"You have the kindling and the matches... what you do with them is up to you."
Around 1972, my Aunt Muriel handed me three yellowing, typewritten pages titled "Lydia Corrina Brown-Bailey's Notes." Grandma Lydia had jotted down what she remembered of the family line, and Muriel added her own memories—including a colorful tidbit about her great-grandfather, David Solomon Bailey, a Civil War veteran who had lost a leg in the service of the Union.
Muriel reckoned David’s father was named Orange Green Bailey, and figured he must have been an Irishman who fled to America during the 1840s Potato Famine. "Orange," after all, sounded like a proper Irish name.
I tucked those three pages away. For the next twenty years, between a high-demand career in the home building industry and raising a family, there wasn't a spare minute to chase down dead relatives. The past would just have to wait.
The Cowboy & The Dial-Up Era
By 1992, I traded corporate boardrooms for a woodworking shop, launching a business crafting cowboy folk-art furniture. When custom orders were slow, I picked up consulting work for a major bank in Southern California. That gig required a whole new set of tools: a personal computer, a scanner, a printer, and this newfangled thing called an email address.
Remember AOL? The screech of the 14.4k modem became the background track of my evenings.
[1972] 3 Typewritten Pages
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[1995] cowboyup.com & Dial-Up (RootsWeb, GenWeb, Surname Mailing Lists)
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[1998] Mormon Microfiche Readers & Early Ancestry.com
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[2026] 40.9 MB PDF | 7,724 Pages | 9,000+ Names | AI Research Partner
By 1995, I registered the domain cowboyup.com. When I wasn't shaping timber, I was dipping my toes into the world of digital genealogy. In those early days, research was a wild frontier. We gathered on RootsWeb, GenWeb, and surname mailing lists, posting queries into the digital void and hoping a distant cousin in Ohio might read it. Every now and then, I’d head over to a local Mormon Church history center, cranking through reels of microfiche under the dim glow of a reader screen until my eyes crossed.
When Ancestry.com popped up around 1998, I subscribed, canceled, and re-subscribed a dozen times before finally settling in for the long haul.
Fast forward twenty-seven years: those three typewritten pages have expanded into an accurate, fully cited family tree of over 10,000 names—with a 40-generation pedigree chart spanning 7,724 pages and a 40.9-megabyte PDF file.
And as for Orange Bailey? He wasn't a 1840s Irish famine refugee at all. He was the direct descendant of John Bailey, a founding settler of Haddam, Connecticut, who stepped ashore in 1636.
The AI Frontier: A New Tool in the Shop
Last year, I decided to test a new kind of chisel: Artificial Intelligence.
After a few false starts, I settled into a groove with two AI platforms that act as hyper-efficient research assistants. But like any heavy machinery, AI comes with a warning label: it can and will make mistakes. If you don't know your subject reasonably well before you start, AI will happily lead you straight off a cliff with supreme confidence.
Used correctly, though? It uncovers obscure primary records, translates old documents, and helps synthesize centuries of scattershot data in seconds.
Which brings me to a young man named RA.
Kindling and Matches
A few days back, a new DNA match popped up on my dashboard: a young guy, RA. He had a bare-bones tree of just 23 people, but I immediately spotted two names: Nellie (my 2nd cousin) and Marcus (my grand uncle).
I felt that familiar spark—the joy of passing the torch. I shot him a message:
"Nellie gave me a photo of Orange Bailey 30+ years ago, 60 years ago I played horseshoes with Marcus, if you are interested I can guide you back to 1636 Baileys in Connecticut..."
RA wrote back promptly. He was fascinated, touched by his middle name being Bailey, and expressed a genuine sense of kinship. But then came the classic modern line:
"One thing I'm a little concerned about is your use of AI in your recent blog posts. I know AI can be a useful tool, but it can also be confidently wrong at times, so I just wanted to make sure you're fact-checking anything it helps with."
I couldn't help but smile. Here was a newcomer—holding a 23-person tree—cautioning a guy who’s spent 50 years in the archives about fact-checking.
I replied with the patience that only five decades of brick walls can teach you:
"AI is useful if you are careful. I've been studying our family history since the 1970s... What I get from AI is new information from sources I don't have access to or even know about. Coupled with DNA results, AI has absolutely broken down some brick walls. Below is a Bailey family lineage you can tap into if you want. Not a bit of this is from AI... You have the kindling and the matches... what you do with them is up to you."
The Trail Ahead
I haven't heard back from RA yet. As any veteran researcher knows, you often don't. Genealogy is a calling that catches people in its own time—usually when they're older, quieter, and looking in the mirror wondering where their story came from.
From three typewritten pages in 1972 to microfiche in 1998, to AI-driven DNA mapping in 2026, the technology changes, but the core work remains identical: searching for the truth of who came before us.
Tools don't build a house—carpenters do. AI won't write your family history for you, but if you know how to handle the tool, it sure makes the timber fit together a whole lot smoother.
Thank you Gemini AI for your wisdom and research assistance. -- Drifting Cowboy
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