Entrepreneurship is an odyssey with many unexpected stops on the journey. You could find yourself on a loading dock in East LA, freestyle rapping with a man known as DJ Trucker—yes, there is video proof.

In this episode of our special series, Killing It, hosts Jason Henrichs and Alex Johnson talk with Max Farrell. Max started his career in business development at Dwolla and went on to found WorkHound, which is now WorkStep. WorkHound began when Max stumbled upon a problem in an industry he didn’t come from, and he jumped right in.

The trio speaks candidly about the unpredictable nature of the founder journey and the need to deeply understand the customer. This includes Max spending 48 consecutive hours in the cab of a truck, winning a Truck Tank pitch competition, and recognizing when it is time to personally hit the road and move on.

This honest conversation shares the ups and downs of building a business. Max describes the near-failures, the acquisition, and his eventual decision to leave his founder identity behind. It’s an odyssey.