Crashing and burning was never part of the plan. But when Damion Lupo did, he used that period of suffering to rebuild himself into a financial dynasty. Damion Lupo has started and owned more than 30 different companies including an insurance agency, a precious metals firm, a venture capital company, a financial consulting firm, and more than a dozen real estate investment and development companies.

He is a 5-time author and sought after financial consultant for accredited investors and business owners.Using a vast knowledge of financial markets, money psychology and pattern recognition he’s an expert at quickly diagnosing hidden financial cancers with clients and their organizations and rewiring both for success.

Financial Mentoring with Damion Lupo

What would happen if you build the business on a credit card, grew it to $20 million, 150properties, and then lost it all? Would that be a bad day for you? The gentleman you’re going to hear from, Mr. Damion Lupo, did that. He’s recovered quite nicely. Damion, could you tell us the story?

Mitch, it’s great to be here. It’s a story that I didn’t want to share for a while because it was so painful. Now, it’s one of those things where I look back and go, “What a gift I have gone through that thing.”In the beginning, everything was good. I was struggling along building my business, and I did that for about eight years. I started out with a credit card, buying a rental house and cutting my teeth in the real world of real estate investing and business. I built up a team and everything was going pretty well, especially because I seemed to have time to market, which was a coincidence. When we time things and end up on the right side of something, it’s good to embrace it, and I did. The problem was I ended up not realizing that I didn’t have a foundation.

About eight years later, I ended up with a $20-million portfolio that absolutely blew up during 2008, and so a multimillion-dollar net worth vaporized. I had to sit in a time-out box for a few years and lick my wounds, start over, and ask the question, “How am I going to do this different next time? How am I going to be different next time?” I had to spend a few years figuring that out and then started over. That’s where we are now. We’ve built a business. I have created something different. It’s different because there’s a different foundation, because there’s a different me. I rewired me and that was the huge difference that if I hadn’t done, I probably would be sitting on a similar type of ticking time bomb like I was in 2008.

I’m going to intensify the pain a little bit because a lot of our audience couldn’t conceive of building a business to that size and losing it. What happened? You said that you did not have a foundation and I understand that, but what did that mean to you?

I didn’t build it based on values and a mission. I built my business based on how much money I can get. It was about how much I could get more than anything else. In the beginning, I was trying to keep myself from starving to death, and so I worked hard to build new properties and new business relationships. I was trying to get things going, so there was a lot of activity, but it was in all different directions. It wasn’t focused on a bigger mission of impact and something that I could scale that would be sustainable because it didn’t have the strong foundation. It was just based on me working my butt off. A lot of people are like that, they’re working real hard.

When I went through the process of things going vertical, I went from clunking along to millions of dollars coming in. I started harvesting. Instead of having my business continue to grow, I was spending and consuming my business. I was thinking that I was the world’s greatest guy and I was invincible. I was spending faster than I was creating, even when I was making seven figures a year. Sometimes, it was hundreds of thousands of dollars a month. I didn’t have the mindset of long-term sustainable and scalable. Without a mission, all I was doing was spending because I didn’t feel that I even earned it or deserved it. Without a mission, I was in for a rude awakening when the markets changed because I didn’t have that foundation that would sustain me.

I could relate to that. I built a software company and I sold it for eight figures. I went from having $6,000 in the bank to all of a sudden having $5 million in the bank. I felt those same feelings. I felt like I didn’t deserve it in a way, even though I had worked for all those years. Sixteen-hour days and all the time we spent building our businesses and then all of a sudden, it shows up. When this happened, tell me about the process of breaking it all down and taking it apart, getting rid of the elements that you had to get rid of in order to scale back your life so that you wouldn’t be completely bankrupt? 

To be candid, I absolutely was bankrupt. It wasn’t so much the money bankruptcy, it was the emotional bankruptcy. I was $5 million plus and then I went literally to negative $5 million plus. The biggest problem I had was that I tied my self-worth and my net worth together. When I went down to the negative millions, I looked at myself as worthless. As any sensible person would do, I ignored it and denied it, and pretended everything was good. The most important moment in time was the moment where I decided I’m going to start telling the truth about everything.

