Guest: Robert Chatwani, President and General Manager of Growth at DocuSign

Robert Chatwani’s first reinvention was in his early 20s, when he left McKinsey & Company to start a people-powered commerce startup called MonkeyBin. And in the ensuing decades, his entrepreneurial energy hasn’t slowed down, with hops to eBay, Spring, Atlassian, and now DocuSign, where he is the President and General Manager of Growth. He cites a “healthy anxiety” that comes from getting too comfortable in any role, where he finds himself solving the same problems over and over again; but when you’re in a little bit over your head, Robert explains, “that’s a good place to be, because that’s where the best learning comes from.”

In this episode, Robert and Joubin discuss trusting your intuition, reinventing yourself, personal boards of advisors, people-powered commerce, betting on people, career coaching, taking time for family, being the same person in every room, bone marrow donors, energy takers vs. creators, and leading with empathy.

In this episode, we cover:

• Networking through venture capitalists (02:18)
• Leaving high-profile jobs (04:29)
• How to know when it’s time to leave (07:55)
• 12 years at eBay (11:05)
• The seeds of doubt (15:10)
• Finding purpose in company-building (17:51)
• Robert’s personal mission statement (21:01)
• Growing up in Chicago and his parents (24:40)
• Losing a parent (27:16)
• True North by Bill George (29:35)
• Finding ways to be human (32:45)
• What accomplishment Robert is most proud of (34:35)
• MonkeyBin and meeting eBay (36:08)
• Sameer Bhatia’s battle with leukemia (38:30)
• Building a global bone marrow campaign (42:38)
• “You can’t control every outcome” (48:07)
• Unexpected side effects (52:56)
• Business is a force for good (56:26)
• Working at Spring, and then Atlassian (01:00:01)
• Self-doubt and leaving Atlassian (01:06:29)
• Making tough calls with IQ & EQ (01:10:24)
• Who DocuSign is hiring, and what “grit” means to Robert (01:13:48)

Links:

• Connect with Robert
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm