From Broke To Seven Figures With Lewis Howes

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After his career as a pro athlete came to an end, Lewis Howes found himself jobless sleeping on his sister’s couch for over a year…

Then he became a seven-figure entrepreneur, top business podcaster, and connected with guys like Tim Ferriss and Gary Vaynerchuk. His new book “The School Of Greatness” just hit the New York Times Bestsellers list.

In today’s Pathways To Wealth episode, Lewis shares his journey from broke and depressed to being one of the world’s most renowned lifestyle entrepreneurs. One thing I love about Lewis is his authenticity around building businesses and becoming a high-performance person in all areas of life.

You won’t want to miss the knowledge bombs he drops in this episode…

  • How Lewis built and sold his seven-figure business
  • What looks for in a startup before he invests as an angel
  • Why it’s so important to hustle every single day
  • How to turn adversity into advantage
  • How someone can turn their vision into a reality
  • Lewis’s two year journey from pro athlete to entrepreneur
  • Why you need a bigger vision than just chasing money

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Introduction: In this episode of Pathways to Wealth, we’re talking to Lewis Howes, former pro athlete and author of the New York Times bestselling book, The School of Greatness, an incredible read and Lewis is going to drop some knowledge bombs on this episode about how we went from broke living on his sister’s couch to building and selling a 7-figure business. Let’s go ahead and jump right in.

Chris Dunn: Hey everybody! Chris Dunn back with you and I have another great interview today with Lewis Howes, author of The School of Greatness. Lewis, how are you doing man?

Lewis Howes: Good to see you man, thanks for having me.

Chris: Yeah, thanks for coming. Right now, you're on a world book tour, how’s that going?

Lewis: It has been incredible man. I think this is like the 15th city I've done in the last 5 weeks, so it’s been traveling around the world, not much sleep, but lots of great people I've been connecting with and a lot of fun.

Chris: That’s amazing man. What was is like writing the book?

Lewis: It has been a journey. This is a really 8-year dream of mine. I wanted to write this book like this 8 years ago. But really, it wasn’t until 4 years ago I started reaching out to different agents and figuring out the whole process and then in the last year and half is when I really started to dive in. It’s a lot of work but a lot of fun.

Chris: Nice. The subtitle is “A Real-World Guide to Living Bigger, Loving Deeper, and Leaving a Legacy” What does that mean to you? What does greatness mean to you?

Lewis: To me, greatness is discovering and cultivating the unique talents and gifts that each one of us has to pursue and follow our dreams, how are those dreams may look along the journey and through following our dreams, making a full-time living supporting ourselves and impacting the maximum number of people around us. That for me is what greatness is.

Chris: Nice. Beautiful. Now, I know you’ve been a former pro athlete, an Olympic athlete, lifestyle entrepreneur. Tell us a little bit about your history and where you come from?

Lewis: You know, my dream was always to be pro athlete and I made that happen, I played Arena Football and then I got injured and I was sleeping on my sister’s couch for about a year and half trying to figure out what the next step was going to be for me and that’s when I had this vision for this book. This dream was like, “Okay, I want to make something of myself but I have no money. I'm on my sister’s couch. I have no skills, so how am I going to make it happen?” And literally early on, I just said, okay I got to find people who’ve already done, who’ve already been there, who have done that, and who are already successful and learn from that because they know the path, they know what it takes, so if I can take a lot of action doing what they tell me do, I can probably figure it out. I don’t know when it’s going to happen but it can start happening.

I found a few key mentors early on that gave me challenges. I became an athlete of life and they gave me challenges, workouts, exercises, mental, physical, different things, and I just took a lot of action.

Chris: Nice man. What are your latest business ventures? You're into all kinds of stuff but what’s your latest thing in addition to the book which I'm sure has taken a lot of time.

Lewis: I create a lot of online courses with The School of Greatness. I've got different programs and products. Next year is interesting because I've got all these products that are currently running and they're great but I'm trying to figure out what the next bigger step is, so I'm in that process right now at the end of the book tour, wrapping it up and I’ll re-evaluate soon.

Chris: Okay, nice. The theme of the show, Pathways to Wealth, is basically how to create income, build capital growth, and time freedom which I think there is a lot of crossovers and messages that you talked about in this book and I love the chapter on “hustle.” What does “hustle” mean to you?

