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Jay Shetty PodcastJay Shetty Podcast

#1 Entrepreneur Reveals the Real Secret to Success (You’re Focusing on the Wrong Thing)

What if everything you’ve been told about success is missing one key ingredient, how deeply you care? Jay sits down with David Grutman, one of the most influential names in global hospitality, who built a world-renowned empire from the ground up. Together they unpack a powerful idea that challenges conventional wisdom: what if the real secret to success isn’t detachment, but deeply caring? From his early days as a bartender to creating iconic experiences that shape culture, David reveals how taking things personally, your work, your relationships, and every detail of what you put into the world, can become a driving force for growth. While most people are taught to brush things off, David chose the opposite, turning mistakes, rejection, and feedback into fuel to sharpen his craft and raise his standards. Jay highlights how David’s success wasn’t built on titles or transactions, but on genuine human connection. From remembering a guest’s drink to building long-term relationships with artists and entrepreneurs, David reveals that real influence comes from adding value without expectation. Jay reflects on how many people chase quick wins or surface-level networking, but true impact lies in playing the long game, showing up consistently, investing in others, and creating meaningful experiences that people never forget. In this episode you'll learn: How to Turn Mistakes Into Growth How to Build Relationships That Last How to Make People Feel Seen and Valued How to Build Confidence Without a Title How to Give Feedback That Actually Works How to Stay Grounded While Winning Every setback carries a lesson, and every interaction is an opportunity to build something meaningful. When you focus on adding value, staying curious, and giving your best, you begin to create momentum that others can feel. If you’re ready to level up how you show up in life and relationships, don’t miss David Grutman’s latest book, Take It Personal. Pre-order your copy today, visit: https://zandoprojects.com/books/take-it-personal-hardcover With Love and Gratitude, Jay Shetty JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast What We Discuss: 00:00 Intro 01:07 Why You Should Take It Personal 05:06 The Small Details That Make People Feel Seen 07:11 The Real Path to Self-Improvement 07:59 Turning Anger Into Growth 09:06 How to Give Feedback That Actually Works 11:20 Creating a 10/10 Customer Experience 12:52 Every Day Is a New Opportunity 14:33 Building Something From Nothing 16:27 The Power of Genuine Relationships 19:51 Does Networking Actually Work? 22:28 How to Play the Long Game 26:50 The Truth About Real Success 29:30 Lessons From a Difficult Childhood 30:56 Becoming the Parent You Needed 31:53 Balancing Ambition and Family Life 33:32 Evolving Into Your Next Chapter 35:54 The Power of Being a Connector 37:55 Scarcity vs. Abundance Mindset 39:47 Check Your Ego at the Door 41:56 Staying Grounded While Winning 43:03 The Strength of a True Partnership 45:28 What Makes a Truly Great Idea? 46:42 What Makes Someone Worth Betting On? 48:39 Learning to Slow Down and Reflect 50:32 Finding Joy in the Present Moment 54:53 David in Final Five Episode Resources: Website | https://groothospitality.com/ Facebook | https://www.facebook.com/davegrutman/ Instagram | https://www.instagram.com/davidgrutman/ X | https://x.com/DaveGrutman https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

David GrutmanguestJay Shettyhost
Apr 8, 20261h 2mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:07

    Intro

    1. DG

      I never thought in a million years I'd be a cameo in a Super Bowl or have a restaurant. People think, "Oh, you're just killing." But anything you can imagine messing up, I've messed up. The only thing I try not to mess up is relationships. If I'm your friend, I'm gonna push you so hard. But if you're bad to me-

    2. JS

      Hey, everyone. Welcome back to On Purpose. I know that you guys love being entrepreneurs. You love trying to find new entrepreneurs that you can follow, learn from. Maybe some of you are inside companies and you wanna build within them, or maybe you wanna quit your job and start something new. If any of those are true for you, this episode is for you. Today I'm joined by David Grutman, the entrepreneur behind some of the most successful restaurants and nightlife venues in the world. If you're trying to build a business, grow your career, or create something that stands out in a crowded world, this episode is packed with lessons you won't wanna miss. Please welcome to On Purpose, David Grutman.

    3. DG

      Ah.

    4. JS

      David-

    5. DG

      Thank you

    6. JS

      ... congrats on an incredible career so far. Congrats on an amazing book.

    7. DG

      Thank you.

    8. JS

      So excited to dive into your mind.

  2. 1:075:06

    Why You Should Take It Personal

    1. JS

      And I thought the best place to start was with the title because I thought Take It Personal almost feels like the opposite advice that everyone always says.

    2. DG

      Right. Doesn't everyone say, "Don't take it personal"? I think it's because of how deep I take it. I- Like how much I care about your experience, how much I care about the person, how much I care about that relationship. And if you care that much, there's no other choice but to take it personal. And it's, it's part of my success.

    3. JS

      Yeah. I, I find that... When was the first time you realized that it was good to take it personal? Because when you're growing up and if you're failing, everyone's like, "Oh, don't take it personally." If you got rejected from that company, "Don't take it personally." Or if, you know... When, when did you realize that actually the opposite was right?

    4. DG

      I realized when I started making m- mistakes. When I started, you know, when I first started my career and the general manager would come at me so hard and would be so upset. That's when to me it really resonated with me, and that showed me that this is how I change, how I make, how I'm able to get better was because of how deep inside it, it hurt me. That's where the real change happened. But when I started my career and I would... You know, because of being young and just l- learning the business, when I really messed up, they really came down on me. I was just like, "Ugh." I never wanna disappoint anybody, but the best lessons I've ever learned was when I made mistakes, even today.

    5. JS

      What, what was the biggest mistake you made back then that they came down hard for you?

    6. DG

      I mean, Jay, come on. I've, [laughs] I've yelled at people when I was, like, a manager. I'm like, "You can't yell." I've, like ... 'cause of insecurities. I've, I've just messed up ev- anything you could imagine messing up in my life, I've messed up. The only thing I try not to mess up is relationships. I went to make a money drop, and it got stolen out of my car. I've given bad change. I've closed out wrong. I've forgot to lock this. I've done... When you make a mistake and someone is like... y- you could see that someone's very angry with you, I'm just like that. And then later on in my career, because I focus so much on these relationships, when they don't go to my place and they go somewhere else, that's where it really goes south.

    7. JS

      Yeah. Yeah. Yeah. But when I'm hearing this, people coming... A lot of the time when people come down hard on us when we make a mistake, we almost feel like we don't deserve it, right? But you're saying that you saw it as care?

    8. DG

      When people take the time to really get upset with me, at that time, I probably took it as, "Wow, they really care about me."

    9. JS

      Yeah.

    10. DG

      Which made me even worry about it more. Now, as I grow in my life, people would always say to me, "Don't take it personal. Don't worry about it. Da, da, da." And I'm always like, "What are you talking about, man? Person's not coming to my place. They're going next door. That's, that's an issue for me." And I try to really put my t- around my team, I'm like, "Guys, your- why is your friend doing their birthday party at another restaurant? Why is this person that we take care of all the time hanging out at that nightclub? If I don't take it personal and you don't take, and you don't take it personal, we're never gonna win." So my team really c- come... They'll call me and be like, "Just so you know, I'm taking this one personal, David."

    11. JS

      [laughs]

    12. DG

      And I'm like, "Great. I love that."

    13. JS

      Yeah. I like it as a mantra. I like it as a reframe right now.

    14. DG

      And I think it just keeps evolving too. Like, I want people to really know that it hurts me personally. I want you to think about it for that split second if you choose another restaurant over mine, Dave's gonna get upset with me.

    15. JS

      [laughs]

    16. DG

      I want them to, to kinda know that. So at least there's a, at least a l- more thought if they don't go to one of my spots.

    17. JS

      Yeah. Yeah. Now I, now I need to be careful in Miami when I'm next there.

    18. DG

      Oh, no. Just so you know, wh- when people come to Miami, I'm tracking you like an endangered species.

    19. JS

      [laughs]

    20. DG

      I'm like I'm watching everything you're doing. Oh, okay, that's where they're going. Okay.

    21. JS

      I see where you are, yeah. That's hilarious. I love that.

    22. DG

      And friends of mine that open restaurants in Miami and stuff, they're like, "I, I hope you give this person the warm welcome you gave me," 'cause I was like, "You're not going there."

    23. JS

      Yeah, yeah.

    24. DG

      And whatever, but, you know. As I get older, I, I want other people to win too, and I, and... But still, I take it-

    25. JS

      [laughs]

    26. DG

      I get really upset, Jay, if you go somewhere else.

    27. JS

      That's brilliant. I love that mentality. It's

  3. 5:067:11

    The Small Details That Make People Feel Seen

    1. JS

      so cool. When, when you started out as a bartender, you s- you said you made a lot of mistakes, but do you think you had a skill or an ability at that time that's made you successful today?

    2. DG

      Yeah. Definitely my interactions with people and remembering their drinks and having the drink waiting for them when they would j- when they were walking in and stuff like that. I think the little things that you make people feel seen and cared about is what really matters. Even bar- like bartending, listen, what I loved about it is that I love to serve people, and I think serving even at the bar is like the greatest. When you make them a cocktail they never had or just by having their drink that they, that they love having there and having the one-on-one conversations with people really helped me build relationships.

    3. JS

      What, what made you do that then? You say this in the book. You're like, "I didn't know when I started out that I was ever gonna build this empire."

    4. DG

      Ever.

    5. JS

      But you had that mentality then. Like... And obviously, I'm guessing you weren't getting paid incredibly well.

    6. DG

      No, no, no. I was-

    7. JS

      Oh, okay. Okay

    8. DG

      ... so, so I was making $100,000 a year bartending at a restaurant in the mall

    9. JS

      How?

    10. DG

      Because these gol- these guys would come off the golf course, give me $100 tips, all this kind of stuff.

    11. JS

      So it was in tips you were making most of your money?

    12. DG

      Yeah. And I really loved to see the managers working and the maître d' and all that. I'm like, "I wanna be a manager." And they're like, "Well, that pays 33 grand a year." And I was like, "I'll take it." [laughs]

    13. JS

      [laughs]

    14. DG

      I-- 'Cause you don't care. Money's not your, your end goal, and investing in yourself, too, it matters so much. And I was so excited to be that manager on the floor. And let me tell you, these people had experience for 20, 30, 40 years, some of these servers and stuff like that. H-how am I gonna be the one that's gonna lead them in making sure they do everything right? So education's really where I focused in on, really taking the time to, for my server meeting each day, bringing pamphlets and port wine with chocolate cake and letting them sample and saying it's a for- And, like, giving them all the information on what that port wine. It's a fortified wine. It's from Portugal. It pairs well with this, this, and this. You guys taste it all. That's how I would kind of connect with people.

    15. JS

      I, I can honestly say that when there's a good maître d' or a good manager at a restaurant, you feel the difference. Like, you absolutely feel the difference. Where were you

  4. 7:117:59

    The Real Path to Self-Improvement

    1. JS

      learning these skills from?

    2. DG

      I was lucky enough to have one of the owners of one of the first restaurants I was managing at was a guy named Burt Rapaport, and he made us go to, like, Seven Habits of Effective People and always looked for how, how can you do self-improvement? And I had great general-- When I was a young manager, I had great general managers that were like, you know... I always had this imposter thing that like, why am I a manager managing someone that has this kind of, kind of crazy experience over them? And that's-- And I see it now when I see managers yelling or screaming or whatever and not handling situations well, it's because they're not confident where they are at in life. And it's funny that now I know I'm much scarier by not screaming.

    3. JS

      Mm-hmm.

    4. DG

      But you have to look deeper than that. You have to see why are they reacting like that? W- 'Cause they wanna be a great leader, and they care about people, but why is it coming across like that?

    5. JS

      How did you

  5. 7:599:06

    Turning Anger Into Growth

    1. JS

      transform your anger? 'Cause I feel like that's a natural reaction when you're new in business. You wanna get things right. You don't wanna let people down.

    2. DG

      And even now, I'm so de- Like, if I-- the music's too loud, the lighting's off, or I'm looking over... Like, either my friends really like going out to dinner with me, or they hate it, 'cause I'm constantly looking at, like-

    3. JS

      At other people's restaurants or your own?

    4. DG

      No, no, at my own.

    5. JS

      Oh.

    6. DG

      Just I'm looking at the thing. I'm like, "Turn the music down. Turn it up. Light, da, da, da. Oh, this server's not waiting on them." I, I'm looking at all the details. And a lot of my friends, they really enjoy 'cause it's like-

    7. JS

      Yeah, it's fun

    8. DG

      ... yeah, it's fun.

    9. JS

      To learn, yeah.

    10. DG

      And some are just like, "Can't you just focus on me?" And I'm like, "Then we should go somewhere else."

    11. JS

      [laughs]

    12. DG

      "Because I can't focus on you, really, in my own place."

    13. JS

      [laughs]

    14. DG

      And then I realized because of that, the, the bad effect of that is s- it tightens everybody up more because they know I'm watching, and I don't want them to choke, and I don't want them to be uncomfortable at work, but I just can't help myself. I'm not the kind of entrepreneur that r- that takes all the notes and then sends a nice email out the next day. I want things fixed right away. I want, like, real time situations, and I think in the hospitality business, you only get so many opportunities.

  6. 9:0611:20

    How to Give Feedback That Actually Works

    1. JS

      What, what have you learned about giving people feedback that wins versus feedback that demoralizes people?

    2. DG

      People close up when you just torture them, but also, you know, the emotional bank account is something that is... People kind of joke about it, but the emotional bank account's a real thing. You can't just say, "Bad, bad, bad." You have to say good things too, 'cause you just don't wanna be in the red every time you go to that person. So taking that time, say, "You know what? Great job on that. Oh, I saw you, I saw the p- face on th- that person," or little wins like that that... And it's so hard when you're an entrepreneur to just talk about the good things, 'cause all you wanna do is talk about the bad things, right?

    3. JS

      Yeah.

    4. DG

      But taking that time to make sure it's... 'Cause once you're in the black, you could, you could take some out of the deposit, you know?

    5. JS

      Yeah, yeah.

    6. DG

      Uh, that helps a lot. And to be calm. I used to be like, "And what were you thinking, and h- what's the thought?" You know, I, I, I used to always wanna know what was the thought process of you making that mistake? Where would you think, where did you think that was gonna be the right way to handle it?

    7. JS

      Yeah. And that didn't work.

    8. DG

      It just is like, come on, now you're demeaning me. The, let's just say, and be specific. I'm always very specific with what I saw was wrong. It's not vague and like, "You know, maybe, kind of, I s- I think, you know, in this w-" "No. You, you order fired the entire meal. You didn't pace it out at all. You ruined the guest experience. They, they're gonna feel like they got pushed out of their pl- out of our place. Is that how you wanna be taken care of?" No. I'm very specific. You know, Mark Cuban, one time, I took him in the DJ booth, speaking of this. He goes, "Do you ever take a moment to really appreciate what you've done?" And I'm like, "No, Mark, what are you talking about?" I'm like, "Da, da, da, da. Of course not. Who takes the moment to appreciate? I'll do that later on." He goes, "No, no, no. Take the moment, man." And I try now. Kind-- I'm like, when it's like, when I know it's good, I'm just like, "Ah." It feels good.

    9. JS

      Yeah.

    10. DG

      But in my business, you live, every day is a new day.

    11. JS

      Totally.

    12. DG

      It's like... And this is where my competition goes wrong a lot. They just go, "Okay, we hit it out of the park." But there's tomorrow, and they forget about tomorrow.

    13. JS

      Yeah. Yeah, 'cause, because people are eating every day, you're only as good as your-

    14. DG

      Nightclubs are going-

    15. JS

      ... last event

    16. DG

      ... every DJ.

    17. JS

      Yeah.

    18. DG

      There's a new DJ every week. I mean, it's, there's always something that's, someone's, you know, trying to beat you to the punch on.

    19. JS

      Yeah.

  7. 11:2012:52

    Creating a 10/10 Customer Experience

    1. JS

      Talk to me about how you get the confidence to even go, "Well, I'm gonna start my own," because that's not easy.

    2. DG

      So it's not easy. I, um, once I started taking over major club venues and feeling very confident on knowing the workings of that, did I start thinking like, "Well, I really wanna just be an entrepreneur. I don't wanna turn the needle for other people and not share in it." It's advice I tell a lot of my celebrity friends and friends that are, they take fees. They're, whatever. And I, I understand that people have to live, but I think if you're gonna turn the needle for someone, you better have some equity in that brand too.

    3. JS

      Mm-hmm.

    4. DG

      And it's always better to take equity than just a fee for hire.

    5. JS

      Mm-hmm.

    6. DG

      But when I made that move, I started a company with two other partners. First, it was a marketing agency, because all these brands were coming to Miami, 'cause there was the VMAs, there was all sorts of marquee events.And these brands wanted to be treated like they do in New York or LA, serviced the same way. So I started that company. We sold that company. That company went bankrupt. I got the company back, and then I s- put restaurants and night... and everything in it, and I sold 51% to Live Nation right before COVID.

    7. JS

      Mm-hmm.

    8. DG

      But taking that first step of opening your own company, it's the best feeling ever. But to this day, people think, like, you know, "Oh, you're just killing it," but you have to make sure everyone else is first, and you're the last one as you, as you know to get paid. And there's some months that you don't get paid at all. People don't realize that, you know. They all just see, "Oh." And even when you're losing money, you still have to pay.

    9. JS

      What was the difference in the

  8. 12:5214:33

    Every Day Is a New Opportunity

    1. JS

      approach, the strategy, the mindset that actually allowed you to go and sell 51% of your company to Live Nation day before COVID, versus the guy that you grew up with who was a bartender, who was a manager that wanted it, too?

    2. DG

      Or what about the guys that were right next to me as I'm doing it that think that, you know, that just because you went and did it all, that they think they should be the same as you?

    3. JS

      Sure.

    4. DG

      That's the hardest part ever, too, right? So you have to convince yourself first that this is what you, this is what your goal is. If I'm in the hospitality business, don't always wanna just be a... I wanna, I wanna be that owner. I wanna, I wanna open that place. Uh, of course, it's a lot of ego, I'm sure, as you can imagine, and, uh, it's just growing. I think that I have ADD so badly that I, once I've hit that thing, I wanna, "Now what else can I do? What else can I do?"

    5. JS

      Who was the first person you had to convince?

    6. DG

      Komodo, I had to raise $10 million for Komodo, and my friends, they were like, "Listen, man, this is a big space. This is far away from everything. We're gonna do it, but we're kinda doing it just to, like..." And it turned out to be one of the greatest things I ever did, but it didn't start out great. I had to really push hard, hard, hard and convince people to come and see me at this restaurant. If you wanted to hang out with me, you'd have to hang out with me there. Any DJ that was playing at LIV, I'd make them go have dinner there. Any celebrity that came to town, I made sure we did a big dinner there. But I also focused on the other details, the food, the atmosphere, the vibe, the energy, everything, was a real hyper-focus for me that when people would come, that it was the best experience over. And then it became, uh, one of the top independent restaurants a couple years ago.

    7. JS

      That was... But that you built after building LIV, right?

    8. DG

      Yeah.

  9. 14:3316:27

    Building Something From Nothing

    1. JS

      What was your first ever restaurant that you, like, first foray into hospitality ownership?

    2. DG

      So, uh, I had run a nightclub for this, these guys, the Oak Beach Group, for many years, and it was f- so successful, but they wouldn't make me a partner.

    3. JS

      They wouldn't?

    4. DG

      They would not make me... I'm like, "Give me a piece. Come on, anything." Uh, they went, and this other club group did. They were opening a new club. "Okay, David, you're gonna be the, you're gonna be a partner with us," da, da, da. Everything I did was to try to make those other guys s- regret the fact that they didn't, [laughs] they didn't give me a piece. Because my ethics and my belief system was not lined up, I failed so bad, Jay. It was, I would throw the kitchen sink. I would do Christina Aguilera's birthday, and Kim, and da, da, everybody you could ever imagine. And everything I was doing was like, "Ah, they're gonna, now they're gonna regret." Yeah, they regretted that I failed so badly they bought the club from me.

    5. JS

      No.

    6. DG

      Oh, yeah. So when I, when LIV opportunity came, I said, "You know what? I'm not gonna worry about anything. I'm just gonna do what I do, and I'm gonna do it really, really well." And that's LIV.

    7. JS

      How did that opportunity come your way?

    8. DG

      So at first I was gonna partner with this guy from Las Vegas that was gonna open up a club there, and I was gonna be his partner, and he got into a little bit of trouble. And Jeff Soffer said, "Listen, I just wanna do it with you. Let me, let's just do the club together." And I'm like, "Okay, let's do it." And I said, "I wanna do things, I wanna do Vegas-style hospitality," 'cause Vegas was known for the service and the hospitality, and I wanted to bring that to Miami.

    9. JS

      Hmm.

    10. DG

      And everyone was like, "It's too far up. You're never gonna make it." But Jeff Soffer, who owns the Fontainebleau, was building the first Las Vegas-style resort-

    11. JS

      Yeah

    12. DG

      ... in Miami, where you had restaurants feeding the nightclub, and 1600, you know, insane amount of rooms, and just a, a whole, like, landscape that you don't wanna leave.

    13. JS

      Hmm.

    14. DG

      And I really believed in it, and it was, it's turned out to be one of the greatest experiences of my life.

    15. JS

      It seems like you built

  10. 16:2719:51

    The Power of Genuine Relationships

    1. JS

      these incredible relationships from starting out as a bartender-

    2. DG

      Yeah

    3. JS

      ... manager, owner when it failed, owner when it succeeded. A lot of people feel like when they're not the owner, they can't build good relationships.

    4. DG

      Oh, you know how many times I hear that? "Oh, I need a business card. I need a title. I need this, I need that." I go, "I never had any of that stuff, by the way."

    5. JS

      So how did you do it?

    6. DG

      Because I always felt like I should be that person to have that relate- And I always asked stories, and I always walked like I had a destination, and I always believed in myself that, like, of course these people need to, I need to take care of these people. And I think when you're trying to add value to people, y- you have a different kind of stance than you do when you're trying to, like, take things from people. For me, I just wanted to add value and make people have the best time of their lives at my spots, whether I was a manager, a general manager. I say it all the time to my team, "You know, listen, in the hospitality business, a lot of people are using it as a transition job bef- be- before they get to where they wanna be." And I'm like, "Listen, if you wanna be a doctor, a lawyer, whatever it is, if you're a professional here, you're gonna be a professional whatever you do, and you might as well start being a professional right now." And I think by being a professional everything, it's part of your DNA. It's not like, "Oh, once I become successful, then I'm gonna start acting like that." That's, like, craziness.

    7. JS

      Yeah, yeah. And, and I think y- you hit the nail on the head with the idea of if you don't have a title yet or you don't, you're not an owner, if you truly wanna make everyone else's night or add value, then you don't feel scared. You only feel scared when you're like, "What can I get from them?"

    8. DG

      What can I extract from the relationship?

    9. JS

      "What are they, what are they gonna do for me?" And I think when you walk into a space, obviously the person who's the person you wanna network with is just gonna walk away, because they, they get a million people who wanna take from them.

    10. DG

      And, and I talk about this in my, in, in my book.

    11. JS

      Yeah

    12. DG

      At these dinner tables with like a celebrity or a power of business, if I didn't talk to everyone at the table, I wouldn't be here.

    13. JS

      Yeah.

    14. DG

      If you just focus on that one person, you're never gonna, you're never gonna succeed.

    15. JS

      Yeah.

    16. DG

      And I, I, I guess you're right. I guess, you know, coming at it where I'm just here to ha- make you have a great time, I'm not trying to extract anything out of it, you, your, you have a, your confidence level's a little bit different.

    17. JS

      Yeah. I remember... You reminded me, I went to an event a few years back, and it was, it was for a particular individual, and I won't get into the details, but the point was everyone was there for this one person, and that's why everyone was invited to the event. It was at a friend's home. It was private. Maybe there were 30 people there, but the person who it was for only spent time with who they believed were the top five most important person-

    18. DG

      Ah

    19. JS

      ... people in the room, and they ignored 25 people. Now, granted, visually, those five people were the most important people in the room, but you don't know who the other 25 people are.

    20. DG

      Right.

    21. JS

      Like, you have no clue. And the other 25 of us, who were not the most five people in-

    22. DG

      Right

    23. JS

      ... most important people in the room, kind of just walked away just thinking like, well, if you can't give your attention to 30 people, how are you gonna take care of like, you know, 300 million people at one point? So, you know, it's, it's a fascinating idea that I think people underestimate.

