Table Saws, Psychological Safety, and Lessons from Building Two Startups and a Farm

Owen didn’t start out a believer. After 20 years in the industry, AI looked like the next hype cycle. Two years, two companies, and a berry farm later, some of that skepticism held up and some of it didn’t. This session is a retro on both: what worked, what didn’t, and which of the old rules still apply.

AI has changed how many organizations work. The boring reality is that much has stayed the same. This talk looks at both the failures and the wins of AI: Teams that went from six month builds to seven weeks; a startup Owen halted while it was succeeding; using AI as a “paralegal” to win a farm status appeal. Across two years of heavy AI use, the biggest gains came from the experience earned from years of managing healthy teams and processes, far more than a strong programming background. Psychological safety and honest critique aren’t optional. Unhealthy teams and practices don’t reveal problems or adjust to them, in the same way a poorly used LLM tells you a bug is fixed before it verifies.

This isn’t a meandering walk down memory lane. Owen will go through the specific processes and techniques he used to build new software and new companies. Each one, refined over 20 years, then reworked for AI. In many ways AI is a table saw introduced to a hand tool shop. Use it like the other tools, ignore it, or refuse to adjust your organization around it, and it will cost you dearly. Take the time to learn it deeply, trust your team, and you’ll be surprised what it can do and how much changes for the better.