Lewis: When I played sports, I never was biggest, fastest, or strongest but I was always willing to dive for the loose balls on the court, on the field, wherever it may be, I was always willing to dive and do whatever it took to show that I was willing and I always stayed on the court, in the field because of that. The coach wants to put people in who are willing to hustle, who are willing to do whatever it takes. We’re rewarded when we’re willing to do whatever it takes in business, in life, whenever we’re spending the time, the hours, energy into doing it, and there are so many people out there who just want it easy. I'm telling you, you know this, we got to put in the work for a certain period of time in order to make things easier for ourselves where we don’t have to work as much later. A lot of people aren't willing to hustle for a period of time to build that momentum and skills and that’s necessary.

Chris: Yeah. One of my messages is ABH, “always be hustling.” Every day should be an opportunity to get one or two steps closer to your life mission or your big vision and your vision is like ten times mine, so I have a vision of 100,000 people becoming financially independent. Yours is like 100 million. Tell us a little bit more about your vision.

Lewis: Yeah, I want to teach 100 million people or show them how to make a full-time living doing what they love. I think that’s going to heal the world. I think when people are fulfilled – when they're making money doing something that fulfills them, they're going to feel better about themselves. They're going to treat themselves better and other people around them better. That’s what it’s all about, having a good life, having fun, feeling like we’re doing something that matters, feeling passionate about what we do, and inspiring others around us to do the same thing.

Chris: Yeah, absolutely. A lot of people just focus on the money and you can be a miserable millionaire. That’s a real thing isn’t it? I'm sure you met a lot of people like that they don’t own their time. They just work for the dollar and they look back 10 or 20 years and they say, “What the hell did I do?”

Lewis: Exactly.

Chris: You’ve done a little bit of angel investing up here?

Lewis: I have.

Chris: Tell us about that. [crosstalk]

Lewis: I think about 5 or 6 investment angels. I just look for stuff that I feel is a great team, something that I'm passionate about, something that I'm interested in, and I feel like it has a big upside. I'm an investor in a company called Skimlinks. I've invested 5 years ago in them and they're an affiliate marketing company so I wanted to learn more about that world back then, so I invested in them. I've invested in a mobile app company called Mobile Roadie. I've invested in a food delivery box service called Foodie and a few others. I'm always trying to put my hands on a little bit of everything.

Chris: Nice. How you do find the deal flow? I consider myself a baby angel. I just got in this space about two years ago, joined some local angel networks in Austin just to see the deal flow where you see 20, 30, or 40 pitches a month. Where you do get your deal flow? Through networking or—

Lewis: I just ask people. I'm connected with some big CEOs in the tech world and I just say, “Hey, if you ever hear of anything just let me know” and a lot of people just reach out to me because of my platform and they’re like, “Hey, will you invest?” They just ask me. I think I get a lot inbound but also I’d like to just see what’s happening and ask friends. They keep me in the loop as well.

Chris: Let’s talk about adversity. I get emails probably like you do on a regular basis, people like, “Hey man, I've been at this for a few months or a few years, I'm not gaining traction. I'm stuck in the mud,” what would you say to somebody who’s like 25 or 30 years old trying to hustle, doing everything they can to get ahead but they just feel like every day is a spinning of the wheels?

Lewis: I would say as long as you're chasing your dreams, you're going to be going through some tougher adversity on the journey no matter what even after 8 years of putting in the hustle and the work and the energy and seeing a lot success I've had over the last 8 years, making good money, getting great results, coming out with books, being a New York Times Bestseller, even with the success of making at some level, there are still challenges for me every single day. There is still adversity all the time because I have bigger dreams and goals and so what I would say to someone who is starting out and they want it now and they're feeling they have all these adversities, it’s like “Get used to it” because it’s always going to be there and the sooner you embrace it and say “awesome, I'm excited for this challenge” or “to overcome this challenge,” the sooner it’s not going to not make you suffer and you're going to just see that this is part of life, that adversity is necessary in order to get to the next level.

Chris: Yeah. I agree with that. I think that it comes down to confidence. For somebody that’s maybe getting out of their full-time job or kind of struggling, even getting the first little success, I can see where that would be mentally difficult, but for me, I think it’s all about once you make one big leap and you see some success, and you know, okay, that for me was really difficult but then I pushed through and I had success gives you a little more confidence and then you start to look at challenges and adversity like a game. Like, “Hey, what can I do to take it to the next level?” and then it’s not a scary thing. It’s just like stair-stepping.

