In this episode of The Talent Track Podcast, Oliver Feakins sits down with Jordan Tallman of Wayward Staffing for a raw, unfiltered conversation about building a modern staffing agency from the ground up.

Jordan shares his journey from working out of a garage in IT staffing to launching Wayward during COVID and now scaling with a bold goal of hitting $100M by 2030. But this isn’t a highlight reel—it’s a deep dive into the real challenges of entrepreneurship in travel healthcare staffing.

Together, Oliver and Jordan unpack what most agencies are still getting wrong: transactional recruiting, broken communication between recruiters and nurses, and the growing gap between automation and true relationship-driven staffing. Jordan breaks down his “radical candor” approach with both travelers and facilities, and why honesty—not hacks—is what actually builds long-term success.

They also dig into the messy reality of growth: hiring missteps, losing a major MSP relationship overnight, rebuilding from near-zero cash flow, and the brutal lesson of scaling too fast without the recruiting engine to support it.

On the flip side, they explore what’s working—agile small agencies, high-touch recruiter relationships, smart use of job boards like TNS, and why smaller teams can outmaneuver the giants when they lean into speed, grit, and authenticity.

If you’re in healthcare staffing, recruiting, or building anything in a competitive marketplace, this episode is a candid look at what it really takes to survive—and win.