Transcript

Why Most Deals Fail with Shark Tank's Kevin O'Leary

From Tommy Mello · Episode page · Watch on YouTube

· 33 min · 6,811 words · 74 timestamped sections

This is the full, timestamped transcript of "Why Most Deals Fail with Shark Tank's Kevin O'Leary", an episode of Tommy Mello published November 15, 2025 (33 min, about 6,811 words). It mentions 6 people, works and ideas, including Kevin Olirri, Shark Tank, Who Not How, Marty Supreme, How to Win Friends and Influence People.

What this episode is about

In a conversation with businessman Kevin O'Leary, known as Mr. Wonderful from Shark Tank, he shares insights on why most business deals fail, emphasizing the importance of listening, honesty, and execution in achieving success. O'Leary's perspective highlights the critical role of sharp business instincts and a relentless focus on profitability as key factors in overcoming challenges in entrepreneurship.

Key takeaways

  • Listening isn't just passive; it’s a superpower that transforms interactions into insights.
  • Truth-telling: the ultimate insurance policy against cognitive overload. Forgetting has never been so efficient!
  • Entrepreneurship is less of a race and more of a marathon—complete with pit stops and survival tips.
  • In an age of automation, traditional home services thrive—real estate remains the heartbeat of wealth.
  • Multiples are climbing faster than a tech startup's valuation—recurring revenue is the golden goose investors crave!

Who speaks in this episode?

What is discussed, and when

  1. – 5:00: Kevin Olirri, Shark Tank
  2. – 20:00: Shark Tank, Who Not How
  3. – 30:00: Marty Supreme
  4. – 33:22: How to Win Friends and Influence People

Notable quotes from "Why Most Deals Fail with Shark Tank's Kevin O'Leary"

  • Sharp, legendary, wonderful. Our guest today is Kevin Olirri, one of the most recognizable investors and entrepreneurs in the world.
    about Kevin Olirri · at
  • Ben Hardy, Dr. Benjamin Hardy and Dan Sullivan. I don't know if you know them, but they wrote several books. Who Not, how was one of my favorite and just the cliche or the…
    about Who Not How · at
  • An opportunity and I did it and you can judge for yourself. It's a movie called Marty Supreme coming out Christmas Day.
    about Marty Supreme · at
  • Depending on the sector, but if you had to pick a book that was just like change the way you do things, how to win friends and influence people is probably one of my favorite, but what would you say is a book that is the game changer?
    about How to Win Friends and Influence People · at

Who and what is mentioned in this episode?

People

Books & papers

Companies & orgs

Concepts & topics

  • Shark Tank — Concept · 3 mentions · first at
    Known to millions as Mr. wonderful on Shark Tank. Kevin built his reputation by pairing sharp business instincts with direct, nononsense advice that cuts straight to the truth.

Full transcript with timestamps

When you listen, you get more power. I'm happy to just listen. And it's very powerful. It works immensely. That's one thing I wish I'd learned in my 20s because I talked too much back then, but now I don't. I'm very careful. I just listen.

Sharp, legendary, wonderful. Our guest today is Kevin Olirri, one of the most recognizable investors and entrepreneurs in the world.

The great thing about telling the truth is you never have to remember what you said.

Known to millions as Mr. wonderful on Shark Tank. Kevin built his reputation by pairing sharp business instincts with direct, nononsense advice that cuts straight to the truth.

You come into my kitchen, buddy, you got to take the heat. He's the chairman of OShar's Investments, a best-selling author, and a champion of entrepreneurship. He's helped countless founders sharpen their pitches and scale their businesses.

Every entrepreneur I've ever talked to has a defining moment where they are pushed into this path. Beyond television, Kevin has built and advised companies across industries. From software to consumer goods, one thing has never changed. His relentless focus on execution and profitability. There's the people that own the store, and there's the people that scrape the off the floor.

Whether you agree with him or not, Kevin Olirri forces you to think differently about money, success, and business.

