How This Mom Helped Her Son Win $100,000 of College Scholarships

how to get a scholarship
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When her son Josh started looking at colleges in 2008, Monica Matthews and her family faced a tough reality check.

“It was like, oh my gosh, we had no idea how much colleges cost, and we hadn’t saved for a college education,” she says.

A stay-at-home mom to two other young boys, Matthews didn’t want to go back to work. Looking for a way to fund Josh’s education, she found another solution: scholarships.

And it proved to be a pretty good idea.

Matthews eventually helped Josh win over $100,000, and now shares her strategies on her website How to Win College Scholarships.

Since I know many of you are worried about the cost of your children’s college education, I decided to pick her brain.  

Here’s what I learned about winning college scholarships

How She Helped Her Son Win $100K of Scholarships

After Josh applied for his first scholarship — and didn’t get it — Matthews decided to find out as much about winning as she could.

“I thought: I’m either going to have to go back to work, or I’m going to have to help him win scholarship money,” she says.

“I dedicated myself to figuring out what scholarship judges look for in their winners.”

A former teacher, Matthews created a system that allowed her and Josh to work together on his applications. The first year, she devoted four to five hours each week to scholarships.

“All of a sudden, he started winning,” she says. “It just kept coming and coming, and we had enough [money] for the first year.”

Before he even set foot in his college dorm, Josh had applied for about 35 scholarships — and won 13.

While studying aerospace engineering at the University of Michigan (go blue!), Josh continued applying for scholarships on his own.

In the four years between his senior year of high school and senior year of college, he won more than $100,000 — enough to cover his entire education.

“It’s been unbelievable,” Matthews says of their scholarship success.

“I was able to stay home and help my other sons,” she says. “I never had to go back to work. I never really had to worry about what we were going to do if we didn’t have the money for school.”

How to Get a Scholarship

Pretty incredible, right?

Since her process clearly works, Matthews created a business helping others emulate her scholarship success.

Below, she shares eight tips from her How to Win College Scholarships parent guide.

Keep reading to see how you could help your child win college scholarships — and hopefully graduate debt-free.

1. Start Scholarship Prep Early

It’s never too early to get ready for scholarship applications.

This “scholarship prep” involves helping kids gain experience with leadership and volunteering — both subjects they could discuss in an essay.

Not only that, those supervisors will “be the best ones to write your letters of recommendation because you’ll have volunteered there for years,” Matthews says. “Establish those relationships.”

Matthews’ youngest son, for example, is 14 years old and wants to major in engineering. So he joined a local robotics team — but Matthews didn’t stop there.

“There was a position open called ‘safety captain’ on our team,” she explains. “I jumped on it… That’s leadership already as a freshman in high school.”

2. Always Be on the Hunt

Thanks to the Internet, you have a wealth of scholarship resources at your fingertips.

Here are a few Matthews recommends:


This scholarship search engine should probably be your first stop.

Just be thorough when setting up your profile: Matthews says it’ll help you “weed out scholarships you aren’t eligible for.”

She also recommends setting up a separate email address, so your personal account doesn’t get spammed.

Scholarship Books

Scholarship guides provide a ton of information — the most well-known being The Ultimate Scholarship Book.

“I would take those books everywhere with me,” Matthews says.

“If I was waiting for my kids to get out of practice or whatever… I would page through them. You can buy them, but I checked them out from my local library.”


Yes, there’s even an app to help you find scholarships.

Scholly is a “simple, accurate and comprehensive scholarship matching solution that was created by students for students,” according to its site.

It’ll cost you $2.99 — a worthwhile investment considering the value of the scholarships you’ll find.

Your Future Alma Mater

If you already know which college or university your child is going to attend, be sure to look into its affiliated scholarships.

“The college itself is really a great way to help win scholarships,” Matthews explains. “They have endowment funds and money to give out for their own students.”

3. Focus on Your Strengths

You don’t need to be a perfect student to win scholarships.

If your child doesn’t have great grades, Matthews recommends applying for scholarships for leadership or volunteering.

“Look for scholarships that are based on skills — like photography, or making a video — rather than grades,” she says.

