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The Deep Wealth Podcast - Extracting Your Business And Personal Deep Wealth
The Deep Wealth Podcast - Extracting Your Business And Pers…
As a busy entrepreneur, you know how to build a successful business. But here’s the harsh reality: The skills that built your business are not the same ones that will sell it. And if you think you can wait until the last minute to prepare for your exit, you’re putting everything you’ve worked for at risk. Why Should You Care? You’re not alone in thinking you can prepare for your exit when you’re ready to sell. But this common misconception can cost you millions. Up to 90% of liquidity events fail because owners mistakenly believe they can just "wing it" when the time comes. Don’t be one of them. The Deep Wealth Podcast is your no-nonsense guide to ensuring you don’t fall into this trap. Hosted by Jeffrey Feldberg, who went from living in his parents' attic to a 9-figure exit, this podcast gives you the exact roadmap you need to avoid the mistakes that ruin most exits. Here’s What You’ll Get: * Immediate Action Steps: In each episode, you’ll get practical, no-BS advice that you can implement right away to start preparing for your successful exit—without wasting time. * Expert Insights: Learn from those who’ve been there. Jeffrey and his guests break down the hidden pitfalls and what it really takes to create a business that buyers can’t resist. * Time-Saving Tips: We know you’re busy. That’s why every episode is packed with concise, actionable strategies that fit into your hectic schedule, so you can prepare for your exit without sacrificing your day-to-day operations. Why This Matters Now The longer you wait, the more you risk leaving money on the table. Your business might be thriving today, but a poorly planned exit can turn your success into regret. Don’t let the skills that built your business lead you to make costly mistakes when selling it. Subscribe to The Deep Wealth Podcast Make the smart move and start preparing now, even if selling is years away. The best deals go to those who are ready—are you?
Sept. 29, 2026

CEO Advisor Rajesh Nagjee: Your A Players Are Becoming B Players Because of You (#581)

CEO Advisor Rajesh Nagjee: Your A Players Are Becoming B Players Because of You (#581)

Send us Fan Mail “The day you decide you will do it.” -Rajesh Nagjee Exclusive Insights from This Week's Episodes Your A players may be getting weaker because of how you lead. CEO Advisor Rajesh Nagjee reveals how founder dependency kills ownership, slows growth, and keeps you trapped as chief problem solver. Episode Highlights 00:07:51 How Rajesh discovered he was turning A players into B and C players 00:11:12 Why delegating tasks can quietly create contractors instead of owners 00:12:38 Th...

Send us Fan Mail

“The day you decide you will do it.” -Rajesh Nagjee

Exclusive Insights from This Week's Episodes

Your A players may be getting weaker because of how you lead. CEO Advisor Rajesh Nagjee reveals how founder dependency kills ownership, slows growth, and keeps you trapped as chief problem solver.

Episode Highlights

00:07:51 How Rajesh discovered he was turning A players into B and C players

00:11:12 Why delegating tasks can quietly create contractors instead of owners

00:12:38 The rule Rajesh introduced that forced his team to stop depending on him

00:20:14 Why fixed processes can create variable results and weaken ownership

00:26:07 How to confront poor performance without making your A player defensive

00:32:29 The overlooked relationship factor that can sabotage productive KPI conversations

00:45:31 The simple listening habit that can instantly change how your team experiences you

Full show notes, transcript, and resources for this episode:

https://podcast.deepwealth.com/581


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581 Rajesh Nagjee

Jeffrey Feldberg: ​[00:00:00] What happens when the business you work so hard to build becomes the very thing that takes away your freedom? Rajesh Nagjee knows the tension firsthand. He built his first seven-figure business early, only to discover that growth had created a dangerous dependency.

Decisions flowed through him. Vacations were interrupted. Strategic thinking was pushed aside, and the company could move only when he was there to keep it moving. That realization forced him to rethink what leadership and scale actually mean. Over more than three decades, Rajesh has built, operated, advised, and transformed businesses while mentoring nearly four hundred CEOs across dozens of industries.

His work today centers on a deceptively difficult question: How do you build a company that performs at a high level without making the founder the permanent safety net? His CEO Freedom OS [00:01:00] grew from years of working inside that problem, helping leaders rethink decision ownership, accountability, operating rhythm, and the role the founder should actually play.

Rajesh has also facilitated nearly two hundred YPO and CEO forums globally, co-founded successful operating businesses in Dubai, and spent decades studying why talented founders remain trapped inside companies that look successful from the outside. His story raises a bigger question every founder eventually has to confront: Did you build a business, or did you build a more sophisticated job for yourself? 

And before we start this episode, a quick word from our sponsor, Deep Wealth and the 90 Day Deep Wealth Mastery Program. Here's Jane, a graduate who says, and I quote, the Deep Wealth Mastery Program prevented me from making what would have been one of the biggest mistakes of my career. I almost signed on the dotted line with an unsolicited offer [00:02:00] that I now realized would have shortchanged my hard work and my future had I accepted that offer. Deep Wealth Mastery has tilted the playing field to my advantage.

Or how about Lyn? Wow, he gets right to the point, and I quote, Deep Wealth Mastery is one of the best investments ever made because you'll get an ROI of a hundred times that. Anyone who doesn't go through this will lose millions. 

And as you're listening to these testimonials, are you wondering if you have the time? Are you even thinking that you've got this covered, you have the advisors or people in your network? Well, I got to tell you, these myths, they're often behind the 90 percent failure rate for liquidity events. Think about it. You have one chance to get it right for your financial freedom. You really want to make it count.

And when it comes to time, let's hear what William has to say. We just got in this testimonial, William says, and I quote, I didn't have the time for Deep Wealth Mastery. But I made the time and I'm glad I did. What I learned goes far beyond any other executive program or coach I've experienced. 

So what do you think?

As I hear that, [00:03:00] that's exactly what gets me out of bed every day. That's my mission. That's the team's mission here at Deep Wealth to literally change the social fabric of society. One business owner at a time, one liquidity event at a time, and my Deep Wealth Nation, what I want you to know, the Deep Wealth Mastery Program, it isn't theory.

It's from the trenches. It's the only one based on a nine figure deal. And that deal, that was my deal. You know my story. I said no to a seven figure offer. I created the system that later on, myself and my business partners, we said yes to a different buyer, a different offer, a nine figure deal. That's what we now call the Deep Wealth Mastery Program or the Scale For Ultimate Sales system.

