The Banker Who Quit His Career to Build a Creative Agency

What if the detours were the plan all along? We sit down with Matt Woolley—husband, father, guitarist, and founder of Designsteins—to unpack how a life threaded through banking, music, and marketing turned into a 16-year agency serving major retail brands. From small-town Arkansas to big-box shelves, Matt shares how the recession taught him to respect cash flow, why mom-and-pop projects sharpened his packaging and display chops, and how every cent counts when you’re designing for Walmart-scale sell-through.

The turning points are raw and real. Matt opens up about leaving banking without a degree, learning the business from the ground up, and the hard days when two retainer clients disappeared a month apart near the holidays. A quiet inner nudge to change a workout time leads to a locker room run-in with a long-time prospect, a next-day meeting, and a new business lane. It’s not a fairy tale; it’s a masterclass in staying moving, listening for prompts, and letting hope compound. We dig into faith as a stabilizer, the myth of the self-made founder, and how humanity—mentors, smiles, and simple encouragement—often restores momentum faster than playbooks.

We also talk shop. Matt explains why “concept to cart” is more than a tagline, how to stretch corrugate and simplify structures for assembly speed, and the retail essentials of packaging, displays, 3D visuals, and dot-com content that actually sells. He shares why mentorship beats pride, how to speak a bank’s language when you need capital, and the true metric of success: staying in business. Finally, we explore his podcast, where he archives real operator wisdom and keeps the focus on useful stories over empty influence.

If you’re scaling a brand, pitching a supplier, or simply trying to find your next foothold, this conversation delivers practical tactics and grounded encouragement. Subscribe, share this with a founder who needs a lift, and leave a review with your biggest takeaway—we read every one.