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. 6d ago

    Homeschool to College: What Parents Should Know About Admissions, Transcripts & Scholarships

    Can homeschooled students get into competitive colleges? Are they eligible for merit scholarships? And what exactly does a homeschool parent need to do when it comes time to apply? In this episode of Old College Try, Peg Keough sits down with Caitlyn Obolsky, a homeschooling mom of six who recently sent her two oldest daughters off to UC Berkeley and UC Davis. Caitlyn shares what she's learned from more than a decade of homeschooling—and what parents need to know if college is part of their student's plan. From building a high school curriculum and navigating dual enrollment to creating transcripts, acting as your student's school counselor, finding social opportunities, and pursuing merit scholarships, Caitlyn breaks down the realities of taking a homeschooled student through the college admissions process. In this episode, we cover: 🏠 The different ways families can homeschool, including independent homeschooling, co-ops, hybrid programs, and pod schooling 🎓 Whether homeschooled students can compete for admission at selective colleges and universities 📚 How Caitlyn built completely different high school experiences around each daughter's strengths, interests, and goals 🧮 Why outsourcing certain courses, including math, science, APs, and dual enrollment, can help create a rigorous academic record 📝 Why homeschool parents need to realize they're also their student's school counselor 📄 How to create an official homeschool transcript, school profile, grading scale, and course descriptions for college applications ⏰ Why you should start building your student's transcript early instead of waiting until junior or senior year 📖 Why keeping course descriptions—and even a running book list—can save families a major headache when application season arrives 💰 Why homeschooled students can absolutely qualify for substantial merit scholarships 🎉 How Caitlyn's daughters received merit offers—including one that grew from $34,000 per year to $54,000 per year 🏫 Why relying entirely on community college and transferring later could affect access to freshman merit scholarships ⚾ How extracurricular activities, sports, and social opportunities can work differently for homeschooled students 🎯 How the flexibility of homeschooling can give students unique opportunities to build activities and experiences around their interests Key Takeaway: Homeschooling doesn't have to limit a student's college options—but parents need to be intentional. Keep detailed records from the beginning, understand that you'll likely serve as both parent and school counselor, build an academically appropriate curriculum, and make sure your student has meaningful activities outside the classroom. There isn't one “perfect” homeschool curriculum that guarantees admission, but homeschooled students can absolutely be competitive college applicants. And if scholarships are part of your college strategy, don't assume homeschooling takes merit aid off the table. Caitlyn's experience shows that homeschooled students can receive significant merit offers—but families should understand the difference between applying as a first-year student and transferring later. 🎵 Song of the Week: Unconditional I (Lookout Kid) by Arcade Fire 🎧 Listen to our full podcast playlist here: https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE → Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet → https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15 → https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 📱 Follow Caitlyn Oblosky: Instagram: https://www.instagram.com/ddchomeschool/ 🌐 Learn more about College Aid Pro: https://collegeaidpro.com

  2. Sep 3

    What Really Happens After You Submit Your College Application? An Insider’s Look at Admissions & Financial Aid

    What actually happens after your student hits “submit” on their college application? And why can two equally qualified students receive completely different admissions—and financial aid—outcomes? In this episode of Old College Try, Peg Keough is joined by College Aid Pro expert Christina Lopez, former Dean of Enrollment Management at Barnard College with more than 20 years of experience in higher education, including NYU. Together, they take families behind the scenes of admissions and financial aid to explain how colleges actually build an incoming class—and why there’s so much happening that families never see. In this episode, we cover: 🎓 What really happens after your student submits their college application 👀 Who actually reads applications—and why admissions decisions are still largely made by real people 📚 Why the high school transcript remains one of the most important parts of the application ✍️ How a great college essay can help a student stand out—and why it can't make up for weaknesses everywhere else 🎯 What “institutional priorities” are and how they can influence who gets admitted each year 🏫 Why a rejection doesn't necessarily mean your student wasn't qualified 📊 How colleges use application numbers, admit rates, and yield to build an incoming class 💰 How financial aid and merit scholarships fit into a college's larger enrollment strategy 📉 What the “enrollment cliff” could mean for colleges—and potentially for families 🔥 What happened at Syracuse and why enrollment shortfalls can create major financial challenges for colleges 💵 Why families should build a four-year college budget before finalizing the college list 🔍 Why sticker price doesn't tell you what a college will actually cost your family 📋 How colleges use need-based versus merit-based financial aid differently 🧮 Why Net Price Calculators can be helpful—but shouldn't be your only source for estimating college costs 💡 Why your admissions strategy and financial aid strategy need to work together Key Takeaway: College admissions isn't simply a ranking of the “best” students. Colleges are building a class based on their own priorities, enrollment goals, financial needs, and the students they believe fit their community that particular year. Families can't control everything happening behind the scenes—but they can control building a smart, balanced college list that works academically, personally, and financially. And when it comes to affordability, don't wait until acceptance letters arrive to figure out what you can pay. Start with a four-year budget, understand how each college awards financial aid, and build your admissions strategy around schools that have a realistic path to your family's number. 🎵 Song of the Week: 9 to 5 by Dolly Parton 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  3. Aug 27

