Ideas Don’t Matter With Steve Orlando

Hello, and welcome to another episode of the Entrepreneurial Mindset Project.

Today, I’m speaking with a special guest, Steve Orlando, who is not only an incredible entrepreneur, but was one of my very first students when I was experimenting with teaching entrepreneurship at a local high school back in 2006-2007.

Trust me when I tell you Steve has an incredible story to tell.

As a mediocre student from a working-class family, Steve wasn’t sure where he was going in life. Watching his father struggle to get ahead left a profound impression on him from an early age.

Yet a light-bulb moment shifted his awareness in ways that had a profound impact on his life.
What started as a simple idea for an office cleaning business soon morphed into an adjacent opportunity that enabled him to earn $40,000 in his spare time – all while a senior in high school!

From there, Steve has since created a number of successful businesses, none of which required more than a few hundred dollars to start.

In this episode, we cover a lot of ground, yet the one thing that really stood out for me was something that we never really discussed: the original idea doesn’t matter. What really matters is that we get out of the building and start knocking on doors, looking for problems to solve, and talking to people who might have the problem we are trying to solve.

Sooner or later, an opportunity will emerge—an opportunity that you could never have foreseen when you began.

So, without any further ado, I hope you enjoy my conversation with Steve Orlando.

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Listen to the podcast here

Read the transcript below.

Ideas Don’t Matter With Steve Orlando

I’m speaking with a special guest, Steve Orlando. He is not only an incredible entrepreneur but he was one of my first students when I was experimenting with teaching entrepreneurship at a local high school back in the 2006 to 2007 school year. Trust me when I tell you Steve has an incredible story to tell. As a mediocre student from a working-class family, Steve wasn’t sure where he was going in life, Watching his father struggle to get ahead left a profound impression on him from an early age.

He had a light bulb moment that shifted his awareness in ways that had a profound impact on his life. What started as a simple idea for an office cleaning business soon morphed into an adjacent opportunity that enabled him to earn $40,000 in his spare time, all while a senior in high school. From there, Steve has since created a number of successful businesses, none of which required more than a few hundred dollars to start.

In this episode, we cover a lot of ground. The one thing that stood out for me was something that we didn’t talk about. It is the idea that, in the beginning, our ideas don’t matter. What matters is that we get out of the building and start knocking on doors. Start talking to people whose problems we are trying to solve. If our original idea doesn’t work, sooner or later, an opportunity will emerge. It is an opportunity that you could never have foreseen when you began. Without any further ado, I hope you enjoy my conversation with Steve Orlando.

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Steve, welcome to the show.

Thank you for having me, Gary.

I’m excited to talk to you. We met a long time ago in 2006. I wanted to set up a conversation. I was teaching a pilot. I was testing my ideas about entrepreneurial mindset education. I got invited to teach a class at Lake Catholic High School in Mentor, Ohio, which is a suburb of Cleveland. That is where we met. You were a senior in high school at the time.

It was either junior or senior, one of the two.

It was like the 2006 to 2007 school year. I didn’t know what I was doing. I had some assumptions about teaching entrepreneurship. My co-teacher who was on the board of the school at the time invited me in. He is a friend of mine named Mike Baird. He is also a very successful entrepreneur. One of the things I remember about setting up that class, and this is probably a good place to start this conversation, is that Mike came to me and said, “Let’s teach this class in entrepreneurship.” I said, “Great.”

One of his ideas was that all the students had to have a 3.5 GPA to get into our class. His rationale for that was, “We are both busy entrepreneurs. I don’t have the time or the inclination of the patience to spend my time doing this for kids that are just going to be sleeping in the class and not engaged.” I said to him, “Mike, I can’t do that because I wouldn’t have been allowed in the class.” That’s my point. It took me a minute to figure this out, but sometimes entrepreneurship education can resonate with students for whom the school isn’t cutting it. Let me start with that. If I recall, you were a mediocre student. You were a C-student. How would you characterize yourself as a student in high school?

I would say at best, mediocre. The things that I excelled at were music and social classes. It was nothing like brass tack and math. I didn’t do that great. I use it every day in my business now but at the time, it didn’t interest me. These foreign theories of math did not apply to me. History and Science are the same things. I was an average student at best.

We could go off on a whole rant right there. One of the big failures of standardized education is that this doesn’t make it relevant. You see now how important math is and its application.

There are fundamentals that play a role in your life forever. Whether you are balancing your checkbook, who does that anymore anyways, or using numbers to understand how you are paying for things or how your retirement account works. Those things all play a role, but you know all that information by the time you are a freshman in high school.

Why did you sign up for that class? I don’t know if you even remember, but you were a 17 or 18-year-old kid.

I had always been a hustler at heart. The idea of being a business owner was always in the back of my mind. The idea of having my own company and working for myself, and doing things on my own terms had always been prevalent in my mind. I have had little side businesses since I was in grade school. I started my life working at a fancy country club. I saw people with uber success and living the lifestyle that I wanted. That whole lifestyle seemed unattainable to me because I didn’t apply myself in the traditional ways that I thought you had to go to in order to get there.

Excelling in school, going to a fancy college, getting a fancy degree, working at a law firm, or working as a doctor. Those things were what I thought the idea of success was. I thought that would bring value today, but I always knew in the back of my mind that it wasn’t going to be the route that I was going to take personally. I will be completely honest with you, we were not rich as a family. We were fine. We weren’t poor or living on the streets. The idea of being able to learn business tactics from two rich guys in my mind, coming into the office to come and work in the slums with us kids, that was it for me.

There is a lot to unpack there. You are saying that you always had in your mind that you are going to work for yourself somehow. You are working at a country club, and I remember you saying you were a caddy or something.

I’m a caddy and I valet-parked cars.

You had exposure to people who were successful, whatever that means. There are a lot of ways to define that. You were thinking, “That is the life I want for myself, but it is not attainable for me because I’m not a great student. The lawyer, doctor, and engineer thing isn’t for me.” How did you reconcile that?

I could dive deep into that, but there were a lot of scenarios in my life where I had a shift in mindset as I became older. It was around the time that I started taking your class. My dad and I would always talk. We would always be scheming about buying a rental property and getting into something like, “You can make an extra $100 a day doing this if you did it by yourself.”

We were always scheming and always looking for that next hustle and grind, but it never came to fruition until your class. Your class turned the light bulb on in my head. The class opened my eyes to what the entrepreneurial mindset is. At the time, that entrepreneurial mindset to me seemed like a pie in the sky. I wasn’t able to turn that into I can turn my time, services, and value into money. That is what I got out of it. My mindset changed at that point when I had given up on the idea of going right out of school to a job where you make $40,000 a year.

