IRS Wins Again? - Episode 490 episode artwork

EPISODE · Nov 20, 2025 · 45 MIN

IRS Wins Again? - Episode 490

from Crushing Debt · host Shawn Yesner & George Curbelo

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 

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IRS Wins Again? - Episode 490

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