Help with College Applications: Ben Kaplan Shares His Road to Harvard and Scholarship Success

Hello parents, this is Shellee Howard, the founder and CEO of College Ready. And today on Parents, Is Your Teen College Ready? I have an amazing guest, Mr. Ben Kaplan. Welcome to the show.

Thank you, Shellee, for having me. It's great to be here.

Can you tell our guests a little bit about your background and what we're going to be able to discuss today?

Sure. You know, back in, in the day, I was a high school student that had no clue how to pay for college. I had grown up and I was a competitive tennis player. I thought I'd go to school on tennis scholarship, but I got an injury injury in my back. I recovered, I was okay, but I suddenly needed a different way to pay for school. And so I, you know, hustled around and it was my, I remember my junior year in high school and I found my first scholarship application and I was like, what is this? You know, wants me to write a little essay and do a couple letters of recommendation, very similar to a college application, maybe a shorter one. And I filled it out, I sent it off. And to my amazement, I got this phone call and the voice said, congratulations, you've just won $15,000 in, from Discover Card. At the time, the credit card company. And so I was like, wow, what else is out there? So over the next year, I applied for about 3 dozen scholarships. I won about 2 dozen of them, accumulated $90,000 in scholarship money, which was a credential that helped me get admitted to Harvard and pay for almost everything. And so for me, it, it, this process changed my life. And, and this was, I mean, you know, I guess now, I mean, this was 1999, so a long time ago. And I wrote a book called originally a book called How to Go to College Almost for Free. I self-published it and sold 2 million copies of this book. And then years later now, I've done a lot of other things in my career, but like, I wanted to— I just felt like, you know, no, the, you know, as you know, Shellee Howard, like the issue of paying for college has not been solved. It is a huge, you know, for so many families, it is like the biggest purchase you'll ever make aside from maybe a home mortgage. And if you have multiple kids, it could even be bigger than your own mortgage. Right. And so I just wanted to do something to do the book that I wish I would have had when going through it. So I wrote this new book. Just come out. It's called Scholars and Dollars, and it's meant to go through admissions, financial aid, scholarships, school success, your first career job in your career, and ultimately personal growth through this process. And it's all based on like my personal experience and, and at this point tens of thousands of other students I've coached through the process.

I love it. So parents, again, we're always looking, how do we make your life a little less stressful by bringing our guests to you? I bet you are wondering, Ben, when you were in high school, did you know exactly what you wanted to do and where you wanted to go to college?

I didn't. I didn't. And I think the good advice I had was that when you didn't know what to do, try a lot of stuff and sort of see, because it's one of those things like, like, you know, and I sometimes talk about this, like, you know, maybe your calling is, I don't know, anthropology, maybe that's it. But like, I don't know a lot, you know, in high school, I probably didn't have any idea what anthropology was. I probably had no exposure to it. So you have to try a lot of things to sort of find what what works. And then as you do that, I think the, the other question I get too is like, you know, how do you structure all of that for to get into a college, to win a scholarship? And what I would say is that you kind of like, I, I think it's, it's, there's value in trying a lot of things. So you have like a lot of breadth, but then the things that do stick that you are interested in, you are passionate about, go deeper in those things, sort of have that breadth., but then have that depth as well. And so I didn't know, I, I didn't have it figured out, but I think one of the underappreciated benefits of the college admissions process and financial aid processes, I think that for a lot of students, this is the first time you're really like, let's, let's take the reins of your, of my future. Right. You might have a lot of help from your parents, but you're a stakeholder in this, right? It's not just a parental thing anymore. And so I think that is like a precedent-setting milestone. If you approach it as, you know, oh gosh, college is incredibly tough. It's expensive to get in. It's expensive. And what am I ever gonna do? And I, I just give up, you know, it's not worth it. Then that's, that sets a precedent, right? And your first big milestone in your life, that's easier to sort of make that similar decision elsewhere. But if you take the other hand, the other approach, which is like, yes, this is challenging. Yes, this is difficult, but like, I can take some small action steps. I can get progress. I can get advice from others who've been there. I can get advice, you know, Shellee Howard's gonna help me. Oh, I, I can check out what Ben said. Oh, I wanna talk to other people who are older students who've been there and done that, and what, what advice can I glean? And I'm gonna make progress every day. If you take that approach, that's also a precedent-setting milestone that gets easier to do that in other decisions you'll have to make in your life.

