Jacob Rupp: From Rabbi to Coach

what I noticed was I think there's a massive, what they call inefficiency in the way that education works and the way that people make money. Most people spend lots of money not to make a lot of money and wind up hating the work that they do. And what I realized was that most people know how to do one thing better than a lot of other people, and people would actually pay them for that, that insight. And so if you have people that are passionate about the things that they're doing and making good money doing it, there's always going to be— I see kind of like this healthy marketplace of ideas where we can always get good again. Like, Why do I have to reinvent the wheel if I could hire a physical trainer that's built the kind of body I want and knows how to help me build mine? I'm paying him for speed and accuracy in terms of getting to where I actually want to go. So I've realized that in anything I actually care about, I want coaching or support around it. And I get coaching in my religion, I get coaching in my career, I get coaching in how I sell, my mindset, my marriage. There's nothing I don't really care about that I don't invest in coaching.

This is The Chris Project, where we discuss mental wellness, self-awareness, and mindset with entrepreneurs and experts. Set your perceived ideas and biases aside and let's go on our journey for yourself, for your family, for the world.

Welcome to another episode of The Chris Project. I am your host, Christian Brim. Joining me today, the esteemed— I don't want to say infamous, not yet, but the esteemed Jacob Rupp.

Jacob. I'm working hard for that infamy. And I happen to believe you are probably one of the most talented interviewers that I've heard. And I listen to quite a few podcasts. I am, no, I am like actually deeply impressed by the level of depth and insights you get from people.

Well, you may regret that after today's episode. I don't know. We'll go digging.

Yes. Probably. That's what I said at the beginning.

Yes. All right. So let me introduce you a little bit since Jacob, you are my coach and I've been working with you for 3 years. I know a a little bit about you, and I'll let you fill in the blanks because I want you to go back to the origin story. But Jacob is a coach of coaches. He is, uh, I don't know if the word is ex, but a former— how about a former Orthodox rabbi?

Ex implies I did something to get fired and lose that, so I prefer former as well.

Thank you. Yes, former Orthodox rabbi, married with 4 children? Yes, 4 children. 2 girls, 2 boys?

Uh, 3 girls and a boy.

Oh yes, okay.

And my dog, my dog, which was really the best.

Yes, you have a certain affection for your dog. I love her. So Jacob, let's go back and tell, because I still find this fascinating, how does a kid from Southern California— is that where you're from? Northern California.

Northern, that's okay, it's close.

California. How did you end up as a rabbi first? Let's start that.

So I decided I wanted to be a rabbi before I believed in God. I couldn't read a single word of Hebrew, and I had no idea what Judaism was except that I was Jewish. So, you know, they say that you can take the, what did it say? The ghetto, but you can't take the ghetto outta the kid, or whatever that thing might be. Yeah, so this was something that went back. I wanted to be the president, and for quite a while, then I heard this rabbi speak, and I was like, okay, I could be a rabbi. Now again, this had nothing to do with Judaism. It was the idea that like, I wanted to impact people and have them live in a positive way. And I happened to be Jewish, And so what Jewish— now again, with all love and respect to the rabbi that I grew up with, I never even thought that he was inspiring, he could connect. But this guy was animated, he was amazing. It was funny, I saw him about 25 years after that initial time I heard this rabbi speak. He was the head of my grandparents' congregation in LA, and I went up to him. And now again, I had become— went from completely secular, no God, the Torah, the Bible's not divine, I will eat, if it's shrimp, bacon, and everything, I'll eat all of it at the same time. It's like, you know, to becoming like at a certain point, white and black with a big black hat. And I went up to this guy after seeing him at a close friend's wedding about 25 years later. I was like, look, you made one, I heard you make one speech. You changed my life. I became a rabbi. I said, you know, you actually gotta figure it out. I don't know if I had to become as extremely religious as I ended up becoming. He's like, yeah, I don't know why you did that, but the rabbi thing was a good call.. So that's how I started. I met my wife when we met. I met her when I was obese at 18, and she was very into— she was dating lots of people. And I, at that point, had started my business career, although I didn't know I'd started my business career, of really trying to figure out what my unique selling proposition was. And if you're obese and have serious social anxiety around asking women to go out with you, at least you're Jewish. So I really honed in on that. And really built up the Jewish thing.

So the hat was the selling point.

Actually, that was the reverse. The truth is, if I'm getting very vulnerable, probably that as well. Okay. I was not wearing a hat by that point. I was just running the fraternity and I was running the services and I invited her to come to services and I invited her to come to the fraternity. She actually found like Orthodox Judaism, like because her background, she was like a blank slate when it came to Judaism. And so whatever, without— kind of outside of the scope of this podcast, there's sort of like what we would call Orthodox, which is basically what Jews practiced for 3,000 years that we've been around, and then a couple other strands built up that really have no philosophic connection to Orthodox Judaism at all, which is what I was raised with. So Julie was very much like an open slate. She's like, well, if we're gonna do this Jewish thing, why don't we do what everybody always did versus like try to recreate it? I was really uncomfortable with that, but ultimately when I realized that was the direction she was going, then I think I went in that same direction as well, to be completely open and honest and transparent.

