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John Hupalo Bikes and Invites Education Success

by Team Sammy


John Hupalo is nationally recognized expert in education loan finance and college planning.  He is the co-author of  Plan and Finance Your Family’s College Dreams (Peterson’s, 2016), and regularly speaks on issues related to saving, planning and paying for college at conferences, on television and radio, and in print. 

Prior to founding Invite Education, he worked on Wall Street and served as the Senior Executive Vice President and Chief Financial Officer of First Marblehead Corporation (NYSE:FMD).  

John received his B.A. with Honors from Boston University and an MBA in Finance from New York University’s Stern School of Business.

For recreation, John likes to ride his bicycle, now without newspapers weighing me down!

We are now pleased to present John Hupalo's childhood money memories!


Team Sammy: Share with us a little bit about growing up – your family and community.

John Hupalo: I grew up on Long Island in a hard-working middle-class family. My father was a foreman in a can manufacturing plant. My mother stayed at home when my brother, sister and I were young. Eventually she went back to work. One of her last jobs was as an accounts receivable clerk. Although my father attended classes at Brooklyn College, the Korean War and his job precluded him from getting a degree leaving me as the first and only college graduate in our immediate family.


Team Sammy: Share with us one of your first money memories.

Hupalo: My first money memory provides interesting insight into how I currently lead my money life. I consider money to be a scarce resource, don’t like to spend it and am willing to sacrifice to save it. I remember being pretty young. My mother gave me money to go to the corner store and said I could buy candy with the change. I have this recollection being conflicted: should I spend all of the change on candy? Should I bring some change home? When I returned with candy and some change, my mother praised me for shorting the candy purchase to bring back some change, but also told me to spend it all next time!

Another early money memory came from my mother: she insisted that bills always be turned in the same direction. I find I still do that today.


Team Sammy: What was your first job?

Hupalo: My first job was a paper route which I loved because I got to ride my bike around town with a basket stuffed with newspapers. I learned a lot about the importance of sales and interpersonal skills. Back then, the paperboys were responsible for collecting so we had to knock on doors to get our subscribers to pay for their papers. Some customers were very nice and added a tip. Others seemingly forgot that they actually subscribed, would pay late and not even consider a tip. But we had to be polite and were required to thank them for being a customer. To this day, I go out of my way to thank our customers who give us the opportunity to do the work we do.  One element of the paperboy job that I loved was the responsibility of adding subscribers. I derived great joy in chasing the ultimate thrill of victory: enrolling a new “Daily and Sunday.” Stringing together new “Daily and Sunday” subscriptions gave a paperboy swagger around town, and often bonuses and prizes from the many contests the papers used to entice us to grow our routes.


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

Hupalo: That leads me to my one money habit tip: treasure, but enjoy, the money you earn.  Just before the stock market crash in 1987, I received an MBA in Finance and landed a job in investment banking. I saw in practice first-hand what I knew intuitively in the corner store many years before: you have to balance consumption and saving.  My investment banking colleagues, particularly the senior leaders, were well compensated. Too many of them, however, lived beyond their means on the foolish hope that the scarce resource, money, would forever be abundant for them. When the market crashed, some were suddenly unemployed with an unsustainable expense base and little savings. The lesson for me was clear: work hard, enjoy the fruit of the labor, but be sure to save as much as possible for a rainy day. There will be rainy days.


Team Sammy: Is there anything else you would like to share with the Sammy Rabbit community?

Hupalo: I’ll offer three pieces of money advice that we talk a lot about at

First, our trademarked phrase: “Saving a dollar today is better than borrowing one tomorrow.” Although we use it to emphasize saving any amount, even small amounts, for college as a way to reduce student debt, it is a fundamental core money best practice. Earning interest on an asset beats paying interest on a debt.

Second, student loans should be the last resort, not the first option to pay for college. Families are consumers of education and are in a position to select a college that fits their needs. Affordability needs to be an important criterion when selecting a college. Borrowing as little as possible increases a student’s return on their investment and positions them for success in the future.

Third, know before you owe. MyCollegeCorner talks about this in the context of planning and paying for college, but its application is broader.  Consumers do not have to be victims in financial transactions. By doing the homework and better understanding the details, consumers ultimately have more control over financial outcomes than they might think. No doubt some folks are victims of sophisticated frauds and scams. But is also true that too many people get into money trouble because they don’t properly plan for money success. When they look back, it’s easy to see why things went astray.  My least favorite phrase: “I wish …”

Thanks for your excellent work in financial literacy for kids.


To discover more about John Hupalo and Invite Education, visit:

Sammy Rabbit loves championing and raising awareness on the importance of early age, youth and family financial literacy education.

One of his favorite methods to raise awareness is to share the stories of people and enterprises who want to make a difference in the lives of others, like John Hupalo, Founder and CEO of Invite Education!

IF you would like to join John Hupalo and be featured in Sammy Rabbit ’s Childhood Money Memories Interview, a Sammy Spotlight, be a Sammy Guest Blogger or highlighted in one of Sammy’s Quotes and Questions of the Week, contact us.

Read more childhood money memory stories: CLICK HERE! Have a Sammyriffic day!

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