    24. DG

      And making the whole table feel special is so important. And by the way, I wanna know everyone's story, and those relationships from back then I still have today. And what people don't realize is, "Oh, it's just the manager. Oh, that's the agent." Oh, yeah? That agent controls 10, 20 great people that they're gonna send your way, or that publicist, whatever, and it's just like... But knowing that, even like, you know, some of these people have their best friends with them their whole lives, and they try- Hearing the best friend's stories-

    25. JS

      [laughs]

    26. DG

      ... is always like, wow.

    27. JS

      Yeah, yeah. Yeah, you get better stories out of them. Yeah.

    28. DG

      Way better.

    29. JS

      Yeah, yeah.

    30. DG

      So it's, to me, it's always about people.

  11. 19:5122:28

    Does Networking Actually Work?

    1. JS

      Yeah. What's a rule about people that you've learned that you think people don't understand, that most people don't, that most people miss?

    2. DG

      They go into it with some kind of, I don't know, agenda. I go, "Don't have an agenda." Just see what it's gonna be and if... what you can add value to, how you can help that person. Because by being a key holder of Miami, people are coming to spend a few days, and they wanna have a great time, and they wanna enjoy, but they, but it's also I want them to know how great my city is. Miami's the best city, I feel, in America, and I wanna show that to them. So I would take people to the art district, to this district, or this cool little restaurant that's not mine but has the, the, this insane whatever. And I love hosting people at my house.

    3. JS

      Why is that important?

    4. DG

      'Cause I feel like the relationship when it's, when you're in someone's... In fact, I do all my meetings, Jay, at my house. Like, I have a great office, and there's a lot of people working. I'd much rather meet with you in my house than in an office setting.

    5. JS

      Yeah. I'm the same. That's why you're here right now in my house. [laughs]

    6. DG

      By the way-

    7. JS

      Yeah, yeah

    8. DG

      ... not a bad house.

    9. JS

      No, but it's, it's the same feeling of like... I, I love hearing that from you because so when I... First when I moved to the States, I lived in New York. I was there for two years.

    10. DG

      Right.

    11. JS

      And then we moved to LA eight years ago, and we've been in the US for 10 years now. So the two years in New York, I found that I spend a lot of time meeting people in restaurants-

    12. DG

      Ugh

    13. JS

      ... bars, things like that. As soon as I came to LA, I met someone at their house, and I was at their house for like eight hours, and I was like, "Gosh, I would never have spent eight hours." And it wasn't like the people were better. It was that spending time with someone in their home felt so much more intimate and deep than spending time in a bar for one and a half hours.

    14. DG

      I couldn't agree more. When you, when you spend time with per- people in your house, it's kinda like why they built the White House.

    15. JS

      Yeah.

    16. DG

      You want them to feel like... A- and I feel like it's an edge too. Listen, when you're in... Once you have a personal relationship with somebody, it's much harder to say no to that person.

    17. JS

      Do you try and make your places feel like home?

    18. DG

      I really care about people's hospitality from the moment they walk into my house to the end. I mean, we have great food, great drink. I'm always caring about what, what can I get you to drink, what can we get you to eat, and, and knowing what their likes are too before they even get there.

    19. JS

      Do you think that you think about a good restaurant and a good club as also feeling like a home, or it's a different mindset?

    20. DG

      Different mindset. I think-

    21. JS

      How would you... Yeah.

    22. DG

      I think your home is your home. Uh, but restaurant people wanna be serviced, but I don't want them to feel like they're over-serviced, where the person's on top of them, they can't have their own experience. I think that's where some people think great hospitality and great service is just every second on-

    23. JS

      Mm-hmm

    24. DG

      ... I think people want seamless service, and they wanna create their own experience.

    25. JS

      Yeah. Yeah, yeah. I couldn't agree with you more.

  12. 22:2826:50

    How to Play the Long Game

    1. JS

      You've partnered with so many massive names. I mean, I know you launched with Bad Bunny.

    2. DG

      Sure.

    3. JS

      And that's incredible. Talk to me about how that partnership came around.

    4. DG

      Again, long ball, long ball. I just love, like, l- long-term relationships, and you know, uh, we started a reggaeton night at LIV when it was just starting to bubble, and this guy Bad Bunny had so much engagement back then. It was, to me, I never... The only other time I saw that is when Abel first came on the scene and we started doing stuff with, with The Weeknd.

    5. JS

      Yeah, yeah.

    6. DG

      The engagement that people... This is before he was like... People were like, 3,000 people would show up for this guy The Weeknd at the club, and same thing with Bad Bunny when we first... I'm like, "There's a guy named Bad Bunny?"

    7. JS

      [laughs]

    8. DG

      And then I became friendly with him. Drake comes down to s- to film his, to record his album Scorpios. I'm having dinner with him, and he goes, "Who's the number one reggaeton guy?" I'm like, "Dude, this guy Bad Bunny." He goes... I DM him. He doesn't respond to me. I'm like, "You sure you have the right Instagram for this guy?" I get his manager on the phone. His manager puts him on the phone with Drake. They do- He says, "Listen, either you're gonna come here, or I'm gonna go there." Bunny comes the next day with the whole team. They don't believe it's real. Everyone has promised him Drake. I'm like, "Listen, man, I'm not... [laughs] I'm just trying to help. That's it." They come to my house, waiting for Drake to call. Drake's manager calls and says, "Listen, he's not gonna see him tonight. He has to go do something else." I go, "What are you talking about? They're all in my backyard, man. They don't believe it's real. They might kill me." He goes, "Nope. Tomorrow." They get up. They leave. Couple minutes later, the other manager calls, the day-to-day. He says, "Listen, Drake wants to have dinner with him at Komodo th- that night." They all come. They go to Komodo Lounge, and then they record Mia.

    9. JS

      No.

    10. DG

      So Mia, Mia.

    11. JS

      Yeah, yeah. Of course, yeah. It's a great song.

    12. DG

      Drake's album comes out, no me on the album. I go, "Oh no, they did the song. He's not g-..." They go, "Don't worry, David, Bunny's gonna release it, not Drake, and they wanna release in the summer." They release, the song's a huge hit.

    13. JS

      Huge hit, yeah.

    14. DG

      They do the music video in Miami when he's, Drake's supposed to do, like, three days in Miami. It rains, Drake gets sick, cancels his show. Anyway, the song, they get the video, the song comes out huge. Later on, Drake's has to make up those shows, comes back to Miami. I go, "Why is Bad Bunny not coming out with you at one of your shows?" He goes, "He should come out." Again, I get to Bunny, and, and Noah saw his manager on the phone, and I go, "Noah, listen, Drake wants Bunny to come out with him at his show. I think he should do it." He goes, "No, no, no. His manager already told me he doesn't want him to come out. He doesn't wanna sing Spanish or anything like that." Drake, here you go. Can you guys come? They just landed in Vegas for the Grammys. They get back on the plane and come and go out with him on his show. So fast-forward, Live Nation, Michael Rapino, who runs Li- is the greatest human being partner ever, goes, "I wanna make Latin like I did with hip-hop with Roc Nation. I wanna do that with Latin." I go, "Well, let's start with the top." So he does this deal with Noah Assad at JV about bringing Latin acts to Live Nation. Bunny moves over and does a stadium tour with Ro- with Live Nation, and he puts in his contract, he says, "Okay, one other condition, if for me to do this is David Grutman does a restaurant with me."

    15. JS

      [laughs]

    16. DG

      So Michael Rapino calls me and I go, "Come on." Are you like-

    17. JS

      'Cause you were just hooking them up anyway. You're not, yeah, yeah

    18. DG

      ... Yeah, I'm like, "I'm so happy. I'm so happy-"

    19. JS

      Yeah

    20. DG

      ... "that, that you guys are... This is great." He goes, "No, no, no. I need you to do this restaurant." I go, "Okay." Meanwhile, it's been the greatest experience and relationship between... Also, so there's Bad Bunny, but there's a guy named Noah Assad who's his manager, who I just, I love them both so much, and it- it's such a family.

    21. JS

      And talk to me about the timeframe between you connecting him to Drake and that happening to the restaurant.

    22. DG

      Probably, like, three years, fi-

    23. JS

      Yeah.

