Matt DeLong is a lifelong entrepreneur and angel investor with a 20-year track record of launching successful ventures such as CoreCommerce and Sum Effect Software. He coaches, consults, and invests in technology startup companies, with a particular focus on SaaS (software as a service) companies.
DeLong thrives on building things, having launched 14 startups while serving as an advisor and investor to countless others. He started his first company at age 17 and has gone on to create businesses based on solutions customers seek to their problems.
DeLong is currently building trading automation software that will be the core of a new kind of hedge fund using automated trading signals to buy/sell stocks/options/etfs. DeLong continues to experiment and create as he leads his companies, while always keeping an eye out for the next opportunity to contribute to rising startups.
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Matt DeLong And His Unique Story of Entrepreneurial Sacrifice & Leading Purpose Through Real Life Trading
Hello, everyone, and welcome to another episode of underdog. Today I have an awesome guest here with me, Matt, how are you?
I’m doing great. How are you? Pamela?
I am doing wonderful, I am speaking to a serial entrepreneur here. He is a total rock star and I am so pumped to get into your story, my friend. So I start with the loaded question of what inspired you on your path to where you are today.
So I actually grew up a generation X. And my dad used to always tell me this like a Lamb of story, he would say, Matt. You need to go to school to get good grades. So you can get a good degree so you can get a good job so you can retire with benefits. And I thought no, I heard that like every week and I’m like, that is the most lame of thing I’d ever get.
So I decided I didn’t want to be average, I wanted to be above average. I don’t want to live my life just to be some average schmuck. And so that’s a decision I made when I was 18 years old. I’m a few years older now, of course. But yeah, that was it. It was just a decision I made because I didn’t want to be average. That’s really it.
I love that. And so you apparently took that very much to heart because your journey has been. So all over, we’ll reel it in from the beginning to is like what did you want to be when you grew up?
When I was younger, I wanted to be a veterinarian. But then I could see blood in my stomach would get all knotty and I would like oh. I don’t think I can handle the sight of blood and passing out and all kinds of crazy stuff. Which isn’t helpful if you’re going to be a veterinarian. So then I’m like I want to own a business. I want to be a business owner, I want to be an entrepreneur. And so my grades in high school were only good enough to afford me to go to a community college. So I went to community college for like three semesters in Orlando, Florida. Where I was growing up and I decided this psychology isn’t my thing.
Like, I would listen to Professor God at this community college talk about how smart he was and it would just drive me nuts. And I feel like calling them out and like, bro, you’re at a community college, like how smart. Are you really like, Come on, let’s be honest. Right and so I knew that if I was leaving some kind of a situation. When I was learning and I was just stepping away from that I knew I had to do something to stimulate my mind, something to learn. And so what I did was I decided you’re ready Pamela, I decided to read Entrepreneur Magazine. Every month covered a cover for 10 years and that’s what I did. So my college education cost me $240, so that’s what I did. Yeah.
Awesome. That’s so you basically just read Entrepreneur Magazine.
I did cover to cover, cover to cover that’s important. And this is back when they would send it like in the mail and come in your mailbox. You would like to just open it and you can read it is obviously pre-like early years before the internet was a thing. So I did that and when I met my wife, we’ve been married over 20 years now and had this massive stack of all these magazines. The covers are falling off and all that and somewhere around 1998 1999, I read that there is this new trend. They called it the World Wide Web and it was going to be like the next big thing. And I thought maybe I should learn something about this next big thing.
So I read and I learned I studied it as much as I could. And this is like the early internet. There’s not like the internet for dummies books out at that point in right there. Those didn’t exist. It was still so new and so I decided to learn, just like taking online tutorials. So there’s little websites and little snippets, where you can write this code. And it does this and I literally just jumped in doing that for about a year and a half. Just in any spare waking moment that I had. I jumped in and I learned how to just build websites. And so I end up getting a job doing that full time I ended up starting a software company that made e-commerce easy to use something like Shopify is today and it just took off from there.
That’s incredible. So your first business so you’re just saying it was like a software company on the world wide web, the internet. I still remember like, what I would be on was the aim. AOL Instant Messenger. Yep. Somebody would call my house phone and I used to flip out. I’m like, you just ruined my conversation with my best friend. My mom’s like I need to talk on the phone, so it’s like, it’s crazy. Like, now we have our phones in our hands, like in our pockets. And it’s just bananas, so walk me through like your first. So you went through your first business and like how you really started that one cuz I know it was one of many.
Like early on. So I learned how to build websites just in the races around the late 90s and so the first thing I did was I learned it enough. And I decided to help like friends like I printed out bands and different things. So I would like to build websites just to get some experience and practice. Build them a website here about like, my church website did little things, just try to get some experience. And then I took those and I use those like a portfolio to actually get a job doing it full time with another company that accelerated. Then what I did was I decided to do freelance work on the side.
