Wins and Losses Series: Millionaire Mob – “In the span of 30 seconds, I lost over $500”

Wins and Losses Series: Millionaire Mob - "In the span of 30 seconds, I lost over $500"

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Hi, Team!


Welcome to another edition of MikedUp Blog’s Wins and Losses Series, where we interview a generous participant about 4 of the best and worst moments of their life. The point? To learn from the past so that we can improve in the future!


If you’re interested in participating in the Wins and Losses Series, please send me a note here (you don’t have to be a blogger to participate!)



Check out the complete Wins and Losses Series Here


(Photo courtesy of Justin Montemarano)


This week we have: Millionaire Mob!


Millionaire Mob is an early retirement blog focused on everything online income including: Travel Rewards, Passive Income, Dividend Growth Investing, and Personal Finance advice. I hope to provide the best advice to help you learn and grow along the way. Join the mob of financial freedom experts and escalate your life. Follow us on Twitter or Instagram!


Win #1: Making My Own Career from Nothing


I came from a modest, middle-class family. I was taught to study hard and stay focused and I followed my plan and got great grades. My hometown is a midwestern city with values that you should always be working. School or not, I found myself working since I was 14 years old where my parents would say ‘It’s important to understand the value of a dollar.’ Working throughout high school, I found myself going to a good university through continually working hard and sticking with the script… I can work in finance someday.


I got to the point of my senior year of college with a good work ethic and decent grades. I was so excited to apply and land some great interviews with Boeing, Lockheed Martin, and several large national banks.


So what happened?


I was denied at every single one. So, this is great? Racked up over $60,000 of student loan debt and worked my tail off during school. Nothing to show for it.


This motivated me to another level. I took it upon myself to outreach to finance firms that I wanted to work for. This included all the biggest investment banks and others in the Midwest. I was determined to land that dream job.


Through my relationship building and connections, I was able to land an awesome finance job in Chicago. This helped me build the base of my career and I’ve been building off it ever since.


By finding that initial job, I was able to eliminate those student loans and buy a home. Now, I’m onto house #2 and looking into rental properties.


Win #2: Dividend Investing Your Way to Financial Freedom


Over the past few months, I wrote a book called Dividend Investing Your Way to Financial Freedom. This was a great experience for me. It took significant work. More than I ever imagined, but it was so well worth it. Once you launch your book, the work just begins. You need to find people that actually want to read it!


Through writing the book, I was able to learn so much more about investing and myself that I wouldn’t trade it for anything. Through the writing of my dividend investing book, I wanted to provide people with the tools that would position them for success. In addition, I developed a five-step formula for what it will take to achieve financial freedom through dividend investing. You can use my dividend investing calculator to see what it would take for you to achieve financial freedom. It takes only five minutes to input the assumptions.


I call this a great win because through writing this book I was able to develop a plan for me to achieve early retirement. I have a long way to go, but you know what the famous saying is:


“A goal without a plan is just a wish.”


I plan to use this as a foundation for me to continue to push the envelope on my financial success. I encourage everyone to develop some sort of long-term plan that will ‘unlock’ new financial goals. When I say a plan, I’m not talking about a New Year’s resolution. Your plan should be a roadmap for success. Print it out and put it somewhere you can see every single day.


Remind yourself of your successes and failures to continue to push yourself for improvement.


Loss #1: Trading My Way to Instant Losses


When I was fresh out of college, I got my big gig in finance. I thought I was going to be the next Gordon Gecko. I was very wrong about that. After I graduated and started making good money, I thought I could trade Apple stock daily via options. I spent a couple of days outside of work and even at work trading Apple options. Things were going okay. I was learning and improving.


One day I was trading options on Apple and the stock started reversing quickly. I owned call options. If you are speculating, you basically want sharp upwards movements in the stock price. That didn’t happen. It went the other way due to supply issues. In the span of 30 seconds, I lost over $500. I was freshly out of college so that was a lot of money.


Looking back on it now it really isn’t that big of a deal. It’s important to me because that was the moment I changed my philosophy about finances. I started immediately paying down student loans and bettering my financial future. I’m a better person now because of it. I’m still involved in options, but not in that way. I basically only sell put options on stocks that I like.


Now, I focus on a more simple strategy and I’m more comfortable with my risk tolerance as a result of this failure.


Loss #2: Failed Startup


A few years after college, I thought I could take an additional risk. I had more money in savings and nearly paid off all my student loans.


I developed an online software platform that had some decent success. I grew the software platform to over 3,000 daily users. I had one problem. My revenue model was flawed. I poured a lot of money into that growth. Unfortunately, without outside investors, I couldn’t continue to bootstrap the platform. The funding requirements to keep the platform running were too much for me to cover. I had to shut it down. I literally put 60-80 hours per week to try to make this into a successful venture. After pouring a bunch of money into this, I’m not too concerned about the lost money because I learned a lot and created some great relationships.


I learned a great lesson that I don’t need to chase sexy startup enterprises. I can do something simple and make it into something unique. I needed to dumb it down.


I’m a firm believer that you learn more from your failures than you ever will from your successes. What will you do to improve on your failures?


Reader’s Input


I really enjoyed the point that failures weren’t debilitating – just another opportunity to learn, course correct, and move forward. That was refreshing. What stood out to you about Millionaire Mob’s Wins and Losses? Let us know in the comments below and we’ll keep this discussion going!


Thanks for reading!


If you’re interested in discovering a better version of yourself – whether with fitness, finance, or family – then subscribe below to MikedUp Blog’s FREE newsletter and let’s improve together!


I’m glad you’re here. Thanks again and talk soon!


– Mike
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