If you were to look at Jen Vescio’s calendar, it might look like a pack of Skittles: Every single one of her meetings is color-coded according to the Insights Color Focus system, which assigns the colors red, blue, yellow, and green based on what methods they emphasize in their work. As the chief business development officer of Uber, Jen has to work with people across that spectrum, and preps for each meeting accordingly.

In this episode, Jen and Joubin discuss the pros and cons of media training, Malcolm Gladwell’s Outliers, “semi-pro” soccer, how to ruin your Uber rating, the “fluorescent light” journey, working at “it” companies before they were disrupted, the art and science of business development, self-awareness vs. understanding others, Sean Bratches, what is your motive?, side letter PTSD, “speed and silence are your two worst enemies,” forced time off, getting buy-in, and why “Uber is wired for trauma.”

In this episode, we cover:

* “Dancing in the moment” (00:54)
* The Olympic Development Program (03:22)
* Jen’s parents (08:15)
* DJing and music in Ubers (10:40)
* Talking to Uber drivers (12:48)
* Retiring from soccer (15:04)
* “The big transition” (17:22)
* The dotcom boom and Jen’s first jobs (20:04)
* Innovation and disruption (22:15)
* Buy, build, or partner (27:24)
* Understanding the “color” of others (35:27)
* How to talk to a “double red” (38:38)
* Insights Color Focus and the color of companies (41:16)
* The Trust Quotient (46:45)
* The biggest deal Jen has brokered (50:17)
* The pressure of big deals (51:46)
* The $350 million deal she botched (55:14)
* Getting burned out on corporate jobs (58:22)
* Big, shiny brands like Uber (01:00:38)
* Mental contracts and taking time off (01:05:07)
* Tough feedback (01:08:24)
* Developing trust internally vs. externally (01:09:48)
* How COVID impacted Uber (01:13:08)
* Where Uber is hiring and what Jen thinks of when she hears the word “Grit” (01:18:16)