    24. DG

      Yeah.

    25. JS

      Yeah, yeah.

    26. DG

      Just, but constantly.

    27. JS

      Yeah. And, and that's the thing, you were setting them up when there was no benefit. You're not, you're not in on the deal. You're not making music.

    28. DG

      Oh no, I'm not an executive producer of the song.

    29. JS

      Yeah, yeah, yeah.

    30. DG

      In fact, nobody even really knows.

  13. 26:5029:30

    The Truth About Real Success

    1. JS

      man. No, uh, but, but I'm, I'm, I'm glad that the lesson is the long game because I think people underestimate-

    2. DG

      Oh

    3. JS

      ... people underestimate the power of that. I think there's such a transactional quick-win mentality now, believing that you've gotta... You know, and, and also even pretending for amounts of time to see what happens. Even that is not long game. Long game is just building loyal relationships.

    4. DG

      By the way, that's it, and I, you know-

    5. JS

      Yeah

    6. DG

      ... people say to me, "Oh, I wanna go network." I'm like, "What the f- is networking, man?" I go, "Networking is the worst thing. I wanna go have authentic relationships with people."

    7. JS

      Yeah.

    8. DG

      And you're right. I see it today all the time. They just wanna, like, what's the quick hit to do? And I'm just like-

    9. JS

      Yeah

    10. DG

      ... "Man, take the journey with people."

    11. JS

      Totally.

    12. DG

      "Go the distance. You never know." I never thought in a million years I'd be a cameo in a Super Bowl or have a restaurant or that the guy that just partnered with me is trying to get Latin, I'm able to. Now Live Nation's the biggest in Latin.

    13. JS

      Yeah.

    14. DG

      And I'm so happy. It's like-

    15. JS

      Yeah, and that was all just stuff that was fun. It was just, yeah.

    16. DG

      By the way, and that's what I've also learned from Michael Rapino is, you know, listen, let's just, just go about it and things might come out. And by the way, sometimes nothing comes about it, and that's okay too.

    17. JS

      Yeah, yeah.

    18. DG

      But you have these stories with people.

    19. JS

      Yeah, totally. Totally.

    20. DG

      Like, it doesn't always have to be about a monetary situation.

    21. JS

      Yeah. Yeah, I couldn't agree with you more. I remember when I was, I was just starting out my career, and I became friendly with this guy who was around, at that time, he was, like, 70 years old. He was a jewelry designer, and his dad used to play harmonica for Frank Sinatra.

    22. DG

      Wow.

    23. JS

      So he had loads of great stories of being in the car with his dad and Frank, and-

    24. DG

      Wow

    25. JS

      ... they would travel across the world and, you know, be in the back of a, you know, a bus, tour bus, I guess. And then he'd have all these stories. He designed jewelry, and the jewelry would end up on the front cover of, like, Vogue and Victoria's Secrets and all that kind of stuff. That was his career, and he'd have all these stones he'd find from Africa, and he'd tell me stories about where he just went in Africa and found this, like... And I, I would watch him, and I was probably, like, 26 at that time, and this guy's, like, 70. And I would just be like, "God, this guy's got so many great stories." And, and I used to just sit there and watch him and go like, "God, when I get older, I hope I have lots of stories." 'Cause I thought, what a cool life to live.

    26. DG

      Yeah, I mean, I, I, I mean, and I love that my kids now get to have these relationships with these people, too, the n- the next generation. Like, my kids have no idea that this is so-and-so and this is so-and-so, but they're getting to meet some of the most amazing people that've changed our world.

    27. JS

      Yeah.

    28. DG

      And, and, you know, whether it's not just celebrity, it's also business and it's... And from, and my wife, too, like, to, for us to be around these kind of people is, is great. And-

    29. JS

      Yeah, yeah

    30. DG

      ... I love it.

  14. 29:3030:56

    Lessons From a Difficult Childhood

    1. JS

      your childhood like?

    2. DG

      Difficult. I was, my parents got divorced when I was six. Uh, I was l- only child, left alone a lot by my mom when she'd be in real estate and stuff like that. And my father instantly remarried. She had a kid from another marriage. So for me, I'm like, my dad moved on with a new family. I'm here left alone by myself a lot. I grew up with, like, Silver Spoons and Family Ties and Different Strokes and Facts of Life and Charles in Charge. That's kinda, like, how I was raised.

    3. JS

      Mm-hmm.

    4. DG

      So it's a little weird. And then when I got older, I was kinda like the stovetop kid. I'm like, "What time are you having dinner? What time are you having dinner?" But I grew up in Naples, Florida. It's a really, uh, beautiful space to g- um, place to grow up. A lot of retired people, so a lot of my friends, you know, they're dead. They were 90 years old back then. No, I'm joking. But it also-

    5. JS

      [laughs] I was like, "Yeah"

    6. DG

      ... no, but you know what is, by being an only childYou're able to have conversations with adults-

    7. JS

      Mm

    8. DG

      ... 'cause you're around more adults than you are children.

    9. JS

      Mm.

    10. DG

      And I kinda love that about my childhood. It's one thing I will never like... I loved being able to learn from just being able to be in the room with older people at the time.

    11. JS

      Yeah. I couldn't agree with you more. I think it's a huge one. It's probably the hardest thing right now, where people are spending less and less time with people older.

    12. DG

      'Cause my daughters are 18 months apart, so they're, they have each other.

    13. JS

      Mm-hmm.

    14. DG

      And they're always around each other. But I was the guy that was, the kid that was in the room with, like, all the adults and hearing the adults' stories and stuff like that, and it still fascinates me today.

    15. JS

      What are the lessons

  15. 30:5631:53

    Becoming the Parent You Needed

    1. JS

      that you learned from your parents that you're trying to pass on to your kids? And what are the lessons you're trying to avoid?

    2. DG

      So I never n- uh, because I was the... I probably blame my mom and my, my father pa- but I, I, I'm not as connected with my family as I, as I want my kids to be connected with me.

    3. JS

      Mm.

    4. DG

      And I, like, make sure I have that connection with them. And I want them to grow up in a loving, loving family. Not that my mom didn't love me, I just never felt super connected because I saw her late, and I didn't understand why these other kids were able to have these families and all that, and I probably blamed somebody for it.

    5. JS

      Yeah, yeah. And that, when did you feel like you stopped blaming or you stopped connecting to that?

    6. DG

      I don't know if I, uh, if I ever... I just feel like I never want my girls to grow up like that. I want them to always feel love and, and a presence around them all the time.

    7. JS

      Yeah.

    8. DG

      Now, and again, my mom loves me, but I didn't get to see her much, but I want my girls to always see me. We take them with us everywhere.

  16. 31:5333:32

    Balancing Ambition and Family Life

    1. JS

      How do you manage that with the crazy lifestyle you have and-

    2. DG

      We manage it. We make it a priority, and, like, that's part of our life. Like, that's kind of the deal. If you have us, our kids are coming too.

    3. JS

      Yeah.

    4. DG

      I mean, there's things for everything, but, you know, taking my kids to Saudi Arabia, taking my kids to Israel, taking my kids to Japan, it's like, it's the coolest thing in the world, and seeing them, how excited they get.

    5. JS

      Yeah. How do you f- how have you pivoted? 'Cause I feel like you're also brilliant at knowing when to start something new.

    6. DG

      So, like, last few years, I knew investing in brands and working with young, young entrepreneurs, young founders that I could make a big difference in, has been really the, the next stage of my life.

    7. JS

      Mm.

    8. DG

      And I, and I, and I love it. And how can I take those brands and put them into my ecosystem and grow them then?

    9. JS

      Give me an example, El.

    10. DG

      SkinnyDipped, uh, the, the-

    11. JS

      Yeah

    12. DG

      ... it's probably the best better for you till cover nuts out there.

    13. JS

      My wife loves them.

    14. DG

      They're the greatest, SkinnyDipped.

    15. JS

      Yeah, yeah.

    16. DG

      So I have a SkinnyDipped dessert at some of my restaurants. Uh, dairy and plant-based chicken I would have, you know, at my places. I do collaboration dishes with Fly By Jing or all these different things, and I think that's one way of adding value. I've done noodles, mac n ch- help, you know, better for you mac and cheese balls, and all sorts of stuff, and brunches all cater to these brands, or events just cater to these brands to grow them. And then I talk about them a lot. And I ha- and we rebrand, and we do collaborations, and other brands I invest in, like Symbiotic and Coconut Cult, I have them do collabora- all different stuff. But by being this great connector for these brands and young founders, it's been the most rewarding thing I've ever done.

