This is my story of how I went pretty much totally broke during the great recession. I was at rock bottom and really didn't know how I was going to pay the bills at times. Fast forward 10 years and I've managed to become a total Money Badass. This is why I know that you can turn your situation around. If I could do it, you can do it. Read on to get the uncensored story of how I went from broke to a total money badass.

The Uncensored Story of How I Went From Broke to a Money Badass

The Uncensored Story of How I Went From Broke to a Money Badass

I wasn’t always a Money Badass. In fact, at times I did all the wrong things with my money.

While some may have the natural instinct to be a Monday Badass, most will have to work at a bit and I fell into that camp right from the start.

I definitely had an interest and passion for managing money but I didn’t always take the right steps.


To get this story started let’s roll back to the 80s. Bright colors, electronic music, crazy hair. What a decade... It’s still my favorite decade. I love the music, the movies (Ghostbusters!), and who could forget the NES (Nintendo Entertainment System)?



I was born in 1982 to a middle class family. Dad didn’t pursue college but had that entrepreneurial gene. He was always working for himself or at least trying to start a new business. Some took off better than others.

I can remember he had an above ground swimming pool installation business, which also did pool tables in the off-season. He also had a chimney sweep business and a vending machine business. He was always doing something entrepreneurial.

Mom didn’t go to college either, she took the job route instead. I can remember her working for restaurants, a hotel, and even as a bank teller when I was a kid.

We did OK, but definitely were not rich. Probably a typical income for a middle class family in the 80s. As many parents do, my parents divorced when I was about 2, so I never really experienced living with both of them at the same time. They both moved on to a new husband and wife and life went on.

I was probably the typical 80s kid. I loved my Nintendo, Ghostbusters toys, and BB guns. This was pre internet, so childhood was filled with mystery and adventure.

It wasn’t long before I realized I had the same entrepreneurial gene that my dad had. One Christmas I tore open this big box and inside was this contraption that created toy bugs. It was called a Creepy Crawler set.

Creepy Crawlers

Creepy Crawlers

I was kinda like an Easy Bake Oven but for boys. I loved that thing. To use it I would pour in this colored goo into molds and bake em in the oven. I was creating all kinds of a little colored monsters. The next day I would take them to school and show all my classmates. They liked them too and started asking me to make them some. I gave out some, but decided I wanted to set up a shop to sell my little monster toys. So I did. It was my first little business and first time making some money on my own. :)

I grabbed some poster board and drew up a sign with prices for the monsters, depending on size of course! $.25 for a small one $.50 for a big one. Pick your color too!

Kids were handing over their lunch money left and right! It was fun while it lasted, but my market was limited in a small classroom, so I moved on to the other ventures like candy. Yes, I was that kid selling other kids candy on the bus.

When my mom went to the grocery store, I got the biggest bag of Starbursts I could. It was cost effective to buy a big bag of Starburst and then sell individual Starbursts to kids for $.25 each or a bundle of 6 for $1.00. Sounds crazy? It worked. Kids love candy and bought that stuff up. No parents to tell them no and lots of change burning a hole in their little pockets!

It was entrepreneurial training wheels for the future. I was enjoying the process of making money and having fun making it. All was good until high school…


High school was not a good time for me and money decisions. My focus changed a bit when I got into music. I joined a band as a drummer. (In case you are wondering, we played hard rock like Metallica..)



I really enjoyed playing music and I also really enjoyed recording music as well. The problem with that?

In the late 90s music equipment and recording equipment was expensive! I had various jobs as a teenager like Wendy's, above ground pool installer, and Dairy Queen.

While working at Dairy Queen I would get paid every Wednesday. You know what I did with it as soon as I got it? You probably guessed it! I ran down to the bank, cashed it (yeah, no direct deposit), and then ran to the music store to buy a new piece of music equipment… :(

It makes me shudder just thinking about it now. I was spending money like a maniac… The sad thing was, I knew how to handle money properly but I just wasn’t doing it.