This seems to be the big shift. This is why mindset is important to me in my own thinking. Most of us don’t realize how we have adopted a mindset that tells us that someone else is going to tell us what to learn and what to do in order to be successful. There is this one path toward success, and it is another directed path. It is a linear path and predictable path. You got to abide by these rules. For people like you and me that aren’t great students, that path becomes not available to us, at least in our own minds. The big shift comes when we realize, “It is up to me to figure out how to make myself useful to other humans.”

That was the “pie in the sky” thought process where it is like, “I agree with that. That general thinking makes 100% sense.” It was that initial thinking. You said, “No one is coming to save and rescue you.” I had followed you along. Post-2006 and 2007, if you remember, there was a big economic crash and your message reigned true even stronger.

In 2008 and 2009, I saw my dad, my family, and the people I know struggling, losing their jobs, and having to rethink their careers. They are completely subservient to this system. They don’t possess the skillset or the mindset to take something on and do that. I was lucky at the time that I had to go through this mind-shift change. I witnessed it in real-time happening to the grownups in the room that were well established, had retirements, and good salaries. They have to rethink their entire lives. I got to witness that firsthand. All of those ingredients and recipes molded what my trajectory would be from that point on.

There is a lot to unpack there. I encounter people a lot in my life that have a lot of student debt and work in jobs for which they were not educated. What I see are people who are capable and intelligent. They don’t know how to make themselves useful to other humans when there is not someone else to tell them what to do. It is a paradigm shift.

I was a kid then. Seeing these people that you admire or respect have to make that change, you realize that it is a façade. It was all smoke and mirrors. You think, “I possess this skillset. This is what I’m going to do forever. This is my calling in life. This is what I’m destined for forever.” That is not the case at all. It opens up that entire world to say, “I’m a living and breathing human that can go into any scenario.” If I possess even just the mindset because I don’t have any skillsets that are any more advanced than anybody else. In fact, I have the opposite. Going into scenarios now because I have a different mindset than someone else is a winning ingredient I wouldn’t have otherwise.

It is the shift from another direction to self-direction. It took me a long time to be able to articulate this clearly, but we all live by exchanging. Adam Smith wrote in The Wealth of Nations in 1776, “We all live by exchanging.” The question that you are speaking to is, “What is the useful thing that we exchange? What is the means by which we learn how to make ourselves useful?” People don’t think of that. They think, “I got to get a job and pay the bills.” They don’t like their job or try their best, but they are not getting fulfilled.

Around that time, I went right from Lake Catholic to Lakeland Community College. I enrolled in their SIFE program, which is Students In a Free Enterprise. It is like the Wish version of the ELI version. If you buy something on Wish.com, it shows up crappy and not as not what you wanted. It was like that of your systems.

They were recommended to read from the cubicle to the corner office. They recommend that you meet with companies, people, and big organizations to figure out how you can work in those big institutions, waste management, stairs, and large companies. You would be another number and another cog in the wheel. I realized right off the jump after having the mindset shift from our class back in high school that was not the path I would take. I still went along with it. I still did my best with it, but it was a total shift in mindset.

I remember that you were texting me once circa 2008 and 2009. You were in a class at Lakeland Community College and you were texting me, “You need to be here teaching this class.”

Schools have tried to get a little better about that, but it is the watered-down version. The reality of any entrepreneur’s life is that there is no playbook for it. The playbook is understanding how the world works. That is the foundation you need to understand. From there, figure out what your skillsets are and how those fit into that system. There are no right or wrong ways to do that. How to build a business plan is a waste of time in most scenarios. Any business that I’ve had that has been successful had zero business plan whatsoever. Everything the institution puts together is a watered-down version of what real life does.

Everything that the institution puts together is a watered-down version of what real life does. Share on X

You are saying something that is something important. I want to drill into this for a second. I’m working with a group in South Africa to train teachers in South Africa on how to teach the entrepreneurial mindset. One of the issues that we are dealing with here is that most entrepreneurship education initiatives don’t work. They are not very effective. The reason is that they are teaching it within a managerial paradigm. That is the way you described the course you were taking at Lakeland. I see it all the time.

The entrepreneurial mindset only seems enigmatic to the extent that we are steeped in a managerial paradigm. That is hierarchical. It is linear. It is about error reduction, repetition, and efficiency. Entrepreneurship is almost the exact opposite of that. It is error-inducing. It is experimental and explorative. As soon as I hear the word business plan, I go, “You are in a managerial mindset.”

When you have to take the masses and push them into something like that, that is probably the best way to do it at scale. Actually, I would disagree. What you are doing is the better way to do that. The managerial mindset works within the entrepreneur’s system. The goal is to run a company that is full of a bunch of systems of people doing your job for you.

You could still have an entrepreneurial environment and culture. At the end of the day, if you are going to start a company, you need to have systems in place that people fall within. You are not teaching entrepreneurship in that case. You are teaching how to excel and how to work the best within the system that is already in place. It is the hierarchy. You are not thinking for yourself. You are thinking for the company you are working for.

You are fulfilling a predetermined role that is systematized and routinized. Here is the dilemma. I think you need both. A lot of entrepreneurs fail because they can’t transition into managerial. They want to keep exploring and experimenting. They love the novelty. They get hooked on that. They don’t know how to scale. Mike Baird was one of the rare people who could be innovative, but then he transitioned into a managerial role.

I found partners to compensate for it. I find business partners that are managerial because you need both. That is the dilemma. All kids need exposure to entrepreneurial thinking. We will talk about that in a minute, but I want to get back to your story. There is an important point here that you mentioned earlier. You are riffing with your dad. Your dad’s got a day job. He is also engaging you in guide hustle ideas. That is an important part of the story.

I remember it being as young as seven years old. I’m six years old, it sounds crazy. My dad had read all the books on using OPM or other people’s money to buy rental properties, try to scale, build a rental portfolio, retire, and do all those things. Looking back at it now, I’m a six-year-old. We just moved into this house that my dad admittedly had told me he probably overpaid for or strung himself to get us into. I remember it being in first grade.

At night, he’s venting to me in our nighttime routine saying, “You got to live. Get yourself a nice house that you can afford. You work your butt off to get a second property. You work your butt off until that is paid off, and you do another one.” I haven’t even got my first communion yet and he is telling me, “This is the way that you have to do it.” Maybe he was telling me because he was projecting his uncomfort because the scenario that he went through in his trial for that didn’t end well.