So important. And you know, I have found, and you might as well, the students who struggle narrowing it down are good at a lot of things. It's not that they're not good at anything, it's just they may be good at more things than just one subject. And so they feel torn in many different directions. But let's talk just a moment how— let's, let's talk about your story, right? So you, you might have had a, a plan and you were a scholar athlete, but as far as your major goes, as far as like, how did you decide what path you were going to take and what was the dream?

Well, I wanted to— I thought I wanted to be— I like to write, and I thought I wanted to be maybe a syndicated political columnist. I liked following news events. I like politics. I thought I would maybe want to do that. And I was, you know, there's not really a— I mean, I guess you could get maybe a— you could get options included, like an English degree. Maybe you could do that. You could get a political science degree, right? You're going to want to have a policy. You could do that. I ended up doing economics because I thought it was like useful to understand economics if you want to be a syndical economist. But there was also— it gave you like— I was also a quantitative person. I could, I, you know, I thought it would give me like quantitative skills. And I, and I tried that. But what I would say is, my advice to other maybe, maybe parents or students listening is in terms of the college choice, I didn't really go with like, oh, this college is, you know, I don't know, great in economics, therefore I should go to it. Because that can change. That is something that's— I think to me, in my mind, the number one most important thing, if I was me if you agree, Shellee Howard, if you— when you choose a college is that— and, and tons of studies have, have sort of shown this is the biggest determinant of whether you do well in school. And that is, does the college and its community feel like home? I don't mean feel like home like it's just like your house where you grew up, or it's just like your town. It could be very different. But the idea is that, are you part of something and it feels like you're not just a number? You're part of something where a community that cares about each other. You're a part of something bigger than yourself. And lots of things, you can find different places that have different, like, you know, great departments in this or that, or have, and, and, and, but that, that feeling of togetherness is a huge determinant in how successful you'll be. And the other analogy I use is it's a lot like, like lifting weights. If you ever worked out in the gym, you, you want a place that like challenges you a bit, right? You don't want to drop 400 pounds on yourself and force yourself to bench, but that's going to be too much. But you wanna challenge yourself to go a little bit beyond what you've done. But at the same time, you don't wanna go to a place where it's like you're lifting 1-pound weights. You can do that all day long. It's too light. So find a place that feels like home, someplace that challenges your comfort zone a bit, but not overwhelming. And not that it's too— doesn't challenge you at all. And if you do that, I think you set yourself up for success, even if you change your major, even if you change your career path.

Yeah, it's fascinating. I use something similar, only I use, do you want to be the big fish in the little sea or the little fish in the big sea? Which is basically stating the same thing, is that fit where you're at is so critical. Because I know that, and you might have experienced it as well, when my son was at Harvard, he was mentoring other students as the freshmen came in, and there was either a quick fit or a fit that was really hard to get to. Some kids had always been at the top of their class and it came easy, and then they hit Harvard and everybody's the top of their class. And there was a lot of like, wow, I'm not that person anymore. And I remember my son's story is the teacher said, one of you will get an A, and he's like, I guess I'm getting my first B, because he was okay with that. What about your experience at Harvard? Did you have something similar?

I did, in the sense that— and this is, it goes back to why community is so important, feeling like you can draw upon other resources, because I think, you know, I ended up in a, in a math class there and it's like in this math class, I later discovered that like, there's like multiple people off the US Math Olympiad team in my math class. Like, holy cow, we're graded on the curve. Like, oh my God. Like, like there's people there who like represented our country in math and international math competitions and they're in my class. Right. So you experience a little of that, but, but I think what gives you a lot of confidence. And this is where it's like part of a community, or if you have the right attitude, or if you go there, is like, you realize like, okay. And, and I think this is true of a lot of colleges. Like, wow, everyone here at this university, there's everyone who can do something way better than me.

Mm-hmm.

Absolutely. But in my little niche, in my little thing that I do unique, there are some things that I do that other people, you know, can't quite maybe do as well as I do. And that actually gives you confidence. 'Cause at first it humbles you and you're like, oh my gosh, like that person, that math is at such a different level. I, I can't even, we can't even, we shouldn't even be in the same class, right? Like it's crazy. But then you're like, oh, in my unique way, here's what makes me special. And I think when you get to that, that gives you confidence and it takes off pressure because you're like, I don't have to be the best at everything to everybody. I just need to be my unique special self, and there's some ways that I can do that.