So you didn't grow up in a Jewish home or were practicing?

Yeah, practicing not. My mother's very— my mother, my father is not Jewish. My mother was Jewish. But yeah, we grew up like driving on the Sabbath, which is one of the things that you're not really supposed to do from a biblical Jewish, biblical perspective. Non-kosher food in the house. I knew Judaism was important. I grew up on a healthy diet of like the Holocaust and unhealthy eating practices, and that was pretty much the extent of my religion. My mother would be offended if I said that. I'm not going to say it to her, but that's, that's— yeah, there was, there was more than that. We kept the holidays. How's that? My grandmother was short.

Very good. So, okay, how does a rabbi become a coach?

So I love the most about being a rabbi, and that was kind of the common theme throughout all of it, is I loved impacting people. I loved impacting people. I loved helping people live a more meaningful, connected life. I really got my stripes in the trenches of— I worked at UCLA for about a decade dealing with very, very intelligent kids that had no reason to buy into an antiquated religion. So I really had to be good enough and making it practical and appealing. And again, those fundamental skills of can you make this relevant in my life? And what I found was that a lot of the things that everyone looks for in life in terms of a sense of purpose, a sense of self, how do I know who I am, how do I have meaningful relationships in my life? Those were all common themes that I realized weren't exclusive to college students alone. And in a lot of ways, I realized that Jews and non-Jews really appreciate having a good relationship with themselves, with their Creator, within their business. And so it was very painful natural transition when I realized I was, you know, 4 kids in, sending them to private school in LA and completely broke, that eventually I figured out— and fired because I'm hardly employable as an individual— that I found that this was a calling that I could actually do pretty well with and, and make a good living doing.

And that was— you've been doing it how long?

I mean, at this point, like coaching?

When did you quit the clergy?

Again, that was a longer process, but I really started coaching about, oh, I would say probably over a decade ago.

All right. Very good. And now you coach coaches. Talk about that.

I— yes. Well, you know, one of the things is the people that make— I mean, it was both a strategic business decision in the sense that the people that made the most money in the Gold Rush by far were the people that sold the jeans and the axes. And so I think that there is a mass—

the Levi's, the Jews.

Yes, yes, yes. You nailed it. There it is. The people making all the money at the end of the season. You said it, not me. Gosh. Anyway, I was going to say, by the end of it, I was going to be listening like, hmm, is that true? Yes, it's true.

Hmm.

Yes, it is true. Anyway, so what I noticed was I think there's a massive, what they call inefficiency in the way that education works and the way that people make money. Most people spend lots of money not to make a lot of money and wind up hating the work that they do. And what I realized was that most people know how to do one thing better than a lot of other people, and people would actually pay them for that, that insight. And so if you have people that are passionate about the things that they're doing and making good money doing it, there's always going to be, I see kind of like this healthy marketplace of ideas where we can always get good again. Like, Why do I have to reinvent the wheel if I could hire a physical trainer that's built the kind of body I want and knows how to help me build mine? I'm paying him for speed and accuracy in terms of getting to where I actually want to go. So I've realized that in anything I actually care about, I want coaching or support around it. And I get coaching in my religion, I get coaching in my career, I get coaching in how I sell, my mindset, my marriage. There's nothing I don't really care about that I don't invest in coaching. And so I realize I want to be a part of that because again, like I came from a background, I ran a— like I was a nonprofit like professional, whatever, nonprofit. I worked in nonprofit. I was broke as a joke. I couldn't get work anywhere else would allow me to feed my family. Granted, again, sending 4 kids to private school in LA is still— you still, you have to make a lot of money to be, to be able to, to do that. But bottom line was I knew that if I had the skill sets and that was, that was the cool thing is after working with enough entrepreneurs, I learned the fundamentals of how do you build a business? You have to be clear on what you're offering. You have to be clear on how to sell it. You have to be able to make money in the process. So once I sort of learned that, I realized if I can teach other people how to do that, so that they can make good money and do what they love, that would be a contribution to the world I'd be very happy to make.

I love that. So you mentioned that you do coaching. One of the things that we've talked about, and I think is a true axiom, is that a coach needs a coach. So what do you say to that? Like, if someone works with a coach, does that coach need a coach?