So that was like, websites like guru.com, which is even around to this day. I would find a lot of freelance projects where people are looking for this and this is what I did and they would match you up. And I would do that and then my side business got bigger than my full-time job. That was a good year and a half or two, I was newly married and my wife would kiss her goodnight. And then I would go over like three feet over to the right to my desk and I have my PJs on ready to go to bed. I literally worked there until my head started Bobby.
You know what I’m talking about Lord do stay tired your head, sorry, okay, now it’s time to go to sleep. And I did that for like a good year and a half. So I’d work a full-time job and then do the side thing. Just took some time to get enough clients, enough projects. And from that, I started a little bitty software product that started out with like 25 lines of code up until when I sold it in 2016. It was like 2 million lines of code, it grew just a little bit and then became this big, big thing.
And over that journey, you learn so many things, and actually, that was not my first one. That’s probably the most memorable one. I think every guy in high school, everybody has always mowed yards and cut grass. That was like my very first thing, but working with the internet and computers and stuff. I just figured out this kind of quality, this grit, where most people quit. I’m super, super slow, and patient in turn to learn some of this. So it worked to my advantage in that case.
That’s awesome. You took that cover to cover basically education. I wanted entrepreneurial education, which is experience and there’s nothing like it. That you could have three MBAs and still you could be a shitty entrepreneur like that’s like experience is everything. These are things you can’t learn in school like that grit, for example, that you were talking about, like, grit cannot be taught. I don’t care what anybody says like that hustle. Your character. Like all that stuff plays such a huge role in business, especially as an entrepreneur. Especially when you are the brand.
So it’s interesting to me, like, you know, what were the first steps that you took after getting into your businesses. It’s like so many people and I know there’s a lot of entrepreneurs listening. And maybe people who are aspiring entrepreneurs, that it’s like, analysis paralysis, right? Like, I’m not qualified to do this or imposter syndrome. I’m not qualified to do this. What makes me able to do this and just hesitate on like that first bit. Because I feel like once you get into it, you get addicted. And you just hit
Yeah, it is, as a challenge. I gotta have a bigger, tougher, taller challenge next time. Yeah. So I feel like for most entrepreneurs that at least people who haven’t yet. Maybe made the plunge and started the first business, which is like a coaching call I did earlier today. I feel like a lot of people have different expectations of what entrepreneurship is. And if you look at Hollywood, it’s high fives all day and just raising a million dollars, just high fiving people all day, like, that’s how it is. If it’s anything different than that, then I’m going to be disappointed, you know. There’s lawsuits, there’s all kinds of good stuff that you have to deal with that is uncharted territory for you.
And I feel like having some level of expectations that are just super like, this is gonna be really hard. I know it’s gonna be even harder than that and so you have to jump in and figure things out. And do the work, put the work in, and obviously, you have mentors and you have people in your life that can help you a little piece of it. But at the end of the day, it’s up to you and as you know. Owning your own business. Five o’clock on Friday, when most people clock out and they go home as entrepreneurs. You still have that weight on your shoulders, even on weekends, even on vacations.
And of course, you set up systems and processes and things that it can run without you. But that way it still is on you, it’s still your responsibility. So when it works great when things are going well and then a sec will talk about when things didn’t go so well. It works great in those environments. But you really have to be a fighter and you have the grit, but you can’t give up. You absolutely can’t give up and I was talking to someone today. They’re like, Well, Matt, what happens if I fail? And I’m like, what does that mean?
When you fail and you stop trying, that’s when you fail. But you can be out of money. Like, there’s plenty of entrepreneurs who’ve failed bankruptcy before. Whenever you stop trying, that’s when you fail and I’m gonna keep going until I don’t fail. And that’s the mindset you have to have and a lot of people are looking for the easy or the cheap, you know, some shortcut. You can spend a whole lifetime looking for that. And it doesn’t really exist, you just got to do the work.
Amen. No, seriously and that’s the hard part. Like, you just got to go right into it. I tell people, I’m like, you don’t have to know at all not one bit. But you just start one step, you take one step each day towards where you want to be. If you think about the bigger picture, like yes, of course, you can get overwhelmed. And it seems so big and scary. But if you just take it one step at a time, I’m interested to hear your techniques of diving. Right into it, into the first one, and kind of moving forward from that. If you could share your experiences sort of after the fact that be.
Sure. So I think most people try to think about when they’re starting out. They try to think about I need all the green lights to be green between here and where I want to go. And you don’t really need that if you’re waiting for that time and that’s never gonna happen. You know, like, if I was driving to Pam’s house, I only want to go. When all the lights turn green and they’re all green in a row. Then I’ll go, you just need like 50 feet or 100 feet. You need some light, you need to see what the next step is. Right and that’s really all you really need. And so for me, what I did was I got the first thing I did after I learned how to do the skill itself.
