Kicking Off a Gap Year with a World Record and an Angel Investor
Augustus Holm, 18, is “all in” when it comes to entrepreneurship.
The California teen, who just graduated high school from The Bishop School in San Diego this spring, has used knowledge he gained from Wharton Global Youth’s Essentials of Entrepreneurship and Essentials of Finance programs to build his nonprofit and technology startup. Both enterprises are hitting their stride. In December 2024, Augustus and his classmates from Youth Philanthropy Council – along with sponsor Jellypop — set a Guinness World Record for the largest amount of shoes donated to marginalized communities. The grand total: 21,604 pairs of shoes, valued at $1.1 million.
Meanwhile, Augustus (pictured above with his Guinness World Record adjudicator) has also been kicking it with his for-profit startup, CheckRx, an app that serves as a plan-comparison tool for Medicare beneficiaries, including seniors and those who serve them, Medicare agents. CheckRx just closed its seed funding round, raising $750,000 total at an $8.88 million valuation.
Be sure to click the arrow above to listen to this podcast episode and feel Augustus’s passion for entrepreneurship, his family business, and his dedication to making it work during a gap year before college.
An edited transcript appears below.
Wharton Global Youth Program: Hello and welcome to Future of the Business World. I’m Diana Drake, managing editor of the Wharton Global Youth Program at the Wharton School, University of Pennsylvania. It has been an excellent year of innovation on our monthly Future of the Business World podcast. I encourage our listeners to discover all our conversations with high school entrepreneurs, which this year started with a discussion about the entrepreneurial mindset, moved through cake pops, tea brands and tennis balls, and today is wrapping up with thousands of shoes.
Augustus Holm, welcome to Future of the Business World!
Augustus Holm: Thank you so much for having me. I’m really happy to be here.
Wharton Global Youth: We have lots of entrepreneurial energy to embrace today. So, let’s get started. First, tell us a little bit about yourself. Where you go to school, and your interests?
Augustus: I’m from San Diego, California. I went to the Bishops School, which is also in San Diego, and I just graduated this year in May. I’m currently taking a gap year to be able to focus more on my entrepreneurial endeavors, like my startup and my nonprofit. It’s also giving me a bit more time to be able to continue to grow it and give me a chance to figure out what I love doing when I’m doing this stuff.
Wharton Global Youth: Gap years. I love them. I think it’s a really wise decision for a lot of people.
You’ve got news going on with both of your startups, and we’ll get to all of it. But first, congratulations are in order, you just helped to set a Guinness World Record. Tell us more about Youth Philanthropy Council and your record-setting event.
Augustus: The record-setting event is called St. Nick’s Kicks, and this is the third time we’re hosting it. But before that, a little bit more about the Youth Philanthropy Council, or better known as YPC. It was started back in 2019, when I was 13 and a lot of our other co-founders were also 14, 15, I think the oldest was 16. We’re all a bunch of young kids that wanted to do something cool. We started with San Ysidro Health, a local community health clinic here in San Diego. We had the opportunity to tour one of their exam rooms, and they were raising funds to be able to build them. They needed around $15,000, and even though we were in sixth grade at the time, we wanted to be able to help any way we could. So, we decided to make these really cool, nice-looking yearbooks that my elementary school did not have at the time. And we decided to make them way overpriced and sell them to the parents to be able to raise the funds. And the parents were more than willing to do it, because there were no yearbooks, obviously, and those were charity anyway. That was our first taste of being able to help them out.
The following year, they said, Hey, we’re going to be doing this gala, and we’d love if you guys would come, because you did awesome last year. All they asked us to do was raise awareness. And with that, we took it as a challenge: You know what? I bet we can raise funds again. And that’s when I asked my mom for help. I asked her, What’s the best way to fundraise? And she took it as her own personal challenge to teach us how to fundraise, how to pitch, how to establish a donor network and utilize that to be able to get additional donations. Over the course of eight months, we were able to raise $130,000 for San Ysidro Health. And then at the gala itself, raised another $100,000 to come to $230,000 total. And at that moment, we wanted to continue doing this. We loved being in philanthropy, so we officially formed the Youth Philanthropy Council. From there, it’s only grown.
Wharton Global Youth: How did that lead into the Guinness World Record?