Was he saying to you that you got to take a different path?

It is following his same principles but maybe being more conservative with it. I’m saying this in hindsight now, and maybe I’m butchering it. The way I recall it is his venting to me was a way of him saying, “You could do this better than I can.” If I could be completely honest, that is how he was in it. He changed from real estate to having a side business or trying to work for one of these guys that you had caddied for at the country club or figuring out what they do. The idea in my mind was given to me at a young age, and it morphed from there into its own thing.

That is an important part of the story. Regardless of what your dad’s intention was, it landed in your brain as “There is got to be a better way.” The conventional path wasn’t working for your dad. It was stressing him out. He wasn’t enjoying his life. I’m paraphrasing here, but he was struggling.

He was struggling with that. He didn’t get the destiny he set out for. He was sold fake bills of goods from the classes or books he read. He knew that life was out there. If he did it the right way, you could. I’m paraphrasing. I don’t want to make it seem like my dad was this miserable person in his whole life. If I could be honest, his talks inventing to me were like, “Please do this. You owe it to yourself to do that.”

This is coming out to me now. I think that is where the real inception of that concept came in. Had the book worked out for him or had he been successful in those that changed his lifestyle, maybe I wouldn’t have had that, but we couldn’t buy and do certain things. That guilt of his made him more vocal about making those changes as a younger person.

There is another piece of the story here that is important, which is why many entrepreneurs come from challenging economic backgrounds. In some perverse way, adversity becomes an advantage. If you are raised in privilege, you are getting straight A’s, and you are on your way to Stanford, there is no reason to be entrepreneurial. I could make the argument that there is, but you are not in any real pain. The system is working for you. You are floating down the river.

The pain is subjective. If you put it into perspective, we didn’t have cable TV. We didn’t drive nice cars. I still went to a private school from kindergarten through high school. Was I going through economic pain? No, but I guess that idea of saying, “There is a lot more out there that you can do. You can build a life for yourself,” is more aligned with what you want to do in this world. That is where the pain was. The pain was you could do a lot more. If you do it the way that you are supposed to, you can be a lot more effective in the marketplace and community. That is what translated more to me.

Pain is really subjective. Share on X

That is an important point. The pain is contextual.

I have heard people on your show that have had real pains. I would say that I did not have that pain growing up.

Thank you for saying that. I get it. You were raised in the lower end of the middle class. You are going to a private school. I’m sure a lot of your friends were better off than you. It is a relativity psychology. They call it the Relative Deprivation Theory. If everybody around you was poorer than you, you would have interpreted it completely differently. A lot of people you were surrounded with were better off, and you get the job at the country club. Those are all mindset concepts that land in our brains in ways that we are not always conscious of, but they have an important impact.

You said something that I want to put a pin in so we can double-click on it in a minute. You were also talking about making a contribution to the community. That is an important part of the entrepreneur’s story that doesn’t always get brought to the fore, but I want to get back to your story. You have done a good job of setting up. You are brought up in a family. Your dad is struggling. He is in your ear like you got to find a better way. You are doing side hustles as a kid, trying things. You are not a great student in school. School is not resonating with you. What was your first big entrepreneurial a-ha moment?

It was in your class. I didn’t know that the goal of the class at that point was to start a business. Having a history of wanting to get out there and hustle, I went out in search of starting a cleaning business. I’m an unskilled laborer. I’m not afraid of knocking on doors. I will go door to door and try to clean offices. In the first few days of doing that, people took the little flyer I printed out. They said, “We will give you a call.” A property management company said, “We don’t need someone to clean this office, but we have a contract with a parking lot cleaning company.” They are not performing or something in their system wasn’t working. They asked if I would put a bid together to clean their parking lot.

That was the first person that said, “I want to pay you for a service that our company needs. Can you do that?” I was like, “The idea of sweeping a parking lot sounds pretty elementary. I will work that out.” Putting that whole process together like, “Do I send them a quote? How does this work?” I will never forget it. We were putting together the proposal to fax from the Lake Catholic office with a cover letter on it. We looked up what a good proposal would look like. The bid was $2,700 a month. They are like, cool, “Come out and start doing it.” I’m like, “These guys are paying me $2,500 to come and clean this stuff up.”

My friends never had “good jobs.” We are making $10 an hour. I’m doing the math being like, “I’m going to work four hours a week. I’m getting $1,000 every week to do this. This is amazing.” I execute that first contract. It happened around November and December. I remember that Christmas, my parents got me brooms, sweepers, and garbage bags. I was like, “I’m getting garbage bags for Christmas.” At the same time, I’m like, “This is what I need to start my business. I got a contract here. I’m going to do it.” The exchange of someone saying, “We have a service that we need. Can you do this?” I said, “Sure, here is a price.” They said, “Yes.” That was the a-ha moment.

I have told that story in some form many times to educators around the world. One of the things that is important for people to hear is that a lot of people teach entrepreneurship, and they are teaching management. When they start, you have to understand economics, accounting, and profit and loss. My philosophy was the opposite. Rather than telling you guys to write business plans and figure it all out before you go, I was saying, “Get what are your ideas and go out in the world and talk to people who have the problem that you are trying to solve.”

I would even take it a step behind that and say, “Find out what the problem is out there,” because you might go out there trying to solve a problem that might not exist. I see people all the time that want to start a business that solves a problem and is close to the problem that someone has, but the actual problem that they have is the goal. They are like, “That doesn’t align with what we do. This is what our business does.” No, that is the moment where you say, “If that is the problem you have, we can do that.”

Find out what the problem is out there because you can’t go out trying to solve a problem that might not exist. Share on X

That was your story. You were trying to clean offices. No one was responding to you. I specifically remember coaching you because you were knocking on doors diligently and getting no response. It wasn’t resonating with the people. I remember talking to you about this vaguely, but I’m trying to help you understand the world through the lens of the customer. Maybe the business owner isn’t comfortable with a seventeen-year-old kid in their office after hours when they are not there.

You said a lot there that I want to unpack. People set out to solve problems that don’t exist. That is encouraged in many entrepreneurship programs. They were like, “You got an idea. Write a business plan. We will find you some money.” We have to go upstream and see what evidence you have. There is a problem here. You need evidence. It is not speculation. You can fool yourself easily.

The other point that I wanted to bring up briefly, and you understand this intuitively, is that opportunity finding is about understanding human needs in three dimensions. It is not just about the transactional need. It is about the social and emotional dimensions of the need. Yes, I need the parking lot cleaned, but I need somebody to do it reliably and responsibly. They show up every time and over-delivered delight. That is where the opportunity lies. Entrepreneurs aren’t inventors, by and large.

