Sometimes We Have To Do Things That Suck

I considered myself one of the lucky kids for a long time.

I never questioned what I wanted to do. From a young age, I was always passionate about real estate. But it took me time to get there. I was in the Army and worked in construction. As I got older, I made a goal that I wanted to be a millionaire before I was 30, and I knew that real estate would get me there.

Investing in My Goal

I completely invested in my goal. I expanded my knowledge on construction and understanding what it takes to flip a property, building expenses, zoning, and timelines. This knowledge was so valuable, it pushed me further. I started working in real estate, buying properties, investing in distressed properties. Then, when I turned 28, I made my goal. I became a millionaire.

The kick in all of this is that by the time I had made my goal, I didn’t have anyone to really share it with. The woman I planned on marrying had left me, my family was fed up with my… we’ll say “Millionaire Attitude” and I was alone. In meeting my goal, I lost things that were invaluable. Beyond my relationships crumbling, I didn’t care for my health, and I didn’t make a long-term plan to sustain my wealth.

Going South, and Coming Back

Naturally, things went south from there. I went from being a millionaire to shouldering debt. It was overwhelming. It was a massive lesson in investing in property and in life. I realized then that if I was going to get out of this hole I’d dug myself over years of negligence, I’d have to make a change.

It started internally. I loved real estate, I’d learned so much about the market while becoming a millionaire and new (rather devastating) lessons as I plummeted from grace. I wouldn’t wish it on my worst enemy. It only made sense that years later when I would start my book “Catching Knives,” to focus on what I learned in investing in real estate to help others avoid the havoc I experienced.

Changing My Mindset

Once my mind shifted, I started making better connections with other real estate enthusiasts. I traveled and met entrepreneurs, mentors, and friends that helped me build back what I lost. My own insight in construction allowed me to make better deals with a maturity I didn’t have in my twenties. Now, I find myself so incredibly grateful for all the opportunities in front of me.

It’s interesting how things all go full circle. On the other side of this, I want to tell all of my investors out there to remember to invest in life. As corny as it is, the best success is celebrated with those that have stuck it out with you.

If you want to hear more details of my journey and other motivational content, check out my episode on the podcast Investing For Freedom. We go deep about family, hard work, and purpose.



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Jake Harris is the founder and managing partner of a private equity real estate firm that has managed, developed, and acquired more than $200 million in assets under management in the last five years alone.

This path can lead you to financial freedom, which means you don’t have to quit your job, BUT you can.

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