Ol' College Try

Matt and Peg's College Planning Podcast
  • 4.4 (10)
  • EDUCATION
  • UPDATED WEEKLY

Let’s give the college planning game an Ol’ College Try—together. New episodes every Thursday at 12PM ET. Ol’ College Try is your go-to podcast for students, families, and educators ready to tackle the college planning process with confidence. Hosted by Matt Carpenter, Co-Founder of College Aid Pro, and Peg Keough, Director of Education, each episode breaks down the ins and outs of financial aid, scholarships, student loans, and smart college planning—without the overwhelm. 💡 Get expert insights, insider strategies, and the latest updates to make college more affordable and less stressful.

  1. Private Scholarships Demystified: How to Find Them, Win Them, and Avoid Costly Mistakes

    15H AGO

    Private Scholarships Demystified: How to Find Them, Win Them, and Avoid Costly Mistakes

    Private scholarships can feel overwhelming, confusing, and sometimes too good to be true. So how do families actually use them to lower the cost of college? In this episode of The Ol’ College Try, Peg Keough sits down with Jocelyn Pearson, founder of The Scholarship System, to do a deep dive into the world of private (aka external) scholarships. Jocelyn shares how she personally earned six figures in scholarships—enough to graduate debt-free with overage checks—and how families today can create a repeatable strategy to do the same. You’ll learn: The difference between private scholarships, merit aid, and need-based grants Why your FAFSA Student Aid Index does not automatically disqualify you How to identify your student’s unique “scholarship superpower” Which scholarships are worth your time (and which are just sweepstakes in disguise) When to start applying—and why junior year is ideal How recurring scholarships work What scholarship displacement is and how to protect your award If your family falls into the “income gap” and you’re worried about taking on debt, this episode will give you practical, actionable steps to start closing that gap the smart way. Whether you have a high school junior, senior, or even a current college student, it’s not too late to build a strategy that works. Tune in and learn how to turn private scholarships from a buzzword into a real plan.Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Sign Up for Our FREE College Success Bootcamp: https://hubs.li/Q042SVt10 Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸 Connect with Jocelyn! Website: ⁠⁠https://thescholarshipsystem.com/ Sign Up for Her Free Master Class: https://thescholarshipsystem.com/mycap/

    40 min
  2. High School Counselor Insights: What Makes a College Application Stand Out

    FEB 5

    High School Counselor Insights: What Makes a College Application Stand Out

    In this episode, Peg Keough sits down with fellow Jersey girl and longtime College Aid Pro advocate Lisa Burfeindt, Director of School Counseling for the Cranford Public Schools—and an application reader for UC Berkeley. With decades of experience guiding students and families through the college process, Lisa brings a rare dual perspective: what high school counselors see and what really happens once an application lands on an admissions desk. Together, Peg and Lisa dive into what makes a strong college application, common mistakes students make, and why authenticity matters far more than perfection. They discuss: How colleges (yes, even large public universities) actually read applications Why depth matters more than a long activity list What admissions readers look for beyond grades and test scores How essays can make or break an application—and why they don’t need to be dramatic The role of AI in application writing and how inconsistency can hurt students Why finances should be part of the college conversation from day one How parents can best support their students without steering the ship for them Whether you’re a parent, student, or counselor, this episode is a must-listen reminder to take a deep breath, stay authentic, and remember: there is no such thing as only one “right” college. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    38 min
  3. Monthly Grab Bag: FAFSA vs. CSS, AI Anxiety, and Other Questions Keeping Parents Up at Night

    JAN 29

    Monthly Grab Bag: FAFSA vs. CSS, AI Anxiety, and Other Questions Keeping Parents Up at Night

    College costs feel overwhelming—and this week on Old College Try, Matt Carpenter and Peg Keough open up the grab bag to tackle the real questions families are asking right now. From understanding the difference between FAFSA (federal methodology) and CSS Profile (institutional methodology), to how rental properties, LLCs, trusts, inheritances, and child support impact financial aid, this episode goes a level deeper for families who want to understand how the system actually works. They also zoom out to talk about the bigger picture: Is college still worth it with AI reshaping careers and majors? Why sticker price is misleading—and how families can still get strong outcomes Why relationships, networking, and adaptability may matter more than ever If you’re trying to plan smart, avoid unnecessary costs, and feel less in the dark about the college funding process, this episode is packed with clarity, context, and practical insight. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    36 min
  4. Appealing Need-Based Financial Aid: A Step-by-Step Guide for Parents

    JAN 22

    Appealing Need-Based Financial Aid: A Step-by-Step Guide for Parents

    If your child was accepted to college but the financial aid offer doesn’t reflect your real financial situation, you may be able to appeal — and win. In this episode, Matt Carpenter and Peg Keough explain how need-based financial aid appeals work, who should lead the process, and how colleges evaluate income, assets, businesses, and home equity. You’ll hear practical advice, insider insight from former financial aid professionals, and examples of appeals that resulted in tens of thousands of dollars in additional aid. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    34 min
  5. Merit Scholarship Appeals: What Works, What Doesn’t, and When to Ask