  17. 33:3235:54

    Evolving Into Your Next Chapter

    1. JS

      That seems to be like, with all these stories you're telling me, there's a pattern in who you are, which is, like, this super connector.

    2. DG

      Correct.

    3. JS

      Right?

    4. DG

      Yeah.

    5. JS

      It feels like that's your superpower.

    6. DG

      I love that I'm able to get anyone that I really need to get on the phone, on the phone, and n- and put them with somebody else, and they know that there's no... I just wanna help.

    7. JS

      Mm-hmm.

    8. DG

      And that's why people take the call and do, and do what- whatever they want, and they do great things together, and I'm not the guy where, "Oh, can I get 10%?" Like, I hate those people. But it pays off 10 times over. So, like, don't be so hungry for that one... If your friends do a great deal, be so ha- cheer your friends on.

    9. JS

      [laughs]

    10. DG

      I'm like everyone's biggest cheerleader.

    11. JS

      Yeah. It's fascinating, isn't it? Like, we've, we-

    12. DG

      [clears throat]

    13. JS

      ... so many people are living in that scarcity mindset of being scared that if I connect you to you, and then you guys do business together, then me-

    14. DG

      I'm gonna get cut out.

    15. JS

      Yeah. Yeah, yeah, exactly.

    16. DG

      Okay. You know what? Maybe you do get cut out. But that's okay because your friends are growing, and y- you're gonna keep going. Like, that's okay.

    17. JS

      Yeah. Yeah.

    18. DG

      If that's how you live your life and be a gatekeeper and say, "You know what? I, I, I'm gonna text that person, and then I, I wanna be the person that, like, don't do it without me. Make sure I'm CC'd or I'm part of..." Who can live like that, man?

    19. JS

      Mm-hmm.

    20. DG

      Like, I'm so happy to... And if they want me to come in the deal, I'll come in the deal. If they don't, no problem. But there'll be a deal later on that I might need that person for, and they're gonna remember that I connected them back then.

    21. JS

      Yeah, yeah, yeah. That's a huge lesson as well.

    22. DG

      The coupon system is the best system.

    23. JS

      [laughs] Would you explain that?

    24. DG

      Listen, when you do... When somebody does something special for me, I'm like, "You have a coupon, and anytime you ask something of me, I'm gonna, of course, be there." It's an untold situation that I really live my life by.

    25. JS

      Yeah.

    26. DG

      I have a lot of coupons out there, and a lot of people have done so much for me that I owe people so much that they could ask me to do anything, and I'm doing it. And I think that's the way you live your life.

    27. JS

      Yeah. Yeah, for sure. I love that. And it's, and it's like, it's almost like a constant state of gratitude and a constant state of giving.

    28. DG

      That's at the end of the key is the gratitude, right? When you, when you give someone, let's say, a coupon, that's just a way of gratitude, let's say.

    29. JS

      Mm-hmm.

    30. DG

      Gratitude really changes everything, the way you look at things, the way you feel, the way you, you, you come across.

  18. 35:5437:55

    The Power of Being a Connector

    1. JS

      Yeah. But no, it's, it's, my point is that you can either look at it as like, "Oh, look what I've done. Look what's happe-" And it's like, "No, but look, look what people have done for me," right? Like, "Look what, look what people have done for us."

    2. DG

      I know. People love to say, like, I'm a great connector, but people have done so much for me my whole life, and they continue to do so much for me. Like, look at Kim did the foreword. She didn't have to do that.

    3. JS

      I know.

    4. DG

      Johnny did the cover again. The fact that people still do great things for me, it's, it's, it's great.

    5. JS

      Yeah.

    6. DG

      And it, I, I'm so grateful and appreciative.

    7. JS

      I feel like you're at a place in your life where you're passing it on, hence the book. Like you're, you're passing on these lessons, you're telling these stories, you're, you're sharing the advice. I remember the, one of the first times I came across you was when you were doing this course at the university in Florida.

    8. DG

      Right. FIU.

    9. JS

      FIU. And, and I'd see these clips come up and I was like, "Who's this guy like literally taking everyone to a group of students? You're giving these students the best experience." Talk to me a bit about that because I think that feels like what it's led into the book, right? Like-

    10. DG

      By the way, the book is based on that.

    11. JS

      Right.

    12. DG

      So five years ago, FIU came to me and they said, "Hey, listen, we're the biggest hospitality school that nobody knows about." And I'm like, "Would you let me teach a course?" And they go, "What do you mean? Come and just tell your story?" I go, "No, no, I wanna teach a course. I want them to get credits for it." They go, "Okay, it's gonna be, you're gonna have to present us an, you know, a syllabus." So I go, "Okay, let's go." And they're like, but I'm like, "We gotta compress it." So five classes once a week for five weeks, three hours a class. And can I tell you what's so easy that you go through your day and you do with- without even thinking about it, to break it down-

    13. JS

      [laughs]

    14. DG

      ... was such a process. Like how do you break down relationships? How do you break down all the points that they don't teach you in school that you do so easily in your life? It was such a great process for me to go through that just to break it down. And I was so grateful to be able to teach it and below the, and like of course some of the biggest people in the world would come and surprise them each, each week. But to see the look on their faces, it was the hardest thing I've ever done, but by far the most rewarding.

    15. JS

      What was your favorite thing to teach

  19. 37:5539:47

    Scarcity vs. Abundance Mindset

    1. JS

      there? What resonated the most with the students?

    2. DG

      Well, the fact that they know who I am and where I'm at, and I started off bartending at a restaurant in the mall up the street from the school. So if I could go from a bartender at a restaurant in the mall one block from the school, a couple blocks from the school, then think what you could do.

    3. JS

      Hmm.

    4. DG

      And that for me was always the perfect setting for what I did.

    5. JS

      Hmm.

    6. DG

      And the fact that they were so special to, that I cared about them so much, knowing how busy I was, that I took the time to spend on making this class great for them. Hopefully they knew how special they were in life.

    7. JS

      I mean, I don't think anyone, you literally, I think you took Hailey, Kendall, Rick Ross, Bad Bunny, and-

    8. DG

      David Beckham-

    9. JS

      David Beckham

    10. DG

      ... Black Coffee, Ben Gorham, uh, Alex Earl, John Summit. But like-

    11. JS

      Yeah

    12. DG

      ... Port- I mean, the greatest people ever. Drake on the day he's releasing his album.

    13. JS

      [laughs]

    14. DG

      I was like, "Wow, Jay Shetty." But anyway, forget about those people.

    15. JS

      Yeah.

    16. DG

      It was, it was just great. And they would, I'd be like, "Okay guys, we're gonna end class a little early." And then Bad Bunny would walk in and they would like-

    17. JS

      Yeah

    18. DG

      ... "What the fuck?"

    19. JS

      Yeah.

    20. DG

      But they always had a lesson to teach. It wasn't just, "Hey, there's some celebrities showing up." Talk about your brand, talk about building relationships, talk about, everyone thinks everyone was an overnight success too. That's the most important thing. Everyone thinks these people just did it in one day. I'm like, "No, no, no. Tell them how long you, you were in the trenches for."

    21. JS

      Mm.

    22. DG

      'Cause that's where I think people, you know, they go, "I'm gonna graduate school. I'm gonna open my own nightclub. I'm gonna open my own restaurant." I'm like, "No, no, no. I was a bartender, I was a server, I was a manager." I go, "And that part of the journey was where the magic was."

    23. JS

      Yeah, yeah.

    24. DG

      That's what I, I loved.

    25. JS

      Yeah. Yeah. It's that- that's what also makes the, the climb special is, is all those lessons you gained-

    26. DG

      Right

    27. JS

      ... on the front lines that then helped you build the real thing. One

  20. 39:4741:56

    Check Your Ego at the Door

    1. JS

      of my, one of my favorite lessons in the book, you talk about this, you say, "Check your ego before your ego will check you."

    2. DG

      Right.

    3. JS

      And I wanted to know how your relationship with ego has changed. Because at the start you were saying, "Hey, there was a bit of ego and like I wanted to do the big thing." Talk to me about when you realized you had to check your ego.

