Damion Lupo / CEO. Entrepreneur. Author

From Homeless to Nine Figures: What Damion Lupo Learned the Hard Way

Damion Lupo isn’t your average entrepreneur. With over 70 companies under his belt and multiple 9-figure ventures, he’s built wealth, lost it all, and built again—stronger.

In this episode, Damion dives deep into what makes or breaks a business. He shares how chasing money nearly destroyed him, why trust is the fastest path to scale, and how embracing failure is the secret to reinvention. 

His framework? 

Solve real problems, hire the best, focus obsessively, and never stop learning.

Whether you’re in your first year of business or bouncing back from burnout, Damion’s story proves that reinvention isn’t just possible—it’s powerful.

Guest Bio:

Damion Lupo is a lifelong entrepreneur who has founded over 70 businesses across multiple industries, from real estate and finance to construction and retirement planning. A bestselling author of 12 books, he is the creator of the EQRP®—an innovative self-directed retirement solution—and the co-founder of FrameTec, a tech-driven company revolutionizing home construction. After losing a $25M portfolio and experiencing homelessness, Damion rebuilt his life with a mission-driven mindset, helping others break free from financial slavery and build lasting freedom.

Link: turnkeyretirement.com

Paul Povolni, the founder of Voppa Creative, has been a creative leader for over 30 years, with clients around the world. He’s led teams in creating award-winning branding and design as well as equipping his clients to lead with Clarity, Creativity and Culture.

Headsmack Website

Transcript

Paul Povolni (01:42.801)
Hey, welcome to the Headsmack podcast. name is Paul Povolni and I am excited to have another misfit with me. I have Damian Lupo. He is a seasoned entrepreneur who has launched and grown over 70 companies from zero to 100 million throughout a remarkable 25 year journey. In addition to being a prolific author with 12 published books, Damian is celebrated for his extraordinary achievements in building multiple companies from the ground up, many of which have reached seven, eight, and even nine figure.

Valuations. Damien, how you doing,

Damion Lupo (02:13.855)
I'm doing awesome, Paul. It's great to be here.

Paul Povolni (02:15.909)
Yeah, I'm excited about this conversation. Looking forward to hearing about starting and launching 70 companies, man. That's, crazy. some people are struggling with their first and second and third, and you're, you're hit 70s. So that's amazing.

Damion Lupo (02:30.838)
It's funny because this was not the plan. When I started out, I was like, I'm going to make a few bucks and I don't like having a boss. Then I realized every customer is your boss and learned some of the lessons, the naivety when you first start. Over time, there's this incredible thing that happens if you're willing to dive into things and then quit when it doesn't work and do the next thing. You end up stair-stepping on top of each other and leveraging all these different businesses. They're like different PhD programs. Every one is so...

Paul Povolni (02:33.725)
Hahaha

Paul Povolni (02:59.182)
Right, right.

Damion Lupo (02:59.246)
Apparently I'm the most credentialed person on earth with all these damn failures.

Paul Povolni (03:02.781)
So I'd like to start this off by hearing a little bit about your origin story. How does somebody get to the point where they are launching successful businesses? So you can go as far back as you want to go, but let me hear a little bit about your origin story.

Damion Lupo (03:17.038)
The one that pops up that I remember was when I was about 11 and I was told we didn't have any money, we were broke. it was the time in life when boys wanted to play video games. And I think that that's actually kind of the whole life now. But back then in the eighties, it was a video game thing. We didn't have any money. I was told we were broke. And I said, I don't like that answer. So I went out and figured out how to create a business around buying big bundles of games from people that were bored with them, played what I wanted to, got sick of them, and then sold them.

Paul Povolni (03:30.506)
Ha

Damion Lupo (03:45.806)
And so I ended up with a wholesale retail business and it was really, started because there was a problem. It was a problem that I had and I, and and as an entrepreneur, we can't help, but to see problems everywhere. And we see all these problems as opportunities and we become obsessed about them. So it was started off with Super Mario Brothers and it ended up in construction here 35 years later.

Paul Povolni (03:51.195)
Yeah.

Paul Povolni (04:03.645)
So where did you learn that model? Where did you learn that model of buying and reselling? You you said you'd work up, parents telling you you're broke. Like what, who modeled that or what gave you that idea?

Damion Lupo (04:16.538)
I bet that there was some type of thinking that with watching my dad who was always buying and selling things, that's what he did. He had a little pawn shop, sold gold and silver back in the 70s. There was some thinking that he had. He was always buying and selling things. I probably picked up a little bit of that and thought, if you can buy it at a cheaper price, how do you get a cheaper price? You buy more. I must have got that lesson somewhere. That's pretty typical in almost every business in the world.

Paul Povolni (04:27.513)
okay.

Paul Povolni (04:39.92)
Yeah.

Paul Povolni (04:45.883)
Yeah. what, after you successfully, did the game, game, entrepreneur thing, that was your first business, I'm guessing. so where did that lead to? What was the next step for you? What was the next phase?

Damion Lupo (04:57.614)
Well, it's funny because it led to other things. I was always hustling, but it was mostly just working. was like freelancing, self-employed. I had a car detailing business that was business of Damien, Damien cleaning cars. These businesses were, they were really jobs. What was interesting is I remember when I was 18, I got excited. had sold my car, the money I made with the video games, and I put it into a stock market account. I thought, oh, this is great. I got a tip from somebody.

Paul Povolni (05:11.611)
Ha ha.

Damion Lupo (05:26.958)
put all my money, $10,000 into a stock and watched it go to lose 97 % of its value. And that was the first of four times that I lost all my money. And I thought, huh, interesting. So if you ever hear me talking about a great stock tip, you should short it. You should sell the opposite because you will make money. I am the world's worst trader. I mean, it's just not my skill set. So it was business. I was meant to go and I kept starting businesses, whether it was an insurance agency.

Paul Povolni (05:32.952)
no.

Paul Povolni (05:40.665)
Yeah.

Damion Lupo (05:52.424)
or a bookstore on campus. I got thrown out of college because I started a bookstore and put the other bookstore out of business, made paid for school. It was great though. I paid for school the week and they, they, they excused me from school. They said, you cannot be here. You're, you're running a illegal business. And I thought, well, that's great though. Cause it worked. So they just, was these problems. It was a constant, there's a problem out there. led to real estate where I was, I was helping finance houses for people.