That's so beautiful. Parents, what I'm hearing, and I hope you're hearing, is that fit and preparing your child for those things that will come up, right? The, the opportunity to realize, to be humbled, that yes, in their high school they may have been valedictorian and whatever, and now they're amongst others, I think is so huge. So how do you—

and even that community, just to— sorry, to build on what you said, is like you get to a certain point when you feel like you're part of a community that takes care of each other, you're as strong as your community. So what's exciting about that is like, oh, that person who's great in math or that amazing athlete or that person who, you know, is far beyond their years in some, you know, piano playing or something else, they're part of my community. I'm stronger because of them. We're stronger together. We is greater than me. And that's empowering. Sorry, keep going.

No, no, absolutely. And, you know, having that mindset, you were brought up as a tennis athlete, good enough potentially to do it at a very high level. I always like helping families understand, and it's okay to fail because when your child's at home and they have these little bumps in the road, you're preparing them for what's truly in front of them. And so sharing your story made me realize of how many students that I get a chance to celebrate their wins and their, oh my goodness, I wasn't as good at that as I thought I would be. So thank you for sharing that. Let's switch gears a little bit and let's talk about Scholars Scholars and Dollars. And, and maybe you can dive into what inspired you to write that book.

Sure. You know, Scholars and Dollars, I, I wrote this book and it's just come out this year, you know, early 2025. And there's so many rules of the road that if you are clued into what they are, you can navigate and you can steer this so much better. But no one really tells you this. I mean, maybe you get lucky and you have, I don't know, a friend who's been there, done that. Or, or I know in, in your case, Shellee Howard Howard, you have multiple kids, right? You like maybe didn't have it figured Not as much on like the eldest, but like by the time you got through this a couple more times, right, you sort of figure it out. And so I wanted to do all of like, to just break down short actionable chapters on these key leverage points that just swing a lot of your personal finances, your admission success, your school success, have a huge impact. Let me, let me give you an example. So on the financial aid side, there is like, you know, over the years, like you probably as well, I, I've coached many families that have special circumstances, right? That is like, okay, you You fill out the FAFSA form, this is the number it spits out. And you're like, oh, but we have high medical expenses in the family. Or, oh, our income is super variable. Like last year was a great year, but that's not every year. And, or, oh, we just had a large inheritance, right? A relative passed away, but that, that's overstating our resources. So that would always come up. And there's a secret password actually to deal with that. And that secret password is professional judgment. And if you're in the industry, you know what that is, which is professional judgment is the power given to an individual financial aid officer to make adjustments for your special circumstances. But what they don't do is say, oh, well, Shellee's, you know, had it tough, or Shellee's, you know, needs a bit more. Let me just boost her output, the aid she gets. What they do is they adjust the inputs. So they say, oh, if, you know, if you have, you know, overstated income and you can document that your income is not usually that high, maybe we'll take an income figure from your 3-year average. Not your most recent year, and we'll use that instead. And then say, if we put that in, what's the result in the financial aid? So I've seen families have $50,000 swings in financial aid based on the professional judgment treatment. Now that is something in my mind, like everyone should know, everyone should know this is the code word professional judgment. Yet you don't really learn that unless you've been through it a few times, you know? So I think. That is what this Scholars and Dollars book is full of. It's like the key leverage points you could use that have the biggest effect on the end result.

Oh my gosh. And, and it makes so much sense. So you, you still have little kids. By the time they go to college, like you're gonna have this whole thing. College is gonna pay them.

I, I hope so. I'm, I'm, I'm a little bit scared to see what college costs. I have a 2-year-old and a 4-year-old, what that's gonna be, but we'll see. Yeah, we'll see. Yes.

When my firstborn was going through it, right? Like you said, it's kind of your, the, the guinea pig for everything, the pacifier, the whole thing, but I, when, when you brought up professional judgment, we actually used that and it's because I'm a business owner and I approached it as a business and I said USC offered a full ride scholarship. USC, it's not a, not a little tiny school. It's a legit school, Harvard. And I said, so with that in mind, we'd like a financial reconsideration because you're asking him to go from West Coast to East Coast. And he's going to provide that diversity that you're looking for in your pre-medical department. And we had this whole business proposal laid out exactly like you said, and it was amazing how much endowment money was available. So I tell you, parents, I know it's emotional, but it is also a business. So in your book, you outline some things they can do, which is so critical, and you're on a mission, right, to make this happen, which we are fully aligned on. I love it.

