Why do you want to become an entrepreneur?

As an entrepreneur, you have to have thick skin, a strong stomach and be comfortable with the idea of “being uncomfortable”. You have to learn to adapt to changing environments…and most importantly, have GRIT. That “I will die before I quit” toughness is hard to describe and out of reach for those not fully committed.

Over the years, I have met, hired and worked alongside some of the smartest people and business people I know despite having graduated high school with an 8th grade reading comprehension. I created my own destiny, even though I dropped out of college; read 10 years worth of Entrepreneur Magazine cover to cover and have read 2–3 books a month for the past 20 years. I sold 4 of my 14 businesses for a decent profit, had the privilege to travel to some of the most spectacular places on earth and invested both time & capital into several other companies.

1) How have your priorities changed from when you first started?

Over the years, I have shifted my focus from seeing everything as an opportunity to more of a focused lens by further defining what I want my life to be about, you know, the things they will say about me at my funeral. The only way to do that is to get super clear about the vision for my life. I have learned from being successful, that all the money in the world doesn’t matter if you are sick all the time or if you are alone. It’s hard to hear that truth when you are knee-deep in business debt and everything seems to be failing. The benefit to having clarity and a vision is that it also becomes a filter to the projects and opportunities that I say “yes” to and those that I turn down. Huge book deal opportunity? Does it fit into my plan, yes or no? Speak to the University of Illinois young entrepreneurs? Does it fit into my plan, yes or no? It makes decision making a breeze.

2) What are some of the best books that have inspired you during your career?

If you want to see a little bit about how entrepreneurs think vs. how a w2 employee thinks, read Rich Dad Poor Dad and Cashflow Quadrant by Robert Kiyosaki. Those books are so down to earth and will shift your mindset around how you look at money and assets. To this day, I still re-read both books every few years and find something I missed before, sorta like rewatching a movie a 2nd time.

Once you get a small business going and start building a team, books like Good to Great by Jim Collins, Execution, the Discipline of Getting Things Done by Ram Charan and The E Myth by ​​Michael Gerber gave me the right perspective to focus on things that really matter and get to work on building my business vs. working in the business.

3) What advice would you give to someone who is just starting their journey as an entrepreneur?

Most fledgling entrepreneurs focus on outcomes and goals, rather than focusing on solving a problem, adding value and making a difference. I’m not saying outcomes and goals aren’t important, but unless you solve problems and add value, you likely won’t hit your goals. For example, if you want to lose weight, standing on a scale twice a day won't get you there, but putting in the workouts and measuring with a scale will. Don’t focus too much on the scale. Identify what really matters to your customers, what really makes a difference, then put all your time and energy into that. It’s so easy to get off track by this or that and spend years focusing on minor details. The main thing is to keep the main thing, the main thing — so do that.

Money doesn’t change people, it simply amplifies who they already are. So if you are a jerk to the waiter, with more money, you will be a 10x version of that person. If you are a caring, kind and compassionate person, as you grow and build wealth, your kindness will amplify 10x, and you will start to see that you can actually make a difference in the world. This is why we launched our non profit Real Life Foundation in 2021 to raise money for causes that are important to us, like fighting human trafficking, cancer research and world hunger. Not only can we make money, but we can be a force for good and use that money to make a difference in the world.

4) Can you share a few more details on one of your biggest challenges and how you overcame it?

Being an entrepreneur isn’t all high fives and wins all day every day. Several years ago, I was serving as a CEO of a software company. We had a team in London, Nashville and India, we were growing, winning awards, life was good. We were bringing in millions of dollars in revenue, setting records, and things were on track. Then something unexpected happened, and everything changed in 2 seconds. We were hacked. Over 250,000 credit card numbers had been stolen.

You could say that situation wasn’t my fault, I didn’t ask for it, but it was my responsibility. This event, that incident, set off a cascading effect. A chain reaction of staff leaving, business relationships souring, and I brought that stress home to my family.