Oh, I've never seen it work without that. Meaning, you know, one of the things I— in between my, uh, my decade-long career, uh, career debacles, I sold insurance for a very short period of time. And one of the things I noticed when you sell insurance, the first question your prospects ask is, do you have this product? And if you don't, they pro— again, or to make me sound even more impressive, when I was trying to buy, I have larger, my kids are getting bigger. And so I was looking to swap out my, or I entertain illustrious guests like yourself that are 7 feet tall and getting in and out of the Porsche 911 is a little bit of a strain. And so I was looking at bigger vehicles and I went to park my car at the Lexus dealer and the guy comes out and spent the entire time talking to me about my Porsche and didn't spend a single second with the Lexus. So at the end of the day, if you don't buy what you're selling, neither is anybody else. So a coach without a coach is ultimately, I think, kind of a farce in the sense that they're not part of the process that they're facilitating other people in. Again, I thank God been around really successful people in a wide variety of areas, and I've never seen the facilitator or the master not themselves be even more immersed in the work than the people that they're supporting. In jiu-jitsu, in weightlifting, like if that person's not spending more time on the mat or in the gym than all the people coming, like they're not gonna be good at what they do. It's just, I've never seen it be any other way.

I started my first mastermind, had our first meeting Friday, and one of the people sells a high-ticket item. I believe he does. He coaches students, like very high-performing students, like people much smarter than you and I.

And doesn't take much for me, but, but you're sharp.

No, it didn't.

It didn't take me.

Yeah. Yeah. So, but it was interesting that he said that he was in the mastermind. Because he knew that he needed to spend a lot of money in order to have the mindset to charge a lot of money. What do you say about that?

I'm vigorously nodding for those that are just listening to the audio. Yes. Yes. Yes. It's such a mindset. It's like, one of the things is, I, you know, I heard this from a coach that I learned from that nobody has a budget for coaching. Nobody needs coaching. It's like, do you want coaching? And so if you're moving into the world of wands, ultimately you're offering a luxury product, right? Again, I don't think coaching— yeah, there's some people that coach specifically around crisis, but again, the people that are coaching probably have the needs to extra spend more on the crisis that's being solved. So since you're anyway selling a luxury product, you have to understand the world of luxury products. So if you're buying a jet, right, or you're buying a watch, a high-end watch or a high-end car or any high-end thing, there's a way that it's marketed. You're speaking to the potential of the person who actually gives a crap about the watch or the wallet or the belt or the car. Like, it doesn't actually matter. But when people go and buy, it's not just, I need this technical service to get me from here to there. The thing that we buy speaks about who we are, who we want to be, how we present ourselves, how we want to be seen by other people, right? So that idea of learning how to think— again, I sent out to my, my coaching group today a reel of watching a guy sell jets. And so the guy's budget was a $10 to $15 million jet, and he was literally selling the way I teach people how to sell coaches. He didn't pitch a damn thing. He asked questions. So how often do you travel? You know, how many passengers do you need? Do you want to be able to stand up? How tall are you? Right. So he was really a trusted advisor as opposed to a guy that's pitching, hey, you know, Hyundai's having a sale right now before the end of the year, you know, get X, Y, and Z. Like, no luxury person is going to buy that shit. It's expensive now. It's expensive later. And the question is, can you afford it? And if you want to afford it, cool. And if not, there's 100 other people that are more successful than you. That can. And if you have that mindset, which only comes by being in the process of being in the world of people who want— again, Elon Musk does not have to work to make money, right? And again, he's working harder than all of us. That's the funny thing. Yes, his net worth has gone to like $500 billion and more than doubled. What is he doing now? He's like running parts of the government. He's running like 15 new companies. He's launching like— he— that's the whole point about the guy getting the mat time in the gym. Like, he's a good guy to coach other entrepreneurs because he's working fucking harder than everybody else. And so that's the idea of luxury being involved with it is like, it's a mindset. And if you're not on the same page, like, can't use his name because I didn't ask your permission, but there's a gentleman that we both know and like, he built a very successful company and in the process his marriage suffered and now he helps other entrepreneurs with their marriages. And it's like, that guy freaking gets it. Because if I'm trying to build a $100 million company and someone that's making $70,000 a year is trying to tell me about work-life balance, I'm like, what the fuck do you know? We're not in alignment. But if this guy said, I built a $100 million company and this is how I can do it. So then I'm automatically gonna get it. I'm sorry, I overtalked.

Go ahead. No, no, you're highly caffeinated this morning. I love it.

Yeah. God, it's a problem.

Let's go back to, let's pivot a minute. When, when you and I first started, you came along with another advisor, a marketing advisor that I had hired. And when we started working together, I didn't really know what I wanted or what I expected, but We ended up spending probably the first 6 months that we worked together on what I would call personal, not business, specifically around my marriage, which was in crisis at the time. And, you know, looking back on it, I understand that personal and business is intermingled. You really can't— if one's suffering, the other's suffering. If you're suffering at home, you suffer at work and vice versa. What do you see with that interplay with, like, between the personal and business life and, and, and how you approach coaching?