    4. DG

      Well, the first time I ever had to check my ego was my friend Wayne Boitz at his Reserve Paddle. I had opened Liv and it was on fire, the craziest thing ever. And he said to me, he goes, "Listen man, you're not saving lives. You're not a doctor. You're not doing heart surgery. So why don't you just take..." And it resonated with me so hard. When somebody that you care about knows you, knows you for who you are and says, "You're, you're kinda like, your ego's getting a little bit big. Why don't you bring it down a little bit?" That's when I knew that it wasn't endearing to people for me to be like this super cool club guy. And that's why I've always just stayed who I am 'cause I've had great friends that like when there's times when you start to drink your own Kool-Aid as you know, as you get bigger and bigger and bigger, and that's when you, you're also afraid to ask for help and you think you know it all and that you're untouchable. To tell you, to be honest, I've had more problems with success than I've had with failure. Failure, okay, we move on. You, you forget about it the next day. But as success gets your ego so big, that's where the issues happen.

    5. JS

      Mm. Talk to me about that 'cause I agree.

    6. DG

      That's where you think you're untouchable and you think, you know, I think you have to stay in control, and I think by keeping your ego down during those times is when you could grow the most.

    7. JS

      How do you do that? How have you, because you are winning, you are on top, you're working with the best. How have you in those moments-

    8. DG

      Well, I have an amazing wife, Isabelle. Let's start there, right?

    9. JS

      She's awesome. Yeah.

    10. DG

      So she's just like too-

    11. JS

      She's amazing

    12. DG

      ... she's like, "Ah." Of course she wants me to win. She wants us to win, and she's fighting just as hard as I am. But also, you know, she keeps me in line too, but also at this point in my life, I know it's just way more powerful to be not so cocky, not so this, not so, just be so grateful.

    13. JS

      Yeah.

    14. DG

      And that's again where gratitude comes into place too, right?

    15. JS

      Mm. Yeah. Yeah, yeah, for sure. For sure.

    16. DG

      'Cause if you're grateful and you're serving others, then your head's not gonna get that big.

  21. 41:5643:03

    Staying Grounded While Winning

    1. JS

      Yeah. No, but I think you, you raised a p- good point. A g- uh, a g- in our case is a good wife is like a, is, is a game changer. And like my wife has s- my wife has checked my ego-

    2. DG

      Wow

    3. JS

      ... plenty of times.

    4. DG

      And she does it. She d- when my wife does it-

    5. JS

      Yeah

    6. DG

      ... she goes right for the jugular too. My wife does not play games.

    7. JS

      Same. My, my wife-

    8. DG

      It's like, "Ah," I'm like"I thought you said you loved me."

    9. JS

      Yeah, yeah. My wife is so direct, and she, like, cuts it right there, and she does not c- And it's the best thing ever because I love her and I know she loves me-

    10. DG

      Right

    11. JS

      ... so I can trust it's coming from a good place.

    12. DG

      You know what's so special is to have someone that you never have to question whether they have your back or not.

    13. JS

      Yeah.

    14. DG

      And having a w- a, a wife like my wife Isabella, what she's given me, I know that I never have to worry about if she doesn't have my best interest in mind, always. I never have to worry about it. And for me, just the confident level that that's given me has given me the strength to d- to get through anything. It's one thing that I think people kind of miss. Just trying to be out there and don't care about really love and relationships, and it's so important.

  22. 43:0345:28

    The Strength of a True Partnership

    1. JS

      How have you allowed yourself as a man to allow for that? 'Cause I feel like a lot of men can kind of get carried away and just feel like, "Yeah, I'm the shit," and, you know, you just move on, and then, you know.

    2. DG

      By going through that kind of stuff when I was younger has put me in a better place to be married, that's for sure. And I love that my wife is an entrepreneur and that she's out, and I can see her fighting. And I love that my daughters see their mother get up every day, go to her store, build her brands, invest, do all this. She could have easily gone for lunches and done nothing. Instead, the, Isabella Grutman Jewelry, she's killing it, and I, she doesn't stop. And I think it's such a motivation for my daughters to see that, not just me, but the family do it.

    3. JS

      Yeah. Yeah, for sure. I think it's, uh, it's setting a wonderful example for them and-

    4. DG

      And me

    5. JS

      ... yeah, yeah.

    6. DG

      She inspires me.

    7. JS

      Yeah.

    8. DG

      This girl is, like, dealing with it all. I'm like, "Wow, okay."

    9. JS

      [laughs]

    10. DG

      "Let's go."

    11. JS

      Yeah. And what, what does it look like when you kind of knew who you were for a long time, right?

    12. DG

      Yeah.

    13. JS

      It sounds like you know who you are.

    14. DG

      And that's why I'm, I'm okay being a plus one, because I know I'm not really ever a plus one.

    15. JS

      [laughs]

    16. DG

      Like, I want her to shine, but I know, like, come on.

    17. JS

      Yeah, yeah.

    18. DG

      Like, I'm so happy that she's doing this, and I'm like, I'm like her guest now at places. That's kind of the coolest thing ever.

    19. JS

      What's, what's something in hospitality that you've seen that blew your mind? Something that you went, "Wow, that was impressive."

    20. DG

      Thomas Keller, of course, at Surf Club, w- even at just the way his butter comes out for the bread. I'm always so blown away by even these c- the classic guys that really set the tone for what I do today-

    21. JS

      Yeah

    22. DG

      ... and their mentality on how they do things. Becoming friendly with Thomas Keller has been one of the greatest gifts ever, because he really gets the guest experience from the second you walk in to the second you leave. And what he does is the oysters and pearls he gives you right away, because... And it's something that my friend Jeff at Major Food Group does with Carbone. They bring the garlic bread and all the little fun pickings. Once you get... As soon as they sit down, you get them there, you've won them over, and that won- winning them over moment, the rest doesn't even really matter. As long as you win them over right away-

    23. JS

      Yeah

    24. DG

      ... it's, it's watching great guys like that really win.

    25. JS

      Yeah. It's, it's hard as well. Like, you feel like it's not easy.

    26. DG

      I mean, I'm constantly trying to evolve the menus and see what the, you know, trying to set new trends, and sometimes it works, and sometimes it just doesn't. [laughs]

    27. JS

      What have, what have you noticed about a good idea?

  23. 45:2846:42

    What Makes a Truly Great Idea?

    1. JS

      Like, how do you... When do you... Do you feel like the only way to know is obviously to test it, or do you kind of feel it in your bones and you go, "Nah"?

    2. DG

      I feel my bones. And listen, there's things where I think, "Okay, this is the greatest idea ever," but then the data just shows otherwise.

    3. JS

      [laughs]

    4. DG

      Like, I had a Grutman pastrami egg roll at Komodo, and I'm like, "This is the greatest egg roll of all time. It's a Grutman pastrami egg roll." My team comes to me and they go, "We, we need to go over something with you." And I go, "What's that?" They go, "The Grutman pastrami egg roll is the second least selling item on our menu." I go, "Second least?" I go, "There's a conspiracy. Are you sure?"

    5. JS

      [laughs]

    6. DG

      They go, "Yeah, it's heavy. The servers don't like to sell it." I go, "But it's my namesake. How could they not want to sell it?" The, the, the guests f- I go, "Well, what's the number one selling item?" They go, "The lobster dynamite." I go, "You mean the Grutman lobster dynamite?"

    7. JS

      [laughs]

    8. DG

      "So let's just change it right there." Uh, but, you know, I think it's the greatest idea. It doesn't work. And now learning with chefs that I know that I don't know it all as food. I let the chefs put items on the menu, and we let it, we let the data speak.

    9. JS

      Yeah.

    10. DG

      If it sells, it sells.

    11. JS

      Yeah.

    12. DG

      If it doesn't... But that's taken great chefs to come and push me into that kind of role.

    13. JS

      Yeah.

    14. DG

      And to let other p- And it's been a great way for chefs to feel that they have ownership in your place.

    15. JS

      Yeah,

  24. 46:4248:39

    What Makes Someone Worth Betting On?

    1. JS

      for sure. How do you, how do you decide who to bet on as people now that you're working with people and brands, and you bring in chefs, you bring in... You work with so many people across the board. What do you look for?