I decided early on that I needed someone. If I’m busy doing the work, I need someone to sell the work. Most entrepreneurs are freelancers, they have this peanut butter and jelly and then steak and potatoes. And they like this roller coaster up and down in their income. Same thing with real estate investors at times. And so you have to have someone like you have to have some consistency. So I decided to hire a salesperson to help sell some of this software that I was working on and building. It worked out great and he worked with me for nine years and we ended up growing a company together. But that was like the first step and so in Entrepreneur Magazine. There’s plenty of case studies about hiring and firing.
And I had a pretty good feel for how all that should work. But there’s nothing like you said, jumping in and figuring out. When you hire someone, you’re like, this person is going to come in early and they’re gonna stay late. And they’re gonna ask for more assignments. Nope, a total opposite some a lot of times that happens. You can do assessments and testing and personality. Now there are all these exams and tests before you hire someone. But at the end of the day, it really is a lease in my mind. There’s some element of unknown how well they’re actually going to work in the role.
They could be a superstar in their old company, it doesn’t mean. They’re going to automatically be a superstar here at this company. You just have to kind of work through that. So again, for me, the first thing I did was look for a salesperson and one of my clients. That was a client at the time of a company I was working for previously. They were about to go under and they just announced it to everyone that, hey, they’re closing up. And so one of their salespeople actually reached out to me, like the same weekend when I decided. I was going to hire someone and so it just happened to work in my favor.
That’s amazing. And you know, what’s insane? It’s like the step 20 codes to 2 million is pretty ridiculous. That honestly, like it’s insane.
20,000 lines of code that 2 million lines of code. Yeah, it’s a lot.
That’s a lot. But you started with one step at a time. And that’s what I try to get people to say, like, when your fitness instructor says you do a workout. If they’re like, okay, you’re gonna do 100 of these, you’re gonna be like, oh, but then when you say 10 sets of 10. Yeah, all of a sudden, things shift a little bit, which is super cool.
Oh, man. And you’re like, you get 60 seconds of rest in between each set. Right?
Right. exactly, right. The pause is really important, too, because the entrepreneurial burnout, you try to do everything yourself, you’re going to feel that it happened to me. You know, I’ve made my mistakes, my entrepreneurial mistakes. Here I didn’t properly budget and I was credit card debt up the wazoo. And then like, hurt my credit because I just like, some things were late.
Because you just put it within you, you’re trying to build a dream and then run all this. And then try to get bigger and do this and be that you know. It’s different, especially when you run multiple businesses. Absolutely, so it’s super interesting, super interesting. So like in your entrepreneurial endeavors, you could talk about them and sort of what you know, because you have 14 of them correct? Oh my god, if you could walk us through those and then like. Mistakes you’ve made throughout the process would be.
Yeah, so they all had they’re all in slightly different industries. And for me, like mowing yards was something that I did write out right. During high school, I liked extra cash. I think every kind that was one that I did I used to sell. While it was like a big game, like Beef jerky, it wasn’t beef jerky, it was like an ostrich and Gator and kangaroo. It’s crazy stuff and in each business, you have things that you learn. And I think I feel like failure is part of the equation here and at least in high school and middle school. They teach you not to fail, like don’t make mistakes, that’s bad. But I feel like it really needs to be part of the process.
So like learning, making mistakes, losing money, it’s as long as you learn from it and you move on, right? Because like, what’s the most expensive mistake you can make? It’s the one you don’t learn from because then you make the mistake, you pay the price. You make the same mistake again, you pay the price again. So I feel like failure is part of the equation that most people don’t embrace. And so that’s actually my superpower is I’m really good at doing things wrong. I will do wrong really, really quickly and then I’ll figure out how to do them.
Right. It’s like, I figured out what not to do. And now I’m a little closer to figure out what I should do and so it could be hiring, it could be, you know. Should I even be in this business, to begin with? A low low-margin business that has lots of lots of manpower that’s required, you know, like, everything has to go perfect. Just the breakeven, you know, is that a business I should even really be in. And so all the businesses that are started cost less than $10,000, to start every single one less than $10,000.
That’s an awesome risk. Because there’s people that put it, oh, my God, like restaurants, for example, building out a kitchen is like three to 500 grand.
Just to clarify 10,000 out of pocket, just to clarify. So sometimes I did have loans I did borrow, you know. I had personal lines of credit and I had, but I think like each venture that you do. Even if you stick, like you try your best for a year or two and things just don’t work out. It’s not the end of the world, It might be bad. But it’s not like disasters, disasters would be like you lost everything and you’re in jail, like fraud or something like really, really bad. That’s hard to come back from right. And you’re kind of stuck in a really bad environment that you can’t just snap your fingers and overcome easily. But each little business that I did was I had a web design company.