    Q&A: Student Loans, Credit Scores, College Budgets & SAI Strategies

    What’s the difference between subsidized and unsubsidized student loans? What credit score do you actually need to borrow for college? And can those ads promising to slash your Student Aid Index by 50% really be trusted? In this month's Old College Try Q&A, Matt Carpenter and Peg Keough tackle some of the biggest questions families are asking about paying for college. From federal student loans and credit scores to building a realistic four-year budget, navigating financial aid after separation or divorce, and helping an undecided student find the right college fit, this episode covers a little bit of everything. In this episode, we cover: 💰 The difference between subsidized and unsubsidized Federal Direct Student Loans 🎓 Why CAP recommends families consider taking the Federal Direct Student Loan—even if they don't immediately need it 📈 What counts as a "good" credit score when shopping for college loans 🏦 How your credit can affect your private, state, and Parent PLUS Loan options 💵 The different pieces that should go into your family's four-year college budget 👵 How to factor grandparents and other family contributions into your college plan 👨‍👩‍👧 What separated and divorced parents need to know about financial aid 🎯 How to help a student who's stressed because they don't know what they want to major in 🏫 Why being undecided isn't necessarily a disadvantage—and how the right college can help students explore their options ⚠️ Whether companies promising to reduce your SAI by 50% are legitimate 🔍 Why lowering your SAI doesn't automatically mean you'll pay less for college 💡 The red flags to watch for before making major financial moves solely to increase financial aid eligibility Key Takeaway: There is no one-size-fits-all strategy for paying for college. Your borrowing options, financial aid eligibility, budget, and even the colleges that make financial sense depend on your family's individual situation. Build the budget first, understand your options, and always look beyond flashy promises before making a major financial decision. 🎵 Song of the Week: Romeo and Juliet by Dire Straits 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  4. Aug 20

    FAFSA 2027–28: Why Every Family Should File & What to Do Before October 1

    FAFSA season is almost here—and even if you think your family won't qualify for financial aid, you should still file. In this episode of Old College Try, Matt Carpenter and Peg Keough kick off the 2027–28 FAFSA season by breaking down what the FAFSA actually does, why they recommend every family submit it, and what parents of Class of 2027 students should be doing now to prepare. They also cover new identity verification requirements, financial aid deadlines, FSA IDs, and some of the biggest FAFSA mistakes that could cost families money. In this episode, we cover: 📋 What the FAFSA is and how colleges use it to determine financial aid eligibility 💰 Why families with higher incomes may still qualify for need-based financial aid 🎓 Why some colleges require the FAFSA for merit scholarships 🏦 How filing the FAFSA gives students access to Federal Direct Student Loans ⚠️ Why skipping the FAFSA freshman year could impact your ability to receive institutional aid later ✅ Why students applying for financial aid should check "yes" on their college applications 🪪 The new FAFSA identity verification process and what ID students should have ready 📅 Why October 1 is the FAFSA opening date—not necessarily your deadline ⏰ How priority financial aid deadlines work and why missing one could mean receiving less aid 🔑 What students and parents can do right now by creating their FSA IDs 👨‍👩‍👧 What divorced and separated families need to know about determining the FAFSA custodial parent 💵 Why families need to understand the four-year cost of college before applications are submitted Key Takeaway: Don't skip the FAFSA because you assume you make too much money, and don't wait until the last minute to start preparing. Create your FSA IDs now, understand each school's financial aid requirements and deadlines, and know what those colleges are projected to cost your family over all four years. 🎵 Song of the Week: Peg by Steely Dan 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  5. Aug 13