I had a revelation on the way in when I was thinking about how to answer questions. I have thought this, but I gave it a full deep dive on the drive-in. I’m a drummer by trade. I played in bands. A lot of people thought that I was a good drummer. They said, “Steve, you are a good drummer. This is what you should do with your life.” If you break down what drummers are, it is that you operate and fills in a measure of your own rift that is a copy of someone else’s rift. How you put those rifts together makes your style. The same drummer can play the same song completely differently. One person sounds great and the other person doesn’t, but we are all using existing rifts and beats within a four-beat measure.

For any business I have ever been a part of, I’m putting the Steve rhythm within the four-beat measure. There are five different people that can come in and play the same song with their own beat. Some beats suck, and some beats are better. I’m not doing it. I’m copying. I have heard things that are better and I incorporate it into mine. That is what I think. I see a lot of parallels there with any business that I’m in, whether it is parking lot cleaning, selling forklifts, and renting chairs for weddings. You put your brand on your riff in that four-beat measure and see if it resonates or not. I’m not reinventing the wheel. I’m not putting together some brand-new thing.

First of all, we have to break the myth that, as entrepreneurs and inventors, those are exceptional cases, not the rule. We have trained thousands of teachers around the world. We immerse them in entrepreneurial processes. They are always struggling to come up with something that has never been done before. I don’t want to discourage invention or creative thinking. I’m just saying that very often, it betrays a get-rich-quick mentality. I had a venture capitalist explain this to me once. It is a horse and a jockey. The get-rich-quick inventor mentality is that “I don’t need to be a good jockey. I just need a fast horse.” The opposite is true. You could take any the horse, get on that thing, and ride the hell out of it.

We are probably living in the most opportunity-rich time and human history. What I’m trying to do with this show is I’m trying to get out of you and the other entrepreneurs like you your unconscious assumptions or the things in your brain that are driving the behavior that you may or may not be aware of.

The point I’m trying to make here is that opportunities are everywhere, but the problem is they are invisible and latent. They are present but not visible. They can’t be seen with the naked eye. They can’t be discovered with a managerial mindset. People know what they want and need sometimes. To make matters even more complex, what people say they want and what they will pay for are two different things.

The opportunities are absolutely everywhere. Share on X

That is why I’m keen on promoting an iterative experimental evidence-based process rather than opinion-based entrepreneurship processes like pitch competitions and business plans. It relies on someone’s opinion that a penny isn’t worth a crap. It was like, “What evidence do you have that your thing is useful to other humans?”

That is the irony of that, and this has nothing to do with the class you set up. If you recall, at the end of the class, five people came up and gave their pitches on their business, whoever the most or whatever it was. They brought in business owners and respectable and successful people to be the judges for that. You and Mike were not the judges there. We all gave a pitch.

The winner was location-based like wristbands at amusement parks for kids didn’t exist. All of these ideas ran the gamut. My pitch was like, “We are a cleaning a parking lot company, but I made $40,000 so far, and I didn’t get competition.” It goes back to what you are saying. The hierarchy and institution award the flashy, the new, the horse, and the jockey. If it is an old school business or something like this service-based thing, they were like, “It’s not that attractive,” but it is paying bills. I was making an adult salary as an eighteen-year-old.

You were still going to school. That was your first a-ha moment. You got some traction as an entrepreneur. You had that epiphany like, “My friends are all making $10 an hour if they are lucky. I’m making $1,000 a week working a few hours.” This is a part-time thing. I don’t remember the details. That didn’t hold in an idyllic situation. Something fell apart halfway through it. Was it the economic crash or something? I don’t know.

I didn’t have the foresight at the time to realize what you were saying. This can be scaled across multiple customers. This could be taken to a different level and grow from it. I grew within the property management company to do other services for them, but I had all my eggs in one basket. In 2008, the economic crash played a role in the service I was offering. At the end of the month, I’m being able to write up invoices for $5,000 to $6,000.

There were services I was doing, but it was never questioned. Eventually, it was like, “We don’t need the flowers watered at these business parks anymore. We had to do some service in the back here that doesn’t need to be done anymore. We are going to rely on our contracts with the parking lot.” It eventually went down to nothing. I had a taste of what the opportunity was and how good it felt. I didn’t do anything to prepare myself for the end of it because I was a stupid kid.

I had a taste for what the upside could be. I also witnessed it go to nothing. I had a little bit of a scar on myself to say, “I want to go back to what that is. I don’t know how I’m going to. I got to find another opportunity.” It sounds like it was more thought out and well-constructed going into that, but that wasn’t the case. I was looking for my next move. I had a gutter cleaning business that I did for a handful of years, but that was seasonal. We weren’t turning into some institutional thing.

That is what it was. It was a pivot.

Instead of having one client that will give you $5,000 a month, it would be 100 clients giving you $100 at a time, and you try to get those as much as you can. It is seasonal. It is not a full-time thing. I didn’t have the right insurance in place for it, but that grew a little bit and expanded into some mini-construction. There were some press done with me at the time. My friends all knew that I had a business.

A close friend came to me with this idea. He came to me because he knew that I was a business person. I didn’t have any credentials to run a business necessarily except for the fact that I had done it. He came to me and said, “I had this idea that if you made a phone call, instead of hearing a ring until your friend picked up, you heard a ring-back tone of an advertisement, and that advertisement would pay for your cell phone bill.” I was like, “That is such a great idea.”

I didn’t have any credentials to take that anywhere except for the fact that I didn’t give a crap. I would be like, “Let’s start calling on cellphone companies. Let’s talk to people.” I called you. You connected me with Sam. Sam introduced me to the startup world. Eventually, we became a portfolio company at a local business incubator, which I learned a ton more about. I got a small investment to be a part of that. We raised money from a small investor group. We got a tax credit to allow them to be an investor. We had a letter of intent on the table with a local cellphone provider, Revol Wireless. That ended up not doing anything. They ended up saying, “We will do it.” They were bought by Sprint, and it never went anywhere.

I’m in this constant state of identifying myself with these businesses. They are working or not working. All the while, I’m trying to have a life, pay bills, and do whatever I have to do. I don’t want to go too far up ahead here, but I was going back to my roots to do some of these cleaning/project management gigs in a company that was downsizing in this economy. They needed to get rid of all their desks, offices, chairs, phone systems, and extra laptops. I went in and they paid me to get rid of it all. I brought it back to my apartment and sold it on Craigslist.

