Beautiful & Powerful Leadership Lessons From A Serial Social Entrepreneur, with Jennifer Anastasoff

This conversation was such a delight for me! I got to talk with a friend I’ve known for 20 years, from back in our graduate school days at the Kennedy School — Jennifer Anastasoff. Jennifer is a serial entrepreneur who has spent the past two decades identifying gaps, breakdowns, and inefficiencies in our social systems, and responding by building real, lasting solutions.

Her superpower is bringing together incredible talent – building high functioning, high-impact teams that work together to solve real social problems.

She was a founding member of U.S. Digital Service at the White House and served as Head of People from 2014 until 2017, helping to create a diverse, cross-functional pipeline of digital talent from around America into our federal government.  She also served as founding CEO of Fuse Corps, as well as founder and CEO of multiple other social enterprises focused on bringing technical and operational skills to the public sector.

Because she has founded and grown so many organizations, I wanted to talk with Jennifer about life lessons.  That’s what this conversation is – and I love it! Jennifer is just so great at sensemaking – looking at the times an initiative or organization has not worked out the way she planned, and translating those failures into fuel for future experiments; looking at the times she’s gone farther than she imagined – an initiative has surpassed the impact shed dreamed – and culling those lessons as fuel as well.

Jennifer is one of those people who clears a new path through the brush. She is the person who inspired my own social entrepreneurship back in my early, early 20s, and I’m thrilled to have her share some of her inspiration on this show.