Aug 6, 2026 · 43 min · 13 segments
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…
Max FarrellGuest
Jason HenrichsHost
Alex JohnsonHost
[upbeat music] Entrepreneurship is an odyssey with many unexpected stops on the journey.
For example, you may find yourself in East LA loading dock, freestyle rapping with a man known as the DJ Trucker.
In this episode of Killing It, Alex and I talk with Max Farrell, who started his career in business development in Dwolla and went on to found Workhound.
We talk about understanding the customer journey by literally spending forty-eight consecutive hours with them, how hard it is to cash a giant check when you win a pitch competition, and discussing whether it's time to give up over 40s and catfish when your first potential customer ghosts you after you traveled multiple states for the meeting.
Max lived the entire arc, building something that almost died repeatedly, watching it get absorbed into something bigger, staying inside as an employee, and then choosing to walk away from the identity as the founder entirely.
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[upbeat music] Entrepreneurship is an odyssey with many unexpected stops on the journey.
For example, you may find yourself in East LA loading dock, freestyle rapping with a man known as the DJ Trucker.
In this episode of Killing It, Alex and I talk with Max Farrell, who started his career in business development in Dwolla and went on to found Workhound.
We talk about understanding the customer journey by literally spending forty-eight consecutive hours with them, how hard it is to cash a giant check when you win a pitch competition, and discussing whether it's time to give up over 40s and catfish when your first potential customer ghosts you after you traveled multiple states for the meeting.
Max lived the entire arc, building something that almost died repeatedly, watching it get absorbed into something bigger, staying inside as an employee, and then choosing to walk away from the identity as the founder entirely.