I’m in this constant state of hustling, going out and picking up new things, dropping furniture off at furniture stores, and figuring out how to do that. This one company said, “What would you pay me for this forklift? We need to get rid of it.” I didn’t know anything about forklifts. I said, “$500.” They said, “Sounds good. It is yours.” I made a couple of phone calls. There was a forklift guy that was a member of the country club I caddied at. I said, “How much will you pay me for this forklift?” He said, “$1,500. I will pick it up today and pay you.” I was like, “You can do that.” I made $1,000 selling a forklift doing nothing, and I knew nothing about the forklifts. I’m like, “I’m going to find as many forklifts as possible.”

Your brain went to, “Can I repeat this? Is this repeatable?” Let me drill into this before you get too far ahead. This is such a crazy cool story. I wanted to talk about you as a kid in school. You get this job. You are making ten times as much money as your friends. You have this wild moment, but the economy shifts. All of a sudden, it starts going away. You are like, “I got to figure it out.”

The point that I want to make here for folks is that because of the environment in which we operate as entrepreneurs, I like to equate entrepreneurs with modern-day hunter-gatherers. We expect the wind and the tide to shift constantly. We understand that it is up to us to figure out how to make ourselves useful. We don’t have expectations of someone else telling me what to learn and do, or the linearity and predictability. It is always changing.

A good analogy for this is to think about GPS. We rely on GPS to navigate to the extent where our navigational abilities atrophy. You get somewhere, you are following the directions, and your phone dies. You can’t figure out how to get back home. It is the same thing if you are relying on someone else to tell you what to do for work all the time. Your brain isn’t attuned. I read somewhere that the ancient Greeks figured out how to get into the Arctic Circle and back. There are no roads, road signs, maps, or landmarks. I’m saying that to demystify it. The highly ambiguous, self-directed, and resource-constrained nature of the beast is what cultivates the entrepreneurial mindset.

I wanted to make that point, and I want to come back to this idea. You got the parking lot cleaning thing. That started to morph, change, and fall apart in the 2008 housing and economic crisis. You are figuring out how to adapt. You pivot to gutter cleaning. You are hustling all over the place. A guy sells you a forklift, and you make $1,000. That is why I want to pick that back up.

Before we get back to the forklift story, I want to make sure the audience understands what you are saying. You have these primitive little hustles going. Things are working, and they are not working. You are still in this iterative experimental phase. Somebody that came to you with an idea that had the potential to be a big idea. That was Cell-A-Spot, as I recall the original name of it. That thrusts you into a higher level of entrepreneurship. That got you exposed to venture capitalists, Angel investors, and successful entrepreneurs. Sam was instrumental in helping mentor you there. Before we get back to the forklift story, what was that like for you? All of a sudden, you are immersed and hanging around with the country club folks.

It is almost like you are a chameleon. You change your identity to what you are now a thing of, and I still do it now. Instead of wearing jeans and a hoodie, you go into something you are wearing khakis and a sport coat. You are acting the part of this now, but you are still going into it with the same mindset. You are solving a need for someone, and how you are going to do that for someone.

People give you the benefit of the doubt to say, “If you are going into doing that, that is what you are now.” For me, it was like, “I’m a startup guy. That is what it is. I have no business being a startup person, but it is nobody’s business to be whatever they are.” You eventually get into that mindset. You start reading articles about what that means and what the process looks like. You try to mimic that. You know what your internal goals are and how to get there. You start following your own playbook to get there. You thrust yourself into a new position and circle of influence. Now you are identified as that.

The important thing you have said there is you are willing to throw yourself into a situation where you’re the dumbest guy in the room. You feel like you don’t even fit there, but you do it anyway. That is an important point I want people to understand. I cannot overemphasize the importance of that. People won’t do that. What is worse is they come up with excuses like somebody else is stopping them. It is our own internal fear and self-doubt. That ability to put yourself in situations where you are the poorest, the dumbest, the least qualified, and the least successful guy in the room is what makes or breaks and can make all the difference.

My exposure to people that were successful was when I was caddying or valeting cars and realizing that we are not that much different people and saying, “I could do what you do.” Maybe that is cockiness or a different way that I can justify it in my head. I was like, “If someone else can do it, I could do it too.”

There is so much research that supports that. When you are around people, you start to see how the sausage gets made. You start to realize, “These people aren’t any smarter or more talented than I am. If you can do it, I can do it.” I saw a study a few months ago in the New York Times about the single most important determining factor that enables people to escape poverty. It is frequent exposure to people of a higher socioeconomic status. It is like osmosis. They are not necessarily telling you exactly what to do and how to do it, but it is the cultural immersion that makes the difference.

There is an analogy in golf. You want to play in a foursome and be the worst golfer there. By being around the people that are playing better, you tend to play better yourself. It is the same thing with musicians, working out, and exercising. You surround yourself with people that do it better than you, and you find yourself operating at a higher ability.

Surround yourself with people that do things better than you. You’ll find yourself operating at a higher ability. Share on X

That should be the high point. That is one of the most important things we could talk about. If you are not willing to be the dumbest guy in the room, the poorest golfer in the foursome, you are going to stay stuck. That is an important point. What I want to come back to is you are going from parking lot cleaning to gutter cleaning, side hustling, swapping, and buying tow motors. All of a sudden, a guy comes to you with this idea with the potential to be huge.

You are in with venture capitalists. You are running a fast-paced team. This thing is starting to go. You are having meetings with global companies, or at least national companies. You got people that are surrounding you that are indicating they are willing to throw money at you. That also didn’t pan out. You came right up to the edge of it.

Twice. With Cell-A-Spot, it was an LLC that my friend and I started. We ran it to the point where Revol was ready to sign up. Revol Wireless was a local regional cell phone provider located in Cleveland. I took it all the way to the top. They flew in the CEO from Hawaii to see this through. We had our investors there. They said, “This is a no-brainer. We are down for it.” It then went to crickets and nothing happened. That business in itself and startups, in general, don’t generate any revenue up to that point. That is why these side hustles were happening simultaneously.

How old are you this time? You are 19 or 20 years old. You got some community college in you, and you got the CEO of a huge company flying to meet with you. How is that landing in your brain?

At the time, it was very nerve-wracking, but you felt like you belonged. It was that mindset of saying, “This is me now. I’m doing this because I want to see it work and see it through.” You are spot on with that. When that failed, that is when the project management business took my full-time energy. When I got into that forklift opportunity, I started buying and selling them more. From there, the company I was selling the forklifts to said, “Why don’t you come work here and do what you are doing for us? We will teach you to be a sales rep. You can buy equipment. We will put you on a commission structure.”

