How Tax Works
Episodes
Theft, Scam, and Casualty Losses
27 Apr 2026
Contributed by Lukas
In episode 51 of How Tax Works, Matt Foreman discusses theft losses under section1 165 of the IRC, including pig butchering, rug pulls, and Ponzi sche...
Ferraris, Montana LLCs, and Use Taxes
13 Apr 2026
Contributed by Lukas
In episode 50 of How Tax Works, Matt Foreman discusses Al Capone, bad tax advice from the internet, and a sports car, which is a mixture of that led t...
Hobby Losses and How They Are Limited
30 Mar 2026
Contributed by Lukas
In episode 49 of How Tax Works, Matt Foreman discusses hobby losses, which are a significant and often underappreciated limitation on the ability to d...
Unrelated Business Taxable Income
16 Mar 2026
Contributed by Lukas
In episode 48 of How Tax Works, Matt Foreman discusses Unrelated Business Taxable Income (UBTI), which is what can happen when nonprofit entities earn...
Substance Versus Form, Part II: The Step Transaction Doctrine
02 Mar 2026
Contributed by Lukas
In episode 47 of How Tax Works, Matt Foreman continues his discussion of substance versus form issues, focusing on the Step Transaction Doctrine, di...
Substance Versus Form, Part I: The Economic Substance Doctrine
16 Feb 2026
Contributed by Lukas
In episode 46 of How Tax Works, Matt Foreman begins his discussion of substance versus form issues, beginning with the Economic Substance Doctrine, fr...
Stock Sales Taxed as Asset Sales
02 Feb 2026
Contributed by Lukas
In episode 45 of How Tax Works, Matt Foreman discusses how to have stock sales taxed as asset sales by using F Reorganizations, selling wholly-owned s...
Common Mistakes and Misconceptions Regarding Qualified Small Business Stock (QSBS) under section 1202
20 Jan 2026
Contributed by Lukas
In episode 44 of How Tax Works, Matt Foreman discusses common mistakes, misconceptions, and missteps involving qualified small business stock (QSBS) u...
Allocations under IRC 704(c)
05 Jan 2026
Contributed by Lukas
In episode 43 of How Tax Works, Matt Foreman discusses the three allowable methods Traditional, Traditional with Curative Allocations, and Remedial; t...
Offers in Compromise (OIC)
22 Dec 2025
Contributed by Lukas
In episode 42 of How Tax Works, Matt Foreman discusses the often misunderstood Offer in Compromise process, focusing on what types of OICs are likely ...
Payment Plans and Penalty Abatement
01 Dec 2025
Contributed by Lukas
In episode 41 of How Tax Works, Matt Foreman gives an overview of what taxpayers and their advisors should do and expect when they owe money and want ...
What You Should Do If Your Audit Goes Poorly and You Need to Litigate?
24 Nov 2025
Contributed by Lukas
In episode 40 of How Tax Works, Matt Foreman continues his discussion of tax controversy, discussing appeals and litigation, focusing on timing, audit...
What Should You Do If You Get Audited by the IRS (or State Revenue Agency)?
10 Nov 2025
Contributed by Lukas
In episode 39 of How Tax Works, Matt Foreman discusses what you should do if you get audited, including discussing the process of an audit, how to pol...
Updates to Qualified Small Business Stock and R&E Expensing Under OBBBA
27 Oct 2025
Contributed by Lukas
In episode 38 of How Tax Works, Matt Foreman discusses the updates and modifications to Qualified Small Business Stock (IRC 1202) and R&E Expensin...
If You Win the Lottery, the First Thing You Should Do Is… Call a Tax Lawyer?
14 Oct 2025
Contributed by Lukas
In episode 37 of How Tax Works, Matt Foreman discusses the various tax things you should consider when you win the lottery, right after you throw a pa...
Grouping and Separate Activities Under Section 469 of the Internal Revenue Code
29 Sep 2025
Contributed by Lukas
In episode 36 of How Tax Works, Matt Foreman discusses grouping elections for the passive activity loss limitations, which are also generally applicab...
