The Original Gangster

The Original Gangster

“THROW THAT FUCKERS SHIT OUT ON THE SIDEWALK! GET 1000 FROM THE LADY ON ELM STREET AND TELL HER IF SHE DOESNT PAY IN 5 DAYS SHE IS BEING EVICTED! GO TO THE ROOF GUYS HOUSE AND TELL HIM TO FIX THAT SHIT TODAY OR HE IS FIRED!” This b.s. is what I was being subjected to back in 2010 as I was minding my own business eating breakfast with some friends. This is how I met my new mentor.

Let me back up a few hours, I had a planned breakfast with some friends of mine at a little cafe in Big Bend, WI. I knew some of the friends well and some not and even a few not at all. Gary was at the end of our big table screaming into the phone to everyones annoyance. Im like what’s up with this goof? I was told he was a big time real estate investor with 170 houses in Milwaukee’s finest ghetto’s.

Gary didn’t fit the bill, he looked like a normal dude. Not rich by any means, very unassuming but obnoxious and loud as hell. Besides thinking he was an asshole I found myself wanting to know whats his deal. When I asked him whats wrong he said just work stuff. He acted like this was just a day at the office. I still remember him telling me it was fun. I decided to pump some intel out of him, if nothing else I could use it against him when I judge his bad manners.

I found out that Gary was on a tear, since the market crash in 2008 he was buying a house a week. He would pay cash, fix, rent and then refinance and at any given time he had about 6 houses in transition at once. He had a crew of 10-12 mexican americans working full time fixing these places. He had been in real estate many years and recognized this as the chance of a lifetime. He was buying up everything, doing it so fast he had no time to set up a legit system to manage everything. He had no office, no office staff, no software for rent management. He didn’t even have a business address except his home.

Pretty much any tenant that had the overpriced rental price tag was approved….automatically. On the first he strapped his 9mm and knocked on every door and left either a receipt for rent paid or a 5 day eviction notice. If your not home to pay on the 1st its a 75.00 late fee and 5 day eviction notice, if you don’t pay in those 5 days your formal eviction is filed and the Sherriff will be contracted to throw your shit on the sidewalk. It was a crude way of doing things and that’s how he rolled.

From the moment I first met Gary in that cafe I was hooked. I wanted to be just like this loud mouth obnoxious gangster. I asked and arranged to ride along with him on his workday and just watch. This is how I learned the good, bad , and the ugly. I was able to look at his strategy and perfect it to something I could swallow and duplicate. I certainly didn’t like every aspect of Gary’s hustle but really appreciated certain things, mainly the rapid growth concept.

The point of all this warped story is that everyone needs a mentor that inspires them. That said, its not important if that person is seen as popular and your mentor need not be perfect. You will still decide what to keep and what to throw but he or she will inspire you to action. Meeting Gary by chance spurred me out of inaction and into the fire. I went on to buy 17 houses in just over a year. Today those same houses are worth almost 1.5 million dollars. Read more about that time here.

I’m glad I met Gary when I did and appreciate what he taught me good and bad. Sometime later I learned that Gary’s empire was being foreclosed on and he was no where around. I learned he moved to FL and restarted there while keeping a crew here to collect rent on every house until the foreclosures were complete. See it takes 2-5 years for a bank to foreclose on a property and during that time the landlord still has control. Not sure how this worked out for him but Im guessing he ended up in Fl with a lot of money.

Unfortunately, sometime later I hear he had passed away with a brain tumor. It’s a sad story, Gary was an original and there will never be another like him. A true O.G.



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