“Just because you’re not wearing a suit, doesn’t mean you’re not working.”

Aaron and I chat about how you don’t have to “look like a lawyer” to be one, and about his fascinating career path, which landed him at tech company Datadog, where he gets to work at a place that’s like “going to work in a spaceship.” Aaron began working as a DJ in his teens (kinda like the Beastie Boys!), later became a nightclub manager, and, during law school, interned at Atlantic Records—but later ended up in the tech world, courtesy of his background in intellectual property law. (Although, note, for you musicians out there, he does still provide legal advice to artists through his firm, ASF Legal Services.)

We talk about risk, and why it’s important to take it both in your life and in your career, and how understanding it as a concept can help you better advise your clients; why you should learn to “speak the language” of your industry; and finally how—no matter the industry—relationships are everything. Plus—how entertainment companies are not always the bad guy, and why creative people need support so they can continue to do the important work — of creating.

We also discuss how, to figure out the area of law in which you want to specialize, “be purposeful” in finding those people who are doing the work you want to do, in the industries in which you want to work. According to Aaron, even if it's cool to work with music artists, that shouldn’t be your only motivation…. Aaron also reminds us of some universal legal advice, a.k.a. what your parents likely told you growing up: everyone needs an attorney!

And, of course, where would we be without a drinking story? I’ll give you a hint: it involves a 90 year-old’s birthday party, chance encounters on an airplane’s first class cabin, and Cash Cash, a popular EDM band best known for their hit Take Me Home.

The music featured on this week's episode is “Entering the Bar Theme Music,” composed by Sam Carden for Entering the Bar®.