Bo Bennett
He convinced businesses they needed a website in 1995. He’s doing it again — founder of PrivateChief, the AI chief of staff for your household.
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Conversations Bo is ready to have
The Second 1995
In 1995, business owners asked Bo why they would ever need a website. This year, people ask him why a family would ever need an AI agent — often from the same chair. How to tell a genuine inflection point from hype, from someone standing on his second one.
The Smart Home That Defeated Its Own Family
Thirty years of programming, a dozen apps, a dozen logins — and the man who built the system could operate about sixty percent of his own house. Why the problem was never the devices, and what changed when the household got one member of staff who speaks all their languages.
Chatbots Talk. Agents Do.
Bo was as impressed by ChatGPT as anyone — until he noticed it's a brilliant assistant that isn't allowed to touch anything. The gap between software that tells you things and an agent that does things is the entire story of applied AI.
Questions Bo loves to be asked
- • You've stood at 'convince people they need this' once before. What does 1995 have in common with right now — and where does the parallel break down?
- • What finally broke in your own smart home that made you build an AI butler instead of buying app number thirteen?
- • You say chatbots talk and agents do. Where exactly is that line, and why does it matter for an ordinary family?
- • What can a household AI chief of staff genuinely do today — and what still needs a human?
- • You put an AI in charge of your home. How do you do that without building a surveillance box?
- • You named yours Higgins. Why give an AI a name, a voice, and a personality?
- • What will feel absurd in five years the way 'why would I need a website?' feels absurd now?
About Bo Bennett
Robert “Bo” Bennett has been building internet companies since 1994. His web-hosting firm Adgrafix grew to a five-million-dollar-a-year business before its sale to Allegiance Telecom in 2001. The next day he founded Archieboy Holdings, which today operates more than fifty web properties, including eBookIt.com.
Along the way he earned a PhD in social psychology and wrote eleven books, most on critical thinking. He lives in Greater Boston with his wife and two children, all three of whom now outrank him at operating the house.
Have Bo on your show
Email partnerships@archieboy.com
or call (978) 643-8662.
Remote on your platform of choice; in-person recording welcome around Greater Boston. Eastern Time.
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