He convinced businesses they needed a website in 1995. He’s doing it again.
Bo Bennett started a web-hosting company in 1995, when the hardest part of the job was explaining to business owners why they would ever need a website. Within five years, the question had reversed itself. He believes personal AI agents have arrived at exactly that moment — and this time he built the thing he’s explaining: PrivateChief, a managed AI chief of staff for households and businesses.
He is a working founder with thirty years of programming behind him, a PhD in social psychology, eleven books — and a smart home that once defeated his own family. Which is where this story really starts.
- Founder, PrivateChief — an AI chief of staff for the home
- Built Adgrafix, a 1995 web-hosting pioneer, to a $5M/yr business; sold to Allegiance Telecom in 2001
- President of Archieboy Holdings (50+ web properties); founder & CEO of eBookIt.com
- PhD in social psychology; author of 11 books on critical thinking and success
- Based in Greater Boston · remote-ready · Eastern Time
Three conversations Bo is ready to have
Questions he 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?
- You have a PhD in social psychology. What does the psychology say about why smart homes fail their households?
- What will feel absurd in five years the way “why would I need a website?” feels absurd now?
Robert “Bo” Bennett has been building internet companies since 1994. His web-hosting firm Adgrafix — home to some of the first web-based hosting-management and affiliate systems — 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, the ebook formatting and distribution company he has run for over a decade.
Along the way he earned a PhD in social psychology and wrote eleven books, most on critical thinking — including Logically Fallacious and Year to Success. He lives in Greater Boston with his wife and two children, all three of whom now outrank him at operating the house.
PrivateChief designs, deploys, and supervises managed AI chiefs of staff for personal life, household operations, and business administration — one agent that unifies the smart home, family logistics, and the daily administrative load, built around each household’s real work, access rules, and priorities.
Service is white-glove: remote setup nationwide, in-person installation around Greater Boston. More at privatechief.com/how-it-works.
Have Bo on your show
Email partnerships@archieboy.com (it reaches Bo directly) or call +1 (978) 643-8662. Remote interviews on your platform of choice; in-person recording welcome around Greater Boston.
Media assets: headshot · PrivateChief logo