When a person is out of alignment, then you see it in all the crazy ways. The business is usually, again, and it depends obviously on how big the organization is and how directly the, the person in charge of it is in control. Again, in, in most places where I work, like the, the executive, the CEO is like very much involved. I, I try to work with people whose hands are on the business. If we're working with someone that, you know, runs a very large agency and like he's more or less offset everything, okay, so maybe it'd be a little bit different. But there's a very, very clear line between— and I actually had to get corrected, I'll be very honest about this. I actually had to get recalibrated by one of the coaches I was working with cuz he said, what are your big goals? And I outlined my financial goal for 2025. Then I outlined my, my relationship goal, and then I outlined my spiritual goal. And he's like, great job. And it's reversed. And he— and I was like, shit, you're right. So at the end of the day, forget about the relationship. Usually when a person feels in alignment with their higher power to whatever extent. Again, I think that there's enough people that you and I, like, between people that believe in God, there's enough people out there. This is not crazy that if you're in alignment with God and you're feeling that you're feeling good with that, that's going to be pillar number one, right? If a person— again, I'm not— and there's all kinds of people we can speak to that don't have that relationship, whatever it is. But let's just assume you are a run-of-the-mill person that believes in God, right? So that's got to be lined up and working well for you. And if it doesn't, that's a big problem. That will trickle down into your relationships with your marriage, your kids, yourself, and then that will trickle down into your business. If not, you're always going again because, you know, at the end of the day, it's interesting. Like you learn this in, again, I don't know why I'm doing jiu-jitsu, but also in weightlifting. It's like, you know, if you try to do a chest press, you know, like you're trying to bench press and you're primarily using your shoulders or your triceps, those are much smaller muscles than your chest. Your chest is big. The big parts of the big muscles of your legs are big, but if you're trying to use like the smaller muscles to move big weight, it won't work. So spiritual alignment and relational and self-alignment is always gonna be those are the big muscles that allow us to make the changes in the business. Otherwise you might wind up hurting yourself in the process because you'll overwork or whatever it might be, cuz you don't have the horsepower to really power yourself through your business if those things are out of alignment. Does that make sense the way I presented it?

No, it, it 100% makes sense. And, and in retrospect, that was my experience. I mean, as my marriage healed and then, and then flourished, uh, my business did too. But I think that, to your point, had I tried to just fix the business, I don't think that would have worked.

I mean, I—

to me, the problems that were presenting for myself were so intertwined and so common, like the feelings that I had at work were the same ones that I had at home. Like, I couldn't address it in one capacity and not address it in the other, if that makes sense.

100%. Yeah, 100%. And again, like, I think that, again, you're dealing— if you think about business, you know, like, you have— there's a lot more complexity because you're dealing with multiple people, both within your company, the customers. There's many, many, many more variables out there. When it comes to you and your spouse or you and yourself, there's it's, it's more simple. It might seem more complex, but there's really only one or two players involved. So that it's actually the easier part to start with because there's less complexity involved. And once you can kind of heal in that area, it will then translate over to you being fully able to have the capacity to focus. Again, if you look at it, Rome fell not because of any external thing, but it fell because it ate itself from the inside. And so a bad relationship with God, with ourselves, with our spouses those are internal threats, the enemy within. And once you can get that whole, like, there's very little things that'll break a person. But, but if you don't have that whole, you could have the best organization, the best business. I've actually seen it and it gets, it gets torn to shit because, because the person was, was, was self-destructing. They were spending all of their money. I, I actually have a, I have a, I have a client. I had a client and just their turnover rate was costing the company somewhere in the neighborhood of over $100 million a year. They were a big company. Company. And I remember hearing that one of the executives was spending so much money on art, on watches, on cars, on this, on that. The whole company was basically just became a piggy bank for this guy, and it more or less bankrupted. And surprise, surprise, the guy didn't have a great succession plan. The guy didn't have a great relationship with— the relationship with the spouse was not— was non-existent. It was really, really tough. And again, I was picking one, but there was actually— I've had 2 or 3 clients like this. The Chris Project is sponsored by the Rupp Group Coaching and Consulting. If you are interested in implementing some of these suggestions that you've been hearing about, or in general you feel like there's parts of your mental game or actually your implementation strategy that you feel is lacking and you love the opportunity to actually start to build yourself into the person that can create the success that you're looking for, please reach out vis-à-vis the link in the show notes to grab a free consultation with us to see if we can help elevate your mental or your business game. Thank you very much.

You mentioned the triad of personal— well, when you were defining your goals, it was, it was relationship, money, and spiritual. And, you know, I'll substitute business for money because that sounds better. So my experience, and maybe, maybe this is just my lack of experience or the people that I've engaged with, but spiritual doesn't seem to be on anybody's radar. It doesn't seem to be. And maybe it's just the circles that we move. But like, so what you, what you're saying to me, what I'm hearing is that Do people that come to you for coaching present with that symptom? Like, I don't know my purpose. I don't know why I'm here.

