Converting Homes into Co-Living Cash Machines

From Fintech to Co-Living

Charles Rossano didn’t grow up in real estate. Before founding Cohaven Capital, he spent years building and scaling fintech startups. He learned how to systematize chaos, automate workflows, and scale small teams into operational powerhouses.

When he entered real estate, he brought that same startup mindset with him. Instead of chasing 100-unit apartments or ground-up developments, he saw a massive inefficiency hiding in plain sight: underutilized single-family homes that could be transformed into thriving co-living spaces.

In just a few years, Charles and his team have turned dozens of distressed homes into profitable, high-density properties with double or triple the NOI of traditional rentals.

But it’s not just about returns. For Charles, co-living is about building community. He wants to provide affordable, well-managed housing for people who value connection as much as cost savings.

His mission is clear: use technology and data to make housing more human while delivering institutional-level results from Main Street assets.

The Play: Rent-by-the-Room with AI-Powered Ops

Charles targets distressed homes and small multifamily properties in affordable, zoning-friendly markets. Then he and his team renovate and convert them into co-living setups with 7 to 14 bedrooms per property.

What makes it work:

• Each tenant gets a private, locked room

• Shared kitchens, living areas, and sometimes bathrooms

• Monthly rents are 25 to 50% cheaper than a studio apartment

• But NOI is 2 to 3x higher than a typical single family rental

Cohaven calls this “community-first cash flow.” Tenants build real bonds—some even cook weekly dinners together. And the numbers are hard to ignore.

Why This Works

1. He treats each property like a mini-business
Every acquisition is underwritten, operated, and optimized with systems that mirror a portfolio company. The team uses SOPs, checklists, and local “SEAL team” scouts to keep standards high.

2. He built Maximus, their internal AI stack
From lead screening to market selection to maintenance workflows, Cohaven runs on a proprietary AI operating system that unlocks scale and consistency.

3. He fills units fast and keeps them full
Most properties are 90%+ occupied within 90 to 120 days of acquisition. With 7 to 10 rent-paying residents per home, breakeven happens around 60% occupancy.

The Risks (And How She Avoids Them)

Scaling too early:
Most co-living operators stall at 3–4 properties. Charles anticipated this and invested in ops from day one, using his background scaling fintechs to build for growth.

Interpersonal conflict:
Shared living brings social dynamics. Each house comes with house rules, security cameras in common areas, and color-coded plates and dishes to minimize friction.

Mismatch with neighborhood vibe:
Early on, Charles learned the hard way that not all neighborhoods want co-living. Now, they use a 50+ point checklist before acquiring—down to lawn care expectations and garbage pickup schedules.

What You Can Learn (and Steal)

1. Cash flow doesn’t have to come from scale
Charles is generating 30 to 40% total returns from single family assets by creating multiple income streams per property, without needing 100+ unit buildings.

2. Build systems like a startup
Most real estate firms operate on spreadsheets and VAs. Charles built Maximus, their AI engine, to drive consistency and make scaling predictable.

3. Solve a real problem
Over 50% of renters in many U.S. cities are cost burdened. Cohaven is solving that—while earning outsize returns. That’s a story LPs want to be a part of.

Listen to the full episode

🎙 Groundbreakers with Charles Rossano

In it, we cover:

• Why co-living might be the next Airbnb-style movement

• The 90-day system Charles uses to renovate and fill units

• How Maximus automates 80% of their operating workflows

• The overlooked risks of rent-by-the-room—and how he mitigates them

• Why he’s all in on co-living for the next 5 to 10 years