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Host
HubSpot is a success story, partner. Now think about listening to this podcast. Right now you are probably multitasking. You are probably catching maybe 70 to 80% of what I'm saying. Now flip that and imagine catching only 20%. It's not a good use of your time. That'd be insane, right? But this is the reality for most businesses. Most businesses only use 20% of their data. That's like reading a book with 80% of the pages torn out. You are making decisions with a fraction of the picture. All the important details that get buried in the call logs and the emails and the transcripts and the chat messages, and it's just floating around doing nothing for you. Unless you use HubSpot. Their customer platform brings all that unstructured data together and turns it into insights that actually help you grow your business. Because when you know more, you grow more. And when you're running a business on a hundred percent of your data instead of 20, the decisions get a lot easier. Visit HubSpot.com to get the full picture today. In this lessons episode, explore why chasing external success leads to emptiness and how real fulfillment comes from purpose driven work. Discover how mastery attracts wealth and recognition. Understand the difference between achieving goals and dedicating a life to meaning. And uncover why helping others succeed creates deeper satisfaction.
Guest 1
This is something that's interesting. I want to just ask something on this before we move on. So a lot of people, they look at the second mountain and they're always striving, striving, striving. But I feel like they're looking at it for the wrong reasons and. Let me, let me explain. So when you do achieve a level of excellence in almost anything, any field, and you have the impact that you
Host
were, I believe, put on earth to
Guest 1
have, you will coincidentally just have all those things anyways. If you are the best at teaching, if you are the best at building a business, you are the best at motivating. If you are the best athlete, if you're the best author, the best poet, the best. Right, whatever. If you are the best of the best of the best, you get all the stuff. But I feel like people want the stuff and they don't actually end up understanding that they have to be the best. Whereas if you just had the mission of being in the, the top percentile of that field, all the other stuff comes naturally anyway. Like look at yourself, for example. You're building up your brand, you're speaking on global stages. All that comes with money. All that comes with notoriety and fame and wealth. But it's like you've positioned it in a different way. So you're doing the thing that you're passionate about and you're not just chasing it for the money, you're chasing the thing for the thing. And then the money is like a secondary result.
Guest 2
I'll show you the second mountain. Second mountain is different.
Guest 1
I want to understand this more because. So the reason why I'm trying to understand this is because I agree with
Guest 2
you, though I'm not. I'm not disagreeing on people. Everyone wants to be famous, but no one wants to do the work. Quote Kevin Hart. Yeah, I agree with you and the concept of people being obsessed with the fame, the money, the cars, the house, the girl, the guy, the. The trips, the travel, the jet, the house, the whatever, the stuff. That part for me was no longer interesting. And it's not because I got it all. It's because I found something that was worth investing my life into, which I think is what you're hinting towards. But finding something that's worth investing your life into is very different than finding something you can go achieve, because it's not about achieving, it's about literally dedicating your life to it and saying, ah. If I walk this path for the rest of my life, I will be eternally joyful, regardless of how many steps I take down that path. I just know I'm on the path and that is the joy. And then it's like, well, what path? And when I came back, and I'll just give you, this is ridiculous. At least in my mind, looking at it now, I came back, I was pissed at homeless people. Like, you're standing in the richest country on earth. You have access to clean drinking water that won't kill you. You have access to food. You have shelters, you have community service. You have shelters that'll help you get a job. And you're standing out here doing nothing and complaining. Like, I was pissed at homeless people. I went back to a private Catholic college, you know, in San Diego. I sat at the little cafe working on my homework, and I heard girls, guys talking about TV shows and ugg boots and. And I was like, you guys are idiots. Like, you really are obsessed with nonsense. And I was wildly judgmental and I was just kind of frustrated and pissy at humans for a while, which also
Guest 1
wasn't good either
Guest 2
anything or anyone. So that was the wakeup. I sat one time, I'm like, how am I helping anything by just being pissed at people? And I was like, okay, how could I help? What Could I do? And I was like, I need to wake them up to go care about more than just themselves. And I don't know if you've ever tried to go tell young people that there's more to life. Like, they look at you like you have three heads and they don't care. They're like, that's great. Cool. I'm gonna go get my car now. Like, they don't care. I was like, God, that's annoying. And I said, you know what? I'm gonna do the workaround. I'm gonna figure out how to get them to the peak of that mountain faster so that they can realize it ain't it. Jim Carrey says, I wish everyone could be rich and famous and have all their wildest dreams come true so they could realize it ain't it. I was like, you know what? I'm gonna make people's dreams come true faster. I'm going to get their ass to the top, I'm going to put them on rocket fuel and get them to the top of that mountain as fast as I possibly can. And then stare them in the face and go, now what? And let them go. That mountain. Boom, we're there. Now what? That mountain. Boom. There. Now what? And I did it. I remember I took a young guy in New Jersey. Him and I were talking, he had done finance at nyu and he was living at his parents house at the time. And he was like, if I could just work hard enough and move to the city and have my own place in New York City, then I would be really living six months later. Had, you know, got a job, made the money, moved to New York City, has his own pad in New York City. I'm like, now what? He's like, you know, having a place in New York City is cool, but I gotta be able to travel. I gotta be able, like go places. Like that's the real juice in life. Got him a job as a corporate speaker. Traveling around the country every three months. Different city, corporate apartment, corporate car, corporate phone, everything handled. And he's like, yeah, after, you know, a few years of doing that, he's like, this is great, but I really feel like I need a home base now. Like somewhere that I would just love to come home to. Fast forward, moved around a little bit, eventually landed up living like 500 yards from our house here in Puerto Rico on the beach. He had a beachfront condo, 180, Ocean View on the ocean. And he's like, you know, now if I could just. And I looked at him, I'M like what makes you think the next thing is going to be any different than the last four? You've gotten everything you've wanted every time you wanted it, but nothing's really changing. And he's like, I know bro, I know. Like, then what is it? What is it? What? What would allow you to finally find something that you could invest your life into, something that you'd be so passionate about that you. Like you said, the money doesn't matter, the time of day doesn't matter. It's kind of like you fall in love with life. Time disappears, you disappear. Nothing else matters. You're just obsessed.
