Ol' College Try

Matt and Peg's College Planning Podcast
  • 4.3 (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. College Payment Plan Explained: Loans, 529s & What to Do Before Decision Day

    6D AGO

    College Payment Plan Explained: Loans, 529s & What to Do Before Decision Day

    Making your final college decision? You’ve got a number—but do you actually have a plan to pay it? In this episode, Matt and Peg tackle your biggest end-of-month Q&A just days before the May 1 deadline. From 529 strategies to student loans and financial aid, they break down what families should be thinking about right now to avoid costly mistakes. Making your final college decision? You’ve got a number—but do you actually have a plan to pay it?In this episode, Matt and Peg tackle your biggest end-of-month Q&A just days before the May 1 deadline. From 529 strategies to student loans and financial aid, they break down what families should be thinking about right now to avoid costly mistakes.They cover:Why you shouldn’t spend your entire 529 in year oneHow to maximize the $2,500 American Opportunity Tax CreditWhat happens if your 529 doesn’t cover all four yearsWhat to do with leftover 529 funds or unexpected scholarshipsHow the CSS Profile works and what to know about non-custodial waiversThe difference between 529s, prepaid plans, and UTMA/UGMA accounts Plus, real talk on why there’s no one-size-fits-all strategy—and how a little planning now can save you thousands later. 🎧 This week’s intro song: You Send Me by Sam Cooke Bottom line: Don’t just focus on getting in—focus on how you’re paying for all four years. Got questions for our next Q&A episode? Send them our way—we’d love to hear from you! Connect with Us! Student Loan Fact Sheet: https://hubs.li/Q04cmnWD0 Website: ⁠⁠https://collegeaidpro.com/⁠⁠ Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0I nstagram: ⁠⁠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 💸

    32 min
  2. College Waitlist Explained: What It Means, Your Chances & What to Do Before May 1

    APR 23

    College Waitlist Explained: What It Means, Your Chances & What to Do Before May 1

    Waitlisted? You’re not alone—and you’re not out of the game… but you’re not in it either. In this episode, Peg is joined by CAP expert Dan “Lasso” Bisig to break down one of the most confusing parts of the college admissions process: the waitlist. What does it actually mean? How do colleges use it? And what should families be doing right now if their student is stuck in limbo? They cover: Why colleges rely on waitlists (and why it’s not about you)What students should do immediately after being waitlistedThe reality of getting off the waitlist—including tight decision timelinesHow financial aid works (or doesn’t) in waitlist situationsWhy you must have a backup plan before May 1The mindset shift every family needs to avoid unnecessary stressPlus, a real-life story of getting “the call” from a dream school—and what families should be ready for if it happens. 🎧 This week’s intro song: Born in the U.S.A. by Bruce Springsteen—a high-energy classic to get you fired up. Bottom line: Treat a waitlist like a “maybe,” plan like it’s a “no,” and move forward with confidence. Got questions for our next Q&A episode? Send them our way—we’d love to hear from you! Connect with Us! Student Loan Fact Sheet: https://hubs.li/Q04cmnWD0Website: ⁠⁠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.com⁠⁠PLUS Get 15% OFF site wide with coupon code COLLEGETRY15 💸

    35 min
  3. The Final Countdown to May 1: Making the Right College Decision

    APR 16

    The Final Countdown to May 1: Making the Right College Decision

    With the May 1 college decision deadline fast approaching, this episode breaks down exactly what families need to be doing right now to make the smartest possible choice—financially and academically. Matt and Peg dive into real-world strategies for navigating this critical moment, including when (and if) it makes sense to put down multiple deposits, how to handle schools delaying financial aid appeal decisions, and why colleges don’t always have your financial best interest in mind. They also walk through what happens after you commit—covering timelines for bills, how to actually pay for college, and the smartest ways to use 529 plans without leaving money on the table. Plus, they unpack how much student debt is “too much,” and how families can avoid costly mistakes that follow students long after graduation. Whether you're a senior racing toward Decision Day or an underclassman hoping to avoid the same stress, this episode gives you a clear, practical roadmap to finish strong—and start college on the right financial footing. 🎧 Song Picks from This Episode: “Honeybee” – Goose“Hungersite” – Goose Plus, a shoutout to Bruce Springsteen (“The Boss”)—still delivering unforgettable live performances. Connect with Us! Student Loan Fact Sheet: https://hubs.li/Q04cmnWD0 Website: ⁠⁠https://collegeaidpro.com/⁠⁠ Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0 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 💸

    32 min
  4. Too Rich for Aid, Too Poor to Pay: Inside College Costs with Dr. Jason Slone

    APR 9

    Too Rich for Aid, Too Poor to Pay: Inside College Costs with Dr. Jason Slone

    What if everything you thought you knew about paying for college… was wrong? In this episode of Ol’ College Try, Matt sits down with Dr. Jason Slone—former professor, dean, financial advisor, and now CAP College Affordability Expert—to break down the reality behind college costs and financial aid. Jason shares his unique journey from small-town Ohio to academia, the private sector, and ultimately helping families navigate one of the biggest financial decisions of their lives. Along the way, he unpacks why so many families feel “stuck in the middle”—too wealthy for aid, but nowhere near able to comfortably afford $300K+ for college. You’ll learn: Why college prestige is often overratedHow to have honest (and productive) money conversations with your kidsWhat most families misunderstand about financial aidWhy “fit” matters more than rankingsHow to think like an adult when making college decisionsPlus, Jason shares insights from his new book Too Rich for Aid, Too Poor to Pay—a quick, practical guide designed to help families cut through the noise and lower the cost of college. 🎵 Song Pick of the Episode:Domino College by Jimmy Buffett If you enjoyed this episode, don’t forget to follow, share, and leave a review—it helps more families find the guidance they need. Connect with Jason! Too Rich to Pay, Too Poor for Aid by Jason Slone: https://a.co/d/04mqvH3x Linked In: https://www.linkedin.com/in/jason-slone-phd-ccfc-578601231/ Learn More & Book an Hour with Jason (use code COLLEGETRY15 for 15% OFF your hour): https://collegeaidpro.com/college-experts-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 💸

