Jesse Krieger: ALL IN with Lifestyle Leadership

Wish you could be working from the beach? Lifestyle entrepreneur Jesse Krieger shares how he created a business and a lifestyle that lets him travel the world, create multiple successful business and still find the time to party in Vegas in the latest installment of ALL IN.
Jesse Krieger was born and raised in San Francisco but spends three to four months a year traveling the world. Whether it’s climbing volcanoes with friends in the Mediterranean or consulting with clients from Malaysia to Manhattan, Jesse views the world as both a playground and a potential addressable market. During his twenties Jesse started over five companies and sold the last two. He is the author of Lifestyle Entrepreneur: Live Your Dreams, Ignite Your Passions and Run Your Business From Anywhere in The World.

Jesse K intro photo

In this episode, you will learn:

  • Why you can do what you love and make money
  • Why leaders need to be a source for their followers
  • How pushing personal boundaries makes a good leader
  • How humility saves the day
  • Why your business should fit around your priorities
  • How to focus on the important tasks

Keep Going ALL IN:

Jesse’s favorite leadership quotes:

[inlinetweet prefix=”” tweeter=”” suffix=””]”Lead me, follow me, or get out of my way.” – George Patton #ALLIN[/inlinetweet]

[inlinetweet prefix=”” tweeter=”” suffix=””]”You only have to be right once.” – Mark Cuban #ALLIN[/inlinetweet]

Interview Transcript:

