

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

May 8, 2025 • 43min
Student Loan Defaults, Post-Decision Day Aid Boosts & College Cost Strategies Every Parent Needs to Know
Are student loan payments coming back? What happens if your child—or you—are in default? In this timely episode of the College! podcast, Matt and Peg break down the urgent changes to federal student loan repayments, what to do right now if you’ve fallen behind, and how it can impact everything from your credit score to your job search.Plus, if your high school senior just committed to college on May 1, don’t close the door just yet—many colleges are offering bigger financial aid packages even after the deadline. Learn how to appeal, renegotiate, and make last-minute money moves that could save your family thousands.We also unpack a powerful New York Times piece on how colleges use private equity firms to maximize what you’ll pay—and what you can do about it. And stay tuned for big news on the push for more accountability in higher education and what it means for future affordability.This is a must-listen for every parent navigating the college process—because being informed isn’t just power, it’s savings.👉 Subscribe and share with families navigating college planning!Learn more about what we do at College Aid Pro! Create a Free MyCAP account here to start personalizing your college planning journey! Follow Us to hear exactly when new episodes drop! Chapters: Intro (0:00) Navigating Student Loan Repayment Challenges (05:08) Understanding College Decision Dynamics (08:58) Maximizing Financial Aid Opportunities (13:04)The Business of Higher Education and Marketing Strategies (16:43) The Accountability Crisis in Higher Education (24:53) Government Oversight and College Responsibilities (28:37) The Role of Financial Aid and College Funding (33:55) Proposed Cuts to Educational Programs (39:45) Empowering Parents and Students for Change (45:50)

Apr 30, 2025 • 40min
Student Loan Shakeup: What Borrowers & Families Need to Know About the New & Proposed Changes
🚨 Student Loan Shakeup Alert!Federal student loan repayment is back—and that’s just the beginning. In this episode of College!, Matt Carpenter and Peg Keough unpack urgent updates affecting millions of borrowers, including those in default facing wage garnishment starting May 5th. They also explore sweeping proposals from the House that could redefine the college funding landscape by eliminating subsidized loans, Parent PLUS loans, and graduate PLUS loans, while introducing new rules for Pell Grants and income-driven repayment plans. With a focus on borrower accountability and long-overdue college accountability, this episode is a must-listen for families, students, and financial planners navigating the evolving world of higher ed funding.👉 Subscribe and share with families navigating college planning!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/

Apr 17, 2025 • 42min
College Planning From the Mom Side: Real Talk on Costs, Choices & Second Chances
In this episode of The College Podcast, Peg Keough is joined by fellow College Aid Pro team members—and fellow moms—Cathy Portele and Ann-Marie Sanderson. Together, they dive into their personal experiences guiding their kids through the college admissions journey. From learning financial lessons the hard way, to setting clear expectations the second time around, this candid conversation offers invaluable insights for families navigating the process.Discover:The emotional and financial lessons learned from sending their first kids to collegeHow they're approaching the journey differently with their younger childrenThe power of setting boundaries, being transparent, and allowing kids to leadThe impact of military benefits, homeschooling, and music scholarships on college decisionsWhether you're a parent of a middle schooler or a senior deep in applications, this episode will resonate, inspire, and help you feel less alone in this transformative season.👉 Subscribe and share with families navigating college planning!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/ChaptersIntroduction and Recent Developments in Education (00:00) Navigating the College Process: Insights from Three Moms (03:51) The Journey of College Selection: Personal Experiences (07:08) Financial Planning for College: Setting Boundaries and Expectations (09:58) Understanding Scholarships and Financial Aid (13:06) The Impact of Individual Choices on College Outcomes (16:04)Lessons Learned: Reflections on the College Experience (19:00) Final Thoughts and Advice for Parents (22:04) Conclusion and Future Considerations (24:57) Navigating Academic Expectations (27:28) Understanding College Financial Planning (29:21)The Importance of Early Preparation (33:19) Modeling Behavior for Future Success (37:29) Key Takeaways for Parents (40:30) Navigating the College Journey (46:44) Reflections and Lessons Learned (47:25)

