191 | Teaching Kids About Money & Entrepreneurship with Rob Phelan


Welcome to episode 191 of Profit Boss® Radio! In this episode, we’re talking about how to teach your kids about the value of money and entrepreneurship. 

Schools rarely teach financial responsibility, encourage entrepreneurship, or equip kids with the skills they need to understand our money systems. It’s why so many of us learned these lessons the hard way–and it’s why it’s so important to make sure our own children get a better financial education than we did.

With that in mind, I’m thrilled to be talking to Rob Phelan. Rob’s a high school math and personal finance teacher by day, but by night, he’s the author of M is for Money, a book of financial lessons for kids, as well as the founder of Simple Startup, where he provides online coaching for 10-18 year old entrepreneurs. 

In today’s episode, we’re talking about how to teach your kids about money and finance in ways that they’ll care about. We’ll also hear about some incredible companies founded by amazing kids, and help find ways to make sure that children have a better understanding about the value of money that you wish you had when you were young.


Here’s what you’ll find out in this week’s episode of Profit Boss® Radio

  • The hard financial lessons that helped Rob learn about money in his 20s.
  • Why kids don’t need good math skills anymore to have great money skills. 
  • The value of teaching kids financial independence over financial literacy.
  • The importance of leaving a legacy for our children, and the value in teaching our children at an early age.
  • The wonderful success story from a young girl who took Rob’s course and is still demonstrating a tremendous amount of entrepreneurial spirit.
  • Why you don’t need to be all knowing–and how to encourage your kids to develop their own healthy relationship with money.

Resources and Related Profit Boss® Content


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Hilary Hendershott: All right. With me here today is Rob Phelan. He’s a high school math and personal finance teacher by day, an author, referee, curriculum writer, teacher, resource creator, and business guide for kids by night. He’s the founder of Simple Startup, which is an online coaching company for 10 to 18-year-olds and 10 to 18-year-old entrepreneurs. And then if you wanted him to cover more of the young people market, he now has a children’s book coming out called M for Money, which I have preordered and you should go order today, which will be published November 13, 2021. Do I get the date right? Is it November 13, Rob? 

Rob Phelan: Yup, this coming November.


Hilary Hendershott: Awesome. That is awesome. Welcome to the show. 

Rob Phelan: Thank you so much for having me, Hilary. I’m really excited to be here. 

Hilary Hendershott: Yeah. So, we’re here today to talk about M is for Money, a book of financial lessons for kids as young as three, which is being published again this week. And I listened to the audible version today. It’s really awesome. But, first, I just want to talk to you about kind of how you got to where you are. You say you started with zero money knowledge that your wife was actually running the money between the two of you. And what happened? 

Rob Phelan: Yeah. So, I look back on my upbringing and there wasn’t a ton of formal money lessons in there. I grew up in New York for the first 10 years of my life, and then my parents moved back to Ireland because they were originally from there. So, I spent the next part of my formative years in Ireland, and then when I moved back here in my early 20s, I just had no clue about money and how it worked, especially the financial system here. So, yeah, I’m very naive and when I met my wife, thank goodness her dad had given her some great money lessons and she was the financial person in our relationship, starting off, and eventually communicated to me like, “I don’t like the pressure of being the person solely responsible for the finances of our relationship in our household.” And she asked me like, “Will you go learn about this stuff so we can make decisions together?” And that was a big moment for me to start like there was a kick up the butt to really go learn this stuff and kind of start coasting on her coattails, which definitely had been doing up until that point. I was focusing on other areas like the start of my teaching career. Yeah. It was a great incentive to go and actually learn. And since then, I realized how passionate I am about personal finance and helping other people to learn about money as well. 

Hilary Hendershott: So, you’re a math teacher, so that goes nicely with learning about money. What was the best resource that you used to learn about money? How did you go about doing that? 

Rob Phelan: So, totally self-taught. Math is great, I guess, because it’s a numbers game but it’s not a huge amount of like math knowledge that would transfer over. Like, I teach a personal finance class to seniors and it’s technically a math class, and I’ll get kids coming in there every year and like, “I hate math. I sucked at math. My parents were awful at it,” and they have all of these negative associations with math and then they think, “Okay. I’m going to be bad with money as well because of that.” And what we realized very early on is actually, you know what, it is very little math skills that are required to be good with money. There is so much help out there now in terms of calculators. There’s different guides that you can find. And frankly, we make most of the stuff we do automatic anyway. So, it’s not like you have to be on a day-to-day basis like balancing checkbooks and transferring money in different places or calculating your compound interest. It’s all done for you. So, it’s more of a mindset kind of game rather than a numbers game. 

Hilary Hendershott: Yeah. Okay. So, you’re self-taught, meaning you read books and blogs, just kind of everything you could get your hands on. And now you’ve published two books for kids raising adolescents and kids about money. Why did The Simple Startup come first? 

