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Rob Phelan, Author, Teacher, Financial Educator

by Team Sammy


Back Story

We are pleased to introduce you to Rob Phelan, Author, Teacher, Financial Educator and Founder of the The Simple Startup!

Rob is a personal finance and math teacher in Maryland. He is a curriculum writer for ChooseFI Foundation, and author of soon-to-be-published M is for Money.

Phelan is also a Certified Financial Education Instructor by NFEC and a very active financial education advocate in the education community. 

Rob shares that his full-time role is being husband to his amazing wife, Amanda, and dad to his almost-two year-old son!

For fun, Rob is a soccer player and a big soccer fan. He loves to catch games whenever he can, and says one of the things that brings him the most joy in this world is going outside his my son to kick a ball around. 

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Team Sammy: Tell us about what it was like growing up – your family and community?

Rob Phelan: I have a slightly unique perspective on money and how I was raised. I was born on Long Island, NY after my parents immigrated to the US from Ireland in their mid-twenties. They left Ireland seeking a higher chance of employment and a new adventure, since Ireland was having difficult financial times in the late 80's.

We stayed there until I was 10 years old, and then we moved back to the Emerald Isle where I completed elementary school and then secondary school. It was during this time in secondary school that I had one of the most impactful experiences of my education career, and life overall. Ireland has this very interesting school system setup, where when a student completes 3rd year (the equivalent of 9th grade), you are then offered the option of a "Transition Year". This is an option year which you can choose to take part in, or skip to accelerate your timeline to graduation. Transition year is designed to be a year of exploration and development. There are no formal assessments or testing. Every class teacher is encouraged to use the time to explore fun and exciting experiences within their subject, that will help expose students to a variety of experiences and skills that they may not come across in or outside of school.  

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During this year we did things like run a school newspaper and take part in a theatrical production (I played Lieutenant Brannigan in Guys & Dolls if anyone wants to know).

We had some exciting physical education opportunities like surfing, kayaking, orienteering, and hiking.

In math we explored probability through deep dives into the different forms of gambling.

My favorite class was our business class. I hadn't taken a business class before and another part of the Transition Year experience is to try lots of different subjects and areas that you may not have experienced before. In the business class we learned about stocks via a short stock market challenge and we also were tasked with starting our own mini-company. We had to come up with an idea and turn it into a reality! Each company then had a chance to win a school-based competition, and then go represent the school in county and potentially national competitions. 

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My 2 friends and I started a baking company! It was simple, easy to start, and extremely profitable. We walked about from that project with €500 in profit, which at 15 years old was quite a bit of money!

How many classes did you take in high school that allowed you the chance to make some money?

This experience was my first exposure to entrepreneurship and creating my own income in a meaningful way. I had done some other small entrepreneurship experiments in the past like a bottle/can recycling business and a homemade pinata business, but this was the first time I had some guidance and direction to follow for charting out the path of a business.

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Fast forward to age 26. I'm married, working full-time as a teacher, and about to move into our first home. My wife was the money person in our house. I had that business experience in secondary school, but I didn't really have any formal education about personal finance and managing money. I had pushed that entrepreneurship bug to the back burner and instead focused on my teacher training, and getting that first big kid job like everyone is "supposed to do".

Once I had that job and money was coming in, we were comfortable. Not struggling with money, but also not putting anything aside for savings or retirement. We made it to the end of the month with $0 in our account, and next month we spent it all again. It wasn't desperate. It was comfortable. 

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My wife wasn't comfortable with the role of being the money person in our house. It was a lot of responsibility and she wanted a partner in this process as opposed to someone to follow her direction. She asked me to take on more of a role in managing our finances.

At the same time my school asked me if I was interested in teaching a math class that incorporated personal finance too. I didn't know anything about it, but I took it as the opportunity to learn and grow!

That summer I dove head-first into personal finance, starting with Dave Ramsey and graduating into podcasts like ChooseFI, Afford Anything, Stacking Benjamins, Planet Money, Marriage Kids & Money, Earn & Invest, Motley Fool Money, and Bigger Pockets Money.

I loved this new idea of "financial independence" and the type of life it could bring. I was 100% in, and my wife was excited to chase it down too.


We started aggressively paying down debt, putting money aside in our investment accounts, and increasing our income.

The last part is what really got me excited. I go back to that high school experience and how someone can create money for themselves!

When it comes to personal finance, you need to trim your expenses, increase your income, and then invest the gap you create in your finances.

For expenses, you can only trim so much. For earning however, there is really no limit to what you can make! I started exploring different side hustles and ways of creating more income for our family.


This led me to refereeing youth lacrosse over the summers, writing my first book, becoming a freelance curriculum writer, and then offering my Simple StartUp Challenge course so I could help other young entrepreneurs experience the same wonder I did at 15 years old.

Most recently, I realized there was a shortage of quality resources for parents to use to teach their kids about money. This led me to dedicate a 3-month experiment to writing a children's book and self-publishing it.

The book is currently with the illustrator and should be released this summer! It's called M is for Money and you can find out more about it at

I've developed a huge passion for helping people, particularly kids, to learn how to do better with their money and get on a path to financial independence. With the way our system works, figuring out how to invest and manage what you have from a young age, supercharges your path to financial independence and really it takes a lot less to make it happen. 

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Team Sammy: One question I ask everyone is: If you could only teach a child one money habit, what would it be and why?

Rob Phelan: If I could magically get all students to adopt one money habit, it would be to set up systems for themselves to automate their finances. Have a percentage of each paycheck go into investments and just manage the rest. They would all be set for life if they could do that one simple thing. 


Team Sammy: Should personal finance be taught in schools?

Rob Phelan: I am a huge advocate of personal finance education in school. At ChooseFI Foundation, we have developed a PreK-12 Personal Finance Curriculum that is FREE for any teacher or parent to use with kids.

M is for Money is targeted at 3-8 year old kids based on research that shows that by 3 years old, kids are able to understand basic money concepts and can begin learning the habits of responsible money managers such as patience, delayed gratification, sharing, savings, giving, etc. 

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Team Sammy: Is there anything else you'd like to share.

Rob Phelan: Thank you for the opportunity to share and for anyone who has taken the time to read this.

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