Watches and wine go so well together. Get ready. It's time to hear some of the top tier business advice directly from the shark's mouth. All right, guys. Welcome back to the Mellow Millionaire. Today's a very special day. We got the freedom event out there. Kevin Olirri sitting next to me. Today's guest Harley needs an introduction known as millions as Mr. Wonderful from Shark Tank. Worldclass investor, entrepreneur, business leader who built and sold the learning company in one of the largest tech deals of all time. He went on to launch Olri Funds and Olyri Ventures and today manages a diverse portfolio that spans everything from fintech crypto to consumer brands.

Best-selling author, global speaker, and a straight shooter on personal finance. Kevin, I'm really excited that you're here brother.

Appreciate it. Why did you decide to do this is my first question. I love working with entrepreneurs. And you know what that room was full of was entrepreneurs. people that really understand that entrepreneurship is not a destination. It's a journey and we're all in it together and we were sharing our thoughts together. I really enjoyed that session because there's a lot of energy in that room. But that's what it's about. When you start a business in America, it's it's a only a third of the population can pull it off. I mean, it's it's not for everybody, and I'm not telling people to do it, but if you are going to do it, you want to talk to other entrepreneurs. You want to share ideas. you you want to help entrepreneurs not make the same mistakes that I made. So I kind of go through that journey saying here's what worked, here's what didn't. Here's what I've learned recently. Here's what I've

applied. Here's how it's worked. I want to share. You want to give back. That's the way I look at it.

What do you think about the home service industry? It's probably the one of the best times ever to be in it. Um, not only technology advancing it, it's never going away. It's never going to be replaced by AI or any of this disruption stuff. It's the core of most people's net worth is where they live and they care about it. It's a it's a spectacular industry. you know, there uh we run at my company 25,000 jobs a month and uh you know what's crazy what happened through co is we were deemed essential and uh I've been through 2008 as you know the multiples went from 10 to 12 to 14 to 18 to 20x yeah

isn't that crazy 20x and it's hard to do the math really of 20x multiples on eBay and then I learned about annual reoccurring revenue You get a multiple of that.

Yeah. And it's it's fun stuff. What do you look for when you make an investment?

I look exactly for that. How do I get my money back? First of all, secondly, how re howa stable is the reoccurring revenue? How risky is that recurring revenue? Like what would make it stop? I mean, I'll pay way more for a safe investment that has recurring subscription or whatever it is to keep continuing every month. That's what you're describing and that's why it's valuable and it turns out the whole market feels that way. And so these multiples have increased for a reason. It's the safety of the investment. First to return the capital invested and then to acrew the benefits of a renewed pace of free cash flow. That's very very valuable. People covet those kind of investments. And so it takes executional skills too. You have to have someone that can execute that can do it. But if you understand the model and how to acquire a customer and how to maintain it and it generates cash, that's pure

gold. And that's what this business is. That's why it went from a seven to a 20. That's not you or I deciding the market decided that because that's what the market wants. And so you're very lucky to be in that space right now. Very fortunate. And I think it's going to 6x in the next seven years. And uh I watch a lot of people there's a lot of jobs going away and it's scary. It's kind of scary in a one way. I mean, I just heard Bill Gates come out and say in 10 years there's going to be a government subsidize. You're going to have to pay people to live because robots next year, Elon Musk, it could cook for you. It could walk the dogs. I mean, where are we going? What do you think about when the future? You know, I I' I've listened to that narrative for for multiple generations now. And I I bet you if you were um you had a family business back 150 years ago making horsedrawn buggies and you went and saw

the first car roll off the Ford production line with four tires on it and an engine in it, you say, "Oh, we're we're we're dead. I mean, we're all going to lose our jobs." That's not what happened to the economy. New technologies, advanced productivity. There's a shift in who works on what and where. That happens. because there's dislocation, but because it's productivity enhancing, the economy actually expands. It's the same argument as saying, "Oh, well, television is going to destroy radio." That's complete BS. Radio still exists. Comes from satellites now. I don't worry about that kind of stuff. I don't believe in predicting doom in the American economy.