Interview with Jesse Krieger
Alicia Dunams: Hey, it’s Alicia Dunams here with ALL IN: Elevating Your Leadership Game. I am interviewing Jesse Krieger. Hi Jesse, how you doin’?
Jesse Krieger: Hey Alicia, I’m doing great. Very excited to be here.
A: Awesome. So, I love to ask this question as we get started. Are you ready to play ALL IN with me today?
J: Alicia, I am ready to play ALL IN with you today, and every day.
A: Excellent! Okay, that’s what we’re gonna be talking about. So I want you to explain to the listeners out there a little bit about yourself. I’ve known Jesse for a few years now. And first of all, we live in the same area, the same San Francisco Bay Area. But I am really impressed with how Jesse has, first launched a book in Asia, launching a book here in the United States as well – Lifestyle Entrepreneur. And how he’s really been able to create a lifestyle business where he travels all around the world, experiencing all kinds of amazing things and having a business that really supports that. So first of all Jesse, I want you to tell everyone at home a little bit about yourself and how you are here today.
J: For sure, I’ll give you the condensed version of how I wound up here today, and thanks for the invite. You know, I started out not even really interested in business per se. From a very young age, 13 or 14, I was in love with music, as electric guitar player, and I knew that that’s what I wanted to do, that was my passion, and I was definitely all in when it came to making music, my career. So, over ten years of playing in bands and travelling and trying to get some traction in that area, it finally got to a point where we had a band in Nashville; it was a rock band called Harsh Krieger and we were making a name for ourselves, and I saw this fork on the road where we could either sign with a record label, and have them take care of the business part of our career, that didn’t seem very appealing ‘coz there was like a 7-year commitment and we lost a lot of creative control. The path less travelled, which is ultimately the one we went, was to start our own record label, take on some additional responsibility but also have full ownership of our career and our creativity. And so I came into becoming an entrepreneur through the filter of my passion at that time, which was music. And after 3 years from starting our label, we recorded and released our album through an imprint of Sony Records, had our music at hundreds of radio stations, got to tour the country twice, and generally achieved what I’d always dreamed of as a kid. In the process, I realized I was really fascinated with business; and I saw how creativity in business, there are as many analogies with music. So subsequently, I left the music industry at a string of different companies that I founded or co-founded, which led up to writing “Lifestyle Entrepreneur.” Because each of them was in a different industry and different focus, and people would say, why are you going through doing music to renewable energy, to flash drives, to this that and travelling at the same time? And I said, well I’m gonna answer that question, I’m gonna do it through my book, “Lifestyle Entrepreneur.” So that’s the short overview of how I wound up where I am.
A: So right now, you are really a coach, an online business owner, you have a book program called “Business in a Weekend.” But before that, you were doing more manufacturing type of businesses?
J: Yeah, long before I started teaching people… It’s true, now I have a business called “Lifestyle Entrepreneurs Academy.” A program, some of which are inspired by you Alicia, the Business in a Weekend, was a derivative of your Bestseller in a Weekend, which is an amazing program and I was certainly inspired by it. But long before I ever started teaching people how to start businesses and have them integrate with their lifestyle, I founded or co-founded 5 different companies throughout my twenties. I’ve never actually had a normal job, it’d be worth mentioning. I truly, I think have the right to call myself a lifestyle entrepreneur, ‘coz I found one way or another, to make money doing what I love, which happens to be the subtitle of my book.
A: Excellent! Make money doing what you love – Lifestyle Entrepreneur. I’m really excited about that. Now, I always like to get these interviews started with a quote; it’s really a baseline get to us ready to discuss success, to discuss leadership. So what is your favourite leadership quote?
J: Okay, I got one for you. It’s from the great American general, George Patton, who said, “’Lead me, follow me, or get out of my way!”
A: Yes! Okay, so that’s good. I love that! Now, what does that mean to you?
J: Yeah, I mean that’s a philosophy to live by in a sense. I love being led by people who inspire me, and I always look upline to the people that are doing what I wanna be doing so I can learn from them, model them and have them lead me. On the other hand, right? As a leader, we both as leaders have our followers and people who learn from us. And the third option is, get out of my way, if you’re just gonna waste my time, then it’s not gonna be on my agenda for very long. But it’s being open to being led, always being humble enough to know that other people have answers that I still need, and at the same time, being an inspiration and a source of instruction for people that are looking to come up the ladder to the place where I’ve gone. So that’s what it means to me.
A: I love how you use the word source and I that’s a significant part of my definition of being a leader. It’s being a source – source of leadership, source of inspiration, motivation. It’s really sourcing, just like as the sun sources the world with light and really makes the world go around, and gives us life. How are you really as a source in your business, in your life, in your family? What does that look like?
