Doug Whitewolff

4Trades.ai helps independent trades businesses — roofers, electricians, HVAC contractors, fence companies, and more — compete with larger companies through smart, affordable AI automation.

We specialize in three core areas: AI-powered phone voice agents that handle inbound phone calls so business owners never miss a lead, Custom CRM and automations that keeps jobs moving from first contact to final invoice, and workflow systems that eliminate the manual follow-ups and communication gaps that cost trades businesses time and money.

Our approach starts with understanding how your business actually operates. Through our GROUNDWORK consulting process, we map your workflows, identify bottlenecks, and implement automation that fits your team — not the other way around. Then our ongoing subscription services keep everything running reliably.

We believe independent contractors deserve the same operational tools that large companies take for granted, without the enterprise price tag or complexity. Measure twice, cut once — that's how we build systems too.

I spent 12 years teaching high school mathematics before transitioning into AI system development in 2023. That combination — breaking down complex problems into simple steps and building intelligent systems — is exactly what I bring to trades business owners today.

I studied AI at Carnegie Mellon back in 2001, two decades before the current boom, and hold two graduate degrees (Logic & Computation from CMU and one from from Portland State). I founded 4Trades.ai because I saw independent contractors struggling with the same operational problems that larger companies solve with expensive enterprise tools. My goal is to close that gap with smart, affordable automation.

When I'm not building systems for trades businesses, you'll find me on my Peloton (7,400+ lifetime miles), hiking somewhere in the Pacific Northwest, or strategizing over Pokémon cards with my kids. I live in an intergenerational household with my wife Beverly, and I believe in showing up with integrity in everything I do.

M.S. Logic & Computation, Carnegie Mellon University (AI and formal reasoning)

M.Ed. Advanced Mathematics, Portland State University

B.S. Mathematics & Philosophy, Portland State University

Carnegie Mellon Merit Scholarship (50% tuition)

Portland State Presidential Scholarship (full tuition)

Underrepresented Minority Achievement Scholarship, Portland State University