acquired years later.
[20:29] But
[20:30] You know, you go through the startup phase, usually with a friend that you start a business with, and you make the assumption that they have executional skills.
[20:41] You make the assumption that, you know, you start with 10,000 in sales, then a million in sales, then five million in sales.
[20:52] The problem is you can't, the business itself,
[20:59] doesn't have any tolerance for friendship versus executional skills.
[21:05] You can't offset a lack of executional skills with friendship.
[21:12] friendship, and you have to make the tough decisions.
[21:15] Most of the people I started with I fired because they couldn't cut it.
[21:20] What was the first time when you had to do it and how did you feel and how did you handle it?
[21:24] It was brutal.
[21:25] Well, I remember sitting on the steps of a home we'd rented to use as an office.
[21:29] We were doing, writing software code in there 24 hours a day and I just, I realized this is the wrong guy.
[21:36] He can't do it.
[21:37] And I have a decision to make.
[21:40] all the other employees are looking at me and saying, I'm willing to follow you into the valley of death because I think you know what you're doing.
[21:48] So you have a responsibility.
[21:50] Then I thought about the thousands and thousands of customers we had now in schools and teachers, teaching kids reading and math skills.
[21:58] You know, Rita Rabbit, Carmen Sandiego, Oregon Trail, these are the titles we were developing.
[22:03] And I thought to myself, who is my master?
[22:07] Like who am I reporting to?
[22:11] you know, trying to keep inefficiency in the business, even though everybody around me knows this guy has to go.
[22:16] And that's when I realized, wow, I have to do the right thing.
[22:20] And I had to whack him.
[22:22] And we have a relationship today, but it has forever changed.
[22:27] There's nothing, you know, I draw the analogy to marriage because everybody, you know, goes through this.
[22:33] When you fall in love, you know, you're dating and you fall in love.
[22:36] It's euphoric.
[22:37] It's fantastic.
[22:38] You can't beat it.
[22:39] There's nothing like it.
[22:40] And a lot of people never stay in a relationship because they want that euphoria over and over again.
[22:44] You know, they're serial daters or marriage or whatever it is.
[22:47] But when you get married...
[22:51] and reality sets in about how hard it is to maintain a marriage, it's not easy, sometimes you're led astray, particularly early years of the marriage.
[23:02] Astray as in?
[23:03] You cheat.
[23:04] You're out on a business meeting somewhere, you sleep with somebody else.
[23:07] That happened to you?
[23:09] Yes, it did happen to me.
[23:12] And you have to make a decision.
[23:16] Do you get up that morning and tell the truth?
[23:19] Or do you hide it saying they'll never find out about it?
[23:22] Now here's your dilemma.
[23:25] If you call and say, look, I did something horrible last night.
[23:28] And at this point I wasn't married yet, I'd been dating somebody seriously and we were on our way to.
[23:38] And I said, I thought to myself, I felt guilty and I had a hangover and all that stuff.
[23:43] If I immediately call her,
[23:46] tell her what I did, is that the right thing to do?
[23:51] Is it the right thing to do because I told the truth?
[23:54] And that, because you think you can hide it, but one day you'll get caught.
[23:58] I made the decision to call her, and it was brutal.
[24:03] It was tough, and I was out of town, so I had, you know, it was tough.
[24:07] I said, look, I, you know,
[24:09] This is what happened, I'm sorry, I'm gonna try like hell for that never to happen again because I value our relationship so much.
[24:19] The other way to do it is tuck it away, forget about it.
[24:25] But in the long run, you're going to get caught.
[24:27] Something's going to come out.
[24:28] I don't understand the analogy of that situation.
[24:30] Well, I'm going to tell you what it is.
[24:32] Telling the truth, the brutal honesty of why you're letting somebody go is actually the beginning of the healing.
[24:41] First of all, I'm 100% in agreement with you that transparency and truth sets you free.
[24:46] And by the way, when you don't do that, you make it worse.
[24:49] Like we've had situations where we didn't want to be mean to person X and we told them, it's not you, it's me.
[24:56] And guess what?
[24:57] And they hate you.
[24:58] I was like, well, why are you letting me go?
[24:59] So sometimes being like, look, you know, this is not working.
[25:02] This is not working.
[25:03] This is not working.
[25:04] It's not working.
[25:05] It cannot work for kind because of these issues.
[25:08] We want to wish you the best, but you're not meant to be here for this, this, and these reasons.
[25:13] I think all of us as humans want fairness.
[25:15] And if you're providing the right rationale and the fairness, the person can actually handle it better than if you bullshit your way through.
[25:23] No, it's not you.
[25:24] It's just us.
[25:24] We're restructuring.
[25:25] All these bullshit answers that lawyers teach us, like, oh, we're restructuring.
[25:29] It's not about you.
[25:29] It's about the... At the end of the day, the person resents you more when you're not being truthful.
[25:35] That said, I also find that in the corporate environment, these things like fire people, like Trump, like in The Apprentices, like you're fired.
[25:46] For me, it's so suboptimal relative to, as long as a person's not stealing, cheating, something horrible, if they are, then kick them out.
[25:56] report them to the police.
[25:57] But if they're well-meaning people that have a good faith instinct, you provide the truth, you give them a chance to fix it, and if they don't, you find a way to part ways in a way that sets them up and you up for success.
[26:10] Like for example, with my team members, we have like this crazy agreement that if they wanna leave, they need to give me two years notice.
[26:19] And if I wanna make a change, I need to give them one year's notice.
[26:23] And there's a reason for the two years and the one years because they have to be responsible for their transition.
[26:28] But people almost never...
[26:31] I've never heard of that before.
[26:33] Two years.
[26:33] It's a gentleman's agreement, but it's for the highest level relationships.
[26:37] For people that I trust, almost like a marriage relationship, it's a true partnership.
[26:42] But even at kind, even for early team members, junior team members, we have a 60-day notice.
[26:48] And there was...
[26:49] If you wouldn't give your 60 days...
[26:51] you'd lose your stock options, which were worth millions.
[26:54] That's written in the contract.
[26:55] That's written in the contract.
[26:56] But by the inverse, we were not unfair.