“Some scholarships — or actually a lot of them — don’t even ask for your GPA, or the minimum is a lot less than you’d think,” she says.

“There are some scholarships that don’t want the 4.0 kids. They want regular kids who have done something great for their community.”

She recommends a book called “The ‘C’ Students Guide to Scholarships,” since it focuses on highlighting leadership skills and other abilities.

4. Forge a Partnership With Your Child

One thing Matthews stresses? The scholarship process needs to be equally shared by both you and your child.

“Students are so busy,” she says. “That’s why this partnership thing works; you’re taking a lot of the pressure and time commitment off the students.”

Let them know, “I just spent all this time finding this scholarship — this is what you need to do,” she says.

That way your child knows you’re on their team, and doesn’t feel forced to write an essay without any guidance.

5. Complete the Applications in Small Chunks

Nobody wants to sit down knowing they’re about to spend hours on an essay.

So Matthews suggests completing the application in chunks.

“If you just ask for 15 minutes, most kids are gonna say, ‘OK, I can do 15 minutes,’” she explains.

And, after those initial 10-15 minutes, your student may want to keep going and finish, according to Matthews.

6. Use Money as Motivation

With Josh, Matthews says it was helpful to focus on the numbers.

“I kept his eye on the prize,” she explains. “I kept saying, ‘You know what, this college costs this much money. You can’t go there unless you win these scholarships.’”

She also used an hourly rate as additional motivation.

You can tell your child, for example, “If you win this scholarship for $1,000 and you worked on it for four hours, that’s like making $250 an hour,” she says. “Money speaks to kids.”

7. Make Your Essay Shine

Matthews offers several tips for the essay, which she calls the “heart of the scholarship application” and a “way for judges to get to know students on a deeper level.”

Start With a Hook

As with any piece of writing, a captivating introduction is essential.

“Get them to want to read to the very end,” she says. “Don’t start your essay with, ‘I need this scholarship money because…’ So many kids do that.”

“You need to start with something shocking like ‘My alarm rang at 5 a.m. I threw off the covers and I stomped into the bathroom to get ready to go to work.’”

Tell the Truth

Make it detailed, but don’t embellish, says Matthews.

Talk about your personal experiences and “show how you overcame an obstacle.”

Highlight the Organization

Show you’ve done your research by including the organization in the essay.

“Read the mission statement of that organization,” she says, “and align yourself to what they’re looking for. There’s nothing wrong with that as long as you believe in it.”

Read Through Winning Essays

A lot of websites share the essays of former scholarship winners.

“Read through the essays,” she says. “I’m not saying to copy — but get an idea of the kind of student they’re picking.”

8. Polish Your Online Presence

Though most scholarship applications are online these days, there are still ways to make your application stand out.

“Never leave any extra boxes,” she says. “Develop some Pinterest boards or a free website; Wix is great… You can have a link to your scholarship resume on there.”

Since online applications often have strict word count limits (which you should never go over), having a website allows you to provide more information.

“You can put in your link on the very bottom; it only takes up 20 characters and judges can click on it and find out a ton more about you,” Matthews explains.

If the application happens to require printing and mailing, make sure everything’s in the correct order and not folded up.

“Spend a dollar and put it in a nice envelope,” she says.

It Sounds Like a Lot of Work… But Is it Worth it?

There’s no doubt about it: Successfully applying for scholarships is a lot of work.

But Matthews firmly believes it’s worth it.

“You put in the work now, and then while you’re in college, you’re not working,” she explains.

That’s in stark contrast to Matthews’ college experience, when she worked “all the time.” Her biggest motivation was (and is) the fact she doesn’t want her kids to have to do the same.

If you don’t think you have time to pursue scholarships, she recommends starting slowly.

“You’re watching TV and a commercial comes on,” she says. “Grab that scholarship book or your cell phone, and start looking through and jotting down notes.”

“When you’re surfing on the internet, spend 15 minutes a day looking for scholarships,” she urges. “You can make the time if you really try… It’s all about priorities.”

Your Turn: Will you help your child with their scholarship applications?

Susan Shain, senior writer for The Penny Hoarder, is always seeking adventure on a budget. Visit her blog at, or say hi on Twitter @susan_shain.