That's never worked. It never has happened. I've never bet against the American economy. It's it's provided an 8 to 10% return on average for almost 200 years. I mean, we're good at doing stuff that makes it easier to live and more productive. If if I need a robot or a a car that's going to drive me, great. And whoever was going to drive that car is going to do something else, probably a business that's more valuable and make even more money. It's going to free human beings from tedious tasks like flipping burgers. I saw a robot flipping burgers the other day. I don't care.

I'll eat the burger as long as it tastes good. Yeah. I uh I I think a lot about where business is going and um just like you just showed the video of you. I can speak in Russian, Japanese, my AI, hey genen, some of the other tools we're using. I just watched I think have you ever heard of N8N? It's like Zapier but for AI. I could literally have it research the number one post for home service and build a whole integration that actually goes out, does the research, writes it, I'm talking, builds a thumbnail, which Mr. B spends $40,000 on a thumbnail and it posts and build it perfect for X, Tik Tok, Instagram. I know every major PE company in the space, all of them.

Blackstone, KKR, Apollo, all of them. and they walk in, they treat them like a a cog, a wheel, and they watch it fall apart because they say, number one, you can't cut your way to success. And uh I've seen very few people pull it off. That's why PE just learned never get rid of the founder. Never get rid of the founder. What is that? I I don't know if you've ever seen that when they go in and they start looking at balance sheets and income statements and cash flow and they try to figure out a way to absorb the like make it more profitable very quickly. Have you ever seen that in business?

Yeah. Yeah. I see that all the time. The challenge is the analysts that do that work. Have you never actually run a business? It's it's a problem with PE and venture capital. Until you've actually made payroll on a Wednesday night, you don't know what it's like and how hard it is to run a business. And to just use the metrics of, okay, I'll I'll put debt on it or I'll change this, I'll change that, and it's going to be more profitable. Rarely works out. And and the PE guys aren't that stupid anymore. they're starting to realize they got to partner with the founder, figure out a way to keep them motivated, but so a founder in their 60s or 70s is looking for some liquidity for generational reasons, but they don't necessarily want to stop working. And so the the better strategy is to partner with them. Maybe you buy, you know, a 80% control position and you cash out the family, but maybe some members want to stay

working and they know all the customers. That's a much better model. and you give them incentives to to actually work as hard as they did when they controlled it. It doesn't always work, but it works a lot better than just buying it out and thinking you can just parachute in some random CEO that doesn't know anything about the history and the culture. And I would also say something that, you know, you touched on at the beginning of this question about technology. You know, you should use every tool that you can afford to advance productivity both personally and in your business because your competitor definitely is. And I'll give you an example. Damon got me into this. I'm going to pull it out of my ear. This is an IFB, a Bluetooth IFB from a company called Starky. I don't own any of Starky. Why am I wearing this thing?

This thing is connected to my phone. It reads to me every communication I'm getting. Even if it comes in a foreign language, it translates it into English for me. I've chosen five different languages because I'm doing business in the Middle East. You can use it for all kinds of purposes. You know, if you've got a bomb ear, you can use it a hearing aid, but if I want to listen to the conversation over there, I can tune it to listen in over there. Now, these are not cheap. $6,000, but this thing has saved my Heine so many times when I travel and, you know, or or I'm doing something like on television. I've got the the director in my ear. I'm on live TV and I'm getting my messages on all of my deals and this ear is reading it to me and I'm able to absorb that and be more productive. So the minute I get off air, I can call. I'm not the only guy. I mean, a lot of the sharks are using these things now and Damon brought them

to us. That's great. It's very cool. Very cool. You know, I'm going to get one of those clips that that actually monitor everything I do in the day and they listen to everything and I just know uh my assistant, my executive, she's right over there. She's the best. Ashley, she's hiring another assistant for her and I said, "They got to be using Chad GBT5. They've got to be tech enabled."