[26:58] If you gave those 60 days, we treated you like the team member through the very, very last day, and we positioned you for success.
[27:07] We were references to you.
[27:09] We helped you.
[27:10] Because if somebody wants to leave to go study or they want to go for another job, why hide it?
[27:16] Why not be transparent and be partners than anything?
[27:19] Those 60 days, you have the opportunity to look for a person, for this person who was a good team member to replace themselves and train them to pass the baton better and vice versa.
[27:27] As long as there's good faith on both sides.
[27:29] And obviously, it's a very high functioning culture where you trust each other.
[27:33] You have good communication.
[27:34] What do you think about that?
[27:36] In any organization, as it grows, and I've learned this lesson a long time ago.
[27:41] Let's say you start with 10 people in your organization.
[27:45] And after two years, it's evident that out of those 10, three have extraordinary executional skills.
[27:54] It's about the right ratio.
[27:56] And seven are okay, but just okay.
[28:01] So you have a dilemma, and you've undoubtedly faced this.
[28:05] Do you start compensating the ones that are extraordinary performers significantly more than the mediocrity?
[28:13] In my kind methodology, there is no room for mediocrity.
[28:17] The danger is that if you tolerate mediocrity,
[28:20] you're going to move down to that average because the excellent people are going to leave.
[28:25] The mediocre people are never going to leave.
[28:27] They're going to always stay.
[28:28] Nobody wants to hire them.
[28:29] They don't want to leave.
[28:30] And eventually you're in a land of mediocrity and then you do not achieve the potential of your company around.
[28:36] So you have to look for the number six performing people.
[28:38] Yeah.
[28:39] Nine or tens, you have to invest in to keep them there always and always empower them and strengthen them.
[28:44] It's very, very hard to do.
[28:46] Seven and eights, you need to try to cultivate to become nines or tens.
[28:50] Sixes are the trickiest because people are performing at six.
[28:53] They're not causing any harm.
[28:54] Can a six get to a nine is the question.
[28:56] No, a six, in my framework, a six cannot...
[29:00] If it's a seven, you have to help drive them to an eight.
[29:05] But if it's a six, it's like...
[29:07] Mediocrity in them.
[29:08] By the way, this is different from what John Leahy, who was my amazing president of that kind.
[29:16] Without him, I would have not achieved what I achieved that kind.
[29:19] But John Leahy taught me about steady eddies.
[29:22] Do you know about steady eddies?
[29:24] Like these are people... That's very different from being a six.
[29:27] These are people that are never going to...
[29:29] be hungry to become the CEO, but they're doing their job well.
[29:35] But a steady ed is essential in an organization, because you cannot have a hundred Mr. Wonderfuls in an organization.
[29:42] You kill each other.
[29:43] You have to have people that are striving for excellence, and they're hungry and whatever, and you have to have people that are happy with their lot, but they're doing what they do very well.
[29:53] Yeah, I think an army of steady eddies with good leadership is a great business, and I get that.
[29:58] But sometimes it takes a period of time to determine what is the strengths and what are the weaknesses of these people.
[30:08] And some of them have flaws.
[30:10] They're just, for whatever reason,
[30:14] it's not worth the energy to try and fix them because they're broken.
[30:18] But within an organization, an entrepreneurial organization, I look at sort of the one to five million is the startup,
[30:27] Very hard.
[30:28] Very hard.
[30:29] Getting the first million in sales is almost impossible.
[30:31] Then, you know, from one to five, really hard.
[30:35] And then when you hit five, all of a sudden you're forced to team build.
[30:41] You have to start hiring people and you're going to find out about yourself.
[30:43] Do you have execution skills to manage people?
[30:46] And that's going to take you from five to 10 million.
[30:50] And I argue to the students I teach, the journey from 10 to 50 is much easier than the journey from one to five or one to 10.
[30:59] Because by then you've proven to yourself you know how to hire, fire, manage, build teams, everything else.
[31:05] The journey from 50 to 500 I found very easy.
[31:09] I wanna do a little bit of a pivot to just ask for,
[31:15] Advice from you.
[31:16] Sure.
[31:17] Like, give us some tips on a couple different things where you're best at.
[31:22] Like, what are some of the areas where... Let's start with Shark Tank.
[31:26] Yeah.
[31:27] For any entrepreneur that wants to go, for me as a...
[31:31] Char criticized me.
[31:33] Tell me what you've observed.
[31:34] It's like, Daniel, honestly, you suck at this.
[31:36] You need to do this better.
[31:38] I don't even understand how you do what you do.
[31:40] Like sometimes you're so witty and so fast.
[31:44] There was that one example that you were, you make me laugh out loud.
[31:48] Do you ever think about these lines?
[31:50] So they really, really authentically just come to you so quickly.
[31:52] I think the way of what I learned even way back having been on television for all these years is,
[31:59] You have to get to a place where you don't see the cameras, where you are not, this is what I learned in doing Marty Supreme, I've never acted before, but I figured to myself,
[32:13] if you just put me in a room where it's 1952 and the tablecloth is 1952, the menus are, the clothes I'm wearing, everybody's dressed like 1952, then I must be in 1952.
[32:25] And forget about the cameras.
[32:27] Why not just read the room and...
[32:30] Be in the moment.
[32:32] And I think that's what television is all about, is about being in the moment, that moment.
[32:37] Not calculating anything, just saying, here we are having this discussion about this topic.
[32:42] I don't see any cameras, I don't see any lights.
[32:45] There's a bunch of guys sitting here talking about someone's business, which we do all day long in Shark Tank.
[32:51] If you get to a place like that, you'll be in harmony with,
[32:56] you know, the room.
[32:57] You'll be in a mode of great creativity, I think.
[33:02] But if you're, you know, calculating or you're reading your notes or you're trying to remember what you thought you would want to say in a moment like this, that doesn't work.
[33:13] It's not authentic anymore.
[33:15] And the audience can smell that bullshit on my mind.
[33:18] I remember the one where you made me laugh out loud.
[33:21] There was one character that was in a costume.
[33:27] Somebody gave some offer and you said, this character's peeing in their pants.
[33:30] But the way you said it, I laughed out loud.