Like, I actually, I actually gave 3 of my clients, pretty, and people who I was trained to coach, like a lot of shit about that specific, 'cause they're like, I help busy entrepreneurs find their core purpose. I'm like, I'm not hiring you for that. Like, you gotta speak the, again, like most, again, I'm, I'm probably being deeply misogynistic, I think that most, at least men who do big things, or even if they don't do big things, attempt big things. And again, even building a small business is a very big thing. It's not fricking easy. It's selling one product is not— it's hard. Everything, you know, it's not, it's not simple. So when you have people like this, to have an outside person come to you and say, I'm gonna help you find meaning and purpose and alignment in your life. Like, we're like, get outta here with that shit. I don't need that. You know what I'm saying? So there has to be a certain level. Again, that's why the person that you— that we both know is very compelling, who had that big exit, it's like, okay, that guy knows what it's like to get his hands dirty. So there has to be a level of rapport and buy-in. So, you know, this guy's actually seen enough shit to be able to help me, right? So again, for some, a veteran or someone that's been through stuff, you automatically give them that kind of credibility. But it's important to see that. So I think that deep down, like all of us are, again, like I think business building is very spiritual. You're literally being like the creator. You're creating something out of nothing. There's value that's being generated. And again, one of the, I saw recently a really cool insight that says the hardest part about business, you, there's no guarantee it's going to work at the end of the day. Like, you don't, you don't know, you know, and you've had all these people and like market conditions will change. I had a client that like lost a crap. I was working a bunch during COVID He lost like a ton of money. And then Elon Musk tweeted something and his, like his, like one of his companies like ticked up like $500 billion and like, it just like— so there, I think, you know, again, the idea is like the luckier you are, the harder you prepare, the luckier you are. Like there's this concept that what we're doing is very spiritual work. And so what I found is the way that I will approach clients around their spirituality, around the relationships, is it has to be through why they're initially hiring me. If you're hiring me to get better in business, we'll look at those things as sort of an— and I won't go like lead with that, but ultimately I think anyone that's been in business long enough and been successful enough will have a sense of humility to realize it's not them. They're not good enough to create the outcome that they've had. And that opens them up to being able to have a deeper conversation about like, what is this all for? What led me to do this? What am I going to do with my wealth when I'm done? What am I going to do with the people I'm helping? And again, I found that— and this is a lot coming from someone that's, you know, I mean, spent a little bit of time as a rabbi. It's like, I think oftentimes, like, building businesses and being in business is the most spiritual work you can possibly do.

That is the money shot right there.

I don't, I don't think a lot of people Different context and different, different language, but that's fine. Keep going. Well, I just don't—

I don't think a lot of entrepreneurs think in those terms that what you just said, that that is spiritual work. Is that your experience, that when they come to you, they understand that spiritual impact?

If they don't understand— I mean, again, the idea is ultimately you bring people for what they want, but you sell them what they need, right? So, and the funny thing is, like, one of my biggest mentors and coaches was someone that was completely A religious and works with huge companies and charges crazy amounts of money, but he's essentially saying basic truisms from the Bible and from the Talmud. I like, I, I went up to at the end of like one of his classes, I'm like, you understand like all this stuff is like Jewish stuff. He's like, no, tell me. I was like, are you serious? Like I thought he literally like copied all of our stuff. So the reality is in the world of manifestation, in the world of, of again, just like creating ideas and you look at anyone, I mean, it's the easiest to see in the world of sport because there's like a clear winner or loser. And in business, like again, I, I don't know. I don't know anyone that, like, again, maybe you have a big exit, but then you're like, oh crap, now what do I do with all this money? Or now what do I do with my next step? And that was actually how we met, was the person that connected us. Like, we started working because he was trying to help people exit their companies, and he noticed that the biggest liability was that a lot of the guys that could exit their companies didn't want to because they didn't know what else to do after they leave. And that is a big problem for a lot of people. What do I do? Suffice to say that it helps a person start to realize that these problems are fundamental human condition issues, which kind of implies that we do have a soul and a religious path because ultimately we are doing very spiritual work. What does spiritual work mean? Again, it's providing value. It's creating out of nothing. It's doing the internal work to be able to actually rise to the challenge of the marketplace like that. You need, you can't have an ego when it did you sell it or did you not sell it? Okay. What happened? But it's interesting if you look at people again, I like UFC, so you can see these champions, but like also in the world of like basketball, Babe Ruth, like people call their shots. So the, the human mind, if If you can't see it, you won't be able to get there. And if you get there once, it'll be an accident. But the people that are consistently successful, it's because they've already seen it in their minds. They've created a lot of clarity and framework around it. So when they get there, it's just recognizing where they were going to go anyway. It isn't this new thing that they've already seen.

What are the usual symptoms that, like when you're coaching somebody, not coaches, but entrepreneurs, not to say that coaches aren't entrepreneurs.

That's what I was gonna say. It's, it's all, that's the thing. It's all the same stuff. But go ahead. Let's say I'm working with someone Right. The non-coaching company.

