Crushing Debt Podcast
The Crushing Debt Podcast is for people who want to eliminate the financial bullies in their lives. It is for listeners who want more money at the end of the month, rather than more month at the end of the money. The podcast provides answers around such topics as real estate litigation, partition, quiet title, chapter 7 liquidation, chapter 13 reorganization, and Chapter 11 business bankruptcies, short sales, loan modifications, creditor harassment and other related topics.
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Financial Advice Your Rich Uncle Should Not Be Giving You! - Episode 513
05/07/2026
Financial Advice Your Rich Uncle Should Not Be Giving You! - Episode 513
What is one piece of advice you received that is really useful? What about advice that you would rather ignore? On today's episode of The Crushing Debt Podcast, as Graduation 2026 nears closer, Shawn & George talk about financial advice you may have received - good, bad or otherwise - like: Follow your passion Do what you love Take risks while you're young Money will come later You deserve it - put it on a card What advice should you follow? What should you ignore? Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . Although PanCAN 2026 is over, there's still time to donate to the 2026 team, MY Legacy Striders:
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Finding Hidden Cash - Episode 512
04/30/2026
Finding Hidden Cash - Episode 512
Buying a house? Can you get assistance with your downpayment? Are there income requirements for getting downpayment assistance? Do you have to be a first time homebuyer to get downpayment assistance? What is the difference between MIP and PMI? On this week's episode, we talk to Michael Banner for his fourth appearance on the show. You can hear Michael on episodes: 400 - Sleeping Giant of the Senior Real Estate World - HECM for Purchase 384 - The Secret to Moving Forward in Reverse 120 - Safely Using a Reverse Mortgage Michael is also the host of the 62 Who Knew Podcast, which you can find where you listed to the Crushing Debt Podcast. He is also a national speaker on logevity. You can reach Michael at . Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . Although the PanCAN Purple Stride walk is over, we will be gearing up soon for the 2027 walk. The link to donate for this year's walk will be active until June 1, 2026, MY Legacy Striders:
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ChatGPT Told Me to Invest in WHAT?! - Episode 511
04/23/2026
ChatGPT Told Me to Invest in WHAT?! - Episode 511
AI is becoming a financial “advisor”… but does it know you? Are you using AI for budgets, investing, medical or even legal advice? Should you trust AI with your money? AI can give you answers… but it can’t give you accountability.” On this week's episide Shawn & George asked AI for Financial Advice: What AI Gets RIGHT (Be fair and exciting) What AI Gets WRONG (or Dangerous) AI & Investing: Opportunity vs Risk AI & Bankruptcy / Debt Decisions AI & Jobs The Money Impact Everyone Feels How to Actually Use AI the RIGHT Way in finance and debt situations. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . If you get this on the day or it's release, there is still time to donate to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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We Thought We Knew Money, We Were Wrong! - Episode 510
04/16/2026
We Thought We Knew Money, We Were Wrong! - Episode 510
What are some confessions about money that you don't want to admit? What were you taught about money versus what is reality about money? If you could start over with money, or had to start over with money, what would you do? Financial literacy isn’t about being “smart with money”… it’s about unlearning bad habits we picked up growing up, on TikTok, or just by surviving life. April is Financial Literacy Month… so we’re confessing all the things we should’ve known but didn’t—and what to actually do about it. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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How to Pay Off Debt Faster - Episode 509
04/09/2026
How to Pay Off Debt Faster - Episode 509
Are you using personal credit cards to run your business? Are you traking what you spend by category? Do you have multiple "deferred interest" or "90-days same as cash" debt balances? If so, then this week's podcast episode is an interview by Shawn & George of Nancy Ward, of . There's a moment a lot of solopreneurs hit: they're putting in the work, the business is moving, and yet the financial reward just doesn't match the effort. Nancy Ward built her entire practice around that moment. As a financial coach and founder of Weekly Debt Plan, Nancy helps small business owners who are running on personal credit cards and avoiding their finances get clear on where their money is actually going, so they can stop the cycle and start paying themselves what they actually deserve. No budgeting lectures, no accountant speak. Just real clarity and a path forward. You can contact Nancy at the website above, or at . Her website also has a TON of useful resources for solopreneurs that need budgetary help. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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TikTok University. Financial Degree or Disaster? - Episode 508
