Crushing Debt

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 trac...

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, includ...

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...

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...

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 Adjustm...

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...

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 Ad...

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 provi...

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)...

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...

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 Vamp...

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...

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, Tiffani...

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 s...

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 pra...

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...

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 financ...

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...

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 e...

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 G...

Would you give money to friends and family members?  Would you loan money to them? Are you "too nice" with your money? What happens when you're out to dinner with a group of friends and the bill comes, but most of them were drinking and you were not?  Or you had the steak and one of your friends had chicken.  Or you ordered dessert with your dinner and no one else did?  How do you split the bill,...

"Two bankruptcy attorneys go on a podcast to talk about debt!" Sounds like a set up to a bad joke. On this week's episode of the Crushing Debt Podcast, Shawn & George talk to bankruptcy attorney Barry Levine, a graduate of New England Law | Boston (formerly the New England School of Law). Mr. Levine has acted as outside counsel to a number of small businesses in a variety of endeavors along with i...

How do you talk to your kids about stress? How do you talk to your kids about debt? In today's episode of the Crushing Debt Podcast, Shawn & George talk to Iuri Melo, the co-founder of School Pulse, a company dedicated to helping students and parents tackle real challenges - financial, emotional and beyond. Building on last week's episode, we focus on: Stress prevention and proactive prevention Pr...

Are kids today financially soft? Or are they navigating a nightmare economy with style? In today's episode, in addition to yelling "Get Off My Lawn!" Shawn & George talk about who had it tougher - their generation, previous generations, or the younger generations. Boomers vs. Zoomers: Who Had It Tougher? Social Media Pressure and Lifestyle Creep Financial Education: Still Optional, Still a Problem...

Why did George become a financial coach?  What is his "Why?" What lessons has George learned in his 48 years on Planet Earth? Revenge is sweet! Episode 351 was George interviewing Shawn about his birthday, what he's learned in his years, why he became an attorney and how he formed Yesner Law. Today's episode is Shawn's revenge on George's birthday (July 20, 1977). Let us know if you enjoy this epi...