Now, and, and, and the one thing I'll Almost everything he said, I 100% agree with. And I would just say that I actually think that there is so much overlap between college admissions, financial aid, and also merit-based scholarships that people sometimes don't realize. Meaning when you've done a college application well, you've done 80% of the work to apply for 10 scholarships. You can recycle, reuse, and redeploy for that. When you do a scholarship application and you hone that message of like, like really showing who you are, not just what you've done. That improves your college essay and painting that portrait that's going to get you admitted. So I actually think I'd just say that people are always like limited in time. I get asked like, well, how do I have time for all this? Well, if you approach it holistically, it's just incremental extra effort to leverage what you've already done has huge results.

That's well said. Well said. So let's talk a little bit about how do you find scholarships, right? You made it sound like Well, I'm 80% done once I complete my application. Can you maybe give some words of advice or encouragement for those families who are feeling a little frustrated that they make too much and not enough?

Sure. First of all, there's a number of free scholarship databases you could search, and we've created one. It's at our website, scholaroo.com. So it's like, it's almost like a kangaroo, like an OO at the end, but scholaroo.com. And you can, and what we've actually done is a lot of people were frustrated with some of these other databases because they would sort of like hold back results and they would like more like want to get you on a list to market to you and sort of drip these out. So we just said like, let's just open up the whole database. So it's not like we're hiding things. You can just sort of see the whole thing. You can search for yourself. So one, you can use some of these databases. Two, I actually think one of the big overlooked methods is checking out your own school's resources, but not just the resources of your own school, other schools in your area and beyond. So a lot of schools, students have get sort of direct mailings of scholarship opportunities to the school, but most schools are not comprehensive in this. So one thing I would always do is I grew up in Eugene, Oregon. I went to South Eugene High School. There were 4 other high schools in my town. I would actually check the websites and eventually I knew other parents. They would like go check for me their actual career centers for what other scholarships were there. So I found tons of scholarships that I would not have found otherwise, but I would check high schools. I would check colleges and universities in my area and the one little tip the first tip I learned is I would never neglect the small local scholarship. It was multiple times where it was like $500. And sometimes it's like I wasn't even exactly what they were looking for. It was like some very specific criteria. I didn't quite fit. And in one case, they actually came to me and said, no one else applied. You don't really fit, but like, we want to give it to you. You seem worthy of the money. And those smaller ones were a credential I used to win the bigger ones. So it was like I treated it like an award, a prize, recognition that helped me get the $20,000 scholarship. So that would be my advice is start with scholarship search databases, scholaroo.com, use school resources, but not just your own school, and don't neglect the small local scholarships.

Oh my gosh. So much great advice. So much great advice. One piece to that I'm going to add on because of that awesomeness is I always recommend families that you have a throwaway email. In other words, create an email that at the end of scholarship searching, that it's not your daily email because you will continue to get a barrage of wonderful resources thrown at you and you're going to be done by then. So do not— I made that mistake. I gave out my personal email or my son gave out my personal email and I had to trash that email. It never recovered. So just a little tidbit of advice from somebody who's been there. Just do a very first name, last name at @gmail.com or whatever your favorite is. So in finishing, I would love for you to share how can my clients or the, the people who are listening get in touch with you, learn more about your book. How, how can they connect?

Okay, sure. Well, one, I, I, I'd love to hear from you. I would love to. It's, I should tell you, like, you know, I am doing this like 25 years after doing it the first time because I just wanna like reconnect with like my purpose and passion. And it's like I have this goal of like, like, you know, in helping people get a billion dollars in scholarships and financial aid in my life. Like, that's a big goal. So, so one, I'm doing this now just out of passion. And so I'd love to hear from you.

I—

the website is scholaroo.com, like scholar-oo.com. And also, and, and the book is on, you know, Amazon's probably an easy place to get it. It's called Scholars and Dollars. But I also do a site, it has a, it has a fun name. It's called Learndipity, like learning and serendipity, like learn, L-E-A-R-N, dipity, D-I-P-I-T-Y.com. And I also do a bunch of courses on there that are hard to find elsewhere. So right now I have one called Scholarship Seekers Toolkit, and it takes you through the 17 sort of steps of finding scholarships. You get personal advice, you can get your, your essays, get feedback on your essays, and it's just in this sort of course structure. So that's the other sort of passion project. And my day job is I, I have another couple companies. I'm an investor. But this is like pure passion. So, so check that out, learn-dipity.com or scholaroo.com, and would love to have you in the course.

Such great resources, Ben. Thank you so much for being on the show. And parents, until next time, make sure your student is ready for college. Have a great—

thank you, Shellee Howard.

You got it.