Lewis: Exactly.

Chris: Awesome man. Let’s talk a little bit about your prior adversity and how you came from being a pro athlete into an entrepreneur? What was that transition like?

Lewis: It was challenging man because my whole life my dream was to become a pro athlete and when I was done, didn’t have a backup plan. I didn’t have any money. I didn’t have any skills. I wasn’t sure what to do, so it was just like a depressing time of uncertainty, and again, a lack of confidence because I wasn’t sure what was next. It took about 2 years for me to get out of that funk. It took a while. It wasn’t like this easy transition like, “Oh, okay. Now I know what I want to do.” It took some discovery. It took some recovery. It took some healing. It took trying different things and making a lot of mistakes. I did a lot stuff early on that didn’t do me anything but the process of doing it and learning has continued to get me to where I'm at. Even if it wasn’t something I want to do for my vision now 8 years ago, it still showed me a process of how to work hard and how to learn something. LinkedIn was something I did early on but it’s not something I use now. But the process of building something, creating value, creating a program, writing a book about something, that allowed me to give me the tools, the skills, and the experience to do what I'm doing now. Even if it’s not what you want to do or it’s not getting the results you want, it’s still a great process to get you where you want to be.

Chris: You can still learn right? It’s a stepping stone.

Lewis: You can learn, yes.

Chris: Is the LinkedIn business, is that the one you just sold?

Lewis: Yes. It was part of all this online programs I created on social media and that was one part of it, yeah.

Chris: Okay, great. And that launched you into The School of Greatness?

Lewis: Yeah, I was just kind of like, “Okay, what’s next?” I'm in a new transition. I sold this company and do what I want to do now for the rest of my life or the next few years and The School of Greatness was that.

Chris: Tell us about The School of Greatness. What’s that about?

Lewis: The School of Greatness started as a podcast. I said to myself, I have this incredible network of influencers and inspiring people from all walks of life from sports, from business, from spirituality and I have these incredible conversations with them but other people don’t have access to this, I wish I could give them this insight that I'm learning.

Chris: So you used your connections to build that and bring that to your audience. I know you have one of the top business podcasts and a huge following. What kind of downloads do you get a month?

Lewis: This last month, we did 1.15 million downloads last month alone. So I think we’re at 11 million downloads total now.

Chris: Nice man. That’s great. We’re just really starting to launch the podcast now and I look at guys like you and James Altucher and everybody has a history that— I kind of had the same thought as, “Look, I know a lot of successful entrepreneurs, traders, and investors, and a lot of these guys nobody has heard of before, so how do I bring that to the masses?” So I started looking at what you guys were doing, modeling that, and you do awesome video interviews like this and so I was like, “Man!” I would encourage anybody that has connections or some kind of unique experience to start a show or a podcast or something because information is really like the most valuable thing that we can share with each other and for us to achieve that goal in that vision of helping, a hundred million or a hundred thousand in my case, people achieve financial freedom, I think that’s a great way.

Lewis: Thanks man. I appreciate it. Yeah, it’s been fun. It’s been a blast. We’d be 3 years by the end of January and it’s unbelievable what’s opened up for me because of it. The book deal came because of the podcast and all these people I get to meet who want to come on the show are because of it. Without the platform, I won't be able to create these experiences.

Chris: Yeah, that’s great man. How long did it take you to write the book?

Lewis: Once I had the proposal done and everything – well, the proposal took like a year, but once I had it all flushed out, I'm ready to go. It took about six months to write the actual book.

Chris: For me, it was a grueling process. I have a book about trading bitcoin and it’s kind of technical. But for me, writing is just incredibly difficult. Was it tough for you too?

Lewis: Very challenging, that’s why I bring on a great team around me to support me in the whole process.

Chris: Did you have any co-authors?

Lewis: I had some people help with the writing, help with editing and the proofreading, and the layout – everything. Every aspect of the book I had someone helping me with. It. it wasn’t just like, “Oh, I'm gonna sit down and write the whole thing.” It was like, “Let’s work on this together.”

Chris: Yeah, that’s great man. Let me see, was there anything else you wanted to talk about? Any specific aspects of the book or the program?

Lewis: What I want to say for people listening—what are most of the listeners here? What is their biggest challenge you think?