The Installment Method Under Section 453 of Internal Revenue Code
15 Sep 2025
Contributed by Lukas
In episode 35 of How Tax Works, Matt Foreman discusses sales where payment is over a number of years, with additional discussions of interest payments...
Can AI Replace Tax Lawyers? (Part II)
02 Sep 2025
Contributed by Lukas
In episode 34 of How Tax Works, Matt Foreman continues his evaluation of human and AI answers to a less straightforward tax question, seeking to (hope...
Can AI Replace Tax Lawyers? (Part I)
02 Sep 2025
Contributed by Lukas
In episode 33 of How Tax Works, Matt Foreman evaluates human and AI answers to a straightforward tax question, seeking to (somewhat) answer the questi...
How I Think the ESPN and NFL Deal is Structured
18 Aug 2025
Contributed by Lukas
In episode 32 of How Tax Works, Matt Foreman discusses the tax structure of the recently announced deal where the NFL is exchanging NFL Network and Re...
Real Estate Investors and the Passive Activity Loss Rules under IRC 469
04 Aug 2025
Contributed by Lukas
In Episode 31 of How Tax Works, Matt Foreman revisits the passive activity loss limitation rules that he discussed in Episode 13—but from the view o...
Famous and Important Tax Cases: Part II
21 Jul 2025
Contributed by Lukas
In episode 30 of How Tax Works, Matt Foreman continues his discussion of important and relevant tax cases, discussing gambling losses, whether somethi...
Famous and Important Tax Cases: Part I
07 Jul 2025
Contributed by Lukas
In episode 29 of How Tax Works, Matt Foreman discusses important and relevant tax cases, noting that there might be a patriotic duty to pay your taxes...
Family Offices
23 Jun 2025
Contributed by Lukas
In Episode 28 of How Tax Works, Matt Foreman discusses Family Offices, focusing on purpose, structure, and why they’re the perfect solution for book...
F Reorgs Redux
09 Jun 2025
Contributed by Lukas
In episode 27 of How Tax Works, Matt Foreman discusses what to do when you’ve made a S election and might have some remorse, need to restructure, or...
ABCs of A, B, and C Reorganizations
27 May 2025
Contributed by Lukas
In episode 26 of How Tax Works, Matt Foreman discusses how to ensure mergers and acquisitions are tax-free, why it’s not always best to squeeze into...
Partnership Divisions
12 May 2025
Contributed by Lukas
In Episode 25 of How Tax Works, Matt Foreman discusses the tax implications of dividing partnerships, redeeming partners, and dealing with partnership...
Divisive Reorganizations
28 Apr 2025
Contributed by Lukas
In Episode 24 of How Tax Works, Matt Foreman discusses how to divide two businesses into separate entities, focusing on the legal requirements and bes...
What the F is an F Reorg?
14 Apr 2025
Contributed by Lukas
In Episode 23 of How Tax Works, Matt Foreman discusses the five W’s of F Reorgs: Who needs one, What they do (and don’t do), When they’re necess...
Golden Parachutes
31 Mar 2025
Contributed by Lukas
In Episode 22 of How Tax Works, Matt Foreman discusses Golden Parachutes under section 280G, which may sound like a fun thing to have, but they likely...
Why Foreign Persons Probably Shouldn’t Own LLCs
17 Mar 2025
Contributed by Lukas
In Episode 21 of How Tax Works, Matt Foreman discusses why foreign persons almost certainly shouldn’t own LLCs, a surprisingly common issue.How Tax ...
Why, for Tax Reasons, You Should Buy a Professional Sports Team
03 Mar 2025
Contributed by Lukas
In Episode 20 of How Tax Works, Matt Foreman discusses the pros and cons of buying a professional sports team from a tax perspective. Listen for a dis...
