Jocko Podcast

Jocko Underground: Making The Mental Shift Upward

12 min
Feb 23, 2026about 2 months ago
Listen to Episode
Summary

Jocko Willink advises a solo entrepreneur transitioning to building a team-based business on the mental and practical shifts required for leadership. The discussion emphasizes that people management is the biggest business challenge and reward, requiring intentional learning of leadership principles rather than instinct.

Insights
  • Leadership is not instinctual and must be deliberately learned through study and contextual application, not abstract theory
  • Scaling a business requires gradual team growth (2-3 people at a time) to allow time for leadership skill development
  • Vision and mission clarity are foundational prerequisites before hiring; employees need to understand where the company is headed
  • Leadership principles must be extracted from books and frameworks and actively applied to real-world business situations daily
  • Goal-setting and reverse engineering from desired outcomes enables better decision-making than reactive day-to-day operations
Trends
Solo entrepreneurs recognizing scalability limits and transitioning to team-based business modelsDemand for practical leadership education among first-generation business builders from working-class backgroundsEmphasis on intentional leadership development as competitive advantage in growing businessesShift from abstract business principles to contextual, situational application frameworksGrowing interest in direct-to-consumer subscription models to reduce platform dependency (Jocko Underground model)
Companies
Echelon Front
Leadership training and consulting firm offering online academy and courses for business leaders and entrepreneurs
People
Jocko Willink
Host providing leadership guidance and recommending his books on extreme ownership and leadership strategy to the que...
Echo Charles
Co-host discussing leadership principles and reinforcing key concepts about goal-setting and strategic planning
Quotes
"The most challenging thing about a business, it's not the market, it's not the product, it's not the supply chain, it's not the regulations, it's not the science, it's not the financing. Nope, it's the people."
Jocko Willink
"Leadership is counterintuitive, right? So you have to kind of constantly force yourself back on track."
Jocko Willink
"You got to take it out of the abstract and out of the theoretical. It's a book. You got to drag it out of there and you got to put it into the situation that you're in."
Jocko Willink
"You always have to ask them what are your goals for this thing because it depends on what their goals are, what are we trying to do?"
Echo Charles
"Gotta look up, gotta have a plan. You gotta know where you're going."
Echo Charles
Full Transcript
This is the Jocko Underground podcast number 202. Sitting here with Echo Charles, you have sent questions and we have possibly answers, possible recommendations, at a minimum, courses of action that you can follow to proceed forward. Courses of action. It's true. All right. First question. Good morning, Jocko Echo. My name is Max, and I'm reaching out for guidance on both mindset and practical business growth. I dropped out of college 2022 to pursue an online business I started. It has allowed me to support my family and purchase two houses, but I realized it isn't scalable beyond its current level. Over the past year, I started a junk removal and foreclosure clean-out business, which has now replaced my income and presents far greater growth potential. What I find challenging is the mental shift from operating as one man business to building and leading a real company with employees. I've only ever been surrounded by middle and working class environments. I understand how to work extremely hard and push forward, but scaling into something larger is unfamiliar territory. How can I strengthen my mindset to take that next step? From a practical standpoint, what advice would you give someone transitioning from solo operator to building a team? Thank you for your time. Yeah, right on, man. Well, first of all, congratulations. It sounds like you're making things happen, which is kind of awesome. And you have the foresight to recognize that the most challenging thing about a business, it's not the market, it's not the product, it's not the supply chain, it's not the regulations, it's not the science, it's not the financing. Nope, it's the people. People are always the biggest challenge. And of course, that's why it pays the biggest reward. And it's how we accomplish great things is through leadership. But it's good that you're recognizing the situation that you're going into. And one nice thing here is you, this is not gonna happen overnight. In other words, you're not hiring 100 people into your team tomorrow. You're gonna hire two or three and then you're going to get four or five and then you're going to get eight and you're going to have 10 and 12 and then 15 and that's how you're going to grow. So it's going to grow and it's going to give you some time to learn to lead. And listen, I don't know any other way to say this. I would start off immediately by getting the book Leadership Strategy and Tactics Field Manual and I would immediately open up to a page 157, 158. I would read those and then I would go read that whole book. And then I would use that book as a reference. I would then read the book Extreme Ownership and then I would read the book the dichotomy of leadership and Listen you're asking the questions about leadership and the answers are What we wrote the books about Right This is why we wrote those books They are filled with the answers to your questions So you know read those books And then what I think is the part that can help you that I can give you right now is you have to take the context that you're in and overlay the principles of what you read so that you understand how they impact. A lot of times people think of it too abstractly. Like, oh, extreme ownership is a principle that I read about. But they never say, wait a second, the situation that I'm in right now, how do I apply cover and move in this situation right now? How do I apply building relationships in this situation that I'm in right now? So you got to take it out of the abstract and out of the theoretical. It's a book. You got to drag it out of there and you got to put it into the situation that you're in. And you need to do that on like an almost like a twice a day, like once in the morning, once at lunch, maybe three times a day. You look at the end of the day and do a review and see how these things fit in there because it's not natural. Leadership is counterintuitive, right? So you have to kind of constantly force yourself back on track. And then, you know, so do that. Obviously, listen to the podcast. Listen to the debrief podcast. Good things on there. Listen to this podcast. Obviously, you already are. you know join the echelon front online academy extremeownership.com like that's we have people all the time that are on there we're ask answering questions giving feedback to there's a bunch of courses on there to take again all this will help you build this framework that then you can put the context of your world into so those are like like this is a giant question you know hey well what What advice do you have for leadership? Bro, it's a big deal. It's a big deal. It's not instinctual. It's not easy. You're