I did that for about a year. While I was doing that, the investors I had from Cell-A-Spot said, “We want to get back in on this. There was an opportunity to join another business incubator, which was Dan Gilbert’s business incubator.” At this point, I had been making good money selling forklifts for two years. I was like, “Do I go right back into this and go back into the startup world?” I said, “Sure.” I quit and went to work to do this.

We ended up building the first internet phone. We ended up getting Sprint to say, “We are okay with this. We like this concept, but you need to test it on a smaller market. We are not going to give you access to our switch.” It is what we needed to do to intercept the phone calls. They said, “You can lease data from us if you want via an MVNO.” It was like Boost Mobile. It was owned by Sprint. They lease minutes, texts, and data from them. They said, “If you can get it done through there, then you can do that.”

We partnered with a company in San Diego that sold us data. We said, “The only way that we can put this together is by building a voice-over IP application that’s native to the phone, and we can route the calls however we want to.” We built the first-ever Wi-Fi-enabled phone. You can make a phone call on an airplane. You can make a phone call anywhere you want to in the world. If there’s WiFi on the moon, it will work.

It took a long time to build that. We had run out of money from the first round of investments. We raised additional money, and Sprint shelved it. It went down to nothing again. At this point, I’m back in the same spot again as I was before. You see these peaks. It goes up and it goes down. That is when I went and started this forklift business with the then-vice president of the forklift company. We have been doing that since 2015. There is way more to the story. I can go on for hours.

That forklift business is still going.

This is what I do all day long. We sell 40 forklifts a week. We buy and sell them all over North America, South America, Western Europe, and Australia. I was at a conference where we consult with leasing banks like Bank of America and Wells Fargo to buy their off-lease assets from them and deploy them and sell them to dealers all over the world. That is the business I run.

What I want to dig into for a minute here is that the logic of the entrepreneurial brain is the opposite of managerial logic. Psychologists would call it causal reasoning. It is a fancy word for saying, “You figure everything out, and then you act on it.” You plan and then you act. That is causal reasoning. That is prudent in a lot of situations. You should look both ways before you cross the street because the cost of failure is high. What people don’t realize and what no one teaches you in school is there is an alternate logic that sometimes is applicable, which is called effectual reasoning. You have to go to know. You cannot know before you go.

That is what messes with people’s minds. It is called ambiguity aversion. We are loathed to go down a path without a predictable outcome and modicum of certainty of the outcomes. What your story powerfully demonstrates is the power of effectual reasoning, “I’m going to go. I’m going to start knocking on doors. People don’t need offices cleaned, but there is a parking lot cleaning opportunity.” There is no amount of business planning. You could business plan for 1,000 years. You could Google research for a million years. That opportunity is never going to become visible.

Let’s take it a step further than that. I already had a business with forklifts at this point. Do you want me to go down this path with the chair business?

Yes. Just to be clear. The forklift business is not your only business. Is that what you are saying?

Yes and no, and I will tell you in this story. We started the company in 2015. I proposed to my now-wife at the end of 2016. When the forklift business started, it was a profitable business. I have more money now. I have more discretionary income. I can do more with it. My brother-in-law was working for a video company and wanted to start his own wedding video business. He was too afraid to take the leap, but he was good at what he did. I said, “I will put $7,000 in your business. Let’s figure this thing out and get you to as many weddings as we can. It can’t be that hard. The threshold for someone to get into this business is low, and your quality is good.”

We found out how to market him on The Knot and these existing websites. Within a three months span, we got him 52 weddings booked in the first year, which is insane. He is charging $2,000 for the wedding. He went from working part-time for this videographer and being a barback to now having a $150,000 business almost overnight.

I understood how the inner workings of that worked. I now understand, and that was the first aha, that I had an influence on something that took off quickly and was able to become successful. When I proposed to my wife, we went around looking for wedding venues. My wife found this amazing venue in downtown Cleveland. She said, “I love it. I’m sold. I just hate the chairs.” I was like, “The chairs are free. They are here. She was like, “I really want these upgraded chairs.”

My wife kept what she wanted. I was like, “I’m going to call around and figure out what it costs to rent these things.” Every company in town wanted $10 a piece to rent these chairs. I was like, “We had a big wedding for 300 people. It was going to be $4,500 for chairs for my wedding.” I was like, “That is insane.” I looked online as to what it would cost to buy these chairs, and they were $29 apiece. I’m like,

“Do you mean to tell me these guys are running these things three times, and they get their money back? That is a good return on investment. I will buy 300 chairs for our wedding. I will find a cheap domain WeddingChairs.net. I will advertise in these same places where I advertise the video business. I will go out at $4 apiece. I will undercut the market and get my money back out of these things.”

That first year, we booked 100 weddings. We expanded our inventory from 300 chairs to 750. Fast forward to two years, we had 2,000 chairs. Fast forward to six years, we had 5,500 chairs. We were doing 550 weddings a year. My wife quit her job full-time to do that. We had six full-time guys, trucks, and forklifts. We are importing them from China. We sold the business for a profit in 2022.

That is something where it was like there was a need in the marketplace. The business already existed. It goes back to that drumming thing. The Steve rhythm within that measure was the success there. I don’t mean to put any stock into me personally as much as it is. The opportunity was there. It worked. It was a repeatable thing. It was one of those side hustles that grew. That was the first business endeavor while still running the forklift business that I could see grow, manage, and turn into something that was a successful exit for us.

What you are doing that you may not even be aware of is you are trying lots of things on a small scale. That is what people don’t understand. You don’t need money to be an entrepreneur. You need money to open a business, but that is managerial thinking.

Do you know how much I started that business with? It was eventually doing $600,000 a year in revenue. I bought one sample chair that I posted a picture of on our listing site. I paid $100 a month for advertising for it. People would give you deposits in advance. I had to be an upstanding citizen and do what I was going to say, but my entire inventory was funded by the customers I would have a year later. They would all give me a deposit upfront. In the beginning, when I wanted to scale quicker, I put more money into it. We are talking a couple of hundred bucks to start that business in total.

That is what people don’t get. The managerial mindset is like, “Let me back up one step further before I even get into the managerial mindset.” Many people start a business, but they are only thinking about themselves. That is the simple secret that is hiding in plain sight. They are only thinking, “How can I make money?” They don’t pay attention to what other people need.

The minute you start paying attention to other people’s needs, opportunities start popping up. The second point is you don’t need money. Maybe you need $100. What I say to entrepreneurs a lot is, “Don’t quit your day job. Don’t drop out of school. Don’t mortgage your house. Look around in the margins. Experiment and try stuff.