Rob Phelan: So, what I think about personal finance, entrepreneurship is actually a big part of personal finance for me because I think the equation for personal finance has got to be earn more, spend less, and then invest the difference better. And earning more we think about, “Okay. How do I get a raise at my job?” And that’s great but there’s always a ceiling to what you can do in a job. And if you start thinking about multiple streams of income or other ways that you can earn money or even working for yourself, you raise that ceiling much higher, and that’s something that was really exciting for me. There’s no limit to how much money you can make but there is a limit to how much you can cut out of your life. So, for my students, I wanted to teach about entrepreneurship and we do many company projects. So, for five weeks, we will start a business, they’ll run it, they’ll make profit from it, hopefully, and we’ll shut it down after about five or six weeks, and a lot of them will continue doing it in the background because they just like doing it. They like making extra money. And that was the genesis of The Simple Startup. I was creating these worksheets to kind of act as prompts for the kids so that they would think about their idea generation. They’re kind of getting everything down on paper. So, I don’t really buy into business plans but I love business snapshots, so just a quick briefing of what your business is going to look like and then start building. 

I realize at the end, I’ve got kind of the makings of a big resource here. It’s too big for something like teachers pay teachers. So, I was like, “This is a book,” and ChooseFI who I work part-time for in their foundation, they have a publishing brand and they’re like, “Yeah, absolutely. We’ll pick this up. We’ll put this out there,” so they published The Simple Startup and, yeah, that was the start of it. 

Hilary Hendershott: Great. So, what are some of your proudest win stories coming out of The Simple Startup? I mean, what are some of the businesses kids ran with that are exciting? 

Rob Phelan: So, it’s not like anyone is starting the next Apple or Microsoft right now but like even just last two weeks ago, my wife got an email from this little girl. She’s nine years old. She was eight when she did the course and she’s like, “Hi, Mrs. Phelan, I just want to let you know that the Halloween greeting cards are out this year. I had a great time making them. Would you be interested in buying one?” And I was just like so proud of her like she went back to her existing customers, told them like, “Hey, there’s…” and asked for a sale. And I was just like that to me, is such a proud like a little nine-year-old is out there with her greeting card business, and she’s killing it because she’s still doing it. She’s getting more and more sales every year and she’s chasing customers rather than just kind of waiting for them to pop up. 

Hilary Hendershott: That is awesome. That’s more than most entrepreneurs do, actually. You should tell her that. 

Rob Phelan: Oh, of course. It’s so hard to go and ask for the sale. That’s one of the hardest parts, and this kid is just like very willing to reach out like once or twice a year and say, “Hey, I got new greeting cards. You ready to buy again?” 

Hilary Hendershott: That’s awesome. And greeting cards is a big business. So, you mentioned ChooseFI. Your headshot has you wearing a t-shirt that says ChooseFI, maybe in the episode image, so people might be wondering. Tell us about ChooseFI. What is that? What do you do there? 

Rob Phelan: Okay. So, ChooseFI itself, the company is a podcast that was started by two guys in Richmond, Brad and Jonathan, and they wanted to basically generate information for people about financial independence. Is that a term that’s very familiar with your listeners? 

Hilary Hendershott: Totally. We talk about that all the time. Yeah. 

Rob Phelan: Awesome. Perfect. So, yeah, financial independence and they wanted to crowdsource all of their information. So, they find expert guests, they bring them in, they don’t assume that they have any expertise at all, except that they can ask good questions, and they let the public basically share their knowledge and expertise. And it was one of my first introductions to financial independence. I was really excited by that idea. So, I followed the podcast for a couple of years, and eventually, I reached out and said, “Look, I’m going to make this curriculum for my students that’s based more on financial independence than just financial literacy. Are you interested in teaming up?” And they said yes, which was awesome. So, I came on board part-time as a curriculum writer for ChooseFI and I’ve been there ever since, helping to spread financial education to teachers and communities, and then just sort of provide high-quality content wherever possible. 

Hilary Hendershott: Yeah. That’s awesome. And I really love this idea. I mean, it’s not an original idea but it’s original to talk about in many rooms the idea of raising the ceiling versus just spending less and living in scarcity. So, is ChooseFI closely associated with the Financial Independence Retire Early movement or do they just teach some of the same things? 

Rob Phelan: A lot of the same things that the FIRE movement, Financial Independence Retire Early, is kind of The Movement and then ChooseFI said, “You know what? We’re really interested in this financial independence idea where you’re no longer dependent on your job.” Like, you don’t have to go do it every day. You have enough in your investments that you could stop if you wanted to. But you don’t have to, and a lot of people won’t. They’ll get to that point where they’re like, “I don’t feel like doing this anymore but now I’m really excited by something else, and the great part is the money doesn’t matter.” And quite often you’ll end up actually making money chasing your passions but you can never bank on it at the time so it’s just this really exciting thing that generates choices and opportunities. And that’s what they really focus on. It’s not about hitting that point where you can hit retire and just stop doing everything. They want to help people reach this financial independence point. 

