Monkey Free Me Philosophy- Where did my thinking come from?

A little rant about what this site is meant to do is always a great way to figure out what this site is meant to do.

I guess I am a rare case because when I was 8 years old I discovered our free enterprise system by accident at a soccer game when I wanted to buy some M&M’s and I knew at the grocery store they were 50 cents and they sold them for 75 cents. I knew I was getting robbed out of a quarter, but I wanted the chocolate and bought it anyways. I went home and thought why are prices different for the same item. My dad explained about scarcity and supply and demand, but in 8 year old terms and I decided that there is no candy at school and I needed to get some there. My mom took me to Sam’s Club and I spend all my money from Christmas ($20) on 2 boxes of candy and did a little math and figured out that for 50 cents a bar I could have $40 at the end. I sold out in 2 days on the bus and at school. So the next week I bought 2 more boxes and continued this for months at school. I was a glorified candy dealer and everyone knew my name. It got so bad that the principal pulled my parents and me in to shut us down because the cafeteria was loosing money and parents complained their child only ate candy at school thanks to me. I was happy to shut it down because I had almost $1,000 in a bank account.

My next lesson was learning about interest from my bank account. I didn’t add anything into it for months and one day I went to the bank with my dad and checked to make sure my money was still there and it was and it gave birth to new money. I was shocked that I had made more money from doing nothing. It was only a few dollars, but I was 9 at the time and it blew my mind that you could make money doing nothing at all. I continued to watch my money grow with interest over the next few years while adding nothing to it. I decided that I wanted to make money doing nothing forever! It turns out you need more money than $1,000 to live forever without working.

With a little money in the bank, I learned investing at about the age of 8 with some baseball cards and comic books. I would trade at school, at comic shops, and at card shows, and it eventually grew into a large collection of Ken Griffey Jr. rookie cards, various rarer Marvel comics, Bo Jackson football and baseball cards, Michael Jordan cards, Operation Desert Storm trading cards and other weird collectables. I learned that if I spent $1.25 on a comic it could be sold at the comic shop for $5.00 in a year or so. I learned that if you spent a little and waited you could get a great return on your investment. I also learned that paying $10 for a baseball card sometimes meant that after a scandal it could be worth $1! I traded comics and cards until about age 12 making a good amount, and I also learned to hold onto some investments for the long haul. I still have about 100 comics and 1000 cards today in my mid 30’s. We will see how the long investing game favored someday.

When I was 14 I decided I wanted a job, but you had to be 15 to work so I found a friend of a friend who was willing to break the rules a little and I got a job at restaurant as a bus boy cleaning tables on the weekends only. I learned about minimum wage and that it sucked ($4.25 at the time), and I learned about tips and the power of service. I was a bus boy, but I knew I would get better tips the more the people spent in the restaurant, so instead of just cleaning table and learning to smoke out back like most of the older bus boys, I walked the restaurant, cleared plates as they finished, refilled water, and made light conversation with the patrons. I noticed an increase in tips and so did the waiters in the areas I covered. I was requested by waiters to work their areas because they got paid more if I worked with them. I would walk out at the end of an evening shift with over $100 in cash and my minimum wage paycheck. If I made over $200 in tips in a night I would reward myself with a piece of cheesecake from the kitchen at the end of the night and most nights the manager just gave it to me for free. I learned about monetary goals, service, and how to market myself by going the extra little bits not in a job description. My bank account grew to $15,000 at this time just in time to make a big financial mistake.