Paul Povolni (05:58.602)
wow.

Paul Povolni (06:08.07)
wow.

Damion Lupo (06:18.434)
because banks don't like people that don't fit in a box. And I just thought, well, I could do better than a bank. And if you're creative, you really can do better than almost any institutional system, but you got to be willing to hustle. so that it was just like, there was a whole variety of different businesses and each one taught me something useful. And then I leveraged that and it kind of continued from there.

Paul Povolni (06:39.399)
So it sounds like it wasn't even one business that you continued on and kept evolving that business. seemed like you found problems and solved it. Is that what piqued your interest in those different businesses alone or was there something else about that particular business that interested you?

Damion Lupo (06:58.006)
Well, so when I had an insurance agency, it seemed too small. And here's what I mean by that. I started, I was one of the youngest agents in history. It was still in my teens. I wasn't even 20 yet. And I started this thing and I was introduced to the guys that there was a guy in Phoenix, Arizona that was making a million plus a year take home. And I looked at that guy and he'd been around for about 20 years. And I thought, that's not enough money. Now keep in mind at the time I'm making like 20 grand a year, barely. I mean, I'm starving to death.

Paul Povolni (07:10.113)
wow.

Paul Povolni (07:25.264)
Yeah, yeah.

Damion Lupo (07:26.542)
But a million a year wasn't enough. So after 18 months, I sold my book of business for about $20,000. And I went after real estate. And I did it at the time mostly because I saw an opportunity to make money, which was one of my great mistakes. There wasn't another mission. There wasn't another purpose beyond just the money. And I made a ton of money because I followed what people told me to do at seminars. And I made millions and millions of dollars. And then I lost 25 million and only had 20 in 2008. So that was one of the great

resets, if you will, that happened because I didn't understand the philosophy of mission and vision. It was only about the money. So greed was one of those lessons that I had to go through and understand. And understand it has to be about more than just me and my hedonistic tendencies, which I was really good at.

Paul Povolni (08:13.175)
So greed was one lesson that you learned, you know, obviously, you know, moving from, from one type of industry to another type of industry, to another type of industry, there's always things that you can kind of learn along the way that prepare you for the next thing. And, and, and this happens a lot. And Steve jobs, you've been talked about in a speech about we, we connect the dots backwards. So, so do you see in, as you've moved from this business to business, this different type of business, different type of business, what kind of lessons did you learn along the way?

from one business either succeeding or failing, moving to the next business.

Damion Lupo (08:47.72)
I'm glad you brought that up because there's a pro and a con to moving around between industries. One, you lose the momentum of that industry. So like our chief operating officer here at FrameTech has been bleeding sawdust since he was eight. And so he knows virtually everything and he's forgotten more than most of us will ever learn. And so there's an incredible value where you're not getting in at the end of the line every time you bounce to something new. On the other hand, what I've done is had...

Paul Povolni (09:01.148)
You

Damion Lupo (09:14.796)
a couple dozen different industries that I've been in. So I see things from different vantage points, different angles, different lenses. And what happens is I bring in, you you go to a brewery convention, and then you come back to a construction company, and you go, I got some ideas, and nobody's ever heard of any of this stuff, because we tend to be in a silo just talking to people that think like us. So there's this incredible value by leveraging other industries. And that's one of the things that's come up, I show up at meetings, and I've done things, been in places that don't sound anything like what we're that's the place I'm in now.

Paul Povolni (09:30.907)
Right, right.

Damion Lupo (09:44.236)
And so can look at problems completely different and it adds an incredible value to have people that have had a variety. it's, you know, it's literally dozens of industries with unbelievable amounts of problems that come in all walks of and in shapes. so that's, I see the value in both of those. And, and ultimately when it comes down to it, there's a lot of similarity amongst any everything because business is business. has to do with people. has to do with psychology. has to do with emotion. has to do with problems. And

There are principles that if you understand them in one industry, they apply to every other industry.

Paul Povolni (10:18.161)
So what was one thing that you found as a common pattern or a thread between the success of the ones that worked for you?

Damion Lupo (10:27.278)
One of the funniest mistakes I made in the beginning was saying, what can I afford to pay somebody? And so I would literally say, okay, I can afford $10 an hour. This is now granted, this is 25 years ago. But it was a fallacy and I ended up getting a $10 an hour type of person and that person was terrible. And so I ended up with a terrible business. And what I've learned is that you absolutely go, you hire the best people and you get people before you think you can afford them because great people that quote unquote cost a lot of money.

Paul Povolni (10:45.021)
Ha

Damion Lupo (10:57.09)
don't cost you anything, they make you a ton. And if you have people that are affordable, they will cost you a ton of money in turnover, in their inadequate skills, in their terrible attitudes. It's unbelievable. And now it's literally who can we find or poach that's the best in class? And you bring them on and you figure it out. And when that happens, that's just one of those pinheaded amateur naive things that we do because we were asking the wrong question and we don't even know we're asking the wrong question.

until later you go, man, that's stupid, but you don't know better, because you don't know what you don't know, and so you just kind of go around and do it, and then you learn later.

Paul Povolni (11:29.149)
Right, right, right.

Yeah. So with the businesses, you know, with the 70 businesses that you've worked on, I'm sure some of those, you know, failed, maybe they didn't, maybe they were a hundred percent success, but the other ones that failed, which one do you think that you could go back now and do better or which is one that you would like totally stay away from and you'll never touch again.

Damion Lupo (11:53.078)
Well, it's funny because when I did the real estate business, which, there's real estate and real estate, it's never going to go away because people have to live somewhere, especially when you're talking about residential. I did that and it was on a shoestring. was grinding. was under-capitalized. I was understaffed. I was under-visioned. I wrote a book on it in 2004 called Maverick Mistakes in Real Estate Investing. The first million I lost. It was really funny. That book was literally, here are all the things that I did wrong that I would do different.

And like one of them was I was all over, I was investing all over Phoenix. And that may seem like, that's good. That's only in one city. No, it was like, it took me eight hours to go from corner to corner and literally hit everything. And then I started spreading out all over the United States. being scattered, not focused is one of those things that, you you can make a billion dollars in any industry, virtually any place in the world or whatever your goal is. It's usually too small, but there's no limit. What we tend to do is say, well,

it's acres of diamonds. The diamonds are right under our feet, but we go, I'm going to go over the fence and go find them over there. And that's a huge mistake instead of just drilling and grinding and continuing. being a farmer, instead of being a hunter chasing an elk all over creation, you literally go and you start farming and all of a sudden you have these orchards full of diamonds.

