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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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Now displaying: November, 2025
Nov 27, 2025

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: 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

 

Nov 20, 2025

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: 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 

Nov 13, 2025

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: 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 

Nov 6, 2025

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 - Saving Money by Using a Property Manager

You can reach Mark at www.centralpinellasrealty.com or office@colemanproperties.com., 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: 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 

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