I turned 16 and it was time to buy a car, so I went down to the dealership and saw a nice new Dodge Truck for around $15,000. I thought I have that much and bought it without a test drive. I was broke as soon as I signed the papers, but was proud I owned a new vehicle and drove around as my friends drooled over it. By this time I became a lifeguard because that was were the ladies were. I was getting $14 an hour to sit by a pool and about once a week save a kid who forgot the deep end was deep. I covered my gasoline and insurance, but with bills and a car that I learned later was depreciating rapidly in value I was not making any real money like I use too with no car and no bills. I also bought a TV for my room and a couch too for when the boys came over we could hang out better in my room instead of in the living room. I was dating and spending money on girls. I was working and seemed to always have about $1,000 in the bank that never grew. I learned about the system of work and bills. I also learned if you spend you money on stuff the stuff begins to own you, such as my truck. I couldn’t stop working now because I had bills. I had to change my life, so I sold the TV at a loss, sold the couch at a loss, and began to date girls by going to the lake for free and having a picnic. It turns out that that is more romantic anyways in their eyes. I got my saving back up $5,000 just in time for college.

In college I got a basketball scholarship, learned to negotiate a contract and grew into a man by standing up to out of control coaches, and demanding they treat me with respect. I transferred after my first year, after negotiations broke down and someone happily picked me up where I learned about healthy work environments and how sometimes a few toxic people can ruin everything or an organization. I worked summers so I could live during the season. It turns out that in NCAA basketball you get 3 meals a day, a room to sleep in, tuition and books and not much else because of the rules. So if I need a new jacket or notebook for class I was on my own. If I wanted snacks for the dorm or money for a date I was again on my own. So I worked summers on a river driving a bus 4 days a week for 8-10 a day for $12 an hour plus tips. Again my service experience can to workout and my bus always made the most in tips. They eventually made a rule that we had to split up our tips at the end of the day and all share. It just encouraged me to hide tips or work less hard on my friendly service. It was a terrible policy at rewarded lazy and unskilled people and punished your top performers. I learned a lot about incentives for your employees during this time. I was able to keep my $5,000 in my bank account throughout college and was married at the end of my junior year paid for in cash. I also had no debt and neither did my wife.

We started out our lives together with $8,000 between us; no debt and both had bachelor’s degrees. This is when the monkey climbed on my back. She was pregnant and we had no jobs. Our life plan of both working and traveling was out the window and I had to get a stable life for our family quick. I was planning on going to law school had a good GPA and a good LSAT score. I was excepted at 4 schools, but I couldn’t be in that much debt with a new baby on the way, so I got a job at Lowe’s lumber department, subbed at the local high school, and went to take more classes for a teacher’s certificate. I did all 3 for 9 months to make ends meet on $18,000 a year salary. Our baby was born and we were still debt free, but dead broke living paycheck to paycheck. We went to free clinics for immigrants for our baby’s check ups had a terrible little apartment that the police frequently visited, but as the monkey grew on our backs we had a plan. I got my first teaching job doing middle school, coaching girls sport and working 60 hour weeks for the entire school year for $30,000. I thought like a free agent though and was looking for better work all school year and found a the last minute in July before the next school a job at another school that paid $47,000. We were rich!! So we thought.

We immediately bought a house with nothing down!! Idiots…now we had lots of bills that were bigger than before and we just had a second baby. We were spending way too much and were so broke we could afford a lawn mower, so we borrowed a neighbors for a few months until I could afford a manual one that spun as you pushed it with all your might. We had a half an IKEA sectional couch in the living room because we couldn’t afford furniture to fill the house, and I landscaped it by going into the woods and getting dirt, rocks, and some plants behind our neighborhood. More monkey on my back, but we were normal and all our neighbors talked how they owned nothing and had tons of bills also. That’s when I cracked and began to research a better way to live life. I was determined to get free of the monkey on my back pressuring me.

That’s when my monkey free philosophy began. I hope you read my blogs and learn from them because their ideas and philosophies have been developed over the last 10 years of my struggles and helping others with their finances, lifestyle design, and any other problem that was weighing on us. Thanks for reading and spread the word on social media. I appreciate my readers and do my best to help them.



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  1. Josh,
    I had no Idea that you were into this sort of stuff. I’ve recently been coming into my own with this “monkey free philosophy.” It’s so freeing ridding yourself of debt and realizing that the more we have the more we are enslaved by them. I look forward to reading more. My wife and I love some of the same blogs/podcast you mentioned.


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