Right. So, so what, what are the, some of the common symptoms they present with?

It's a great question. They usually are held back from what they want. Meaning if, and again, I, I've met people and I literally like, I don't know how I can help them. So usually the people that I work with have a problem or they have a goal or a vision And one of the two things are present. If you don't have a problem and if you don't have a place that you're going or you're already on track to go, so like there's not much for me to do no matter what. I started working with a gentleman that I absolutely love. Again, I tell people he's got more companies than I can count on my fingers. He's older than me, he's smarter than me, he's 100,000 times more richer than I am. So why the heck is he hiring me? So the reality is when we got on a call, what we identified was he like, he was so in his companies he couldn't get out of his companies. And literally what I did was I sat with him and gave him space for him. Again, what the hell do I know to help him? He's done all the stuff that I like. I've never done anything that he's done. Bottom line is though, I created an island in time. He invested a shitload of money and he sat on that island with me and it was like, no joke. Again, I kind of protect the identity of everybody that I work with unless they want to disclose. But like in the third time we met, we had a breakthrough. There was something that had been bothering him for 7 years and we realized through this he solved like 10 different problems with one person and he was like, he could not believe it. I didn't have any idea that was going to happen. But because I work with smart people that are motivated to solve problems and we just give them a space to start investing in themselves and the proper framework to do so, he had all the ideas inside. So those are like my ideal clients and I look like a genius. This, right? And a lot of times I've been quiet and you've answered your own question. You're like, God, you're so good.

And I was like, yes, I was on mute.

Exactly, exactly, right? Like, but that's the point. It's like, I always tell people the best coaches are ones that can find great clients who are more motivated than their coaches to get the results that they want. If my trainer's not in the gym, I'm still working out. I don't give a shit, right? Again, eventually if he's not there long enough, I'll be like, hey, you know, what am I paying you for? But just the experience of paying for it and then showing up and doing the work. If you're a good coach and you find good clients, they'll get crazy results no matter. Like, you just have to make a space and get the hell out of their way. And that, that's one of the biggest things that I see on my coaching training end is I have to help a lot of people because the coaches' egos— usually they're trying to like offer value. It's like, no one needs your friggin value. Shut up. Let the person have their experience and they'll actually create the clarity that they're looking for.

Yeah. And that's one of the things I've realized over the time that we've worked together is that exactly what you said. You give me the space and the framework. And not to say that you don't have wise counsel, you do, but the powerful things have come from within me where I was able to discover those things. And I think it's a process that inherently needs to involve someone else. Like, I, I don't I don't think you can do this by yourself. You think you can, you think you can, but you can't.

And, and, but, or, or why, why would you? Like, technically you could walk 4 miles to the grocery store and carry it all home, but like, if you've got a beautiful, you know, uh, Denali, Denali truck or whatever, whatever you drive out there in Oklahoma, like, why wouldn't you take the damn truck to the store and just put it in the back seat and then drive it home? Probably much more comfortable.

Well, True, true. But I mean, well, maybe I'm just biased and I'm speaking from my own experience. I can't. I mean, like, even when I, as I've progressed and I feel like I have clarity, I still, when you ask questions, I'm like, I don't know. And I have to dig deeper. And it's like, I can't do that with myself. Like, maybe I could, but I haven't figured out how to do that.

Yeah. And I think that's the difference. That's why I love entrepreneurs. And again, like, when I work with other coaches, I tell them, don't go into the space just because you think those are the people with money. If you have a problem, that's— if you're talking to people that are compelled to solve their problems, they have any means at all, they'll spend money. So don't start working with entrepreneurs just because you think that's where the money is. You have to do it because you love it. And I loved it. I've always wanted to be an entrepreneur. I always hung out with entrepreneurs. I always looked up to entrepreneurs. And so it was a natural step for me, even when I was like broken, didn't have a business. But one of the things I love about it is, like you said, is like your ego is low enough that you're able to say, I don't know how to do this, or it'd be really hard for me to do this. Let me just bring in someone who can help me do this better. And so there's a natural alignment with what you're saying is like, technically you're smart, like you're technically smart enough to do it, but like, do you want to do all of the work or do you want to just have like a set time where you can go down that path your own and have— and again, I'll add one of the things you said, wise counsel. The reality is it wasn't wise counsel. You had done enough of the heavy lifting yourself that the answer itself was pretty obvious for me. I just put that— like you had like put the whole puzzle together. There was that one last piece and I'm like, oh, that's the piece. And I put it right there. So you could say, oh, I'm brilliant at puzzles. The reality was you had built the whole puzzle. I picked up the last piece 'cause that was the only thing that was there and I just dropped it in. That's called really good coaching.

Let's pivot once again. So you've talked to me briefly about your childhood growing up and how— I'd like to dive into how that experience has affected your adulthood, your coaching, your marriage, whichever you choose.