Each one that I did had different lessons that they learned along the way. Whether it’s hiring, whether it’s a process, whether it’s a contract. And make sure you have everything that you want to do in a written contract form. Not just handshakes and there’s tonnes and tonnes of lessons. We spend hours talking through each of those. But I just feel, I feel like, at the end of the day, you just have to have this really tough, tough mindset. And you have to be willing to do what it takes and whatever that looks like, right. Sometimes it’s an open cheque book on your time, right?
Because it is we can all invest time or we can all invest money. And as you get older, you’re investing your money to get your time back. Right and so, at least for me, I feel like at the end of the day. I’m trying to become the best version of myself. I don’t know if you’ve heard anyone say this before about I feel like maybe at the end of your life. You get to meet the person you’re like you’re supposed to be right and like. Do you have anything in common with that person? Are you total strangers? What advice would they give you, are you identical twins? Like that’s what I’m, that’s what I’m working on.
And because I have a software background, I think the version I like is like the 7.1 version. I’m smarter, faster, and healthier, I’m richer, but I got a little more mileage than my previous versions. Yeah, so I mean, that’s really what it’s about is trying to be the best we can compare notes on projects. And did you make more on this one, I made it more like we could do that all day every day. But at the end of the day, it’s me versus me like me this year versus me last year and yeah, it’s been with COVID everything.
It’s been just wild for most people. But some of us who are in the right place at the right time are prepared, It’s been just crazy. 3x year everything has tripled. Right and so I mean, that’s where you want to be, you don’t want to be panicked, and Corinne and just things are going crazy. And put your head in the sand. You just want to be prepared, ready to go, have the right mindset and you’re waiting for those opportunities to cross your desk so you can pounce.
Matt’s Biggest Lessons Throughout His Entrepreneurial Ventures
Well, that’s the thing is like, you know, as an entrepreneur, you got to be fluid. You got to be ready to adapt, you got to be ready to pivot at any point in time. COVID was a major test for anybody who was stuck in their ways. Traditional wasn’t thinking of the digital world. I had a lot of issues during COVID, you know. Or they’ve had to reinvent themselves really quickly or those who have stood out on top post COVID are the ones who have adapted. And that’s the crazy thing and I mean, there’s so throughout your entrepreneurial journey. You’ve adapted a lot and I definitely want to hear, because here’s the thing to me, failures. Parentheses are just lessons.
So what were your biggest lessons? You’ve learned throughout your entrepreneurial ventures. And the reason why is because I know there’s entrepreneurs who are going. Or have gone through this and they feel like parentheses failures, but they’re really not. So if you have some stories that you could tell about different lessons that you’ve learned be super helpful to do. Because I always like to paint the picture of like, hey, this actually happens. Like, yes. You mentioned before our call that 14 businesses, but only how many of them sold? And how many of them? Did you sell more of them? It’s a pretty good ratio, I think. I don’t know. Yeah, but like, it’s so important for people to hear this because then they don’t feel so alone.
Everyone’s got to be a winner. Yeah. It’s funny. When you start a business, you feel like it’s gonna be the one but you are a year two, three down the road. You’re like, maybe this isn’t the one. Right. But that’s part of it. So one of the things that I one is that most people I’ve told a story to a few times. But I’ve actually passed out three times from stress three times. And twice while driving. They don’t try this at home, kids. So when you mentioned pivot, that word pivot and 10 years ago, we called it a near-death experience. I’m joking a little bit, but in business, we actually had one of our early iterations of my software company where we had a piece of software. You could download the installer.
And so in 2008, we decided to pivot from like a downloadable piece of software. The software as a service, which is what you know, now. Which is everything’s out in the cloud and you just pay a monthly fee, you don’t really download install anything. So we pivoted from that into what is now software as a service. And in 2008, we felt like salesforce.com was out, right. That was probably like the Mack day early original software as a service. You remember, they used to have like a little icon, it’s a software with a little Ghostbusters. Like Excel type things, like no software, even though they’re a software company, it’s kind of funny.
But the idea of downloading software and installing and running on your computer is like old school. Like having it live in the cloud, you just log into it, that was like what we were kind of adapting. So during that, what I did was I took out a personal Guaranteed Loan of $200,000. And what caused me to just the stress level, just go way higher than. What I could handle at the time was we launched April 1, April Fool’s Day of 2008. And within a month, we had three customers paying us 2999 a month. I had this personal gain and for those of you who don’t know. A personal Guaranteed Loan means the company goes broke. And I personally have to come out of pocket and pay that back.