It's built by business owners, for business owners, so if you're interested in growing your profits for preparing for a future liquidity event, and that may be two years away, it could be 22 years away, whatever the time may be, you want to do this now, and you want to optimize your post exit life, Deep Wealth Mastery is for you.

To get started, email success at [00:04:00] deepwealth. com. Again, that's success. S U C C E S S at DeepWealth. com. You'll receive all the information about the Deep Wealth Mastery Program or better yet, why not hop on a complimentary strategy call.

We'll go through exactly where your business is today and what's standing between you and your financial independence and your dreams. So that's where you want to be. You want to be with other successful business owners, entrepreneurs, and founders, just like you they're looking to grow their businesses, create markets.

Market disruptions and unlock their financial freedom to get what they deserve. And whether you've been in business for three years, 40 years, you're a startup, you're manufacturing you're in high tech, low tech, whatever the case may be, coming in and network with other business owners, it's a safe space.

It's a confidential space with business owners, with businesses just like you, because they all wanna lock in their financial freedom and enjoy both success and fulfillment. So again, the 90 Day Deep Wealth Mastery Program, it has your name on it. All you need to do is take the next step. Please [00:05:00] send an email to success at deepwealth. com.

Deep Wealth Nation, welcome to another episode of the Deep Wealth Podcast. Deep Wealth Nation, let me ask you this. Do you have the golden handcuffs? Did you start your business with all these grandiose plans and you're just doing so well? The business grew, the demands grew. Next thing you're doing everything.

You've got the whole, the golden handcuffs. You don't have that lifestyle that you wanted. What do you do? How do you get help? How do you fire yourself? And that's one of our favorite questions here at Deep Wealth, especially with the Deep Wealth Mastery program for founders. We ask you, do you run the company or does the company run you?

Sadly, for most founders, the company runs them. So what do you do? Where do you start? We have a very special guest in the house of Deep Wealth. We have a fellow founder, entrepreneur, someone who is globe-trotting, who is helping CEOs, founders around the world go from where they are to where they want to be, and even created his own operating system for business, but I'm getting ahead of [00:06:00] myself.

Rajesh, welcome to the Deep Wealth Podcast. An absolute pleasure to have you with us. There's always a story behind the story. What's your story? What got you from where you were to where you are today?

Rajesh Nagjee: Jeffrey, I just love being on your show. And it's so uncanny that the shirt that you're wearing, the shirt that I'm wearing, your background, my background, the sofa there, sofa here. We didn't plan any of this. So what got me here is a very interesting question. And one of the things that you'll find slightly different about me is I'm a straight shooter, number one.

And number two, I will tell you every damn thing that went wrong in my life

Jeffrey Feldberg: Mm-hmm. Love that

Rajesh Nagjee: so I reached where I reached because of series of mistakes, blunders ran a few companies in the ground and fell off the horse several times including physically broke my leg. And and here I am.

And so the difference between, business schools where we have some very, [00:07:00] very intelligent, sharp successful pro- professors who will tell you everything about a business starting from, the journalistic pursuits of going into a business and breaking it up, and then giving you the whole design of it, to philosophy, to history.

I'm a student of physics. That's the difference. And the thing about physics is, only if the damn car works, it works. You can't explain it away. And so that's been my pursuit for 30 years, and I've had the privilege of working with over 350 founders and CEOs, and I tell them upfront, "Listen, buddy, I haven't got my life handled.

I have taken businesses to the ground, and if you are interested to work with somebody who likes to roll up his sleeves, open the hood, and go inside with you, tinker around, doesn't know what the crap he's doing, but at the end we'll get it done." So we'll figure it out. And that's basically what got me doing what I'm doing and, all these people have been so generous.

[00:08:00] And what they tell me is they love my honesty, that if they ask me a question, if I don't know, I say, "Hey, buddy, I really don't have the answer to that, but let's try and figure it out." So that's the one way of answering that. The other way of answering that is I started out in in life in my ancestral business, which was established in 1880.

One of the things that we do is we manufacture umbrellas, and we trade in many different things like textiles and shoes and cigarettes and all the rest of it. And you can imagine from 1880 till today it's a lot of years. And so I, after college, joined my family business, was there for 12 years, then started getting bored because of the routines and because of, the family.

And, actually straight out of college, my definition of business is about managing people's upsets. Because I was surrounded by cousins and uncles, and all I was doing was walking on eggshells Long story short, I took a sabbatical for three and a half years, studied [00:09:00] music.

I was already studying music, but very deep into it, Indian classical music. Then I got inspired to build a hospital, so I built and ran a hospital for 12 years, and I learned the protocols of how do pay attention to one criticality with most businesses miss. So there are three criticalities of every business.

One is quality, which is critical. Second is cost, and third is time. So quality and cost, everybody will talk to you about. But when it comes to time, how do you manage time? That's what I learned the hard way inside of the life and death protocols of a hospital, and that's one of the big things that I bring into all my work to get the whole teams galvanized to deliver on time, deliver within budget, and so on and so forth.

So this is the background. In the end, when I got fed up of running the hospital because, hey, I'm not a doctor, what do I know about saving life? I discovered that I have the talent to coach, so I got trained in 14 different disciplines, spent 80,000 hours on my craft [00:10:00] to apply physics to business, and that's what I've been doing for the last 30 years applying physics to business and having a ball.

And my, my, the last thing is my life's purpose is to make friends, have fun, be playful, and make memories

Jeffrey Feldberg: Wow, what a terrific mission. Like so many founders and business owners, we're helping people make their lives better. And as I like to say, when we help enough people get what they want over time, we get what we want, and in that order not the other way around. But let's go back to a few things that you've said.

And I know in preparing for today, part of your story was for your first seven-figure business that you created. From the outside looking in, hey, this is a success. It looked incredible, but I also know back to what I referenced earlier, you had the golden handcuffs. Every decision, every important decision was always coming back to you.

And so when did you realize, "Hey, I haven't built freedom. I've got [00:11:00] dependency. I've got these golden handcuffs. I've got what otherwise known as a J-O-B instead of what I wanted"? And when did that realization come to you, and then what did you do about that?

