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.

  1. Sep 24

    Q&A: Where to Start With College Planning, FAFSA & Understanding Your SAI

    Feeling overwhelmed by college planning and have no idea where to start? You're definitely not the only parent asking that question. In this month's Old College Try Q&A, Matt Carpenter and Peg Keough tackle three questions that get to the heart of paying for college: where families should start when everything feels overwhelming, whether you should still file the FAFSA when tuition is already covered by a scholarship, and what your Student Aid Index (SAI) actually means. The biggest theme? Start with the money before you fall in love with the college. Building a realistic four-year budget first can help families create a college list that works academically, personally, and financially—and potentially avoid difficult conversations and unnecessary debt later. Put your questions here: https://forms.gle/4fhtm9QpqHEHkhWh9 In this episode, we cover: 😵‍💫 What to do when college planning feels overwhelming and you don't know where to start 💰 Why creating your family's college budget should come before building the college list 🏦 What to include in your budget—from 529 savings and cash flow to student contributions and help from grandparents 🎓 Why families should understand how financial aid works before seriously touring colleges ❤️ How falling in love with a college before understanding affordability can create problems later 👨‍👩‍👧 Why parents should take an active role in the financial side of the college decision 🗣️ How setting financial expectations early can reduce stress between parents and students 🏫 Why academic and personal fit still matter—but should be considered alongside affordability 📋 Why families should still complete the FAFSA even if they think they won't qualify for need-based financial aid ☀️ What a Florida family's Bright Futures Scholarship question teaches us about FAFSA and merit aid 🏆 How merit scholarships can potentially help with costs beyond tuition, including room and board 🔢 What the Student Aid Index (SAI) actually represents—and what it doesn't tell you 💵 Why your SAI is not automatically the amount your family will pay for college 📊 How the same SAI can lead to completely different costs at different colleges 🏛️ Why a college's own financial aid policies can determine whether your family pays more than, less than, or close to your SAI 📄 Why some families may have both a FAFSA-based SAI and an institutional SAI from the CSS Profile ⚠️ Why seeing a high SAI doesn't necessarily mean your family is out of options for college discounts Key Takeaway: Don't start college planning by asking, “Where does my child want to go?” Start by understanding what your family can realistically afford. Build your budget, learn how financial aid works, understand your SAI, and then identify colleges that make sense for your student and your finances. Your SAI is an important starting point for determining need-based financial aid, but it isn't a college bill. Depending on the school, your family could pay more, less, or close to that number—which is why understanding how individual colleges award aid is so important. 🎵 Song of the Week: Linger — The Cranberries original + Lake Street Dive cover 🎧 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

  2. Sep 17

    FAFSA Deep Dive: Deadlines, FSA IDs & the Mistakes That Could Cost You Aid

    FAFSA season is officially here—but when should you actually submit it? Do you need to rush to file on October 1? And which mistakes could potentially cost your family financial aid? In this episode of Old College Try, Matt Carpenter and Peg Keough dive into all things FAFSA, walking families through what they should be doing now, how to approach the application, and some of the most common mistakes they see year after year. Before getting into the FAFSA, Matt and Peg also discuss college ROI and why families should look beyond rankings and prestige when deciding whether a college is worth the investment. They break down why the real question isn't simply where a school ranks—but what your student is likely to pay, how much they may need to borrow, and what their financial picture could look like after graduation. In this episode, we cover: 📊 Why college ROI should be part of your family's college decision—and why rankings don't tell the whole story 💰 How to think about college costs, potential borrowing, and expected earnings after graduation 📅 Why you don't necessarily need to submit the FAFSA the moment it opens ⏰ The difference between FAFSA opening day and a college's priority financial aid deadline 🚨 Why financial aid deadlines and admissions deadlines aren't always the same 🔑 What an FSA ID is and who in your family needs to create one 👯 What parents of twins and multiple college-bound students need to know about FSA IDs 👨‍👩‍👧 How FAFSA contributors work for married, divorced, separated, and remarried families 📋 Why CAP recommends completing the student section first and then inviting the parent contributor 🪪 What families should know about potential identity verification—and why your student should be nearby when completing the FAFSA 🏦 Why retirement accounts should not be reported as FAFSA investments 💵 How parent-owned 529 plans should be reported—and why putting them in the wrong place matters 🏠 Why the equity in your primary home should not be reported as an investment on the FAFSA 📈 Why knowing your expected Student Aid Index before filing can help you catch potential mistakes 💼 What business owners should know when they reach the business asset section of the FAFSA ⚠️ Why submitting accurate information and meeting each school's deadline can be far more important than racing to file on opening day Key Takeaway: Don't let FAFSA opening day create unnecessary panic. Get your FSA IDs ready, understand which contributors your student needs, check the priority financial aid deadlines for every college on the list, and know your expected SAI before you submit. Filing correctly matters more than simply filing first. The FAFSA may look straightforward, but seemingly small reporting mistakes—like including retirement accounts, reporting a 529 incorrectly, or including home equity—can change the financial picture colleges receive. Preparation now can make the process much smoother when it's time to hit submit. 🎵 Song of the Week: Buy Dirt by Jordan Davis feat. Luke Bryan 🎧 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. Sep 10