In 2010, when I was volunteering for a Senate campaign, I got fired as a volunteer. I rejected that. I claimed online that I did not get fired, that I resigned. I finally looked at what I was doing and said, “I’ve got to start telling the truth about everything because that’s what’s got me into a lot of trouble. Until I started doing that and take responsibility for everything, nothing will change. I’ll end up in another situation.”The process was asking those questions. What’s true about me, my belief system? Who I am? That’s how I was able to move through all the old stuff, the old me, and let go of this idea that I am my net worth. That was a huge thing to shift into our past.

It’s a very common thing, particularly for alpha male entrepreneurs. If we spend any time on Facebook, we see them in their Rolls Royce’s and we see them making videos and wanting to sell $67 products and you could do it too. We’re driven by that feeling that we are our net worth. How did you unravel that? The concept is absolutely correct, but the path to it is what interests me. How did you get there?

I got help. I went and said, “I’m not good enough to figure this out on my own. I’ve got to be vulnerable. I’ve got to go into a space and ask for help from somebody that can hold that space for me.” Sometimes, this looks like a coach. Sometimes, it looks like a therapist or a mentor. In my case, I spent a couple of years with a therapist, and he mostly sat silent. It’s interesting because great people oftentimes don’t say much. They are just powerful at holding space. I started working on asking the questions, pulling back the layers, and then I found a place, another space where I could be present. That’s where I went in and started diving deeply into the martial art training and teaching that I had been doing for the previous ten years. The more I was there, the more present I got, the more grounded I got. That’s where I started to find myself. It wasn’t a flurry of activity chasing dollars. It was becoming present to who I was and experiencing that instead of chasing the next bling on Facebook.

You took a step back, you re-evaluated yourself, you focused on the inner world instead of the outer world. I bet that decision was difficult. After all, you’ve been so driven. I don’t have to ask about all the toys that you lost, I am sure there were plenty. You had to set them aside and the act of doing that must give you the feeling of what they were worth, which was pretty much nothing. When that happens and you set aside the Rolls-Royce’s and all the other stuff and you’re deep into self-exploration, is that where this transition took place for you?

You mentioned the internal work. The hardest work that we’ll ever do is the internal work. A lot of times I see people and they thought, “If I fix the outside, then it’ll all work out.” That’s not true, because the outside is a reflection of the internal, and so we have to go inside. It’s hard and it’s painful. I spent the time doing that and then the external started shifting and changing. It didn’t have the same meaning to me because it was an outcome. It wasn’t the focus, it was a side effect more than the driver or the target, and that’s what the shift was. It was getting my inside right, my mind right, and getting into a space where it could create an external world that was love and peaceful and abundant, not one of fear or scarcity where I said, “I’m not worth that.” If there’s monetary wealth or physical wealth, it’s in alignment with the abundant inside. I’m not fighting or trying to get rid of it. I’m able to embrace it and keep it.

If somebody says, “I identify with what Damion is saying,” where should they start? Is there a thing or process a program? How did you get to the point of being able to do this work? 

YFTC 005 | Financial Mentoring
Financial Mentoring: Reinvented Life

A lot of blood, sweat, tears, pain, and mud. The process was just slugging through it. In 2012, I started writing about all of these things and journaling. That ended up being one of the books that I wrote about my story. What I ended up doing inside that, all the questions I was asking through the process that I went through, I have built a framework. Part of it was to have a cathartic way of getting through everything that I was processing, and part of it was because I wanted to share what that process was for people that are trying to reinvent themselves or change something. It was a combination of hundreds, if not thousands, of books and programs and mentors and coaches. It came down to reinventing my life, which is why I called the book The Reinvented Life, because that’s what I did. It gave me those questions. Hopefully, there are people that will take those questions and use those to start because if you ask the right questions, then you get better answers. If you ask the wrong questions, you’re going to have bad answer.

I know that you went through this boom-bust cycle, but the real beginning came recently. Tell us about how you restarted your business life, your external life, and how you got to where you are now.

