Episodios
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The shocking murder of UnitedHealthcare’s CEO is a tragic story that highlights deeper issues within the health insurance industry — wealth, greed, inequality, and power dynamics — and raises important questions about the prioritization of profits over patient care. We’re taking a closer look at the broader implications of this event and its ties to the systemic challenges healthcare professionals already know too well. Sim Terwilliger, CFP®, CSLP®, joins us and shares a personal connection to the story. We explore the emotions and frustrations it brings up, especially for those working in a system often criticized for putting profit before people.
Key moments:
(04:35) Unpacking the growing anger toward health insurance companies
(10:36) Insurance companies overriding physicians leads to worse outcomes for patients
(13:00) A recap of what happened, the manifesto, and the controversial sympathy for the alleged shooter’s motives
(21:07) Fear and frustration leave many wondering if change in healthcare is even possibleLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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The PSLF buyback program could be the key to reaching forgiveness faster, but there’s a catch. You must use exact language in your reconsideration request, or it won’t count. Without it, your request might be dismissed as just an inquiry — seriously. We break down everything you need to know about PSLF buyback, including the steps to get your application right the first time, how this program came to be, and why it’s still available despite the SAVE plan injunction. Plus, we'll touch on the importance of keeping an eye on refinancing rates and what to expect if policies shift under a new administration. If you’re worried about PSLF or wondering how things might change under a different political landscape, this episode has the answers to help calm your nerves.
Key moments:
(01:51) The exact steps and language needed to apply for PSLF buyback
(05:32) How PSLF buyback could save borrowers a ton of money
07:34) Potential impacts if a Trump administration repeals PSLF buyback or the SAVE plan
(11:02) How falling refinancing rates could create new opportunities for borrowers
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Social media is overflowing with flashy trends and hyped-up advice, making it easy to feel like you’re missing out. From “get rich quick” schemes to so-called success shortcuts, the constant FOMO can lead to bad financial habits and second-guessing your decisions. We’re exposing the trends that claim to help but actually hold you back. Discover how harmful financial behaviors and misleading investment advice can keep you stuck — and learn how to avoid these traps. Tune in for practical tips to cut through the noise and focus on building real, sustainable financial success.
Key moments:
(01:39) Influencers say “do this,” but their success doesn’t mean it’ll work for you
(10:07) Are you falling behind, or is social media making you feel that way?
(22:47) Unqualified influencers sell dreams, but they rarely deliver real results
(29:53) Hustle culture glamorizes nonstop work but keeps you from what really matters
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Over the past four years, student loans have been at the center of some of the most dramatic changes we’ve ever seen — both good and bad. We’ll explore the Biden administration’s legislative and executive actions, such as making student loan forgiveness tax-free through the American Rescue Plan, the PSLF waiver, and the introduction of the SAVE plan. Along the way, we’ll unpack the political pressures Biden faced, comparisons to FDR, and the influence of key players like Senator Warren and Richard Cordray. In addition, we’ll examine the political ramifications and speculate about the future of student loan policies under a Republican-controlled government.
Key moments:
(06:13) Misrepresented loan repayments paved the way for executive actions
(11:01) A once-in-a-generation opportunity to rewrite the social contract
(17:57) Why Republicans saw an opening to sue over student loan cancellation
(21:13) The SAVE plan’s billion-dollar promise — and why it was never realistic
(26:08) Are plans in motion to roll back Biden’s student loan reforms? What we’re hearing
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Roth IRAs are a fantastic tool for building tax-free retirement wealth, but they’re not without their pitfalls. Uncover common Roth IRA mistakes, like contributing too much, missing key deadlines, or triggering taxes you didn’t expect — and how to avoid them. Already made a misstep? Don’t worry. We’ll walk you through how to fix these mistakes, from recharacterizing contributions and correcting excess contributions to handling IRS notices.
Key moments:
(04:35) Why a Backdoor Roth IRA might be right for you (and the new 2025 phase-out limits)
(10:01) The five steps to completing a Backdoor Roth IRA
(16:32) Common Roth IRA mistakes and how to fix them
(19:27) The Pro Rata Rule and its potential tax consequences
(24:57) Strategies to avoid taxable conversions
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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If you're counting down your final PSLF payments and feeling like you're losing your mind with all the uncertainty, this episode is for you. We'll tackle what's actually worth worrying about when you're close to forgiveness, explore strategies for navigating the final stretch, dig into the PSLF buyback situation, and cover what you need to know about potential new repayment plans and legislative changes on the horizon.