[33:33] Like, did that just come to you?
[33:35] You know, every time they bring somebody and dress them as a mascot, and, you know, the pictures can be an hour long, and they're sitting there holding a card for an hour.
[33:45] You've got to think there's a person inside that costume who's going to take a piss.
[33:50] I mean, it's just...
[33:51] I remember once where they had these guys that came out, and they stood...
[33:58] like solid and they locked their knees and one of them passed out.
[34:02] I tried to run from my seat, jump over the table to catch his head.
[34:07] Because I watched it.
[34:08] It was like slow motion.
[34:10] There's a phenomenon for drummers in football games where if they stand and they lock their knees for more than 11 minutes, the blood doesn't get to their head and they pass out.
[34:20] That's how the body protects itself.
[34:21] It makes it crumble so the blood can start moving again.
[34:24] And so I didn't know this until the medical... Until you learned it.
[34:27] On Shark Tank, his head hit the cement.
[34:32] Nobody could get there on time.
[34:33] He just...
[34:34] I watched him fall like a tree.
[34:36] Whoosh.
[34:37] And of course, we took a break, the medical guys came in, we didn't tape that episode.
[34:44] No, they never, they decided
[34:48] Was there liability?
[34:49] You know, you can imagine.
[34:50] Don't you think that there's a lot of content in those troves that should be one day...
[34:55] I mean, I find it fascinating how inefficient... You're right.
[34:59] There's tens of thousands of companies that apply.
[35:02] Only about 160 kind of get selected, of which maybe only, let's say, depending on the season, 100 film, but only maybe 60 or 80 actually air.
[35:14] And then out of the ones that air...
[35:18] 75 or 80% of the content is never seen.
[35:20] There should be a bloopers channel or something.
[35:23] It gets better because there's AI tools now that can actually analyze the video.
[35:28] This is just in the last nine months where you could take all of the content ever shot on Shark Tank.
[35:35] And in a matter of hours, it would pull together incredible moments of TV that have never been seen.
[35:41] and it would just give you an index of it.
[35:44] What are some of your organizational tools for?
[35:46] You have so many companies.
[35:48] You have somebody, how do you organize yourself and your team?
[35:51] When we create a new business, as we're doing now with data center development, that is O'Leary Digital.
[35:55] Brand new company, new CEO, Paul Polangian.
[35:58] He's hired a whole bunch of people.
[36:00] He's raised money for it.
[36:02] And so he's operating that business and he and I check in maybe once a day.
[36:08] And we do a lot of stuff in sync about meeting with politicians and going to Washington and all that stuff.
[36:14] And I have lobbyists for that firm, but it's run by a CEO.
[36:17] It's an end.
[36:19] You hire a champion for whatever it is, and it's to be somebody that wakes up in the morning, goes to sleep at night, who's best in the world, at running it, and then you empower them.
[36:28] Do you have a holding- But I not only empower them, that business is 30%.
[36:33] When we created that company, I said, okay, you're gonna be the guy.
[36:37] What's our deal?
[36:38] What's our deal?
[36:39] Because I want you to have skin in the game.
[36:41] I want you to be at risk.
[36:42] They're a partner.
[36:43] Yeah, you're a partner, you're not an employee.
[36:45] So I'm the largest shareholder, but he owns a huge piece.
[36:48] And every time he brings in someone, we equally take the dilution.
[36:52] So he feels the pain.
[36:55] Oh, he's part of the... Yeah, so we started at 70, 30.
[36:58] I bet you he's down to 24 and I'm probably...
[37:01] So he has to consciously decide, is it worth it to bring this person?
[37:05] I never say... Kevin will be deluded more, but I'll be deluded too.
[37:08] Yeah, and that's the only way to do it because if you don't do that, you end up getting... You're not taking risk in bringing people in.
[37:14] The other format that exists is that you hire the CEO, they get their stock option, everybody else gets their stock options, and there's a stock option pool that the CEO does not have to, quote unquote, suffer from or be deleting.
[37:26] Yeah, I don't believe in that model.
[37:27] I like your model.
[37:28] Yeah.
[37:28] But is there O'Leary Enterprises that – is there somebody in – only you there?
[37:34] Yeah.
[37:36] Are each of these entities completely separate from the other?
[37:39] There are many entities, but the mothership is O'Leary Productions.
[37:45] And it exists in multiple countries.
[37:48] I'm 100% shareholder of that.
[37:50] But that's lean and mean, right?
[37:52] It's very lean and mean.
[37:53] How many people do you have there?
[37:55] 14.
[37:56] 14.
[37:57] And what's like legal?
[37:58] What do you... Legal, accounting.
[38:00] It's more corporate because it also owns rights to IP of stuff that we own and brands that we own.
[38:13] But what I've been doing lately, because I think maybe it's a lot to do with technology...
[38:19] Let's say, for example, accounting, which is important, and compliance.
[38:24] These are important because I operate in many...
[38:27] I have positions in many public companies.
[38:29] I've started them as startups.
[38:32] They're now listed.
[38:33] And one of them, Bid Zero, just went public on June 9th.
[38:36] That's my data center company in Norway and Finland.
[38:40] That started...
[38:41] You know, like you and I right now.
[38:43] That started six years ago, two guys talking, saying, the cheapest power in the world is in Norway and Finland.
[38:50] Why don't we just bet on power?
[38:53] Why don't we just go buy land with... Because of hydro or because of the oil or both?
[38:57] No, because they have hydro and they have nuclear power.
[39:00] So the cheapest on earth is one cent a kilowatt hour in Saudi Arabia.
[39:05] But there's stability issues in that region for data centers.
[39:07] So my thinking was with my partners, there were four of us.
[39:12] And this woman approached me and said, look, I worked for one of the top accounting firms and I'm splitting away and I'm going to create a service providing platform.
[39:25] Why don't you let me do all of your bookkeeping and accounting and pay me to be the HR for all accounting?
[39:34] I hire, I fire, I deliver your reports when you want, I design anything you want, and I build a team just for you and your company.
[39:47] I thought, damn, that's interesting because, you know, I have to manage the HR of all the accounting people that are doing it.
[39:55] And let's say for example, WonderCare, my watch insurance company.