Rajesh Nagjee: I was super excited when I started my hospital. Every single day, I would start by 9:00 in the morning and go on till past midnight. And it was fun, it was so exciting, so exhilarating. And then slowly, I started realizing that everybody else is going home at about 7:00 or 8:00, and I'm sitting there till midnight.

And so there's something that I haven't figured out. And then I realized that I've got really mediocre people. My people were there, there's no ownership that was showing up and so on and so forth. And then I started checking with the HR and said, "Hey, how come you got these mediocre people in the hospital?"

So the HR looked at me and said, "Listen, sir, you pick the best of the [00:12:00] best. You were so nitpicky. You sat through all the interviews." That's when I realized I'm a damn good coach, that I took fantastic A players and consistently converted them into B and C players. What a conversion that was. And this was consistent.

And then, I started realizing that it's basically, being the chief problem solver was giving me an adrenaline rush, and I was a junkie. And that's when I started realizing that, look, there's more to this in life. I've got family, I've got parents, and I wasn't there for any of that.

And so I took three days off and started, writing things down on my pad. And the first thing I realized is that the moment I hire somebody who's very smart to run any of my departments, they hire me right back as the chief problem solver. And and I really enjoyed the golden handcuff.

The, the truth be [00:13:00] told I had the ball during that period. And then I said, "Listen, things have got to shift." And that's when the trouble started. So I will wait for you to say something, and then I'll share the trouble

Jeffrey Feldberg: Yeah. And I'm right there with you being that adrenaline junkie. "Oh, the team needs me. I'm the only one in the world that can do this. It's gotta be me." And then you get that win, never mind all the other constraints that come along with that. "Yes, look at this. Look what I was able to do." And it takes a vulnerable person, I'm not even gonna say a strong person, because being vulnerable is being strong.

It takes a strong person to say, "This isn't right. I really wanna fire myself, bring someone in who's even better." And as you've done, hey, I don't wanna take A players into B and C players. I wanna take A players and make them into A++ players, and then replicate that throughout the entire organization.

So with that in mind, I would love your insights. This is one of my favorite questions. If we use this fancy term, Pareto's law, what some people call the 80/20 [00:14:00] principle, you've worked, Rajesh, with countless CEOs, founders, business owners. With the 80/20 principle, is there a pattern or maybe a few patterns?

"Yes, Jeffrey, this pattern over here. There's one pattern or these two or three patterns over here. This is what's creating 80%, 90% of the same issues across businesses, industries. Regardless of your station in life and business, it's creating these issues." Anything come to mind for that?

Rajesh Nagjee: Oh yeah, absolutely. And before 80/20 is born, there's 100 And hundred is the founder or the CEO, and he really is the one who creates the whole total mess. Then he gets tired, so then he starts putting things out and he gives things away to people. He calls it delegation. Except that what is he delegating?

He's delegating very intelligent stuff. He's delegating projects, he's delegating tasks, and he's [00:15:00] delegating scope. When you have that combination, you have created you're created vendors and suppliers because that's what you do with your subcontractors, that or with your contractors.

There is a project, there are tasks, and there is scope. And that, then you start looking for partnership. How can you get partnership when you set them up to be contractors? So that's basically the whole mess, that I went through. So let me go back to my story and connect with your AD20 if you will allow me a minute.

So when I got this realization that all of my people were hiring me right back, I was obviously trapped in a hundred one. So I was the one doing everything. Then I took everything out of my office. I had a hard table and all the rest of it, and I set it up like a, a drawing room with sofas, plants, uplighters.

And then I made a few rules. So the first rule was nobody's allowed to bring a single paper into my office. [00:16:00] There were no papers. You come, you talk, you go away. The second, which was... And everybody liked that. "Oh, this is great. Fantastic. We can just go and chat. No problem." The second thing, a week later, is what killed them.

And that is that I got a board made and put it outside my cabin. Sir is not allowed to think. So, and then my people would walk in, say, "What do we do about this? What do we do about that?" I'll take them out and say, "Hey, look at that. Sir is not allowed to think. Go away." They hated it. So now the question is, if sir is not allowed to think, what is he allowed to do?

He's allowed to choose. So you have a problem. You got, this solution, you got that solution. Figure it out, come to me, and I will choose. And the choice is always, man, if I got to choose, I don't need you. Why don't you choose? So the guy goes and says, "But sir, so how do I..." I say, "You go ahead, choose."

And one or two times you'd get it wrong. If you, if it consistently and persistently, you-you're getting all your [00:17:00] calls wrong, then you and I know you can't last here. So go for it. So that's basically how I started working with people and turning them around. And then I started just looking at the twenty percent of the things I needed to look at, freed up eighty percent of my time.

And it's just a question of Being absolutely firm about what is it that you want. If you want to be an adrenaline junkie, be my guest. The statistic is horrible. It's there in front of all of us, that businesses fail to grow. Ninety-five percent of businesses fail to grow. Seventeen percent grow very slowly.

That's not the purpose of business. Forty-eight percent hover around the breakeven point, and 11% get into a debt trap, and 19% go bankrupt. So again, if you look at it, 19%, and the rest is 20/80 Pareto principle. So if you do this and do the math and look at it properly, you will find Pareto principle everywhere [00:18:00] in different ways in which you slice it and dice it.

So now the question is, if 95% of businesses fail to grow, who are these business owners? Who are these founders? Turns out that they are very educated, very smart, very intelligent, and very capable. So obviously, they're doing something that's resulting in that mess, and that something that they're doing is they're consuming a diet which is making them obese, and that diet is really what you need to look at.

What is it that you're reading? What is it that have accepted just because it's written in a book? The only way in which you can make anything work is by directly working with things. If you want to fix your car with something, you got to open it up and then put it together, and if it doesn't work, get a mechanic.

Do what you need to. It's a physical science. It's all about physics. So that's basically You know what my whole journey has been. Now coming to your question about 80/20 I have a [00:19:00] next version of the 80/20, is that if 80% of the results come from 20% of the work, and you apply that principle another one more round, then 80% of 80% is 64%, and 20% of 20% is 4%.

So 4% of your work gives 64% of your results. And that's all I do. I just focus on the 4%. I train people, let them out, and if you really look and come into any of my companies, I've got several companies you'll say, "Hey, this guy doesn't talk to people, doesn't look at papers, he's totally abdicated everything," but everything is running and things are working well.