Key moments:
(01:19) Misinformation about applying for PSLF buyback: What’s real and what’s noise
(08:31) Court rulings, tax changes, and what they mean for forgiveness programs
(15:14) What to do while waiting for IBR application processing
(16:07) New Republican proposal to reset student loan interest ratesLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Stuck in holiday traffic? Make the most of your travel time with our curated collection of student loan resources perfect for your commute. We'll explore the latest Pay As You Earn (PAYE) rumors, tackle tricky PSLF payment count challenges, and share a simple yet effective tool to estimate your IDR forgiveness progress while we wait for the Department of Education’s much-anticipated tracker.
Key moments:
02:41 New resources you’ll love: Podcasts for dentists, physicians, and veterinarians
05:36 How to pinpoint your payment count if you’re curious where you stand on forgiveness
14:11 Nearing 120 payments? Don’t miss this step-by-step guide we’ve been sharing with our clients
28:23 PAYE might be making a comeback: The pros, cons, and what it could mean for youLinks mentioned:
PSLF payment tracker through StudentAid.gov https://studentaid.gov/app/api/nslds/payment-counter/summary Financially Free Dentists podcast Financially Free Physicians podcastLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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The last few weeks have been a lot — election chaos, tensions running high, and now Thanksgiving is knocking on the door. If the thought of sitting at the table with family members who have very different opinions makes you cringe, you’re not alone. We've brainstormed tons of fun and unconventional methods to sidestep political tension, avoid unnecessary drama, and maybe even have a little fun. Plus, we'll explore the power of gratitude, the tactical use of distraction, and even a few spicy clap-back comebacks for when things get a bit too heated. Think of it as your guide to surviving the holidays without losing your cool (or your plate of pie).
Key moments:
(03:16) Turn the table into a stage with over-the-top campaign speeches for the best side dish
(05:28) How to keep stressful conversations in check without drawing attention
(13:05) Push boundaries with a bold clap-back (or stick to the nod-and-smile technique for a drama-free approach)
(20:06) Two ways to handle conspiracy theories: a smooth exit or playful engagement
(23:12) A low-key hack for escaping post-meal chaos while earning brownie points
Turkey, Tension, and Dodging DramaLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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It’s an unlikely scenario, but the possibility of President Trump abolishing the Department of Education in his second term is a hot topic that’s sparked questions and concerns among student loan borrowers. We’ll explore what that might mean, unpack the fears and anxieties expressed by our listeners, and provide context around the policy implications. Plus, stick around for our “listener mailbag,” where we tackle specific questions and worries that have been pouring into our inboxes.
Key moments:
04:31 Republicans' plan is not actually to eliminate the Department of Ed
10:21 How to handle income recertification for IDR plans during job gaps
16:04 Will the discontinued PAYE plan return amid changes?
22:37 Timing actions around the 0% interest period for student loansLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Ready to turn up the heat on your finances before 2024 comes to a close? We’ve packed this episode with 15 savvy, high-impact financial moves to help you finish the year on top. From maxing out retirement contributions and exploring tax loss harvesting to utilizing backdoor Roth strategies and refinancing high-interest debt, we’re covering it all. We’ll also discuss year-end must-dos like reviewing your insurance, managing FSA funds, and checking your credit report. Tune in to make the most of the final stretch of 2024 and set yourself up for a strong start in 2025.
Key moments:
04:05 Tax-loss harvesting and backdoor Roth IRA can help trim your tax liability
09:47 A personal story on listing income sources to stay in the clear with the IRS
13:40 With interest rates coming down, now might be the perfect time to refinance student loans or your mortgage
17:42 Important tips on updating insurance coverages and taking advantage of open enrollment benefitsLinks mentioned:
The Next 4 Years of Student Loans: Major Changes Are Coming Check Student Loan Refinance Interest Rates IRS Tax Withholding EstimatorLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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With Trump’s unexpected victory in the popular vote and key swing states, and a likely Republican majority in Congress, significant changes to student loan policies may be on the horizon. We’ll look at possible shifts in Public Service Loan Forgiveness (PSLF) that could make it harder to qualify, and the potential elimination of the Saving on a Valuable Education (SAVE) plan. We’ll discuss recent court rulings that could reshape repayment strategies, like the 8th Circuit Court decision on the Income-Contingent Repayment (ICR) statute. We'll also touch on political dynamics influencing these changes, including Republican and Democratic strategies, the implications of past proposals like the Prosper Act, and what borrowers need to consider moving forward.
Key moments:
04:18 Likely elimination of the SAVE plan — when should you consider switching to a different repayment option?
08:27 Republicans are making their own IDR plan and how past proposals threatened borrowers
18:42 Loan forgiveness potential might be more generous than we think
24:22 Potential for major policy changes under Trump’s second termLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Could your tax filing status save you thousands on student loan payments? You're about to find out. We’re discussing how choosing to file jointly or separately can impact your student loan repayment strategy. You’ll hear about real-world scenarios, from high-income couples evaluating their tax implications to the strategic benefits of filing separately in community property states. Plus, we’ll explore how recent legislative scrutiny on loan repayment plans could affect your financial planning.
