‘I Had My ‘Aha!’ Moment Sitting in a Concrete Cell’


This entrepreneur is living proof that our past mistakes don’t have to hinder our future successes.

Matt Aitchison is a hugely successful entrepreneur and the founder of the popular podcast Millionaire Mindcast. He had flipped 100 houses by the age of 25 and earned himself a coveted spot in the top 1000 real estate teams recognised by The Wall Street Journal.

He also has a criminal past.

Raised in Sacramento, Matt was once a troubled youth looking down the barrel of a felony after getting into (yet another) fight at college. While the charges were later dropped, waking up in jail proved to be a pivotal moment in Matt’s life.

“I had the ‘aha’ as I was sitting in that concrete cell reflecting,” Matt recalls. “If I wanted to have an extraordinary life, I was going to have to start doing extra ordinary things every single day moving forward.”

Life had started to veer off course for Matt when his step-mother, to whom he was incredibly close, passed away when he was 16. “I was rocked at the core and my first tragic experience with death led me towards a challenging season of my life,” Matt admits. “I went down a path filled with many poor decisions, including drinking, fighting, and many other extra curricular activities I shouldn’t have been participating in.”

Matt was expelled from high school during his senior year but, despite being given a second chance, found himself falling back into bad habits just a few months into college. “It was almost as if I felt invincible and never fully comprehended what was on the line every time a poor decision was made…” says Matt. “It was my future, my health, my life.”

Thankfully, the prospect of a felony assault and battery charges were enough to make Matt see where his poor choices were leading him. “I was scared of the uncertain future that lay ahead of me,” Matt admits. “I was determined to make a change, and I truly didn’t care what obstacles were in my way because I was never going to allow myself to be in that position every again. I believed I was destined for something bigger than being known as the loser who got expelled from high school, arrested in college, and amounted to nothing.”

Matt didn’t have much of a plan but he did know that he didn’t want a regular 9-5. “I wanted to be an entrepreneur for many reasons,” say Matt. “I grew up seeing both of my parents work their asses off in corporate America, building someone else’s company with little to no appreciation.”

After spotting an ad on Craigslist, Matt began studying to get his real estate license the very next day. “The process was hard, it was a grind, it was challenging,” says Matt, who worked for an entire year for free in order to gain the vital experience he needed to build his own real estate company. “I counted working 51 days straight one time and in that first year I questioned quitting and ‘getting a safe job’ at least 6 times,” he recalls. “Man am I glad I pushed through that.”

Matt’s road to success may not be conventional, but he hopes that by being transparent about his past he is able to inspire others who might have found themselves in a similarly negative spiral. “I have chosen to embrace my past, and all the mistakes I’ve made along the way, instead of being ashamed by it. Why be ashamed?” he asks.

“Life is 10% of what happens to you, and 90% of how you respond to it. When you make a mistake, hit a rough patch, or when life just smacks you in the face, be thankful for the lesson,” Matt advises. “No matter your circumstances, we all have the choice to change. My story is no better or no worse than anyone else’s, it’s just my story. Hopefully something I shared today will speak to the right person at the right time in their life.”


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