04/02/2026
TikTok University. Financial Degree or Disaster? - Episode 508
What does TikTok get right, and what does it get very wrong? Girl Marth and Boy Math, what could go wrong? On this week's episode of the podcast, Shawn and George doomscroll ... um deep dive into some TikTok advice. What do we agree with? Disagree with? Laugh with, and laugh at? You can watch the videos directly on TikTok at these links: Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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March Madness, the Worst Money Habits - Episode 507
03/19/2026
March Madness, the Worst Money Habits - Episode 507
March Madness is one of our favorite times of the year! Therefore, we've put together a list of the 16 worst money habits, in a "Salty-16" to see which habit wins as the worst habit. LEFT REGION: Everyday & Emotional B1 · EVERYDAY MONEY LEAKS 1 Daily impulse spending vs. 16 Forgotten subscriptions People instantly relate. B2 · EMOTIONAL SPENDING 8 Stress shopping vs. 9 Rewarding yourself every hardship When does self-care become self-sabotage? B3 · AVOIDANCE HABITS 5 Not checking your bank account vs. 12 Ignoring CC statements “Avoidance charges interest.” B4 · LIFESTYLE INFLATION 4 Upgrading lifestyle after every raise vs. 13 Financing things to feel successful The dark horse of the left region. RIGHT REGION: Debt & Budget B5 · DEBT BEHAVIOR 5 Paying only minimum payments vs. 12 Saying “I'll deal with debt later” Minimums feel like progress. They're not. B6 · SOCIAL PRESSURE HABITS 4 Spending to keep up w/ friends vs. 13 Saying yes to every event broke FOMO is an expensive habit. B7 · BUDGET SABOTAGE 6 Guessing instead of tracking vs. 11 Starting budgets, quit after 5 days The Cinderella pick. Could go all the way. B8 · FALSE CONFIDENCE HABITS 3 High income solves everything vs. 14 One good month = problem solved Overconfidence is a budget's worst enemy. Highlighted row = analyst's pick to advance Who do you think will win? Who is your darkhorse, your Cinderella? Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Chasing Luck Instead of Building Stability - Episode 506
03/12/2026
Chasing Luck Instead of Building Stability - Episode 506
What is a lucky break? Were they lucky or were they ready? Can you actually create your own luck? How do you position yourself to be lucky? How do you engineer your own luck? On this week's episode, Shawn & George, two professionals who've seen it all - one from the courtroom, on from the coaching room - dismantle the myth that financially successful people are simply lucky, and make the case that "luck" is something you can actually manufacture with the right preparation, mindset, and timing. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Forgive Me For I Have Spent - Episode 505
03/05/2026
Forgive Me For I Have Spent - Episode 505
Welcome to the Religion of Crushing Debt, where we regularly confess our sins and ask for forgiveness. What sins have you committed that you would like forgiveness from Shawn & George? In this week's episode, we talk about financial "sins" most borrowers make, even innocently or unbeknownst to them. Some of the sins include: I make money but live paycheck to paycheck. I maxed out my 401(k) but haven't talked to my spouse in months. I used my HELOC to buy Crypto Currency. I haven't filed taxes in three years because I'm afraid of what I owe. My business is profitable, but I pay myself nothing. I bought a car I cannot afford because my friends have one. I co-signed for my kids' loan. I have a high-paying job that I hate. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Ten Things Holding You Back From Building Wealth - Episode 504
02/26/2026
Ten Things Holding You Back From Building Wealth - Episode 504
What are some common things that hold people back from building wealth? What can you do to avoid or counter these things, and how can you build wealth? On this week's episode of the Crushing Debt Podcast, Shawn & George talk about ten things that typically hold people back from building wealth and what they can do about it, including: Lifestyle Creep / Inflation Confusing consumption with investing High Interest Debt Lack of clarity / not knowing your numbers Avoiding discomfort, or being comfortable in the discomfort No savings for emergencies Comparison / Keeping up with the Joneses / Ego Waiting for the right time Helping everyone else before you're stable Mindset Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Money & Ego - Episode 503