Paul Povolni (13:08.413)
So is the focus the element that you started bringing in to all your businesses and that's what made the difference or was there something else?

Damion Lupo (13:16.77)
Yeah, that was one of the elements and coming in and saying, okay, I'm going to focus. 12, 13 years ago when I launched a company called EQRP to help people with self-directed retirement accounts, I did that, but I also had other things that I was doing. And it wasn't until I said, okay, I'm not doing the other things. I'm only focusing on this. And when I was doing podcasts, when I was speaking, I became known as the guy. I was the self-directed guy. created my own class, my own language. And that's what people thought about. And there was a direct connection to the brand.

And it wasn't because if somebody says, hey, you know what? know Damien and he has 15 different things and he started all of them in the last year. They're not going to come to me for anything because they don't trust me for anything. But I wrote the book on the thing. ultimately that led into other businesses that were good bolt-ons and it becomes a flywheel. But there's a time and a place for adding more elements. Jeff Bezos is a perfect example. It was books and that's it. And now it's everything. But he didn't start with everything. He started with the one thing that gave him traction. so that was one of the switches. I went and focused on the thing.

And that evolved over time into more of a package, a suite of things that were focused on one mission. And the mission is to create financial freedom with people and break their financial shackles. Because I think money is the modern day slavery. so everything that I'm doing is finding a way to give people more freedom from money being their master.

Paul Povolni (14:35.153)
Wow. so, you know, focus was obviously a very good lesson. What other lessons did you bring out of, you know, starting those companies, you know, succeeding, failing, maybe not, growing as much and others that just boomed. were some other lessons that came out of that?

Damion Lupo (14:51.168)
Money can make you stupid and it generally does. people that have a lot of money, it's like when founders, and I've done this myself, where you raise a bunch of money for things and then you start buying foosball tables and big kombucha kegs and you're not actually selling anything, but this is what people do. And you think, I got all this money. And then the money goes away really fast. And so that's one problem. Money makes you stupid. And it turns off the creative juices. In the beginning, when I was doing real estate, I had no money. I had to finance.

Paul Povolni (14:53.415)
you

Paul Povolni (15:11.782)
Yeah.

Damion Lupo (15:20.014)
I literally bought my first house, my first rental house, using a cash advance on a credit card. And that's because I had to be creative. But it's also really hard. what you need is you need the wisdom to know how to spend money. And then you need capital because if you don't have any capital, it's really hard to go do things when you have $0. Everybody looks at you and they go, here, OK, we're going to need $10,000 or $100,000 or a million. And you're like, well, can you just finance everything because I have nothing? So being undercapitalized is one of those things.

Paul Povolni (15:25.586)
Bye.

Damion Lupo (15:47.5)
The problem is if you don't have the experience and the wisdom and the patience, you'll tend to buy too many foosball tables.

Paul Povolni (15:53.701)
Yeah, yeah, yeah. It's, easy to get distracted, when, when things are like that. And so, you know, with, with that being, you know, another big lesson for you, you know, talk about, you know, building, building trust, because, you know, when you, when you, when you, as you mentioned earlier, you know, having 15 different things that you do and kind of being all over the place at first, without the focus, talk about the building trust through, through something like service and through,

know, honesty and how that has impacted your business.

Damion Lupo (16:25.518)
So there's a great book called The Business of Speed to Trust by Covey. And it's a philosophy that when you embrace it and you give it time, there's nothing more powerful in terms of marketing than trust that you build in the relationships. So for example, it seems like this amazing story that the company that I'm one of the founders of and it's most of my focus is FrameTech. And we've raised $103 million from individuals, not banks, not institutions, but just individuals. And that came

one person at a time, hundreds of people. Why did they do that? Because relationships were built over time and people say, well, how do you go raise money? And I go, you serve people seven days a week, 24 hours a day for years. And you do things to where they go, yeah, I can count on you. I know you. This like no trust, this whole thing, that you don't do that overnight. People think that there's this immediate process where if they hear your voice, they see you on stage, yeah, they'll know you. They might like you.

Paul Povolni (17:13.692)
Right. Right.

Damion Lupo (17:19.234)
But the trust isn't that deep. It's surface level until the next speaker comes up or the next podcast happens. And then they're, ooh, they like that person. They trust them. So it does take time. And that's the secret sauce. When you have trust, not only with investors or customers, but with teams, like the teams that I have now, there's so much trust because of the integrity and the intelligence and the work ethic. So the people that I'm around, I don't feel like I have to go in. And what's happening is the information flows very rapidly and fast.

Paul Povolni (17:25.779)
Hahaha.

Damion Lupo (17:48.95)
At the same time, if I'm gone for a week and a whole bunch of decisions are made, which they are every week and every day, I have 100 % confidence. And so we move at the speed of light and the same thing in reverse. And that's a difference when you have a world-class team. You work at the speed of light. And when you have a world-class investor and a customer, like when you have those relationships that are based on trust, everything is easier. And people go, well, my business is so hard. I go, cause you don't have enough trust.

Paul Povolni (18:16.539)
Yeah. So what does trust look like in like a day to day? Like let's, let's bring it down to ground level of, you know, when, when you're talking about a business and the day to day activities, what are some things that, you do or you don't do to build that trust?

Damion Lupo (18:32.974)
Well, one is you've got to be the best. If you're just lukewarm average, nobody's going to really trust you. want the best. Now, there a lot of people that are looking for average and they want the cheapest. You don't want those people anyway. You want the people that actually value, value, that they value intelligence, they value whatever it is, whether it's food or pencils or you're selling housing or you're a stockbroker, it doesn't matter. You got to be really, really smart. so that means you study. like Friday night, is Damien out there?

what is he doing? For the last 30 years, I've been out there, I'll be at a bar studying, I'll be at a restaurant studying. Like I'm always studying and writing books. so whatever it is you're doing, become world class. And then people will look at you as an authority. And then you deliver. And instead of asking you for something, you ask, how can I deliver? What is the problem? And so when you become known as the person that's solving problems, and I learned this stuff from Jim Rohn 35 years ago, when I was studying him, who's literally like the

the OG of personal development. That's where Tony Robbins got a lot of his stuff. it's really true. You're always asking, what can I do? Not from nine to five, the other 148 hours a week. You're figuring out, okay, when somebody has a problem on Saturday night at 9pm, you're their person. Like you become the mayor that knows everything and how to connect them and how to solve problems. That's what you do. And then eventually people are just like, I want to work with you. want to do...