So the company can go broke employees and go get another job. But I have to dig my way out of that and try to find some other work. Or some other way to generate income and so I remember just driving down the road. And I was meeting my wife and kids, they were camping. They drove up a day or two early to meet my father-in-law. We were somewhere in Kentucky and I remember feeling this like black and white color vision. Just going away and turning black and white. I’m like, wow, that’s interesting and I was sweating and I was like. What is happening and I remember going down the road about 7080 miles an hour.
And I looked in one of those rest areas, and I saw an exit, you know. Half a mile and like I need to pull over like this can’t end well. So I was literally going 80 miles an hour, the air was cranking I was sweating like crazy. And this is like the summer so it was cranked 100% and then, I’d been on the road about an hour, hour and a half. I remember pulling over to the side of the road, opening the door. Taking two steps in the just face plan now, as I remember waking up and there’s paramedics standing over me and the first thing I did was I’m like Where’s my phone?
They ended up doing, like, EKG and all this stuff. I mean, they gave me, okay, to either sign something I refused to seek medical treatment any further blah, blah, blah. And then they do tests on me like days later after I get back and they said. A stress they tip you upside down they do all this stuff make you run and they said. We will find anything so it must be stressful. And literally the very next year, the same exact it was around July 4 weekend, the same type thing. It happened again the very next year and it was the same type of thing. I wasn’t on Interstate I wasn’t backroads.
And I remember calling my wife. I said, honey, it’s happening again I’m here at this intersection. If I don’t come home blah blah and the same thing happens and I feel trying to internalize everything is not the healthiest thing. Where I’m like, Oh my gosh, the way the stress of that was just unbearable for me, like, Pam. How do you know if you’re pushing yourself hard enough? If you’re not like passing out from pushing yourself so hard. It’s like your mental capacity exceeds your physical capacity at that moment. And so um, you know, everything worked out, okay, I didn’t know anything. Disastrous happened.
That was a really interesting time of life because that was the start of the company. Really growing and it didn’t seem like it was gonna grow and it was a slow start, you know. Have you ever seen those races where people are running? And it just doesn’t seem like it’s going very well for certain competitors like that guy, that underdog, I don’t know. Maybe he’s the loser maybe, but he ends up being the underdog and you’re like. Wow, I didn’t see that coming. But shame on me for not believing in that person for whatever reason, you know. If you’re talking about physical athletes for whatever opinion you get from them, just looking at their physique or whatever.
That’s that entrepreneur burnout, that’s without a doubt. How did you learn to avoid that in the future? Because I’m not just an entrepreneur, but everyone’s overworked these days. And that’s also working from home. So like, lines have been seriously crossed. Anybody in the corporate world, even their boundaries are being crossed out. Because we’re calling that if it’s one and the same. It’s one of the things that were some techniques that you utilized.
Right, it’s a great question. So I started doing more physical exercise. Oh, and I felt like, I really needed to do something to get out of office to get some fresh air. And just like thinking about as crazy as it may seem, it’s not really all that bad. So I used to have a pastor, he would say, it’s never as bad as it seems. And it’s never as good as and it’s so interesting to think about. As bad as you may feel that things are going, it’s not always as bad as you think. I had a mentor at the time and he’s like, Look, man. You’ve been through more stressful things and your 30s and he was in his 50s at the time, like, I need ask for this.
I just somehow it just follows me around, but I have to deal with it. It’s like, I didn’t ask for it. But I’m responsible for it in a way and so I ended up buying a treadmill. And I ended up just putting in time on that consistently every day. So a lot of people hit the gym, where I do more gym work now these days. And so I just do something to get away to kind of like, get all your frustrations out in like a healthy way. You’re not going home and kicking the dog and yelling at the kids and the wife, you’re not doing that. But you’re getting all the frustrations out in a healthy and productive way. So that’s what I am doing for that and that situation.
I love that. And thank you so much for sharing your experiences, because sometimes they aren’t the greatest. You know what I mean? Sometimes those lessons are not the greatest. But again, you learn and you keep moving forward. And now, with that being said. There go the lessons. But now what have been some of the biggest moments in your businesses, the most like successful moments for you.
I joined real-life trading at the end of 2019. And this was, I guess, a few months before the whole COVID thing happened and our mission is to enrich lives. So we help teach people how to trade the stock market and it’s been an amazing, amazing journey. We’ve like three acts the whole business since I joined at the tail end of 2019. And this idea of and I didn’t quite get this early on of this business of enriching lives. But I actually traveled with Jeremy quite a bit. We go to different cities and meet up with locals, like, we go to Chicago, or Orlando, or wherever. We’ll meet these traders that are in our group who’s been in our community for months or years.
