3 Lessons I Learned Going from a Jail Cell to Real Estate Mogul

People often assumed that if you’ve amassed wealth and financial freedom, you start with some sort of supernatural ability or were born with an advantage the rest of us don’t have. Sure, that might be the case for a select few, but certainly not for me.

My story begins with a literal wake up call—in jail. My life had spiraled out of control after an arrest in college. I was looking at spending more time behind bars than just a couple of nights. It was the most scared I’d ever been. But when the case was dropped, I knew I had to fully commit to my second chance.

At this point, building wealth or designing a life of financial freedom didn’t concern me—I just wanted something to get back on my freakin’ feet. I humbly accepted a job cold calling for a small startup. After working my way up and getting a view from the top, I realized that what I saw in front of me only lead to a life of limitations both in earning potential and in freedom. 

I wanted to be my own boss and design a lifestyle where I could be in control of my wealth. Working my way up the totem pole in a corporate office wasn’t going to cut it. I sat down and mapped out all of my goals and what I needed to achieve them. Then I started ticking off boxes for different careers. 

Real estate checked them all.

Since then, I’ve flipped over 160 homes, built a portfolio of highly lucrative rental properties, put together one of the nation’s top performing teams. Now, I teach others to unlock their own success.

And when I’m asked what it takes to succeed, not just in real estate but in any business, I always tell people these three things…

1. Be Disciplined

Everyone knows the story of the guy who worked non-stop to make his dream a reality. My passion for building a career in Real estate quickly became an all-encompassing obsession. I was clocking 20+ hours a day, eating crap, and neglecting important relationships. 

I had a one-track focus. Make money.

It wasn’t until I joined a mastermind of other millionaires that I realized money in the bank does not equal wealth in life. These guys had lots of zeros on their bank statements but seemed to value only that. I learned some invaluable lessons from this group, but couldn’t help notice that they never seemed to talk about their families or adventures they had traveling. They seemed stuck on that same track as me.

Relentlessly pursuing wealth without discipline is a quick way to burn out and lose focus on what matters to you. So how do we make sure that doesn’t happen?


Before we fire up our engines, we need to be clear in what our definition of wealth is. For me, it means security for my family, but also the freedom to share experiences with them and to help others unlock their potential.

So I know what I want. Great. But discipline is a two-headed monster. You don’t need just clarity. You also need execution.

Since freedom is one of my goals, I need a way to build passive income (what I like to call mailbox money). Therefore, I began investing in rental properties. Now, I can take time off and travel with my wife and kids and not worry about missing out on potential earnings. And this is just one example of how being disciplined through clarity helps create a plan of execution. You can use the same method to organize and accomplish weekly and daily tasks, as well as larger and long term goals.

Motivation and discipline, day in and day out, are what move the needle forward. They are what turn our mindset into a habit. 

But even with clear goals and motivational gas in your tank, you still need a direction in which to drive. My next piece of advice is to seek out someone to help show you the way.

2. Get a Mentor

Like an entrepreneur’s GPS, knowing someone with more experience to impart wisdom is one of the best ways to stay ahead and ensure you’re using your time and efforts wisely. A mentor will help shorten your learning curve, avoid mistakes, and maybe most importantly (especially in real estate), tap into a lucrative network. 

I was lucky enough to find someone early in my career that helped me navigate through a very confusing and intimidating career. Real estate is highly competitive, and it’s easy to get eaten up by the big sharks if you aren’t keeping up your guard. My mentor helped me navigate the treacherous waters and ultimately made me a better version of myself in more ways than I can count.

A good mentor is truly one of the greatest life and business hacks.

Finding success in real estate has also allowed me to become a mentor for a number of my own proteges. I am unbelievably passionate about passing on my knowledge to help others build the confidence they need to step into the batter’s box. If you’re interested in finding the right mentor for your real estate business, then check out my one-on-one coaching program right here.

3. Build Awareness

Let’s return to my earlier point about having clarity and discipline. Both of them are essential, but neither of them is half as effective if you aren’t aware of the game you’re playing. Everyone on the field is playing baseball, but a catcher and a center fielder are playing the game differently. The same goes for business. Real estate takes a particular set of skills and strategy that are vastly different than say venture capitalism. 

So get specific with your skills. Don’t stop with motivation. Be motivated in the right ways to succeed in your field with your unique strengths and perspective.

One thing I love to ask my proteges is, “What does wealth look like to you?”

A lot of them will give an exact dollar amount or yearly salary. Others will think bigger, not just in dollars, but in how they live their life. They talk about lifestyle and creating an impact grander than themselves. Answering this way shows awareness.

I’ve worked with too many people who are led to think small.

Awareness isn’t just about knowing the game and the field. It’s much more about knowing yourself… and understanding your potential. 

Where Do You Want to Be?

Even when you’re on the bottom of the ladder and you don’t know if you have the energy or knowledge to climb to the top, remember this…

My story began with me in a jail cell.

You are only ever limited by your own thoughts. To so many people, a million seems like an impossibility, but every dollar brings you that much closer. And every dollar makes a million more of a reality.

Winning at any business, from retail to real estate, requires us to push our boundaries and limits. But as long as you stay disciplined, seek help from people who’ve been through it before, and believe in your full potential, you’ve won half the battle.

To learn more, listen to my talk with Chris on the StartupCamp Podcast and check out my podcast, The Millionaire Mindcast.

What are some of your tried-and-true rules for success? I’d love to hear in the comments below!


Matt Aitchison
I’m a millennial entrepreneur, 7-figure real estate investor, speaker and avid adventurist. Most importantly, I’m a proud husband and father to two beautiful girls who make life a whole lot richer.


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  1. Florine Dalgety says:

    I am 76 and a retired, and continuing teacher inGuyana. Wealth for me would be the freedom to teach and not ask for a salary. Eighteen years ago a friend and I co-founded a school to give a good foundation to children of low-income families. My experience was secondary science. I am now focusing on literacy and numeracy for little ones.
    I’d like to write and publish. Wish me well. You have inspired me.

  2. Sheri says:

    Loved this article, especially the part about starting at the bottom and the fact that you chose to not be the mistake you made, but used it to push forward.


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