Apr 6, 2025 • 27min
Get to Know Our CEO & Our Plan to Fix the U.S. College System Part 2
In Part 2 of our conversation with College Aid Pro CEO Kevin Degnan, we go deep on why the U.S. college system is broken—and how we can fix it. With $1.8 trillion in student loan debt and skyrocketing tuition, Degs and Matt break down how we got here and the bold steps needed to create real accountability in higher education.From federal student loan reform to holding colleges financially accountable for outcomes, this episode offers clear, practical solutions to fix a system that’s failing too many families. If you're a parent, student, policymaker, or educator, this is essential listening for anyone who wants to make college more affordable and transparent.👉 Subscribe and share with families navigating college planning!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/ChaptersIntroduction to Kevin Degnan (00:00) The Historical Context of Student Loans (01:27) The Role of Government in College Financing (07:02) The Need for Accountability in Higher Education (10:05) Proposed Solutions for Reform (13:35) Ensuring Accessibility in Education (1 8:33)

Apr 3, 2025 • 30min
Get to Know Our CEO & Our Plan to Fix the U.S. College System Part 1
In Part 1 of this special two-part episode, Matt sits down with College Aid Pro CEO Kevin “Degs” Degnan to unpack the personal journey that shaped his mission to reinvent how families pay for college. From growing up as one of eight kids in Massachusetts to facing the hard truths of the college application process, Degs shares the setbacks and pivots that ultimately led him from Stonehill College to the Peace Corps in Peru, and eventually to earning his MBA and building a remarkable career in finance and business management. This is a candid look at what happens when your dream school says no—and how that moment can fuel a lifetime of purpose. If you’re navigating college admissions, financial aid, or wondering how rejection shapes resilience, this episode is for you!👉 Subscribe and share with families navigating college planning!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/ChaptersMeet Our CEO (00:00) Growing Up in a Big Family (02:53) College Application Journey and Rejections (05:20) Advice for College Applicants (08:16) Transitioning to the Peace Corps (10:35) Experiences in the Peace Corps (13:27) Pursuing an MBA and Career Reflections (15:59) Working with ExxonMobil in Iraq (18:33) Career Path and Investment Banking (21:12) The Evolution of College Aid Pro (24:09) Understanding the College Funding Crisis (26:44) The Historical Context of Student Loans (29:10)

Mar 27, 2025 • 46min
What Parents Need to Know About FAFSA Chaos, Loan Forgiveness & College Costs in 2025
In this timely episode, Matt Carpenter and Peg Keough break down the latest chaos in the world of student loans and college financial planning. With recent announcements about the Department of Education’s restructuring—including the controversial shift of the Office of Federal Student Aid under the SBA—families across the country are left wondering what this means for their financial aid, loan forgiveness programs, and college affordability.Matt and Peg discuss the real-time impact on current borrowers, the challenges of FAFSA system failures, and offer crucial insights into why keeping meticulous loan records is more important than ever. They also dive into bold predictions around the potential elimination of Parent PLUS Loans, the long-term effects on college pricing, and how families can prepare smarter now.Whether you have a senior choosing between colleges or a younger student on the path to higher ed, this episode offers powerful advice, action items, and a dose of perspective every family needs.🔑 Topics Covered:Loan forgiveness program freezesFAFSA glitches & system breakdownsImpact of shifting Federal Student Aid to the SBAWhy PLUS Loans may disappearAction steps for the Class of 2025 and beyondSetting realistic college expectations with your childThe case for trade schools and alternate education paths👉 Subscribe and share with families navigating college planning!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/ChaptersIntroduction (00:00)Department of Education Changes (03:11)Current Borrowers and Loan Servicing Challenges (05:59)FAFSA Issues and Their Impact (08:56) The Importance of FAFSA for College Access (12:01)Predictions on Student Loan Changes (17:53)The Impact of Student Loans on Families (24:01)Setting Expectations for College Costs (28:24)Navigating College Choices and Financial Aid (31:56)The Future of College Affordability (38:33)Taking Control of College Financing (46:57)

Mar 20, 2025 • 45min
College Costs, Harvard’s Tuition Shift, and What Could Go Right?
This week on College, Matt Carpenter and Peg Keough dive into major changes shaking up higher education, including Harvard’s latest tuition policy update and a proposed tax hike on university endowments. They also discuss the Department of Education layoffs, FAFSA glitches, and what these changes mean for families navigating the college affordability maze. Plus, they challenge the narrative around “no-loan” schools and share practical insights on how families can take control of their college planning process. Tune in for a candid, insightful discussion—and a dose of optimism about what could go right!🎧 Listen now and don’t forget to share!http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/Chapters: Mindset Matters: Overcoming Catastrophizing (00:00)Department of Education Layoffs: Impacts and Reactions (05:01) FAFSA Glitches: Coincidence or Consequence? (09:35) Accountability in Higher Education: Oversight Challenges (13:43) Harvard's Tuition Changes: A Closer Look (19:25) Understanding Financial Aid at Elite Schools (22:48) The Unique Formula of Harvard's Financial Aid (25:06) The Importance of Individual Financial Situations (27:49) Navigating College Affordability and Financial Aid (31:03) The Misconception of 'No Loan' Policies (33:29) Potential Changes in Endowment Taxation (37:11) Optimism for Future Changes in Education Funding (41:00)