But people get it backwards. literally look at a fireplace and they go, you know what, give me heat and I'll go put some wood in you. That's not how it works. You got to go grow the tree, cut the tree down, let it dry. There's a whole process to this and then you get the heat. But people, they're impatient. if you understand the process and you're at ground level, it's about becoming an authority in whatever you're doing. And you can, as an employee, as a business owner, as whatever you're doing, become world class and then give. And what's interesting is people cannot wait.

Paul Povolni (20:01.1)
Hahaha

Damion Lupo (20:24.472)
to do things with you when that's how you show up.

Paul Povolni (20:27.665)
That's amazing. And so you've, you've mentioned several authors and several books. And of course you started off with your origin story sharing about, you know, that, that your dad kind of influenced you probably early on in your first business. What are some other, you know, guides or people that have kind of helped you along the way? and like, what is the importance of seeking that guidance? Because, you know, we try and maverick it out. You would try and learn, it out and do it.

Talk about the guidance that has kind of helped you in successfully having these 70 businesses and making as much as you have.

Damion Lupo (21:01.656)
Well, one thing that's interesting is people can be, they can be guides, they can be examples, they can also be warnings. So I look at my dad as an example, and he was a guide in some things and an absolute warning in other ones. And one of the ways that he was very cheap. And unfortunately, people that are cheap, you're not going to create wealth or freedom being cheap. You might end up dying with a bunch of money, but that doesn't, like, what's the purpose? And so that's something that's really important. Get everything you can out of the people that are around you and

Paul Povolni (21:07.697)
you

Paul Povolni (21:24.87)
Yeah.

Damion Lupo (21:30.996)
And I look, everybody's got these, they've got things to teach us. And sometimes you have to know when to stop learning from people. have to say, okay, I'm going to back off and stop absorbing them. Because if you're around people, like I used to listen to Tony Robbins constantly and other mentors, and I see you start sounding like them. speak there, like you absorb, just like if you immerse yourself in Spain, you're going to start speaking Spanish. You're going to like, this is what happens. It's an immersion program.

Paul Povolni (21:39.005)
Ha

Damion Lupo (21:57.082)
I spent some time with Peter Diamandis and really spent a lot of time listening to him. He wrote the book Abundance and Bold. He created the X Prize. It's that philosophy. don't under... Excarcity and Malthusian economics where there's a lack does not make any sense to me because it's a lie. And so, the opposite is Peter. And so, I spend time listening to people like that and I think like that. so, when I'm thinking about a vision for the future, it doesn't involve lack. It doesn't involve finite anything.

And so it's being around that kind of stuff. And I always say that if you want to change your life, the first question is, what is your environment? You can hack that. That's the greatest hack. Just ask yourself, who are the people that are around you influencing you? Because you're going to be them. Like that saying, you're going to be the average of the five people in every way, financially, health-wise, abundance-wise, integrity. If you have a bunch of lying, cheating a-holes, you're going to become one. If that's who's in your world, so ask yourself the hard questions.

Paul Povolni (22:38.289)
Right.

Paul Povolni (22:49.116)
Right, right.

Damion Lupo (22:52.588)
and then bring some new people in. You don't have to fire everybody in your life. I mean, I've done that, but you do need some influences. so it's, think being real about that as opposed to just saying, okay, I really like so and so. Ask who's influencing you now, because that is your future if you keep doing the same thing, meaning you're around the same people.

Paul Povolni (23:10.267)
Right, right. I absolutely love that. Cause yeah, it does, it does make a difference. And we do start, you know, imitating, the, people that we see as the most influential in our life or the most powerful or the most successful or that we want to be like, but at some point you've got to find your own voice. know, you've got to find who you are. And I've, sometimes said that, you know, until you find your own voice, be a really, really good echo, you know, but at some point you've got to find your own voice. because, know, you, you, you,

find your path that way, you find your desires, your passions, your place of success, right?

Damion Lupo (23:46.164)
I think you hit on something that's really, really important. And one of the things I see happening, so I'll give a great example. I've studied martial arts. I started 25 years ago and over a period of time. like you mimic and you do the things that you're taught and you look like their stuff. And it's not really uniquely your own. It's you're just sort of like a robot parrot. And that's great. And then eventually over time, different influences come in. And so over 20 years, I developed my own form. So I went from a keto and

different things that I'd learned and I built my own thing called Yokido, which is a blend of yoga, reiki and Aikido. And that was uniquely me. It didn't take 10 minutes or a month or a year, it took more than a decade. And that's one of the things that happens where I see a lot of people saying, hey, this is me, it's my brand. I came up with a fancy word and we call that uniquely my verbiage. And I look at them and I go, you literally came up with this over the weekend after you spent the previous weekend at a seminar learning a new thing. You might have a unique thing, but there's no depth. And so when people spend time, they spend years

You can tell when somebody is speaking to you with the depth and the breadth of experience and wisdom as opposed to I have a lot of memorized facts and I can tell you stuff with enthusiastic whatever. There's a very big difference and I have a tendency to go and kind of avoid the people that have this great new thing because guess what? Next week it's going to be another great new thing. I want people that are really deep. Those are the people that are really interesting to me.

Paul Povolni (25:04.154)
Yeah.

Paul Povolni (25:08.401)
Yeah. And so with these skills that you've gathered, you know, over, over launching the businesses that you have, what was the skill that is the most constant and maybe we've already covered it, but what do you feel is the most, the skill that's been the most constant that took you maybe to your first million and then beyond.

Damion Lupo (25:25.024)
It's selling. mean, being able to sell and selling isn't about jamming anything down somebody's throat. It's literally about listening and understand how you solve a problem, their problem, not your problem. Everybody goes, I got to figure out how to make money. I'm like, that's your problem. Nobody cares. What they're trying to figure out is how are going to solve their problem? How are you going to solve their problem? And it's also the highest paid thing in the world. I mean, any CEO for a major company knows how to sell. They can sell themselves. They can sell their company, their products and people. What's the dumbest thing I've ever heard.