I started small again. I was doing things that were $10, $20, $30. It was a humbling thing because I was in the middle of multimillion-dollar projects. I started off and said, “Nothing is too small and the details matter, and every person that comes into my life is going to matter.”I started building something and creating. I put a lot of energy and activity into building a lot of relationships and one-offs with people. It was different because my focus was on guaranteeing a delightful experience. In the beginning, it is something that we hesitate doing. We’re afraid that if we guarantee anything, people are going to take advantage of it. I had to decide that I was okay with a small group of people, maybe that’s 5% of the people taking advantage of that type of thing, because I wanted to create an experience for people that they fell in love with. That was one of those unique ones where we say, “That company is world class.”

From the beginning, that was the process. How do I do this? I didn’t know how to do it very well, so I went out and tried a lot of things, engaging with people and seeing what the market wanted, see how they responded. When I made the mistakes, which are inevitable if you have a lot of activity, I embraced them and owned them. It comes back to the value of self-responsibility. I never blamed anybody for anything. If the Post Office lost a package that I was shipping, it was my fault. I owned it and I made sure I fixed it for my customer. That’s a big difference. We all experience responsibility. We experience blame when we’re dealing with businesses and companies. Even when something blows up, I love when somebody says, “It’s mine. I’m going to fix this. I’ll make it right.”

That’s what I’m striving for. I’m focusing on making sure that the culture that is being created is all about that, so we have a delightful experience. Even when it’s a mess, even when we fail, we come back, and we say, “That’s us. We’re going to make this right.”That’s how I restarted. That’s how I showed up and then figured it out by bringing in great people. The truth is I’m not that good at many things. Other people that are, if they buy into the vision of what I’m trying to accomplish and they get on board, then we can create a world-class experience for all of our customers and clients because of that teamwork.

It’s the foundation of becoming a successful adult in life. It is to take full responsibility for everything around you even when it may apparently not be your responsibility. That’s what responsible adults do. They don’t blame others. It’s a beautiful place to be. It’s a great place to live when you know that no matter what, you’re going to say the truth, you’re going to tell your truth, and you’re going to take responsibility for that in your space.

There is a true sense of freedom when you’re willing to be completely transparent and candid in every place within your family, your relationships, your customers, and then own things. It shifts the conversation. It completely shifts the energy around who you are and who you attract and who you repel when that’s your norm. When anything outside of that is absolutely rejected, it changes everything for the better.

You restarted your business, you began doing what? Was that going out and doing real estate again?

When we get burned really bad, it knocks us off course in terms of our confidence and our ability to do the same thing. I shifted away from real estate. I didn’t want to touch real estate for a while. In the last couple of years, I started getting back into it. The thing that I started doing was I was in the precious metals world where I was starting to sell precious metals to people. I started it on eBay. That was how I was able to start these little transactions. That’s where I began to build up my reputation and the client base. It was building a reputation. Over a period of a couple of years, there were 5,000 positive testimonials. That was the foundation of who I was, how I was showing up in the world in business, and the different me that was showing up. My reputation was right there in front where everybody could look at it and read about it.

YFTC 005 | Financial Mentoring
Financial Mentoring: There is a true sense of freedom when you’re willing to be completely transparent and candid in every place and own things.

Tell us the way that the universe brought you that opportunity to begin with.

When I was in the middle of my meltdown, one of my close friends said, “God told me to tell you to go do this.” I am not necessarily a very religious person, but for whatever reason I didn’t argue. We get messages all the time from different people in different ways. When these things happen, sometimes there’s a moment where we have to say “I don’t know why, but I’m going to go. I’m going to take action. I’m going to do this thing.” That’s what happened for me. I started and went for it and kept my head down instead of chasing squirrels. I was there with that message and I ran with the message. A couple of years later, there’s this thing that had been produced and I went, “Wow.” It was because I stayed focused on that one thing.

The world is flooded with information, signs, and guideposts to tell you where you need to go. It doesn’t mean you have to be frantically turning from one to the other, but listen in and feel what resonates with you. When something like this happens, jump on it. It might be the thing that get you to where you want to be. I love what you said about keeping your head down and moving forward. You needed to locate a source of precious metals and then you needed to understand the market. Was this a completely new world for you?

