An Oklahoma agent who lived the chaos. A tech builder who knew it didn't have to be this hard.
Co-Founder & CEO | Oklahoma City
James has closed 150+ transactions—first as an investor starting in 2017, then as a licensed agent since 2020. Fix-and-flips. Commercial deals. First-time buyers. He's seen every flavor of transaction chaos—and paid for it.
The breaking point:
"I was paying $350 per file for TC services. Still waking up at 2am running deadline math in my head. 'Is inspection 3 days or 4 days out? Did that amendment change it?' I was the most expensive calendar app in Oklahoma."
That anxiety—the constant mental overhead of tracking dates, documents, and dozen email threads—became the blueprint for KeyFlo.
Why email?
"I tried every portal. SkySlope. Dotloop. Transaction desks. They all required me to stop what I was doing, log in, upload files. But I'm in my car between showings. I'm at the inspection. I'm everywhere except at a desk. Email is the only tool that's always with me."
Co-Founder & CTO | San Francisco
Cole spent 11 years building AI systems that solve messy logistics problems. As the first hire at an ML travel startup, he helped grow the company from 35 to 750 people—designing systems that drove 7% revenue increases for major airlines during the pandemic.
The realization:
"I spent a decade optimizing airline operations. Complex scheduling. Dynamic pricing. Thousands of moving parts. When James showed me agents doing deadline math in spreadsheets and tracking documents across 47 email threads, I thought: we solved harder problems than this for airlines. Real estate deserves the same."
The design philosophy:
"If it feels complicated, we built it wrong. The goal is invisible infrastructure—you forward an email, and everything just happens. No training. No onboarding videos. No 'quick start guides.' Just forward and go."
How an Oklahoma agent met a San Francisco engineer—and built something that should have existed years ago.
2025
Y Combinator's co-founder matching program. On paper, an odd pair. James: boots-on-ground real estate in Oklahoma City. Cole: Silicon Valley AI systems.
But they diagnosed the same problem from different angles. James knew what hurt. Cole knew what was possible.
Before writing a single line of code, they interviewed everyone: brokers, title companies, agents, team leaders, TCs. Dozens of conversations. Detailed breakdowns of how transactions actually flow.
The same fundamental issues came up in every conversation, for every role. A pattern emerged—and a plan took shape.
Two months of focused building. James forwarded a real contract to the early version of KeyFlo. Seconds later: every deadline extracted, every business day calculated, every date ready to share.
The technology worked. More importantly, it solved the right problems—the ones they'd heard about in every single interview.
Every transaction management tool I've ever used was built for back-office support—not for the producers who actually close deals and generate the income that pays everyone. We're stuck doing admin work that slows us down from what we're actually good at: finding homes, negotiating deals, getting people to the closing table. KeyFlo had to be different. Built for the people who produce, not just the people who process.— James Smith, Co-Founder & CEO
We're not trying to be everything everywhere on day one.
Oklahoma has 16,000+ real estate licensees dealing with the same problems as every other state:
By solving these problems deeply for Oklahoma first—with full OREC compliance, Oklahoma-specific forms, local deadline rules—we build the blueprint for every state after.
James was born in Western Oklahoma. Educated at UCO. Licensed here. His first 150 transactions were here. KeyFlo exists because Oklahoma agents deserve better tools—not coastal afterthoughts.
The Mission
Not "revolutionize." Not "disrupt." Boring.
Transactions should be predictable. Transparent. Handled. No 2am panic. No document mysteries. No "did we miss something?"
When transactions are boring, agents do what they're actually good at: finding homes, negotiating deals, building relationships.
KeyFlo handles the rest.
You're already in your inbox. We meet you there. No new logins. No new habits. Forward and go.
Fast is good. Right is non-negotiable. Every deadline links back to the source text. Every calculation has a trail.
KeyFlo handles the repetitive coordination. You stay in control. The AI extracts and calculates—you verify and decide.
We could build 100 features. We'd rather perfect the 5 that matter.
We're not outside observers trying to "fix" real estate. James has the battle scars. Every feature comes from a real problem he faced—or one an agent described to us.
Forward your executed contract to tc@keyflo.ai and watch it work.
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