I use that every day myself. Our entire companies use it. We all have subscription services. We look at our our social media, put it through all of the models to see if we can change one or two words. You know, a 15-second commercial has 75 words in it. Which 75? Because we spend a lot of money on digital advertising. So, we're testing. We'll do three versions. We'll put it through Chat GBT and other models and say it'll change two words. Then we test it in the Florida market. Boom. It worked better. Yeah. But testing works.

I mean, you can do it by by geolocking your Facebook buy or whatever you're using. And it's so easy to do it now. Like it's not that complicated.

You know what's interesting? I just thought of this is uh I'm a big fan of attribution. I have 7,000 call tracking numbers. Every single landing page has a separate UTM parameters. Like I know exactly. We spend right now on average 3.75 million a month in marketing and um

what do you think what do you think you make back on that? Think you make 9 million bucks? What do you think?

No, I get a my advertising budget is 12%. So I almost get a 9.4%. My rorowaz I'm getting almost a 10 times return. And if you're getting 10, you you fine-tuned it. That's what that's amazing.

I spent a lot of money on branding. Even our trucks is a logo. It's a driving billboard. Uh but one of the thing that was really interesting is it's been very very hard for TV, radio, billboards to get attribution. What I'm going to talk about here a little bit is four KPIs. I track that I can build the budget. I could go into any business. I don't care if it's dental. I don't care if what country I'm in. Their booking rate, which is your contact center, is when the phone call comes in or the ad or the lead comes in. Conversion rate when you're doortodoor knocking and you meet the client. Uh the average ticket and the cost per lead. I don't like cost per acquisition because this funnel already builds that into it. And with those numbers, I could actually build the future of any company. And I'm like, how do you do more with what you got?

Everybody's saying I need leads. Well, in co everybody said, I need people. So, I look at marketing is how do I attract good talent? And uh one of the things if you're going to build businesses, how do you acquire great talent? Like what do you look for? How do you find great talent? Why have 54 companies too is is why not put it all into one? Well, it is in a holding company. They're all owned either through debt or equity. Not all in a control position, but many of them. Um, it's a portfolio strategy and at any one time, you know, within that portfolio, there's a catastrophe happening or a euphoric outcome. I have one that just uh yesterday told me uh they're getting sued and then an hour later I get a phone call from another saying they're they're going public and they're going to be listed in 3 weeks. I own a huge piece of that. So, I mean, I get I get the portfolio strategy is is heartbreak one hour and euphoria the

next. And I've kind of learned that that's just the way it is in life. You're going to have good, bad, and ugly. But having many companies means the outcomes generally I look at on an annual basis.

17%. Well, it that's we've had better years. That's not the greatest. Private equity gets 22.

So, we have some work to do, but 17's pretty damn good. It doubles in four years. I just

Yeah. No, I'm very proud of what we've achieved. And that means we're doing a good job managing them. Uh they're profitable. And then, of course, on top of that, we get the distributions every month. I'm getting checks from pretty well everything. And that's that maintains and supports the community, you know, the families that work. Um, our our biggest cost increase, social media. Boy, it's expensive. I mean, that we're just spending a fortune generating content. And as long as our rorowaz is four or better, as you know, we're happy with that spend. Have you ever heard of a guy named Roy Williams in Austin, Texas?

Uh, I've worked with him and uh he said, "Quit making ads transactional. Tell stories. Let people get to know you." you talked about that on stage is uh let people see who you are. So I started writing ads about uh me and my dad working in the garage working on a car and people just relate to it and if you can tell stories on ads and not say we're cutting prices 15% off and that works but it's kind of a race to the bottom. Walmart figured it out but every nobody could ever beat Walmart again I don't think. Well, their scale of purchase, you can't beat them. But your point is, it's being transparent about who you are. And if people want to be part of that community and that culture and that vision, they're going to become your customer. And those are very valuable. And I agree with that. That is the Wicked Cupcake story. What we learned from Wicked Good Cupcakes. That whole thing was unbelievable what