And they’ll say, I watched your free content for years, I started making money, I was able to pay off my student loans. I started making more money than my job, I was able to leave the job and I do this full time. And now give back to my community and like all these things that you have a part of, you know, and help enrich lives. So what we try to do is we try to teach our community, our traders. What is the reason you really want to trade and most people? If they’re honest, I will say I want to make extra money, which there’s nothing wrong with that. But if you have that kind of a reason compared to the best one I’ve ever heard, which is like a tear-jerker.
If you’re ready. This lady, she was always her. She had things like, she had a college student, college-age student for a daughter and she said. I want to break the curse of poverty on my family and provide for my kids and grandkids. And that was her why and now if you compare like I want to make extra money, and that kind of life. Which one do you think is gonna have more grit? When things get tough to kind of push through and continue? You know, is it cry for five minutes? Okay and then keep going. So that whole powerful reason why she’s doing it and she’s become a phenomenal trader just changing her life and her family tree. Well, she’s literally doing that right now.
And so it’s not really about the money and growing companies as much as those stories. We hear those not always that powerful stories many times a week and people will write testimonials. And send us all the stuff and we have about 30,000 students that are in our database right now. We’re actually doing some other things as we’re growing but yeah. I think, the most meaningful thing for us and as you know, like having money doesn’t necessarily change who you are, just amplifies who you already are.
So if you’re a kind heart A generous, nice caring person with money. You’re going to be a 10x version or 100x version of that. If you’re a jerk, you’re rude, you’re, you know, you’re just impatient with the waiter. Like all the things that, you know, with money, you’re going to be a 10x version of that. And I feel like that’s really the perspective, being able to ritualize and not just making money. So you can buy yourself some silly toys like we can all go buy toys. But it’s really about being a difference and making a difference in the world.
That’s awesome. And in the trading world to like, because there’s those Instagrammers with those spam, spam comments that drive me nuts. But like I heard you, I heard about Jeremy and I’m like, okay, I love these guys. They’re super cool, but it was really amazing to see seriously. How you have started 14 businesses and been super successful.
All four of them, the other 10 you know, whatever they were lessons. But now you’re in a space where you want to create that impact. Because you do good and also make money. And that is like a barrier to be broken right now just in the world. Because some people think like money is the root of all evil? Well, it’s really not. It could be if you look at it that way. But you can also use it as a force for good. Like you said,
That’s right. And money. Money is like it can be a tool, right? It can be like a brick, you can use a brick to build a hospital, you can use a brick to go through a window, like. It’s how you use it really more than the thing itself. It’s just a tool. And you can do all kinds of evil in the world. Or you can build schools and hospitals and all kinds of things with Brexit, it really just depends on how it’s being used
Throughout all your businesses and everything that you’re doing now. What has been the top tip or top three tips of being an entrepreneur and what you’ve learned there your lessons, your biggest lessons?
I guess. Yeah. So one of them has been to give back, as we touched on this briefly is the idea of using money. To help make a difference in other people’s lives. And a lot of times, it’s not always about the money too. It’s about just spending time with people who feel like all hope is gone. if you’ve ever met people who have just been beaten up in entrepreneurship. They’re like, I’m just this is it, once I shut this down, I’m done. And spending time with those types of people. I think it’s kind of interesting because you can like it doesn’t have to end this way. Like unless you quit, of course, it’s up to you, right.
And so like being able to spend time and pour back into people, it’s super, super impactful. The other thing that I feel like was a great lesson is building a really, really powerful team to help accelerate your company. So like my rule of thumb is when I hire someone for a certain role or certain job description. I want them to do 85% or better than what I could have done right, I feel like they don’t have to do exactly what I would. Because you know, there’s always the people who are going to micromanage. And the people who are going to be perfectionists which drive employees nuts. But if you say, here’s what this role looks like and you define it really well.
And you give them an idea of what that should look like, if they can do 85% or better, I’m fine with that. Now I can count on two hands, how many people I’ve hired that did even 100% better than what I could have. It’s rare and those are the people that I’ve come across. That is just it’s very, very, very rare to have someone. Who can do a really, really good job and you hand them responsibility and they can take and run with it. It is not as common as I’d hoped it would be, so building a powerful team. And then if you’re working with people you really want to work with, I think it is super impactful as well.
So I’ve worked as a software company, versus working with real-life training. It’s kind of a night and day, so working in a software company. Everyone’s like, well, how much do you know, what does this project look like? It’s all money, money, money. And then working with real-life training, we have people who literally volunteer to help us with things. Because they love our mission, real-life trading is more of a company, but it’s more like a mission than an actual Corporation. So for us, it just is pretty interesting.
When you’re working with other people who support the big mission of what you want them to do. The mission can’t always be about making money, because how do you get your employees. I think your employees fired up about making money if that’s like the end-all then why. So being able to make a difference in people’s lives and seeing the comments. And the reviews and all the video testimonies, all the stuff that we see over a week. It’s you know, that’s very, very, very meaningful, even more than the money in my mind.