[39:58] there comes a point where I'm not the control shareholder.
[40:01] I hire a CEO, we raise money, other partners, and all of a sudden I'm under 50%.
[40:06] Yet it's sitting inside of my holding company.
[40:08] I want it to be like a child graduating from college.
[40:11] It's gotta go on its own.
[40:12] But then I, so now I'm using all these outside entities as service providers for these breakaways.
[40:19] It's a new model, it lets me be much leaner
[40:22] pay much more to the few people that are left.
[40:24] What do you do, for example, with technology?
[40:26] Do you have someone that's like insane trying to help all the portfolio companies or each of the portfolio companies needs to figure out their way?
[40:34] Yeah, I tried both ways.
[40:35] I've tried both ways.
[40:36] I've heard that a lot.
[40:37] Centralized IT, it doesn't work.
[40:40] You have to let each company find their person or service provider and operate.
[40:47] Because let me give you an example.
[40:49] You know, AI, technology.
[40:51] Do you use ChatGPT?
[40:54] Do you use Claude, whatever?
[40:56] So I finally said we were using so many tokens.
[40:59] It was our number one growing expense on the income statement for my holdco.
[41:03] All the AI costs.
[41:05] And so I said to the team, okay, everybody, I'm gonna be democratic.
[41:08] I'm taking my vote out.
[41:10] You guys decide, choose one platform, and we're going to buy an enterprise license.
[41:15] We're going to negotiate for an enterprise license because we were spending hundreds of thousands of dollars a month.
[41:22] So they chose Claude.
[41:24] I'd never used it.
[41:26] I had to relearn it, and now I'm a Claude user.
[41:30] But we have an enterprise license.
[41:31] We cut our cost to 30%.
[41:33] And so other companies are coming to me saying, what are you using?
[41:36] I'm saying, why don't we do a buying cooperative for these technologies?
[41:41] So in cases like that in the new world, I think cooperatives are gonna start.
[41:46] Television advertising, maybe I spent five million a month in the different companies.
[41:51] I'm now buying remnant cable collectively.
[41:54] So there's ways to have the idea of like a Japanese philosophy of cooperation with competitors to save costs.
[42:04] And so, and I learned this from Switzerland too.
[42:06] The Swiss do a lot of interesting things across pharmaceuticals where they compete with each other, but they also aggregate for buying services or hiring people as apprentices.
[42:16] So, you know, cooperation is a new word in my...
[42:21] lexicon of things I do.
[42:23] Something that I don't think enough people understand about you is you truly are very knowledgeable.
[42:31] And you're a man of the world.
[42:32] You're talking about Japan, the Emirates, Saudi Arabia, Norway, Finland, United States, Canada.
[42:39] And I seem to recall that you told me that you...
[42:45] lived in a lot of countries as a kid.
[42:48] Can you remind us?
[42:49] How did you develop this knowledge base?
[42:52] So what happened when I was very young, my dad died when he was 37, my biological Irish father married to my Lebanese mother and my mother remarried.
[43:01] How old were you?
[43:02] I think I was nine years old.
[43:05] And so we moved to Champaign-Urbana, Illinois where the University of Illinois is because my stepfather,
[43:12] was graduating out of engineering and management science at the time.
[43:17] It wasn't called an MBA.
[43:19] And he went to work for the ILO, the International Labor Organization, as an expert in productivity.
[43:25] And his mandate was to move every 24 months to different countries.
[43:28] So he started in Cambodia, Tunisia, Ethiopia, Cyprus.
[43:31] I thought...
[43:32] This was how everybody lived.
[43:34] So, you know, I was living in new countries.
[43:37] I met Haile Selassie.
[43:39] I met, you know, Paul Pott.
[43:40] I met Sanuk.
[43:41] You know, I met them all.
[43:43] I mean, all these people, because as an expat in a country, you'd be working with the government or whatever.
[43:48] I remember it being a cocktail party with Paul Pott.
[43:51] The guy that went crazy and killed everybody.
[43:53] So you're born in Montreal?
[43:55] Yeah.
[43:55] At nine, start traveling like crazy.
[43:59] I just moved every two years.
[44:01] And did that teach you to go bridges, to connect with people?
[44:05] Yeah, I'm also learning the culture, you know, the philosophy of the French because they colonized Cambodia.
[44:13] Japan is completely different in the zen way they live.
[44:17] It's just sort of, and so all of these, in Germany is different, France is different, England is different.
[44:22] But I'm very comfortable going anywhere in the world now.
[44:25] And as a kid, you said your mom was
[44:28] Lebanese.
[44:29] But I feel like the Lebanese entrepreneurial spirit is insane.
[44:34] In Mexico, the richest person in Mexico and among the richest in the world is a Lebanese Mexican.
[44:40] And the Lebanese community in Mexico that I grew up with, they're incredible business people.
[44:44] And that's how... And then also in New York, I mean, there's something in the Lebanese DNA.
[44:48] They're very, very good merchants.
[44:50] You go look at...
[44:51] They're big in real estate.
[44:52] Any city they go...
[44:53] Do you think that in some way, either DNA or mom?
[44:57] What was the thing that you said that your mom taught you about?
[45:01] She basically said, because she was very worried after being divorced from Terry, my father, about financial independence, she never after that experience ever let anybody
[45:16] tell her what to do with her money.
[45:17] She kept it sequestered for herself, and she would take 20% of it.
[45:21] Back then, they paid them in cash each week.
[45:23] She worked for her father in a company called Kitty's Togs that made winter clothing for children.
[45:28] When she got paid, she took 20% of her salary and invested in stocks that paid dividends in the S&P 500 and telco bonds.
[45:36] which were paying 7% back then for as long as five to seven years.
[45:40] And her philosophy was, I'm only going to spend the interest or the dividend.
[45:44] I'm never going to touch the principal.
[45:46] And during the 50-plus years of that portfolio that she kept it secret, when she passed away, I became the executor.
[45:54] I'm the older brother.
[45:55] I couldn't believe what she'd amassed.
[45:58] I mean, if you...
[46:00] If you just put a little bit aside when you're in your 20s and stick it in the stock market and forget about it, you can't believe what you end up with.
