Episode 18 - Roots v. Commissioner

Episode 21 - How We Got the Income Tax

From Articles of Confederation to the Constitutional Amendment - how the US ended up with a permanent income tax is a wild ride. In this episode, we run through how the US was originally funded with tariffs, what that did to divide the country, and the iterations of the income tax before arriving at what we have today.

Episode 20 - Youngs v. Commissioner

What happens when you run a ranch at a loss for 14 years and use it against your profitable S-Corp? Sometimes, you get caught. We run through the 9 factor test used by the courts to determine if your weekend getaway qualifies as legitimate business expenses or an expensive hobby! Check out the Plug on YouTube for the video!

Episode 19 - Hadar v. NY Appeals

A BIG win for taxpayers who deferred $30 million(!!!) in gain on real estate via a Tenancy in Common (TIC). We get into what is a 1031, what is a TIC, and why I think this is one of the coolest cases I've done an episode on. Enjoy!

Episode 18 - Roots v. Commissioner

$3 million for a lodge that has bats and mice living in the walls. Another $4 million to sue the builder and architect who built it all. And all the taxpayer gets in the end is lost deductions and a 20% penalty which could have been avoided. Today is all about classifying streams of income - passive, active, or capital - and how that can seriously change your tax owed. Enjoy.

Episode 17 - History of US Income Tax [Special Edition]

How did we get here? You can learn all the strategy tips you want, but how did our current framework come into existence? Over the last 150 years of our country, layers of tax law and reform have passed. In this episode, we take a broad overview of the major pieces of tax reform - through the lens of small business and their owners. From our country's first income tax in 1861, to repeal, to constitutional amendment all the way to Trump 1.0 and 2.0. Hope you enjoy it.