

Ol' College Try
Matt and Peg's College Planning Podcast
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.
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.
Episodes
Mentioned books

Jan 29, 2026 • 36min
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 outcomesWhy relationships, networking, and adaptability may matter more than everIf 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 💸

Jan 22, 2026 • 34min
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 💸

Jan 15, 2026 • 40min
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 💸

Jan 8, 2026 • 31min
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 offerWhy loans and work-study can make a college look cheaper than it actually isCommon red flags on award letters that families often missWhat underclassmen parents should be thinking about now to avoid surprises laterWhether 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 💸

Jan 1, 2026 • 20min
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 💸

Dec 25, 2025 • 28min
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 aidWhether retirement accounts affect FAFSA and the CSS ProfileWhen and why it’s worth appealing a financial aid offer (even at state schools)How colleges think about full-pay families versus discounted offersWhen families should start working with College Aid Pro—and why earlier is betterPlus, 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 💸

Dec 18, 2025 • 37min
College Rejections: What to Do If Your Child Doesn’t Get Into Their Dream School
As college acceptance letters roll in, emotions are running high for families. Experts break down the differences between Early Decision, Early Action, and what to do when faced with rejections or deferrals. They stress the importance of a supportive mindset for students and parents alike. Personal stories reveal how setbacks can lead to unexpected opportunities. Ultimately, the message is clear: where you go to college doesn't define who you become, and resilience is key during this emotional journey.

6 snips
Dec 11, 2025 • 33min
How to Appeal Early Decision Financial Aid (Without Breaking Your ED Agreement)
Navigating Early Decision financial aid can be tricky, especially with binding contracts. Explore how to appeal these offers without breaking agreements, and learn why 'negotiate' can derail your appeal. Discover practical tips for assessing aid fairness and hear real-life success stories from families. The hosts discuss the importance of using the right language in appeals and making clear monetary requests. Plus, take the Net Price Calculator Challenge for a chance to win $100 if you uncover discrepancies in college cost estimates!

Dec 4, 2025 • 42min
Demonstrated Interest with Mark Stucker: What It Is and How It Impacts College Admissions
Mark Stucker, producer of the Your College Bound Kid podcast and admissions expert, dives into the crucial concept of demonstrated interest in college admissions. He explains how colleges assess applicants' likelihood of enrollment and highlights key ways students can show genuine interest, such as campus visits, engaging essays, and email communication. Mark breaks down myths about demonstrated interest, discusses its impact on admissions strategies, and offers practical tips to help students stand out in their college applications.

Nov 27, 2025 • 34min
CAP's Thanksgiving Special: Financial Aid Q&A for Stressed-Out Parents
It’s a special Thanksgiving mailbag episode of The Ol’ College Try podcast! Matt Carpenter and Peg Keough go in totally unprepared and answer your toughest, most common college-planning questions on the fly. They tackle what happens when you have two, three, or even more kids in college at once (and why some schools give a break while others don’t), how FAFSA and CSS Profile work for divorced or separated families, and the truth about your Student Aid Index (SAI)—including why it’s not what you’ll automatically pay.You’ll also learn how rental or investment properties are treated on the FAFSA vs. CSS Profile, why most colleges’ net price calculators are outdated (and how to double-check affordability the smart way), and whether appealing a financial aid offer can backfire (spoiler: it won’t—if you do it right).Perfect for parents trying to make sense of financial aid rules, tuition reality, and how to advocate for more aid without hurting admissions. Happy Thanksgiving—and don’t forget to send your next burning question for a future mailbag!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


