How I Helped a Business Owner Build His Dream Dating Life

You ever meet a guy who seems to have it all figured out? Business locked in, freedom, lifestyle, but deep down he knows something's missing? That was Jacob. He was still going on a lot of dates, still taking action, but something wasn't clicking. He wasn't showing up how he actually wanted to. He was wearing a mask, and deep down he knew he wasn't attracting the kind of woman he actually truly desired, the kind of connection that changes you. So we got to work. What happened next? Let's just say he dropped the mask. He owned the standards, he started connecting from a place that most men never access. If you're done performing and you're ready to live, love, and lead from your deepest truth, apply for exclusive coaching with Papa Club below. The journey starts way before the girl shows up. Now let's vibe with Jacob. All right, we are here. The suspense, crazy. Appreciate you coming on to do this with me, Jacob, or Jacob. Yeah, really, really big thanks. And a little bit about me for those who are just checking out this video. Stephen and I help high performers create their dream relationships and lifestyles through personalized coaching and global retreats. And this is Jacob, and Jacob and I met at House Manifest about a year ago in Thailand. And House Manifest is a residential accelerator, an experience that I created a couple years ago for nomadic entrepreneurs and creators. And when we first met, obviously we were in a setting where, um, it was very conducive to us talking about life and different aspects of life. And specifically, we ended up talking a lot about dating and relationships. And, um, I ended up having the big pleasure to get involved in Jacob's life and help him kind of navigate those couple of things. So Jacob, can you start by introducing yourself and telling us a little bit about your background?

My background is corporate for many years, a bunch of years. Left that to start my own real estate company, Florida. A couple years into that, so happy, kind of, kind of moving and grooving with that. I decided there's a bit world to see out there. So I sold all my furniture, packed a backpack, and took the business remote. And something just told me, you know, I hadn't been to Asia in almost a decade. So I went over there and by coincidence, I met Stephen hosting one of his seasons in Koh Samui, Thailand. We connected. I think it was the relaxation zone of the property that hooked me. That was the coincidence how we met. So amazing hook. I had the experience, it was fantastic. Met a bunch of awesome people and, uh, you know, continue that journey and, and those friendships. But then ultimately, as a result of that experience, decided to pursue a much higher entrepreneurial passion of mine. Still keeping the real estate stuff going, you know, to pay the bills, but, and that is Transplant Coach, helping other people get, uh, get kidneys in the United States based on my own experience. Of the kidney failure. So that's a bit about me and where we're at today.

Amazing. Nice one. So Jacob, when I first met you, I remember talking about business quite a bit and entrepreneurship, and obviously you built a very successful remote real estate project slash business and it was going very well. And then your dating life seemingly no problem on the surface level, at least, right? And then the more we started talking about it, the more I think we kind of came to an understanding that maybe there's some guidance that could be needed. Can you kind of like take me back to where you were before? Like where were you at in terms of your love life and what kind of challenges you were facing?

I think a lot of people who get into the entrepreneurial game, you know, or even not, they care a lot about their physical fitness and their mental fitness and stuff. And so to me, like I always, enjoyed dating on the side, but getting out of corporate and going, you know, going after my dreams, I focused very heavily on that. Like, I kind of shut everything else out and was like, I just need to focus on being quote unquote successful, whatever that even means, and that's most important. And if I can do that, then the other stuff will come as a byproduct. And it all felt okay because I was building my business, I was traveling, and I was dating. I was meeting all these different people and these, these women, uh, amazing people. But I, I found a couple years in, and especially when I, when I met Stephen, we started chatting, that it was very surface level to me. Like, it was hard to go to the level of depth that I think I needed because I had kind of blocked that part out for a while so that I could tunnel vision focus on making money and, and building a business and XYZ PDQ. And it really wasn't until we met in Koh Samui, Thailand, and we started chatting and becoming friends. And ultimately working together that I kind of realized it takes a lot more work than that, you know? Like, sure, you can go through, like, and that's cool, right? To go through life and be surface level with dating, going from place to place. But if you want something more in-depth and meaningful, you have to put as much effort into the dating side as you do into the business side.