not born of it. You actually have to learn it. You actually have to learn it. If someone said, hey, Jocko, this question, if it said, hey, Jocko, I've got to write a report on the Civil War. What can you tell me about the Civil War? You know what I mean? Like that's a huge question. That's a huge question. Or like, hey Jocko, I just got a guitar. What should I do? Yep, you should get a book about how to play guitar. That's the one that's a little bit different because that guitar is a... But you're gonna need to learn how to tune the guitar. You're gonna learn how to know what the chords are. Like there's things you're gonna have to do because it's a big subject. And leadership is a bigger subject than either of those. Bigger subject than the Civil War, bigger subject than playing guitar. So get those books. And then those things will be helpful. And just to get you started here, what's the vision that you're looking for? Make sure that people understand what the mission is. Make sure you know what the mission is Make sure you know what it is you trying to do And then you know when you hire people build relationships with them And you heard me say it on here trust, listen, respect, influence, and care. That's what we're doing. And you build a good relationship with people and you're gonna build a solid team and you take care of them and they're gonna take care of you and things are gonna be good to go. So that's where we're at, man. Just know those principles and then force yourself to apply them into the world that you're living in. That's what we got. You said something that was actually more important than I feel like a lot of us realize. And that is like, where do you want to go? Like what's the, so back when I was a personal trainer, through certification, they tell you like, this is a very important element of being a trainer. When someone's like, hey, I want to get in shape. I need a personal trainer. Or is this a good exercise? or whatever you know any question that someone asks a potential client or client asks you it supplies to this you always have to ask them what are your goals for this thing because they're yeah you still do that i mean anybody sends some anytime someone's talking about working out you're always like well what depends what their goals are what are we trying to do exactly right um and it it's and it's not just having it's like it's absolutely true just like this where it's like like hey what advice do you have it's like oh well depends bro you know totally depends um so a identifying where you where you want to go and you know being conscious of where you are now and then kind of reverse engineering it kind of a thing and then yes using all the all the strategies and tactics for sure but because a lot of times bro even in just everyday life sometimes we can forget these things so like when you're like um hey where do i want to be like bro when i was young you know how people ask you like where do you want to be in five years i was like bro i don't think i ever thought about that five five years that's a long time from now like i don't think about that kind of stuff i'm thinking about today or 10 let alone 10 years so but if you kind of like hey just take a minute and be like bro where do you want to be in however long it'll be five years or whatever it's like oh shit that kind of turns on some light bulbs there see what i'm saying that's like okay and then you know you can get little uh tactics which one that i heard that i was like oh that's a useful just little thing to ask yourself it's like hey where do you what do you have to get done today for it to be what they call you know a win or what do you have to do today to make it a successful day it's kind of like that like we don't like i don't think about that kind of stuff back before like a long time ago i just think about okay i got something to do and i'm too busy quote unquote doing it rather than like stopping and be like okay where do you want to be and kind of mapping it out, you see what I'm saying? Then you can start to make appropriate decisions. Otherwise you just with your head down going through freaking, you see what I'm saying? Gotta look up, gotta have a plan. You gotta know where you're going. And then that iterative steps thing, and you mentioned it where it's like, don't hire 100 people. Just be like hey if I know where we wanna be next week and I can see the discrepancy between where I am now and where I wanna be I can be like okay I I can do this this this That it though See what I saying And then we reevaluate next week See what I saying You ever get asked like, hey, if you could learn one thing as a white belt, what would the one thing be? You know, I get those kind of questions. Going into SEAL training, what's the one thing you would like? People are always looking for a kind of a shortcut or kind of that distilled like thing. and really it's very it's very difficult to answer that question properly because Who am I talking to because if you're a dude that Habitually over trains and like goes overboard and gets hurt and you come to me and I don't know you and you say hey You know, I'm just starting jujitsu. What what's the one thing that I should do? And I'm like make sure you make sure you train as much as you can and you go cool got it And you train for two months and you're injured. Yeah, you know Like I don't like it that much or you know, hey, what's the one thing you should do to get ready for seal training? Well, if you're a crappy runner, you should run if you're a crappy swimmer You should swim if you're a great runner and I'm like, you know what? The most important thing is running and you go cool and you run more but you forgot to do pull-ups You see what I'm saying? So it's like with this leadership questions like well, you know what's the most important guidance when I start a new business? Well, it depends on who you are. Maybe you're a type of person that builds great relationships with people. Cool. And I tell you, hey, relationships are the most important. But then you get buddy-buddy with everyone, and there's no lines, and no one knows who's in charge, and you don't have any plans. So really, that's why I can't give this just kind of simple, hey, even the thing that you just said, like, hey, you've got to make sure you come up with a plan. Because there's some people that have already been planning. Oh, so that is a little excerpt of what we are doing on the Jocko underground podcast. So if you want to continue to listen, go to Jocko underground.com and subscribe. And we're doing this, we're doing this to mitigate our reliance on external platforms. So we are not subject to their control. And we are doing this so that we can support the Jocko podcast, which will remain as is free for all as long as we can keep it that way. But we but we are doing this so we don't have to be under the control of sponsors. And we're doing it so we can give you more control, more interaction, more direct connections, better communications with us. And to do that, we're building a website right now where we'll be able to utilize to strengthen this legion of troopers that are in the game with us. So thank you. It's JockoUnderground.com. It costs $8.18 a month. And if you can't afford to support us, we can still support you. Just email assistance at JockoUnderground.com and we'll get you taken care of. Until then, we will see you mobilized underground.