09/04/2026
Toby Woodiwiss has spent two decades turning what started as a side hustle into a values-driven company he now runs with an entrepreneurship degree and MBA behind it.
In this episode, Toby, founder of Woodiwiss Painting in the East Bay who quit knocking on doors in an area where he had zero connections, reveals the hiring philosophy that built an all W-2 team in one of the toughest labor states in the country, and why he'd rather develop imperfect people than chase a shiny hire who doesn't exist.
You'll discover:
✅ The three values that predict whether a new hire will thrive: heart of service, embracing growth, and taking ownership of the hard stuff
✅ Why the interview question about what would have made you stay at your last job reveals what actually drives someone
✅ How outgrowing the "hire your friends and family" phase opens the door to talent that's truly committed to doing the job right
✅ The uncomfortable truth that most business owners believe they lack the resources to grow their people, when the real resource is simply time and attention
Your employees are your greatest resource, and developing them may take years, but that's the job.
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