    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

  4. 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

  5. 5d ago

    CSS Profile Deep Dive: What Parents Need to Know Before They Submit

    The CSS Profile is officially live—but what exactly is it, who needs to complete it, and why can it have such a major impact on what your family pays for college? In this episode of Ol' College Try, Peg Keough goes solo for a deep dive into the CSS Profile, the second financial aid form required by roughly 250 colleges and universities. Unlike the FAFSA, the CSS Profile takes a much deeper look at your family's finances—and individual colleges can use that information differently when determining your eligibility for institutional financial aid. Peg breaks down the biggest differences between the FAFSA and CSS Profile, the financial situations families need to pay especially close attention to, and some of CAP's best practices for avoiding mistakes before you hit submit. Tell us more about you! Fill out this survey: Ol' College Try Survey In this episode, we cover: 📋 What the CSS Profile is—and why some colleges require both the FAFSA and CSS Profile 🏫 How to determine whether the colleges on your student's list require the CSS Profile 🔢 The difference between your federal SAI and the institutional SAI calculated by CSS Profile schools 🔍 Why the CSS Profile is more detailed and invasive than the FAFSA 👨‍👩‍👧 How the CSS Profile works differently for divorced and separated parents 👥 Why both the custodial and non-custodial parent may need to provide financial information 📝 When a non-custodial parent waiver may be appropriate 🏠 Why your primary home equity isn't included on the FAFSA—but may be considered by CSS Profile schools 💼 What business owners need to know about reporting the value of a family-owned business 👯 Why having multiple children in college can still benefit families at many CSS Profile schools 🔐 How to access the CSS Profile using your student's College Board credentials 💰 Why retirement accounts should not be included with your regular investments ⚠️ The CSS Profile question asking how much parents plan to contribute—and why families should answer it carefully 📣 How CAP approaches the Special Circumstances section and why Peg recommends thinking strategically about when to share changes in your financial situation 🎓 How parent-owned and grandparent-owned 529 plans should be treated differently 📄 Why some CSS Profile questions are required while others may be optional 🧾 Why families should be prepared to provide tax returns, W-2s, and other financial documents after submitting 💡 The three rules Peg recommends remembering when completing financial aid forms: be honest, don't overshare, and don't overestimate Key Takeaway: The CSS Profile isn't just a longer FAFSA. It can look at parts of your financial life that the FAFSA doesn't—including home equity, business value, and, in many divorced families, the finances of both biological parents. At the same time, it can create important planning opportunities, particularly for families with multiple children in college or unique financial circumstances. Before submitting, understand how the schools on your student's list use the CSS Profile, know your expected SAI, pay close attention to each school's priority financial aid deadline, and make sure you're reporting your family's information accurately without unnecessarily overestimating or oversharing. 🎵 Song of the Week: Allison Road by Gin Blossoms 🎧 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 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

  7. 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

  8. 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

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.

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