I was 18 when I first started investing in real estate. It shouldn’t come as a surprise that I made mistakes…lot’s of them. I would say I was a real estate failure. I like to think that’s a good thing because these missteps help shape my current investment approach and will ensure we build a solid, long lasting, business. Let’s take a look back at some of my screw ups, if for no other reason than to laugh.

My Story

I purchased my first property in Kirksville, MO as a freshman in college in 2003. My education cost less than my brother’s and my parents decided to equalize things. At first I wanted Mazda RX-8, but then we saw how cheap property is in bumble-f Missouri and changed tracks. Two months later I was a proud home owner.

As a sophomore I moved into the property and rented out rooms to some house mates. I saved all of the profits and worked a summer job to put together more scratch and bought another property. I did this a few more times and by the time I graduated I owned 5 units.

It’s worth noting that I hated being a property manager. I was in college, and I had a lot more interest in how fast I could chug a beer than finding tenants, fixing a broken toilet, or chasing rent. So I searched for someone to help me out, found Carol and gleefully dumped everything in her lap before moving back to Chicago.

My summer job turned into a full time position and I became a high frequency trader at Getco LLC (now KCG). We did well through the 2007/2008 financial meltdown and I wound up with some extra funds. I …read more