Amazing. And now an even tougher question for you. What would your older self tell your younger self, based on what you know now?
I would tell myself to chill out and not take yourself so seriously. So I feel like there’s two kinds of people in the world. There’s purpose-oriented people and fun-oriented people. The fun-oriented people need to figure out how to have more purpose. And the purpose-oriented people need to have more fun. So that’s what I would tell my younger self is being super purpose-oriented. My younger self, I would tell him to try to have more fun and chill out. Because as you know, life is short. I’ve been telling you all my crazy stories of being in the back of the ambulance waking up unconscious. But yeah, it’s, I feel like life is really short. And you don’t really know how much time you have left.
You have to be super, super intentional with how you spend your time, right. So for some of us, we’ve actually done this morbid exercise where you write your eulogy about what you want people to say, at your funeral. Have you ever done that before? That doesn’t sound like fun. But I literally wrote out my eulogy, you know, talks about what I want my life to be about. And I want to make a difference in the world and so when you have that kind of super lifelong clarity. It helps filter, what is and isn’t important, what is an opportunity? What’s a distraction?
So there’s plenty of opportunities that come across my desk and like the past six months that I said, No, thank you, too. Because they were a distraction from what I really am trying to work on. The things I’m trying to work through or accomplish in life. And then there’s somewhere I said yes to because they absolutely line up with what I’m trying. What I want my life to be about and is a little bit of a morbid exercise. And it’s not a whole lot of fun, but it does, it does give you some serious focus and some serious clarity. But then everything filters through that.
Yes, I need to try that. I need to try writing that because I feel like yeah, I don’t know. Yeah, not to be morbid, but I tell people all the time, I’m like, you know. You have one life and when it’s all over, what, what are you leaving behind? And they’re just like, Huh and I’m like, you can’t just live to live, you got to think about generations from now. You have to think about all these other different elements, like people are counting on you and you don’t even know it.
Exactly, exactly. Um, for like the young up-and-coming entrepreneurs. I think one thing I always like to leave with people. And this is no matter what your bank account looks like, no matter where you live in life. If you’re in the poorest parts of Africa or if you’re in America. How you spend your free time is super, super important. And so when I sold my software company, the new buyer. The investor who bought it, he and I collectively agreed to work together to hire a CEO to replace me. Because I was moving on and we end up finding this the CEO that we both could agree on and we went through.
We talked to dozens of people and we found the CEO that we both could agree on and the first thing he said to me, he goes, Matt, let me see your phone and I’m like. Okay, so I’m locked in hand it to him and he’s scrolling scrolling. He goes, Okay, we can do this and I’m like. What just happened? And he’s like, I’m looking for video games on your phone and he found zero on my phone. Like, what does that have to do with finding video games? And he said, Well, I want to make sure that I’m working with people who aren’t time wasters. People were just filling time like you got 10 minutes here, 20 minutes there, you’re just filling it with something.
He’s I want to find people who are learning, reading, listening to podcasts. They’re like investing their time and they’re building a new version of themselves. As I read this, this blog article on this, like, very same topic about using your free time to improve the future version of yourself. Even if you’re 13 years old, 14 years old, and you live in the poorest parts of the world, you can still do that. It doesn’t mean you can still learn, you can still read, you can still improve yourself. And it was really shocking to me when I wrote the articles got fun, quora.com. I was surprised how much haters and trolls I’m like, what’s wrong with improving the future version of yourself? And they’re like, Well, Matt, do you have these?
I’m like anybody can improve. Like, why is that a bad thing? Pretty sure. The Facebook CEO, Mark Zuckerberg, Elon Musk Tesla. See, I’m sure they’re not spending their free time watching cute cat videos on Facebook. I’m pretty sure just a guess I don’t know personally just to guess. They’re like spending their time improving for the future version of themselves, not just in a time-waster. And so that’s what the whole thing was that he wanted to look through everyone’s phone to see who’s the time wasters. It never occurred to me that I had no idea. That’s what he’s even doing. So I passed the test. Yes, I want to work with these guys. And it became you know, we ended up hiring him and kind of went from there. So yeah, it was pretty crazy.
Amazing. That’s hardcore, but it’s really true. Wow, that’s amazing and so you mentioned real-life trading. And that’s sort of what you’re, you know, that’s what you work on. Now, day in and day out, which is pretty amazing. But definitely tell me what are you up to in that realm. You mentioned that there are courses for all these things. So if you could give us sort of an excerpt about what it is. And then also how they can find you have different programmes. That are offered anything that’s coming up for you in the next like six to 12 months.