Augustus: I mentioned St. Nick’s Kicks. This is our third time hosting it. And surprise, surprise, the reason that we started the event was also San Ysidro Health. In 2020, they had this event called El Zapatón, where they give away shoes to anybody who registered for the event. They had about 250 pairs of shoes, and the way that they did it was you needed to give a specific size and a specific style that you wanted. There was a lot of registration that went behind it. Again, they asked us, hey, if you’re able to get any shoes, donate them. We took it as another challenge, and we got 5,000 pairs of shoes to give to them. But they said, Oh well, we have this huge registration process. We’re not going to be able to give all those away. So, what do we do with all these excess shoes? By now, we have 5,000 pairs, right? Well, we just decided to host our own [event] and that’s when we officially started St. Nick’s Kicks. It was received really, really well our first year. So, when we held it again the second year, we wanted to beat our own record. So we used the same donor who is a wholesaler for shoes, and he donated 13,000 pairs. Then we had to take a two-year hiatus, mostly due to donor-related issues. But after two years in 2024, we found another sponsor called Jellypop, an evolution design lab based out of LA. We said, hey, we did 13,000 pairs of shoes in 2021. We’d love to be able to host it again, and of course, break our previous record. And then I figured, this is a lot of shoes, so I wondered, What is the Guinness World Record? I searched it up, and it turned out to be 17,526 pairs of shoes. And I was like, Oh, wow, we’re already right there. It’s like 500 pairs of shoes away. I told them, hey, we are so close to breaking the record. Would you give us another 1,000 pairs of shoes just so we really make sure we can break it? And they said, absolutely. They ended up donating another 4,604 pairs of shoes, and that brought our total to 21,604 pairs of shoes, valued at $1.1 million.
Wharton Global Youth: That happened just this month, right?
Augustus: That was this month, correct, and the donations officially were donated on Friday last week.
Wharton Global Youth: That’s amazing! And it was officially a Guinness World Record, correct?
Augustus: Yeah, officially a Guinness World Record.
Wharton Global Youth: Did somebody come out and actually evaluate?
Augustus: We had a Guinness adjudicator, which we reached out to through the Guinness website. The adjudicator provided all these different guidelines we had to follow to be able to break the record. They came out (they have this cool suit that they wear with a blue tie and a whole uniform) and reviewed our whole accounting process and put us to work during those 24 hours. But it was definitely worth it, because at around 3 p.m. on December 7, Saturday, they officially held up their clipboard that had the officially amazing sign. Our whole group surrounded them, and then they said, congratulations, you guys are officially amazing, and you have broken the world record! And then everybody was cheering, and it was an awesome moment after months of work to prepare.
Wharton Global Youth: Congratulations on that honor, but also on just all the good that you did for the community with those shoes.
You started Youth Philanthropy Council, as you said, around age 13, right? Why did you start pursuing entrepreneurship so young?
Augustus: Like I mentioned, it came by chance with San Ysidro Health. We were in elementary school, and it was a school expedition that we did, so it was a bit by chance for us to be able to see the exam room and get a feel for what they do. Once I asked my mom for help in how to fundraise, how to pitch, how to do all these things related to philanthropic work, she took it as her own challenge to help guide us in the right process, Her support is what drove us to start loving entrepreneurship. Also, both of my parents are entrepreneurs, so I’ve grown up in this environment, but it was only when I was around 13 that I was fully introduced to the entire world, and my mom has a huge part to play in that.
Wharton Global Youth: What does she do exactly?
Augustus: My mom also works in the Medicare space, so I’ve also been able to grow up in it, which is nice. Actually, my whole family does: a lot of my aunts, my grandma, they’re all Medicare agents, which help seniors find which health plans best fit their needs.
Wharton Global Youth: And you do keep saying us. Is this you and your friends or your siblings?
Augustus: The Youth Philanthropy Council is made up of a bunch of my friends. I’m an only child, so no siblings, unfortunately, but a lot of my closest friends feel like my brothers or sisters, and that’s what made up YPC. We have seven co-founders, and then myself as the founder, and that was the group that started with that San Ysidro Health exam room.