happened there. I mean, cupcakes are total commodity. Anybody can make a cupcake, but they turned it into a massive business and no one saw it coming. I uh I tell customers I was in the garage for nine years. I'm an overnight success of two decades. So I was running jobs. I was running six a day, six days a week. Failed relationships. Never been married, no kids. But uh I got a fiance now. And

congratulations. I'm very excited about it. Uh but I say, you know, Mr. Olirri, here's what you need to do. Here's what you should do. And this is the third one that works every time. My mom worked three jobs when I was a kid. She worked her ass off. I love my mom more than anything in this world. Here's what I'd be telling my mom to do. This this is what I tell people. This is what I'd be telling mom to do.

Yeah. And I always give them what I would do for mom. And if I could treat people like mom, they keep coming back. Well, I have a similar story. I I learned so much from my mother about how I conduct myself today. She told me something once that I've never forgotten. And it's actually, you know, changed who I am, I think, over time. Um, always tell the truth. She said this to me, "Always tell the truth and you'll never have to remember what you said, which is very hard to do in the moment because when you tell people the truth, sometimes they don't like it, but still the truth." And that in the context of Shark Tank made me the bad guy, but I'm actually the friendliest guy because I'm telling you, you have a bad idea and you're going to go bankrupt with it. And it's, you know, you should try something else. But the point is, you get great lessons from mothers because they care a lot about you. But that one for me was

great. and she taught me how to invest even though she wasn't an analyst or anything. Diversification's everything and always get a check either buy a bond with interest or a stock with, you know, a dividend. And that that's kind of what I did and and she was right about that. But, you know, it's it's really become an interesting journey for me. You always have mentors in your life. And there was another guy named Jerry Patterson um who uh said, you know, you really should focus on things you got to get done during the day and not listen to all the noise around you. He was actually a hockey agent, the first guy to bring in a Russian hockey player into the NHL, which was really controversial, but he did it. And he was my partner in a company called Special Event Television. We used to shoot the intermissions in Boston and Detroit and New York, you know, for the for the league. Yeah. Yeah, I mean it was so I I

really got involved in hockey in so 1988 to85 when Gretzky was in the league and I learned so much from Jerry uh just about how to conduct business and I learned a lot about hockey um and the game it's become and about professional sports. There's so many different lessons you're going to learn in your life through your your journey and you should always pull knowledge out of everything you're doing and it just makes you a better and more productive entrepreneur. I think

Ben Hardy, Dr. Benjamin Hardy and Dan Sullivan. I don't know if you know them, but they wrote several books. Who Not, how was one of my favorite and just the cliche or the the message of who? How do I get the right who's I love when I walk in a board meeting, everyone says no to me? How do you get the right people on your team? What do you look for? What I do, and I've changed this u recently, maybe the last three years, the right people are ones that can work within the team on a mandate that everybody agrees on. So, they're all going in the same direction. But you don't know that when you hire somebody.

You're not sure. So, don't hire them. Hire them as contractors first. My standard deal is, look, let's work out your contracts as if you were already successful. Let's get that and put it here on the shelf. But, I'm going to pay you 30% more to be a contractor for the next 6 months. And at any time during that six-month period, we can change our mind. say you fit into the team. It's all working. Or you can walk away saying, "I don't think it's going to work here." And it won't be a blight on your resume. You just acted as a contractor, so you don't have to say you were hired and fired, and I don't have to do the same to you.

So, you're paying 30% more. Who gives a damn? It cost you a lot more than that to hire somebody and two weeks later fire them. Yeah. That's crazy. And so, this is my new strategy and and that's how I find great people and they appreciate it. And it just plain works

when you share everything like you do. And people always ask me, "Why do you give me your playbook when people come into my shop, my competitors, and I say,"Well, you know, you're more likely to be a millionaire than have a six-pack, and I can tell you exactly how to get a six-pack." You still got to do the work. Less than 1% of the people will do the work, but you share everything.