My grandparents had taught me about budgeting, saving, and the value of investing. I was just more focused on music than anything else.

Towards the end of high school I came to a realization while playing music at a party of all places.


We were playing music for a party at this beautiful cabin in the woods overlooking a small river. It was gorgeous. I loved the house.

I asked a friend of mine how this guy could afford all this, and he said he was a stock investor. I was amazed! I knew about stock investing and understood the power from my grandfather, but wasn’t really trying to get involved much at that point.

Cabin in Woods.jpg

"That was a turning point for me."

That was a turning point for me.

I was about to start college and get my adult life started and thankfully I had finally decided to start taking money serious again. I quickly winded down my spending on music gear and started focusing how I could make the best use of my money.

Just a FYI, I didn’t stop enjoying music, playing it, or even recording it. I still did all of that as a hobby, but I damn sure wasn’t dropping an entire paycheck on it anymore!

I created a budget. I minimized my expenses. I even started saving money in Certificate of Deposits. (I would never recommend doing this today.) I was moving on up the list of Money Badass to do list.

Check out this guide to see the steps if you haven't already: The 8 Steps to Become a Total Money Badass

By around 2003 I was loving finances so much that I switched my degree from Graphic Design to Accounting and Finance and was enjoying it.

I got my first “adult” job as an entry level Computer Operator for a credit union at a whopping $10.50 an hour. ;) I bought my first home, a condo, for about $95,000. Life was good! I was around 20 at the time I felt like I was going to be the next Warren Buffet! I had no idea what was coming years later.

Warren Buffet

Warren Buffet

I was getting into it so much, I started reading everything I could about investing. I decided I was going to start getting serious about real estate investing and stock investing.

I opened my first brokerage account at Scottrade and starting buying some stock. My first win was Sirius XM Satellite Radio. At the time it was fairly new and growing fast. I bought $1,000 of that stock just before they signed on Howard Stern. The stock price nearly doubled! I was ecstatic.

Howard Stern

Howard Stern

I pumped money into my Scottrade account as fast as I could to invest and it was growing!

I had opened a 401k when I started working at the credit union as well and it was growing. When I initially opened the account they only would allow us to invest in a small selection of mutual funds which sucked! The ones I had chosen were growing about as fast the stock market in general, but I had to pay the fees to basically just match the market. Ughhh!!!

That all changed when the credit union adopted a new 401k program that allowed employees to invest in the stock market with their 401k! I was thrilled!! I immediately took advantage of it and created my dream team of stocks in my portfolio.

It took off! It was mind-blowing! I had about $40,000 in my 401k and within 1 year I had nearly doubled it to $80,000!

I jumped head first into the world of real estate investing. I believed and still do, that the key to wealth was building a variety of income sources including the core pyramid:

  1. Side Hustles / Businesses

  2. Stock Investing

  3. Real Estate Investing

So, obviously my next venture had to be real estate investing. Lucky for me I worked at a credit union so getting a loan for a real estate investment was super easy! I bought my first property in 2006 for $78,000 with nearly no money down from a bank. It was a 2 family property that needed some work.

Rental Property

Rental Property

I got busy repairing it with the help of lots of family. About $10,000 later it was in good shape and ready to rent. I filled it with tenants and started looking for the next one. By the end of year I had found another property and repeated the same process with success.

I was also dipping my toes into some side hustles. I tried lots of ideas with very little success. I tried creating a video game and selling it to a publisher. I tried creating a record label for local indie bands. I tried starting a tutoring business. I generated some sales but none of them really gained much traction, so I continued to focus on stocks and real estate.

By 2007 I was still in college but about 2 years away from getting my bachelors degree. I had accumulated about $100,000 in stock investments. I had 2 rental properties now worth about $250,000. I bought a new house for $194,000 and loved it! I even bought a Mercedes because everything was going so well… (eye roll, huge mistake...).

Financially everything was awesome and then it hit.


