

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

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

Feb 20, 2025 • 36min
Understanding Recent & Potential Policy Changes in Education
In this episode, Matt Carpenter and Peg Keough discuss the current landscape of college funding, including the implications of recent education policies, the Dear Colleague letter, and the impact of potential changes to financial aid and student loans. They explore the challenges families face in navigating these changes and provide key takeaways for students and parents to better prepare for the future of college funding.Chapters: Implications of the Dear Colleague Letter (00:00) The Future of College Admissions and Financial Aid (08:10) The Broken System of Higher Education (09:05) Communication Challenges in Education Policy (12:50) Concerns Over Financial Aid and Scholarships (14:53) The Future of Student Loans (19:27 ) The Impact of PLUS Loans on College Affordability (23:59) Federal Funding and Institutional Responses (29:20) Key Takeaways for Students and Parents (32:13)http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comJoin our Facebook Group to Continue Getting Updates: facebook.com/groups/collegeaidprospayingforcollegeandscholarships

Feb 12, 2025 • 39min
Department of Education Federal Funding Freeze: Latest Updates & Implications
In this conversation, Matt Carpenter and Peg Keough discuss the recent announcement regarding the Department of Education and its implications for higher education funding and student loans. They explore the potential changes to financial aid, the role of Parent PLUS loans, and the importance of oversight in education funding. The discussion emphasizes the need for families to take accountability in navigating the college funding process and the impact of political decisions on education policy.Chapters:Introduction to the Podcast and Hosts (00:00)The Department of Education Bill: An Overview (01:36)Understanding the Implications of the Bill (03:29)Navigating Change: Perspectives on Education Policy (05:22)The Role of Federal Student Loans (08:10)Concerns Over Oversight and Support (10:45)The Debate on Parent PLUS Loans (13:34)The Future of Student Loans and Financial Aid (18:41)The Role of Private Sector in Education Funding (26:11)Taking Accountability in the College Process (31:43)http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.comJoin our Facebook Group to Continue Getting Updates:facebook.com/groups/collegeaidprospayingforcollegeandscholarships

Feb 12, 2025 • 30min
Matt's Story | Navigating the Complexities of College Financial Aid and School Selection
Join Matt Carpenter and Peg Keough as they explore the complexities of the college experience, focusing on financial aid trends, personal college journeys, and the emotional aspects of navigating higher education. They discuss the assumptions made by colleges regarding family finances, the importance of open communication about money, and how personal experiences shape one's college choices and future. The dialogue emphasizes the need for families to engage in honest discussions about financial realities and the impact of college on personal growth and relationships.Chapters Introduction and Overview of College Experience (00:00) Financial Aid Challenges and Trends (01:10) Personal College Journey and Family Influence (06:13) Navigating College Admissions and Financial Aid (12:13) Reflections on College Impact and Personal Growth (17:59) Lessons Learned and Advice for Future Students (25:12)http://www.collegeaidpro.comhttp://www.mycap.collegeaidpro.com