Qualified Small Business Stock (IRC 1202): Part III
17 Feb 2025
Contributed by Lukas
In Episode 19 of How Tax Works, Matt Foreman concludes his discussion of Qualified Small Business Stock (QSBS), which is section 1202 of the Internal ...
Qualified Small Business Stock (IRC 1202): Part II
03 Feb 2025
Contributed by Lukas
In Episode 18 of How Tax Works, Matt Foreman continues his discussion of Qualified Small Business Stock (QSBS), section 1202 of the Internal Revenue C...
Qualified Small Business Stock (IRC 1202): Part I
21 Jan 2025
Contributed by Lukas
In Episode 17 of How Tax Works, Matt Foreman talks about Qualified Small Business Stock (QSBS), which is section 1202 of the Internal Revenue Code. ...
Questions People Ask Tax Lawyers at Weddings
06 Jan 2025
Contributed by Lukas
In episode 16 of How Tax Works, Matt Foreman talks about how to lower your taxes and why your accountant probably shouldn’t let you deduct your Buga...
Tax Issues with Divorce
16 Dec 2024
Contributed by Lukas
In episode 15 of How Tax Works, Matt Foreman discusses tax issues with divorce, from transfer between spouses, to splitting up businesses and the need...
At Risk Limitations under IRC 465
09 Dec 2024
Contributed by Lukas
In episode 14 of How Tax Works, Matt Foreman discusses another signature change from the Tax Reform Act of 1986, section 465, which often prevents ded...
Passive Activity Losses and Credit Limitations under IRC 469
25 Nov 2024
Contributed by Lukas
In episode 13 of How Tax Works, Matt Foreman discusses one of the signature changes from the Tax Reform Act of 1986, section 469, which often prevents...
Self-employment Tax on Partners, Net Investment Income Tax, and Soroban Capital Partners LP v. Comm’r (Part II)
12 Nov 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman continues his discussion of self-employment taxes, the ongoing tax saga of a hedge fund’s partne...
Self-employment Tax on Partners, Net Investment Income Tax, and Soroban Capital Partners LP v. Comm’r (Part I)
28 Oct 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses self-employment taxes, the ongoing tax saga of a hedge fund’s partners trying to convi...
Tax Consequences of Forming, Selling, and Dissolving Partnerships and Disregarded Entities (Rev. Ruls. 99-5 and 99-6)
15 Oct 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses the tax consequences of going from a disregarded entity to a partnership (Rev. Rul. 99-5...
Various State and Local Income Tax Issues
30 Sep 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses a variety of state and local income tax issues that commonly come up during sales/purcha...
Convertible Debt and SAFEs
16 Sep 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses the tax consequences of Convertible Debt and Simple Agreements for Future Equity (SAFE)....
Profits Interests, Promotes, and How to Structure Equity-based Compensation
03 Sep 2024
Contributed by Lukas
In a quasi-continuation of episode 6 of How Tax Works, host Matt Foreman discusses the most misunderstood and misapplied form of equity grants: Profit...
Equity-based Compensation and 83(b) Elections
19 Aug 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses the tax consequences of equity compensation, including stock options (ISOs and NSOs), St...
Ordinary & Necessary Business Expenses: Examples and What Not to Do
05 Aug 2024
Contributed by Lukas
In a continuation of episode 4, in this episode of How Tax Works, host Matt Foreman gives examples of what you can deduct as a business expense, inclu...
Ordinary & Necessary Business Expenses: IRC 162 and 212
22 Jul 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses what you can deduct as business expenses, giving an overview of the law, regulations, an...
Residency
08 Jul 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses state residency rules to determine where an individual is a resident for income tax purp...
Sales and Use Tax
24 Jun 2024
Contributed by Lukas
In this episode of How Tax Works, host Matt Foreman discusses Sales and Use Taxes. Matt will define sales taxes and use taxes; describe the common a...
Entity Selection
10 Jun 2024
Contributed by Lukas
Welcome to the first episode of How Tax Works. Host Matt Foreman discusses what is likely the most important decision that a business owner can make: ...