That is what we did with this forklift business. When we started our bank account, we each had $30 in our pocket. That is what we came to the branch with. That is what we started the business with. Since the inception of this business, we have done well over tens of millions of dollars in revenue with not one penny of our own money having to fund the business at all.

That is such an important point. I can’t overemphasize that. People think you need money to get ahead. I don’t know about you, but I grew up in a blue-collar community. I heard people all the time talking about, “It takes money to make money.”

If you want to make more money, you work overtime.

You believe that stuff. A lot of people use “It takes money to make money” as a way to say, “A guy like me can’t get ahead. I’m screwed. This is the domain of the rich and the privileged. I’m stuck here and they don’t get it.” What it comes back to is what we have started this conversation on, you got to figure out how to make yourself useful to other humans. You got to pay attention to what people need. You got to try lots of things on a small scale.

Most of the things that you try won’t work. Most of it is like gutter cleaning or parking lot cleaning. It works for a minute. It is not the ultimate solution. People look at Steve Orlando and think, “That guy is lucky. He is gifted.” I don’t mean to take away from your abilities in any way, but what I see in entrepreneurs that I interview is there is nothing remarkable about the entrepreneurs themselves. I call it the banality of amazing.

It is funny because, since 2010 when the Mark Zuckerbergs of the world came up and the startups that came through, the word entrepreneur almost became a sexy term. I have always thought, “It is the opposite of sexy.” You are wondering where the next gig is going to come from. You are not making a lot of money. You are by yourself. You are depressed. You are seeing your friends grow in their careers or doing whatever, and living a life that fits the mold of that same institutional downstream thinking that we have seen our whole lives. We’re wondering, “Is this the right move? Am I going to be 40 years old and still hustling to do X, Y, and Z?” You don’t know that at the moment.

I happened to start young, but the timing that we have gone through that entire saga, there were seven years there where I was not making a lot of money. I wouldn’t be able to buy a house. I wouldn’t even be able to get married to someone at the time. You were making money at the gigs you were doing. You felt you were working your own hours. It took a long time for the first thing to hit and become successful enough to do what it is. I feel like I’m now in a position where anything that I can dabble in, you can take that risk of not going all in on it and seeing if it goes or not. Your only stuff that grows is your success.

In the early years, when you are not getting successful, we go back to the Relative Deprivation Theory. You see your schoolmates. They have gone on to college. They got good jobs and bought a house. They are following a conventional path. You start to question yourself. That is a real thing. The model that I’m advocating that people take is, “Don’t quit your day job. Don’t go running off crazy and experiment in the margins. Preserve the core of whatever stability you have.”

Here is the way I think about it. There is this innate tendency in all living things towards growth. It is called a self-actualizing tendency. Every acorn has the capacity and the desire to become a mighty oak tree. It is a compelling force within every human being, but there are constraining forces. Some of those constraining forces are internal, which is the need for stability. Those two things compete with each other.

To bring that around, my dad was in that same boat. The irony of that is the stability he had wasn’t that stable, but he saw a path of his life and the instability that came with it. Whether it was stable or not, he convinced himself that was the case to ever allow him to do what he wanted to do and to see the destiny he wanted. That is an acorn that fell. It was watered. It is growing. I’m not trying to downplay my dad’s life or career. He does fine. I know that my dad wanted to do more. I feel like he didn’t have the mindset to say, “I didn’t see the path.”

Your dad was instrumental in my own entrepreneurial journey because, in the class that I taught at Lake Catholic, I had been thinking about these ideas since 1991. I had already been thinking about these ideas for 15 or 16 years before I met you. My assumptions were entrepreneurial thinking can empower people. I was always thinking of it like that. It is not necessarily a business discipline, but this could empower people in a myriad of ways, not just to start businesses.

I remember your dad sent me an email. I don’t know if it was a phone call or an email. I don’t remember. He said to me, “I can’t believe the change I have seen in my son.” I will never forget that. He said, “He is getting out of bed at 5:00 in the morning to clean a parking lot in the rain before he goes to school.” He saw this profound change in you. After this somewhat pregnant pause, he said to me, “Is there any way I could take this class?” That was a moment that landed in my brain like, “I got to take this stuff seriously.”

What I was doing with that class is I was testing my own ideas. The class gave me an opportunity. One of the things I will go back to that I want to point out for the audience is when Mike Baird said to me, “We need to have a 3.5 GPA as the criteria for the class,” I said, “I can’t be a part of that.” I didn’t have a 3.5 GPA. There is a dilemma I have personally. I said, “I don’t want kids sleeping on their desks either. Let’s make the kids come to school an hour early.” We had this class from 7:00 to 7:45 in the morning. What I want the audience to understand is you were coming to school an hour before school to take a class.

I don’t think the class had any credits, but it was a complete elective. You went because you wanted to go. It wasn’t like you got credit to take one last class during the day.

The amazing thing was 24 kids came to this class. They weren’t doing it to get the credit. They were doing it to get the learning, which was unique. The point that I like to draw from that either is in the entrepreneurial domain, your willingness to get out of bed an hour before everybody else is as important as your GPA, if not more. That is an important part of the story. You and I met a couple of months ago for breakfast to catch up. I said to you that it has been exciting to see your entrepreneurial journey, which I take no credit for whatsoever.

I think you should take some credit for that.

I think, “Steve Orlando is going to find a way no matter what.” You were looking for answers. Maybe I got you the answers a little bit sooner or accelerated in some small way. What would you say to other folks who are thinking about doing their own thing?

You can’t have any preconceived notions of what anything is. I had no extra credibility, no successful business history, and no connections to the spaces that I ever went to. You still get the benefit of the doubt from people for being there. As you said, “Showing up to class early.” You could be going to a networking event with the intention and going in with no actual preconceived notions of what you want. It sounds vague to say out loud.

If your goal is to do something on your own, be open to hearing what the opportunity is out there. Mold and identify yourself with that problem solution and act the part. That is it. Don’t be afraid to put yourself in any scenario out there. You don’t have to be a fast talker. You don’t have to know stats about things. It is not like you get quizzed when you are talking to someone casually. Those opportunities tend to present themselves more often than you think.

The willingness to be the dumbest guy in the room is a superpower. Steve, what about you? The way I think about entrepreneurship and what I say to people is, “It is not that complicated.” You are pursuing things that are interesting to you in ways that are useful to other humans. That is all it is. What I don’t think people understand, and I want you to tell me if this resonates with you or not, is that as an entrepreneur, I don’t see a big distinction between work and life, or work and play.

