Jake Nickell is the CEO and founder of Threadless, the nexus of a diverse and expansive artist community that partners with those artists to promote and produce their art. In 2000, Threadless began as a t-shirt design company based in Chicago. Since then, Threadless has grown into a fully remote company with a marketplace of full apparel, accessories, and home decor powered by their artist community. In lifting up the creative expression of their artists, Threadless was an early innovator in the new digital economy, showing the world that business can support art, for the benefit of everyone involved. Today, Threadless hosts over 2 million users and continues to evolve— staying true to their mission of giving the creative minds of the world more opportunities to make and sell great art. Throughout this conversation we discuss flow, simplifying problems to find solutions, stepping back to re-establish your relationship to work, infusing your identity into what you’re making, and the differing energies of making and managing. Wherever you’re at in your own journey— just starting out, taking a step back, or feeling the growing pains of expansion, there’s so much gold here in this conversation and we’re stoked to share it with you.