With all love and respect to how I grew up, I don't like to compare scars or war stories because, because everyone's trauma is unique for them and it's exactly what they needed and it was as bad as it could be for them, or, and whatever it might be, you know, kind of having a very— I grew up with you know, never seeing my parents happy, um, in their, in their relationship. I was, uh, kind of, uh, I was— what do they call it? I had a measurement of things with my mom. My dad I didn't talk to for 20 years from the time I was about, uh, about, yeah, 18 till about 30 years old. I was actually longer than that. It was about 20, 22 years. Very biblical because that was how long Jacob and Joseph didn't speak. Um, so, and I'm not putting either of us in that category, but just as kind of a cool thing, what constantly grapple with was a sense that I'm not enough or that I— yeah, like, I've dealt with a lot of my own issues around deserving, around being not enough, around am I qualified, am I— do I have a place here, do I have real value to add? And the value that I add, is it okay if it's my own value? As someone that was like pushed really hard in school, like, again, like, I know Tiger Moms is like an Asian thing, but as Jews, I had a tiger mom, um, whatever, whatever, and whatever, whatever, whatever animal you'd put on it and, and would probably sound anti-Semitic, whatever we came up with. But, uh, but I don't know, whatever. Anyway, but, but the, but the idea was ultimately like, can I, am I valuable and is my value not associated with something that's external? So as someone that got straight A's and like did really well in school and went to a great college, like I didn't want to do any of that shit. And I'm like an artist by trade and I really have a hard time following the rules and I can excel in any framework you put me in, but except for the, like, ability to excel in my own life. And so as I get older, really what I want to empower others with is the ability to excel. And again, it's weird if you think about it, because I'm part of a very dogmatic tradition of like, do this, don't do that, God has very clear definitions of what success is. But ultimately, the, the gift that I want to give people is the ability to excel in their own ways and to feel really, really good about their own, their own process for what they're contributing.. And again, that's kind of the underlying theme that again, like it's scary. You need big shoulders. I always point out that there was a Moses and there was an Aaron. And again, just like in the world of entrepreneurship, like how many people are actual entrepreneurs that can actually run businesses? Like 10%, you know, and do it well, like 5%. Most people are like Aarons. Aaron sought, uh, and again, he was a great leader in his own right, but he sought frameworks, he sought order, he concretized the things. Everything was, this is how you do it, this is the steps to achieve. And Moses was out there like screwing up, rugged, with all, with all appropriate respect, screwing things up, cursing God, cursing himself. He ends up failing, not going to the Holy Land. The last thing he says is he's about to die is basically like, I'm just starting to figure this thing out, I'm just trying to figure you, God, out. And we say that, and that Judaism says there's, there's never gonna be a greater prophet than Moses, that the wisest person, the greatest insight. His last insight is like, I don't really even know What's going on over here? I'm just, just starting to get this. Like, it's a very entrepreneurial journey, but ultimately what I want to gift people with, and I, which means I ultimately want to gift myself with, is that sense of unique contribution, but doing it in a way that's, that's, that's a person feels good with and, and, and can feel confident in the contribution they have.

You said something, you could succeed at any framework, uh, and I'm paraphrasing that except in my own life. Is that the way you still feel?

I would love to tell you the answer is no, and that would be a complete lie. It's a process. I'm much more me again. Like, you look at— it's almost weird to hear people's reflections on me and then to be inside of me hearing people's reflections. Anyone with body dysmorphia will totally get that right. What do you see when you see me? Like you said, you're like, Wow, this guy's got big muscles. And, you know, I park my big loud car right in front of like, you know, and it's like I present a certain way and people know me. No, I'm not. I mean, a lot depends on who you ask, right? People know it's not about— I don't like, you know, it's not about the money, it's not about the muscles. It's about, you know, like, again, a fat guy with no money working hard on, on, on. And if I can do it, anyone can do it. That's, that's the, that's the modality I try to give out if you, if you actually get to know me. But it's very weird hearing kind of the difference between how I feel about myself and how others feel about themselves. There's been like a lot of personal stuff I've gone through as of late, which has also like created a tremendous amount of like humility for me. Like, oh, you know, like I had a really bad relationship with a partner, which was so obvious. I would never— again, I do this professionally. I would have never gotten in this situation. And it was really like a kick in the nuts, honestly. And but it gave me humility and I was like, I was able to turn it into a lesson. So the reality is I'm kind of like Moses said, like I'm on the path, I think. And if it was good for Moses, I'll just try to follow that same path. That's a nice way of saying no, I don't feel like I've gotten there.

Okay. Well, I appreciate the candor. So have you reconciled to your father? Yes.