    2. DG

      I look for artists. I know I'm not the most creative guy in the room, but I love having creative people around me. It's what feeds my energy. Like, to be able to help enable an artist to do something special, and I'm part of that, it's a great reward for me.

    3. JS

      And, and what do you look for in them in their creativity that-

    4. DG

      Come on, Jay. We know when somebody's special-

    5. JS

      [laughs]

    6. DG

      ... and somebody's not. Let's-

    7. JS

      I wanna know your formula, 'cause I'm like, yeah, you-

    8. DG

      It's if they move me, if they make me emotional, if, if I feel connected to what their thing is. Uh, and let me tell you, I, I'm one of those guys, the last conversation I had with somebody, it's kind of like I'm, like, blown away by people. So if you can move me and I see something special in you, and I'm your friend, I'm gonna push you so hard.

    9. JS

      Sure.

    10. DG

      But if you're bad to me, you know. [laughs]

    11. JS

      Wow, what happens then? [laughs]

    12. DG

      No, no. I'm like the best friend, but the worst enemy.

    13. JS

      Yeah?

    14. DG

      Oh, yeah. Oh, yeah.

    15. JS

      Wow.

    16. DG

      Yeah, yeah, yeah.

    17. JS

      Didn't know you had that side to you.

    18. DG

      Oh, yeah, there's that side.

    19. JS

      Okay. [laughs]

    20. DG

      [laughs]

    21. JS

      What does that look like?

    22. DG

      No, I'm joking.

    23. JS

      [laughs]

    24. DG

      No, it's fine.

    25. JS

      [laughs]

    26. DG

      We want every, we want everybody... I'm, you know, it's like a monk.

    27. JS

      Yeah. Yeah. Well, yeah, I mean, yeah, in that side, yeah, that... I mean, yeah, the monks are equal to all, for sure.

    28. DG

      Right.

    29. JS

      But yeah, you, you, you act how you wanna act according to your values, no matter how anyone acts-

    30. DG

      Correct. Exactly

  25. 48:3950:32

    Learning to Slow Down and Reflect

    1. JS

      you the most le- recently, creatively, artistically? Someone that has had that impact on you where you've bet on them?

    2. DG

      So there's a guy named Ben Gorham, and he's the founder of BYREDO, uh-

    3. JS

      Mm-hmm. Yeah

    4. DG

      ... which is, you know-

    5. JS

      Oh, yeah

    6. DG

      ... a fragrance company.

    7. JS

      Yeah, yeah, yeah.

    8. DG

      He was homeless when he, he started the, the brand, and he sold for a big number a couple years ago. He moved from Sweden to Miami, and he's just so thoughtful on what he's doing for people. He's helped many people with fragrance and stuff like that now just as their friend, and he's really taught me to take that moment to really figure out what's the story, what's the meaning behind things, instead of just going, going, going, going. Be really thoughtful with what you're doing.

    9. JS

      Hmm.

    10. DG

      And I think that's been really impressive. Also, um, yeah, just my, my girls have kind of impressed me a lot too on how they see the world and how they, they're evolving. It makes me, like, inspired again to see the world differently.

    11. JS

      What do they see that you don't see?

    12. DG

      They see so much good and so much... They're like, like, they get so excited about just the dolphin or the bird or their rabbit or, you know. And the fact that they're just, they're so content just being with that, and I just wanna learn that kind of practice again, just being so happy and content. And my wife, by far, has just been blowing me away. She's very special.

    13. JS

      Hmm. What's the biggest impact she's had on you?

    14. DG

      For her to realize why I get so ups- 'cause, you know, when she launches her brand, the website goes down, this happens at work, this, um, you know. And to see how she's handling those same frustrations. But she found her way. Like, she never thought she was gonna be a jewelry designer. She started off making her clothes, and then she met some great jewelry designers, and she started her own brand, and she found what her passion was, and it wasn't what she, what she thought she was gonna do. And I love when it just hits you, and then you take it. A lot of people, it hits them, but they don't take

  26. 50:3254:53

    Finding Joy in the Present Moment

    1. DG

      advantage of it.

    2. JS

      Mm-hmm.

    3. DG

      She took it, she took it and ran with it.

    4. JS

      Yeah. Yeah, yeah. And I love what you're saying about the presence with your, seeing the presence of your girls, like that being something you wanna get. Is that something you feel like you're getting to at this point in your life?

    5. DG

      Yeah. Listen, I feel like my childhood was a little bit different than everyone else's. I didn't think I was able to be a kid because I was around the done that. And just to see, like, the feeling they get with the simplest thing. It doesn't have to be the most expensive or elaborate thing, just they like out... And just by being, spending time with me, to them is just so precious.

    6. JS

      Hmm.

    7. DG

      I'm like, they make me feel like the biggest man in the world.

    8. JS

      Hmm. That's beautiful, man.

    9. DG

      Thank you.

    10. JS

      Thank you for sharing that. Yeah.

    11. DG

      Of course.

    12. JS

      Yeah. At this point in your career when you could be doing anything, you're going into production and TV.

    13. DG

      Yeah.

    14. JS

      And I know you're, because I know you're also working with Fulwell too-

    15. DG

      Yeah

    16. JS

      ... who I'm working with. I'm good friends with Ben Winston, so.

    17. DG

      Ben Winston-

    18. JS

      Yeah, yeah

    19. DG

      ... is the great... By the way, how much do we love Ben Winston?

    20. JS

      Let's, let's, let's do that. Ben, we love you.

    21. DG

      Ben-

    22. JS

      He's gonna, he's gonna love this love

    23. DG

      ... I love, I know you love the shout-out, so I'm giving you-

    24. JS

      [laughs]

    25. DG

      ... the big shout-out, Ben Winston. I had to convince this guy for years. I'm like, "Alex Earl." I'm telling you, Ben-

    26. JS

      How did you have to convince him about Alex Earl? Can we just-

    27. DG

      He had no idea who he was. He, he at first, and then he started doing-

    28. JS

      Ben

    29. DG

      ... Ben-

    30. JS

      We need to talk

  27. 54:531:02:07

    David in Final Five

    1. DG

      [laughs]

    2. JS

      Good answer. Good answer. Second question, what is the worst advice you ever heard or received?

    3. DG

      You should definitely take that space.

    4. JS

      Oh. [laughs]

    5. DG

      [laughs]

    6. JS

      Someone promoting the wrong space.

    7. DG

      Yeah, yeah.

    8. JS

      Yeah, yeah. That's funny. That's funny. Ca- do you have an example of that, of-

    9. DG

      Yeah. I, I-

    10. JS

      Yeah, go on. Talk to me

    11. DG

      ... I, I opened a diner in a old Firestone gas station. I failed so badly after three months I had to close it after three months.

    12. JS

      God. How ma- how many things have you had to close down?

    13. DG

      Two restaurants and a nightclub, but the nightclub, the city closed me down, meaning there was high-end r- buildings that came around the nightclub.

    14. JS

      Right.

    15. DG

      But, uh, it's definitely not gonna be my last restaurant I close. I'm gonna have to close others at some point in my life, and I'm gonna have to open new ones as well.

    16. JS

      When, when something closes down or fails, how do you go back out there and raise more money and raise energy? Like, how does that work?

    17. DG

      Because thank God you have the emotional bank account. You've done some successful things and, you know, not everything's gonna work, Jay, and I think people kinda, you know what I mean-

    18. JS

      So people don't write you off. You don't feel like the world writes you off when you fail?

    19. DG

      No, but you try to make good on it, too, like, later on in life as well. But, uh, no, people wanna still come to my experiences.

    20. JS

      Yeah. No, 'cause I feel people are scared about that, not just you, but I feel like a lot of people are scared of having a f- a big failure.

    21. DG

      By the way-

    22. JS

      Yeah

    23. DG

      ... it's the scariest thing in the world.

    24. JS

      Yeah.

    25. DG

      But guess what you realize? It's scarier to you than the rest of the people out there. The single e-

    26. JS

      No one's thinking about it.

    27. DG

      I s- okay. They think about it for a day or two. That's fair, and then you open another hit, and guess what? They don't even remember what that's.

    28. JS

      Yeah. I always say that to people. If you think of your favorite actor or actress in movies-

    29. DG

      Ugh

    30. JS

      ... they've all made bad movies, and you've forgotten about them 'cause they made the iconic ones that you remember.

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