[46:09] It compounds at 8% to 9% a year, sometimes 12%.
[46:12] You just don't know.
[46:13] The years go up and down through the market, but you should not bet against the North American economy.
[46:19] Do you miss your mom?
[46:20] Oh, of course.
[46:21] I mean, who doesn't?
[46:22] So you said around the ages of nine, earlier you said you were dyslexic.
[46:27] Yeah.
[46:27] And...
[46:28] your dad passed away and your stepfather took in, but you had already, she had already divorced your father.
[46:35] Yeah, she, she, but she never, she stuck with her, her second husband for the rest of her life.
[46:40] And he stopped.
[46:40] But were you close to your biological father or no?
[46:43] I was, he was a difficult man.
[46:46] He was, I probably have some of his traits.
[46:48] You know, he was probably an alcoholic, I don't know.
[46:52] He was abusive to my mother.
[46:54] There's no question about that's why they got divorced.
[46:56] He was also very.
[46:58] No, he never, I don't mean abusive physically.
[47:00] I mean, he was mentally abusive.
[47:03] I'm just telling the truth here.
[47:04] And he was very kind to my brother and I, but being in a divorce, a divorce is extremely tough on kids.
[47:12] You don't know how it affects them long term, but he didn't last long.
[47:16] He got divorced and then he died.
[47:18] And back then they called it thrombosis.
[47:22] We don't know what happened.
[47:23] How do you think that impacted you?
[47:24] I don't know, but what happened was he was pursuing to get control of my brother and I away from my mother.
[47:35] And in Quebec, in Montreal, it's Napoleonic law, so it favors the man.
[47:40] And so he wanted to get, you know, basically wanted us to live with him.
[47:44] Were you scared of that?
[47:46] Well, I didn't know what was happening.
[47:47] So my mother decided to get on an airplane with the two of us and start going to cities like Stockholm, Geneva, Zurich, Paris, every two weeks moving from hotel to hotel so Terry couldn't find us.
[48:02] And you didn't quite understand what it was.
[48:03] I didn't want, I don't understand.
[48:04] going on my brother so I I was probably six my brother was four or five I can't remember how old he was but we would wake up in hotels in different cities every week but were you having fun or were you traumatized for me no no for me I was having fun I was just wondering why we're moving around so much but there was something going on in her yeah she was scared out of her mind that you know um he he the judge was going to
[48:28] And they were actually on the way to court when he died.
[48:31] He didn't make it one morning.
[48:33] He was dead in his apartment.
[48:34] That's when that whole thing ended.
[48:36] I've seen, you know, it was tough because it was so traumatic and, you know, so difficult for her.
[48:43] She just sat us down one day, said, look, your father passed away.
[48:45] And we didn't know what that meant.
[48:47] So I've gone back to his grave in Ireland.
[48:50] It was tough in Malahi with my brother.
[49:01] Thank you.
[49:03] Very tough.
[49:04] The thing was in disrepair.
[49:07] And so my brother and I are gonna restore it.
[49:09] We're going to the city.
[49:10] And I've talked to the Irish ambassador in Washington to help me do this because it's very hard to go to a historic land site and make modifications because it's in a castle.
[49:21] So we're gonna restore his grave.
[49:24] Well, what's interesting from what you're saying is your stepfather stepped in, you lived an incredible life.
[49:31] Those early years were filled with complex feelings, which sounds like he loved you and treated you guys well, but he was difficult with your mom and you guys were... And yet you're going back every few years to Ireland.
[49:43] I don't think I'd be the person I am today with Terry.
[49:48] I don't think that would have been the outcome.
[49:49] But my original father.
[49:50] But then why do you go back to Ireland?
[49:52] Well, I think, you know.
[49:54] It's still at the end.
[49:55] Yes, I still remember him.
[49:56] You know, this topic is difficult because I have such allegiance to my stepfather, who's 96.
[50:04] And this year, I'm getting the whole family together.
[50:06] I'm sending planes around to pick everybody up.
[50:08] He will not get on a commercial aircraft.
[50:11] 96 years old, he's not going through customs.
[50:12] Where does he live?
[50:14] He lives in Geneva.
[50:15] He's Swiss.
[50:16] He's now a Swiss citizen.
[50:17] Now, my mother lived there for...
[50:18] Listen, he has a home overlooking Lake Geneva that's beautiful.
[50:23] French-Sguisse?
[50:23] Yeah, it's beautiful.
[50:25] And so she lived there, too.
[50:26] Georgette lived there.
[50:27] And over time...
[50:29] They really loved being Swiss.
[50:32] She became a Swiss citizen too.
[50:34] I think my brother and I are the oldest men in history to be adopted in Switzerland.
[50:41] Do you realize you and I have a very strong connection with Switzerland?
[50:44] Yeah.
[50:44] Like my grandfather,
[50:47] survived the Holocaust, went to Mexico, built a business with my dad, duty-free business in the watch business.
[50:55] I don't know if you remember that.
[50:56] Yeah, yeah, the Rolex dealership.
[50:57] And then my grandfather moved to Switzerland, and he's buried in Switzerland.
[51:03] That's fascinating.
[51:03] Very rare.
[51:04] Yeah.
[51:05] I mean, the Swiss are very protective of every inch of their soil.
[51:09] And I have a very romantic connection to Switzerland because I used to accompany my dad to the watch fairs because he eventually got the concessions for duty-free from not just Rollins.
[51:19] That was in the city of Bern you first went to.
[51:21] Yeah, that's now moved to Geneva.
[51:23] It's called Watches in Wonder.
[51:24] I go every year.
[51:25] And do you think part of why you're so in love with watches is because of your stepfather?
[51:30] Undoubtedly, because I bought my first watch in the 70s, the Moon watch, the one that was designed to go into space.
[51:38] It wasn't designed to go into space, it went to space.
[51:40] That's my first watch, I still have it.
[51:42] I have many, many watches now.
[51:43] But they're very emotional because you remember your time of your life when you get them.
[51:47] And I think for men, it's one of the pieces of jewelry that they can get, and I wear two.
[51:52] And these are very rare pieces.
