Technology and strategy for people who build wealth.
The Upland Group is a boutique AI and automation practice for owner-operators in regulated industries. We learn how your business works, then build what fits. You own everything we build.
Custom systems for real estate, financial services, education, and healthcare. No software resale, no platform lock-in. The deliverable is a working system, not a strategy deck.
Deep SFR domain work: underwriting, comp analysis, asset management, Section 8 and subsidized-housing compliance. The proof case behind everything we automate.
Real estate investing and private equity, rebuilt on blockchain rails. Education first: financial literacy and investing fundamentals before the tools.
I grew up on job sites with a toolbelt on. My parents built and rented homes across northeast Georgia, build-to-rent before anyone had a name for it. Housing was never abstract in our family.
Neither was new technology. I watched them trade newspaper postings for internet ads, pagers for cell phones, early adopters the whole way. AI and automation are just more tools in the belt. The systems we sell were built for our own operation first: comp analysis, rent optimization, portfolio analytics, automated reporting. When we automate your business, it's the second time we've done it.
1,000 → 10,000
doors scaled at Sylvan Road, then past 15,000 at Darwin
$2.5B+
in single-family assets at portfolio peak
$100M+
annual rent roll operated
100%
of what we build, you own
What drives us
Families shouldn't need a wall of middlemen to build and protect wealth. They need infrastructure they control. Every venture under this roof points at that: the consulting practice, the education work, the technology. Different doors, same house.
Who's behind it
Kris Van Meter, founder. Over ten years running real estate operations where technology and regulation actually bite. Underwriting. Payments. Subsidized housing. His parents have been building and renting homes in northeast Georgia since the early '90s. He grew up in the middle of it.
At Sylvan Road Capital he built the underwriting and reporting systems behind an institutional SFR portfolio's climb from 1,000 to 10,000 doors, working directly with top-five private equity firms, money-center banks, and institutional joint ventures. At Darwin Homes he ran strategic client operations and product work while the platform grew past 15,000 doors, adding fully amenitized build-to-rent communities, scattered-site Section 8, and co-living operators. The footprint stretched from Miami to Baltimore and out to Minneapolis and Phoenix, every market with its own operating and regulatory quirks. In between, a stretch of finance and technology operations at Arthur Blank's PGA Tour Superstore. Underneath it all sits a real estate finance degree from the University of Georgia, a top-five program for 25 years running. He was an accounting major until the last second, then switched to what actually pulled him and stayed the extra year to finish it.
Same instinct on every job: when the tooling didn't exist, build it, and when closed systems wouldn't talk to each other, make them. He taught himself Python, SQL, and bash, turning CSV exports from siloed platforms into reporting the vendors couldn't deliver, working beside engineers out of Stanford and MIT and veterans of Meta, LinkedIn, Instacart, and DoorDash along the way. He put machine learning to work on acquisitions strategy and went deep on AI early, then led the build-out when a Wall Street client needed live data pipelines straight into its systems. The consulting practice points that same habit at other small businesses carrying the same operational weight.