Got it, got it. So what I'm hearing is that even though you got to a point where in terms of like the availability, like your options when it comes to, in, in terms of dating, you didn't really have any issues, but then you wanted to get to a certain place that you wanted to kind of like have this depth. And does that mean that like you, you were looking to essentially create a relationship? Is that what you're looking for? Like when you talk about depth, like can you, would you be able to kind of elaborate on that? What that actually meant for you at that time?

I think it's twofold. One is understanding my own core non-negotiables and criteria, like your love language. And this is stuff maybe stereotypically as a guy, like we don't think about much because that seems kind of taboo a little bit, but like what is truly attractive to you beyond the surface level of like status and physical appearance, that nature. So that's, that's kind of the first part, I think. And the second is communicating that in like a stable way when it happens, like when you meet someone who is at that, like, how do you navigate that? You know, because to me it was always like, oh, just, you know, be kind of aloof, like whatever happens happens, and you can just play, you know, just kind of, but what kind of ends up happening because of all the opportunity and options we have nowadays between dating apps or just people you meet out in public, you know, it's like when there's infinite options, you kind of have the tendency to quit and to, to run or to leave at the first sign of a flaw or trouble. And, you know, I never really took the time to look into that and understand why that happens and how to address it. And I attribute a lot of that to you, um, for helping kind of navigate that.

Amazing. Thanks for that. Thanks for that powerful introduction. Taking a step back, what made you say yes to the possibility of working with me?

Well, we were friends beforehand, you know, maybe I'm a little spoiled or I have a little bit of a biased perspective, but you know, you're one of my closest friends and it's just awesome. You know, you have an amazing vibe. Uh, you're great to hang out with. And, uh, I've had the, the fortune of kind of seeing the House Manifest side and then seeing you really ramp up this, this business, which you, which you show up to with genuine authenticity, which I don't have a lot of experience in this space, but I'd imagine is not quite as common. And so for me, it was a no-brainer. What do we have to lose? You know, it's like, I see what could happen. You know, I'm not going to be worse off. If anything, I will be materially better off. So it was kind of a no-brainer for me.

Yeah. Yeah. No, I really appreciate that perspective. And for me, um, it's been a huge honor to be involved in your life in such a major way, and then you trusting me to become your advisor in this very delicate and sensitive and profound process of kind of navigating all of this. So yeah, it's been like super fun and very, very just lovely in it. And you started talking about how, okay, like love language to non-negotiables, and how to actually communicate what you really, really desire deep down and actually bringing out your authenticity into the forefront. And like, on top of that, like, I would say, like, kind of tangibly speaking, what changes have you seen since we started working together? Like, what were some of the most, like, noticeable changes in the way of— in your way of being?

Most importantly, I think I've been thinking— I was thinking about this recently— is when I go out or when I meet someone new, You know, I go on a date, it's very easy for me to quickly assess if this person makes sense for me to dedicate more time to. And not just at like a physical attractive level, of like a love language and a communication level, which is so important to me. It's one of my core non-negotiables. It's so important. And, you know, and I'm not judging any way, shape, or form. I'm not optimizing for like the quick one-night stand at this point. I'm more trying to look for. The, the vibe, uh, long term. And so for me, to be able to quickly assess that means I can go out, I can meet someone, have an amazing time, but know leaving, like, okay, it doesn't make sense for us to hang out again. Just, it's not, not worth her time, it's not worth my time. And, and if there's, if there's more that happens as a byproduct, great. But like, I'm very clear it's not great. Whereas it's easy to have the tendency to be like, well, she has XYZ PDQ, you know, and I like that, you know, she has this kind of job, she's from this kind of family. And like, you get into this weird weighing pros and cons where it's like, if it's the non-negotiable or it doesn't. And I wasn't so good at that prior.