It was something that I saw as a kid because my dad was in this world, but I didn’t get into it until that moment. When I did, I went all. I ended up writing a book on precious metals because I didn’t understand it when I first got in. One way to understand something is to teach it. If I can teach this and be clear about it, then people can understand what I’m teaching. That probably means that I understand pretty well myself. I went all-in on it and understood the markets. There’s something powerful about that.

We can feel when those signs come up or somebody that we’re reading or listening resonates with us. Instead of bouncing to the next thing, if we embrace that and not drink the Kool-Aid but start swimming in the Kool-Aid, you can go all in. You’re like a scuba diver surrounded completely by this message or this thing that you’re doing and embrace it, embody it, and become it. It does change everything because people start noticing that you’re all in. We love people that are all-in. That’s who we want to follow and do business with and be around. It’s inspiring. It’s what we love as a society.

I get inspired by things and sometimes I follow my instincts and go down that path. The ones that have turned out to be the most powerful are the ones where inspiration and fear come up at the same time for me. When I feel that moment where I said, “This is a great opportunity, but I probably shouldn’t do that,” that to me is a pointer. That tells me I might need to do it in order to get to the next level, whatever that may be.

That’s the moment where the inspiration and the fear hit. Most people tend to freeze up and they back off. That moment you’re talking about, those are crossroads, the trigger event and moments, the decision points in our life. I play a game whenever I hit those, and it’s the “what happens next” game. If I’m afraid of something, what happens then? I take that all the way to the end where I keep asking what happens next. What’s interesting is when I take that, and I process that whole future visioning of this fear, it ends up with me going, “I learned something. I’m smarter, stronger, and I’m able to move forward with a different sense of wisdom.” That’s what happens. It’s not anything that’s negative. It’s one of those moments of potential. You had to take it out there so that you’re not in the fog. That’s a powerful way to move past that fear and embrace the inspiration.

You’re basically saying, “What’s the worst that can happen?” I love the process that you go through. It’s such a simple thing but it’s so powerful because it brings you to the truth.

These things where we get so afraid, we go primal. We start thinking, “What if I lose my house? What if the bank takes it? What if I can’t feed myself? What would happen then?” A friend of mine had this. He went through this process. His attorney literally handed him a 50-pound bag of rice and a 50-pound bag of bean as he said, “There you go. You’re never going to starve to death.”You’re not going to starve to death, especially if you’re in a first world country. It’s not something that we should be concerned about. Do you have anybody? Can you couch surf? If we think about what we’re afraid of, it’s pretty silly when we think about it. What we’re afraid of is not having the comfort that we’ve become used to that are our norm, and we don’t want to give those up. We avoid taking the chances on ourselves to keep those comforts, not realizing that none of these things are about us dying or starving to death.

You used the word “comfort.”To entrepreneurs, that’s a dirty word. When you get comfortable, you’re absolutely in the wrong place. You started selling on eBay. You’re selling precious metals. I assume you’re selling gold coins and bullion. Is that right?

For the most part, I was selling ounces of silver that were $20 or $30 apiece. I was doing a ton of work, and on average, losing about $5 per transaction. This is a terrible business model if it was just about that, but it wasn’t about that. It was about serving people, improving not with talk and not with chatter, but with delivering and showing people that I was the one that they wanted to do business with. It was beyond price. It was beyond a sales pitch. It was because they trusted the relationship, and people saw that because I delivered consistently over and over again. That’s how I started it. We have to be willing to deliver before we get paid, and then people will only want to do business with us because people want to be in business with people that deliver, not just the cheapest person out there. The cheapest person out there is going to eventually crash and burn, but the ones that deliver are going to have a raving tribe of fans that can’t get enough of them and want to share their message.

You unraveled the small truth of the universe, which is that if you are able to offer something at a small loss and build a relationship, then riches can follow by following the path of the relationship. That’s absolutely one of the rules of the universe. Did you, in your mind, have a plan when you started to move people up the food chain and get them to purchase more and more of your precious metals offerings?

That is the idea, to continue asking the question, “How can I continue to serve you? What else can I do to make your life better? What problems can I solve?”If somebody tries one thing, they typically want to do more of that thing or other things that are in alignment. In the world of precious metals, there’s a philosophy around that. People that want that tend to be philosophically aligned with me, which is why it’s important to not sell something you hate or doesn’t resonate with you. Then there’s this connection at a deep fundamental level. I was able to continue conversations with people and continue to ask them what pain points they have.

