Info

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.
RSS Feed Subscribe in Apple Podcasts
2026
May
April
March
February
January


2025
December
November
October
September
August
July
June
May
April
March
February
January


2024
December
November
October
September
August
July
June
May
April
March
February
January


2023
December
November
October
September
August
July
June
May
April
March
February
January


2022
December
November
October
September
August
July
June
May
April
March
February
January


2021
December
November
October
September
August
July
June
May
April
March
February
January


2020
December
November
October
September
August
July
June
May
April
March
February
January


2019
December
November
October
September
August
July
June
May
April
March
February
January


2018
December
November
October
September
August
July
June
May
April
March
February
January


2017
December
November
October
September
August
July
June
May
April
March
February
January


2016
December
November
October
September
August
July
June
May
April
March
February
January


2015
December
November


All Episodes
Archives
Now displaying: October, 2025
Oct 30, 2025

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: https://www.patreon.com/crushingDebt  

To contact George Curbelo, you can email him at GCFinancialCoach21@gmail.com or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach  

To contact Shawn Yesner, you can email him at Shawn@Yesnerlaw.com or visit www.YesnerLaw.com.

And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026 

Oct 23, 2025

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 RAguanno@HomeCareAssistance.com or her website www.HomeCareAssistanceTampaBay.com

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: https://www.patreon.com/crushingDebt

To contact George Curbelo, you can email him at GCFinancialCoach21@gmail.com or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach  

To contact Shawn Yesner, you can email him at Shawn@Yesnerlaw.com or visit www.YesnerLaw.com.

And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026 

Oct 16, 2025

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 www.TiffanieKellog.com. And, Tiffanie is giving all of our listeners a free gift by going to this link: https://moreabundantentrepreneurs.com/moretime 

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: https://www.patreon.com/crushingDebt  

To contact George Curbelo, you can email him at GCFinancialCoach21@gmail.com or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach  

To contact Shawn Yesner, you can email him at Shawn@Yesnerlaw.com or visit www.YesnerLaw.com. And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026 

 

Oct 9, 2025

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 (www.BestyBookkeepers.com). 

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: https://a.co/d/2JDV3So

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 www.BestyBookkeepers.com or Emily@BestyBookkeepers.com. 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: https://www.patreon.com/crushingDebt  

To contact George Curbelo, you can email him at GCFinancialCoach21@gmail.com or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach  

To contact Shawn Yesner, you can email him at Shawn@Yesnerlaw.com or visit www.YesnerLaw.com. And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026 

Oct 2, 2025

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: https://www.patreon.com/crushingDebt  

To contact George Curbelo, you can email him at GCFinancialCoach21@gmail.com or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach  

To contact Shawn Yesner, you can email him at Shawn@Yesnerlaw.com or visit www.YesnerLaw.com

 And please consider a donation to Pancreatic Cancer research and education by joining Shawn's team (reactivated for 2026) at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026 

 

1