So real-life trading helps teach people. How to achieve financial freedom and it’s done with trading stocks and ETFs, stocks, options, crypto. And so we have a handful of free courses. So if you’re interested in learning how to trade the stock market. We have a beginners course and an intermediate-advanced course. They’re all free for you to sign up on reallifetrading.com and go to our website and it’s right on the homepage. The first thing you see is beginners course and you can go in and you can fill out your name, email, and then boom, you pop right into the course. And it’s based on like five modules, so you complete module one and it takes about 10 hours to go through the whole entire thing.
But each module is about two hours. And then you take a quiz at the end just to make sure you’re retaining what we taught you. Then you unlock like the next module and you go through until you complete it. And so that’s that’s where most people start. We do offer online courses like that we do offer live in-person training. So this year, we were in Charlotte, North Carolina for a week, we’re in Miami and at the end of March. We’re going to be in Lake Tahoe in the middle of July. We do the same type of teaching but in person and so we’re super excited about Lake Tahoe.
And then we have a money grows on trees event in October. Which is just all mindset and your beliefs about money and finances. And how you can shift and make small mental changes to see things very, very differently. So that’s coming up October 23, to 27th and that’s Turks and Caicos, so those are like the live events that we do we offer. We also offer a mentoring group. So a mentoring group, if you think about like a small study group of six traders. You plus five other traders and you have a mentor and you meet once a week, usually the same time every week. Like Tuesdays at seven or Wednesdays at nine whatever the same time. There’s specific topics that people will mentors will lead you through.
So there’s things just for beginner traders, there’s for people who are interested in learning to trade like advanced strategies. Like there’s specialties that you can sign up with. If you want to learn how to trade futures, we have some specialists who do just that. And that’s what the mentoring groups doing. It’s eight weeks long, so you go about an hour and a half. And it’s eight weeks, you need the same time every week. Then we also do personal coaching, so if you want to have like a one on one call with someone, any of the mentors who teach in these mentor groups.
You have a one on one hour session with them, maybe walk through specifics of maybe some trades, you’ve taken that, you know. What could I have done differently, that kind of thing you can do that as well. And so that’s kind of come that’s all what we’re doing now and what we’re working on. We launched in January. I was on a private island in the British Virgin Islands. And Brittany Turner asked the question, what is one cause that you would like to improve in the world? So I said to eliminate human trafficking because I have two teenage daughters. I said that and literally February the next month, we’re setting up a nonprofit, which is a real-life foundation.
And then in March we’re doing each of our live events. We do a fundraiser dinner. So we did a fundraiser dinner at the end of March we raised $29,000 and a dinner. Yeah, it’s pretty cool, our very first dinner, so we have to set the bar higher every time. And our benefactor was the operation Underground Railroad, which they do. It’s like a civilian group that runs military-style operations to work with local countries and local law enforcement. To get them to arrest the perpetrators and free the victims of that. So yeah, that’s super rewarding to raise the help be a part of that and then beyond that, what we’re doing. It’s gonna be out later in July as we’re working on some real estate investing courses.
So we have some subject matter experts, people that are in our community right now who do flips and rentals and multifamily. And we have a big list of house hacking and Airbnb and self storage and triple net leases and foreclosures and all kinds of all types of things. I think 17 or 18 courses that we’re putting together. And we’re working with a subject matter expert who’s part of our community already. So one of the things we hear besides us trading is what are some other avenues. Some other revenue streams that we recommend real estate investing.
Last summer, my teenage daughter, who was 17 at the time. Wanted to learn how to flip houses so she and I bought a house and we flipped through we worked on it together. And it was a great experience for us. She wants to get her, she wants to do more real estate investing as a career now because of that. And so I am working on a book called what entrepreneurs teach their kids and then later this year, we’re relaunching a whole new thing. Everything that we’ve done with real-life trading with free courses and personal coaching and mentor groups. We’re doing the same thing with real estate investing.
And once that’s completed, we’re going to do the same thing with real-life entrepreneurship. We’re setting up an investment group to make investments into people who go through our courses. And now it won’t be like a venture capital but kind of like an angel. We’ll meet and make some small angel investments into people that we’re working with. So yeah, it’s super cool, super exciting. It’s been a wild journey. All the things we’ve been able to do in the past year, year and a half and COVID didn’t beat us down you know. We bounce back stronger than ever. Like, unfortunately not everyone can say that but yeah, it’s been amazing.
Absolutely incredible. I adore that. Now everyone’s needs to know where to find you and your awesomeness.
Yeah, so I’m on Instagram and Twitter math along with nine zero on the gramme. And if you guys want to shoot me an email it’s firstname.lastname@example.org.
I adore what you’re up to and your mission and just your passion and you’re so inspiring. And I just can’t wait to see this all take off for you guys. It’s gonna be so amazing and I just want to thank you so much for being here. Today. You are a little rock stars.
Tune in to the episode to hear the rest of my incredible interview with the amazing Matt DeLong.