    37 min
  5. The Truth About College Admissions: Essays, Odds & Financial Reality

    APR 2

    The Truth About College Admissions: Essays, Odds & Financial Reality

    What does it really take to get into college today—and is it worth the cost? In this episode of The Ol’ College Try, Peg Keough sits down with former Stanford student, longtime English teacher, and college essay expert Mark Hernandez to break down the realities of the admissions process. From the myth of “perfect stats” to the truth about how decisions are actually made, Mark shares what he saw firsthand after 25 years working with high-achieving students. They dive into: Why great grades and test scores aren’t enough anymoreThe biggest mistakes students make on college essays (and how to stand out)Why “I’ll figure out the cost later” is a dangerous mindsetThe growing pressure of competition and social mediaHow families can approach college as a financial decision, not just an emotional onePlus, Mark shares actionable advice for students on writing bold, authentic essays—and for parents on supporting their kids without adding stress. If you’re navigating the college process, this episode will help you think more clearly, plan smarter, and avoid costly missteps. 🎓 Featuring insights from a Stanford grad, veteran educator, and admissions insider perspective you won’t hear anywhere else. Connect with Us! Website: ⁠⁠https://collegeaidpro.com/⁠⁠ Create a FREE MyCAP Account: https://hubs.li/Q03PTJ_x0 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 Mark Hernandez! Instagram: https://www.instagram.com/englishwithmarkh/ TikTok: https://www.tiktok.com/@englishwithmarkh Website: https://englishwithmarkh.com/

    35 min
  6. Student Loans, Myths & Middle-Class Reality: What Families Need to Know Right Now

    MAR 26

    Student Loans, Myths & Middle-Class Reality: What Families Need to Know Right Now

    In this open Q&A episode of Ol' College Try, Matt and Peg tackle some of the biggest (and most misunderstood) questions families have about paying for college. From Parent PLUS vs. private loans to loan forgiveness for teachers, they break down what really matters when borrowing for college—and how to avoid costly mistakes. They also dig into the reality for middle-class families who feel stuck between “no aid” and “can’t afford it,” and explain why that assumption might be wrong. Plus, they pull back the curtain on how financial aid and admissions are actually connected, what your Student Aid Index (SAI) really means, and why planning early can save you tens (or hundreds) of thousands. If you're feeling overwhelmed by college costs, this episode will help you think more strategically—and stay in the driver’s seat. What you’ll learn: How to choose between Parent PLUS and private student loansLoan forgiveness opportunities (especially for teachers)Why “we won’t qualify for aid” is often a mythThe truth about financial aid and admissions decisionsKey borrowing timelines and what to do right nowA major upcoming change to Parent PLUS loan limits (and who it impacts)🎧 Whether you’re a parent of a high schooler or already in the thick of college decisions, this episode is packed with practical insights to help you make smarter financial choices. 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 💸

    37 min
  7. The End of Student Loan “Blank Checks”: What Families Need to Know Now

    MAR 19

    The End of Student Loan “Blank Checks”: What Families Need to Know Now

    Federal student loans are changing—big time. From the elimination of the SAVE repayment plan to new caps on Parent PLUS loans, these updates could dramatically impact how families pay for college. In this episode, Matt sits down with College Aid Pro expert and Air Force veteran Mike Hunsberger to break down what’s changing, who it affects, and what families should be doing right now to prepare. Whether you’re currently in repayment, about to borrow, or years away from college, this is a must-listen conversation. 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

  8. MAR 12

    A Stanford Grad’s Advice on Elite Colleges, Admissions & College Fit

    What is it really like to attend one of the most selective colleges in the world? In this episode of Ol' College Try, host Peg Keough sits down with Mark Hernandez—a Stanford graduate, former high school English teacher of 25 years, and now a college essay consultant with a growing social media following. Mark shares his unexpected path to Stanford (including applying just four days before the deadline) and the difficult financial decision his family faced after he was admitted. Determined to reduce the burden on his dad, Mark created a plan to graduate from Stanford in just two years and two quarters—a strategy that even caught the attention of the university president. Peg and Mark also dive into: What Stanford’s campus culture is really like The surprising “work hard but pretend you’re not” academic mindset How students can strategically think about college costs Whether AP classes actually help students graduate early The type of student who truly thrives at selective universities Why finding the right college fit matters more than prestige Mark also reflects on how his own teachers shaped his career and how his experience in the classroom gives him a unique perspective on the college admissions process today. If your family is thinking about selective colleges—or just wants a clearer picture of what college success actually looks like—this conversation is packed with insight. 🎧 Plus, Mark shares the story behind his intro song: “Sweet Child O’ Mine” by Guns N’ Roses, a favorite across three generations of his family. 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 💸 Connect with Mark Hernandez! Instagram: https://www.instagram.com/englishwithmarkh/ TikTok: https://www.tiktok.com/@englishwithmarkh Website: https://englishwithmarkh.com/

    26 min
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4.3
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
    64
  • Rating
    Clean
  • Copyright
    © Matt and Peg's College Planning Podcast
  • Show Website
    Ol' College Try

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