AI is not a pilot program you park next to the real business. It is either wired into strategy, budget, and accountability — or it is theater with a demo attached.
Read moreOperating
Say no more often than you say yes. Protect long uninterrupted blocks for deep work. Everything else in a portfolio of businesses is downstream of that discipline.
August 4, 2026 · 5 min
Capital
ATMs and vending machines will never trend. They also never ask for a Series B. A note on unsexy assets and the freedom they buy.
July 21, 2026 · 6 min
Rotates daily · One of Sean’s ventures
Insurance
Veteran-owned independent brokerage writing life (including IUL), with expert advice and referrals across property, casualty, and health.
22+
Years across federal programs, security, and ownership
15+
Businesses and affiliates operating today
20+
Years of service in the U.S. Army Reserve
9
Collegiate degrees
15+
Professional certifications & licenses
Direct access
Meetings, consults, board seats, and keynotes. Tell me the intent and what you are trying to decide — I answer my own inbox.
Keynote
Keynotes & Panels
Talks on AI as business strategy, cyber risk for boards, and building a portfolio while holding a day job.
Advisory
Strategic Consult
A working session on the decision in front of you — growth, compliance, capital, or a hire you cannot undo.
Meeting
Intro Conversation
Thirty minutes, no deck. Partnerships, deals, and the occasional favor for someone building something real.
Next generation
My daughter Evelyn is already creating, writing, and building online. Visit her site and follow along — the next chapter is hers.
Visit evelyn-chao.com