Episode 5: Starting a Woodworking Business with $1,500 — Chandler Wakefield

In this episode of Small Business Strong, I sit down with Chandler Wakefield, founder of Wakefield Woodworking, to talk through the real path of building a professional woodworking business from the ground up—starting with just $1,500 in tools.Chandler shares how he got his start working alongside his father-in-law, learning the ropes of the trade the hard way and developing the skills, discipline, and standards required to make woodworking more than just a hobby. We talk about the early foundation that experience gave him, and how it shaped the way he approaches both craftsmanship and business today.Before woodworking, Chandler was on a very different path—planning to become a doctor, then moving into medical sales, and hitting a few bumps along the way. We talk honestly about those transitions, the uncertainty, and what it looks like to pivot without losing momentum.Now roughly five years in, Chandler is growing, reinvesting in new equipment, and aiming for $500,000 in revenue this year. This conversation is about patience, learning, reinvestment, and building something sustainable—one decision at a time.If you’re in the trades, considering a pivot, or trying to build a real business with your hands and your name on the line, this episode is for you.