J: Sure, I mean I’d say first, it may not be apparent but I actually feel that I’m an introverted person. I quite enjoy spending time alone and just do my own thing. But leadership requires stepping up and putting yourself out in the public space, and taking stand on issues and speaking one’s mind passionately and convincingly coming from a space of experience. So I make that a routine thing that I do; it’s to push myself far beyond my comfort zone, stepping to new realms of knowledge and learn the things I need to know to do what I love doing so that I can be and inspiration for others and sort of… I always think that I was leading from the front. If I’m gonna teach somebody else how to become a lifestyle entrepreneur, I myself need to be that quintessentially. And when it comes to being a source of leadership, I think it’s about putting a lot of information out there in training and resources, you know through my blogs, through giving away part of my book for free, free webinars that I run. There’s a lot that I do to inspire and instruct people, but no cost at all, no catch, but then the business piece comes when people decide, “Okay, I’m gonna take this step and improve my life and start a business.” Well then, there are additional options for training, coaching products and programs that do have a price tag. But just deep in that learning experience that I happily put out there for free as a leader, as an instructor, as a coach.
A: Okay great, sustaining as source is being able to inspire, giving people access to what you have, but also inviting them and being there for them to work with you further so they can really do the same thing that you’re doing – it’s being able to launch a lifestyle business. So I have a question for you, with all of these, in your 20s, founding and co-founding manufacturing businesses, I knew you were working in Asia, and being in your early 30s now and having now an online business, membership sites, lifestyle entrepreneur academy… How do you think you’re showing up in your life as a leader? Specifically what characteristics, like how to you wake up everyday, what is your daily routine to ensure that you are not in a place of, you know, hanging out, being by yourself? But, in a place where you’re out there, speaking on issues, standing up and being in a place where you’re holding a container for your community.
J: That’s a great question and I could go so many directions with that. I’d say, on the one hand, like I’ve always felt driven as if there’s just not enough time to do everything I want. So part of it is there’s a push and a pull. The push is feeling like, “Oh my god, there’s so many things I wanna do, there’s so many things I’m passionate about, but there’s not enough time.” I’ve got to hustle, work harder, like put in that extra effort. And I don’t know if that’s innate or if there’s something that adapted overtime, and I’ve always felt like I don’t wanna waste a moment. And so the reaction from that is like doing the actual actions that people see; writing new blog posts, shooting a video, creating an eBook, running a webinar, doing a training. Doing something out there in the public, facing realm that’s gonna be helpful, and instructional and inspirational. So I don’t have like a solid 10-point process on how I do this, but I make sure that every day I’ve got a number of things that I’m accomplishing that are moving me towards my goals. And helping my clients and my network of friends connect the dots and make introductions and be sort of a facilitator of relationships and progress, as well as somebody that’s teaching from the pulpit.
A: Okay, okay. Good! So we were talking about characteristics and you shared your leadership quote. What are some of your distinctive characteristics that you see in yourself as a leader and you see in other leaders that inspire you?
J: I think one is humility. I think as soon as we start to believe that we know everything, then the next thing that happens is calamity. So I always remind myself that with as much as I have done, that there’s still plenty more to learn. And that’s what I admire in other people as well, people that have embraced a culture of lifelong learning and contribution. I think with those 2 pieces, always giving back and focusing on helping others, as well as continue to learn and self-improve. When I identify that in somebody else, I think you personify this as well as many other people that I like to learn from, then that’s somebody that I want to lead me. And those are the qualities and characteristics I try to embody to be an inspiration. And I know that it’s working, when I get positive feedback from people I’ve never met who have either read my book or seen some stuff I’ve published online, and they’ll write me or I’ll see a press release or something come out where they’ll say, “I was inspired by reading Jesse’s book – Lifestyle Entrepreneur, and so I did X, Y and Z.” So I knew that making an impact, if it’s not just me having a one-on-one conversation, but the things that I’m creating and spending time on and putting out into the world and fan out and touch people and perhaps make that difference in their life without having even met them in person. So that’s why I know it’s working and those are the qualities that I try to embody to continue to push out new and helpful training and content.
A: Yes, yes. I was just thinking as you were speaking, you have your book – Lifestyle Entrepreneur, what would it be to be a lifestyle leader?