Paul Povolni (25:38.652)
Yeah.

Damion Lupo (25:54.802)
is one of the dumbest things is I don't sell. Like you hear a lot of dumb things. Like I hear a lot of dumb things out of my mouth. I listened to me 20 years ago or 10 years ago and I go, God, that's me. But the idea of selling, understanding how to sell, it's really about you listening and building relationships. That's what selling is. And when you focus on that, you become world class, you literally write your own ticket. And here's one of the coolest things.

If you get mowed over by something that you can't control, like 2008, nobody can really control that. Like when the market fell on everybody's head and wiped them out, the people that were able to go through that and jump out and just keep running were the ones that had skills, and especially in sales, where you can go and doesn't matter, you can drop anywhere in the world at any point in time. If you can sell, you're going to be fine. And then you have this freedom because it doesn't matter if somebody takes everything away from you, you still have your ability.

Paul Povolni (26:27.515)
Right.

Paul Povolni (26:47.165)
Yeah. So, you know, a lot of people, they do feel that way about sales. You know, I don't, I'm not a sales person. I don't like doing sales. So how do you help them to get over that? Because, you know, for some people it seems natural. They're just, they can sell anything for others. It's, know, that maybe they're introverted. Maybe they've never done it. What are some of the things that you can encourage them or help them or, or train them in to help them with that sales, like getting on a call or a cold calling or whatever it might be.

Damion Lupo (27:15.96)
So there's two things, and I referenced the one in terms of becoming world class. So know your thing. If you think it's about memorizing something and then knowing exactly how to trick somebody into signing on the dotted line, you're missing the point of sales. Sales is about becoming great at whatever it is and knowledgeable, and it's also asking questions. When people are in sales, you'll find that the people that are selling the most spend the least amount of time talking. They ask questions and they take notes, and then people feel heard.

and they're more likely to say yes, and they sell themselves. So how do you become great? How do you become awesome at selling? You literally just you study your craft, you study and it's the thing that you're in. And then that does take time and people everybody's looking for the hack. How do I do this overnight? How do I make a ton of money? Well, you start off making no money. You start off where nobody wants to talk to you because you literally are an idiot. And look, I know what it's like. I started off as an idiot in many different fields, knowing nothing, don't know the language, don't know what to say. And you know what you do? You shut up.

Paul Povolni (28:04.696)
Ha ha.

Damion Lupo (28:16.054)
And your job is to go find the smartest person and attach yourself like human superglue and then absorb everything. then keep asking questions. Like being a kid where you're curious, you're always asking questions, that's where we have to get back to. If you get back to that point, whether you're learning your craft or whether you're figuring out what your customer or potential customer wants, it's about being curious. Being curious is like the superhero power that people have lost. Somehow it just disappears after like age seven.

Paul Povolni (28:21.885)
Yeah.

Damion Lupo (28:45.526)
stop being curious because you're told to shut up. That needs to come back.

Paul Povolni (28:47.803)
Right. Right. And so, you know, one, one of your lessons that you talk about, or one of the things that you talk about is the baseball and business metaphor. So talk about that little bit. Why is a strikeout necessary to take you a step closer to a home run?

Damion Lupo (29:04.866)
Well, I always look at it when we think about how we're taught as kids, we're taught that you're supposed to have 80, 90, 100%. Like if you have 50 or 60%, you're a failure. And they literally throw you out. They say, go, be homeless, you're a loser. And when you think about the real world, it's the exact opposite. You go in and you swing and you have to strike out. And the people that strike out seven or eight times out of 10,

You're talking 70, 80 % failure rate, if you will, the way we've been taught. Those are the people that are making 10, 20, $30 million a year. They're Hall of Famers. They're the best in the world because they fail the most. I mean, it's crazy to think about that. Same thing in business. When you're in business, like I've had these companies, I've had 70, 80 % of them that didn't work, but they taught me a ton. Just like those strikeouts, they teach you. What do the best players in every sport do? They watch game tape.

Paul Povolni (29:43.386)
Yeah.

Damion Lupo (29:58.988)
they study, they don't just study the wins, they study how all the things that fail and they get better. And they celebrate the wins for about five minutes, every world class performer, and then they go on and they keep studying, they keep practicing. It's the same thing in business. when you embrace that, when you get comfortable with it, one of the best ways to do that is to get a cold plunge. You embrace the pain, you're like, okay, I'm gonna go strike out and it's gonna hurt and you do it every morning. And everything else is easy. You're like, I can do that.

Paul Povolni (30:25.021)
Yeah.

Damion Lupo (30:27.234)
having a practice around something that's hard and painful, I mean, let's be real, striking out does not feel good in the moment. But when you really embrace what that means to your life, you go, man, I can't wait to strike out. I can't wait to sit there and have everything tingle because it hurts. This becomes the way that you live and it's why you end up winning.

Paul Povolni (30:41.84)
Right.

Paul Povolni (30:46.663)
So talk a little bit about that mindset around failure, because it is a mindset that I think has a lot of people paralyzed. They are afraid to fail, whether it's afraid of not being perfect, whether it's a fear of disappointment. How do you get over that mindset or that fear of failure, because it is so paralyzing?

Damion Lupo (31:11.506)
This goes to there's a judgment factor. We want to be liked. It's a tribal instinct. It's very primal. We want to be a part of a tribe because if you're by yourself, you're more likely to be eaten by something. This is hardwired into our psyche. mean, no joke. It's like that's we've had that when I was growing up in Alaska, when I was out by myself, throwing trash out in the Arctic Circle, I literally was trying to avoid being eaten by polar bear. I mean, this was my daily routine. So that's what people think. They're like, man, if I'm out there and I make a mistake and I get judged, I'm going to be eaten by something.

Paul Povolni (31:33.264)
wow.

Damion Lupo (31:41.166)
It couldn't be further from the truth, but it holds us back. And so we try to fit in. And I've watched people that are, it's actually pathetic when they're out trying to get social validation. And so they constantly are looking around and saying, okay, what do people think about me? I had a mentor years ago that said, you have no idea how much freedom you'll have until you stop caring what other people think about you. When you stop, when you get completely done with that, there's this intense freedom that you can move freely without constantly looking around.