Yeah. I mean, look, you know, I'm happy to share it because I know that the magic sauce is ex executional skills. You can understand how a business is successful. You can't necessarily execute the same way. Great ideas are diamond and dust and executional skills are impossible to find. Great people have them their ability to set a goal and achieve them consistently over and over again. And that comes from being a great salesperson learning that way. I like to see people come up through sales because they understand how hard it is at the beginning of the month to be zero and then have to hit the goal every month. I did that for my whole life.

Still do. But just cuz you know how a business is operated and it's transparent about about it. I bet you less than one out of 10 people can do the same thing.

It's very rare. I mean less than that. You mentioned you work for uh Steve Jobs and he was an

100%. I love the fact that he was just a creator, but I always I watch all of his videos and he goes, "The worst I love the fact that he goes, if you hire great people, they'll tell you where to go." And that's what he figured out. I mean, but I I could see the in him 100%. He just was really difficult to work with. It doesn't mean he wasn't a genius. He was. He also taught me about the concept of signal to noise ratio, which I've really adopted. um he uh would argue that you need to get three things done every day, whatever they are, three to five, three to five things you have to get done every day and that's the signal. Um the noise is all the stuff that comes at you that stops you from getting the three to five things done. And so you have to identify the three things and then you have to fight off all of the noise coming at you to stay within 7030 ratio. You got to block out 70% of the noise so that 30%

is getting the three things done. Now, because you're blocking out noise, you're perceived as an You're just you're stopping people in midset and saying, "I'm not interested. Not interested." Just not wasting time is what he was about. He was blunt. He was difficult. He was ordinary. He had a woman working beside him back then named Heidi Rosen who would smooth things out afterwards, you know, and we would have contentious meetings in the old headquarters. Brutal. And he would just, you know, be brutal. And he some of my staff would be crying when it was over.

And then Heidi would call me on the way back to SFO and say, "Look, uh, we're going to pay you the 12 million for the update or whatever it is, you know." But she wouldn't even apologize for Steve. We were past that. I didn't need to. And he would. There was no text back then. He would email me at 3:00 in the morning, Boston time, and expect an answer within 5 minutes. And I would give it to him because he was such a huge client. I'd wake up for that. That was him being on signal. And so I've I've kind of adopted that, too. You got to understand you you will get stuff coming at you all day.

You know, you mentioned you're you hire the CEO. When I learned about equity incentive programs, it's a equity incentive programs gives people a stake in the outcome. And if you do them right, you make a lot of millionaires and you make a lot of owners. You know, how do you feel about equity? I I I 100% believe in it. Um, you know, of my model often if there's an operating business, someone comes to me and says, "Let's start this operating business. It's my idea, but I want you as an investor." I'll say, "Look, I'll do a 7030 deal with you. I'll do 70, you do 30." But the minute you hire somebody that needs equity, we get equally diluted. So, we start at 7030 and then as new people come in, we equally get diluted. That makes the person who's running the deal, the guy with the 30% sweat every hire because he or she is also taking the hit,

the dilution. And so, but I want they know they have to give away some and as the business grows, they keep giving away and they have to cuz they're because I believe everybody that's important to the business should have some sweat equity in it. How do you build a brand of somebody in there that's a million dollars a million dollars revenue and plumbing? What would you say the core essentials are to build a brand like like Mike Row? Everybody loves the guy like he nobody talks bad about him. He's done a great job of that. Uh brand building is now storytelling. That's what it is. And I I think um telling a transparent honest story about who you are, what you do, how you provide services, what what matters to you and your community of customers, that stuff is the only way you can build a brand. And then what happens is if you are a great provider, uh the customers start talking about your brand, your company, your service,

and they're the best ambassadors, they're the best advocates, they're the best advertisers for you. And that's why you have to spend most of your energy taking care of them. And the ones that are the noisiest ones are the squeaky wheels that are the most valuable. You know, it's it's such an amazing thing. And I talked about this in the presentation. Um unhappy customers are very valuable because they give you an opportunity to make them happy again

