LoftSmart: First Hire to $40M Series A

The Opportunity

In 2016, I moved to New York to begin my journey as an entrepreneur. The student housing market was broken — fragmented listings, zero transparency on pricing, no way to do virtual tours, and a leasing process stuck in the paper age. Millions of college students were signing leases for apartments they'd never seen, with landlords they couldn't verify.

Sam Bernstein and Sundeep Kumar were building LoftSmart at AngelPad, one of the top startup accelerators. They had a strong business plan and early MVP, but with only 30 days left in the program, they needed a technical leader to turn their vision into a shipping product. That's where I came in.

The 30-Day Sprint

I joined as the first technical hire and Head of Product with an impossible deadline: build an entire transactional platform for student housing in the final month of AngelPad. Working with Z1 Digital as our design and development partner, we crafted the first prototype of the transactional marketplace under extreme time pressure.

The early version launched in June 2016, and investors immediately took notice. The seed round closed at nearly $2M, led by Corigin Ventures (a real estate-focused venture fund), with additional capital from Expansion Venture Capital, Full Tilt Capital, and Metaprop NYC.

Three Products, One Platform

Over the next two years, I led the creation of three interconnected products that formed the complete LoftSmart experience:

1. Rental Apartment Marketplace

The core product — a search and discovery platform where students could find off-campus housing with verified listings, real photos, and transparent pricing. We built deep integrations to make the experience trust-first:

2. End-to-End Property Management Platform

On the landlord side, we built tools for property managers to list units, manage applications, screen tenants, and handle maintenance requests — all integrated with the marketplace.

3. Rent Payments System

We completed the loop by building a payments infrastructure that formalized and digitized the entire rent collection process, giving both students and property managers transparency and security.

Scaling & Evolution

The platform went through a major redesign applying new branding by Zack Davenport, and we fully implemented the end-to-end online leasing process. The product evolved from a simple listing site into a comprehensive marketplace trusted by both student renters and property managers.

We worked sprint-to-sprint with Z1 Digital for three years, moving from a hectic startup pace to a disciplined cadence of weekly meetings, iterative development, and continuous user feedback loops.

The Outcome

Two years after the first prototype, LoftSmart raised a $40M Series A — validating that a technology-first approach to student housing could create a marketplace trusted by students, property managers, and investors alike. We made the off-campus housing market transparent and trustworthy, disrupting a space that had been stuck in the analog era.

The LoftSmart experience was formative for me. It's where I learned to thrive in ambiguity, move at startup speed, and — most importantly — work with non-technical founders to turn their vision into digital reality. Every company I've built or led since has been shaped by those two intense years.