And honestly, nobody gives a crap. don't care. They're too busy focused on themselves. But we give all this power away to other people simply so that they look at us. And how do you start changing that? One is you get around people that are different. You get people and you find your way into groups and places where people are celebrating your wins and your losses. And they're like, that's awesome. Cool.

like all the things that you do, not just the wins, not just because you got a new car, not just because you have a new trophy wife. There's literally people that are out there. When it becomes neutral, you're like, it doesn't matter what I do. That's an empowering thing when you flop and somebody is like, sweet. You're like, what? You don't think I'm a loser? They're like, that's awesome. Those are the type of people that everybody needs in their life because it'll propel you forward.

Paul Povolni (32:43.794)
Yeah.

Paul Povolni (32:50.791)
Yeah.

Paul Povolni (32:57.371)
Now, did any of the businesses that you started set you back like that you maybe failed at that set you back and what did you do to get over it?

Damion Lupo (33:07.957)
I would say a majority of them set me back. They put me back on my heels. Sometimes they knocked me on my face and ran over me with the train. So I all the different experiences. The biggest one that set me back the longest and the most was in 2008 when I lost the 25 million was homeless, negative. literally couldn't, American Express declined me buying toilet paper at Costco. It was a pretty bad experience.

Paul Povolni (33:15.485)
You

Paul Povolni (33:32.902)
Yeah.

Damion Lupo (33:33.806)
That's with the black card, by the way. If you've had a black card or you know about them, it's like an unlimited, you can buy a jet. At that time, everything was so bad, AmEx said, no toilet paper. I was like, okay, this sucks. The biggest problem there is it broke my confidence. After going through that, it took years for me to get to the point where I was willing to look at anything because I was so scared of the pain. I was just looking over my shoulder and the shadows. It took

Paul Povolni (33:49.489)
Yeah, yeah.

Damion Lupo (34:01.266)
The way to get through that, and this is one of the mistakes that I won't make again, I isolated myself. I didn't want to talk about it. so ultimately I found a guy that ended up doing martial arts with him. He was my therapist for a couple of years before he fired me. And he said, you're done. You've done the work. You did 20 years of work in two years. Like you're done. And I said, wow, weird. I just got fired by my therapist. But that's what I would do. If you're stuck, you need a coach. You need a coach that's going to tell you the truth. You need to pay somebody.

Paul Povolni (34:07.677)
Hmm.

Paul Povolni (34:24.071)
Ha ha ha.

Damion Lupo (34:30.798)
Go in and talk to your neighbor or your friend, they're not going to tell you the truth because they're going to love on you. You need somebody that's paid to tell you the truth that you'll respect enough to take the action. That's what I would have done if I was going back, I would have always had that person. I have a mentor now, I have a mastermind and it's full of people that these are people that are beyond me where I'm at. They're smarter, they're more sophisticated, they're wealthier, they're fitter. It's a North Star in a lot of ways.

Paul Povolni (34:54.237)
Hmm.

Damion Lupo (34:56.31)
And that's something everybody should have. And it's very rare to say everybody should, because then end up shitting all over people and nobody likes that. It's really important to have these things because the influence and it gives you something so you're not lost. When you are lost, you can ask the question and people have wisdom. They don't just have something they read on TikTok, or I guess watched on TikTok. They actually have experience and that is a game changer.

Paul Povolni (35:16.701)
Yeah.

So, you know, you're homeless, you're trying to buy toilet paper at Costco. What was the first win that helped flip your mindset?

Damion Lupo (35:33.134)
I think the biggest win was the work I did with Frank when we asked the question over those two years. And the question was, what is true? And I wrote a book, another book called Reinvented Life. And it was based on that experience of studying literally one question for two years and going deeper and deeper. And the big win was acknowledging the truth. And it was ugly when I looked back.

Paul Povolni (35:53.799)
Yeah.

Damion Lupo (35:54.548)
It was ugly and ugly and uglier as I got deeper because I realized, yikes, I had to go through a lot of dark stuff. The question was, what is true about me? What do I believe? Who am I? What was I doing? I realized that what I was doing for those first 10 years of life and business, it was about Damien. It was about what can I get? As much as there were other people involved, I was the primary. It was very internal. The shift on the other side of that was, how can I serve? What can I think about? What can I do that's bigger, that serves more people?

And instead of trying to figure out how to make a billion dollars, the different question was, how can I serve a billion people? And what I've learned is that when you're focused on that, it's very external. You always have to have something that's outside of you that you're working on towards for. And the money takes care of itself. People don't trust that. They go, I got to go get the money. No, you don't. You really don't. And it's not just, I've been saying this and I've lost everything a couple of times in the last 12, 15 years after I was homeless. I had to go through and learn some lessons and really embrace this

this thing and trust the universe in God that if you focus on the thing that serves other people, the money takes care of itself. We just don't believe in that enough. And once you do, it's very freeing. And then you're like, I got a different problem. I got too much money. What do do with that? it's an interesting problem. It's also a problem. I like that problem better than not enough money. Not enough money sucks.

Paul Povolni (37:07.953)
Yeah.

Paul Povolni (37:15.421)
So, so the, the, biggest lesson was serving people. And so what, what did you do first to get over that hump to, to be able to afford a toilet paper at Costco again? What, was the, business that, got you back on track?

Damion Lupo (37:30.926)
Man, I grinded my ass off. That's what I did. To get myself back on track, it wasn't some miracle. It was literally worked every day all day long. And I was finding anything and everything. And I was consulting. was again looking for problems, looking for problems that I could go in and solve. there's no lack of problems. People have problems. Everybody has problems. And when you go in there and then you start asking, what are the most valuable problems I have the ability to solve? And then you go focus on those as much as you can. So it was really doing that.

So was like this shotgun approach, I was shooting at everything and then narrowing that down and saying, okay, I'm going to go after this one thing. And it was keeping my lifestyle in check. When I blew up, I had the champagne and Ferrari lifestyle. And then I had to go back into the very meager, very humble space, which is, it kind of blows to go backwards. And it is humbling. And I remember having to call my dad.

Paul Povolni (38:15.43)
Yeah, yeah.

Paul Povolni (38:25.041)
Yeah.

