Going into business with your best friend sounds like a dream—but how do you protect the friendship when work, stress, and different expectations get involved?

This week on The Art of Classiness, Robin and Deborah are celebrating 100 episodes—and the fact that they are still friends. They share what building a podcast together has taught them about boundaries, honest communication, creative disagreements, and putting friendship first.

In this special anniversary episode, they go back to the beginning: what they thought they were creating, what they completely underestimated, and the “classiest blunders” they can finally laugh about now. They also unpack the friendship-first principles that have helped them keep going: dream big, protect mental health, stop keeping score, say the hard thing while it is still small, and assume good intent.

It’s an honest, funny look at building something with a friend—and making sure the friendship has room to grow alongside it.

Here’s to 100 episodes. Here’s to still being friends. And here’s to 100 more.

Connect with us on Instagram and TikTok: @artofclassiness
Share your favorite AOC moment—or what you want from the next 100 episodes: artofclassiness@gmail.com

Quick disclaimer, friends—we are not business coaches, therapists, or relationship professionals. We are two friends sharing what has worked for us while building something together. This episode is for fun and informational purposes only. Take care of yourselves, communicate clearly, and use what feels right for you.