And I can tell you my teams, my, all my operating people, they're producing better results than I could ever produce. It's just a question of that mindset. It's not a system. It's really about what is it that you're after? What is really precious for you? What is precious for me is to spend [00:20:00] lavish time with my son, with my wife, with my parents.

My mother just passed away. I spent four and a half months with her in Bombay leaving everything here. So it's just a question of, me turning around and telling my managers, "Listen, I don't have time," as opposed to telling my family I don't have time. That's a commitment, right? If you make that commitment, the world starts to work.

And the last thing is the world is not organized to create the result you set out to create. So you got to take the machete, go there and chop and make your path through. If the world is organized for you to create the result you want to create everybody will create it. So this is basically, it's about who are you being, that's the mindset.

And if you really want to work with me, there are a few things you got to be very clear about. That I'm a no-nonsense person. I call a spade a shovel. And I'll tell you upfront, I don't know, I don't have the answer to that, but together we'll [00:21:00] figure stuff out. And I'm also a liar. I will lie in your face because I'm really interested in you figuring it out.

I'm not interested in taking the credit. I'm just under my watch, you're gonna take off. So that's the long and short answer.

Jeffrey Feldberg: Absolutely love that. I'm gonna lie to your face. I may have the answer. I'm not gonna tell you, though. You've got to figure it out on your own.

So let's go back to something that you mentioned that I know for myself, I'll put myself under the microscope, I have failed at miserably. Even to this day, I still find myself making this mistake, and it's a bit of the Goldilocks principle because we can delegate, we can automate, we can eliminate through automation or now with super intelligence, all kinds of different tools, but there's also a fourth category that, especially early on when I started my own business journey, I would abdicate.

Fancy word of, "Hey, Susie, great to work with you. Here's what I want. Go figure this out. Let's talk this time next [00:22:00] year, see how you're doing." But then on the flip side of that, when we're delegating, I'm phoning Susie up, I'm gonna over-exaggerate, I'm phoning Susie up every half hour. "So how are things coming along?

What's going on? Share with me where you're at. No, no, No, don't do it that way. I want you to do it this way." And in Deep Wealth Nation, when we are working with them through our 90-Day Deep Wealth Mastery Program, this is one of the most difficult areas for them. I'd love your insights and strategies of dealing with this because what I often hear, and I've done this myself, "Jeffrey, I've just stopped handing out or delegating different tasks because last time I brought someone aboard, they failed, or they were too slow, or they just didn't do it as well as me, so it's just easier if I do it myself.

I don't want to fall into that trap of having to depend on someone else, and now I'm at their peril." So how do we get that just right amount of focus where I'm not abdicating, "I'll see you this time next year." I'm not micromanaging, "Hey, let's check [00:23:00] in," again, over-exaggerating, "in 30 minutes," but it's the right amount of delegating or, "Hey, why are we even doing this in the first place?

Why don't we automate this? And let's just find other areas, more productive areas that, that we can focus on." As the founder, how do I strike... I'm not even gonna use the word balance. How do I strike that right blend that's the quickest path to success?

Rajesh Nagjee: So what I discovered about myself, and I can really be very honest and very harsh because I'm talking about myself, right? What I discovered about myself is, I really thought I knew delegation, and turns out to be a complete hoax, a delusion, and ignorance. And then I started researching delegation in physics, and what I really discovered is something beautiful, that there is something called, fixed outcome and something called fixed process.

And everybody, for some reason or the other, has this great love affair with process and [00:24:00] systems and quality and all the rest of it because there seems to be some safety, around that. "Oh, I have my quality manual, I have my systems, I have this, I have that." Just think If you're gonna follow a fixed process, all you're gonna get is variable outcomes.

But if you're gonna follow fixed outcome, then with variable outcomes, you will get that result. The best way to test this is, assuming you like coffee or you like tea, doesn't matter which, write down your recipe, the way you make it, nobody else's. And then you take a vow that for seven days, every single day, I'm gonna make that tea and coffee following my recipe.

And then you see what happens. Seven days, you're gonna get variable coffee or variable tea because you followed a fixed process. But when you're actually making tea or coffee, you want this fixed outcome that it's got to have this flavor, this taste, this [00:25:00] color, whatever. And then, depending on the input, little bit this, little bit that, you jiggle this, jiggle that till you get that outcome.

So that's fixed outcome, variable process. Now, it's so easy if you get that, you start getting into actually what is delegation. So what there is to delegate is not projects and not tasks and not scope, 'cause when you do that, you're creating a bunch of contractors, and contractors are never gonna have ownership.

Then you say, you talk to your wife, "Mary, look at these guys, I had the best and, I've got to work. They don't take ownership." Damn right they're not gonna take ownership because you didn't set them up for ownership. For ownership, you got to do two things, give them the outcomes and give them agency to figure out their process.

So you start figuring out the outcome. And this is a difficult piece because nobody knows what is the outcome that they want. So they just hand over stuff. It's all vague. Now, you, when you're running [00:26:00] it you're driving like a crazy person, long hours till you get it right or somewhat right.

And then you give it to somebody expecting that your mess, they will be able to sort out and give you the result you want. Not gonna happen. So you got to take some time off and figure out what is the outcome And once that outcome is clear, then can you actually deliver that outcome yourself? Then build, operate, and then turn over the outcome, and you start moving.

So that's the delegation begins when you give outcome and agency for process. It's your process. This is the outcomes that I want. Budget, time, quality, complaints. I don't want any of the, the downside. I want all the good stuff. Figure it out. If you have a problem, come talk to me. We'll have conversations.

And that's how delegation really starts. So delegation begins when you throw out that word delegation altogether. When you start treating people like, between me and my wife and we were bringing up my [00:27:00] son we are a fabulous delegation system where we were both there when he was a little baby.

He would cry in the night, and either she would get up or I would get up, and we look after him. And we never had this, "That's your job, and that's your job." There was a commitment. And from that commitment, if I'm a little lazy or sleepy, I said, "Darling, can you take care of him now?" Yeah, don't worry.

Go to sleep." And then sometimes she's, "I'm tired. Can you look?" Yeah, I'll do it. Don't worry." So the point is, the outcome was fixed. The outcome was our son gets comfort. And we were the, including the people, we were variable. Our process was variable. I would pick him up and walk. She would, sing to him.

Whatever, doesn't matter. We got the job done.