Hilary Hendershott: And have choices. Right. I get it. Okay. So, where did you get the idea for M is for Money? Let’s talk about the kid’s book because I don’t know of any other kid’s books that really teach them good financial lessons. How did you get the idea? 

Rob Phelan: I had a kid. 

Hilary Hendershott: It started mattering? 

Rob Phelan: We love transition points as humans, like any time there’s a transition point, we’re ready for new ideas, new experiences, new things, and having a kid is one of the biggest transition points, I think, in anyone’s life. It’s up there with weddings, moving, meeting that first partner, getting that first job. It’s one of those big points. And for me, it was like, “Oh, I want to be able to teach him to be good with money and be a responsible money manager, particularly when he is going to be in a very privileged position of probably never having to worry about money,” because one of the goals of financial independence is that you’re going to create a money-making machine that actually should continue to grow after you’ve passed on and you should be able to leave to the next generation. So, I’m hoping to be able to leave him like a legacy of you never really got to worry about money but I still want you to learn how to handle it and manage it and diving into, well, how do you actually do that? There were some resources out there. There are some great guides for parents but there wasn’t a ton of resources actually aimed at kids. And the research shows that by age three, most kids can understand basic money concepts. So, I was like, “Okay. I want to create something that targets that age group.” My son is two now. He’ll be three next summer, and I wanted something that was kind of ready for him when he was going to hit that age and we could start talking about just money words and what are we doing when we go to work? What does it mean to buy something? How do you save? All that stuff that we should have learned as kids that a lot of us didn’t. 

Hilary Hendershott: I know and it’s obviously doing what I do. I try to talk to my daughter about money, I would say probably more than most, but I notice how many times I put down that credit card and spend money without her ever even realizing what I’m doing because it’s all invisible to her. And so, if I’m not articulating it, if I’m not saying, “Look at the dollar amount on this restaurant bill. Look how much I tipped. That’s my money. I’m changing my money for this meal for you,” she has no idea. So, these things can just go on in the background without them ever being described or internalized by kids. So, the book itself, would you describe it as a glossary of terms? 

Rob Phelan: So, it’s an ABCs book. And parents, you’ve seen ABCs books I’m sure. If you’re not a parent, you’ll find them somewhere eventually. But each page has like A is for and then the word’s allowance. It has a very kind of layman’s term definition of what an allowance is. And then there’s a mini-story that goes with an illustration that shows an allowance in action. So, the book is going to grow with your kids. At three years old, they’re just recognizing the letter A and they’re happy to have someone reading the story. As they get older, the definition starts becoming more important. You start looking for other things in the illustration that would describe maybe how money’s being used or positive relationships with money. And there’s also a central character, Stash the Squirrel, who pops up in every page and asks the kids a question. So, the adult reader would pose this question to the kids. Like, if you got an allowance, what would you do with it? And you know, as kids get older, those answers should become more and more developed, and you just get them to think about these things because maybe they never get challenged in that way otherwise. 

Hilary Hendershott: Yeah. I gave my daughter a five-dollar bill from the Tooth Fairy for her first tooth and the thing just sits on her dresser. She has no idea what to do with it. She’s just like, “That’s my five.” Okay. So, next year when she’s 6, maybe I’ll teach her how to spend the five-dollar bill. And then are you actually one of the voices in the audible version? Because I listened to that today. It’s great. 

Rob Phelan: No. I was really fortunate. There was a guy named Dale Roberts, who is a podcaster and helps other authors produce their books and audiobooks, and he took me on as a project to show his audience like here’s how you turn a book into an audiobook. So, we did this whole series, and it’s actually going to be published very soon, probably by the time this podcast comes out and I’ll share with you for show notes or anything like that. And it walks any author through here’s how you turn it into an audiobook. And we went on to Fiverr, we found some voice-over people, and we let three of them take a shot at the book. We picked our favorite. So, the person narrating the book is Brad, and he actually does both voices. He does the narrator and the squirrel. He’s like a kid’s voice artist. 

Hilary Hendershott: Yeah. Because I was sure it was two people. Well, that’s really great. And if you’re listening, you can download the audible version. It’s a fairly low cost. I think it was just $3 today. Okay. So, what are you most excited about this book? What do you think are the prospects or what the thing that’s most exciting for you about publishing this book? 

