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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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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Student Loan Solutions & Discharges - Episode 483
10/02/2025
Student Loan Solutions & Discharges - Episode 483
What is the test for discharging a student loan in bankruptcy? Is it even possible? Student loans are non-dischargeable, right? WRONG !! On this week's episode, Shawn is back solo again (we'll hear George back again for next week's episode) interviewing attorney Jeff Hakanson. Jeff has been an attorney for thirty (30) years! He granduating with his J.D. from South Texas College of Law and has practiced bankruptcy for his entire career. On November 17, 2022, the U.S. Department of Justice issued a memorandum on student loan discharges. What normally fell under the Brunner case and a Totality of Circumstances argument has now been streamlined by the US DOJ to assist in discharging student loan debts under certain circumstances, some of which include: The borrower is over 65; The borrower has a disability; The borrower has been unemployed 5 of the last 10 years; The borrower has attempted repayment in good faith. Typically these discharge cases are started with the filing of an Adversary Proceeding (with no fee if related to Student Loans) and then the debtor / borrower and attorney complete a "litigation package" with certain "attestations." If the DOJ agrees, then the student loans can be discharged, or maybe modified in some capacity. The memorandum was designed to allow borrowers more clarity on discharging federally backed student loans (not private loans). 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 (reactivated for 2026) at MY Legacy Striders:
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What if I Can't Afford To Pay For My Kids' College? - Episode 482
09/25/2025
What if I Can't Afford To Pay For My Kids' College? - Episode 482
Image someone, 54 years old with no savings and $90,000 in debt. How can that person admit to their kid that they cannot afford to pay for college? That is the topic of this week's episode. Shawn & George talk about: Facing the reality of the situation Honesty with your kids Exploring all funding options Dealing with the situation Reworking income & expenses Making a future rebuilding plan Small wins and other stretegies 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 www.YesnerLaw.com.
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Building Financial Literacy for Vulnerable Communities - Episode 481
09/18/2025
Building Financial Literacy for Vulnerable Communities - Episode 481
What is the Big Beautiful Bill, and why is it such a pivotal moment for financially vulnerable communities? What are the biggest gaps you see between how legislation is written and how it actually plays out in people’s day-to-day lives? What are the five simple steps anyone can take today to protect themselves financially in light of this legislation? What role does mindset play in becoming financially literate, and how can we help people make that shift? In this week's episode, Shawn interviews Michelle Campbell, the author of Bluebird, a memoir that candidly explores themes of trauma, heartbreak, and the resilience found in life’s struggles. She is also the founder of a nonprofit organization dedicated to empowering individuals through financial literacy and fostering economic stability. Michelle was born and raised in Omaha, Nebraska, and began her educational journey in South Dakota before relocating to Atlanta, Georgia, to continue her studies. During her academic pursuits, she launched a real estate investment firm, marking the beginning of her entrepreneurial path. Over the years, Michelle expanded her ventures into various industries, including horticulture, where she founded an interiorscape company, and logistics, where she established a commercial trucking business. Drawing on the insights and expertise gained across these diverse fields, she transitioned into a career in the financial services industry. You can connect with Michelle at: We missed George this week, but he'll be back next week! 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 .
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No, You're Not Selling Grandma's House - Episode 480
09/11/2025
No, You're Not Selling Grandma's House - Episode 480
With a reverse mortgage, can you retain title to your home? Are reverse mortgages insured or guaranteed? Do reverse mortgagaes have a maturity date? This week's guest on the Crushing Debt Podcast is Gary Guarino, Vice President with Senior Lending, focusing on the HECM (Home Equity Conversion Mortgage), better known as a reverse mortgage. Gary has been a VP of Senior Lending for the last 26 years and is a Home Equity Retirement Specialist. He is regarded as a leading expert on every aspect of the FHA-Insured HECM Credit Line as well as the proprietary Jumbo Reverse Credit Line. You can reach Gary at , or visit his website at . Shawn, George & Gary talk about Myths (and facts) surrounding reverse mortgages Title theory v. lien theory FHA Insured products Recourse v. Non-Recourse loans What is required to borrow under a reverse mortgage And other questions regarding HECM loans. 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 .
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From Taxes To Treasure - Episode 479
09/04/2025
From Taxes To Treasure - Episode 479
What is the difference between a Tax Certificate and a Tax Deed? What is the investment opportunty in Tax Certificates and Tax Deeds? How do you get started? On this week's episode of The Crushing Debt Podcast, Shawn & George talk to Brian Seidensticker, managing partner and founder of Last Best Partners as well as the founder and CEO of Tax Sale Resources. With a strong background in systems engineering and an advanced understanding of the tax sale industry, Brian has been instrumental in transforming the way investors access tax lien and tax deed information. His expertise in design and programming enabled the development of a comprehensive online platform that not only delivers accurate tax sale data but also effectively tracks investor needs, setting a new standard in industry due diligence and efficiency. You can reach Brian at or . Or email him at . Shawn, George & Brian discuss: How to get started with investing in unpaid taxes. The opportunities in vacant land vs. houses. Superiority of liens. Tyler v. Hennepin case (and what it means for tax investors) Please also check out Brian's podcast - The Tax Sale Insiders Podcast, as well as his blog and other free resources! 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 .
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From Allowance to Assets! - Episode 478
08/28/2025
From Allowance to Assets! - Episode 478
Do your kids have a paper route, or sell lemonade, or sell crafts they've made themselves? Did you? How can you help foster an entreprenurial mindset in your kids? How can your kids learn about the basics of business - planning, branding, marketing, sales, goals, operations, inventory, cash flow, profits & losses? On this week's episode of the Crushing Debt Podcast, Shawn & George talk to Kelly Gersonde, Co-Owner of Kids Market, designed to provide kids with the opportunity to develop real-world business skills by creating and selling their own products and services in a supportive marketplace environment. Being a business professional for over 15 years, Kelly has experience with marketing, business plans, sponsorships, and partnerships. Her experience will help grow Kids Market exposure and support so the kids can develop and focus on their businesses. Kelly has a degree in marketing from the University of Wisconsin and is a mom of a little boy and a fur baby. You can reach Kelly at , or checkout Kids Market directly 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 .
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