02/19/2026
Money & Ego - Episode 503
Why is "we never fight about money" an unhealthy sign to a relationship? Can you overcome your ego to ask for help? This week's guest on the Crushing Debt Podcast is TJ Recinella, a financial coach, speaker, and the founder of TJR Financial Coaching, where he helps individuals and couples dream big and live free by moving from financial stress and confusion to clarity, confidence, and long-term freedom. You can contact TJ at . TJ ’s passion for coaching is deeply personal. Early in his marriage, he and his wife, Christy, experienced a life-altering family tragedy that forced them to confront grief, responsibility, and major financial decisions all at once. Guided by his personal and professional experiences, TJ and his wife eliminated over $300,000 in debt, fully funded their children’s education, and built a values-based financial plan rooted in preparation, margin, giving, and intentional living. Today, TJ walks alongside clients as a coach and accountability partner, helping them challenge cultural money myths, prepare for life’s uncertainties, and use money as a tool to support what matters most. We talk about how TJ got into debt, how he got out of debt, and his motivation for doing so. We also talk about how to have difficult money conversations with your spouse, without ego getting in the way. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Debt With Benefits - Episode 502
02/12/2026
Debt With Benefits - Episode 502
Happy Valentine's Day from The Crushing Debt Podcast! What is "good debt?" What is "bad debt?" What is debt that is neither good or bad? In this week's episode, Shawn & George talk about the difference between "good" and "bad" debt, including a four-question debt test: Does the debt help you earn more money? Is the interest rate under control? Would "future me" thank "present me" for this decision? If I lost my income tomorrow, would this payment wreck me? Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Debt, Dollars and the Power of Relationships - Episode 501
02/05/2026
Debt, Dollars and the Power of Relationships - Episode 501
Do you work with family? How does relationship-based networking impact your life? Your company? Your bottom line? What are some of the biggest misconceptions about networking? In this week's episode of The Crushing Debt Podcast, Shawn & George talk to Spencer Reynolds and his son Kamryn Reynolds, Co-Executive Directors of BNI Tampa. Originally from Northern Utah, Spencer and his family packed up and moved to Florida in 2017, trading mountains for sunshine and lakes. With his wife, Tricia, running the show (let’s be honest, she’s the boss) and their four incredible kids—three adventurous adult sons and their adopted princess, almost 16—they’re all about outdoor thrills, especially water sports and international adventure travel. And when we say “thrills,” we mean it! Spencer’s an adrenaline junkie—skydiving, hang gliding, mountain biking, and even trekking to Everest Base Camp with his brothers. If it involves speed, heights, or a near-death experience, he’s probably done it… twice. (Ask about their Grand Canyon White Water Rafting trip from last year, wild!) Before becoming the networking master he is today, Spencer spent 12 years as a mortgage broker before making the leap into professional speaking and training in 2005. He’s taken the stage in every major city across the U.S. and Canada, teaching professionals how to build systems, work By Referral Only, and grow businesses the right way with referrals. Through BNI, he’s expanded his reach globally, inspiring thousands of entrepreneurs to unlock the power of relationships. Kamryn Reynolds is a communication coach, keynote speaker, and the youngest Executive Director in BNI history. He’s the founder of Articulate Advantage, helping professionals speak with power, clarity, and confidence. A USF grad, Eagle Scout, and fluent Spanish speaker after serving a two-year mission in Argentina. Kamryn now specializes in keynotes and trainings for high-end hotels and resorts. Known for his high energy and practical frameworks, he’s on a mission to become an Ironman, a TEDx speaker, and an international voice for intentional communication. He lives by one core belief: connection is the currency of opportunity. Spencer, Kamryn, George & Shawn talk about: What surprises them the most about working together. Early money lessons. BNI / Networking Success Stories Biggest Misconception about BNI / Networking How long before networking pays off One business habit to adopt this year? To stop this year? Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Then & Now - EPISODE 500 !!