And I found— I'll see if I can do it without getting choked up. But having my father having two failed marriages and not being able to talk to any of his kids, he ended up— he lives in Austria now. And again, he was like the big, strong, like, big, strong Rush Limbaugh conservative, like, you know, 6'2", blue-eyed, like, tough dad that And when I reconnect with him, he's much, much older now. He lives in a small one-room apartment. He's all about the communist lifestyle. You know, every, every Republican value that he used to embrace. Now he's like a hardcore, like socialist, communist, European, you know, that Trump's going to take, destroy the world and whatever it is. And, you know, and I'll come to him with like, like, I don't give a shit about Paul. Like, after I became a rabbi, like, I realized, like, in most cases, it just divides people.. And so I don't care about that. And I want to like the real stuff, like, you know, what do you regret the most? What would you wish you had done better? And the crazy thing is I've turned to him at really hard times and he's said, I can't do this. I don't know you and it's too hard for me to go back. And I remember sitting on the airplane with my daughter who's 16, and sometimes she has a hard go of it and sometimes I have a hard go of it and sometimes I have a hard go of being her dad while she has a hard go of it. And I, I remember telling her, like, the lesson that my dad taught me was no matter how badly you screw up, your kid still needs you to be a father. And so I told her, like, I will screw up, but until I die, I'll do whatever it takes to be the father that you need me to be. And so I did reconcile with him and, you know, he should live long and, you know, be healthy and all the things. But I think the lesson is that I learned from him. I— you can learn from people either by what they do or what they don't do. And I think I learned a lot from what he did, but I learned a lot more by what he didn't do and what I need him to do. So I try to keep that front and center as I go through my life.

Yeah, I think it's interesting. My own experience with my mother, I'm realizing that, like, I'm going to have trouble putting this into words because it's still kind of a new thought for me, is that, you know, the people that we, like our parents specifically, who are very influential in our lives going early on and very formative in how we see the world and what we believe. One, understanding that they're, you know, as an adult you understand they're just people, they're not gods. They're, they're, they're, you know, as a child they're God because they control everything, right? But that one, that they're human, but two, that your perception of them is fundamentally skewed. Like, you, you see them through a lens of what you needed or wanted at the time, but, but that's not who they are. I don't know if you have any insight into that from your experience, but like, and I don't know how to say it any better, but it's, it's like what I thought I was missing from my mother never really was there, I guess is what I'm saying. Like that.

Yeah. Yeah. It's a beautiful reflection on our own needs, what we would have needed on with tremendous humility, realizing like we put a lot of that on people that might not have had the capacity Yeah, in all cases, because our parents like want to care about us, like we're parents, we want to care about our kids, but there's— sometimes we can't, and sometimes we do the best and it doesn't work. And so I think it's, it's a, it's a tremendous lesson around our own needs, humility, you know, release, forgiveness, you know, the idea that just the fact that they brought you into the world, like, that's enough. And everything on top of that, that we were gifted, you know, is even better. And, you know, one of the things that Julie says a lot, because I was— she was comparing— sometimes I don't like doing homework because of where I came from. And she said, hopefully I don't get in trouble for this. And she said, you know, she's like, well, I really need you to be around and engage more with the homework. And I said, you know, my dad was passed out drunk every night and like, at least I come home. And she was like, the bar's a little bit higher for you, I think. Yes. But the reality is like, even if he had just had me and never came around ever, like that would be enough. And the fact that he supported my family for as long as he did and he put a roof over my head and like all that stuff. Like, you know, it just, it just kind of brings us back. I think when we look at our parents with a sense of humility and appreciation, which is the healthy release for all the shit that people did to us. And, and then, you know, kind of looking at ourselves and our own relationship with our children is like, I want to do the best I can. And ultimately they'll probably come to the same realization somewhere down the road that we were just people doing, doing what we could in order to, to do the best job.

Yeah. Yes. As Jordan Peterson says, you know, you know, you're successful if you have adult children that you want to spend time around.

That's ultimately the goal. I, unfortunately, I have to jump off. I have like a, I have a hard stop around now. This was like, this is like your show. So it's so, it's so preposterous to me to suggest we do, we do more of this, but I had a great time. Maybe I should make my own Chris project so I can have you on.

Well, you're welcome to. So give us a clip on how we learn more about Jacob Rupp and working with you?

Yeah, I mean, I think that we, we have a link in the show as it is. Rupp-Group.com has all of the background about me and ultimately the people I'd be looking to work— I train coaches for a living, so there is not one problem that anyone listening to this would have that I don't have someone that could probably help you in terms of the people I'm looking with, like looking to work with myself. Either A, if you have an inkling that you'd like to monetize some of your skills and, you know, help other people, which you can and you should. A little bit biased, but I think that that ability— again, if I could have worked with Christian Brim when I was, you know, up and coming, I think I could have, you know, made all kinds of— made different choices in my life. If that's you, or if you're looking to resolve some of the challenges you have or get to where you want to get to faster, that's what I do.

So. Well, Jacob, thank you very much for your time. I appreciate it. Shabbat shalom.

Shabbat shalom to you, sir. This is amazing. It's fantastic. Even just like a Tuesday, this is the best. All right, thank you so much.

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