It led into other things where I was able to solve bigger financial problems and fix businesses and fix people’s retirements and create other tools and other things that would give them a lot more power and control over their financial lives. This is a gateway. It was something that I understood and wanted to start with. I didn’t know where it was going to lead. I didn’t see the very end. I saw a bigger impact, but I didn’t know what the tools and the pieces were going to be until I started asking the questions.

I don’t think we ever know where anything is going to lead. As they say, “The best laid plans can absolutely mean nothing.” Man plans, God laughs. We have to start with a plan nonetheless because otherwise we won’t know where we’re going. Without knowing where we’re going, we only end up with chaos. You had a plan, you began selling metals on eBay even at a little bit loss, and you had quite a number of transactions. At one point, something shifted for you and you said, “It’s time to step up my game.”When was that?

About a year and a half ago, I had an epiphany. I was sitting back and I was thinking about a conversation I had with my father a few years ago. This was about seven weeks before he passed away. We were sitting down at the coffee shop, it was the last conversation we ever had. I knew that he didn’t have long. We were sitting there and he looked at me and he said, “There were so many things that I wanted to do.” I lost it. I felt regret at a cellular level. I never ever want to feel that in myself and I want to help people make sure that they can avoid that.

How do I do that? About a year and a half ago, I was sitting out in California and I thought, “I’ve got to do something bigger because I’m going to have a regret moment if I don’t go out there and impact people the way that I know I can, to lift them up and create this financial freedom through the confidence that I can help build in people.” That’s financial freedom. It’s having the confidence and believing in yourself to be able to create. That’s when I realized that I was playing small, that I wasn’t touching people in the way that I could and at the scale that I could. That’s where I went, “I’m being in a comfort zone. This is no longer okay. I need to go out there and build a team and do something that’s going to empower and free a lot more people than I’ve been doing and freeing so far.”

YFTC 005 | Financial Mentoring
Financial Mentoring: That’s financial freedom. It’s having the confidence and believing in yourself to be able to create.

What is it that you decided to do and that you’re now doing?

What I’m doing is empowering people to get off the Wall Street rollercoaster. I’m basically their co-pilot. It’s people that believe in themselves more than they do in systems and in captors. It’s a tool and it’s a process to give them the power and confidence to run their financial life, to be able to design their retirement, and not have anybody or any system threaten it or have control over it. They own it, and it doesn’t matter what happens in the markets, it doesn’t matter what happens in an election. They own their life and they’re in charge of it. That’s the bridge that I create from where they were into that space. All of a sudden there’s peace and there’s opportunity for them to live according to their design and not by default.

It sounds almost like utopia. Can you give us more details about what it is that you’re specifically talking about?

We’re taking people and we’re showing them that they can take their money out of the rollercoaster, out of the Wall Street’s system, and they’re able to hold it. They’re able to invest themselves. For a lot people, this is a very terrifying idea because they don’t feel like they’re smart enough or they have the skills or it’s too complicated. What we end up doing is we do a lot of mastery work with them to where we’re teaching them and getting them comfortable by taking them through a process of learning how to make decisions and how to have the emotional strength to continue to make decisions even when we make mistakes so that they can go out there. They don’t need to turn their stuff over to anybody, their money, their investments, and hope. It’s all about us owning things and feeling confident that we can make decisions and create anything we want. If we don’t have that confidence, then we’re screwed. That’s what we do. We help build the confidence. We’re like personal trainers in finance. Help people build their confidence muscle.

When you do this and a client gets through the process with you and is now having that confidence, do you guide them into what it is that they invest in?

What we do is we are there to teach them about things. We aren’t selling them products. We’re not saying, “Give us your money and this is a great new thing.” We’re saying, “Here are all the different things that you can do out there and tackle.”We teach them about these things. We teach them what questions to ask, and then we give them ways to get started in things to where they can go out there and make those decisions. It’s very different from most of the financial advisory world because we’re not trying to keep their money trapped inside of our system. It’s free and they’re in control of it in their own system. We’re co-pilot, we’re the navigator. We’re not the one that’s flying their plane. We’re there in the back hoping that the plane doesn’t crash or run out of gas. We’re literally the navigator and co-pilot right with them the entire way through. They’re flying. They’re choosing the flight path. They’re deciding when that thing’s going to fly and when it’s going to touchdown.

