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The Essential Tax Podcast with Mishkin Santa, Episode 27

In this episode of The Essential Tax Podcast, Mishkin Santa welcomes back “frequent flyer” guest, Joshua Smeltzer. Joshua is a Tax and Corporate Lawyer at Gray Reed, a full-service Texas law firm with a comprehensive range of litigation and transactional practice groups. With 150 attorneys, they are equipped to support companies, and high-net-worth individuals and families, based in Texas or operating within its borders.

Tune in for these key takeaways:

* The challenging environment of cryptocurrency as it relates to tax compliance.

* The current regulatory environment — digital asset regulations in 2025, cryptocurrency compliance, and how these fit into the regulatory landscape

* The potential messiness of duplicated reporting and outdated IRS systems—topics that every tax professional should be aware of.

* Executive orders that complicate the regulatory framework, such as the one from January 31st, mandating the removal of ten regulations for every new one introduced

* The controversial role of lobbying in determining which regulations should be preserved or repealed—a reality highlighting the intricate layers involved in tax policy formation

* High-profile criminal cases involving cryptocurrency, including the case of "Bitcoin Jesus" and the implications for tax advisors

* The critical role of thorough tax advice and warnings of the potential pitfalls of non-compliance, even in cases of simple errors like failing to check a box indicating cryptocurrency activity

* Joshua’s optimistic vision for the future of blockchain and digital assets contingent on the establishment of stable coin regulations

* The importance of staying informed and proactive in navigating tax obligations, especially amidst an unpredictable regulatory environment

Learn more about Joshua Smeltzer:

* Connect with Joshua on LinkedIn: https://www.linkedin.com/in/joshua-smeltzer-bb07714

* Follow Gray Reed on LinkedIn: https://www.linkedin.com/company/grayreed

* Read Joshua’s bio on GrayReed.com: https://www.grayreed.com/Our-People/Joshua-D-Smeltzer

* Follow Joshua on X: https://x.com/JDSmeltzer

* Email: jsmeltzer@grayreed.com

Further resources:

* Previous Podcast with Joshua Smeltzer: https://podcasts.apple.com/us/podcast/irs-regulations-loper-bright-and-private-letter/id1754660944?i=1000677344463

* Joshua Smeltzer Forbes Articles:

** https://www.forbes.com/sites/joshuasmeltzer

** https://www.forbes.com/sites/joshuasmeltzer/2024/12/27/irs-targets-front-end-services-in-defi-reporting-final-regulations

** https://www.forbes.com/sites/joshuasmeltzer/2024/12/30/blockchain-advocates-file-suit-challenging-irs-defi-regulations

** https://www.forbes.com/sites/joshuasmeltzer/2025/01/27/bitcoin-jesus--maryland-lawyer-high-profile-cryptocurrency-tax-cases

* IRS Form 1099-DA: https://www.irs.gov/pub/irs-dft/f1099da--dft.pdf

* Executive Order on Regulations: https://www.whitehouse.gov/presidential-actions/2025/01/unleashing-prosperity-through-deregulation

* Executive Order on Government Staffing: https://www.whitehouse.gov/presidential-actions/2025/02/implementing-the-presidents-department-of-government-efficiency-cost-efficiency-initiative

* February 26th, 2025 Markup by House Ways and Means Committee: https://waysandmeans.house.gov/wp-content/uploads/2025/02/H.J.Res_.-25-Text.pdf

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Watch or listen to more episodes of The Essential Tax Podcast:

* https://www.youtube.com/@TheWolfGroupPC

* Apple: https://podcasts.apple.com/us/podcast/the-essential-tax-podcast/id1754660944

* Spotify: https://open.spotify.com/show/2beZfOpwfBlBgWHlNelAOf

Connect and learn more from your host, Mishkin Santa:

* Connect with Mishkin on LinkedIn: https://www.linkedin.com/in/msanta

* Follow The Wolf Group, P.C. on LinkedIn: https://www.linkedin.com/company/the-wolf-group-pc

* Read Mishkin’s bio on Wolf Group, P.C.’s website: https://thewolfgroup.com/our-people/mishkin-santa