Got it. That's, that's actually really, really interesting because correct me if I'm wrong here, but like either way, right? Basically what you're describing is, um, being able to sense someone's vibe., right? And then actually trusting your intuition good enough so that, you know what, like these are the different non-negotiables that I really, really value. And I hold myself to a certain bar that if clearly they, they don't, if we don't really have this vibe going on, like I'm not really interested in kind of moving forward. And then obviously there's like a lot of nuance to that. And then on top of that, also what you spoke about is like before on paper, maybe they kind of tick off a lot of the qualities and attributes and the right boxes, but then maybe deep down you didn't like feel the vibe. So then you were kind of still like, okay, on paper they look good, they— everything looks pretty decent, so let's actually explore the possibility. So what actually took you to get to that state of being? Because I'm hearing a lot of like abundance mentality, obviously, just Being able to have that courage to say like, okay, you know what, attractive person, vibe is great, but then, you know, I'm looking for like a, a more profound vibe and then like probably not the right vibe, you know, move forward. So we're talking about a crazy transformation here. So like what, what actually happened?

I think there was, there was a lot of past relationship breakdown. I think that was a big part of it because it's so easy to be like, well, that didn't work. And I know it didn't work. I'm not really sure why. I don't care. Let me just move on. Let me just look forward and like just move on to the next date, the next person. I think it's much harder to sit down and review your old relationship patterns and actually look at like the text, the content, how you reacted, how you felt, and kind of write that out, uh, which I didn't do frankly, uh, until I was hanging out with you in London. So that was extremely helpful. And understanding your love language. You know, and it's such like a cheeky term, you know, that's used so lightly, but it, it's actually quite profound because I think it's much harder to change or, or to ha— to have people change as compared to trying to optimize for meeting someone who understands your love language and can speak it. It's just like a way, and I, I didn't experience that funny enough until we were hanging out and I was just kind of, you know, I was dating around a bit. And wow, night and day. What a, what a difference.

Wow.

Yeah. A lot of, a lot of looking back at your relationship stuff and talking about it and doing an actual breakdown and being pretty clear on what you like.

Got it. Amazing. Nice one. Any, any blind spots that, uh, you were able to uncover during our time together?

So I think one is part of the, part of what you mentioned about being authentic in your vibe and and how you present yourself is also not buying into the, the societal norm of like communicating your thoughts and emotions and being vulnerable is weak because it's not. So I think one of those blind spots I had was like not, was being afraid to fully express my feelings for someone because like, hey, I, this is how I feel. This is the deal. Do what you will with it, right? Like I'm cool either way. But this is how I feel and here's why. And in both contexts, one for people that you like, women that you like, and on the flip side, for women that you liked, but it didn't work out the way that you wanted it to. And you didn't want to leave anything out there. You know, you wanted to close it and be honest. One for yourself and one because, you know, sometimes your partner or ex-partner has no idea really. And it's helpful to them for their next relationship to know.

Wow, powerful. Nice one. And, uh, with this vibe, this new vibe that you have right now, where do you see yourself a year from now, 2 years from now, 3 years from now?

What's this—

what's this new possibility?

You see myself living in an environment that is wholly authentic to me and what I like, in building my lifestyle around my vibe and building that solid foundation and being open and abundant to dating and to like whatever comes in, but knowing that I've built a life that makes me happy irrespective of who comes into it and who leaves it. So if I meet someone and decide to take it further with them into a relationship, it's coming from a place of abundance instead of a place of like, well, you know, based on how old I am, you know, I should be married by now. I should have kids. I should follow all these societal norms. And honestly, this is just my opinion, but I think that leads to more unhappiness.

Solid. Sure. Got it. So what I'm hearing is that instead of sort of like, uh, in order to kind of adjusting your vibe and adapting your vibe in order to sort of kind of fit someone's frame or vibe, but then really building yourself up first, like establishing your own vibe first, building that vibe, and then building that frame, building that world, and actually enrolling someone else excited enough to be a part of your world to be there and then like build that together. That's what I'm, that's what I'm hearing. Nice one. Nice one. Would you be able to share a specific moment or any, any particular like session or exercise that was particularly valuable or transformative for you now that you, you reflect on our, our time together?