Wharton Global Youth: We’ve mentioned Medicare now and talking about your mom. So, I want to switch gears and talk about your other startup, which I find fascinating. It was around the same time, age 12 or 13, that you were helping your grandmother with her work as a Medicare agent. And this ultimately inspired your other startup, CheckRx. How were you helping your grandmother and what did you observe at that time? Help us understand what Medicare is and also the job of a Medicare agent, and then we can talk more about your entrepreneurial journey.
Augustus: A broad overview of what Medicare is. It’s basically health insurance for seniors. Once you turn 65, you become eligible for Medicare, or if you’re deaf and blind, doesn’t matter what age you are, you’re eligible. [We all] pay a little bit of our paychecks every time we get paid. You just pay a little bit towards Medicare, and then that’s why you’re able to get this access to really good health benefits once you turn 65.
A Medicare agent’s job is to help a senior find which health plan best fits their needs. The reason for this is because there are maybe hundreds of different companies with thousands of different health-care plans that have tens of thousands of different benefits. A Medicare agent looks at a senior and says, ‘Okay, what do you need help with? What doctors do you visit? What hospitals do you frequent? What prescriptions do you take? And then they say, okay, based off of that information, out of all of these thousands of different plans, these are the ones that will be the cheapest and cover the most of your benefits. A Medicare agent is important to do that as well, because the process gets extremely complicated, and it’s also a government entity, so it’s not the most well thought out when it comes to flow. That’s Medicare as an overview, and what a Medicare agent does.
When I was 13, my grandma, who is also a Medicare agent, asked me for some help in one of these processes. She’s a little bit older, she’s my grandma, so she’s not the most technologically advanced. She had this giant white binder that was 500 pages thick, and it was filled with these things called formularies. A formulary is a list of drugs that health funds cover. And again, that’s cover [meaning] this is the cheapest cost that we’ll give it to you with co-pay or co-insurance. She had this giant binder, and she would flip through it, looking for all these different formularies. She would give me a list of prescriptions that was maybe, on average, eight prescriptions long. And she’d say, ‘Okay, here’s the name of a drug. Let’s take randomly, Ozempic, which didn’t exist back then, but Ozempic, and I want you to tell me the tier level. On a formulary, there are tiers one through six, and normally you’re only going to see two things on it. You’re either going to see co-pay or co-insurance. Co-pay is a fixed dollar amount, maybe $15, and coinsurance will be a percent. She wanted to know the tier level, because that’s what helps her figure out how much it’s going to cost the senior; how much that prescription list will cost them monthly.
She would have me flip through the book, and then eventually I’d find the specific formula that she was asking for. I’d take all the prescription prices and write them down. Then she’d ask me to do that another five times. That way, I could compare all the different prices to find out which plan would work best for her client. Even though it might sound a little complicated, it’s actually a very straightforward process — but very tedious. It takes a really long time if you’re doing it manually.
I helped her out for two years. But over the course of those two years, I kept on trying to find faster ways to do what I was doing manually. Even at 13, it doesn’t take a genius to figure out I could probably use a PDF [and hit] Command F, instead of me literally searching for it. And then from a PDF, I figured, oh, maybe it’ll be easier to use Excel, so that way I could just kind of consolidate the whole process. And from there, I kept on doing that, finding faster and faster variations through the process, until eventually I built the very first, very, very bad, but very first prototype of CheckRx. That one was super specific. The only person that would be able to use it is my grandma, mainly because the information that was outputted was specific to San Diego County, and only for the eight different plans that she needed help reviewing. And again, there are thousands of different plans, so she only needed eight, and that’s all the information that I was able to get for her.
Like I mentioned, my aunts, cousins, a lot of my family, work in Medicare and are also Medicare agents. When they saw what I was able to make for my grandma, they said, hey, make me one too. Why are you only giving it to her? And I was like, oh, it took me a while to figure out how to make it for her. Let me see what I can do. I was able to make two or three more that were specific to [their needs]. Then they told their bosses. They’re like, wow, this is really cool, but are you able to make it on a national scale? That’s when I started getting to work. I reached out to one of my friends who is really into design. He helped me build the first mockup using Figma, which is a nice mockup app building tool. We built the first mockup of what the app would look like. And with that, I was able to raise my first pre-seed round from friends and family, because they already loved the product, so they were more than willing to invest. I also self-funded a little bit, and from there, continued building it out.
Wharton Global Youth: What exactly does CheckRx do?