[51:54] I wear two, and I have extraordinary watches now.
[51:57] Did you step that and know how much it impacted you?
[52:00] Yeah, we still talk about it.
[52:01] In fact, I took him to the F.P.
[52:03] Journe factory to meet F.P.
[52:05] Journe and the team in Geneva.
[52:08] And he's met Simon Britt, who's making... Simon Britt is one of the hottest watchmakers in the world right now.
[52:14] What were some of the things that he imparted on you?
[52:18] You said you would not be where you're at today without him.
[52:21] And if your dad had...
[52:24] Being that and raised you would have been a very different outcome for you.
[52:28] What did your stepfather do?
[52:30] I'll tell you, that's a great question because I remember in high school in Ottawa, I was in high school in Ottawa at this point, I said, look, I want to be a photographer.
[52:40] That's my career.
[52:41] I want to be a photographer because I was part of the, you know, I was developing my own film.
[52:45] I was shooting and I still have those images actually.
[52:49] He said, no, you're not good enough.
[52:50] You'll never make it.
[52:54] is to get option value for your career.
[52:56] And I suggest what you do is finish high school and try and get into college because your marks are such shit.
[53:03] Like, you know, because they weren't that great, you know.
[53:06] And so I got into environmental studies.
[53:11] When I graduated, I said, I want to go back to your photography.
[53:14] I said, no, you're going to fail.
[53:17] Because, you know, environmental studies in those days meant nothing, and now they matter a lot.
[53:23] But he said, why don't you go get an MBA?
[53:26] Why don't you go and see if they'll let you in and get a business degree?
[53:32] That way you have all the optionality in the world.
[53:34] And he was right.
[53:35] So he pushed me into post-graduate work.
[53:38] I came out of that MBA with perfect marks because I convinced the dean to let me make a film over the two years and I said, judge the film as a recruitment film.
[53:48] If it's a tool that works, mark me on my ability to capture this two year journey on film, I'll edit it, I'll cut it and let me off two courses.
[53:57] So give me enough time to do it.
[53:59] And he did, and I created the first recruitment film that really worked for them.
[54:06] Kerry, you know what I love about what you just said?
[54:08] It puts together everything about you, meaning you love business and you love business.
[54:15] filmmaking and movies and entertainment.
[54:17] Like that's Shark Tank, that's Dragon's Den, that's Marty Supreme, that's your life.
[54:22] And it goes back to that period when you would create a film about the business.
[54:27] Right, I mean, I still to this day, I think that's good for anybody to have a blend of yin and yang and the chaos of arts versus the discipline of business, which is binary.
[54:37] Either you make money, you lose money, versus arts, which is,
[54:39] You have an idea and you want to be creative about it and see where it goes.
[54:43] I still cut each week one social media post with Premiere Pro to keep my chops up.
[54:49] I sit down, I have a huge editing facility.
[54:52] The funny thing is I couldn't afford any cameras when I wanted to be a photographer.
[54:57] And just to spite my dad, I bought every camera when I got out and it started making money.
[55:01] I have a massive camera collection of Hasselblads and Leicas and vintage stuff.
[55:06] And I do all the digital stuff and I shoot everything.
[55:09] And I, you know, it's just, it's, it's, to me, it's very relaxing.
[55:13] Last night when we finished Shark Tank, I was so fried.
[55:16] You know, you know how it drains you, right?
[55:19] Like that's tough to sit there and do all those deals.
[55:21] Keep yourself sharp.
[55:22] I went into the bar downstairs in this hotel.
[55:25] I ordered a bottle of Montrachet, a very good one, and some great fish.
[55:30] And I pulled up my laptop and I edited all of the photos I'd been taking for the last few days.
[55:36] Very relaxing to do that.
[55:38] And I sent them out.
[55:39] Artemis got one and Mindy got some.
[55:42] And they're very appreciative.
[55:43] Your stepdad, when he told you, you're not going to make it as a photographer, that was an important moment for you, both because it then pivoted you, but was it also that he was speaking truth to you and that's who you became to be comfortable with just saying what needs to be said?
[56:01] Do you think that that was an essential moment or am I reading too much into it?
[56:05] No, you may be right.
[56:07] Maybe what he was trying to do is to challenge me to go get motivated to prove him wrong, which is what's happened in data centers, for example.
[56:15] Anytime anybody says you can't do it, I go do it.
[56:17] And I do it over and over again.
[56:18] I don't always... You were born with that?
[56:21] Well, it might have been, but he was trying to say, look, there's risk.
[56:26] You may not make it.
[56:27] You may burn all that time and not make it.
[56:30] Why don't you diversify risk through option?
[56:34] And I tell my own kids that.
[56:35] Option value is a big thing in my family.
[56:37] I say, Trevor, what's the option?
[56:39] Like why, what's, get some option value in this strategy just in case it doesn't work.
[56:45] What's the option?
[56:45] What's the B plan?
[56:46] What are you gonna do?
[56:47] And you know, some guys say, well, they're, burn the boats, there's no B plan.
[56:50] Bullshit, you have to have a strategy in case it doesn't work on the first attempt, pivot.
[56:55] You got to pivot.
[56:56] I pivot all the time.
[56:57] You know, your strategy in life is very connected to creating that optionality.
[57:02] Like that he taught you that very valuable thing.
[57:05] By the way, the best business people are not like me where I risked everything, but the people I, when you create more upside and no downside, that works out better.
[57:16] So you can create optionality.
[57:18] Everybody likes, you know, you somehow built this huge business with a brand that stayed intact.
[57:26] with this message of kind, and it's also the name of the company, obviously, but that's very powerful in terms of incremental choice in the snacking category where you have so many choices.
[57:36] I always reach for the kind because I understand the brand versus all the other shit out there, and there's a lot of it, and that category remains brutally competitive.
[57:47] So I don't think you had a strategy.
[57:49] I think you figured out, I'm going to try this, and when you saw it working, you stuck with it.
[57:54] That's what I think.
[57:55] No, we kind of had it, but it evolved and changed.
[57:58] But I want to just end with where you were a minute ago about Shark Tank.
[58:03] Like, I am in marvel of you because I'll shoot two, three days in one season, and I am fried.