Wow. Yeah, there was quite a few actually. It was a busy period of time when we were hanging out in London together. So there's a couple. One, which I've been talking about a lot today, is, is on the reflection side of like writing down with someone that I was seeing what really bothered me. Like I had this feeling that something wasn't right, then what was it really? And like sitting down and unpacking that, like step by step, prompt by prompt, like what bothered me about the relationship. And then that ultimately led to the discovery of what my love language is, which I think is hugely powerful. That's one. And then two, maybe on just more like the technical side, you know, as someone who legacy would use dating apps, you know, I would meet people in real life sometimes if I was introduced to them, like friends of friends, but I didn't typically meet women just out in public. Was just hanging out with you, walking around, doing our thing, you know, enjoying the beautiful city. And, uh, we were sitting at a Shake Shack once and, uh, And you were like, yo, go say hi to that girl. It's like, what do you mean? She's like eating her food. Like, I'm not gonna go say, like, what do you— you're like, no, just, just do it. Just do it. Just go chat with her. Just go ask her, go sit down. I was like, all right, sure. So I do it and I'm like blown away because I'm just chatting with this girl, you know, just having a good time. There's no expectations of it. We're just having a great time. And there was just this like societal perceived barrier that I thought that you think exists. With people that they're unapproachable unless it's in a specific circumstance, like you meet them on a dating app, it's at a nightclub. It's like society has to give you permission basically. And that's actually not true. That was kind of shattered. Oh wow. And I thought that was quite profound.

Yeah. Wow. Yeah. I remember that was actually one of the first moments that I, I asked you to go say hi to someone and then I was actually really pleasantly surprised that, I mean, Like, it seemed like, I mean, you asked me, it's like, really? And then I was like, yeah, really. And then you're like, you did it? And then you're like, wow. And I think I could see in your eyes that like you had a bit of a breakthrough. And then I think from that moment on, I kind of saw you just like keep rolling with it. There was like a bit of a momentum. And I think there's like, um, you spoke about how there's this like perception that like, you know, society tells you like, this is not like the right thing to do, or like, this is like the a normal thing to do. And then once you've broken that, you're like, okay, you know, I'm here to create my own reality, here to choose my own adventure. I've really seen that. And then, yeah, I think in a way, this is kind of like what happens to what I've really witnessed in different sort of clients as well, because they always come to me with this vibe of like, okay, I don't feel attractive. If I talk to them, I might bothering them. You know, if I talk to them, then like, you know, they're just going to reject You know, and then, well, first of all, like, you don't know them, they don't know you. Instead of trying to take value, offer value, you know, like compliment them and then like tell them what you observed about their vibe, their outfit, nationality, whatever. Give value, have fun with it, you know, say hi. And then like through action, you actually dismantle those blocks that's standing in the way between like what you think like the vibe is like. Versus like what you want the vibe to be. And then once you actually take action and then you really get to the next level. And then I've seen that with you like time and time again. So yeah, that was very, very dope, you know, to say the least.

It was a great experience. And then after that, I would just be at like lunch, you know, somewhere at a cafe in the middle of the workday and just start chatting, you know, with people next to me, you know, and it's like, and it's helpful. Like the, one of the original reasons I, you know, we were chatting way back when. You know, and you started getting into coaching? I was like, well, from a professional standpoint, I want to be able to walk into a room and I want to be able to instantly make deep, meaningful connection with other colleagues as well. There's a personal flavor and a professional flavor because like networking events can be so awful and boring and like, you know, exchange obnoxious small talk. And I was like, I really want to get better at that, you know, because I find like there are a few people you meet become really good friends and make meaningful impact on your professional life too, and whatever your industry is. And, uh, that was a big component. And I was just at a conference, you know, not too long ago where I went in with that approach and it was like night and day. It, one, it was way more enjoyable. I had a lot more fun. And two, it was kind of entertaining because it's like a pattern interrupt. People expect you to be like, oh, hey, so what are you working on? Oh, hey, so what do you do for a living? Instead of commenting on an observation that you have about them, they're like, oh, oh yeah, you know, having a glass of red wine at 12 o'clock. Yeah, why not? You know, like a totally different opening at a networking event that creates a way better relationship. So huge value there too.

Yeah, it's like what I'm hearing is like, yeah, there's like a certain script that people kind of run with when we, when people go to those types of events. Like what do you do? Like these like standard set of questions that everyone's tired. Everyone's tired of repeating the same thing over and over again. And they're like, okay, if you're meeting like dozens of people through this type of experience, like, what are you actually going to remember about them? You know? And knowing that, like, how do you actually stand out? Well, like, you connect with them on an emotional level. And then you do that by like having that baby frame, right? Babies are curious. They like to play around, you know, they're playful and they don't give a fuck. And that's the, that's the vibe, you know? And, uh, yeah, speaking of which, you're, you're, you're telling me a little bit about, yeah, like what happened, like in this conference. How did our work, you think, actually impact other areas of your life outside the dating and relationships aspect?