Jeffrey Feldberg: Yeah, my goodness. It's knowing what we want, but now let's connect the dots because... And again, I've been there myself. It's human nature. Most people not everyone, but most people want to avoid conflict. [00:28:00] And so many founders, "Yeah, Jeffrey, I really need to have or want to have this difficult conversation.

A team member isn't up to speed or they're not getting the results. My concern, though, is if I have that conversation, even though I own the business, even though I'm the founder, even though I'm ultimately responsible for everything, the buck stops with me, I feel uncomfortable about this conversation.

It's not gonna be a pleasant one. They may feel I'm undermining them. Even worse, they might even quit the company, and they are a superstar." So what have you found that's worked for yourself and perhaps even in your own operating system that you can share with Deep Wealth Nation when we see that results are off target?

I don't want to micromanage on the one hand. I don't want to be overly difficult on the other hand. At the same time, though, if I don't have that conversation, it's Einstein's definition of insanity, doing the [00:29:00] same thing every day, expecting different results. So what have been some strategies to approach this, particularly for a founder who, "Yeah I just, I don't want to lose a team member, and I don't want to create conflict."

How do we deal with that?

Rajesh Nagjee: So basically let's break this up into its various components. First and foremost, there is an upset sitting right there, that there's an expectation that you had. That expectation is not being met, whatever it is, in broad terms. So first and foremost, there's an upset. The second is, how do you communicate that upset and how do you have a conversation that there is a pivot, a required pivot that happens so that, you get into happier days.

So that's predominantly the structure of what you're presenting. So let's look at the upset first and foremost. So the first and foremost, for a founder to really get ready for that conversation, there's some homework that he needs to do, he or she needs to do. And that is sit down with a piece of paper [00:30:00] or on the board and write down just three words.

The word number one is expectation. The second is intention, and third is your feeling or communication. So what is the expectation that you have in that particular, you know, area or whatever it is that, that's creating an upset. So the upset is always a should statement. I should, they should, whatever, should.

It's always a should statement. That upset has got unfulfilled. That's the first strand. The second one is the intention. What was the intention for that particular thing to happen? Or the intention was that, our goods get dispatched on time, the customers get it on time, then everybody's happy and all the rest of it.

And the last is the communication is what is it, what do you feel? You feel short-changed, you feel angry, you feel frustrated. So once you write that down and really get really honest, now you've done your homework. So now you have the structure of the upset, because the moment you identify these [00:31:00] three very clearly, it's like the three laces in a shoe, that you open those laces out, your shoe comes off, the upset comes off.

So that's part one. Now, part two, when you're sitting to have that conversation, this is gonna be perhaps the toughest thing for you to do. But if you master this, you are home and dry. That is, have the conversation without a single should, must, and have to And if you can do that, you completely avoided the conflict zone because nobody can butt with you if you just avoid these three words should, must, and have to.

Because what are you trying to say the should, must, and have to? Is you're being right. When you be right, you're making them wrong. When you're making them wrong, suddenly this very fine human being has become a mule, and they just get stuck there in that position, and it's impossible to budge them, and they've got mule strength.

So because you made them wrong. That's not the purpose. The purpose is to [00:32:00] find a way to negotiate your way to get things done. So first, dismantle your upset on paper. No should, must, and have to. Three for one trade. Instead of should, must, and have to, use the word works. This doesn't work, or this will work better.

Try this. Maybe it will work better. Then you're opening up, possibilities for somebody to work with you and figure this stuff out because the law is very simple. Unless they perceive the gap, there is no shift or change that's gonna happen in adult behavior. The toughest thing to do is adult behavior change. Don't attempt it. You're gonna fail. I've tried it with my wife. My wife's tried it with me. I'm a damn good coach, but she's not succeeded, and I haven't succeeded at all. It doesn't work. It just doesn't work. So all you need to do is, present the gap in such a way. [00:33:00] Like she, tell me, "Put your shoes away.

I've got somebody visiting." You should do this. You must do that. It doesn't work. And then she'll say, darling, if you put the shoes away, it'll work so well. All of us will have a real pleasant time." Yeah I can hear that. I can get enrolled into that, and then I start moving it.

No should, must, and have to. Shoes. That's basically the anatomy. I've given it to you in short. Listen to this segment again and again, and break it up, make your notes, go to work, and you'll get the results

Jeffrey Feldberg: Yeah. What I love about that is this is so much, and you talk a lot about this in your work, it's an inner game, it's a mental game. Words make a difference. Believe it was Shakespeare, and if not Shakespeare the saying along the lines of the, the pen, the word is mightier than the sword. And to your point, to me, it's also underscoring the importance of KPIs, key performance indicators, and having plans and having goals.

"Hey [00:34:00] Jeffrey, together we set the KPI to be XYZ, and if I'm reading the dashboard right, we're 50% below XYZ. Any ideas what's going on?" Now, I may know the answer, but to your point, if I'm hearing you correctly, Jeffrey, you're on base, off base. I'm not saying, "Hey, it should be this. It's all your fault. What's going on here?"

I'm putting it out there, and if it's a good team leader, if it's an A player, they're probably thinking that themselves. Maybe they just haven't had the courage to talk about it. "Oh, yeah, he sees it, too. Now he's asking for my opinion. Okay, let me share what I think is going on," and we can have a discussion.

It's never about the person, it's about the performance or the behavior, but it's never personal, and it makes it so much easier to talk about. That's what I love about the KPI is it just takes the personal out of it and puts it to numbers or trends or, "Okay, what do we have to do? It's not you, it's not me, it's not I, it's what do we have to do to get there?"

And hey Jeffrey, [00:35:00] okay, you're sharing that, so what are your thoughts? How do you think we can get there? What does that look like? If you need some time, figure it out. If you're not sure, let's find someone that can support you, but would love to hear your thoughts." And it's collaborative, it's supportive, and we're getting to the root cause without these challenging, confrontational questions.

Now, if the team member is gonna be challenging on that, that's a whole other conversation. Maybe it's the wrong team member. But would love your thoughts on KPIs, data points, dashboards, and building that into our daily, weekly, monthly, quarterly, yearly goals.

Rajesh Nagjee: So, this is brilliant Jeffrey. Thank you for opening this whole thing up. Now, there's one problem with this, and the problem is, what is your affinity level with the person that you're talking to?