J: A lifestyle leader? I would be happy to take that role. You know, my lifestyle is pretty fun. In a couple of weeks into 2014, I’ve been to Hawaii; I was hiking into the Nā Pali Coast, spending time with the family. A few days later, I’m in Vegas at an Affiliate Summit West going to parties at the penthouse of the Caesar’s Palace, and like hanging out with all my friends in the internet marketing space. And so bouncing between different places, having a combination of fun, as well as business and networking opportunities, as well as relaxation and introspection to create the next thing… All of that plays into the lifestyle that I really love and pursue and talk about and help other achieve as well, ‘coz for me it almost seems second nature because I’ve done this so long, I’ve never considered the alternative. I felt I was giving up if I got a wage job, and I understand that not everybody is in a situation where they can just travel and have complete autonomy with their time, but that’s the goal to strive for, that’s the lifestyle piece. It’s to be able to wake up and decide day-to-day, week-by-week, what you wanna be doing, where you wanna be. And at least having enough of an income and a business underneath you to support that, and then you’re into lifestyle entrepreneur territory. So I hope that speaks to your questions of being a lifestyle leader.
A: Yeah, it’s all about choosing your priorities and then designing a life, designing a business, and designing your lifestyle around that. I think for me, someone was asking me a question, you know, how did I start my business and definitely being a single mom was something that… I created that because I wanted to stay home. So I’m like, “You know what? There was no exit. It was like, this has to work.” So I wanted to stay at home and have a business that was completely flexible, and that was really the impetus behind me starting a business.
J: And you’ve totally done that. I think it’s great. What you said right there really touched me, there was no other option, there was no exit. Whether or not it’s real in my life, I try to create that dynamic where it’s like, it’s not an option to be mediocre, or normal, or waste this precious time that we have in life doing things that don’t make me feel alive and inspired. It’s an imperative, really. If it’s an imperative, then you’ll find a way to make it work. If it’s not, if it’s like a hobby, then maybe, you know, I’ll dabble an online business, well then maybe you will, maybe that fits your overall lifestyle goals, but to really like do this for real full time, requires a commitment and a mindset of like, there’s not another option. And once you get there, you’re probably half way there because then you’ll find a way to do it and just about which one is the one that works for you, for anybody that’s listening to this and thinking about it. There’s another great quote that I’ll throw out from Mark Cuban where he says, “You’ll only have to be right once.” You can be wrong 15 times, and in number 16, boom! You’ve got it and your whole life will change. And things will open up and that can carry you through the next 15 things that you do of trial and error.
A: Trial, error, failure – all leads into this. So that leads us into our next question, it’s something I’d love to ask. So you said you’re ready to play all in, and I want to ask you and really see… What does playing all in mean to you?
J: Playing all in to me is all about taking advantage of each day and looking at each day, each week, looking out over the months and the years and taking the initiative to plan out what I wanna be doing and then the big goals that I wanna hit; the things that I wanna create, whether it’s a new book, and making that a priority. So playing all in for me is saying, okay, if I know I’ve gotta do, you know, 2 chapters editing on my book, then that’s getting done in that day. And then everything else can come afterwards, if I need to do mundane things like get groceries or whatever, I don’t brush off the, it’s like what Bill Clinton says, “I don’t major in the minors.”
A: Oh! He said that? I use that term all the time, and I never knew he said that. “Stop majoring in the minors.” I always say that. Bill Clinton, gotta love him.
J: Some people are great at doing the mundane stuff, you know? They’ve got their productivity systems as to when they’re gonna work out, when they’re shopping, and blah blah blah. Okay, but what’s the overarching that’s really gonna make you feel that you’ve accomplished something? Yeah, the vision.
A: So, what is your vision?
J: My vision, it’s evolving. If you asked me 2 year ago, my vision would to be very close in the situation I am now. To have a book out, to have hit a bestseller, which I did in Asia, to start a training academy and work with hundreds of people, from literally all around the world, to go down this path of lifestyle entrepreneurship. So now I think success requires us to expand our vision, and so my vision is actually expanding like real time now, and seeing what’s the possibility of now. My book is ready to come out to the US, and eBook all around the world, having my 2nd publishing deal in as many years, and it’s forcing me to think bigger and see what are the next goals that I wanna hit. Now, I’m starting to focus more on financial goals ‘coz for so long it was about lifestyle and having the freedom and ability to travel for months of the year. And so now, I’m really getting serious about building wealth, so one of my goals is financial and I reference back to that. I know what I wanna hit, revenue lies this year, next year and in the following ones. I never prioritized that before, I always prioritized, how can I go live in Asia for the summer and study Chinese and just have fun and not focus on work. But now I feel this drive to like impact… Somebody said, if you touch a million people’s lives, you make a million dollars. So I just wanna expand the reach of my message in my Lifestyle Entrepreneurship to, quite literally, millions of people. And I know if I do that, even if it’s in the form of giving stuff away for free, and putting my book out there, that it’ll eventually  circle back and help me realize my personal ambitions of financial growth and wealth generation. So I’d like to keep the focus on the benefit to others, whereas I have my own goals for finance and wealth, but that’s the result of helping thousands and thousands of people, and as a result of that, then I get the reward financially. I kind of frame it into helping others and providing value, and then after providing value, you realize that in the form of money.
