The Entrepreneur's Guide To More Free Time - Episode 485
Release Date: 10/16/2025
IRS Wins Again? - Episode 490
Crushing Debt Podcast
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...
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FORE! Ways Golf Can Teach You About Debt! - Episode 489
Crushing Debt Podcast
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...
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Who's More In Debt, You or Your Landlord - Episode 488
Crushing Debt Podcast
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 - You can reach Mark at or ., or 727-738-RENT (7368). Let us know if you enjoy this episode and, if so, please share it with your friends, like and...
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Financial Vampires - Episode 487
Crushing Debt Podcast
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...
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Mom, Dad & My Credit Card Bill! - Episode 486
Crushing Debt Podcast
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...
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The Entrepreneur's Guide To More Free Time - Episode 485
Crushing Debt Podcast
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...
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The Real Reason Businesses Fail - Episode 484
Crushing Debt Podcast
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 (). 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...
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Student Loan Solutions & Discharges - Episode 483
Crushing Debt Podcast
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...
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What if I Can't Afford To Pay For My Kids' College? - Episode 482
Crushing Debt Podcast
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: To...
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Building Financial Literacy for Vulnerable Communities - Episode 481
Crushing Debt Podcast
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 financially literate, and how can we help people make that shift? In this week's episode, Shawn interviews Michelle Campbell, the author of Bluebird, a memoir that candidly explores themes of trauma,...
info_outlineWhen 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