01/29/2026
Then & Now - EPISODE 500 !!
FIVE HUNDRED EPISODES of The Crushing Debt Podcast !! Who knew way back in November 2015, that the Podcase would: (1) turn 10 years old, and (2) celebrate episode 500? We like to think that The Crushing Debt Podcast is Florida's longest running legal episodic podcast - maybe even the Country's longest running... What have we learned over 500 (plus) episodes? What has changed in terms of money and debt in the last 10 years? What do we predict for the next 10 years? In this week's episode, Shawn & George take some time to reflect on 10 years and 500 episodes. We talk about the show's statistics, sponsorhips and relationships we've built over the years, memorable guests we've had, and memorable topics. We also talk about what has changed over the last 10 years in terms of money, mindset, and debt. If today's episode is the first one you've listened to, or the 500th you've listened to, we appreciate all of the great lessons we've learned doing this show over the years! Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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What Would You Do If You Had to Start Over in 2026? Episode 499
01/22/2026
What Would You Do If You Had to Start Over in 2026? Episode 499
What would you do if you had to start over in 2026? Would starting over be a reset or a setback? In this week's episode, Shawn & George talk about what you would do if you suddenly lost everything and you had to start over again. Unfortunately, this is a common theme amongst clients as they deal with job loss, divorce, poor economic conditions, health issues, etc. In this week's episode, we talk about: Stablizing Generating Fast Cash Building a Safety Net Triage the Debt Lifesstyle Creep Rebuild Credit Increase Income Invest (after stability) Setting new rules (so you don't repeat the same issues) Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Business Check-Up - Episode 498
01/15/2026
Business Check-Up - Episode 498
You should visit your doctor annually for a physical. Do you give your business an annual check up? If so, when? What things should you focus on in January as we start the new year? In this week's episode, Shawn & George talk about these topics and more, including: Tax Compliance Corporation or LLC renewal Reviewing Your Prior Years' Numbers Expense and Recurring Payments Audit Pricing Audit (should you charge more, or stay the same) Legal & Compliance Audit Personally, a checkin as to how you feel as the Owner. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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New Year, Same Debt - Episode 497
01/08/2026
New Year, Same Debt - Episode 497
Why do resolutions die? How do you beat the odds and make your resolutions a reality? On January 1, we all believe that we are about to become someone who meal preps, budgets, and never impulse buys. Does that always happen? On this week's episode of the podcast, Shawn & George talk about why resolutions die, including: Rebellion spending Waning motivation Shame or avoidance February Lack of tracking or monitoring Lack of specificity. More important, we also discuss how to beat the odds, including: Shrinking the goals Building systems Budgeting DIY Accountability Calendars Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Surviving The Holiday Hangover - Episode 496
01/01/2026
Surviving The Holiday Hangover - Episode 496
Happy New Year from the Crushing Debt Podcast! How do you manage your credit card debt after the holidays? What are some tips for starting the new year on the path to being debt free? Did you know that the average American household spends approximately $1,100 per person for gifts? In this week's episode of the podcast, Shawn & George talk about managing credit card debt after the holidays, including tips like: Budgeting & Planning Pausing new spending Using the Snowball or Avalanche Debt payment strategies Setting up Automatic Payments Doing a new year no spend challenge Resisting Impulse Buys Saving for next year NOW Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Debt is a Clutter Problem - Episode 495
12/25/2025
Debt is a Clutter Problem - Episode 495