Damion Lupo (38:28.142)
I guess I chose to call him and I said, can you sign on a couple of things? One, I need a place and my credit sucks. I didn't realize you could have a 400 credit score, which I did. I thought you had at least 500 if you got your name right on the application, but that's not true. And I said, I need help. Will you co-sign? And he said, yes. And I said, I also need a cell phone. Would you mind co-signing on a cell phone? I mean, I couldn't qualify for a toaster oven.

Paul Povolni (38:41.328)
Wow.

Paul Povolni (38:53.65)
Wow.

Damion Lupo (38:55.582)
That is an important process to go through because at this point, this is why I think it's tough if you just handed everything and I think parents that give their kids tons of money and everything without any pain, you're taking away the opportunity. Having the humility and having the process of going through and building something from nothing is incredibly useful when you end up with a lot of wealth. It's having that reference. If you don't have that reference, either you're an arrogant prick or you end up losing it in most cases.

Paul Povolni (39:23.101)
Yeah, and so you said you started solving problems and that kind of got you out of that dip. What problem do you solve now?

Damion Lupo (39:32.558)
The problem I solve now is the housing crisis, the housing problem. Houses are too expensive and there's not enough. This has been a problem for the last 15 years. After the meltdown, after 2008, a lot of trades left and there just is not enough building and the regulations are getting harder and nothing has really evolved technologically. A few years ago, when some guys came to me and said, hey, we have this idea, but we need $40 million, I thought, all right, well, it's an interesting idea.

I looked at it and then I realized I was dealing with world-class people. Because of all the stuff I'd done over the years and dealing with knuckleheads that weren't world-class, I saw these guys and said, these are the exact people that I want to be in business with, the ones I want to invest with, the ones I can trust. I said, you know what? I like the idea a lot. I really like you guys. My network, my community and I led it and said, I'm in on this. People said, we want to do it with you. We want to solve this.

So we're doing something different. We're building houses and we're doing it four times faster at the framing part, four times faster at a 10 times better quality with 99 % less waste. It's a fundamental difference in how everything is done. This is the future of framing and how house prices will drop, how we'll get more supply. So we're solving a ginormous problem. 10 million missing housing units in America right now. That's a huge problem. And it ripples into a lot of people. So can imagine if you solve a problem that big,

Wealth takes care of itself and it's deeply fulfilling. So waking up at two o'clock in the morning on fire, ready to start is not unusual.

Paul Povolni (41:06.981)
Yeah. And so talk a little bit about what that, that framing is that that is so different. Like what, what, makes it so different? What makes it so much better?

Damion Lupo (41:16.162)
Well, anytime you can build the pieces of anything. like the difference, if you were to build a car in your front yard, as opposed to in a manufacturing plant, that's you're going to have a different quality. There's just quality controls. So that's what makes it 10 times better quality. We're building all the pieces. So somebody gives us plans for a house or an apartment or a hotel, and we build each of the walls, and then we bring it out and put it together. So it's not like a whole house that we just go drop somewhere. It's literally the framing pieces.

And the way that we're doing it with this patented process, it's a material handling process, we're able to take all the wood and put it on a conveyor belt and scan it. And then we attach it end to end through a finger joiner. And then because we're doing this, we don't cut off 18 inches of every board and throw it in a dumpster. We literally are using almost all the wood. So maybe 1 % is sawdust and little miter corner cuts. The rest of it we use. So that's that part. And the speed.

Because we're doing things so efficiently in a factory with, have a lot of robots. It's the most technologically advanced type of manufacturing facility of its kind in the world. Because of that efficiency, it's four times faster. I mean, the last innovation was 1954. It was the damn nail gun. That was 70 years ago. It's crazy. But people don't, they've been milking this cow for a century. And we said, all right, time to evolve the cow. And so we've got a cow that runs on roller skates.

Paul Povolni (42:25.725)
Yeah.

Damion Lupo (42:37.632)
and it's a fast cow.

Paul Povolni (42:40.024)
That's amazing. And so what, what are you, um, very strategically doing now to avoid maybe the failures from the past? What, what, do you do on the daily or on a monthly or weekly or quarterly or whatever? What have you set in place that's saying, okay, these, these things are essential because I don't want to end up where I was 15 years ago.

Damion Lupo (43:03.982)
So it's interesting just in the way that that question is poised. One of the things that I do differently and I constantly throw it out there, like the idea of playing not to lose. I'm fine in flopping and things not working. I've done plenty of things in the last few years with FrameTech that from my seat that did not work or the company has tried things and we said, okay, that didn't work. Let's try something different. And so I think about this North Star, what I'm doing and we're going for it.

There is no, we're in a season, so I don't look at balanced life as a realistic thing for somebody that is actually wanting to live their fullest potential. I look at this as a season. And so I don't say, okay, I'm going to go take off weekends and nights like most of the population. I say, okay, whatever it takes. I've never been in the position where it's been whatever it takes. And the whole team that surrounds me is doing the same thing. That's very different. And most people are not around that. They don't live that way. And so I know that

while we're doing what we're doing right now, it's whatever it takes. And that's the only way that you win a startup game. You have to be willing to do whatever it takes 24 seven. And most people just aren't willing to do it, but they want the, they want the wins and the money and the accolades of the big thing that's successful. And I wasn't in that space. I was too busy showing off and proving to people and doing the Ferraris and all the stuff. and, and that's, that's a huge shift. Now everybody knows they trust that we are all in and

We don't really have people saying, well, you could have done more. There is not a human way for us to do more because not only are we grinding and doing, but we're asking questions and we're learning at the speed of light when we do things that flop. And then there's constant feedback because it's an open, transparent environment. businesses and historically that I've been involved with, there was a lack of trust for people to be open because they would get critical of each other and it was messy. So people would just isolate in silo and

go off and do their own thing. And I was one of them. I wasn't a good team member. I wasn't a good leader. I wasn't very good at anything. I was just learning. was, you know, was stumbling around, running into walls enthusiastically.

Paul Povolni (45:05.174)
Hahaha.

Paul Povolni (45:09.169)
Well, in that in that time that you were running into walls, you've also written 12 books. So if you could take those books in and, you know, for some reason, 11 of those didn't exist and you could only keep one and share that with people. Which one of your books would you do that with?

Damion Lupo (45:25.038)
The most recent book that I published about five years ago, I have another one that's coming out next year, but the one that I wrote called Unicornomics, and it's interesting because it's the foundational 15 % that give a business, give you an 85 % chance likelihood of success. We think about the numbers. Statistically, nine out of 10 businesses fail within five years, and then nine out of 10 that are still in existing fail over the next five years.