and then they become the biggest biggest advocates. And so you spend you should spend a lot of time taking care of unhappy customers and they become a huge asset to you. No matter what it takes, you got to solve that problem. You know, I used to uh I used to take all the uh one-star Yelp or Google calls myself and I'd call them up and I'd say, "Listen, I'm so embarrassed that this happened and your time is important. Can you tell me exactly what went wrong?" And I just all you have to do is let them talk and I just listen. And I would listen for 10 minutes and I go, "That is so embarrassing. I'm sorry." And I'd make it right. And uh you know, with 25,000 clients a month, we make mistakes,

of course. And we learn from those mistakes. Yeah. But you're guaranteed to make mistakes and you have to learn from them. But that's brand building. I mean, it's customer service in every business. I don't care what it is, financial services or, you know, HVAC or plumbing, it doesn't matter. It's customer, customer, customer, then employees and then shareholders in that order.

I ask three questions and I'm I love these questions for you in particular. Um, what's one piece of gamechanging advice that you wish you knew in your early 20s?

To reverse the ratio of talking and listening. Most people talk 70% of the day, listen 30. You should actually listen 70% of the day, talk 30. Because when you listen, you get more power. You understand where you're at. I was taught this by one of my women CEOs a few years ago. She said, "Kevin, you know, you talk too much and uh you're not listening and you should try reversing it and see how powerful you're going to become." And she was right. It helps you a lot to just listen. Listen. Go into a meeting and just listen. And sometimes there's an uncomfortable moment. You don't say anything and they start giving you information they didn't want to cuz they're they feel socially uncomfortable. I don't feel uncomfortable. I'm happy to just listen.

And it's very powerful. It works immensely. That's one thing I wish I'd learned in my 20s because I talked too much back then, but now I don't. I'm very careful. I just listen.

What's a millionaire habit that sets you apart from the rest? What I've learned, and I've started to do it recently, is I try and spend about 30% of my day doing something that's outside of my comfort zone. Something I'm completely uncomfortable about that I don't know how to do. I'm going to learn it. And that's exercising the brain. The brain wants to do that. You you don't ne you never give it that chance. You're always staying in your comfort zone and that's very bad. And so I'm I'm trying all kinds of things that that I thought I could never do and it's helping me immensely. And you know recently I I took on acting. I've never been an actor. I'm dyslexic. I can't memorize lines. Well, I found out a way to do it and I just that's helped me on other things and you know it was an amazing journey for me. I don't know what it'll lead to, but it was a hell of an opportunity and I did it and you can

judge for yourself. It's a movie called Marty Supreme coming out Christmas Day. It's it's a big movie with Timothy Shalomé and um Gwennne Pelro and I'm in this movie as an actor and check it out.

We will. If you had to start over tomorrow with 10 million, but you still got all your connections, $10 million, what are you doing with it?

I would do what I do now. I would diversify my holdings into, you know, I I have a very simple rule. No more than 20% in anyone's sector of the economy. There's 11 sectors. No more um than 5% in anyone's stock or bond or crypto. But there's one there's one thing I do uh break the rule for, and that's real estate. I have 31% of my, you know, net worth in real estate. And um I've [snorts] been a developer my whole life. And so doing, you know, real estate is what I do. um it's a core and you know I've done everything from climate control storage to luxury condos or whatever it just and right now the the hot sector in real estate is data centers so I'm doing that um but I like real estate you can touch it never goes to zero unless you put too much leverage on it and so you know I I very careful about how much debt I put into my equation I keep a very low debt ratio I want to be able to survive debt and uh

because I went through 2008 in real estate that was pretty tough So, it's kind of learning from the past experiences, but I take that 10 million and I I think I could probably, you know, do well with it by just being diversified.

Who do you look up to? Who's somebody that you just are like? Obviously, I know your mother at it.