Merry Christmas from The Crushing Debt Podcast !! How much "stuff" does the average American home have? How many people utilize off-site storage for their stuff? Are you able to park your car in your garage? How long do you take searching for "missing" items? How much does the average American family spend on non-essential goods. This week, Shawn & George talk to Beth Ruck with Conquering Clutter () about Statistics regarding the average amount of possessions of U.S. households Mindset regarding shopping and managing your possessions Paper management and how it can save you money How de-cluttering can help you conquer your debt. You can contact Beth at . At a young age, Beth learned from her mother that you can accomplish a lot in just 15 minutes. She has applied this idea in her roles as a homemaker, wife, and mother of two grown children. She holds a Bachelor of Science degree with a major in Accounting from the University of Wisconsin-La Crosse. She has worked as a bank teller, staff accountant for a commercial real estate firm, bookkeeper for three different non-profits, a substitute teacher, and a sales associate in a Christian book/gift store. She enjoys meeting new people, taking walks with her husband and dog, singing, knitting, reading and spending time with her granddaughter. In 2015, Conquering Clutter was established. Over the past 10 years Beth has enjoyed working with clients and hearing their stories. Her motto is: Helping people simplify their spaces so they have more time for what they love and who they love. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Moving Forward, Looking Back - Episode 494
12/18/2025
Moving Forward, Looking Back - Episode 494
What are your 2026 Resolutions? What are your 2026 Goals? What is the difference between a Resolution and a Goal? In this week's episode, Shawn & George flip the script on last week's episode and instead of looking back on 2025, they look forward to 2026, talking about things like: One Word for 2026 Goals for 2026, personally and professionally Trends for 2026, like Housing Interest Student Loans AI Homeowner & Condo Associations. And more! Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Looking Back, Moving Forward - Episode 493
12/10/2025
Looking Back, Moving Forward - Episode 493
As we near the end of 2025, how was this year for you? Personally? Professionally? What was some of the biggest financial news in 2025? What are you looking forward to in 2026? As the year comes to an end, Shawn & George take a look back, and a small look forward at 2025 and 2026, including topics like: Mortgage / Interest Rates Grocery and Utility costs Government Shut Down Student Loan Adjustments Credit Card Debt Personal Guarantees Housing Market Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Santa's Real Budget - Episode 492
12/04/2025
Santa's Real Budget - Episode 492
What can you learn about budgeting from Santa's Holiday preparation? What lessons do the holiday bring? On this week's episode of The Crushing Debt Podcast, Shawn & George talk about: Overhead costs Supply chain issues Labor force issues North Pole budgeting Budgeting among multiple celebrations Gift-giving expectations Holiday season cash-flow We hope you had an amazing Thanksgiving break and a great holiday season. For Thanksgiving, it would mean a lot to us for you to please share this episode with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Gravy, Gratitude & Getting Out of Debt! - Episode 491
11/27/2025
Gravy, Gratitude & Getting Out of Debt! - Episode 491
What Thanksgiving traditions do you have? Do you eat a big meal surrounded by family, a smaller meal with less people, or Thanksgiving is not really your thing? In this week's episode of The Crushing Debt Podcast, we wish everyone a Happy Thanksgiving. As has become our tradition, because we release the show every Thursday, Shawn & George talk about: Black Friday and Sales / Shopping Financial Advice around the dinner table What business owners can be thankful for this year Gratitude mindset Using Thanksgiving to air out financial dirty laundry Using Thanksgiving as a time to reflect and set goals for next year. Whether you celebrate, whehter you work tonight, whether you keep it low key or skip the holiday altogether, at The Crushing Debt Podcast, we do want to know what you're thankful for and we hope you have a great holiday season. Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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IRS Wins Again? - Episode 490
11/20/2025
IRS Wins Again? - Episode 490