Mar 13, 2025 • 41min
🎓 The Future of College Costs: Financial Aid, Loans & What Families Should Expect in 2025
📢 Episode Description:In this episode of College!, Matt Carpenter and Peg Keough break down the latest college financial aid changes, student loan policies, and campus controversies that could impact students and families in 2025. From FAFSA updates and federal loan cutbacks to hiring freezes at major universities, we cover what you need to know to make informed college decisions. Plus, we discuss why Columbia University is losing $400 million in federal funding due to campus protests—and what this means for other institutions.🔍 Key Topics Covered:✅ FAFSA changes and how they affect financial aid eligibility✅ Student loan forgiveness updates and repayment plan changes✅ College hiring freezes and their impact on students✅ Why some universities are losing federal funding over campus protests✅ Smart financial planning tips for families navigating college costsIf you’re a parent, student, or educator looking for expert insights on paying for college, student loans, and financial aid in 2024, this episode is a must-listen. Don’t forget to follow, subscribe, and share for more college planning insights! 🎧💡 http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comhttps://www.instagram.com/capcollegepod/ChaptersIntroduction to College Conversations (00:00) March Madness and Personal Celebrations (03:04)Changes in Higher Education Landscape (05:48) Impact of Department of Education Changes (08:23) Financial Aid and Loan Programs (11:27) Navigating Student Loans and Credit (14:09) Hiring Freezes in Higher Education (16:53) 1Anti-Semitism and Federal Funding Issues (9:23) Free Speech vs. Hate Speech on College Campuses (24:14) The Role of Universities in Promoting Safety and Diversity (26:50) Navigating Controversial Topics in Academia (29:56) Accountability and Consequences for Universities (31:50) Financial Planning for College: A Necessity (v) Appealing Financial Aid Offers: Strategies for Success (40:11) #CollegeCosts #FAFSA #StudentLoans #FinancialAid #HigherEd #CampusNews

Mar 6, 2025 • 30min
The Future of College Funding: Student Loans, Policy Shifts & What Parents Must Know
With major changes happening in higher education policy, student loan repayments, and financial aid structures, what do parents and students need to know right now? In this episode of The College! Podcast, hosts Matt Carpenter and Peg Keough break down the latest developments, including:✅ The impact of Linda McMahon's appointment as Secretary of Education✅ The privatization of student and parent loans – and how it affects your borrowing options✅ What FAFSA changes and Department of Education layoffs mean for families✅ State-based loan programs that could save you thousands in interest✅ Actionable steps to prepare for rising college costsWith student loan forgiveness under fire and repayment plans being halted, it's more important than ever to have a strategy. Don't wait until the tuition bill arrives—learn how to take control of your college funding plan now!🔗 Subscribe and follow for expert insights on navigating college costs without breaking the bank.ChaptersMardi Gras and Family Adventures (00:00) Department of Education Changes (03:02) Impact of Staff Reductions (05:33)Navigating the Department of Education(08:27)Linda McMahon's Appointment (11:10)Privatization of Student Loans (13:42)Understanding Loan Options (16:24)Planning for College Costs (19:04)Transparency in Borrowing (21:57)'http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.com#CollegePlanning #StudentLoans #FAFSA #HigherEd #CollegeFunding #FinancialAid #EducationPolicy

Feb 27, 2025 • 37min
Navigating DOE Policy Changes: How New Financial Aid & Student Loan Shifts Impact Families
In this week's podcast, Matt and Peg discuss the evolving landscape of student loans, federal funding, and the implications of recent educational policies. They emphasize the importance of maintaining a positive mindset amidst uncertainty, understanding the nuances of federal loan programs, and the critical role of Pell Grants in supporting low-income families. The discussion also touches on the impact of the Dear Colleague letter and the need for families to be proactive in navigating their financial aid options.Chapters Introduction (00:00) Mindset Amidst Changing Educational Policies (02:04) Understanding Federal Loan Changes (06:05) The Impact of the Dear Colleague Letter (11:58) Navigating Federal Direct Student Loans (18:01) The Importance of Pell Grants (23:53) Conclusion and Key Takeaways (29:56)http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.com