A: And really focusing outward, I think that’s what leadership is all about, it’s focusing outward. And how Deepak Chopra in The Seven Spiritual Laws of Success, talks about asking yourself on a daily basis, “How can I serve humanity?” It’s another baseline grounding type of question. How can I serve humanity today? Am I serving humanity by running around with my hair on fire, totally stressed out in a place of scarcity? Or am I serving humanity by fully being in a place of how can I serve, how can I create abundance and wealth which I’m in all areas of life and forgot someone else. That’s a good way to play all in.
J: Yeah, I look at it really in two ways. It’s like if you’re in a place of struggle or lack or discontent with your lot in life, then I think a good initial goal and vision is freedom to be able to what you want, whenever you want and whomever you please. That’s actually my definition of success. But once you have that and you really experience it, have fun with it. Go travel, do some things that are personally enjoyable, really embody that new found freedom and then, I think that drive to serve question of how can I serve humanity becomes more relevant if it’s coming from a place of freedom and abundance instead of… If you tell somebody who’s like in a mountain of debt and hates their job, how we can help humanity looking everyday like, well, you could start by getting me to ground level, I’m underwater. So I think it depends on where you are in the spectrum, adjust your vision and willingness to be of service to humanity, as well as your capabilities to do something. I think it’s one of the goals of lifestyle entrepreneurship, it’s to have that freedom as a starting point, and then you can choose any direction, you can choose your own adventure.
A: Okay, so what are you specifically doing today? ‘Coz I wanna set you up to win. What are you specifically doing today to play ALL IN in your life? You look like you’re sitting in a comfy office, sunny outside; I know we’re in the same… We’re probably 5 minutes away right now; it’s like 70 degrees in January. So what are you doing specifically today to play all in?
J: You got it! I woke up earlier than I would have liked to, so that I can put on work on a new program that I’m launching; a monthly subscription like membership and training site. And I’ve already had 2 calls with people in 2 different countries doing coaching, got a workout, ate a healthy lunch. I’m here all in with you, 100% at this talk. And right afterwards, I’m meeting with a client and helping him launch a new business, a new client, and then another call, and then my day is starting to wind out, I’m gonna do something fun – probably gonna go a drink with a friend in the city. So what I’m doing today it’s half over, and I’ve already been on the phone helping people in different countries move towards their lifestyle goals, worked on my own health and fitness, happy to be here with you, contributing whatever I can, and then going back and helping other people in the course of my coaching and consulting work. And at the end of the day, I will feel like I have spent it well.
A: So being a source, definitely what I hear is you’re doing a lot but really being a source of happiness, helping people, supporting people, connected.
J: I love just building momentum throughout the day. I’m not a morning person, but if I make myself get up, earlier than I’d want to, splash some water on my face and then I’m like start hitting it, it’d start to build momentum and by noon, it’s like 1:30 right now, and I’m like, on fire! So I got another good 5 or 6 hours of like inspired contribution through my work, through my business, and then I’ll have some me time after sundown.
A: Good! Inspired contribution, I love that. So Jesse, how can people learn more about you as we get wrapped up? What I love to do for everybody listening is to offer you a copy of my book, Lifestyle Entrepreneur as well as a webinar that I run called “The Five Keys to Building a Successful Lifestyle Entrepreneur Business,” and that could be found at And that’s really the front end, what I give away for free happily to share and inspire and help people learn about my story and what I do, and then for people to wanna go further, I run a Business in a Weekend virtual bootcamp, inspired by none other than Alicia Dunams. We play all in all weekend, from Friday to Sunday, 12 hours of teaching, training; all delivered via webinar with a private Facebook group and a membership portal. Giving tools and strategies, based on my own experience and others, on how to get started down this path. Starting a business, doing what you love, where you can run from all over the world, with a little more than your laptop and an internet connection. That’s really the promise of my brand and what I do and it’s the lifestyle that I try and embody and play all in with my own life day-to-day. For anybody that that sounds appealing, just head to, grab the book for free, check out the webinar, and maybe I’ll see you on a future Business In A Weekend.
A: There you have it; we have Jesse Krieger playing ALL IN in his life. Thank you so much Jessie for sharing your inspired contribution with our audience today. You take care, Jesse.
J: Thanks a lot Alicia, talk to you soon.
A: Bye!

[su_button url=”” target=”blank” background=”#efcf2d” color=”#000000″ size=”8″ wide=”yes” center=”yes” radius=”5″]Download the Transcript for this Podcast[/su_button]

Leave a Comment

Your email address will not be published. Required fields are marked *