Do you have someone in your past that you went through this process with, maybe some of the first few people you took through this, and what was the result?

I have some clients that came to me and they were referred over by someone else. They said, “You need to talk to Damion about what he’s doing with his financial teaching and the stuff he’s doing.” They called me in and they said, “We were told to talk with you.” I said, “What do you want to talk about?” This is before I started spending a lot of time building people’s financial muscles. They said “We’ve got this problem. We feel like every time we look at the news, we watch the end of the report and there’s this moment where they talk about the markets did this and there’s this green arrow that goes up this red arrow that goes down. We feel like we’re on this rollercoaster.” I said, “How can I help you?” They said, “We want to get off that rollercoaster. We want that to stop.”

That was all they have known. They’re in their 50s, and this is what they had been used to and this is what they were told to do for generations. We spent the next year getting them comfortable with the alternative, that they could be in control and be responsible, and had them start looking at alternatives, things like real estate, things like private equity, things that were out there that they could pull the trigger on, that they could be in charge of. That first year, they started dipping their toes and they started doing things where they were in charge of their own investments. They had stubbed their toe a bit, and they learned, “This isn’t going to kill me.”They got stronger and their confidence started building, and then they started doing more deals. In about a year into it, the markets had fallen one day and I said, “Did you see that the markets fell?” They said, “No, we didn’t notice. We’re doing our own thing. We don’t give a crap what’s happening with the stock market.” I said, “How’s that feel?” They said, “Peaceful.”

I know that the audience is probably thinking, “I wish I could do that. I wish I had that confidence or that experience.” How could someone get a hold of you or at least get a better idea of what you do?

The work that I’ve done, the inner work, and basically any work I do, I end up writing about it because I want to share that. Anything that’s resonating with people, whether it’s the metals or whether it’s the story, and they want to shift something, there’s a book. I’ve got five books that are out there on these different things and people can read those things or they can see the commentary that I write about. When I have things I’m thinking about, I tend to be very open. I tend to think and speak at the same time. I don’t think a lot and then speak, so whatever is on my mind is out there on my site. I’m sharing that with people because I want them to know what I’m thinking. I don’t keep that to myself. I’m stealing from people if I don’t share these things because there’s a lot of wisdom that doesn’t get shared. People are too politically correct, and they don’t want people to judge them.

I am fully aware that there are people that judge me. There are haters. The more people that hate me is good because it means that I’m sending a message out there that isn’t just all sanitized. It’s raw, it’s uncut, and there are plenty where people that go, “This is going to be helpful to me.”People can find me, they can follow me, they can reach out. I love when I get the random person that reaches out and says, “Here’s my story. I need some help. What do I do? Can you give me some advice?” It is one of the coolest parts about showing up and having a voice out there that the people can listen. That’s one of the best things that happened over the last five years. The random person in Omaha that reaches out literally changed my life. And I hope it’s changing theirs too.

If this has inspired you, if you feel driven to reach out to Damion or to understand his work, go out and get his books. Go look him up on Amazon, and get a feel for this guy. He’s entrepreneur 3.0. Before I let you go, I have a grand finale question I ask every single person who’s on my show. It’s the “change the world” question. What is it that you are doing or would like to do that truly has the potential to literally change the world?

The thing that I would wish on the country and my focus is to shift society and people into that place of self-responsibility and shift away from being victims and blaming and justifying things. With that focus, by the teaching that I’m doing and the message that I have, the message of hope and possibility by shifting people’s psyche and shifting their personal philosophy into self-responsibility, everything changes. It stops being about, “How is somebody going to fix it for me?” It’s, “How am I going to get off my butt?” Do it today. I am going to do it. By shifting people and making them aware that this is possible, by delivering the confidence, everything changes. The world changes. That is the mission.

Damion Lupo, thank you so much for your time. Go take a look and find out what Damion has done and learn from his wisdom. Thank you, Damion. We’ll talk again soon.

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