Do you know what taxes are dischargeable in bankruptcy and which are not? Do you owe Trust Fund Tax? What if you cannot pay it? On this week's episode of the Crushing Debt Podcast, Shawn & George talk to Tax Attorney Alena Miles. Alena has an L.L.M. in taxation, and is a CPA. She is the founder of Attorney Legal and focuses her practice on federal tax law and international tax matters. She provides services in business tax planning, tax transactions, tax consulting, and tax controversy for a wide range of clients, including businesses, partnerships, corporations, LLCs, private equity funds, single-purpose entities, and individuals. With over 15 years of experience in public accounting, Alena has a strong background in tax compliance, tax planning, and tax dispute resolution. Before becoming an attorney, she worked as a Certified Public Accountant (CPA), assisting clients in industries such as asset management, real estate, McDonald's franchisees, professional services, investment, and construction. Alena has worked at leading Big Four accounting firms like PricewaterhouseCoopers (PwC) and KPMG, where she provided tax services to billion-dollar clients in asset management. As a Tax Manager at KPMG, she managed complex private equity funds and multi-tiered partnership structures, ensuring compliance with complex tax laws and regulations and meeting time-sensitive deadlines. Shawn & George talk to Alena about: Trust Fund Taxes Not Filing Your Tax Return Filing Late Returns Forced Filings by the IRS Negotiations with the IRS The Difference between a Tax Attorney and CPA FIRPTA (Foreign Investment in Real Property Tax Act) Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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FORE! Ways Golf Can Teach You About Debt! - Episode 489
11/13/2025
FORE! Ways Golf Can Teach You About Debt! - Episode 489
What lessons can you learn about selling from your kids? What lessons can you learn about debt from your kids? While we didn't get to participate in this year's community garage sale, my son did collect, clean and sell golf balls at a golf tournament recently. Some of the lessons he learned: Timing - know your market and their needs Networking - with other kids selling other items (like lemonade) Preparation - collecting, cleaning, sorting, labelling and pricing Investors - (dad, Shawn) to help buy supplies, provide the table for selling, etc. Using Revenue to Grow the Business (listen for the story of the golf ball cleaner) Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Who's More In Debt, You or Your Landlord - Episode 488
11/06/2025
Who's More In Debt, You or Your Landlord - Episode 488
Who's in more debt, Landlord or Tenant? How can landlords reduce costs and increase the profitability of their rentals? How can a property manager increase your profits and save you money? In today's episode, I interview Mark Sorokurs of Central Pinellas Realty and Collman Properties. I've known Mark about seven years and he's been in real estate for about eight years now after "retiring" from IT in 2012. You can also hear Mark in Episode 245 - You can reach Mark at or ., or 727-738-RENT (7368). Let us know if you enjoy this episode and, if so, please share it with your friends, like and subscribe to the show! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Financial Vampires - Episode 487
10/30/2025
Financial Vampires - Episode 487
Happy Halloween! On October 31, do you give out candy? Do you turn your lights off and pretend not to be home? Do you go to Halloween parties? What "vampires" are out there sucking your wallet dry? On this week's episode, Shawn & George take a funny look at those "vampires" that you should avoid, like Subscription Vampires Convenience Fee Vampires Tipping Vampires Lifestyle Vampires Tax Debt Vampires Buy Now, Pay Later Vampires Friend / Family Vampires Overdraft Vampires Store Credit / BOGO Vampires Interest Vampires And more ... You can also listen to other Halloween-themed shows like Episode 438: Debt Graveyard Episode 211: Zombie Cars Episode 88: Zombie Debt Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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Mom, Dad & My Credit Card Bill! - Episode 486
10/23/2025
Mom, Dad & My Credit Card Bill! - Episode 486
How are you handling the rising cost of health care for your parents? How can you talk to your mother & father about the rising costs of health care and senior living? Should your parents age at home or in an assisted living facility? This week, Shawn & George talk to Rachel Aguanno, owner of Home Care Assistance Tampa Bay. Rachel's company assists seniors to live at home. Rachel was a HUGE help to Shawn when his wife was in hospice at home at the end of 2023. Specifically, we talk about: Care-giving as a side job; What a home care assistance company can or cannot do; Any tax breaks, insurance, government programs, or veteran benefits available to help pay for home health care; Hospice v. Home Health Care v Assisted Living; Expenses people don't think about; and other budget considerations. Rachel can be reached at or her website . Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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The Entrepreneur's Guide To More Free Time - Episode 485