Yeah, of course. Of course. But I think the guys that had most impact in terms of how I look at it was Steve Jobs and now Elon Musk, who's 100% signal. He has no noise. It's made him very awkward socially obviously, but um look at what that guy's produced and how successful he is in so many different sectors. Every mandate he takes on, he's wildly successful. You know, it just sort of um he really really understands that the metric of spending time on the things that matter. I've seen him walk away from a conversation mid-stream when he realizes there's no value here. I understand why he does it and I think he's achieved a lot. He's a good example for people to understand the whole noise to signal ratio and I think yeah that's I just look at executional skills. I look at what's the mandate when does it get done is it achieved yes or no the rest is all BS like you know and people that come to me and say look I want you

to invest in me I've had a couple of failures and I I've learned from my mistakes and I ask them you know why did that last business fail and they start blaming everybody else except themselves. blame these two fingers instead of these.

And I always say, you know, you own it. It failed because you screwed up. The only person responsible for failure is you and you spent the last half hour blaming everybody else, including the market. I'm not going to invest in you. You don't. If you don't understand why you failed, why would I want to invest in you? You should. Every time you fail, you should own it. If you're if you're an, you know, an entrepreneur, it's not anybody else. It's you. You're the reason and if people ask you, you should tell them the truth.

I love it. We're going to wrap up here in a minute. Um, you know, I'm a big reader and there's several, I guess, depending on the sector, but if you had to pick a book that was just like change the way you do things, how to win friends and influence people is probably one of my favorite, but what what would you say is a book that is the game changer?

I think Keith Richard's autobiography. Um, I've read many books, but that one really uh it's a huge book and it's it's all about his life. But there's so many lessons to be learned in terms of longevity and um focus in that book about sticking on mandate. And even through all of the problems he had, including drug addiction and getting arrested and all this stuff, the guy knew what he wanted to do and what he was good at and how to do it. and look at the success he's achieved. And I think everybody should read that book right from the early days when he was, you know, in in in junior school in in England and just just realize there's a lot of lessons.

He's very transparent in it. It's there's some tough parts in there. All right, close us out. Leave us with something for the listeners. And I, by the way, I really appreciate you being here brother.

You got it. Well, I really enjoyed it. This was a fantastic day. Um, if you ever get a chance to come to one of these sessions, you showed, it's it's just a it's a group of entrepreneurs just talking about u building businesses and I think there's nothing more noble than that and I've really enjoyed it. Thank you.

Thank you. Thanks so much for listening to this episode. Like always, we're going to close it out with the Tommy truth which is a little slice of wisdom from me to you that can help guide you in whatever you're striving towards right now.

The companies I've invested in, I'll give you a cool example. I put $4 million in a company for 35%. It will exit next summer and that $4 million will turn into 80. It's crazy because this is not uncommon. They're everywhere and there's a lot of those investments I've made, but it takes money to make money and I got to continue to be successful. And then all of a sudden, when you got 500 million in Goldman Sachs, they do a lot of special things for you. If you look it up, they treat clients completely different at 500 million. And then that's how the rich get richer. It's crazy. And that's it, guys. We'll talk to you next week.

Questions about this episode

Who speaks in "Why Most Deals Fail with Shark Tank's Kevin O'Leary"?

Tommy Mello (Host), Kevin O'Leary (Guest).

What is "Why Most Deals Fail with Shark Tank's Kevin O'Leary" about?

In a conversation with businessman Kevin O'Leary, known as Mr. Wonderful from Shark Tank, he shares insights on why most business deals fail, emphasizing the importance of listening, honesty, and execution in achieving success. O'Leary's perspective highlights the critical role of sharp business instincts and a relentless focus on profitability as key factors in overcoming challenges in…

What is mentioned in this Tommy Mello episode?

6 people, works and ideas are mentioned, including Kevin Olirri, Shark Tank, Who Not How, Marty Supreme, How to Win Friends and Influence People, O'Leary Funds. Each one on this page links to its own page with every episode that mentions it.

How long is "Why Most Deals Fail with Shark Tank's Kevin O'Leary"?

The episode runs 33 min; the transcript is about 6,811 words in 74 timestamped sections.

More from Tommy Mello

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 January 24, 2026.