Chris: A lot of the audience that we talk to are traders, investors, or first-time entrepreneurs that are either trying to solve a problem or develop a skill set like trading and investing, be it real estate or the stock market or this new world of bitcoin and digital currencies. It’s highly emotional. It’s very skill-based. A lot of people think that they can just read a book or watch a course on how to trade or how to invest but whenever they get into the markets they figure out, “Wow, this is just like baseball or golf” or in your case, like handball. It’s like you can learn but then you have to practice and then you have to execute, so that’s one thing that I think you really refined, the craft of skill development. You performed at a high level, in Olympic sport, professional sport. What kind of advice would you give to somebody, maybe an investor, a trader, or an entrepreneur on the mental side of how to just perform when the heat is on.

Lewis: You know, I think it comes down to getting clear on your vision and what you want. If you're just chasing the money, then everything’s going to be harder to perform because you're putting too much pressure on yourself but when you have a bigger vision around why you’re making money or why you're investing or trading or doing these things, that is a deeper why, a deeper why of impact with your family, with your life, with your community of giving back when you have that foundation and grounding and attention.

I think it’s much easier to create great results because you're not as scared or stressed or fearful, You're coming from such a more deep powerful place, like you want to impact a hundred thousand people to create financial freedom but that’s inspiring as opposed to, “I just want to make a couple of million bucks.” That’s not as inspiring because when the pressure’s on, you're going to be focusing on the money as opposed to the mission.

So you got to get clear on what your mission is and then build a great team around you of supporters because it is going to be challenging, it’s going to be hard, it’s going to be adversity. If you don’t have the support team, whether that’s your family, your relationships, the business team, whatever it may be, it’s impossible to achieve greatness on your own and it’s not fun or rewarding either, so find a team and have a bigger mission.

Chris: Yeah, that hits home man because a lot of people when they focus on the money, if you get the money, it’s disappointing. It works like, “Okay, well I hit this level, now what?”

Lewis: Now what? It’s not fulfilling.

Chris: Yeah, I’ve had this dream when I was in my early 20s, I’m like, if I could just make a million bucks in one year. I would be so happy. When I did that, it was like, “cool” great. We celebrated for a day. We crossed a million, now what?

Lewis: Exactly.

Chris: But when you focus on, for me, it’s like the process right. It’s like if you focus on the process, the result will come and it won’t be just like a – “woo” – and then back to depression or whatever. Now we’re staying on course and as long as you focus on the process and like you said, the mission, that’ll will carry you through both the bad times and the good times.

Lewis: Exactly.

Chris: Nice. Well, one thing I’d love to do Lewis, is every week I give away a book. For you guys that are watching this, the day that I release this episode, I'm going to see if I can get Lewis to sign this and then we’ll give this away on periscope whenever we launch this. For those of you who that are watching us on day one, you’ll have a chance at winning that.

Lewis: There you go, sweet, I appreciate it.

Chris: Yeah, awesome. Thanks for stopping by. I know you’ve got a book meet-up tomorrow night. Where you at after Austin?

Lewis: Go back to LA and then I go as my final stop in San Diego next week.

Chris: Awesome man. All right. Well, thanks for stopping by man. It’s great to see you and good luck with the book and everything else you got coming in the future man.

Lewis: I appreciate it. Thanks Chris.

Chris: Where can people go to connect with you.

Lewis: They can go to or they can go to The School of Greatness podcast on iTunes and subscribe there.

Chris: Absolutely. We’ll go ahead and link everything up in this video and on the podcast guide, so thanks for stopping by man.

Lewis: Thank you very much.

Chris: Well, a big shoutout and thank you for Lewis for stopping by the studio and doing the interview today. Go to to grab his book. That’s – G-R-E-A-T. This is an incredible book and it talks a lot about some of the messages that I talk about on a daily basis like developing hustle, the importance of waking up every day and doing something that gets you one step closer to your ultimate vision and also practicing positive habits. There are just so many golden nuggets in this book that it’s really a game changer if you're an entrepreneur, trader, investor, or anybody who just wants to be high performance in life. Again, go ahead and grab that book and I will see you in the next episode.

About The Author

Chris Dunn is the founder of Skill Incubator. He is an active investor and entrepreneur with the mission of helping people learn Skills to thrive in today's economy. Chris spends his time testing and building multiple streams of income and investing the profits. Read more here.