Jeffrey Feldberg: Mm-hmm

Rajesh Nagjee: So I've noticed that with varying affinity levels my tolerance of things that go wrong or things that don't match up or the KPIs get mixed I'm on [00:36:00] a very thin irritability line.

Jeffrey Feldberg: Sure

Rajesh Nagjee: with the result that all these things that I plan to do and, keep my cool and all the rest of it in the heat of the moment just my... the whole thermostat trips. So the question really is not about all of these things. Of course, these are very important from everything that you shared that gives you, a, a roadmap to be objective.

But I would say that first work on your affinity.

Jeffrey Feldberg: Mm-hmm

Rajesh Nagjee: And the way to do that is that if you make a list of thirty people that you interact with on your li- in your life on a more or less daily basis, then just write down what is your affinity level with the person. So affinity is the distance.

Like right now, Jeffrey, between you and me, our affinity is the highest level is serenity, right? I'm not feeling pressured, I'm not feeling put down. You're not sitting on a pedestal and making me feel like a worm or whatever. So there is serenity right there. And at the highest level of affinity there's a beautiful [00:37:00] conversation to be had every single time.

So I was in serenity with my dad, I was in serenity with, I'm with my wife, with my son, and so on. So now if you just do, traffic lights of green, orange, and red. With these thirty people, just do your traffic lights. With this person I'm in green affinity. With this person I'm in yellow.

This one I'm in red. Now, what is it that you need to do to move all these thirty people that you interact with to green, or at least to orange bordering green? Because the law is that every single person that you meet is a composite of those thirty. For example, Jeffrey reminds me of my brother and my cousin and a little bit about my aunt.

Now, it's it doesn't really matter. It's not male to male, but there is something about the way, your hair is, the way you talk, the way you smile, your energy. It reminds me of you because I'm all the time with these thirty people. Now, [00:38:00] s-see how much sense it makes. With all of those thirty people, if I'm already in green affinity, the moment I meet Jeffrey, who reminds me of this one and that one, I'm already starting out with a high affinity level.

And then all these other conversations you are able to negotiate because you're then a wealthy man. I'm an extremely wealthy man when it comes to affinity I'm in affinity level in s- in the green with almost every person that I meet. Why? Because every single time, like there's a waiter, he irritates me by by doing stupid four times.

But then in the end, I would get annoyed with him, and then I will say to him, "Hey, listen, buddy have a good life and, talk to your parents, and I really acknowledge your parents for the hard work they put in. And if I pained you, I'm sorry." I clean it up with him. I clean it up with him, and then I'll give him a tip because I don't want to carry the residue of [00:39:00] that guy's drop in affinity that I meet Jeffrey who reminds me of that manager somewhere who goofed up my reservation and I was so pissed off with him three years back.

And now Jeffrey looks exactly like that guy and prom without realizing I've tripped

Jeffrey Feldberg: Yeah. Yeah. Back to the mental game, the inner game. And I love the analogy that you give of the traffic lights, red, orange or yellow or green. And one of the things I encourage everyone in Deep Wealth Nation to do and when they're going through Deep Wealth Mastery, you and the team get some KPIs, get some goals, and assign to it what does a green light look like?

What does an orange light look like? What does a red light look like? And when we're having, it could be a daily huddle, it could be a weekly meeting, a quarterly meeting, I don't even need to ask the question because the whole team knows, okay, I'm meeting with Jeffrey I have an orange light right now. It was green last week.

This week it's orange or it's red, it's [00:40:00] got to green. If it's an A player, it gets me out of that uncomfortable situation. And even if they are an A player, "Hey, Bill, I'm really curious, what's going on? What do you think is going on? When we met about this last time, this was a green light, and I notice in the dashboard that you had shared with me the day before in preparation for today, it went from green to red.

Would love your insights on that." And again, it's not personal. It takes it right out of the personal into, okay, it's data points, it's insights. And it's not to say it's my gut reaction. The data points aren't adding up to this. Here's what I think is really going on." And that's fine too.

It just makes it non-confrontational, but it's productive. We can go from here to there, and it blends right in w- with what you're telling us. And the other thing I'm taking away, share a quick story with you. In our Deep Wealth 9-step roadmap, step six, advisory team. Now, the advisory team, it's our leadership team.

It's our frontline team [00:41:00] members. If we're raising capital, it could be an investor, it could be an investment banker. It's really all of our stakeholders. And when it comes to the advisory team, I could be meeting with the world's best advisor. Pick the area. It doesn't really matter. Whatever area it is.

And the question I love to ask is, Rexius, im- imagine you're now with this advisor. You're taking a business trip together. You're flying somewhere. You're on the tarmac. The plane is getting ready to take off, and it stops. And the pilot comes over the PA system, "Ladies and gentlemen, very sorry for this interruption.

We're having a mechanical problem. We're not able to go back to the gate. The airport's busy. A part is being flown in and unfortunately, we're gonna have to be on the tarmac here for the next eight hours." I'm over-exaggerating, but work with me on this. And so over that period of time, in the first five minutes, are you crawling out of your skin?

"I can't stand this person. They're driving me nuts. It reminds me of my great [00:42:00] aunt's second removed cousin this or that." Or the eight hours goes by and it just flew by. "Wow, I wouldn't have picked the eight hours, but I had an enjoyable time." And if it's one or the other, if it's, "Yeah, I'm crawling out of my skin," it may be the world's best advisor, but probably not for you because chemistry to what you're alluding to, what you're pointing out, it's everything.

And so maybe they're the world's best advisor, just not for me. Let me find an advisor who's also terrific, but those eight hours just flew by. Wow, where did the time go? Would love your thoughts on that.

Rajesh Nagjee: Jeffrey, do you know my hair's standing up as you're speaking? Because I was actually stuck on the tarmac for eight and a half hours This was many years back. It was a British Airways flight and we were stuck in London, and I was flying from Bombay to London to somewhere in the US. And two things happened.

There was a, a very tall and a very strong lady sitting right next to [00:43:00] me.

Very pleasant. So we had a fantastic conversation. In fact, I got invited to go up to a commune, and my son and I, we went there and met her husband, so that's another side story. But I'll tell you what happened then I'll come back to your question.

So the British Airways, what they did is they got a, a person who was superb on the mic, and he kept telling us and giving us a running commentary on where this part was being flown in from, and there's a special engineer. There are only three engineers in the UK who could do that. One has gone away overseas for a holiday, one has gone to the south of England to meet his parents, and the other guy has gone fishing in his village.