Augustus: CheckRx is an app that serves as a plan-comparison tool for Medicare beneficiaries, which are seniors and those who serve them, Medicare agents. The mobile app has a super simple three-step process: scan, compare, and store, so agents or seniors are able to scan prescriptions just by taking a picture within the app. It will automatically read the label, be able to pull the name or NDC code, which is National Direct Code, and then it will be put into our formulary search engine, which takes that whole prescription list that they have and outputs a list of plans that cover the most prescriptions at the lowest costs. That’s a huge time saver. Something that used to take me 30 minutes, now it might take two. The only part that takes long is scanning each prescription. But now we’re building it so you can just take a picture in mass, instead of only one at a time. From there, they’re able to compare the plan, see which one they like, and then save the information. If you’re an agent, you’re able to save it direct into your company CRM (Customer Resource Management) if they have an enterprise plan. And if you’re a senior, you’re able to save it in your account, or export it as a PDF and text it to your agent, your caretaker, maybe your mom – anybody.
Wharton Global Youth: It’s really an efficiency tool. How long have you had an operating app?
Augustus: we recently launched the mobile app the second week of October. Right now, I consider it more of an open beta test, mainly because we had to push it out in time for this thing called AEP, which is Annual Enrollment Period. That period is between October 1 through December 10, and is when a lot of seniors start enrolling [in Medicare]. That two-and-a-half-month period is when a lot of agents need to be able to use the tool to enroll their seniors. That’s why we launched it. In that timeframe is when a lot of our users are going to need something that saves them a lot of time. It’s been going really well. A lot of people, a lot of downloads and a lot of early sales, because we are launching our enterprise tool pretty soon.
Wharton Global Youth: Do you have any metrics that show how you are having an impact on the market?
“CheckRx reduces 253 hours to maybe 30 minutes total, which is a huge, huge time saver for Medicare agents. That’s something that they loved with the product, so much so that we were able to charge $34.99, and they didn’t even bat an eye.” –Augustus Holm, Entrepreneur
Augustus: For the mobile app itself, those metrics are harder to gain until next year. But for our enterprise tool, which is a whole other thing [that] takes the core functionality of the app and makes it specific for Medicare agents, it saves them, on average, around 253 hours a year. The way that we calculated that was by meeting with about 60 different Medicare agents from different agencies – a nice random sample group, all from San Diego. We asked them, how many hours does it take you to be able to check your entire book of business, to be able to do this process on the mobile app? How long does it take you to check every year, because formularies, that list of drugs, changes. What drugs plans cover at what prices change every single year. So, Medicare agents have to constantly check. We asked them, and they said, Oh, yeah, it will easily take me almost half a thousand hours (on average 253, once we wrote it down). It eats into their time, because if they have a book of business of 150, 200 people, after doing this for five or six years, they have to go through each individual one. Instead of having to go manual with each person inside the book of business, we’re able to just press one button and it automatically checks the entire thing while also updating their intake forms, which is that list of prescriptions that a senior might have. It reduces 253 hours to maybe 30 minutes total, which is a huge, huge time saver for them. That’s something that they loved with the product, so much so that we were able to charge $34.99, and they didn’t even bat an eye. Also, we charge so much because it is a huge computational cost on our side, but they were more than happy to be able to pay it because of how much money they save in time.
Wharton Global Youth: We talked about pre-seed funding, right? You mentioned that friends and family helped you to get started with CheckRx. You also just closed your seed round, raising $750,000 total at an $8.88 million valuation. That is something! You’re actually referring to raising venture capital money to fund your startup. Can you walk us through this process?
Augustus: The process would have been difficult if I was trying to do it myself, or even trying to say, hey, mom, dad, do you know anybody that I can reach out to? Instead, I applied to a program called LBAN Startup Accelerator at Stanford, and I got accepted into it, which was super cool. I was the youngest person there, by far. At minimum, everyone was 23 or 24, so it was a bit intimidating. But once I got into the program, it was crazy useful. The amount of things that I learned and the amount of people I got connected to was awesome. And at the end of the program in April, they started connecting us to a ton of different VCs (venture capitalists) and angel investors. They were warm intros, which was nice. They would actually take a meeting with us and be willing to listen to what we have to offer. I met with 14 different VCs and angel investors over the course of about two months. Originally, I only wanted to raise $180,000 because we were ready to go to market. We needed final testing on the app and legal stuff, like a lot of legal compliance to make sure that we’re safe and secure. The core app was already finished a couple months [prior] to be able to launch, but it was all these additional expenses that were going to start eating us up.
