Unfulfilled by his entry-level jobs at Apple and Square, Robinson struck out on his own a year ago to start Vnylst, an app that connects record collectors and merchants.
Self-Assessment: "I'm at a self-funded startup in L.A. We have three full-time people: one in Brazil and two in San Francisco. Between pitching to angels, working with partners, and developing a prototype from scratch—something I've never done before—I have to keep the staff feeling like they're doing something important. Leading people in a virtual team is a competency that I would like to build upon, but I have no idea how. It's hard to communicate, 'Hey, put this fire under you and get to work' by text, email,
Starting this company has given me a reason to ask for help. I'm seeking the personal investment of people who have my interests in mind, who know more than me, and who can push me where I need to be pushed. This is rarer than you think. Mostly mentorship is just the occasional beer without much focus. You have to find people who believe in you and give them a reason to weigh in."
DDI Assessment: Osandi has already mastered what a lot of people at the highest levels never achieve: He has cultivated the habit of building a support network and tapping it for useful feedback, perhaps the most powerful indicator of sustained success. But his transition brings up a classic emerging-leader challenge: The habits that got you here are not enough to move you forward. Osandi's network can advise and guide, but it can't lead for him. His concerns about his virtual team are only part of the bigger issue. He needs to reorient his thinking from advisee to leader.
ROBINSON'S RESPONSE: "The closer we get to launch, the better I get at instilling a sense of urgency. I am planning some in-person visits this fall, to better build the Jell-O between everybody."
*DDI surveys conducted in 2010 and 2011
A version of this article appeared in the December 2012/January 2013 issue of Fast Company magazine.