So they dispatched a car and they went to find him in his village. He wasn't here, he wasn't there. So every 15 minutes we're getting the bulletin of what's happened to this part, what's happening here, and he kept us enthralled as if it was like a game.

Jeffrey Feldberg: Mm-hmm

Rajesh Nagjee: the end of it, I will tell you, [00:44:00] I will fly British Airways again and again because of the fabulous way in which they treated that, and then I had this wonderful conversation.

So now to your point, if I'm sitting next to somebody who's who's brilliant and his brilliance is not working for me, obviously the affinity levels are not matching, the chemistry is not matching. And if that's the case that brilliance doesn't... You're not allowing that brilliance to transmit and to come to you because there's some resistance inside you, right?

And it's happened many times with me especially, now that I'm a, a very experienced coach. I sit next to people and most of the time I don't wear all my arrogance and ego on my sleeves. I'm easygoing and all the rest of it. But sometimes the buttons get pressed, right?

And when they're pressed , this guy can be fantastic. But then I take a deep breath, calm down, and then I say something to disarm the person or to me [00:45:00] so that we can then have a pleasant conversation.

Jeffrey Feldberg: Mm-hmm

Rajesh Nagjee: And then there is another thing that came up for me many years back, and I found that I used to attend a lot of seminars and a lot of workshops, and then I would come, at the end they give you that sheet to rate that whole show and all the rest of it or the whole-- the program your feedback form, and I would always be very honest and, I'd give marks what I thought were absolutely okay.

And in the end, the average would turn out anywhere between six to eight or nine, sometimes ten. Then I realized that my search was for the perfect teacher, and the perfect teacher doesn't exist. I reconstituted myself to be the perfect student. And from that day onwards, this is now almost twenty years, that every single workshop I go to, every single seminar I attend, I first get that feedback form.

They don't have it, I put it in my book. I give that program ten on ten before the person has started [00:46:00] speaking. And after giving it ten on ten, now I'm telling you as a perfect student, I will get that value because I'm open, I'm available, and all my judgment is off. Who made me the judge?

You come here to attend a seminar. You come here to attend. The person is speaking. There is something about him you don't like. Now you're stuck there instead of what he's actually worked on, he's bringing to you. So if you're not able to receive, if your channel is blocked, then you got all these issues and you can whine.

I realize I'm the world's biggest whiner. I kept whining about everything, and so, so these are the things, if you embrace this, life becomes fun

Jeffrey Feldberg: I love how you're making a game out of it. Use the F word. We're having some fun along the way. That's really what it's all about. Now let me ask you this, Rajesh, before we go into wrap up mode. There are so many things we haven't yet covered. You are a wealth of information, and by the way, Deep Wealth Nation, I'll mention this again, go to the show notes.

Everything is there in [00:47:00] terms of the resources and what we haven't spoken about, and I'll talk about that again. But Rajesh, back to you for just a moment. Before a listener in Deep Wealth Nation, they're listening to us right now, we're having a nice fireside chat. Before they go into the next activity, maybe it's a meeting, it's a phone call, whatever it's going to be, if they could just do one thing, one thing only, one strategy that could really move the dial.

Bit of an unfair question because you've created so many terrific strategies. But if you had to pick one low-hanging fruit, maybe it goes back to the 80/20 principle that predates a lot. Yeah, Jeffrey, you know what? 95% of founders, when they do this one thing, it really can not only make their day, it may even make their year.

What would be one thing that someone in Deep Wealth Nation can give it a try, an experiment that could really make a difference before they go on to the next thing? They could take this one action. What would that be? What do you think?

Rajesh Nagjee: So can I restate what I heard you say?

Jeffrey Feldberg: Absolutely

Rajesh Nagjee: Okay, so what you're asking [00:48:00] me is that for everybody who's listening in, what is the one thing that they can do that would really give them some sort of insight or some value or some opening? I paraphrased it, but is that the essence of what you just said, or is there anything you want to add to that?

Jeffrey Feldberg: Deep Wealth Nation, while we're going through this, I love what Rajesh just said. Hey, Jeffrey, let me make sure I'm hearing you properly. Is this what you're saying? And if we're not asking the right questions, as I like to say, the only silly question is the one that never gets asked, and that was not a silly question.

But absolutely, yes, you're spot on with how you asked the question. Absolutely.

Rajesh Nagjee: And that's, I just demonstrated the answer to your question. If you can do this, just say back to people by saying, "Hey, listen, can I say back to you to make sure I got it right?" Now two things happen. The person that you say back to feels very good. They're, "Okay, now he's asking me, he's checking in with me."

And they- they're not gonna get pissed off. They're gonna say yeah, this is fine, this is a little bit you left out." [00:49:00] The second thing is you're demonstrating listening, and the biggest thing is you're giving that person the gift of being heard

Jeffrey Feldberg: Mm-hmm. Yeah. Yeah

Rajesh Nagjee: And the moment you start giving people the gift of being heard, you become rare.

Because the bottom line is nobody's listening. They're just waiting for their turn to speak. Like Jeffrey started asking me this question, I'm waiting, okay, I got the question that he wants to say. I'll talk about this, I'll talk about... I'm waiting for Jeffrey to finish what he's saying. No, he's still talking.

Okay, I'm nodding. I want to say this one thing, brilliant thing. I've got this fantastic idea, I want to share it with people, and I'm going to impress everybody. It's gone. So instead of that, I said, "Okay, hold on a second. Just switch off.

Jeffrey Feldberg: Ja

Rajesh Nagjee: Just relax. And Jeffrey's speaking, and he's making this wonderful, request that will serve so many people.

Just be with it." And as I was being with it, I said, " Can I say that back to you?" And you [00:50:00] said, "Yes." And then you also said, "Hey, this is a great thing to all your people, the way you said it." That is, I- the biggest area of breakthrough for people, especially for founders and CEOs

Jeffrey Feldberg: I absolutely love that because it also goes into human nature. We all want to feel heard. We all want to be seen, and when we can ask that question, just like you did, and it was curious, "And am I understanding this?" "Hey, yeah. Okay." Rajesh, he's right there with me. He's actually listening, and it takes the conversation to a whole new level.