But when I mentioned in my first two or three meetings that I was trying to raise $180,000, they said, okay, we love your product, but come back when you need half a million, because that’s too low. I’m asking for too little money? What do you mean? I’ve never heard somebody tell me that before. And they said, if you want cushion room. So, I [decided to] ask for more, but I didn’t want to give up more equity. But if that’s the only way that [I would be able to] get this additional funding, then it’s something that I’m willing to do. Plus, having cushion room is nice, right? That $180,000 was going to be eaten up within two months, just because those were all the expenses that we had anyway. By the end, once I was on my 10th or 11th [meeting], I had gotten pretty used to how this whole process would go, because definitely [during] my first couple I was a bit confused. [The VCs and angel investors] were really kind for helping guide me on what to say and how to do it.
Eventually, we got connected with a great angel investor who is based here in San Diego. I didn’t meet him through the LBAN program, but instead I met him through an investor I met at the LBAN program who said, this isn’t my industry, but I do know somebody who’s also in San Diego, because San Diego is big in biotech and health care. Once I met with him for lunch, he absolutely loved the product that we were building. I showed [him] the huge interest that we had. He said, okay, what you’re doing is really cool. Then I explained exactly what we would be spending all the money on — all of our expenses. And he realized, okay, a large chunk is going toward these testing fees, security and legal, but you already have the app done, and you already have people liking it. So for him, even though we had pseudo market validation (because a lot of time you need greater revenue to prove that), [we had] at least high customer interest from what we were building. That’s why he ended up investing, because he loved the product.
The reason that we got that $8.88 million valuation is, well, one I want to address the number 8.88 is a bit odd. He’s a very superstitious person, so for him, eights are a lucky number, like, 8888, and he was like, yeah, 8.88 is good. Okay! I’m not going to argue. We were talking to four different FMOs, which are field marketing organizations. Think of them as Medicare agencies. Each one of them might have 2,000 Medicare agents underneath them. And again, our product is meant for Medicare agents, so we were in talks with already four of them to be able to sign them on. The only thing they were waiting for was for us to officially approve the product with its security, because so far, there’s nothing else in the market that’s able to save people this much time. And when he saw that, and he attended some of those meetings that we had with them that went over the logistics, he realized this is real. You’re not just telling me that people are interested. You’re actually about to get these sales. Based off of how much we’re going to bring in within the next six months, we were able to lock down that $8.88 million valuation with his equity stake, which is nice.
Wharton Global Youth: All right, let’s wrap up with our lightning round. Answer these questions as quickly as you can.
Other than your own, your favorite Guinness World Record.
Augustus: It would definitely be a man who walked from LA to New York barefoot.
Wharton Global Youth: What is something about you that would surprise us?
Augustus: I am Peruvian, Japanese and Swedish, which is a fun mix.
Wharton Global Youth: How did you end up with the name Augustus?
Augustus: My grandpa’s name is Augusto, and mine is the American version of it, plus a “us”.
Wharton Global Youth: What’s the best piece of entrepreneurship advice
you’ve ever received?
Augustus: Grit can overpower talent.
Wharton Global Youth: If you could own one company in the world, which one would it be
Augustus: Boston Dynamics.
Wharton Global Youth: Should businesses prioritize profit or purpose?
Augustus: Purpose.
Wharton Global Youth: You are starting your own business-themed talk show. Who is your first guest and what is your first question to them?
Augustus: Elon Musk and what are his thoughts on somebody’s purpose within their life.
Wharton Global Youth: Augustus Holm, thank you for joining us on Future of the Business World.
Augustus: Thank you for having me.
Conversation Starters
Why is Augustus intrigued by the field of Medicare and what is the role of a Medicare agent?
What did Youth Philanthropy Council do to set a Guinness World Record? Have you ever set a world record? Share your story in the comment section of this article.
What are 3 things you learned about entrepreneurship and grit by reading and/or listening to this episode of Future of the Business World?