So in 10 years, it's 99 out of, I mean, it's terrible. what I was thinking about this, I was like, okay, well, some people, it's like everything they do seems to work. What is the difference? It's because they're working off of principles and they have rules. And so I looked back at all the things that I'd done and asked the question, which things worked, which things were consistent, which things failed, and then compared that to whether it was Apple or Exxon or whatever these companies were, what were those principles?

Paul Povolni (45:56.957)
Wow.

Damion Lupo (46:21.26)
And if you can get the upfront stuff right, like a world-class team with transparency, with the proper capital allocations, if you get all these things right upfront, 85%, that means that if you started two businesses under this framework, you are going to have a winner of some sort. And it's a mini book. So this book, it might take you an hour to read if you're slow. And it's funny because you don't need a PhD. You literally need this thing boiled down. Most books have

Paul Povolni (46:42.939)
Hahaha

Damion Lupo (46:48.878)
five pages of information and then 200 pages of fluff so that they can sell them for 29 bucks. And I looked at this thing and said, this is all the stuff that I understood. And it was not just to teach other people, it was to make sure that I remembered the things that I knew so that going forward, I didn't make the same mistakes. When you write a book about your lessons and what you're supposed to do,

Paul Povolni (46:55.047)
Yeah.

Damion Lupo (47:11.542)
it's really hard to do the opposite because somebody can go, didn't you write in chapter seven that you're supposed to do it this way? You're like, damn it. Yes, that's true. then so it's a good guide to keep you on track as you go through life when you actually have written your rules down.

Paul Povolni (47:22.919)
Yeah. Yeah. To keep yourself accountable. Yeah. Cause they're going to, yeah, you wrote that down and, and, you're not quite living that up to that. out of those principles, I don't know, obviously with 12 books, I don't know whether you remember, you know, all of the principles, but is there one that stands out that maybe we haven't covered?

Damion Lupo (47:42.732)
The ones that we covered were the most important ones. There's all these little nuance and pieces, whether it's technology or ... mean, there's a million things. One of the mistakes I made 25 years ago is I was like, I'm going to do business. I'm going to do real estate. I just didn't really want to focus on bookkeeping. I figured, if there's money in the bank, it must be working. That's just one of those ... Two years later, I went, I don't really know what just happened.

Paul Povolni (48:03.499)
wow.

Damion Lupo (48:08.538)
And so that's one of those things that you absolutely have to keep track of. And if you don't, you really can't run business. You can't run business out of a cash register. a lot of people do, and they don't really know what's going on. It doesn't mean you run and dictate based on just spreadsheets. There's more to business than spreadsheets and metrics. You have to understand a lot more with psychology and vision and emotion and everything else. But that's one of those things. If you miss that one, you're going to do something stupid. You're going get embezzled. There's going to be things.

But I think ultimately the people is the biggest one. It's choosing the right people and being the right people with what you're doing. Because if you get that one wrong, either it's going to be miserable, even if it works, or you're going to fail. And it's not a good failure, but it's just going to be one of those things you're going to hate business. You're going to say, I never want to do this again. So I would say if you're going to get one thing right, make sure it's the people.

Paul Povolni (48:38.269)
Right.

Paul Povolni (48:53.405)
Bye.

Paul Povolni (49:03.217)
Wow. Well, this has been an amazing conversation and time has flown by so quickly. What I like to do sometimes as I wrap this up is, you know, I want to make sure that, you know, if there's a question that I should have asked you, that you wish I'd asked you something that you want to share, is there something that comes to mind?

Damion Lupo (49:21.87)
I think it's more you ask great questions and it was the thing to do is to reinforce the thing. We talked about the people repeatedly and to the thing that I would tell myself 25 years ago and I tell everybody is fail faster and learn quicker. And we tend to avoid the mistakes and that's where all the juice is. Go and do the thing, be bold. And I watch people waste years of their lives squandering.

In fact, it's one of the things that I look back and one of the warnings from my dad right before he died, he looked at me and he said, there were so many things that I wanted to do. And I realized I was listening to regret and it seared itself into my soul. I said, okay, never, never again, is that going to come out of, so like, it's not going to come out of my mouth and I'm to do what I can to help other people move past that. And it has everything to do with moving through mistakes, moving through things that might be a mistake. That's, and how fast can you do that?

That's the key. It's not about getting everything right. It's about doing things right now and moving through them quickly and then stair stepping on top of them to the next thing. Because you don't know where, like the dots you talked about at the beginning, joining all the dots, you have to get through the dots. If you're stuck on one dot, there's no dots. There's just dot.

Paul Povolni (50:33.213)
Right. Right. Man, Damien, this has been so good and a lot of head smacks, a lot of things to consider. I like to say that one idea well executed can change your life. And, you know, you've shared a lot of great principles with your books, with the books that you have available. Are they available on Amazon?

Damion Lupo (50:50.562)
Yeah, they're available on Amazon and there's something that I wrote in the last year called Turnkey Retirement. If you can get it at turnkeyretirement.com, it's literally a 10-minute read. It's 10 steps to 10 million and it's a 10-year plan or less. The reason I did that, I wanted to boil things down for people because my philosophy is that if you can get money out of the way, it's like Forrest Gump said, it's just one less thing to think about. If you can get yourself to the point of 10 million,

It's not just the money. It's literally that you have to become something different than you are today to get to a $10 million number. And once you're there, you'll have this confidence that it doesn't matter what happens because you can always recreate it. So I did that. You can download it at that website. Grab that and it's free. I really would suggest people start with something that they can digest. If you download it don't read it, you're an idiot. And I say that because it won't take you, 10 minutes. I get buying a book and not reading it. That's what most people do.

take leverage off other people's stuff. This is 25 years of beating my head into walls and breaking things and breaking through things. And you have that condensed into the 10 minutes. gives you a little bit of some ideas. And I would encourage everybody to download that.

Paul Povolni (52:00.125)
Give me that link again.

Damion Lupo (52:01.71)
turnkeyretirement.com.

Paul Povolni (52:03.453)
All right, I'll put that in the notes as well. Damien, this has been amazing, man. Thank you so much for this conversation.

Damion Lupo (52:08.878)
Appreciate you, thanks for having me.