10/16/2025
The Entrepreneur's Guide To More Free Time - Episode 485
When does an entrepreneur make time? How can an entrepreneur work 27 hours a day? How hard (or easy) is work-life balance? On this week's episode, Shawn & George interview Tiffanie Kellog who today (if you're listening on the day of release) releases her FOURTH self-published book, The Entrepreneur's Guide to More Free Time. Tiffanie is the Sock-it-to-'em Success Strategist! Since 2005, Tiffanie has been revolutionizing entrepreneurs' paths, unlocking greater wealth, freedom, and joy! As the creator of “eTiffanies” — epiphanies inspired by Tiffanie — she is known for her signature socks (over 400 pairs!), a charming southern accent, and her unique ability to inspire and empower others. Whether delivering dynamic keynote presentations, training locally and globally (often virtually), writing her next book, or leading her More Abundant Entrepreneurs community, Tiffanie loves helping people create the life they desire. With a passion for blending fun and strategy, Tiffanie helps her clients focus on achieving their goals while loving the journey. Her secret to success? Loving what she does so much that no one can tell if she’s working or playing! Are you ready to sock it to your challenges, make more money, save time, and have fun? This is Tiffanie's seventh appearance on the podcast: Episode 381 (Talking about the no spend challenge) Episode 332 (Making time to crush your debt) Episode 242 (More money through masterminds) Episode 146 (13 months a year) Episode 76 (Referrals for Life) Episode 48 (Knock your socks off Speaking) Now Tiffanie is working on time management, or priority management, and how you can avoid BSO (Bright Shiney Objects) in your day. And rather than Work/Life balance, we focus on Harmony or being "Off Balance On Purpose." You can get your copy of Tiffanie's new book or her previous three books at . And, Tiffanie is giving all of our listeners a free gift by going to this link: Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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The Real Reason Businesses Fail - Episode 484
10/09/2025
The Real Reason Businesses Fail - Episode 484
What is the real reason 90% of businesses fail? What are some bookkeeping or CFO mistakes most business owners make that can tank your business? On this week's episode of The Crushing Debt Podcast, George and Shawn talk to Emily Handren, owner and founder of Besty Bookkeepers (). For over two decades, Emily has helped individuals and businesses improve their financial situations through banking, investing, lending, and insurance guidance. She has owned both life/health and P&C agencies, and has plenty of real-world stories about helping people reduce costs and increase their net worth. Emily recently wrote a book "The Real Reason 90% of Businesses Fail: 101 Bookkeeping and CFO Mistakes You Can't Afford to Make" that hit #1 in three categories: Small Business Bookkeeping, Entrepreneurship Management, and Business Planning & Forecasting. It focuses on practical money management strategies for businesses that could tie perfectly into debt reduction discussions. Here's the link if you'd like to check it out: In this episode, we talk about: Fractional CFO Bookkeepers v. Accountants Tech stacking Financial Forecasting Some of the 101 Mistakes, like: Exponential growth without a plan or foundation Improperty business structure knowing your expenses and your numbers using an outdated accounting system not paying yourself. You can reach Emily at her website or . Make sure you take the "Need a Better Bookkeeper" quiz on her website! Let us know if you enjoy this episode and, if so, please share it with your friends! Or, you can support the show by visiting our Patreon page: To contact George Curbelo, you can email him at or follow his Tiktok channel - To contact Shawn Yesner, you can email him at or visit . And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders:
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