Guest 1
You have like flow, flow state in life at this point because everything is in the zone.
Host
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Guest 2
Just there. I'm like, what is that for you? What is that? And he's like, I don't know, bro, maybe it's this or maybe it's that or maybe it's this. And we dug in and for him it turned out it was. It was working with people in a coaching capacity. It was like helping other people like you helped me. And I was like, you think that's it? He's like, I know that's it. He's like, that's when I feel alive. Like, cool, cool, cool, cool. And he's like, truly, dude. Like, he always teased me, like, I don't know if you remember, you changed my life. Like, remember the kid who lived with his parents in New Jersey? That's me. And I always joke, like, now he travels all the world and speaks places. He speaks places and he coaches people and does all this stuff. And at one point, like you said, those were my dreams. I don't have a deep yearning for that stuff anymore. I remember I spoke at a Stadium to 15,000 people in Germany, 2019.
Guest 1
I watched that whole thing. That was amazing.
Guest 2
Your perfect day. It checked the box. It checked like a soul level box. For me, some part of myself was still wanting to compete with my dad. Filling stadiums of people to talk to after I got to go speak to an entire stadium. It checked the box of like, I'm good, I don't need to speak anymore. I've said enough. If they want me to, I'm happy to. But there's no part of me that feels like I've got to be the one talking. Like, yeah, let them talk. Let me send some of my people I've trained. Let them go talk Let them have the experience. And that's part of the second mountain. The first mountain is can you make it to the top yourself? But after you've been to the top a few times, it's not. I mean, it's cool, it's fun to get there. You high five yourself and you're proud of yourself for the moment. But the real magic comes when you bring someone else up and you watch them experience what it's like to get there the first time. And so that, that's kind of a different stage of life for me even. We were just in South Africa. I've been on safari four or five times in my life. It's a blessing. It's life changing. For me, it was. And it's life changing for most people. I took my wife and son, who's only three, on a safari for his birthday when he turned three a few months ago and. Or just last month actually. And my wife came back from the, you know, two days and, and 10 hours we spent driving around looking at all the animals. And she's like, I think that safari changed my life. And I smiled and I was like, she's like, what was your favorite part? I was like, your face. Watching you experience it for the first time, that was the coolest part. Like, I've. I love the animals. They're amazing. I love seeing the animals every time. They still wow me every time. But watching her face see it for the first time and watching my son see it for the first time was the coolest. And so those are things that I look for now. Can we create an experience that allows someone to experience a part of their life they've never experienced before? Can we help them reach a peak that to them we get to watch their face, have that peak moment and peak experience in their life? And I get to be proud saying, hey, I was a guide. I remember I was working with a client and at one point his father had exited his position in the major company. And this guy was in his 60s and checked every box you could imagine. Had the jet, the helicopter, the multiple houses, the government level, whatever. Like he had everything. And he's like, I'm worried about my dad. Now that he's retired, he just sits and plays crossword puzzles all day and talks about the will. I was like, oh. And he's like, can you talk to him? I was like, I don't know if he's going to listen to me. Like, I'm young, I'm still putting my together. He's kind of at the other side of the journey. He's like, I know, but you have some magic can, like, you say something to him. I was like, I'll talk with him if he wants to. It's totally up to him. And he was super kind and generous. He's like, oh, thank you for your time. You're so kind. All this stuff. He was very nice. And at the end of the conversation, he was so thankful. He's like, thank you for the work you've done with my son. You changed his life. He's like, thanks to the family, he has enough money. He'll never have to worry about money in his life. But I was worried about him as a person, if he would build a life he'd actually be proud of. And he's like, after the work he's done with you, he's building a life I know he'll be proud of.
Podcast Outro
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Episode: Lessons - Why the Highest Paid People Never Chased the Paycheck
Host: Scott D. Clary
Guest: Jairek Robbins (Performance Coach & Bestselling Author)
Date: April 20, 2026
In this lessons episode, Scott D. Clary and Jairek Robbins dive deep into the difference between chasing external markers of success (money, fame, status) and finding real, lasting fulfillment through purpose-driven work. They explore the concepts of mastery, the “second mountain” of achievement, and how true satisfaction often arrives from helping others achieve their dreams, not from accumulating accolades or wealth. Through candid stories and personal reflections, they unpack what it means to dedicate one’s life to meaningful work that brings both joy and success as by-products—rather than primary objectives.
Difference between Achievement and Fulfillment ([02:42]-[04:50])
Awakening Beyond Material Goals ([03:50]-[04:50])
Moving Beyond Personal Achievement ([10:19]-[13:44])
The Joy of Guiding Others ([13:00]-[14:47])
The conversation is candid, warm, and introspective, filled with storytelling and honest reflections about money, mastery, and what really matters. Both Scott and Jairek speak with a tone of curiosity—questioning not only their own motives but those that society at large holds up as markers of “success.”
This episode’s central lesson: The highest-paid, most recognized people rarely started by chasing paychecks or accolades, but by seeking mastery and pouring themselves into meaningful work. True fulfillment, and often wealth, naturally follows dedication to purpose—and the joy multiplies when you help others reach their own mountaintop.