From Trade Work to Scalable Systems - Lessons from a 20-Year Operator

Описание: -In this episode of Next Level Operators, Jesse Spiegel sits down with Aaron Taddiken, founder of Taddiken Tree Company, to explore what actually drives long-term business durability.

Aaron spent over 20 years building one of Boulder’s most respected arborist companies before selling it. Along the way, he didn’t just scale a service business. He built teams, systems, and internal tools that allowed the company to grow without hollowing out the people doing the work.

This conversation is not about tactics in isolation. It’s about how values, culture, and technical rigor interact over decades, and why most operational problems are human problems before they are system problems.

They talk through Aaron’s path from hands-on tradesman to owner, system builder, and eventual software developer. The discussion also moves into his current work exploring AI, privacy, and locally controlled systems, and why he believes the next wave of tools will need to respect individual sovereignty rather than extract it.

Topics explored include:

-Building company culture without corporate theater
-Hiring for values instead of resumes
-Relationship-driven growth versus transactional scale
-Why most “process problems” are really people problems
-Designing systems that reduce repetition and friction
-When custom software makes sense and when it doesn’t
-Lessons from building internal tools before SaaS was fashionable
-How AI changes leverage, risk, and personal agency

This episode is for founders, operators, and advisors who care about building businesses that last, not just businesses that grow fast. If you’re thinking about how systems, people, and values actually intersect over time, you’ll find this conversation useful.