    “Free Tuition” Isn’t Always Free: What Families Need to Know About College Cost Promises

    "Free tuition." "No-loan school." "Families making under $200,000 pay no more than $20,000." These college affordability promises sound incredible—but what do they actually mean for your family? In this episode of Old College Try, Matt Carpenter and Peg Keough break down the push for greater transparency in higher education, including the College Transparency Act and its goal of helping families understand both the true cost of college and the outcomes they can expect. They also unpack new affordability initiatives from schools like Davidson and Boston University—and explain why families need to read beyond the headline before assuming a college will be affordable. In this episode, we cover: 🎓 What the College Transparency Act is and why greater transparency matters for families 💰 Why families should look at the four-year cost of college, not just the freshman-year price tag 📊 How expected career outcomes and college costs should factor into your decision 🏫 What "free tuition" programs may—and may not—actually cover 💵 The difference between tuition, fees, room and board, and the total cost of attendance 🔍 Why income limits aren't the only factor determining whether your family qualifies for these programs 🏦 How your assets can impact eligibility even when your income falls below a school's advertised threshold 📣 Why schools like Davidson and Boston University are introducing new affordability programs ⚠️ What a "no-loan school" actually means—and why your student can still borrow federal loans 🧠 Why families should always verify what a college will actually cost them before getting emotionally attached Key Takeaway: Don't make a college decision based on a headline. "Free tuition," "no loans," and income-based affordability guarantees can be valuable, but the details matter. Look at your family's personalized cost, understand what's actually included, and think about the entire four-year investment before deciding whether a school truly fits your budget. 🎵 Song of the Week: Mrs. Potter's Lullaby by Counting Crows 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  6. Aug 6

    AP vs. Dual Enrollment vs. Honors: Which Classes Actually Matter for College?

    Should your student take AP classes, dual enrollment, or honors courses? Will they improve admissions chances? And can they actually save you money on college? In this episode, Peg Keough is joined by College Aid Pro admissions expert Joe Korfmacher to break down the biggest misconceptions surrounding advanced high school coursework. They explain how colleges evaluate course rigor, when AP or dual enrollment credits actually transfer, and why families shouldn't choose classes based solely on the hope of graduating early or saving tuition. In this episode, we cover: 🎓 The differences between AP, dual enrollment, and honors classes 📚 How admissions offices evaluate course rigor in the context of your high school 📝 Whether earning a B in an AP class is better than an A in a less challenging course 💰 Can AP and dual enrollment classes actually reduce the cost of college? 🏫 Why every college has different policies for accepting AP and dual enrollment credit 📊 How weighted GPAs work—and why comparing GPAs across schools can be misleading 🎯 How students should choose advanced courses based on their goals, strengths, and interests 💡 Common mistakes families make when planning high school coursework 💵 Ways to avoid unnecessary AP score reporting and testing costs during the admissions process 👨‍👩‍👧 Why students should challenge themselves without sacrificing their well-being Key Takeaway: The goal isn't to collect the most APs or dual enrollment credits—it's to build a thoughtful academic schedule that demonstrates curiosity, appropriate rigor, and genuine interest. Colleges review students within the context of their high school, so choosing courses with purpose will always matter more than simply loading up on advanced classes. 🎵 Song of the Week: Bottle Rockets by Scotty McCreery 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  7. Jul 30