Rob Phelan: I guess what I’m really excited about is as people have started getting it, so I did a Kickstarter, and for anyone who’s not aware about Kickstarter, it’s a crowdfunding platform where you can go in with an idea and you can tell people about this idea and then they can come in and back it so they can, basically, you pre-sell the product or the service, whatever it is. They commit money. They pledge money to it. If you reach your goal, everyone’s credit cards get charged and you now have a pot of money to bring your idea to life. So, for M is for Money, I wanted to make sure that people actually wanted this book before I went to the trouble of trying to print it and be that person stuck with 2,000 copies of a book that will never move. And what I was really excited about was that there was high demand very quickly, so I reached my funding goal in the first seven days and then by the end of the campaign, I had more than doubled my goal. So, I was like, “Okay. People want this.” And I got my backers their books into the last couple of weeks, and I’m starting to get that feedback from them now like, “Oh, my kid really loves this.” 

My kid pointed to a sign in the store today, and it’s like, “Oh, that’s what it costs,” and I was like, “Yes.” That’s what we want. We want just like these little, almost insignificant stories that like your kid is starting to recognize money stuff in their life around them. And just by doing that, they’re going to start thinking about it and having conversations about it. And parents or guardians or teachers are just well-placed now to like foster just kind of like get that fire to burn a little bit more or just tend to it. You don’t have to do anything special. You don’t have to be a teacher. You don’t have to be like this all-knower of money things, that you just have to kind of encourage kids to think about it, play it out, and they will, on their own, develop a great, healthy relationship with money. 

Hilary Hendershott: I preordered 10 copies. I’m going to give them out to all the kids’ birthday parties I get invited to. I’m going to be that lady. 

Rob Phelan: I love it. 

Hilary Hendershott: At least what you see is what you get. It’s like, of course, I would give you this book. And I actually did want to ask you about your Kickstarter. Do you have any tips for people that do a successful Kickstarter besides obviously have a great idea that people are voracious for? Anything you think led to your success there? 

Rob Phelan: Unfortunately, the idea is not even the most important thing, and we hear that with businesses all the time. It’s less about the idea and more about the approach you take, and it does come down to a lot of marketing. So, first thing I did was I reached out to someone who had already run a successful Kickstarter and that was Tiffany Aliche. And so, she has a wonderful kid’s book as well called Mali More. And so, I looked for someone who is doing something similar to what I wanted to do, and I reached out and I was like, “Hey, love what you did with your book. I saw you do Kickstarter. Can you give any tips for me?” And she was like, “I read this book. I did these marketing techniques, and then I press play and let it go.” So, the book was called Kickstarter Launch Formula, and it was a very simple, low-cost book on Amazon. And it just walked me through the steps of, “Okay. You want to think about the story that you’re telling people. It’s very much about the story.” So, how your idea came about, how it’s going to solve a problem for people, why they need it, all the things that we should be thinking about as business owners or even like if you’re applying for a job like why does the employer need you, all these kinds of marketing skills that I know you’ve been developing on this podcast for a while.

Hilary Hendershott: Yeah. Marketing is its own animal. Well, I hope that you’re teaching the kids in your startup course about how to run a successful Kickstarter. They would probably be great video participants for you. Okay. So, let’s see. Everyone who’s listening, definitely run out today and grab a copy of M is for Money. Get them for all the kids. They fit in stockings maybe, use them as stocking stuffers, but we’ve got to start teaching our kids about money. Rob, is there anything I didn’t ask about today? 

Rob Phelan: No. If you’re interested in your young child at home of 10 to 18-year-old becoming an entrepreneur, so maybe they’re showing some signs of wanting to earn more money, and they’re maybe not old enough yet to get a part-time job or a lot of us are just not cut out for part-time jobs. We don’t like the rigidity of the schedule. We don’t like having a boss or working for minimum wage. If you’re seeing a kid who is showing those sorts of tendencies, I run a course called The Simple Startup, and I just guide young entrepreneurs through the steps in coming up with an idea and then turning it into a business as fast as possible and for as low cost as possible. So, just like I did with my book, that was me doing an exercise, and here’s how you produce a book for free. So, I didn’t put any of my own money into it. It’s all done through Kickstarter, so I pre-sold everything and then was able to use that money to bring the idea to life. And that’s something I’m consciously trying to talk to my kids about is don’t put your own money into it for very limited amount and then grow that idea based on what your customers want. 

Hilary Hendershott: Great idea. 

Rob Phelan: You can find more information about that at TheSimpleStartup.com

Hilary Hendershott: We’ll link to that in the show notes for today’s episode, Profit Boss Radio Episode 191. I hope you’re still offering this entrepreneurship course in five years. My daughter will be 10 and I’m putting her in it. 

Rob Phelan: I hope so. 

Hilary Hendershott: So, thanks for joining us today. All right. 

Rob Phelan: Thank you so much, Hilary. I really appreciate being on with you and your audience.



Hendershott Wealth Management, LLC and Profit Boss® Radio do not make specific investment recommendations on Profit Boss® Radio or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.


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