[58:12] And to your point, days go by and I'm like processing, because it's very intense.
[58:18] You do the entire season.
[58:21] I don't even understand.
[58:22] Do you have a tool for how to not get tired, demotivated, confused?
[58:28] For me, it's hard to keep up with all these companies.
[58:32] Do you have... Yeah, no, I learned years and years and years ago.
[58:37] I think what's important is when you finish the pitch, you need to do the morning pitches.
[58:44] Flush them out of your brain.
[58:46] Forget about them.
[58:46] Oh, you actually do the opposite of what I thought.
[58:48] I don't remember what we shot in the morning, and I've intentionally done that to myself so that I can absorb.
[58:52] So you can have a clean slate.
[58:53] I have a clean slate.
[58:54] I don't let the decision from the morning take.
[58:56] Why didn't you tell me these eight years ago?
[58:58] I would have been a better shot.
[58:59] Because the thing is, you learn it on your own.
[59:03] I don't remember.
[59:04] I have to go to Matt, my analyst, who comes here for all the pitches, say, okay, what did we do this season?
[59:08] And we nicknamed them all, whether it's this or that.
[59:12] And the thing I've learned, which I think is so great about Shark Tank, and obviously you've been around long enough to know this, you go through a season, you do, I don't know, 10, 12 deals, whatever it is, and you think you're so sure about the three winners.
[59:27] You think you know.
[59:28] And then you get surprised.
[59:29] You get completely surprised.
[59:31] eBay Windows 10.
[59:32] 36 months later, four months later, four or five years later,
[59:38] You have no idea what's going to happen because it could be the market, it could be the individual, it could be just sheer luck.
[59:45] I've been amazed at the journey.
[59:46] I've been amazed at the outcomes.
[59:48] I can't believe, you know, Bass Paws and Felicious and all this stuff.
[59:53] They were not my winners.
[59:55] Okay, we're going to pivot to something called the Mexican Inquisition.
[1:00:04] So I'm going to ask you questions you need to try to think about hard and fast.
[1:00:08] Okay.
[1:00:09] Ready?
[1:00:10] Name an unsung hero who helped you get here.
[1:00:14] My stepfather, for sure.
[1:00:16] I mean, he's unsung, but without him, I wouldn't be here.
[1:00:20] Yeah.
[1:00:21] What is a question I should have asked you or that you've never been asked or that I should have asked you today and I missed out on?
[1:00:26] How good a guitarist are you?
[1:00:29] I've seen you perform in the tank.
[1:00:31] You're doing the real.
[1:00:32] Well, I'm learning that, remember John Mayer came, maybe you don't remember this, he came to the set.
[1:00:37] Who did?
[1:00:38] John Mayer came to Shark Tank.
[1:00:40] He said, you're a Shark Tank fan.
[1:00:41] You want to take a picture in the chairs?
[1:00:43] And he said, look, I'm recording.
[1:00:44] Why don't you come down to my studio tonight?
[1:00:46] I'm going to record at 2 in the morning.
[1:00:48] And I went down there at 2 in the morning in L.A. to Capitol Records with Linda, my wife, and watched him record his new album.
[1:00:56] And he said, why don't you play for me?
[1:00:58] And I played Jimi Hendrix's original guitar that he had there.
[1:01:03] And he said to me, you know, Kevin...
[1:01:07] you're trying to be too fast.
[1:01:09] Everything you're doing is too fast.
[1:01:11] Why don't you slow it down by 70%?
[1:01:15] Like, hold the note longer.
[1:01:17] Do it slower.
[1:01:18] Have more feeling.
[1:01:20] And that's much harder to do.
[1:01:23] And that's why I realized, wow, he's...
[1:01:27] there's something to look up for.
[1:01:28] But isn't that advice about life?
[1:01:30] Yeah, maybe.
[1:01:30] We move so fast and everything that I find that if you slow it down, you're actually better.
[1:01:34] Yeah, I think that's great.
[1:01:36] It's a great lesson is arts towards life.
[1:01:38] That's a good question.
[1:01:39] Who's a historical figure that you wish you could have lunch with?
[1:01:43] Bismarck, best negotiator in history.
[1:01:46] He had the innate ability to read a person within moments and knew right away their strengths and their weaknesses.
[1:01:53] That is a great asset to be able to do that.
[1:01:56] It doesn't matter what generation, what era you're in.
[1:01:58] Even 200 years ago, it doesn't matter.
[1:02:00] What's something you've changed your mind on over the last year?
[1:02:04] I don't micromanage anymore at all.
[1:02:08] I just, I find a leader, put them in place, tell them let's agree on a goal over the next 12 months.
[1:02:15] If you don't make it, I whack you.
[1:02:18] But I'm not gonna tell you what to do because I'm funding you.
[1:02:22] When did you figure that out?
[1:02:23] Because I used to be a micromanager, but I figured it out.
[1:02:26] Early on, you cannot micromanage.
[1:02:29] You either empower people to get it done, if it's not working out, you let them go.
[1:02:32] But I'm talking complete laissez-faire.
[1:02:34] You know, I don't mind giving advice if I've asked for it, but I don't tell them what to do.
[1:02:38] It's working.
[1:02:39] You know, there comes a point where you've got to let go.
[1:02:42] And it's just happening for me now.
[1:02:44] What drives you?
[1:02:45] I just like to be in the game like you do.
[1:02:47] I mean, I'm very interested in just being in the game.
[1:02:50] I mean, I don't know what else I would do.
[1:02:52] I tried retirement, it was very boring.
[1:02:54] This is, I'm having more fun than I've ever had in my life.
[1:02:57] I'm working harder than I ever have.
[1:02:59] You know, I do four, sometimes five cities in one day.
[1:03:03] I'm involved in crazy stuff.
[1:03:05] I mean, just crazy stuff.
[1:03:07] And something you've obviously figured out is Shark Tank has opened doors for me around the world.
[1:03:13] All right, now we're going to do one last section.
[1:03:15] This one really is rapid fire.
[1:03:17] Ready?
[1:03:18] Build or break.
[1:03:18] If you like it, you go like this.