    Q&A: Parent PLUS Loans, Multiple Kids in College & Borrowing Without Regret

    How do you choose the right student loan? What happens if you have two kids in college at the same time? And are outside scholarships really worth it if colleges reduce your financial aid?In this solo Q&A episode, Matt Carpenter answers some of the biggest questions families are asking right now about borrowing, financial aid, and paying for college. From understanding the new Parent PLUS Loan limits to comparing private, state, and federal loan options, Matt breaks down practical strategies to help families make informed financial decisions.In this episode, we cover:💰 How to determine the best loan option for your family's situation🏦 The differences between federal, state, and private student loans📊 When Parent PLUS Loans make sense—and when private lenders may offer better rates👨‍👩‍👧‍👦 How to handle paying for multiple children in college at the same time🎓 Why families shouldn't rely on athletic or merit scholarships as their college funding plan⚠️ What scholarship displacement is and how to appeal if your college reduces your financial aid📝 Common FAFSA questions and how to avoid costly mistakes📚 Where to find current federal student loan interest rates and repayment options💳 How Parent PLUS Loans are disbursed throughout the academic year🧠 Why taking action early reduces stress and leads to better financial decisionsKey Takeaway: Every family's borrowing strategy should be different. The best loan isn't determined by the college your student attends—it's determined by your financial situation, credit profile, and long-term repayment goals. The earlier you compare your options and build a plan, the more flexibility you'll have.🎵 Song of the Week: Golden Age by Chris Staples🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0📚 Resources & Links:🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0📄 Download the Student Loan Fact Sheet→ https://hubs.li/Q04cmnWD0💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/📱 Follow College Aid Pro:Facebook: https://www.facebook.com/CollegeAidProInstagram: https://www.instagram.com/collegeaidproTikTok: https://www.tiktok.com/@collegeaidproLinkedIn: https://www.linkedin.com/company/college-aid-pro🌐 Learn more about College Aid Pro:https://collegeaidpro.com

  8. Jul 23

    Freshman Year Survival Guide: Homesickness, Making Friends & Thriving in College (Part 2)

    The first few weeks of college can be exciting...and overwhelming. In Part 2 of Peg Keough's conversation with life coach Suzanne Hanna, they dive into what really happens after move-in day. From homesickness and making friends to building healthy routines and succeeding academically, this episode is packed with practical advice to help students navigate one of life's biggest transitions and help parents know how to support them along the way. In this episode, we cover: 🎒 Why the transition from high school to college feels overwhelming for so many students ❤️ Why homesickness is a sign of love, not weakness 🤝 How to make friends during the first few weeks on campus (even if you're shy) 📱 Why your cell phone can become your biggest obstacle to building community 🧠 Practical ways to get comfortable being uncomfortable before college even starts 📚 The biggest academic adjustment freshmen face and why high school study habits often stop working 📝 A simple study routine that helps information actually stick ⏰ How to create structure when no one is managing your schedule anymore 👩‍🏫 Why office hours may be one of the most underused resources on campus 🌱 How students can build independence while knowing it's okay to ask for help Key Takeaway: College isn't just an academic transition—it's an emotional one. The students who thrive aren't necessarily the smartest; they're the ones who embrace discomfort, build meaningful relationships, create healthy routines, and remember that everyone around them is navigating the same transition. 🎵 Song of the Week: Saturn by SZA 🎧 Listen to our full podcast playlist here:https://hubs.li/Q03kvxZn0 📚 Resources & Links 🔢 Understand your college costs for FREE→ Create your MyCAP Account: https://hubs.li/Q03PTJ_x0 → Student Loan Fact Sheet: https://hubs.li/Q04cmnWD0 💰 Get 15% OFF sitewide with code COLLEGETRY15→ https://shop.collegeaidpro.com/ 📱 Follow College Aid Pro: Facebook: https://www.facebook.com/CollegeAidPro Instagram: https://www.instagram.com/collegeaidpro TikTok: https://www.tiktok.com/@collegeaidpro LinkedIn: https://www.linkedin.com/company/college-aid-pro 📱 Follow Suzanne Hanna: Website: ⁠https://suzannehannacoaching.com/⁠Instagram: ⁠https://www.instagram.com/suzannehannacoaching⁠YouTube: ⁠https://www.youtube.com/@SuzanneHannaCoaching 🌐 Learn more about College Aid Pro:https://collegeaidpro.com

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4.3
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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
    82
  • Rating
    Clean
  • Copyright
    © Matt and Peg's College Planning Podcast
  • Show Website
    Ol' College Try