There were endless months of stress for me personally and my team, it was relentless. Eventually almost half my staff quit — we got death threats weekly. Then my business partner left and started hiring away my remaining staff. It seemed in those moments that I was at the bottom of a pit with no way out, I felt trapped. But I was really forced to revisit the reasons “why” I wanted to start all this in the first place. I had to get back to the basics of “why” I wanted to be an entrepreneur and although it was tempting to burn what felt like a train wreck to the ground, I still felt like we had something of value and customers that needed our help.

In that dark time, I realized that my thoughts were produced from my mindset and my mindset was produced from my beliefs. Was this really salvageable? At that time, I had invested a significant amount of time and money and determined that regardless of how dark and impossible it seemed, if I wanted to turn it around, I would find a way. In a few years, we turned things around and were back to being profitable again, better than ever and it returned to being fun again.

5) Who is one of your biggest role models and why?

Jesse Itzler is one of my role models, not only because he’s an awesome business guy, but because he is a down to earth, no nonsense family guy that I can absolutely relate to. I’ve met him in person numerous times at endurance events and he’s exactly like he looks on Instagram. Oh, and we both like endurance events and building a tough mindset. As crazy as he may seem to a normal person, I totally get him, we are cut from the same cloth.

6) What made you decide it was time to give back and help others succeed by joining the team at Real Life Trading?

For years, I had a personal connection with trading stocks and it seemed like such a basic idea to manage your own portfolio vs. using a money manager. Learning to trade stocks is really more intimidating than difficult and most people mentally elevate money managers as seeing and all knowing. I’ve talked to several people who have a team managing billions of dollars, but answers to simple questions about the stock market seem to evade them. It's easier for them to take my money and put it into a mutual fund, get pitiful returns, take their fee and repeat. So, in 2016, after selling my software company, CoreCommerce, I joined Real Life Trading after I determined trading stocks is a tad harder than just handing my money over to a hedge fund.

When I join companies as an owner/investor, I ask myself 3 simple questions.

1. Am I working with a team I want to work with? That stress and long hours are easier when you’re working with a fun, competent and experienced team.

2. Will I be working on a product/service they are OBSESSED with? I don’t want to work alongside people that aren’t passionate about what they do or are just working there until they find a better gig. Success doesn’t happen overnight so everyone has to be committed to the end goal.

3. Will I be working on something that really matters? This last question usually fails the test for most companies. This idea of real purpose means that it’s important work, we aren’t just selling things, we are making a difference.

The heart wrenching struggles, the tear-jerking stories we get (here at RLT) on a weekly basis are plenty of fuel to keep us going while we help people achieve financial freedom. As you may know the mission of Real Life Trading is to ENRICH LIVES. That may not be your company mission, but doing something that really matters is important to me. (3 things to look for when JOINING a new company)

The Struggle is Real

Over the years, I have been sued by clients, experienced dishonest business partners and employee theft, had hackers break in and steal credit card numbers, have not had enough money to make payroll, clients physically threatened me and I’ve had to go without a paycheck for an extended period of time. I’ve had staff quit and start recruiting remaining staff away and have accrued large amounts of debt that I had to “personally guarantee”. Of the 14 companies I started, all but 4 (sold) were shut down. I’ve hired and fired more people than I can remember. When the company lost big $$ in 2011, my staff suggested we borrow money to pay their bonuses. During this period of entrepreneurship, I physically passed out / blacked out twice from all the stress. See where the strong stomach comes in?

I would do it all over again too, what an experience!! I joke to friends that I have an “MBA in stress management” from all of it, but at the end of the day, you can only play the hand you're dealt and not whine about your hand. If I knew all of what I would have to endure, I would have probably steered clear of it altogether!

As Kenny Rogers says, “You gotta know when to hold them — know when to fold them” :)

Hope that helps.

I joined Real Life Trading as CTO and co-owner in 2019

Matt DeLong