Although we're in summer, the start of school is just around the corner. Are you ready?

How do you get ready for school every year?

Shawn has two kids - one in high school and one in middle school. George has one in college (and one who just graduated college).

Some of the expenses you may incur for kids going back to school:

• Books
• Supplies
• Lunches
• Clothes / Uniforms
• Sports / Extracurricular Activities
• Electronics (computer, calculator)

What hidden expenses are there that we have not mentioned?

Where can you cut costs, like hand-me-downs, splitting supplies between kids, and taking advantage of sales tax holidays.

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.

Back in March (episode 507), we did a show about the "Sweet 16" worst money habits to see which was the worst for your wallet and budget. We decided to bring that episode back, but with 16 new "bad" money habits based on a World Cup-style seeding.

• Subscription creep
• Food delivery apps
• Impulse buys ("just this once")
• Convenience store runs

• Buy Now, Pay Later (BNPL)
• Car payment stretching (72–84 month loans)
• Lifestyle creep after a raise
• "It's an investment" purchases (boat, timeshare, unused home gym)

• Revenge spending (stress/reward shopping)
• Retail therapy after a bad day
• Keeping up with social media lifestyles
• Guilt spending on kids/grandkids

• "I'll start Monday" mentality
• "It's just one swipe" thinking
• No budget or tracking at all
• Balance transfer as a permanent fix instead of a plan

Which money habit do you think will "win" (and by that, we mean which will be the worst? This is all in good fun; the goal isn't perfection — managing money is genuinely hard, and just noticing a pattern is real progress. Do you agree with our analysis?

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.

Why will paying off debt not make you wealthy?

What is the tax trap inside your debt payoff plan?

What is the difference between being debt-free and financially free?

Most business owners who end up in financial crisis did not get there because they failed to earn enough. They got there because nobody ever showed them how to keep what they earned. Revenue is not wealth, and that gap is where the real damage happens.

This week's guest on the podcast is Rachid Barry, and for 11 years he has helped entrepreneurs and high-income professionals build financial systems that reduce cash leakage, resolve IRS debt, and create real alternatives before bankruptcy ever becomes the only option. Rachid works with business owners across the U.S. who are profitable on paper but structurally exposed, and that is a story your audience knows well.

You can reach Rachid at RBarry@rjmconsultant.us.

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.

What are the known and hidden costs of getting sick?

What about a medical emergency?

Are you prepared for the cost of unexpected health issues and how can you protect yourself, your family, and your bank account?

On this week's episode of the Crushing Debt Podcast, Shawn & George talk about Shawn's son, who broke his arm recently, requiring surgery to fix. His son is expected to make a full recovery but the incident taught Shawn a few things about the costs of staying healthy and what to do when an accident happens, including known and hidden costs like:

• Emergency Room visit
• X-Rays and other tests
• IV
• Surgery
• Anethesia
• Pain medicine and pain management
• After-effects, like cancellation of future plans, medicinal needs after the fact, and other necessary care supplies.

We also talk about insurance coverages and how those play into the analysis, and what to do to mitigate the out of pocket costs of a medical incident.

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.

Are money problems spilling over to work?

What can you do for your employees to reduce stress? Reduce down time?

What can you do for employee retention?

What is a "stop for this" purchase?

As an employer, how can you reduce the chance that you get asked to give advances of payroll to employees?

In this week's episode of the Crushing Debt Podcast, Shawn & George talk to Barry Sanborn about the cost of employee turnover, and what to 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: 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

What are some of your more expensive habits?

What impact does summer have on your spending?

In this week's episode of the podcast, Shawn & George talk about summer's most expensive habits, including:

• Weddings / Vacations / Family Outings
• Summer Camps & Kids Activities
• Concerts
• Home Improvement Projects
• Pets
• Subscriptions
• Back to School Shopping
• Cost of Living Changes

What other summer spending habits do you have?

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 (until June 30, 2026) at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026

It is officially the start of Hurricane Season in Florida!

Are you prepared?

What are some funny hurricane truths? How much water should you have? Toilet paper? Flash lights and batteries?

How should you prepare your family and your business for the financial impact of a storm?

On this week's episode of The Crushing Debt Podcast, Shawn & George talk about these topics, including whether you are financially ready personally and professionally for a storm, what you need to know or do to protect your family and your business, all with our unique Crushing Debt spin!

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. The link will be open through the end of June!

Why do people think bankruptcy is bad?

True, it has a negative stigma and it will be a hit to your credit score, but why is bankruptcy perceived as a massive negative?

Is bankruptcy the best solution for everyone? Put simply, no it is not, but it is better than most people will admit.

On this week's episode of The Crushing Debt Podccast, Shawn and George talk about rising debt levels, rising gas prices, rising grocery prices ... prices increasing everywhere, and what that means for someone considering bankruptcy.

Plus what are some of the negatives of waiting too long to file? What is the difference between bankruptcy and negotiating the debt? What is the impact of the automatic stay? And what is life like after bankruptcy?

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 there is still time, until June 30, 2026 to donate to Pancreatic Cancer research and education by joining Shawn's 2026 PanCAN team at MY Legacy Striders: http://support.pancan.org/goto/MyLegacy2026