From navigating recertification dates to leveraging tax extensions, you'll gain practical insights that could reshape the way you manage your taxes and student loans.
Key moments:
05:18 Should a dual-dentist household file taxes separately? A real case study
18:00 Myths vs. reality of tax filing extensions
22:13 How filing taxes separately changes everything in a community property state
26:42 A physician-teacher couple cashes in on the breadwinner loophole
35:31 Reclaim your money by amending your MFS tax return
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Have you ever wished you could give your debt — and even your degree — back? The weight of student loans is no joke, but returning it won't improve your life. The truth? You're underestimating the position you're in. A professional degree offers more job security, higher income potential, and better protection during economic downturns. Stop beating yourself up and start recognizing the smart financial decisions you've made.
In today’s episode:
05:04 Your career choice might not impact your happiness as much as you think
10:22 Feeling stress and shame? You're in a better position than you think
12:26 Prioritizing happiness and setting healthy financial boundariesLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Bringing a child into the world is one of life’s greatest joys — and one of its biggest financial commitments. With so much to consider, it’s easy to feel overwhelmed. Learn real-life insights, personal stories, expert advice and practical tips to help make this transition as smooth as possible.
Key moments:
09:13 Health insurance coverage, costs, co-pays and coinsurance explained
14:44 How to take parental leave without going broke
20:12 Hidden advantages of pregnancy on your student loan payments
29:18 Balancing life insurance, estate planning and retirement goalsLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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The SAVE lawsuit hearing did NOT go well for borrowers. What happens if SAVE was ruled to be unconstitutional along with the ICR statute? In this episode, we will share more about the challenges the SAVE plan is facing and what borrowers should consider up ahead.
Key moments include
01:30 What are the current SAVE lawsuits?
04:50 Student loan uncertainty causing statute confusion
12:35 SAVE plan forbearance considerations
17:38 PSLF real talk and how it is limited to certain groups
21:15 How politicians see student loan repayment plans
22:10 What borrowers should consider up aheadLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Think you’re making the most of your health benefits? It’s open enrollment, and we’re decoding everything you need to know, from why HSAs are the most overlooked investment vehicle to the surprising perks hiding in your benefits package.
In today’s episode:
01:58 Making sense of health insurance HMOs, PPOs, high-deductible health plans, and HSAs
20:57 The big issue with group life insurance and disability insurance policies
32:07 Maximizing legal benefits and estate planning protection
36:37 Protecting the whole family with pet insuranceLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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If you graduated back in May, your student loan grace period is about to expire. Get the inside track to navigate this new financial responsibility and manage recertification details. You’ll also find out the latest updates on forbearance options, hear success stories of borrowers who’ve benefited from payment recalculations and plan switches, and explore possible loopholes that might emerge if SAVE is repealed.
In today’s episode:
01:37 New grads must decide on loan repayment plans
11:30 Recertification timelines post-COVID forbearance
21:34 SAVE plan forbearance may be extended
28:52 The “double debt” loophole if SAVE is repealedLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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We’re exploring spending and creative shopping tips beyond the age-old advice of setting a holiday budget. Get tips you can actually use to keep your finances in check from Halloween to the new year.
In this episode:
01:47 Hidden holiday costs and how to catch up after a really expensive month
12:18 Shopping tips for Halloween candy and costumes and nailing the lowest price on gifts
23:23 Get crafty and frugal with DIY gifts and holiday activities, plus Sim’s favorite holiday tip
32:19 Setting expectations with family to lower your stress levelsLinks mentioned:
Ally
Capital One
thredUP
Honey
Kroger
Publix
Target Circle
Like the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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Imagine a world where the SAVE plan is struck down by the courts, taking various income-driven repayment (IDR) plans with it and leaving millions of borrowers scrambling. This worst-case scenario could block hundreds of thousands from accessing Public Service Loan Forgiveness (PSLF) and introduce massive complications for those on IDR plans. But don’t worry, I’ll break down this doomsday scenario, discuss its implications, and offer strategies for how you can best prepare.
Highlights from this episode:
02:37 Tougher eligibility for PSLF and income-driven repayment
06:33 Key tax strategies (reducing AGI, filing separately, and community property considerations)
09:36 Why I’m not overly concerned just yet
16:51 How to make sure you can still get a spot on the IBR planLike the show? There are several ways you can help!
Follow on Apple Podcasts, Spotify or Amazon Music Leave an honest review on Apple Podcasts Subscribe to the newsletterFeeling helpless when it comes to your student loans?
Try our free student loan calculator Check out our refinancing bonuses we negotiated Book your custom student loan plan Get profession-specific financial planningDo you have a question about student loans? Leave us a voicemail here or email us at [email protected] and we might feature it in an upcoming show!
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