[1:03:20] If it's break, you say build or break.
[1:03:22] Okay.
[1:03:23] Build or break the butt of a young celebrity.
[1:03:28] Build.
[1:03:29] We're talking about...
[1:03:30] Marty Supreme.
[1:03:32] Do you know the story there?
[1:03:33] There was a stunt double at 3 in the morning, and they said, bring in the stunt because we're not going to whack Chalamet's ass.
[1:03:40] Too risky.
[1:03:41] And then Timothy came out and said, I don't want another ass.
[1:03:45] I want my ass because it's going to be immortalized.
[1:03:47] I said, you don't want me to hit you like this.
[1:03:49] He said, go ahead.
[1:03:50] And...
[1:03:52] And I tried to slow down the paddle.
[1:03:54] And the director said, you're holding back.
[1:03:57] And it's showing up.
[1:03:57] And it's not good.
[1:03:59] It's not good.
[1:03:59] I love that story.
[1:04:00] I love that story.
[1:04:02] Build or break seven guest sharks on last season.
[1:04:05] Break.
[1:04:05] Yeah, it was too many.
[1:04:06] Too many.
[1:04:07] Too many.
[1:04:08] I think guest sharks are really, really valuable.
[1:04:10] No, they are.
[1:04:10] But you can't do that many.
[1:04:11] Build or break filming a whole season in one period.
[1:04:17] I'm for that.
[1:04:17] Build.
[1:04:18] I like to get it over with.
[1:04:20] Get it done.
[1:04:20] But it's not overwhelming to you because you have the problem.
[1:04:23] No, no.
[1:04:23] In the old days, I used to do 22 episodes all in a row.
[1:04:26] No breaks.
[1:04:28] No breaks.
[1:04:29] No breaks.
[1:04:29] I don't understand it.
[1:04:30] You're a real man.
[1:04:31] And you shave twice in a day.
[1:04:35] Build or break poutine?
[1:04:37] Break because I don't eat carbs like that anymore.
[1:04:39] Poutine is a Canadian...
[1:04:42] It's a potato dish.
[1:04:44] It's French fries with sauce on it.
[1:04:47] I tried it.
[1:04:48] Very rich.
[1:04:48] I couldn't get into it.
[1:04:49] It's 1,000 calories.
[1:04:50] Build or break AI regulation.
[1:04:54] Break.
[1:04:54] I don't want any regulation on AI.
[1:04:57] None whatsoever.
[1:04:57] No.
[1:04:58] I want innovation.
[1:05:00] No regulation, but that's not what's going to happen.
[1:05:02] The Chinese don't regulate AI.
[1:05:04] We're competing with them.
[1:05:05] That's what's going on.
[1:05:07] Build or break craft services for scripted movies.
[1:05:13] Build.
[1:05:13] You were saying, I just found it funny in one of your interviews.
[1:05:17] You're like, you know, there's different types and hierarchies.
[1:05:19] You know, the unscripted, we get treated like the paupers compared to like.
[1:05:26] Yeah.
[1:05:27] When I was shooting Marty Supreme, it's a different level of support because you're working 18 to 20 hours all night.
[1:05:32] You need nourishment.
[1:05:33] You need, you know, it's different.
[1:05:35] Shooting a film is just different.
[1:05:38] And it's interesting and different.
[1:05:40] And I'm going to do it again.
[1:05:41] I'm going to do one project a year.
[1:05:42] I've looked at three scripts.
[1:05:43] They're all shit so far.
[1:05:45] But honestly, Marty Supreme, what a movie.
[1:05:48] You invited us to the premiere.
[1:05:49] We enjoyed it.
[1:05:50] We were all stunned at how great a job you did.
[1:05:53] But on the other side, it was you.
[1:05:55] And the director... Josh Safdie.
[1:05:58] Josh Safdie talked about how he was looking for the essence of the character.
[1:06:02] And I talked to him afterwards, and he looks for people that inhabit that character.
[1:06:06] Do you plan to do stuff that's not... No, I want to stay the antagonist.
[1:06:10] It's a richer role.
[1:06:11] I'm looking for bad guy roles.
[1:06:13] I think there's much more interesting...
[1:06:16] you know, elements to explore when you're the bad guy.
[1:06:19] I mean, it's better for me, for what I do.
[1:06:23] And, you know, everybody thinks I'm the bad guy anyway, so it's an easy role to get into.
[1:06:27] But I think if you read scripts and you have an antagonist, it's always a richer role.
[1:06:33] And that's what I want to do.
[1:06:34] But you don't see any tension between you continuing to build a multi-billion dollar business empire, you being in the news as a commentator and you being
[1:06:44] movie actor?
[1:06:45] Like, for you, they all can...
[1:06:47] I don't spend any time worrying about it.
[1:06:49] I mean, it's sort of... You know, I think everybody should have...
[1:06:53] Entrepreneurship is about buying freedom.
[1:06:55] It's not about the pursuit of greed.
[1:06:58] I can do anything I want, and why don't I?
[1:07:01] Like, I don't... You know, people say, well, aren't you worried about...
[1:07:05] but people think about that, I don't even spend a second worrying about that.
[1:07:09] I don't care.
[1:07:10] Like, how can you possibly spend any of your energy worrying about what someone else thinks?
[1:07:17] You answer to yourself.
[1:07:19] It's what you think that matters.
[1:07:21] And I think that's something every young person should think a lot about.
[1:07:25] Don't try and please everybody because you can't.
[1:07:28] You should worry about your close friends, your family, your children, your wife, your parents.
[1:07:33] They matter.
[1:07:34] You should listen to them.
[1:07:35] But if you're going to be involved in the media, there's millions of people and you can't make them all happy.
[1:07:42] You just can't.
[1:07:43] And you shouldn't try.
[1:07:44] And on that note, we're in.
[1:07:47] Thank you.
[1:07:49] That was amazing.
[1:07:51] We want you to become a builder with us.
[1:07:53] So subscribe to Builder Break now and leave us a comment or a review.
[1:07:57] We're trying to build a movement and you can be part of it by hitting the notification bell and telling us what you think about this episode and by telling all your friends to watch too.
[1:08:08] Thank you.

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