It was around 2007 - 2008 and all my momentum came to a screeching halt.

The stock market and real estate markets began to crash from what we now call, “the Great Recession.” All my momentum pretty much stopped and everything went into reverse.

The job market went to shit, so I was stuck in my career. The stock market was going down daily. The value of my real estate was totally crashing. At the time I felt like my investing career was over.

Gordon Gekko

Gordon Gekko

All of this from greedy douche bag Wall Street guys like Wall Street's "Gordon Gekko," who can never get enough money, no matter how it affects others. I resented them and everything they represented. It changed everything for me. My mindsent was crushed. I felt betrayed by the very investors I had looked up to.

Probably the best thing that came out of all that was a lesson that not everything lasts forever and it totally changed my mindset about money and greed. Without these events I probably wouldn’t be sitting here writing to you today about money.

I’m sad to say It wasn’t a pretty time. I developed a bit of depression and lost my motivation to work on my personal finances because I felt like I could no longer make any progress.

I graduated from college 2009, but couldn’t find a job in the finance industry like I had. Regulations made it much harder to buy rental real estate. My stocks pretty much stopped growing for the next 2 years.

I was doing ok as a IT Specialist, but I felt trapped, and it wasn't where I really wanted to be in my career.

The downward spiral lasted many years for me. I built up debt just to pay day to day expenses. I had $40,000 in student loan debt and no new high paying job to show for it.

It was a struggle just to get by and pay the bills. Life was no longer so good and I just wasn’t as happy anymore. I had a lot of ambition, but I was no longer progressing and it killed my Money Badass mindset.

The Great Recession

The Great Recession

I had hit rock bottom in financial terms. I went from having plenty of money to being pretty much broke.

After years of bad personal finance habits and depression over my financial situation I had finally had enough and began to make a change. I decided it was time to pick myself up and start over again.


By 2014 The job marketing was picking up. The stock market was taking off again. My real estate investments were beginning to recover slowly as well.

I had enough and was ready to turn my life around. Just like my turning point when I was 18 years old. Here I was at 31 starting all over. It was my second and hopefully last turn around.

I immediately changed my mindset about money. I decided to stop worry about what others thought about me and focus on doing what's best for me financially.

One of the best things I did was get my mindset right. I no longer looked at my situation as defeat and realized that economic downturns are only temporary and that I could obtain any goal that I could think of if I focused on the end goals.

I dusted off the old financial spread sheets and got started trying to figure out how to get my financial situation back in order.

I began killing my debt, saving money again, building a budget, and bringing in much more money.

I rebalanced my stock investments and it paid off! My stocks were growing again, and fast! They propelled forward again and shot to a new high for me of $125,000!

Stock Market Bull

Stock Market Bull

I began working on a certification that would help me secure a job with a much higher salary and I did just that. I completed my certification and experience requirements which allowed me to obtain a much higher paying job. After completing the certification my salary shot up to nearly $80,000 a year! My career was back on track.

My real estate was recovering enough that I was eventually able to sell them all by 2017 and focus on other investments, because I had realized that property mangement was not my strong suite.

My investments were back on track and even my personal finances were in order and on track. I was tracking my budget, net worth, accounts, etc, which all led me to this site, Let's Automate Your Money.

Some like to say that everything happens for a reason and tend to believe it. I decided I wanted to share what I have learned. If I could go from rock bottom to where I am today I knew I could help others do the same.

Money Badass

Money Badass

I started Let’s Automate Your Life in 2015 to help people in general, but after a year I decided I wanted to focus down specifically on personal finance. I changed the name to Let’s Automate Your Money and here were are. I’m dishing out the same personal finance advice I’ve been using myself to turn my life around.

It’s been an amazing journey with tons of ups and downs but I feel like I finally made it to a place in my life where I’m happy with my financial position and can share everything I’ve learned with others. Stick with me and I’m going to teach you every step I've learned to become a total Money Badass! This is only the beginning!