I think work is a big piece of it for sure. Um, I would say mostly because you just, you command a lot more positive connection and almost authority in a way when you walk into a professional setting and you aren't very like high anxiety and very like too focused on XYZ or you're being transactional. So as an old school corporate guy who would wear business clothes every day, you know, I went to this tech conference and I showed up in like a casual Zara, like cloth shorts and my button-up shirt. You know, she's like super, like something you'd wear on the beach. And it was so liberating and very different than my norm. And I can't, like, just off the bat, you could tell people were like, whoa, like, what's up with this guy? Like, he doesn't, he doesn't care at all. Like, what is his deal? And so I would start chatting with people and it was much more about having fun and making meaningful connections with people. Like you say that you can. Remember something about them or that I give them value and they take away something from me. And I've spoken to like half a dozen people since that conference, like on the phone or consistently, and, and a couple of them were like, yeah, I just really like talking to you, you know?

Yeah.

And it's like, I didn't profoundly do something different than who I am as a person. I just chose to change the frame and approach the situation different. So that's huge. I would say that was very helpful. Definitely one of the big things I, I asked you for help You know, way back when. Super grateful for that.

Funny enough, actually, that was the first thing you asked me when we were in Bangkok. I remember your first question ever is like, Steven, how do you vibe? What is behind? Tell me more about this connection thing.

Hmm.

Interesting question.

Because who doesn't want that in whatever application of life? You know, like who, who doesn't want to be a top, uh, you know, have that presence.

Amazing. Yeah, I mean, what I'm hearing when you say that is just like a lot of freedom, freedom to express like your own authenticity, like very powerfully. And when you do that, it's just like you don't have to front, you know, like you're not trying to be someone that you're not, you know, you're just like, okay, like I can wear this mask if I want to. I've done it for a long time. I don't, I don't want it anymore. I'm here to really let my authenticity shine. And then yeah, you're like also kind of trusting the process of like, yeah, letting the vibe guide me or letting the guide guide me. What would you say to people who are kind of considering whether they should work with me or not. Like, would you recommend my coaching to, uh, these types of people, other people, and why?

Well, I would, obviously. Maybe I'm a little biased. No, I, I would. I think if you're like on the other end of, you're like considering coaching service, you should ask yourself really why, like really what is it that you're trying to achieve? And if you're not sure, like compare a few options because it's very clear. It was very clear to me, not just because we were friends. But that like I've seen how you interact with people. I've hung out with you in multiple places around the world. Like it was very clear to me that of this type of service, there's no shortage of people who do it, but they're not all built the same by far. They don't all come from the same place. They don't come from the same motives, incentives. And we clicked for a couple of reasons. And I think a lot of other people will too. One, we share a lot of professional things in common. You've been in the corporate game. You've been in the entrepreneurial game, you've been in the grad school game, like you've been in and out of the matrix, as you say, like there's a lot of things, like it's just, it's very easy for you to understand where I'm coming from with both my professional challenges and the personal side. I mean, you've dated, you know, many people, you've been in this game for many years. This is very clear. It was a very clear value proposition too.

Amazing. Nice one. So background. Similar background and also like the vibe.

It's always about the vibe.

Everything is about the vibe. Everything is energetics. If you don't feel the magic, what are you doing? Cool. Thank you so much, Mr. Jacob or Jewish Bad Boy, JBB. And yeah, any parting words here?

Yeah, it's not as hard as you think. I feel like I hear this at real estate and other conferences too, but it's true. It's like, Anyone can do it. It's not hard. It's not difficult to do, but it does take work. You know, it's not rocket science, but like you have to be open to change. You have to be open to feedback. Yeah. So super excited, very grateful, obviously. And, uh, hopefully, uh, hopefully this helps a few people get on their next step of their journey too.

Amazing. Thank you, sir. All right.