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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected]., 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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] 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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected]. 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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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 [email protected] or follow his Tiktok channel - https://www.tiktok.com/@curbelofinancialcoach

To contact Shawn Yesner, you can email him at [email protected] 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

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

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

To contact Shawn Yesner, you can email him at [email protected] or visit www.YesnerLaw.com.