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.

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What we do

AI Consulting & Automation

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.

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Real Estate Operations

Deep SFR domain work: underwriting, comp analysis, asset management, Section 8 and subsidized-housing compliance. The proof case behind everything we automate.

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Covey coming

Real estate investing and private equity, rebuilt on blockchain rails. Education first: financial literacy and investing fundamentals before the tools.

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Where the expertise comes from

I grew up on my dad's job sites in northeast Georgia. He built spec homes at scale starting in 1994, build-to-rent before anyone had a name for it, and housing was never abstract in our family. 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 trust technology. Different doors, same house.

Who's behind it

Kris Van Meter, founder. Twelve years running real estate operations where technology and regulation actually bite. Underwriting. Payments. Subsidized housing. 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 of 300-plus homes, scattered-site Section 8 from Baltimore to Indiana, and co-living operators like PadSplit.

The pattern the whole way: when the tooling didn't exist, build it, and when closed systems wouldn't talk to each other, make them. He taught himself Python and SQL in Jupyter notebooks, turning CSV exports from siloed platforms into reporting the vendors couldn't deliver. Then he put machine learning and statistical analysis to work on acquisitions strategy and went deep on AI early, because it multiplied what one operator can ship. The consulting practice points that same habit at other small businesses carrying the same operational weight.

Tell us what's slowing you down

Two sentences is plenty. You'll hear back from Kris directly, usually within a business day.