I’m not thinking, “Thank God it’s Friday.” I’m thinking, “Thank God it is Monday.” I want people to understand that for us, and I’m including you in this. You could extricate yourself from this, but work isn’t work. It is work, but it is not taxing in that way. It is fulfilling, interesting, and engaging. It is not just an unnecessary evil.

You nailed it on the head. There is still work to be done within your organization. The better comparison would be in the chair business specifically. That is a cut-and-dry business. You got to deliver the chairs and pick them up. If we were short-staffed, I would go and do a lot of these deliveries, midnight pickups, drive to Cincinnati, and come back home the same day. In a normal scenario, the employees we had hated it. They hated having to work long hours. When it is your thing, it didn’t. I wasn’t even taking home a paycheck. I didn’t get paid by the hour. I got what I got from the business for it being profitable. Whether I worked those hours or not, it wasn’t like I took home an extra $100 that day.

I had a family and stuff. That changed, but I was leaving the forklift office after doing my thing to make money, create value in the marketplace, go to the chair house, and work with the guys. I go out and do the delivery. I drive the truck around. It didn’t feel like I was like, “I got to do this for the day.” I’m doing my own thing. This is my business. This is my human, living, and breathing thing that I’m a part of. I’m in it. I’m in the bloodstream. I’m in the lungs. I’m a part of it. I loved it. It doesn’t feel like work.

I started to ask this question earlier, and I interrupted myself. What is it about Steve Orlando that makes this work? I see that entrepreneurs don’t have any personality traits that are essential for being entrepreneurial. They tend to use whatever their traits are in ways that work. What is your superpower?

I enjoy going into things and making something out of nothing. I like coming into something and saying, “Nobody knows who I am. I can turn myself into a force to be reckoned with.” I like that a lot. I don’t know the path to get there. It is the overconfidence and the inability to care about what other people think. That has to be it. Being able to go into a scenario and someone could say, “That is the dumbest thing I have ever heard.” I will be like, “That is what you think.” You take something from that, and you move on to the next conversation saying, “I think this way.” I should have thought of a better answer for that because I don’t know.

I don’t even want you to think too hard about it. Those are some important nuggets. It is the willingness to be the dumbest guy in the room and the willingness to be wrong. The thing that you articulated that I want to come back to is I want to help folks understand to keep their day job. The right word here is to reappropriate some small percentage of your thought, time, and effort into figuring out new ways to make yourself more useful to more humans. When you do that, life becomes an adventure. It is like one giant Easter egg hunt. There is an opportunity under every rock and corner. Life is interesting. Your curiosity has awakened. You are attuned to what other people need. You are trying lots of things. You are meeting interesting people. It is crazy.

It gives you a new outlook on life. If I could be brutally honest, I have been in this business, specifically the forklift, for a long time now. The opportunities within this space have almost become routine. I don’t want to say the spark has died because I still enjoy what I do a lot. In that world, the opportunities you are finding seem like, “Here is another opportunity within that space.”

I get motivated to find an opportunity in something that is not even related, like the chairs. I was like, “I’m bringing value somewhere else completely.” I’m like, “I’m cool about making money here, but this little shiny thing over here. I love that stuff.” The beauty is you never have to quit your job to do that. You never have to completely stop, go and put your house on the line for a bank loan, and put all your eggs in that basket. Opportunities are everywhere.

You don’t need money to be an entrepreneur.

The one thing that I don’t want to cut short is that I’m supposed to be at an appointment at 1:00. I will have to leave here at 12:40. Is that okay?

We can wrap up now. It is winded down. This has been a great conversation. It is good to reconnect with you. It is exciting to hear all these things. I love the stories, the ups and downs, and the continued optimism. You are still young. I got neckties older than you, for goodness sake, but it is exciting to reconnect with you. You were part of what became the Ice House Project, which has now gone all over the world. You were one of the initial students that caused me to dedicate my whole life to this. Thank you. I’m grateful to get this story in this part of our show.

I do have this problem at home where I will buy books that I don’t always read all the time. My wife wanted me to hone in on the books that I had on our portion of the bookshelf. The Ice House Entrepreneur one was there. I opened up the cover, and it said, “To Steve, you were the original Ice House Entrepreneur.” You signed it. That gave me chills.

The presentation we did at the end of it, and it is funny, I never thought about what you said in the opinion-based way that was structured. It is the person that had an idea that never went anywhere that won the competition. You would earn $40,000 cleaning parking lots, and no one paid attention to it. The thing that got my attention when I dedicated myself to this was what you guys said to me at the end of the year.

I asked you all, “Why did you take this class? Why did you come to school an hour early to learn about entrepreneurship when you didn’t need the credit?” What you guys were saying is, “This changed the way I think. I can see opportunities. I can see myself playing at a higher level. I understand how the world works. I now know how to learn, unlearn, and relearn on my own.” That is the important thing for entrepreneurship education.

That is why you say, “You can’t take credit for it.” There were two stories you told in the class that resonated to this day. I’m sitting here seventeen years later. One was, “Do you guys realize what a magazine is?” Everyone was like, “We know what a magazine is.” You are like, “Do you realize that it is a mechanism to sell advertising space in something concrete that you can read? That is a profitable thing.” You are like, “Do you know why buildings are up in the air? Do you know why there are office tower places?” I remember a light bulb being like, “Investors paid for that. They could rent out the space.” It is not like the city put it there. It sounds stupid but I’m like, “I guess that makes sense.”

These easy, simple concepts were like, “You are right. That is why you get stuff in the mail that are advertisements.” They pay $0.05 to send it to you, but they get $0.10 from the advertiser to send it to you. One of the other ones I remember specifically was, “If I’m paying you $75 to dig a hole, and you can dig as many holes as you want to, what do you do?” Every single person in that classroom said, “Start digging.” You said, “No, you get someone to do it for $35 and find other holes to dig.” My brain is exploding.

These were moments in passing when you are like, “Stupid kids, you got to get this right.” That is a light bulb that you are like, “You are 100% right.” That is why you say you don’t take much credit for it, but there is a ton to be said about these major life realities that I have realized now in my life grown-up people do not understand. Those things clicked for me back in 2006.

My whole thing is every student needs these basic entrepreneurial competencies to adapt and thrive in the world. What people don’t realize is that non-entrepreneurial behavior is learned. Steve, this is great. I’m not going to keep you any longer. I know you have to go. Thanks so much for taking the time to share your story.

Anytime, Gary.

Important Links

• Steve Orlando
• The Wealth of Nations
• WeddingChairs.net