    JAN 15

    Merit Scholarship Appeals: What Works, What Doesn’t, and When to Ask

    Merit scholarships aren’t always final—and a smart appeal can make a real difference. In this episode of The Ol’ College Try, host Peg Keough sits down with Mike Hinderman, Director of Scholarships at the University of Oklahoma (and a CAP financial expert), to get the behind-the-scenes scoop on how merit appeals actually work. Mike breaks down OU’s approach to automatic merit scholarships, what the appeals process looks like, and why your admissions counselor can be your best ally. They also dig into what separates a strong appeal from one that gets ignored—like why the student must lead the appeal, how to share the right “missing context” (awards, leadership, challenges overcome), and what language to avoid (hint: “price match” and demands don’t land well at many public universities). Plus, Mike shares real examples of appeals that stood out to committees and why timing and demonstrated interest can influence outcomes. If your family is staring at an award letter and wondering “Can we ask for more?”—this episode is your playbook. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    40 min
  6. Financial Aid Award Letters Explained: Grants, Scholarships, Loans & What You Really Owe

    JAN 8

    Financial Aid Award Letters Explained: Grants, Scholarships, Loans & What You Really Owe

    You got the acceptance letter—now what does the financial aid offer actually mean? In this episode of Ol' College Try The Podcast, Matt Carpenter and Peg Keough break down one of the most confusing parts of the college process: financial aid award letters. From grants and scholarships to loans and work-study, they explain how to read between the lines, spot misleading language, and understand what you’ll really pay—not just this year, but over all four years. You’ll learn: The difference between merit scholarships and need-based grants (and why it matters long-term) How to tell when you’ve received your final financial aid offer Why loans and work-study can make a college look cheaper than it actually is Common red flags on award letters that families often miss What underclassmen parents should be thinking about now to avoid surprises later Whether your student is Class of 2026 and actively receiving offers—or you’re planning ahead with a younger student—this episode will help you make smarter, more confident decisions about college affordability. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    31 min
  7. Four College Resolutions Every Family Should Make This Year

    JAN 1

    Four College Resolutions Every Family Should Make This Year

    It’s a New Year’s special on Old'College Try, and Matt Carpenter and Peggy Keough are kicking off 2026 with the college-focused resolutions every family should consider. In this episode, Matt and Peggy each share two practical, high-impact resolutions designed to reduce stress, improve communication, and lead to better college and financial outcomes. From starting honest conversations early, to understanding academic, personal, and financial fit, to teaching students how to advocate for themselves through financial aid appeals—this episode is packed with real-world advice families can actually use. You’ll hear why transparency matters, how to give your student ownership without losing guardrails, and why “never accept the first offer” is a life skill—not just a college strategy. If college is anywhere on your family’s horizon, this is the perfect way to start the year informed, confident, and prepared. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    20 min
  8. Holiday Q&A: Financial Aid Appeals and FAFSA Myths with a Special Guest

    12/25/2025

    Holiday Q&A: Financial Aid Appeals and FAFSA Myths with a Special Guest

    In this special holiday edition of Ol’ College Try, hosts Matt Carpenter and Peggy Keough tackle listener-submitted Q&A questions just in time for the end of the year. From financial aid appeals at state schools to common FAFSA and CSS Profile misconceptions, Matt and Peggy break down what families really need to know—without getting lost in the weeds. This episode covers: How student and parent assets impact financial aid Whether retirement accounts affect FAFSA and the CSS Profile When and why it’s worth appealing a financial aid offer (even at state schools) How colleges think about full-pay families versus discounted offers When families should start working with College Aid Pro—and why earlier is better Plus, the episode wouldn’t be complete without some holiday fun. Matt’s daughter, Emma Claire Carpenter, joins as a very special guest to answer the toughest Christmas questions of all—what’s on her wish list and what she loves most about the holidays. Whether you’re navigating senior-year stress or just starting to think about college planning, this festive Q&A episode offers practical insights, reassurance, and a reminder to enjoy the season. Happy holidays from the Ol’ College Try team! Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0Instagram: ⁠⁠https://www.instagram.com/collegeaidpro/ ⁠⁠LinkedIn: ⁠⁠https://www.linkedin.com/company/college-aid-pro/ ⁠⁠Email: ⁠⁠support@collegeaidpro.com⁠⁠ PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    28 min
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4.4
out of 5
10 Ratings

About

Let’s give the college planning game an Ol’ College Try—together. New episodes every Thursday at 12PM ET. Ol’ College Try is your go-to podcast for students, families, and educators ready to tackle the college planning process with confidence. Hosted by Matt Carpenter, Co-Founder of College Aid Pro, and Peg Keough, Director of Education, each episode breaks down the ins and outs of financial aid, scholarships, student loans, and smart college planning—without the overwhelm. 💡 Get expert insights, insider strategies, and the latest updates to make college more affordable and less stressful.

Information

  • Creator
    Matt and Peg's College Planning Podcast
  • Years Active
    2025 - 2026
  • Episodes
    53
  • Rating
    Clean
  • Copyright
    © Matt and Peg's College Planning Podcast
  • Show Website
    Ol' College Try

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