So Deep Wealth Nation, pay attention. Some terrific insights there. And actually, it's a great segue as we go into wrap-up mode because it's our tradition here on the Deep Wealth Podcast. This is my privilege and honor, every guest I ask the same question. It's a fun question. Let me set this up for you.

When you think of the movie Back to the Future, you have that magical DeLorean car that will take you to any point in time. So imagine [00:51:00] now it's tomorrow morning, and Rajesh you look outside your window, and this is the fun part. Not only is the DeLorean car curbside, the door is open, it's waiting for you to hop on in, which you do.

You now go to any point in time. Rajesh, as a young child, a teenager, whatever point in time it's going to be, what are you telling your younger self in terms of life lessons or life wisdom? Or, "Hey, Rajesh, do this, but don't do that." What would it sound like?

Rajesh Nagjee: I wanna go back to the first time I heard my father say this, and he said that over and over through my entire life. But what I'm missing is the first time he ever said that, because obviously I can't remember it. And that, what he said to me is, " The day you decide, you will do it."

Jeffrey Feldberg: Love that

Rajesh Nagjee: And I, it took me 55 years to decode that.

Jeffrey Feldberg: Aha

Rajesh Nagjee: And what I realized is that he had Teflon-coated me against failure.

Jeffrey Feldberg: Mm-hmm

Rajesh Nagjee: Every time I failed, father's statement [00:52:00] kept coming back to me, "Hey, you haven't decided." So it's not about the outcome, but it's about my decision. So now I decide, now I'm gonna go after it, and then the ultimate success formula is don't stop till you succeed

Jeffrey Feldberg: Absolutely

love that 

Rajesh Nagjee: I would love to when I was three years, four years, five years, six years, my father saying that for the first time in his voice, he passed away in '89.

That's what would, I would really like my life up

Jeffrey Feldberg: Yeah. What a terrific insight. The day you'll decide you'll do it, and then what do you really want? Okay, I'm gonna do it, but what is doing it? What do I want? Really two terrific questions. You gave us a bonus there. You went above and beyond. You went the extra mile with that. And let me ask you this, someone in the Deep Wealth Nation, they're hearing us talk, and they wanna speak with you.

Maybe they wanna have the one-on-one with you or some group coaching, or I know you do retreats with business groups or even your Brilliant Strategy workshop. Where would be the best place online for someone to reach [00:53:00] you?

Rajesh Nagjee: Follow me on LinkedIn write to me direct message or my email is rajesh [at] nagjee [dot] com. That's it, and I'll respond. I-- so purpose of my life is make friends, have fun, be playful, and make memories. So I was leading a Forum Fundamentals workshop last week on the 18th, and out of the nine people who attended, three of them want to meet with me to see how I can work with them, and it's such a pleasure.

And then, it's not everybody who I meet the chemistry works or the timing works or, something or doesn't work, but we can always be friends

Jeffrey Feldberg: Love that. And Deep Wealth Nation, it does not get any easier. Go to the show notes. It's all point-and-click. All the resources are there. And that said, Rajesh, congratulations. It's official. This is a wrap, as we love to say here at Deep Wealth. May you continue to thrive and prosper while you remain healthy and safe.

Thank you so much.

Rajesh Nagjee: Thank you. Thank you, Jeffrey. It's a [00:54:00] brilliant conversation 

Jeffrey Feldberg: So there you have it, Deep Wealth Nation. 

What did you think? 

So with all that said and as we wrap it up, I have another question for you.

Actually, it's more of a personal favor. 

Did you find this episode helpful? 

Have you found other episodes of the Deep Wealth Podcast empowering and a game changer for your journey? 

And if you said yes, and I really hope you did, I have a small but really meaningful way that you can actually help us out and keep these episodes coming to you.

Are you ready for it? 

The dramatic pause. I'll just wait a moment. Drumroll, please. Subscribe. Please subscribe to the Deep Wealth podcast on your favorite podcast channel. When you subscribe to the Deep Wealth Podcast, you're saving yourself time. Every episode automatically comes to you, and I want you to know that we meticulously craft Every one of our episodes to have impactful strategies, stories, expert insights that are designed to help you grow your profits, increase the value of your business, and yes, even optimize your post exit life and your life right now, whatever you want that to look like.

And every time you subscribe and a fellow entrepreneur [00:55:00] subscribe, it's a testament to how together, Yes, we are. We are changing the social fabric of society. One business owner at a time, one liquidity event at a time. So don't let the momentum stop here. Subscribe now on your favorite podcast channel.

You'll never miss an episode. You'll be the first to hear from the top industry leaders, the innovators, the disruptors that are really changing and shaping the business world, and maybe you're commuting, maybe you're at the gym, maybe you're taking a well deserved break that we spoke all about on this episode.

The Deep Wealth Podcast, it's your reliable source for the next big idea that could literally revolutionize your business. So once again, please hit that subscribe button, stay connected, inspired, and ahead of the curve. And again, your next big breakthrough moment, it might just be one episode away. Maybe it was even this episode.

So all that said. Thank you so much for listening. And remember your wealth isn't just about the money in the bank. It's about the depth of your journey and the impact that you're creating. So let's continue this journey together. And from the bottom of my heart, thank you so much for listening to this [00:56:00] episode.

And as we love to say here at Deep Wealth, may you continue to thrive and prosper while you remain healthy and safe. 

Thank you so much. 

God bless.


Rajesh Nagjee Profile Photo

CEO Mentor | Business Physicist | Creator of CEO Freedom OS™

What happens when a business becomes successful enough to give you everything you thought you wanted, but dependent enough to take away your freedom?

Rajesh Nagjee knows that tension personally. He built his first seven-figure business and nearly burned out in the process, eventually realizing that he hadn't created freedom. He had created dependency. Every decision came back to him, strategic work was constantly delayed, and even time away from the business came with interruptions. That realization became the foundation for what he now calls CEO Freedom OS™.

Over more than three decades, Rajesh has built and scaled businesses, transitioned a 95-year-old family company into a professionally run operation, founded and led a trauma-care hospital in rural India, earned a Sloan MBA from London Business School, and co-founded businesses in Dubai that have delivered more than 1,000 projects. He has also trained more than 40,000 executives and facilitated 150+ YPO and CEO forums globally.

Today, he mentors scale-stage CEOs on something many entrepreneurs discover too late: the business is only truly successful when it can succeed without consuming its founder.

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